Category: 13599-22-9

So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Teng, Qing-Hu; Sun, Gui-Xia; Luo, Shu-Ying; Wang, Kai; Liang, Fu-Pei researched the compound: 1,5-Diphenyl-1H-pyrazole-3-carboxylic acid( cas:13599-22-9 ).Application of 13599-22-9.They published the article 《Design, syntheses and antitumor activities evaluation of 1,5-diaryl substituted pyrazole secnidazole ester derivatives》 about this compound( cas:13599-22-9 ) in Journal of Heterocyclic Chemistry. Keywords: diaryl pyrazole secnidazole ester preparation antitumor activity apoptosis cytotoxicity. We’ll tell you more about this compound (cas:13599-22-9).

According to the drug hybridization principle, a series of novel 1,5-diaryl substituted pyrazole secnidazole ester derivatives I (R1 = 4-I, 3-Me, 4-Cl, etc.; R2 = H, Me, Cl) have been synthesized by the combinations of various 1,5-diarylpyrazole-3-carboxylic acids II with secnidazole. The in vitro antitumor/cytotoxicities activities against tumor and normal cell lines, including NCI-H460 (lung tumor cell), MCG-803 (gastric tumor cell), Skov-3 (ovarian tumor cell), BEL-7404 (liver tumor cell) and HL-7702 (normal liver cell), have been evaluated using MTT assay. All compounds I showed promising inhibitory activities against four tumor cell lines. The IC50 of I (R1 = 4-I; R2 = H) against the BEL-7404 cell was 2.03μM, and those of I (R1 = 3-Me; R2 = H) against the NCI-H460, MCG-803 and Skov-3 were 1.34, 0.14, and 0.87μM, resp. All these values were much lower than those of the cisplatin. Furthermore, I (R1 = 3-Me, R2 = H; R1 = 4-I, R2 = H) were also verified to be considerably safe for normal human liver cell, since the lower IC50 values than cisplatin. Based on these results, the cell cycle anal., apoptosis ratio detection and mitochondrial membrane potential assay of I (R1 = 3-Me, R2 = H; R1 = 4-I, R2 = H) were further performed aiming to investigate their inhibition mechanism of BEL-7404 cells. It is revealed that they have effectively inhibited the cell growth by arresting the BEL-7404 cells at S phase and induced apoptosis through the mitochondria-mediated pathway.

This compound(1,5-Diphenyl-1H-pyrazole-3-carboxylic acid)Application of 13599-22-9 was discussed at the molecular level, the effects of temperature and reaction time on the properties of the compound were discussed, and the optimum reaction conditions were selected.

Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Reactivity of the flavanone nucleus. II. Effect of substituents on the reaction with phenylhydrazine》. Authors are Venturella, Pietro.The article about the compound:1,5-Diphenyl-1H-pyrazole-3-carboxylic acidcas:13599-22-9,SMILESS:OC(=O)C1=NN(C(=C1)C1=CC=CC=C1)C1=CC=CC=C1).Recommanded Product: 1,5-Diphenyl-1H-pyrazole-3-carboxylic acid. Through the article, more information about this compound (cas:13599-22-9) is conveyed.

cf. CA 55, 15467b. Substituents in the flavanone nucleus do not particularly affect the conversion of their phenylhydrazones into pyrazoline derivatives The possibility to isolate the intermediate phenylhydrazones depends on the nature and the position of the substituents. The appropriate flavanone (0.5 g.) in 10 cc. 95% EtOH refluxed 1 hr. with 0.3 g. PhNHNH2, kept some time, and diluted with H2O gave the corresponding phenylhydrazone. In this manner were prepared the following compounds: 2-(p-methoxyphenyl)flavanone phenylhydrazone (I); 2-[3,4-(CH2O2)C6H3] analog (II) of I, m. 127-8°; 2-(3,4-methyl-enedioxyphenyl)-5,6,8-trimethoxyflavanone phenylhydrazone (III) (without EtOH), m. 129-31°; 2-Ph analog of III; 2-phenyl-6-methoxyflavanone phenylhydrazone (IV); and the 5,6-di-MeO analog of IV, needles, m. 118-20°. The appropriate flavanone (0.5 g.) and excess PhNHNH2 heated a few min. in a test tube over a free flame, cooled, dissolved in AcOH, and poured into H2O gave the corresponding 3,5-diarylpyrazoline (V). The appropriate flavanone (0.5 g.) in 5 cc. AcOH refluxed 1 hr. with 0.3 g. PhNHNH2, cooled, and diluted with H2O gave the corresponding V. The appropriate chalcone (0.2 g.) and PhNHNH2 heated a few min. in a test tube over a free flame, dissolved in AcOH, and poured into H2O gave the corresponding V. The appropriate phenylhydrazone refluxed 1 hr. with AcOH gave the corresponding V. The appropriate V refluxed with Ac2O and NaOAc gave the corresponding acetate which fluoresces in EtOH intensely blue-green. By these methods were prepared the following V and their acetates (3- and 5-aryl group, crystal form, and m.p., and m.p. of acetate given): o-HOC6H4, p-MeOC6H4 (Va), needles, 168-9°, 132-3°; o-HOC6H4, 3,4-(CH2O2)C6H3 (VI), needles, 145-6°, 116-17°; 2,3,5,6-HO(MeO)3C6H, 3,4-(CH2O2)C6H3 (VIa), needles, 185-6°, 195-6°, 2,3,5,6-HO(MeO)3C6H, Ph (VII), yellow-green plates, 193-4°, 132-3°; 2,5-HO(MeO)C6H3, Ph (VIII), needles, 150-1°, 114-15°; 2,5,6-HO(MeO)2C6H2, Ph (IX), yellow plates, 147-8°, 147°, VII or VIII or IX (1 g.) in 30 cc. refluxing 5% aqueous NaOH treated gradually with 6.5 g. KMnO4 in 70 cc. H2O, refluxed 3 hrs., and worked up gave 1,5-diphenyl-3-pyrazolecarboxylic acid, m. 183-5° (EtOH). Va or VI, or Via oxidized similarly with 8 g. KMnO4 in 100 cc. H2O gave 1-phenyl-3,5-pyrazoledicarboxylic acid, platelets, m. 265-6° (H2O). The ultraviolet absorption spectra of the various pyrazolines, and II, III, and V, and the infrared absorption spectra of VI and its acetate are recorded.

《Reactivity of the flavanone nucleus. II. Effect of substituents on the reaction with phenylhydrazine》 provides a strategy for the preparation of materials with excellent comprehensive properties, which is conducive to broaden the application field of this compound(1,5-Diphenyl-1H-pyrazole-3-carboxylic acid)Recommanded Product: 1,5-Diphenyl-1H-pyrazole-3-carboxylic acid.

Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Synthesis of (pentahydroxypentyl)pyrazoles by reaction of D-galactose arylhydrazones with 2-nitro-1-phenylalkenes, published in 1986-12-31, which mentions a compound: 13599-22-9, mainly applied to galactose arylhydrazone cyclocondensation phenylnitroalkene; nitrophenylalkene arylhydrazone galactose cyclocondensation; hydroxypentylpyrazole, HPLC of Formula: 13599-22-9.

The reactions of aldehydo-D-galactose phenylhydrazones I (R = Ph) with β-nitrostyrene II (R1 = H, Me) gave diphenylpyrazoles III (R = Ph, R1 = H, Me); similarly I (R = p-MeC6H4) and II (R1 = Me) gave III (R = p-MeC6H4, R1 = Me). I (R = p-MeC6H4) and II (R1 = H) gave tolylpyrazole IV showing the reverse regiochem. to that previously observed III and IV were converted to pentaacetates or oxidized by IO4- to pyrazole-3-carboxaldehydes which were then converted to carboxylic acids by moist Ag2O.

《Synthesis of (pentahydroxypentyl)pyrazoles by reaction of D-galactose arylhydrazones with 2-nitro-1-phenylalkenes》 provides a strategy for the preparation of materials with excellent comprehensive properties, which is conducive to broaden the application field of this compound(1,5-Diphenyl-1H-pyrazole-3-carboxylic acid)HPLC of Formula: 13599-22-9.

Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Hydrogenation of isoxazoles with Raney nickel》. Authors are D’Alcontres, G. Stagno.The article about the compound:1,5-Diphenyl-1H-pyrazole-3-carboxylic acidcas:13599-22-9,SMILESS:OC(=O)C1=NN(C(=C1)C1=CC=CC=C1)C1=CC=CC=C1).COA of Formula: C16H12N2O2. Through the article, more information about this compound (cas:13599-22-9) is conveyed.

The object of the work was to ascertain whether 4-isoxazolines are capable of existence and whether it is possible to prepare them by hydrogenation of isoxazole (I) and its derivatives by a reaction analogous to that of the formation of pyrazolines from pyrazoles [Ber. 26, 100(1893)]. Under the conditions used by Claisen with I derivatives, the ring is opened with formation of the isomeric imino ketones, NH:CRCHR’COR” (IA) (cf. Ber. 24, 3912(1891)), so a less drastic method had first of all to be derived. To this end, Raney Ni (II) in neutral alc. or aqueous media at room temperature and atm. pressure (according to the nature of the I derivative) was tested as a catalyst. In all cases, hydrogenation progressed smoothly, but in no case was a cyclic isoxazoline isolated, and, on addition of 1 H mol., opening of the nucleus occurred, with formation of IA. The experiments confirm the instability of the cyclic system of 4-isoxazolines, which are probably incapable of existence, or at least it is probably impossible to synthesize them by hydrogenation of the I nucleus (Panizzi, C.A. 40, 7190.1). I (2 g.) in 20 cc. alc. and 1.5 g. II, hydrogenated and filtered, give a liquid which has the odor of NH3, is alk. to litmus, gives a blood-red color with FeCl3, and reduces warm NH3AgNO3. This reaction liquid (15 cc., i.e., 0.5 the total) and p-O2NC6H4NHNH2 (III), allowed to stand 1 hr., filtered, and the residue (1.54 g.) purified by dilute EtOH and animal charcoal, yields 1-(p-nitrophenyl)pyrazole (IV), m. 168.5-9°, insoluble in aqueous alkalies and gives no color with them. The other half of the reaction liquor gives no precipitate with H2NCONHNH2.HCl and NaOAc, even after several days. 1-Phenylpyrazole (2 g.), poured very slowly into ice-cold fuming HNO3 (much heat is evolved), allowed to stand, poured into ice water, and the precipitate (3.1 g.) purified by EtOH, yields IV. Dimethylisoxazole (5 g.) in 50 cc. alc. and 2.5 g. II, hydrogenated, filtered, slowly evaporated, and the sirupy residue allowed to stand in vacuo until crystallized, yields MeC(:NH)CH2Ac (V), m. 43° (from EtOH) [cf. Ber. 24, 3915(1881); Bull. soc. chim. 7, 779(1892)]. V (0.5 g.) in dilute AcOH and III in AcOH give a precipitate of 1-(p-nitrophenyl)-3,5-dimethylpyrazole (VI), light yellow, m. 99.5-100° (from dilute EtOH). VI (0.35 g.) in 10 cc. dilute H2SO4, distilled, part of the distillate treated with III, and the precipitate purified by EtOH, yields VI. Another part of the distillate and KOH distilled, and the distillate treated with III, give a p-nitrophenylhydrazone, m. 148.5°. The mother liquor gives the reaction of AcOH. The distillation residue, treated with H2SO4, and made alk., evolves NH3. Diphenylisoxazole (1.5 g.) in 80 cc. alc. and 3 g. II, hydrogenated (with FeCl3 the reaction liquor turns dark green, then red) and evaporated, yields dibenzoylmethaneimide, PhC(:NH)CH2Bz (VII), m. 97° (from alc.), soluble in acids and reprecipitated by aqueous alkali carbonates. VII (0.5 g.) in 20 cc. dilute H2SO4, refluxed 30 min., half of the liquid saturated with (NH4)2SO4, extracted with Et2O, the extract dried, and the residue purified by EtOH, yields the compound C15H12O2, m. 77-8°; FeCl3 turns its alc. solutions violet-red. The other half of the liquid, extracted with Et2O, and the residue treated with concentrated KOH, evolves NH3. VII (0.2 g.) in dilute AcOH and PhHNNH2 (VIII), heated to boiling and allowed to stand, yield 1,3,5-triphenylpyrazole, m. 137-8° (from Et2O) [cf. Ber. 21, 1206(1888); Ann. 308, 252(1889)]. O.N:CMe.CH:CCO2Na (4 g.) in 40 cc. water and 2 g. II, hydrogenated, filtered, and the green filtrate kept in vacuo, leaves a sirupy residue (IX) whose aqueous solutions are alk. to litmus, turn blood-red with FeCl3, and with KOH evolve NH3. Aqueous IX and III give 1-(p-nitrophenyl)-3-methyl-5-pyrazolecarboxylic acid, m. 231° (from EtOH) (cf. Musante and Berretti, C.A. 44, 4905a). VIII (2 cc.), 7 cc. water, 0.3 cc. glacial AcOH, and 0.3 g. IX, heated and allowed to stand yield 1-phenyl-3-methyl-5-carboxypyrazole, m. 189-90° (from hot water), decompose 200-10°, with evolution of CO2 and formation of 1-phenyl-3-methylpyrazole. VIII (1 g.) in 25 cc. dilute H2SO4, boiled, saturated with (NH4)2SO4, extracted with Et2O, and the extract evaporated yields the compound C5H6O4 (IX), m. 98° (from C6H6). IX (0.1 g.) in boiling aqueous KOH evolves Me2CO, and the distillate gives with III a p-nitrophenylhydrazone, yellow, m. 148°. The distillation residue, acidified with AcOH, and aqueous CaCl2 added, precipitates Ca oxalate (X). O.N:C(CO2Na).CH:CMe (3.5 g.) in 40 cc. water and 2 g. II, hydrogenated, and the filtered product evaporated, gives a green sirupy product, which with III yields 1-(p-nitrophenyl)-3-methyl-5-pyrazolecarboxylic acid (XI), m. 231° (from EtOH), turns intense red with FeCl3; with KOH its aqueous solutions evolve NH3; boiling in dilute H2SO4 and extraction with Et2O yields a compound m. 98°. O.N:C(CO2Et).CH:CHMe (5 g.) in 40 cc. alc. and 2 g. II, hydrogenated (the mixture turns brown, is alk., and gives with FeCl3 a cherry-red solution), and the filtered product allowed to evaporate, yields a compound (XII), C7H11O3N, m. 109-10° (from EtOH), soluble in dilute aqueous alkalies; in boiling aqueous KOH it evolves NH3 and Me2CO, and the residue contains X. XII and III in dilute AcOH precipitate a compound which, purified by dilute EtOH and animal charcoal, yields Et 1-(p-nitrophenyl)-3-methyl-5-pyrazolecarboxylate (XIII), yellowish, m. 78-9°. Alc. XIII (0.5 g.) and 0.4 g. KOH in 4 cc. water, refluxed 75 min., evaporated, the residue taken up in water, filtered, the filtrate acidified with HCl, and the precipitate purified by EtOH and animal charcoal, yield XI. O.N:CPh.C(CO2Na):CMe (1.2 g.) in 25 cc. water and 1 g. II, hydrogenated (the product is alk. and turns red with FeCl3), and evaporated, leaves a sirup (XIV), which with HCl evolves CO2. XIV and KOH evolve NH3; distillation (odor of BzMe) and treatment of the distillate with III in AcOH gives p-O2NC6H4NHN:CPhMe. The mother liquor, saturated with (NH4)2SO4, extracted with Et2O, and the extract evaporated, leaves HCO2H. Aqueous XIV and dilute H2SO4 (1:1), allowed to stand until no more CO2 is evolved, saturated with NH3, extracted with Et2O, and the extract evaporated, leave a yellow acidic oil (XV) which reduces NH3-AgNO3. XV, exactly neutralized with dilute NaOH, and aqueous PhNH2.HCl added, yields BzCH2CH:NPh, m. 140-1° (from EtOH) [cf. Ber. 20, 2192(1887)]. O.N:C(CO2Na).CH:CPh (2 g.) in 30 cc. water and 1 g. II, hydrogenated, the reaction liquor (alk. to litmus and turns orange-red with FeCl3) acidified with dilute H2SO4, filtered (the filtrate has the odor of NH3), and the residue purified by C6H6, yield PhC(:NH)CH2COCO2H (XVI), m. 161° (decomposition) (Mumm and Münchmeyer, C.A. 5, 703). XVI (0.48 g.) in dilute AcOH and VIII in AcOH give a precipitate of diphenylpyrazolecarboxylic acid (XVII), m. 185° (from C6H6) [cf. Ber. 20, 2186(1887)]. XVII, heated until no more CO2 is evolved, then at 250°, the yellow oil allowed to solidify in vacuo, dissolved in aqueous HCl, and water added, precipitates a compound, C15H12N2 (XIX), m. 55-6°. XIX in dilute H2SO4, refluxed 1 hr., allowed to stand, filtered, and the residue purified by boiling water, yields a compound, C10H8O4.2H2O (XX), m. 156-8° (decomposition to BzMe); its aqueous solutions are acid to litmus; its solutions in concentrated H2SO4 are purple-red (decolorized by dilution with water). Na salt, precipitates with aqueous FeSO4 a dark blue compound and, fused with resorcinol, gives a dark red product. The mother liquor from XX and aqueous KOH evolve NH3. O.N:CMe.C(CO2Na):CPh (3.1 g.) in 20 cc. water and 1.5 g. II, hydrogenated, the liquid (yellow, alk., and turns intense red with FeCl3), acidified with dilute HCl, evaporated, and the residue purified by boiling EtOH, yield a compound C11H11O3N (XXI), m. 89-90°. XXI in dilute H2SO4, distilled, and the distillate allowed to stand, yields a compound, C10H10O2, m. 60-1°, soluble in aqueous alk. carbonates, with FeCl3 turns Bordeaux red. Treatment of the mother liquor with aqueous KOH yields NH3. XXI in dilute AcOH and VIII in AcOH give 1-(p-nitrophenyl)-3-methyl-5-phenylpyrazole, m. 100-1° (from MeOH) (Reilly, et al., C.A. 26, 452).

Different reactions of this compound(1,5-Diphenyl-1H-pyrazole-3-carboxylic acid)COA of Formula: C16H12N2O2 require different conditions, so the reaction conditions are very important.

Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Reaction between aroylacetones and arylhydrazines》. Authors are Finar, I. L.; Simmonds, Alma B..The article about the compound:1,5-Diphenyl-1H-pyrazole-3-carboxylic acidcas:13599-22-9,SMILESS:OC(=O)C1=NN(C(=C1)C1=CC=CC=C1)C1=CC=CC=C1).Computed Properties of C16H12N2O2. Through the article, more information about this compound (cas:13599-22-9) is conveyed.

PhNHNH2 and ο-, m-, and p-nitrobenzoylacetones react to form only 5-ο-, -m-, and -p-nitrophenyl-3-methyl-1-phenylpyrazoles (I), 3,1,-5-MePh(x-O2NC6H4)C3HN2, whereas BzCH2Ac and 2,4-(O2N)2C6H3NHNH2 give both 1-(2,4-dinitrophenyl)-3-methyl-5-phenylpyrazole (II) and 1-(2,4-dinitrophenyl)-5-methyl-3-phenylpyrazole (III). The orientation of I (x = 3 or 4) (IIIa, IIIb) was established by reduction to the amine, diazotization, and treatment with H3PO2 to give 3-methyl-1,5-diphenylpyrazole (IV). Similar treatment of I (x = 2) (IVa) gave 3-methyl-1-phenyl-1H-pyrazolo[4,5-c]cinnoline (V) instead of the expected methyldiphenylpyrazole. To prevent the formation of V, IVa was converted into the 4-Br derivative Reduction to the amine, followed by diazotization and treatment of the diazonium salt (VI) with H3PO2 gave 4-bromo-3-methylpyrazolo[1,2-d]phenanthridine (VII). Oxidation of IV by boiling with KMnO4 in dilute C5H5N gave authentic 1,5-diphenylpyrazole-3-carboxylic acid. PhNHNH2 (1.3 g.) and 2.35 g. ο-O2NC6H4COCH2Ac heated 10 min. in alc. at 35-40° gave 3.17 g. yellow phenylhydrazone (IX), m. 156° (cf. Koenigs and Freund, C.A. 42, 1935h). Heating 10 g. diketone in alc. with 5.4 g. PhNHNH2 in alc. on a steam bath 5 min. gave 6.4 g. of another form of the phenylhydrazone (IXa), m. 136°, together with 7.5 g. IVa. Colorless IXa boiled in alc. and the solution cooled quickly gave IX. Both IX and IXa heated in alc. on a steam bath or recrystallized from CHCl3, AcOH, or C6H6 slowly formed IVa. PhNHNH2 (1.2 g.) and 2.3 g. m-O2NC6H4COCH2Ac refluxed 3 hrs. in alc. yielded 93% IIIa, m. 102-3°. Condensation of p-O2NC6H4COCl with AcCH2CO2Et in the presence of NaOMe in MeOH by an adaptation of the method of Bülow and Hailer [Ber. 35, 932(1902)], dilution of the mixture with ice H2O, filtration, pouring the filtrate into cold AcOH, and extraction with Et2O yielded 48% p-O2NC6H4COCH2CO2Et, converted according to Knorr and Jödicke [Ber. 18, 2259(1885)] to 3-methyl-5-(p-nitrophenyl)-1-phenylpyrazole-4-carboxylic acid (X), m. 210°, and transformed by heating 3 hrs. at 240-50° to IIIb, m. 111-12°, also obtained in 36% yield by refluxing 2.0 g. p-O2NC6H4COCH2Ac and 1.1 g. PhNHNH2 in alc. BzCH2Ac (20 g.) in alc. and 16 g. 2,4-(O2N)2C6H3NHNH2 in 32 ml. 98% H2SO4 and 350 ml. hot alc. heated 10 min. on a steam bath and the mixture decanted gave 15.3 g. II, m. 137° (alc. or AcOH). The decanted solution cooled and filtered yielded 2.1 g. III, m. 154° (alc. or AcOH). IVa, II, and III in AcOH treated with excess Br at room temperature and filtered, the precipitate taken up in CHCl3, and the solution washed with aqueous Na2CO3 and H2O gave 86, 93, and 91% of the corresponding 4-Br derivatives m. 141, 176, and 158°, resp. The nitro compounds IIIa, IIIb, and IVa (1 mole) in alc. heated 1 hr. on a steam bath with 8 moles SnCl2 in concentrated HCl and the cooled solution made alk. with 30% NH4OH, the amine extracted with Et2O, and recrystallized (alc.) yielded the corresponding 5-aminophenyl-3-methyl-1-phenylpyrazoles (XI): m-amino (XIa), m. 161.5°; p-amino (XIb), m. 93°; ο-amino (XIc), m. 96°, also obtained as a better product, m. 99°, by heating 17.5 g. IVa in 10 ml. 60% N2H4.H2O in alc. on a steam bath in the presence of 2 g. Pd-C. Similar reduction of 10 g. 4-Br derivative of IVa gave 5.1 g. 5-(ο-aminophenyl)-4-bromo-3-methyl-1-phenylpyrazole (XId), m. 135°. X was converted by the procedure of K. and J. (loc. cit.) to the corresponding 5-(p-aminophenyl)-3-methyl-1-phenylpyrazole-4-carboxylic acid (XIe), m. 261°. II (8 g.) in 500 ml. alc. and 15 ml. 30% NH4OH saturated with H2S heated 1 hr. on a steam bath and evaporated, the crystalline product (5.3 g.) taken up in concentrated HCl and filtered, the filtrate diluted with H2O, and the precipitate crystallized gave 1-(4-amino-2-nitrophenyl)-3-methyl-5-phenylpyrazole (XII), m. 182° (alc.). III (1.4 g.) in 60 ml. alc. and 3 ml. 30% NH4OH reduced with H2S yielded 54% 1-(4-amino-2-nitrophenyl)-5-methyl-3-phenylpyrazole, m. 170° (alc. or ligroine). The aminophenylpyrazoles (0.6 g.) in 3 ml. concentrated HCl were diazotized 30 min. with 0.3 g. NaNO2 in 0.5 ml. H2O and the solution poured into 7 ml. 30% H3PO2. XIa and XIb both gave IV, characterized as its Br derivative m. 75°. XIe gave authentic 3-methyl-1,5-diphenyl-pyrazole-4-carboxylic acid, m. 205°. The product obtained by heating 4-chloroquinaldine with excess PhNHNH2 in a sealed tube at 200° (K. and F., loc. cit.) was shown to be 3-(ο-aminophenyl)-5-methyl-1-phenylpyrazole (XIII) since it gave 5-methyl-1,3-diphenylpyrazole (picrate, m. 108°). XIc gave V, m. 216°, also obtained when the diazonium salt solution was heated with alc. and Gattermann Cu powder or with boiling 50% H2SO4, or was made alk. with NaOH solution XId was similarly converted through the diazonium salt VI to VII, m. 140°. XII gave red needles, m. 108°, by the above procedure but deaminating by addition of 1 g. XII, in 12 ml. AcOH to 0.3 g. NaNO2 in 1.5 ml. concentrated H2SO4 at 5°, keeping the mixture 30 min. at 5°, heating 30 min. on a steam bath with 20 ml. alc., diluting with H2O, and extracting with Et2O gave authentic 3-methyl-1-(ο-nitrophenyl)-5-phenylpyrazole, m. 104°. Reduction of the aminophenylpyrazoles with Na and alc. and evaporation, solution in concentrated H2SO4, and addition of aqueous NaNO2 according to the Knorr pyrazoline reaction procedure gave red color with XIa, XIb, XIc, and 1-(ο-aminophenyl)-3-methyl-5-phenylpyrazole (C.A. 51, 7357g), and a blue color with XIII.

The article 《Reaction between aroylacetones and arylhydrazines》 also mentions many details about this compound(13599-22-9)Computed Properties of C16H12N2O2, you can pay attention to it, because details determine success or failure

Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Waterson, Alex G.; Kennedy, J. Phillip; Patrone, James D.; Pelz, Nicholas F.; Feldkamp, Michael D.; Frank, Andreas O.; Vangamudi, Bhavatarini; Souza-Fagundes, Elaine M.; Rossanese, Olivia W.; Chazin, Walter J.; Fesik, Stephen W. published an article about the compound: 1,5-Diphenyl-1H-pyrazole-3-carboxylic acid( cas:13599-22-9,SMILESS:OC(=O)C1=NN(C(=C1)C1=CC=CC=C1)C1=CC=CC=C1 ).SDS of cas: 13599-22-9. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:13599-22-9) through the article.

Replication Protein A is the primary eukaryotic ssDNA binding protein that has a central role in initiating the cellular response to DNA damage. RPA recruits multiple proteins to sites of DNA damage via the N-terminal domain of the 70 kDa subunit (RPA70N). Here the authors describe the optimization of a diphenylpyrazole carboxylic acid series of inhibitors of these RPA-protein interactions. The authors evaluated substituents on the aromatic rings as well as the type and geometry of the linkers used to combine fragments, ultimately leading to submicromolar inhibitors of RPA70N protein-protein interactions.

Compounds in my other articles are similar to this one(1,5-Diphenyl-1H-pyrazole-3-carboxylic acid)SDS of cas: 13599-22-9, you can compare them to see their pros and cons in some ways,such as convenient, effective and so on.

Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Recommanded Product: 1,5-Diphenyl-1H-pyrazole-3-carboxylic acid. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 1,5-Diphenyl-1H-pyrazole-3-carboxylic acid, is researched, Molecular C16H12N2O2, CAS is 13599-22-9, about A study on rearrangement of arylazo furanones and pyrrolinones. Author is El-Kousy, S. M.; El-Torgoman, A. M.; Salama, G. M.; Hashem, A. J..

Rearrangement of 5-phenyl-2,3-furandione 3-(phenylhydrazones) and 5-phenyl-2,3-furandione 3-[(4-chlorophenyl)hydrazones] gave 5-phenyl-1H-pyrrole-2,3-dione 3-(phenylhydrazones) and 5-phenyl-1H-pyrrole-2,3-dione 3-[(4-chlorophenyl)hydrazones]. Rearrangement of 5-phenyl-1H-pyrrole-2,3-dione 3-(phenylhydrazones) gave 1H-pyrazole-3-carboxylic acids. The oxopyrroline derivatives 4 were converted into 5 by treatment with phosphorous oxychloride. Replacement of chlorine atom in 5 was affected using aniline to give 6.

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Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Safety of 1,5-Diphenyl-1H-pyrazole-3-carboxylic acid. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 1,5-Diphenyl-1H-pyrazole-3-carboxylic acid, is researched, Molecular C16H12N2O2, CAS is 13599-22-9, about Pyrazole carboxamides and carboxylic acids as protein kinase inhibitors in aberrant eukaryotic signal transduction: Induction of growth arrest in MCF-7 cancer cells. Author is Persson, Tobias; Yde, Christina W.; Rasmussen, Jakob E.; Rasmussen, Tine L.; Guerra, Barbara; Issinger, Olaf-Georg; Nielsen, John.

Densely functionalized pyrazolecarboxamides, e.g. I, and pyrazolecarboxylic acids were prepared through saponification and transamidation of ester-functionalized pyrazoles. This synthetic protocol allowed for three diversifying steps in which appendages on the pyrazole scaffold were adjusted to optimize inhibition of protein kinases. Thirty-five analogs were tested in CK2, AKT1, PKA, PKCα, and SAPK2a (p38) kinase inhibition bioassays. Blocking of these kinases may lead to effective therapies for treating inflammatory diseases and cancer. In order to investigate potential biol. activity, MCF-7 human breast cancer cells were incubated with the most promising derivatives Two analogs caused changes in MCF-7 cell growth, one of them through cell cycle arrest demonstrated by cell cycle anal.

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Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 1,5-Diphenyl-1H-pyrazole-3-carboxylic acid(SMILESS: OC(=O)C1=NN(C(=C1)C1=CC=CC=C1)C1=CC=CC=C1,cas:13599-22-9) is researched.Safety of 3,5-Di(pyridin-2-yl)-4H-1,2,4-triazol-4-amine. The article 《Discovery of 1,5-Diphenylpyrazole-3-Carboxamide Derivatives as Potent, Reversible, and Selective Monoacylglycerol Lipase (MAGL) Inhibitors》 in relation to this compound, is published in Journal of Medicinal Chemistry. Let’s take a look at the latest research on this compound (cas:13599-22-9).

Monoacylglycerol lipase (MAGL) is a serine hydrolase that plays an important role in the degradation of the endocannabinoid neurotransmitter 2-arachidonoylglycerol, which is implicated in many physiol. processes. Beyond the possible utilization of MAGL inhibitors as anti-inflammatory, antinociceptive, and anticancer agents, their application has encountered obstacles due to the unwanted effects caused by the irreversible inhibition of this enzyme. The possible application of reversible MAGL inhibitors has only recently been explored, mainly due to the deficiency of known compounds possessing efficient reversible inhibitory activities. The authors report a new series of reversible MAGL inhibitors. Among them, compound 26 ((4-benzylpiperidin-1-yl)(5-(4-hydroxyphenyl)-1-(3-methylbenzyl)-1H-pyrazol-3-yl)methanone) showed to be a potent MAGL inhibitor (IC50 = 0.51 μM, Ki = 412 nM) with a good selectivity vs. fatty acid amide hydrolase (FAAH), α/β-hydrolase domain-containing 6 (ABHD6), and 12 (ABHD12). Interestingly, this compound also possesses antiproliferative activities against two different cancer cell lines and relieves the neuropathic hypersensitivity induced in vivo by oxaliplatin.

In some applications, this compound(13599-22-9)Safety of 1,5-Diphenyl-1H-pyrazole-3-carboxylic acid is unique.If you want to know more details about this compound, you can contact with the author or consult more relevant literature.

Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Formazyls. III. A new method of synthesis of pyrazoles. Application to the synthesis of 3-arylazopyrazoles and 3-aminopyrazoles》. Authors are Fusco, Raffaello; Romani, Roberto.The article about the compound:1,5-Diphenyl-1H-pyrazole-3-carboxylic acidcas:13599-22-9,SMILESS:OC(=O)C1=NN(C(=C1)C1=CC=CC=C1)C1=CC=CC=C1).Synthetic Route of C16H12N2O2. Through the article, more information about this compound (cas:13599-22-9) is conveyed.

cf. C.A. 42, 1232d. Compounds of the ArN:NC(Hal):NNHAr type studied in the previous work show the properties of both formazyls and hydrazonic halides because of the C(Hal):NNH group common to the 2 classes. In the present work their behavior as hydrazonic halides was examined by an investigation of their cyclization to pyrazolic and other heterocyclic systems according to methods of synthesis alrady developed by F. and collaborators. This offered the possibility of preparing pyrazoles with arylazo groups in the 3-position, which have not been described, and which should be reducible to NH2 derivatives PhN:NCCl:NNHPh (I) was used as a starting compound In general I was found to be more reactive than the hydrazonic halides previously studied, probably because of the great mobility of the Cl atom in such a central position. However, this reactivity does not result in high yields, but in darkening, evolution of gas, isonitrile odor, formation of resins, and general difficulty in isolating the desired products. Of the various methylenic agents studied, β-ketonic acid nitriles and β-diketones gave the best results. A suspension of 2.58 g. (0.01 mol) I in 20 cc. anhydrous MeOH, poured into 0.01 mol AHcCNaCN in 20 cc. anhydrous MeOH at 0° (spontaneous heating, evolution of gas, darkening, and precipitation of NaCl), allowed to stand ice-cold 20 h., and the precipitate washed with MeOH and water and purified by MeOH, yields 0.2-0.3 g. of 1-phenyl-3-phenylazo-4-cyano-5-methylpyrazole, PhN.N:C(N:NPh).C(CN):CMe, yellow, m. 130°, not hydrolyzed by prolonged heating in alc. KOH at 100°. Under the same conditions from I and BzCHNaCN, with final purification by glacial AcOH, is obtained 0.5 g. 1,5-diphenyl-3-phenylazo-4-cyanopyrazole, lustrous orange-yellow, m. 204-5°. A suspension of 2.58 g. I in anhydrous MeOH, poured into an equimol. weight of AcCHNaCOCH2OPh in anhydrous MeOH at 0° (energetic reaction), allowed to stand cold, and the precipitate purified by EtOH, yields 0.2 g. 1-phenyl-3-phenylazo-4-acetyl-5-(phenoxymethyl)pyrazole, peach, m. 168°. When heated with p-O2NC6H4NHNH2 (II) in 50% AcOH, it forms the p-nitrophenylhydrazone, C30H25O3N7, orange-red, m. 218-19°. In the same way, 2.58 g. I and Ac2CH2 yield, after purification by MeOH, 0.3-0.5 g. of 1-phenyl-3-phenylazo-4-acetyl-5-methylpyrazole (III), orange-yellow, m. 179°. With II in 50% AcOH, III gives a p-nitrophenylhydrazone, C24H21O2N7, orange-red, m. 222°; with semicarbazide, a semicarbazone, C19H19ON7, yellow, m. 193-4°. III (0.5 g.) and 50 cc. 40% HNO3, refluxed 30 min. (the mixture turns yellow, nitrous vapors are evolved, and a little resin is formed), cooled to 0°, the product washed with water, macerated with aqueous Na2CO3, the yellow solution decolorized, filtered, acidified with HCl, and the precipitate purified by dilute MeOH, yield 1-(p-nitrophenyl)-3-phenylazo-5-methyl-4-pyrazolecarboxylic acid, light brown-yellow, m. 205°. Hot III (0.5 g.) in 20 cc. 80% AcOH, treated with excess powd. Zn, the solution, when decolorized, dried in vacuo, the residue taken up in MeOH, filtered hot, cooled, and the precipitate purified rapidly by MeOH (the product tends to oxidize rapidly), yields 1-phenyl-3-phenylhydrazino-4-acetyl-5-methylpyrazole, m. approx. 170° (difficult to purify because of its great tendency to oxidize to III). III (2 g.) in 200 cc. MeOH, 1 g. Raney Ni, and several drops aqueous NaOH, treated with H under 3 atm. pressure until hydrogenation is complete (about 4 h.), filtered, acidified (Congo red) with concentrated HCl, concentrated to a small volume, distilled to dryness in vacuo, the residue taken up in 20 cc. water, water added successively until all the solid dissolves and then seps., filtered, and the residue purified by MeOH, yield 0.6 g. of 1-phenyl-3-amino-4-acetyl-5-methylpyrazole (IV), m. 195-6°. The aqueous solution, treated with NaOAc, increases the yield to a total of 0.7-0.8 g. Treatment of the aqueous solution with NaOH and steam distillation yield approx. 0.6 g. of PhNH2. IV is the 1st 3-aminopyrazole reported. It gives a p-nitrophenylhydrazone, C18H18O2N6, orange-red (from AcOH), m. 256° (decomposition). IV (0.05 g.) in 4 cc. 10% HCl and a small excess of solid NaNO2, kept ice-cold until clear and poured into excess alk. 2-naphthol, precipitates a dark red compound IV (0.1 g.) in 5 cc. 10% HCl, diazotized with NaNO2, the excess HNO2 eliminated with urea, 5 cc. concentrated HCl and a trace of CuCl added (N is evolved), boiled to complete the reaction, allowed to stand, and the precipitate purified by MeOH, yields 1-phenyl-3-chloro-4-acetyl-5-methylpyrazole, m. 67°. All these experiments show the well-defined aromaticity of 3-amino derivatives (V) of pyrazole and point to the existence of the IV form in the possible tautomeric equilibrium: IV ⇋ PhN.NH.C(:NH).CAc:CMe. Another method of preparing V more easily was studied, viz., by the action of diazo compounds on substituted malonic acids to form the corresponding formazyl ketones or aldehydes, according to the general reaction: RCOCH2CH-(CO2H)2 + 2ArN2X → RCOCH2C(:NNHAr)N:NAr (VI) + HX + CO2, and cyclization by mineral acids to the pyrazoles having the arylazo chain in the 3-position: VI H2O → ArN.N:C(N:NAr).CH:CR. However, all attempts to couple diazo compounds with (formylmethyl)- and acetonylmalonic acids gave only intractable pitches. But an aqueous suspension of 2.7 g. BzCH2CH(CO2H)2 in 18 cc., neutralized with NaHCO3, 12 g. NaOAc added, heated until dissolved, cooled to 0°, PhN2Cl (from 1.1 g. PhNH2, 4.8 cc. concentrated HCl, 20 cc. water, and 0.85 g. NaNO2) added, kept several hrs. at 0°, and the precipitate purified by dilute AcOH and EtOH, yields N,N’-diphenyl-C-phenacylformazan, BzCH2C(:NNHPh)N:NPh (VII), red, m. 110°. HCl, added to the mother liquor from the precipitation of VII, filtered, and the residue purified by EtOH and dried at 150°, yields PhN.CPh:CH.C(CO2H):N, m. 185° [cf. Ber. 20, 2185(1887)]. All attempts to cyclize VII under various conditions led to uncrystallizable pitches. Hence the method based on the use of formazyl halides remains the only one for the preparation of V.

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Reference:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem