Tag: 100-200

Mass spectra of the aminoisoquinolines and 5-amino-15N-isoquinoline was written by Brown, Ellis V.;Mitchell, Stanley R.. And the article was included in Organic Mass Spectrometry in 1972.HPLC of Formula: 23707-37-1 This article mentions the following:

The mass spectra of the isomeric aminoisoquinolines and 5-amino-15N-isoquinoline are reported. In the aminoisoquinolines, the major fragmentation pathway was the loss of 2 mols. of HCN and a H atom to give the m/e 89 fragment ion. Two addnl. pathways culminating with this ion were observed The mass spectrum of 5-amino-15N-isoquinoline showed a preference of 4 to 1 for loss of HC15N (benzenoid amine group) over HC14N (heterocyclic N) from the mol. ion. In the experiment, the researchers used many compounds, for example, Isoquinolin-7-amine (cas: 23707-37-1HPLC of Formula: 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. Most traditional methods of generating isoquinoline do so via oxidative aromatization of dihydro- or tetrahydro-isoquinolines, usually offering some environmental or economic advantage.HPLC of Formula: 23707-37-1

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Metal-, photocatalyst-, and light-free late-stage C-H alkylation of N-heteroarenes with organotrimethylsilanes using persulfate as a stoichiometric oxidant was written by Dong, Jianyang;Wang, Xiaochen;Wang, Zhen;Song, Hongjian;Liu, Yuxiu;Wang, Qingmin. And the article was included in Organic Chemistry Frontiers in 2019.HPLC of Formula: 36034-54-5 This article mentions the following:

Benzylsilanes and heteroatom substituted silanes underwent homolytic cleavage to form C(sp³)-centered radicals that can participate in C-H alkylation reactions with N-heteroarenes under oxidative conditions has been reported. These reactions take place under mild conditions with persulfate as a stoichiometric oxidant and do not require a metal, a photocatalyst, light, or high temperature, making the reactions suitable for late-stage C-H alkylation of complex mols. The utility of the method was demonstrated by the preparation or functionalization of several structurally complex drugs and natural products. In the experiment, the researchers used many compounds, for example, 4-Methoxyisoquinoline (cas: 36034-54-5HPLC of Formula: 36034-54-5).

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. Lewis acid activation and nucleophilic attack can produce multiple regioisomers in quinolines and pyridines; isoquinolines generally only undergo attack at the 1-position.HPLC of Formula: 36034-54-5

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Dihydroisoquinolinones: the design and synthesis of a new series of potent inhibitors of poly(ADP-ribose) polymerase was written by Suto, M. J.;Turner, W. R.;Arundel-Suto, C. M.;Werbel, L. M.;Sebolt-Leopold. And the article was included in Anti-Cancer Drug Design in 1991.Safety of 7-Nitro-3,4-dihydroisoquinolin-1(2H)-one This article mentions the following:

A series of dihydroisoquinolinones I(R = 5-, 6-, 7-, 8-OH, 5-, 6-, 7-OMe, 5-, 7-NO₂, 5-, 7-NH₂, H) and isoquinolinones II (R¹ = H, OH, OMe, NO₂, NH₂), formally rigid analogs of 3-substituted benzamides, and a series of disubstituted benzamides III (R² = H, Me; R³ = Me, Et, Pr, vinyl) were synthesized and evaluated as inhibitors of poly(ADP-ribose) polymerase. The results indicated that the orientation of the amide with respect to the substituent on the aromatic ring was critical for optimum inhibitory activity. Selected compounds were also evaluated for their ability to modify the radiation response of mammalian cells to ionizing radiation. A number of the 5-substituted I were very potent inhibitors of the enzyme, were able to enhance the lethal effects of ionizing radiation in mammalian cells, as measured by changes in the survival curve parameters D_o and/or D_q. In the experiment, the researchers used many compounds, for example, 7-Nitro-3,4-dihydroisoquinolin-1(2H)-one (cas: 22245-96-1Safety of 7-Nitro-3,4-dihydroisoquinolin-1(2H)-one).

7-Nitro-3,4-dihydroisoquinolin-1(2H)-one (cas: 22245-96-1) belongs to isoquinoline derivatives. Quinoline and its derivatives are widely used as fungicides, biological agents, antibiotics, alkaloids, dyes, rubber chemicals and flavoring agents. Other industrial applications include their use as corrosion inhibitors, preservatives, and as solvents for resins and terpenes.Safety of 7-Nitro-3,4-dihydroisoquinolin-1(2H)-one

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

1-(Dialkylaminoalkylamino)isoquinolines was written by Robinson, Richard A.. And the article was included in Journal of the American Chemical Society in 1947.Reference of 23707-37-1 This article mentions the following:

1-Chloroisoquinoline (I) (16.3 g.) and 35 g. Et₂N(CH₂)₃NH₂ heated 10 min. at 135-40°, the temperature raised to 175-80° during 25 min., and held at that point 10 min., give 88% 1-(3-diethylamino-propylamino)isoquinoline-2HCl, m. 125°. The following analogs were prepared similarly: 1-(1-diethylaminobutylamino), m. 90°, 85%; 1-(1-diethylamino-1-methylbutylamino), m. 95-100°, 80%; 1-(3-dibutylaminopropylamino) , m. 135°, 85%; 1-(3-dihexylaminopropylamino), m. 163°, 80%; 1-[3-(3-diethylaminopropylamino)propylamino](tri-HCl salt), m. 140°, 60%; 5-methoxy-1-(3-diethylaminopropylamino), m. 231°, 85%; 6-methoxy-1-(3-diethylaminopropylamino), m. 184°, 85%; 7-methoxy-1-(3-diethylaminopropylamino), m. 120°, 80%; 5-chloro-1-(3-diethylaminopropylamino) , m. 227°, 75%; 7-Cl isomer, m. 161°, 80%; 3-Cl isomer, m. 125°, 75%; 1-(7-diethyl-aminoheptylamino) (free base), oil, 80%. 6-Methoxy-tetrahydroisoquinoline (20 g.), 35 g. Raney Ni, and 200 g. C₁₀H₈, heated 1 hr. at 200 ± 5°, give 95% 6-methoxyisoquinoline (II), whose HCl salt m. 216°; picrate m. 225°. I (40 g.), added slowly to 0.328 mole perphthalic acid in 1300 ml. ether at -6 to -8°, the mixture stirred 90 min., kept overnight at 0°, the oily perphthalate washed with ether, and allowed to stand overnight at room temperature, gives 40% of the N-oxide (III), whose HCl salt m. 197°. With POCl₃ III yields 70% 6-methoxy-1-chloroisoquinoline, m. 77°. 7-Hydroxyisoquinoline by the Bucherer reaction yields 95% 7-aminoisoquinoline, m. 204°; through the diazo reaction it yields 75% 7-chloroisoquinoline (IV), m. 45°; 47 g. IV was added to a mixture of 41.14 g. 30% H₂O₂ and 200 ml. AcOH (after heating 1 hr. on the steam bath) and the solution heated 1 hr. on the steam bath to give 97% of the N-oxide (V), whose HCl salt m. 218°; with POCl₃ V yields 90% 1,7-dichloroisoquinoline, m. 138°. Fusion of Na 5-isoquinolinesulfonate with KOH at 220-30° (15 min.) gives 90% 1,5-dihydroxyisoquinoline, m. 282°; MeI yields 50% of the 5-methoxy-1-hydroxy derivative, m. 220°; POCl₃ gives 70% of the 5-Methoxy-1-chloro derivative, m. 137°. 7-Methoxyisoquinoline N-oxide with POCl₃ yields 75% of the 7-methoxy-1-chloro derivative, m. 176°. I and HNO₃ in H₂SO₄ at 5-8° give 80% 1-chloro-5-nitroisoquinoline, m. 187°; reduction over Raney Ni at 25°/3 atm. gives 75% of the 5-NH₂ derivative, m. 180°; the diazo reaction yields 50% 1,5-dichloroisoquinoline, m. 147°. In the experiment, the researchers used many compounds, for example, Isoquinolin-7-amine (cas: 23707-37-1Reference of 23707-37-1).

Isoquinolin-7-amine (cas: 23707-37-1) belongs to isoquinoline derivatives. Quinoline and isoquinoline skeletons are among the most attractive frameworks with a wide range of biological and pharmacological activities. Isoquinoline-type alkaloids show biological activities similar to those of morphinane-, protoberberine-, and benzophenanthridine-type alkaloids.Reference of 23707-37-1

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Design, Synthesis, and Structure-Activity Relationships of Highly Potent 5-HT₃ Receptor Ligands was written by Verheij, Mark H. P.;Thompson, Andrew J.;van Muijlwijk-Koezen, Jacqueline E.;Lummis, Sarah C. R.;Leurs, Rob;de Esch, Iwan J. P.. And the article was included in Journal of Medicinal Chemistry in 2012.Application In Synthesis of 3-Chloroisoquinolin-1-amine This article mentions the following:

Quinazoline and quinoline analogs of diazepanylquinazolinamine I, found as a hit fragment for inhibition of the serotonin 5-HT_3a receptor, were prepared and tested as ligands for the 5-HT_3a receptor. Several high affinity ligands were found, of which II showed the highest affinity (pK_i > 10) for the 5-HT₃ receptor. The observed structure-activity relationship is in agreement with established pharmacophore models for 5-HT₃ ligands and was used for ligand-receptor binding mode prediction using homol. modeling and in silico docking approaches. In the experiment, the researchers used many compounds, for example, 3-Chloroisoquinolin-1-amine (cas: 7574-67-6Application In Synthesis of 3-Chloroisoquinolin-1-amine).

3-Chloroisoquinolin-1-amine (cas: 7574-67-6) belongs to isoquinoline derivatives. Quinoline is a mancude organic heterobicyclic parent, an azaarene, an ortho-fused heteroarene and a member of isoquinolines. They are also used to make oil-soluble dyes, food colorants, pharmaceuticals, pH indicators and other organic compounds. Application In Synthesis of 3-Chloroisoquinolin-1-amine

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Discovery of novel P1 groups for coagulation factor VIIa inhibition using fragment-based screening was written by Cheney, Daniel L.;Bozarth, Jeffrey M.;Metzler, William J.;Morin, Paul E.;Mueller, Luciano;Newitt, John A.;Nirschl, Alexandra H.;Rendina, Alan R.;Tamura, James K.;Wei, Anzhi;Wen, Xiao;Wurtz, Nicholas R.;Seiffert, Dietmar A.;Wexler, Ruth R.;Priestley, E. Scott. And the article was included in Journal of Medicinal Chemistry in 2015.Category: isoquinoline This article mentions the following:

A multidisciplinary, fragment-based screening approach involving protein ensemble docking and biochem. and NMR assays is described. This approach led to the discovery of several structurally diverse, neutral surrogates for cationic factor VIIa P1 groups, which are generally associated with poor pharmacokinetic (PK) properties. Among the novel factor VIIa inhibitory fragments identified were aryl halides, lactams, and heterocycles. Crystallog. structures for several bound fragments were obtained, leading to the successful design of a potent factor VIIa inhibitor with a neutral lactam P1 and improved permeability. 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. Quinoline is a catabolite of tryptophan, the basic structure of some antihypertensive drugs, such as the peripheral vasodilators prazosin and doxazosin. Most traditional methods of generating isoquinoline do so via oxidative aromatization of dihydro- or tetrahydro-isoquinolines, usually offering some environmental or economic advantage.Category: isoquinoline

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Efficient nucleophilic substitution reactions of quinolyl and isoquinolyl halides with nucleophiles under focused microwave irradiation was written by Cherng, Yie-Jia. And the article was included in Tetrahedron in 2002.Application In Synthesis of 4-Methoxyisoquinoline This article mentions the following:

Nucleophilic substitution reactions of 2-chloroquinoline, 3-bromoquinoline and 4-bromoisoquinoline with thiolate, alkoxy ions and aniline were completed within several minutes under microwave irradiation This method gives the desired products with yields up to 99% in a short reaction time, and is superior to the classical heating process. In the experiment, the researchers used many compounds, for example, 4-Methoxyisoquinoline (cas: 36034-54-5Application In Synthesis of 4-Methoxyisoquinoline).

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. It protonates to form salts upon treatment with strong acids, such as HCl. It forms adducts with Lewis acids, such as BF3.Application In Synthesis of 4-Methoxyisoquinoline

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Discovery of 2-phenoxyacetamides as inhibitors of the Wnt-depalmitoleating enzyme NOTUM from an X-ray fragment screen was written by Atkinson, Benjamin N.;Steadman, David;Zhao, Yuguang;Sipthorp, James;Vecchia, Luca;Ruza, Reinis R.;Jeganathan, Fiona;Lines, Georgie;Frew, Sarah;Monaghan, Amy;Kjaer, Svend;Bictash, Magda;Jones, E. Yvonne;Fish, Paul V.. And the article was included in MedChemComm in 2019.Synthetic Route of C9H8N2 This article mentions the following:

NOTUM is a carboxylesterase that has been shown to act by mediating the O-depalmitoleoylation of Wnt proteins resulting in suppression of Wnt signaling. Here, we describe the development of NOTUM inhibitors that restore Wnt signaling for use in in vitro disease models where NOTUM over activity is an underlying cause. A crystallog. fragment screen with NOTUM identified 2-phenoxyacetamide 3 as binding in the palmitoleate pocket with modest inhibition activity (IC₅₀ 33 μM). Optimization of hit 3 by SAR studies guided by SBDD identified indazole 38 (IC₅₀ 0.032 μM) and isoquinoline 45 (IC₅₀ 0.085 μM) as potent inhibitors of NOTUM. The binding of 45 to NOTUM was rationalized through an X-ray co-crystal structure determination which showed a flipped binding orientation compared to 3. However, it was not possible to combine NOTUM inhibition activity with metabolic stability as the majority of the compounds tested were rapidly metabolized in an NADPH-independent manner. 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. Quinoline is a mancude organic heterobicyclic parent, an azaarene, an ortho-fused heteroarene and a member of isoquinolines. 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

Polyazanaphthalenes. VII. Some derivatives of quinazoline and 1,3,5-triazanaphthalene was written by Oakes, V.;Rydon, H. N.;Undheim, K.. And the article was included in Journal of the Chemical Society in 1962.Related Products of 7574-67-6 This article mentions the following:

2,4-Diamino-6-methylquinazoline was synthesized and converted, by side-chain bromination of its dibenzoyl derivative, condensation with ethyl p-aminobenzoatc, and removal of the benzoyl and ester groups, into the pteroic acid analog (I). A similar procedure has led to the successful synthesis of pteroic acid analogs derived from 2,4-diamino- and 2-amino-4-hydroxy-1,3,5-triazanaphthalene. The expected preferential reactivity of the 4-chlorine atom in 2,4-dichloro-6-methylquinazoline is exhibited in its reactions with ammonia, hydrazine, and benzylamine, but not in that with aniline. In the experiment, the researchers used many compounds, for example, 3-Chloroisoquinolin-1-amine (cas: 7574-67-6Related Products of 7574-67-6).

3-Chloroisoquinolin-1-amine (cas: 7574-67-6) belongs to isoquinoline derivatives. Although isoquinoline derivatives can be synthesized by several methods, relatively few direct methods deliver the unsubstituted isoquinoline. Isoquinoline-type alkaloids show biological activities similar to those of morphinane-, protoberberine-, and benzophenanthridine-type alkaloids.Related Products of 7574-67-6

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Design and synthesis of unique thiazoloisoquinolinium thiolates and derivatives was written by Ahmed, Wasim;Huang, Zi-Hao;Cui, Zi-Ning;Tang, Ri-Yuan. And the article was included in Chinese Chemical Letters in 2021.COA of Formula: C10H9NO This article mentions the following:

The synthesis of unique mesoionic thiazoloisoquinolinium thiolates stabilized by aromatization and 1,3-dipolarization. Herein, compounds were synthesized via the three component [2+2+1] cycloaddition reaction of isoquinolines with Et propionate and elemental sulfur in the absence of any metal catalyst and additives. Importantly, thiazoloisoquinolinium thiolates were transformed to thioether-containing thiazoloisoquinolinium halides. A selective [4+2] cycloaddition were also used to form S-bridged fused tetracyclic compounds with a thiothiamide ring unit and two quaternary carbon centers. Compound I showed good bioactivity against the chlorophyll of duckweed (Lemna minor) with inhibition rate of 51.5μg/mL. In the experiment, the researchers used many compounds, for example, 4-Methoxyisoquinoline (cas: 36034-54-5COA of Formula: C10H9NO).

4-Methoxyisoquinoline (cas: 36034-54-5) belongs to isoquinoline derivatives. Being an analog of pyridine, isoquinoline is a weak base, with a pKa of 5.14. It protonates to form salts upon treatment with strong acids, such as HCl. It forms adducts with Lewis acids, such as BF3.COA of Formula: C10H9NO

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem