Tag: 100-200

Discovery of 8-amino-substituted 2-phenyl-2,7-naphthyridinone derivatives as new c-Kit/VEGFR-2 kinase inhibitors was written by Sun, Haiyan;Zhuo, Linsheng;Dong, Huan;Huang, Wei;She, Nengfang. And the article was included in Molecules in 2019.Category: isoquinoline This article mentions the following:

The 2,7-naphthyridone scaffold has been proposed as a novel lead structure of MET inhibitors by our group. To broaden the application of this new scaffold, a series of 8-amino-substituted 2-phenyl-2,7-naphthyridin-1(2H)-one derivatives were designed and synthesized. Preliminary biol. screening resulted in the discovery of a new lead of c-Kit and VEGFR-2 kinase inhibitors. Compound 9k exhibited excellent c-Kit inhibitory activity, with an IC₅₀ value of 8.5 nM, i.e., it is 38.8-fold more potent than compound 3 (IC₅₀ of 329.6 nM). Moreover, the compounds 10l and 10r exhibited good VEGFR-2 inhibitory activity, with IC₅₀values of 56.5 and 31.7 nM, resp., i.e., they are 5.0-8.8-fold more potent than compound 3 (IC₅₀ of 279.9 nM). Mol. docking experiments provided further insight into the binding interactions of the new lead compounds with c-Kit and VEGFR-2 kinase. In this study, an 8-amino-substituted 2-phenyl-2,7-naphthyridin-1(2H)-one scaffold was identified as the new lead structure of c-Kit and VEGFR-2 kinase inhibitors. In the experiment, the researchers used many compounds, for example, Isoquinolin-7-amine (cas: 23707-37-1Category: isoquinoline).

Isoquinolin-7-amine (cas: 23707-37-1) belongs to isoquinoline derivatives. Quinoline is a catabolite of tryptophan, the basic structure of some antihypertensive drugs, such as the peripheral vasodilators prazosin and doxazosin. The Pomeranz–Fritsch reaction provides a method for the preparation of isoquinoline. This reaction uses a benzaldehyde and aminoacetoaldehyde diethyl acetal, which in an acid medium react to form isoquinoline.Category: isoquinoline

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Structure-Photochemical Function Relationships in Nitrogen-Containing Heterocyclic Aromatic Photobases Derived from Quinoline was written by Alamudun, Sophya F.;Tanovitz, Kyle;Fajardo, April;Johnson, Kaitlind;Pham, Andy;Jamshidi Araghi, Tina;Petit, Andrew S.. And the article was included in Journal of Physical Chemistry A in 2020.Recommanded Product: 23707-37-1 This article mentions the following:

Photobases are compounds that become strong bases after electronic excitation. Recent exptl. studies have highlighted the photobasicity of the 5-R quinoline compounds, demonstrating a strong substituent dependence to the pK_a^*. In this paper, we describe our systematic study of how the thermodn. driving force for photobasicity is tuned through substituents in four families of nitrogen-containing heterocyclic aromatics We show that substituent position and identity both significantly impact the pK_a^*. We demonstrate that the substituent effects are additive and identify many disubstituted compounds with substantially greater photobasicity than the most photobasic 5-R quinoline compound identified previously. We show that the addition of a second fused benzene ring to quinoline, along with two electron-donating substituents, lowers the S₀ â†?S_PBS vertical excitation energy into the visible region while still maintaining a pK_a^* > 14. Overall, the structure-function relationships developed in this study provide new insights to guide the development of new photocatalysts that employ photobasicity. In the experiment, the researchers used many compounds, for example, Isoquinolin-7-amine (cas: 23707-37-1Recommanded Product: 23707-37-1).

Isoquinolin-7-amine (cas: 23707-37-1) belongs to isoquinoline derivatives. Quinoline and its derivatives are widely used as fungicides, biological agents, antibiotics, alkaloids, dyes, rubber chemicals and flavoring agents. It protonates to form salts upon treatment with strong acids, such as HCl. It forms adducts with Lewis acids, such as BF3.Recommanded Product: 23707-37-1

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Beckmann rearrangements of 1-indanone oxime derivatives using aluminum chloride and mechanistic considerations was written by Lee, Byoung Se;Chu, Soyoung;Lee, In Young;Lee, Bon-Su;Song, Choong Eui;Chi, Dae Yoon. And the article was included in Bulletin of the Korean Chemical Society in 2000.Computed Properties of C9H8N2O3 This article mentions the following:

Hydrocarbostyril, which is a key intermediate in a new synthetic route to 6-nitroquipazine, can be prepared from 1-indanone oxime by Beckmann rearrangement. The reaction was optimized to 91% yield by using a Lewis acid, AlCl₃, instead of common acids such as polyphosphoric acid, and H₂SO₄ used in conventional Beckmann rearrangement (20% in the literature, 10% in the authors’ experiment). The optimized condition was established with 3 equiv AlCl₃ in CH₂Cl₂ at -40° to room temperature for 40 min. These conditions were applied to other 1-indanone derivatives, such as 4-methyl-, 4-methoxy- and 4- and 6-nitro-1-indanones. The mechanism of this reaction was proposed on the basis of the effect of temperature and substituent on product ratio, with the aid of PM3 calculation for a model system. In the experiment, the researchers used many compounds, for example, 7-Nitro-3,4-dihydroisoquinolin-1(2H)-one (cas: 22245-96-1Computed Properties of C9H8N2O3).

7-Nitro-3,4-dihydroisoquinolin-1(2H)-one (cas: 22245-96-1) belongs to isoquinoline derivatives. Although isoquinoline derivatives can be synthesized by several methods, relatively few direct methods deliver the unsubstituted isoquinoline. The Pomeranz–Fritsch reaction provides a method for the preparation of isoquinoline. This reaction uses a benzaldehyde and aminoacetoaldehyde diethyl acetal, which in an acid medium react to form isoquinoline.Computed Properties of C9H8N2O3

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Electronic properties of N-heteroaromatics. XXXIV. Fluorescence of isoquinoline derivatives, with special reference to solvent and external heavy atom effects was written by Okano, Teisuke;Matsumoto, Hitoshi. And the article was included in Yakugaku Zasshi in 1969.Computed Properties of C9H7ClN2 This article mentions the following:

Fluorescence spectra of isoquinoline derivatives were measured in various solvents in view of the solvent effect and the external heavy atom effect. The fluorescence of isoquinoline and its 1-cyano, 1-chloro, and 1-diacetylamino (m. 93-4°) derivatives was intensified in hydroxylic solvents, whereas the intensities of 1-amino-, 1-dimethylamino-(b5 124-6°), 1-methoxy-, and 3-aminoisoquinoline and of iso-carbostyril were independent of the solvent. The fluorescence intensification in hydroxylic solvents was attributed to the reversal of 1(π-π*) and 3(n-π*) levels caused by H bonding between the solute and the solvent, considering the intersystem crossing theory of El-Sayed (1963). The fluorescence of 1-aminoisoquinoline, its 3-chloro derivative, 1-chloro- and 2-methyl-3-aminoisoquinoline, and 3-aminoisocarbostyril in EtOH was quenched by addition of CCl4 or CBr4. Presumably, the external heavy atoms caused the spin-orbit coupling between the excited singlet and triplet states. In the experiment, the researchers used many compounds, for example, 3-Chloroisoquinolin-1-amine (cas: 7574-67-6Computed Properties of C9H7ClN2).

3-Chloroisoquinolin-1-amine (cas: 7574-67-6) belongs to isoquinoline derivatives. Quinoline and isoquinoline skeletons are among the most attractive frameworks with a wide range of biological and pharmacological activities. The Pomeranz–Fritsch reaction provides a method for the preparation of isoquinoline. This reaction uses a benzaldehyde and aminoacetoaldehyde diethyl acetal, which in an acid medium react to form isoquinoline.Computed Properties of C9H7ClN2

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

DMSO as a Switchable Alkylating Agent in Heteroarene C-H Functionalization was written by Garza-Sanchez, R. Aleyda;Patra, Tuhin;Tlahuext-Aca, Adrian;Strieth-Kalthoff, Felix;Glorius, Frank. And the article was included in Chemistry – A European Journal in 2018.Synthetic Route of C9H8N2 This article mentions the following:

A novel strategy for the activation of DMSO to act as a versatile alkylating agent in heteroarene C-H functionalization. This direct, simple and mild switch between methylation/trideuteromethylation and methylthiomethylation of heteroarenes was achieved under reagent-controlled photoredox catalysis conditions. The proposed mechanism was supported by both exptl. and computational studies. In the experiment, the researchers used many compounds, for example, Isoquinolin-7-amine (cas: 23707-37-1Synthetic Route of C9H8N2).

Isoquinolin-7-amine (cas: 23707-37-1) belongs to isoquinoline derivatives. Isoquinoline is a structural isomer of quinoline, which have antiseptic, antipyretic and anti-cyclic properties, and can be used as antimalarial drugs and for the preparation of other antimalarial medicine. They are also used to make oil-soluble dyes, food colorants, pharmaceuticals, pH indicators and other organic compounds. Synthetic Route of C9H8N2

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Mild and General Palladium-Catalyzed Synthesis of Methyl Aryl Ethers Enabled by the Use of a Palladacycle Precatalyst was written by Cheung, Chi Wai;Buchwald, Stephen L.. And the article was included in Organic Letters in 2013.Computed Properties of C10H9NO This article mentions the following:

A general method for the Pd-catalyzed coupling of methanol with (hetero)aryl halides is described. The reactions proceed under mild conditions with a wide range of aryl and heteroaryl halides to give Me aryl ethers in high yield. E.g., in presence of palladacycle precatalyst I (L = tBuBrettPhos) and the ligand tBuBrettPhos, arylation of MeOH by 4-Me₃CC₆H₄Cl gave 93% 4-Me₃CC₆H₄OMe. In the experiment, the researchers used many compounds, for example, 4-Methoxyisoquinoline (cas: 36034-54-5Computed Properties of C10H9NO).

4-Methoxyisoquinoline (cas: 36034-54-5) belongs to isoquinoline derivatives. Isoquinoline is a structural isomer of quinoline, which have antiseptic, antipyretic and anti-cyclic properties, and can be used as antimalarial drugs and for the preparation of other antimalarial medicine. The Pomeranz–Fritsch reaction provides a method for the preparation of isoquinoline. This reaction uses a benzaldehyde and aminoacetoaldehyde diethyl acetal, which in an acid medium react to form isoquinoline.Computed Properties of C10H9NO

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Syntheses of hydrogenated quinolines and isoquinolines as analgesics. X. Oxidation of alkylpyridines was written by Sugimoto, Norio;Kugita, Hiroshi;Tanaka, Tadashi. And the article was included in Yakugaku Zasshi in 1956.Application of 135311-97-6 This article mentions the following:

Oxidation of 2- (I), 3- (II) and 4-EtC₅H₄N (III) and the 1-oxides with CrO₃ effected oxidation in the order of II > III > I to the corresponding AcC₅H₄N in 50-15% yield. Oxidation of 15 g. 5,6,7,8-tetrahydroisoquinoline in 80 ml. AcOH and 30 g. concentrated H₂SO₄ at 10-5° with 16 g. CrO₃ in 9 ml. water and 45 ml. AcOH by keeping overnight, removing the AcOH in vacuo, alkalifying with NaOH and extracting with Et₂O yielded 8-oxo- (IV), b₄ 123-4°, and 5-oxo-5,6,7,8-tetrahydroisoquinoline (V), b₄ 113-15°, in 2:1 ratio; IV.HCl, m. 227-9°, and V.HCl, m. 235-6°. In the experiment, the researchers used many compounds, for example, 6,7-Dihydroisoquinolin-8(5H)-one hydrochloride (cas: 135311-97-6Application of 135311-97-6).

6,7-Dihydroisoquinolin-8(5H)-one hydrochloride (cas: 135311-97-6) belongs to isoquinoline derivatives. Quinoline is a catabolite of tryptophan, the basic structure of some antihypertensive drugs, such as the peripheral vasodilators prazosin and doxazosin. It protonates to form salts upon treatment with strong acids, such as HCl. It forms adducts with Lewis acids, such as BF3.Application of 135311-97-6

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Protonation Switching to the Least-Basic Heteroatom of Carbamate through Cationic Hydrogen Bonding Promotes the Formation of Isocyanate Cations was written by Kurouchi, Hiroaki;Sumita, Akinari;Otani, Yuko;Ohwada, Tomohiko. And the article was included in Chemistry – A European Journal in 2014.Category: isoquinoline This article mentions the following:

Ortho-(methoxycarbonyl)phenyl phenethylcarbamates underwent rapid cyclocondensation mediated by triflic acid to yield dihydroisoquinolinones with improved chemoselectivities over other phenethylcarbamates; the improved rate of cyclization is attributed to the improved formation of labile protonated carbamates and isocyanates, formed by protonation of the carbamate ester oxygen atom (rather than the carbamate carbonyl oxygen atom) mediated through hydrogen bonding to the pendant methoxycarbonyl group. The mechanism of the cyclocondensations of ortho-(methoxycarbonyl)phenyl phenethylcarbamates was studied through determination of the kinetics of other substituted phenethylcarbamates and of the dependence of cyclocondensation rate on acidity, through calculations of the transition state free energies, entropies, and enthalpies, and through NMR spectroscopy of models of mono- and diprotonated salicylates. Triflic acid-mediated monoprotonation of the carbamoyl salicylates yielded reactive protonated carbamates and isocyanates; in contrast, superacid-mediated diprotonation at the Me ester oxygen of the salicylate and the carbonyl oxygen of the carbamate afforded a rather stable dication, which did not readily undergo carbon-oxygen bond cleavage. In the experiment, the researchers used many compounds, for example, 7-Nitro-3,4-dihydroisoquinolin-1(2H)-one (cas: 22245-96-1Category: isoquinoline).

7-Nitro-3,4-dihydroisoquinolin-1(2H)-one (cas: 22245-96-1) belongs to isoquinoline derivatives. Isoquinoline is a structural isomer of quinoline, which have antiseptic, antipyretic and anti-cyclic properties, and can be used as antimalarial drugs and for the preparation of other antimalarial medicine. Lewis acid activation and nucleophilic attack can produce multiple regioisomers in quinolines and pyridines; isoquinolines generally only undergo attack at the 1-position.Category: isoquinoline

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Substituent effect on local aromaticity in mono and di-substituted heterocyclic analogs of naphthalene was written by Mohajeri, Afshan;Shahamirian, Mozhgan. And the article was included in Journal of Physical Organic Chemistry in 2010.Synthetic Route of C10H9NO This article mentions the following:

A quant. study on local aromaticity has been performed on a series of mono- and di-substituted biheterocycles (quinoline, isoquinoline, quinoxaline, quinazoline). Three electronically based indexes (PDI, ATI, and FLU) have been employed to investigate the substituent effect on the π-electron delocalization in both heterocycle and benzenoid rings. Three typical substituents (Cl, OCH₃, and CN) with different inductive and resonance power have been selected. Generally, substituent causes a reduction in aromaticity irresp. of whether it is electron attracting or electron donating. It is shown that the maximum aromaticity exhibits a similar trend of Cl > CN > OCH₃ for all the studied rings. Moreover, it is found that the substituent situation with respect to the heteroatom has a significant influence on the aromaticity. It results from our study that in di-substituted derivatives, irresp. of whether the two substituents form a meta or para isomer, they preferably choose the position which leads to the maximum aromaticity character. Copyright © 2009 John Wiley & Sons, Ltd. In the experiment, the researchers used many compounds, for example, 4-Methoxyisoquinoline (cas: 36034-54-5Synthetic Route of C10H9NO).

4-Methoxyisoquinoline (cas: 36034-54-5) belongs to isoquinoline derivatives. Quinoline and isoquinoline skeletons are among the most attractive frameworks with a wide range of biological and pharmacological activities. The discovery of chloroquine, the most well-known drug containing this stent, has helped bring about decades of malaria control and treatment.Synthetic Route of C10H9NO

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

The imidazo[1,2-a]pyridine ring system as a scaffold for potent dual phosphoinositide-3-kinase (PI3K)/mammalian target of rapamycin (mTOR) inhibitors was written by Stec, Markian M.;Andrews, Kristin L.;Bo, Yunxin;Caenepeel, Sean;Liao, Hongyu;McCarter, John;Mullady, Erin L.;San Miguel, Tisha;Subramanian, Raju;Tamayo, Nuria;Whittington, Douglas A.;Wang, Ling;Wu, Tian;Zalameda, Leeanne P.;Zhang, Nancy;Hughes, Paul E.;Norman, Mark H.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2015.Related Products of 23707-37-1 This article mentions the following:

Based on lead compound, which was discovered from a high-throughput screen, a series of PI3Kα/mTOR inhibitors were evaluated that contained an imidazo[1,2-a]pyridine as a core replacement for the benzimidazole contained in the lead. By exploring various ring systems that occupy the affinity pocket, two fragments containing a methoxypyridine were identified that gave <100 nM potency toward PI3Kα in enzyme and cellular assays with moderate stability in rat and human liver microsomes. With the two methoxypyridine groups selected to occupy the affinity pocket, analogs were prepared with various fragments intended to occupy the ribose pocket of PI3Kα and mTOR. From these analogs, tertiary alc. I was chosen for in vivo pharmacodynamic evaluation based on its potency in the PI3Kα cellular assay, microsomal stability, and in vivo pharmacokinetic properties. In a mouse liver pharmacodynamic assay, compound I showed 56% inhibition of HFG-induced AKT (Ser473) phosphorylation at a 30 mg/kg dose. In the experiment, the researchers used many compounds, for example, Isoquinolin-7-amine (cas: 23707-37-1Related Products of 23707-37-1).

Isoquinolin-7-amine (cas: 23707-37-1) belongs to isoquinoline derivatives. Isoquinoline is a structural isomer of quinoline, which have antiseptic, antipyretic and anti-cyclic properties, and can be used as antimalarial drugs and for the preparation of other antimalarial medicine. They are also used to make oil-soluble dyes, food colorants, pharmaceuticals, pH indicators and other organic compounds. Related Products of 23707-37-1

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem