Tag: 100-200

Development of a Scalable Synthesis of a VEGFR Inhibitor was written by Chen, Ying;Crockett, Richard D.;Wang, Xin;Larsen, Robert D.;Cui, Sheng;Faul, Margaret M.. And the article was included in Synlett in 2013.Safety of Isoquinolin-7-amine This article mentions the following:

Process development and salt selection for a novel -VEGFR inhibitor are described. The overall convergent synthesis involved coupling of three key fragments, 2-chloronicotinoyl chloride, 4-isopropyl-3-methylaniline and 7-aminoisoquinoline. A cost-effective and scalable synthesis of 7-aminoisoquinoline was also achieved. A transition-metal-free SNAr process enabled the final C-N coupling to afford the target mol. A phosphate form of the drug substance with improved phys. properties was selected for further development and the corresponding crystallization process was subsequently developed. Overall, a robust six-step route was developed and demonstrated on multikilogram scales affording the target compound in >30% yield and high purity (>99%). In the experiment, the researchers used many compounds, for example, Isoquinolin-7-amine (cas: 23707-37-1Safety of Isoquinolin-7-amine).

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. Isoquinoline-type alkaloids show biological activities similar to those of morphinane-, protoberberine-, and benzophenanthridine-type alkaloids.Safety of Isoquinolin-7-amine

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

6,6-Fused heterocyclic ureas as highly potent TRPV1 antagonists was written by Sun, Wei;Kim, Hyo-Shin;Lee, Sunho;Jung, Aeran;Kim, Sung-Eun;Ann, Jihyae;Yoon, Suyoung;Sun, Choi;Lee, Jin Hee;Blumberg, Peter M.;Frank-Foltyn, Robert;Bahrenberg, Gregor;Schiene, Klaus;Stockhausen, Hannelore;Christoph, Thomas;Frormann, Sven;Lee, Jeewoo. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2015.Related Products of 23707-37-1 This article mentions the following:

A series of N-[{2-(4-methylpiperidin-1-yl)-6-(trifluoromethyl)-pyridin-3-yl}methyl] N’-(6,6-fused heterocyclic) ureas have been investigated as hTRPV1 antagonists. Among them, compound (I) showed highly potent TRPV1 antagonism to capsaicin, with K_i(ant) = 0.2 nM, as well as antagonism to other activators, and it was efficacious in a pain model. A docking study of I with our hTRPV1 homol. model indicates that there is crucial hydrogen bonding between the ring nitrogen and the receptor, contributing to its potency. 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. The isoquinoline structure occurs in a considerable number of alkaloids in widely separated plant families. 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.Related Products of 23707-37-1

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Discovery of hydroxy pyrimidine Factor IXa inhibitors was written by Jayne, Charles L.;Andreani, Teresa;Chan, Tin-Yau;Chelliah, Mariappan V.;Clasby, Martin C.;Dwyer, Michael;Eagen, Keith A.;Fried, Steve;Greenlee, William J.;Guo, Zhuyan;Hawes, Brian;Hruza, Alan;Ingram, Richard;Keertikar, Kartik M.;Neelamkavil, Santhosh;Reichert, Paul;Xia, Yan;Chackalamannil, Samuel. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2020.Category: isoquinoline This article mentions the following:

The synthesis and structure activity relationship development of a pyrimidine series of heterocyclic Factor IXa inhibitors, I and II [R = Q, Q¹, Q², etc.], is described. Increased selectivity over Factor Xa inhibition was achieved through SAR expansion of the P1 element. Select compounds were evaluated in vivo to assess their plasma levels in rat. 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 mancude organic heterobicyclic parent, an azaarene, an ortho-fused heteroarene and a member of isoquinolines. 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

Construction of key building blocks towards the synthesis of cortistatins was written by Indu, Satrajit;Telore, Rahul D.;Kaliappan, Krishna P.. And the article was included in Organic & Biomolecular Chemistry in 2020.Recommanded Product: 23707-37-1 This article mentions the following:

This work reports the construction of key building blocks towards the synthesis of cortistatins, a family of steroidal alkaloids. Cortistatin A (I), being a primary target due to its superior biol. properties over other congeners, has been prepared by two different synthetic routes. Synthesis of the precursor to the heavily substituted A-ring starting from D-glucose and construction of the DE-ring junction employing a Hajos-Parrish ketone as a chiral pool have been demonstrated. Efforts are underway to assemble these key fragments and build towards the total synthesis of cortistatin A. 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 is a catabolite of tryptophan, the basic structure of some antihypertensive drugs, such as the peripheral vasodilators prazosin and doxazosin. Lewis acid activation and nucleophilic attack can produce multiple regioisomers in quinolines and pyridines; isoquinolines generally only undergo attack at the 1-position.Recommanded Product: 23707-37-1

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Practical and Asymmetric Reductive Coupling of Isoquinolines Templated by Chiral Diborons was written by Chen, Dongping;Xu, Guangqing;Zhou, Qinghai;Chung, Lung Wa;Tang, Wenjun. And the article was included in Journal of the American Chemical Society in 2017.Reference of 36034-54-5 This article mentions the following:

We herein describe a chiral diboron-templated highly diastereoselective and enantioselective reductive coupling of isoquinolines that provided expedited access to a series of chiral substituted bisisoquinolines, e. g., I, in good yields and excellent ee’s under mild conditions. The method enjoys a broad substrate scope and good functional group compatibility. Mechanistic investigation suggests the reaction proceeds through a concerted [3,3]-sigmatropic rearrangement. In the experiment, the researchers used many compounds, for example, 4-Methoxyisoquinoline (cas: 36034-54-5Reference of 36034-54-5).

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. They are also used to make oil-soluble dyes, food colorants, pharmaceuticals, pH indicators and other organic compounds. Reference of 36034-54-5

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Structure-Activity Relationship for Small Molecule Inhibitors of Nicotinamide N-Methyltransferase was written by Neelakantan, Harshini;Wang, Hua-Yu;Vance, Virginia;Hommel, Jonathan D.;McHardy, Stanton F.;Watowich, Stanley J.. And the article was included in Journal of Medicinal Chemistry in 2017.Safety of Isoquinolin-7-amine This article mentions the following:

Nicotinamide N-methyltransferase (NNMT) is a fundamental cytosolic biotransforming enzyme that catalyzes the N-methylation of endogenous and exogenous xenobiotics. We have identified small mol. inhibitors of NNMT with >1000-fold range of activity and developed comprehensive structure-activity relationships (SARs) for NNMT inhibitors. Screening of N-methylated quinolinium, isoquinolinium, pyrididium, and benzimidazolium/benzothiazolium analogs resulted in the identification of quinoliniums as a promising scaffold with very low micromolar (IC₅₀ âˆ?1 μM) NNMT inhibition. Computer-based docking of inhibitors to the NNMT substrate (nicotinamide)-binding site produced a robust correlation between ligand-enzyme interaction docking scores and exptl. calculated IC₅₀ values. Predicted binding orientation of the quinolinium analogs revealed selective binding to the NNMT substrate-binding site residues and essential chem. features driving protein-ligand intermol. interactions and NNMT inhibition. The development of this new series of small mol. NNMT inhibitors direct the future design of lead drug-like inhibitors to treat several metabolic and chronic disease conditions characterized by abnormal NNMT activity. In the experiment, the researchers used many compounds, for example, Isoquinolin-7-amine (cas: 23707-37-1Safety of Isoquinolin-7-amine).

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 discovery of chloroquine, the most well-known drug containing this stent, has helped bring about decades of malaria control and treatment.Safety of Isoquinolin-7-amine

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Extension of some quinolines and isoquinolines by a pyridine ring was written by Mlochowski, Jacek;Sliwa, Wanda;Achremowicz, Lucjan. And the article was included in Roczniki Chemii in 1974.Related Products of 23707-37-1 This article mentions the following:

Skraup synthesis with aminoquinolines and aminoisoquinolines was used to prepare 1,5-, 1,6-, 1,9-, 2,7-, 4,5-, and 4,6-diazaphenanthrenes in 10-58% yields. 2-Methyl-4-hydroxy-1,5- and 8-methyl-10-hydroxy-2,7-diazaphenanthrenes were also prepared in 47 and 79% yield, resp., by the procedure of Conrad-Limpach. Angular products were formed in all cases. 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. The isoquinoline structure occurs in a considerable number of alkaloids in widely separated plant families. Lewis acid activation and nucleophilic attack can produce multiple regioisomers in quinolines and pyridines; isoquinolines generally only undergo attack at the 1-position.Related Products of 23707-37-1

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

An efficient and facile strategy for trifluoromethylation and perfluoroalkylation of isoquinolines and heteroarenes was written by Pan, Yang;Li, Jiangtao;Li, Zhefeng;Huang, Feng;Ma, Xiaofeng;Jiao, Wei;Shao, Huawu. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2020.Name: 4-Methoxyisoquinoline This article mentions the following:

An effective and regioselective strategy for trifluoromethylation and perfluoroalkylation of isoquinolines I (R¹ = OMe, Ph, Br, etc.; R² = H, formyl, OMe, NO₂; R³ = Me, 2-phenylethynyl, Cl, etc.; R⁴ = H, OMe; R⁵ = H, Ph, Br) and heteroarenes R⁶H (R⁶ = phenanthridin-6-yl, thieno[2,3-c]pyridin-7-yl, quinazolin-2-yl, etc.) was developed. By combination of TMSC_nF_2n+1 (n = 1, 2, 3) with PIFA, the method achieved the corresponding perfluoroalkylated products R⁶C_nF_2n+1 (n = 1, 2, 3) with broad functional group tolerance. In the experiment, the researchers used many compounds, for example, 4-Methoxyisoquinoline (cas: 36034-54-5Name: 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. 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.Name: 4-Methoxyisoquinoline

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Synthesis of some isoquinolines was written by Manske, Richard H. F.;Kulka, Marshall. And the article was included in Canadian Journal of Research, Section B: Chemical Sciences in 1949.Recommanded Product: 23707-37-1 This article mentions the following:

5-Chloroisoquinoline (I), m. 73-4° (all m. ps. corrected) (60% yield), and the 7-isomer (II) (cf. Robinson, C.A. 41, 6886h) (perchlorate, m. 163-4°) were prepared by the Sandmeyer reaction from the 5-NH₂ compound (III) (cf. Misani and Bogert, C.A. 40, 1845.8) and the 7-NH₂ compound (IV) (cf. R., loc. cit.), resp. The Ac derivative (V) of IV m. 147-8°; hydrate m. 103-4°. A better yield of IV was obtained when the Schiff base (cf. Woodward and Doering, C.A. 39, 3002.3) was purified before cyclization. The diazotized III and IV, reduced with SnCl₂, yielded 51% 5-and 50% of the 7-NH₂NH compound, m. 165-7° and 158-60°. m-ClC₆H₄CHO and NH₂CH₂CH-(OEt)₂ (VI) (25 g. each), heated on the steam bath 0.5 hr. and distilled, yielded 86% of the Schiff base, b₁₁ 170°. The ring was closed with H₂SO₄ and P₂O₅ (cf. Tyson, C.A. 33, 1736.9); the yield of mixed I and II was 38%. Nitration of I and II yielded 87% of the 5-VII and 86% of the 7-chloro-8-nitro compound (VIII), m. 134-5° and 146-7°. VII and VIII with SnCl₂ in concentrated HCl yielded 75% of the 5- and 55% of the 7-chloro-8-amino compound, m. 204-5° and 171-2° VII and VIII with alc. NH₃ yielded the 5-(IX) and the 7-amino-8-nitro compound (X), m. 265-8° (decomposition) (Ac derivative, m. 225-7°) and 246-7° (65% yield). Deamination of the diazotized X with H₃PO₂ yielded 8-chloroisoquinoline (XI) (cf. Keilin and Cass, C.A. 37, 129.3). Reduction of diazotized IX and X yielded 80% of the 8-hydrazino-5-chloro and 56% of the 7-hydrazino-8-chloro compound, m. 192-3° (decomposition) and 176-8°. Chlorination of V (1 g.) yielded 0.7 g. of the 7-acetamido-8-chloro compound (XII), m. 166-7°. XII (0.5 g.) yielded 0.40 g. of the 7-amino-8-chloro compound (XIII), m. 177-9°. Deamination of XIII gave XI. VI and 2,3-Cl(HO)C₆H₃CHO (15 g. each) were heated 0.5 hr. on the steam bath, dried by repeated C₆H₆ distillations, the ring closed with 76% H₂SO₄ at 0°, the mixture stirred 4 hrs. at 2-5°, allowed to stand 40 hrs. at 8°, and 30 hrs. at room temperature, dissolved in H₂O, NH₄OH and Na₂CO₃ added, and the precipitate filtered and sublimed at 175° (1 mm.) to yield 64% of the 7-hydroxy-8-chloro compound (XIV), m. 230-1°. The Bucherer reaction yielded IV, m. 203-4°, with XIV. 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. The isoquinoline structure occurs in a considerable number of alkaloids in widely separated plant families. Isoquinoline-type alkaloids show biological activities similar to those of morphinane-, protoberberine-, and benzophenanthridine-type alkaloids.Recommanded Product: 23707-37-1

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Investigations in the field of the bimolecular alkylidene-arylamines. IV. Structure of the bromination product of the diacetyl derivative of trans-2-methyl-4-anilino-1,2,3,4-tetrahydroquinoline was written by Zalukajvs, L.. And the article was included in Latvijas PSR Zinatnu Akademijas Vestis in 1956.Product Details of 135311-97-6 This article mentions the following:

In order to prove that the bimol. ethylideneaniline is not a trans-1,3-dianilino-1-butene, as stated by Eibner [Ann. 318, 58 (1901)], but trans-2-methyl-4-anilino-1,2,3,4-tetrahydroquinoline (I), the product was acetylated, brominated, and finally hydrolyzed. Acetylating I, m. 126°, yielded the diacetyl derivative (II) in 68% yield, m. 187-8° (from EtOH). Monobromination of 12.8 g. II gave 6.5 g. colorless monobromo derivative (III), m. 156° (from EtOH). Hydrolysis of III by boiling 50% H₂SO₄ led to the 6-bromoquinaldine, m. 100-1°, which gave no depression when mixed with an authentic sample obtained from p-bromoaniline and paraldehyde. If the bimol. ethylideneaniline had the structure proposed by Eibner, the transformations above would have led to the quinaldine or its 3- or 4-monobromo derivative 8 references. In the experiment, the researchers used many compounds, for example, 6,7-Dihydroisoquinolin-8(5H)-one hydrochloride (cas: 135311-97-6Product Details of 135311-97-6).

6,7-Dihydroisoquinolin-8(5H)-one hydrochloride (cas: 135311-97-6) belongs to isoquinoline derivatives. Quinoline and its derivatives are widely used as fungicides, biological agents, antibiotics, alkaloids, dyes, rubber chemicals and flavoring agents. Isoquinoline-type alkaloids show biological activities similar to those of morphinane-, protoberberine-, and benzophenanthridine-type alkaloids.Product Details of 135311-97-6

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem