Category: isoquinoline

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

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

Fragment-based lead discovery of indazole-based compounds as AXL kinase inhibitors was written by Ng, Pearly Shuyi;Foo, Klement;Sim, Sandra;Wang, Gang;Huang, Chuhui;Tan, Li Hong;Poulsen, Anders;Liu, Boping;Tee, Doris Hui Ying;Ahmad, Nur Huda Binte;Wang, Sifang;Ke, Zhiyuan;Lee, May Ann;Kwek, Zekui P.;Joy, Joma;Anantharajan, Jothi;Baburajendran, Nithya;Pendharkar, Vishal;Manoharan, Vithya;Vuddagiri, Susmitha;Sangthongpitag, Kanda;Hill, Jeffrey;Keller, Thomas H.;Hung, Alvin W.. And the article was included in Bioorganic & Medicinal Chemistry in 2021.Reference of 90721-35-0 This article mentions the following:

AXL is a member of the TAM (TYRO3, AXL, MER) subfamily of receptor tyrosine kinases. It is upregulated in a variety of cancers and its overexpression is associated with poor disease prognosis and acquired drug resistance. Utilizing a fragment-based lead discovery approach, a new indazole-based AXL inhibitor was obtained. The indazole fragment hit 11, identified through a high concentration biochem. screen, was expeditiously improved to fragment 24 by screening our inhouse expanded library of fragments (ELF) collection. Subsequent fragment optimization guided by docking studies provided potent inhibitor 54 with moderate exposure levels in mice. X-ray crystal structure of analog 50 complexed with the I650M mutated kinase domain of Mer revealed the key binding interactions for the scaffold. The good potency coupled with reasonable kinase selectivity, moderate in vivo exposure levels, and availability of structural information for the series makes it a suitable starting point for further optimization efforts. In the experiment, the researchers used many compounds, for example, 5-Bromoisoquinolin-8-amine (cas: 90721-35-0Reference of 90721-35-0).

5-Bromoisoquinolin-8-amine (cas: 90721-35-0) 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.Reference of 90721-35-0

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Use of High-Throughput Tools for Telescoped Continuous Flow Synthesis of an Alkynylnaphthyridine Anticancer Agent, HSN608 was written by Biyani, Shruti A.;Qi, Qingqing;Wu, Jingze;Moriuchi, Yuta;Larocque, Elizabeth A.;Sintim, Herman O.;Thompson, David H.. And the article was included in Organic Process Research & Development in 2020.Safety of 5-Bromoisoquinolin-8-amine This article mentions the following:

Developing continuous syntheses of lead compounds to support in vivo studies and preclin. evaluation remains an underdeveloped area. We report a telescoped continuous flow synthesis of an alkynylnaphthyridine lead compound for the treatment of FLT3 mutations in acute myeloid leukemia. Different strategies were used to develop the route, including Design of Experiments (DoE), high-throughput experimentation (HTE), and application of desorption electrospray ionization mass spectrometry (DESI-MS) to optimize and telescope the amidation and Sonogashira couplings to prepare the target compound, HSN608 (I), a potent FLT3 inhibitor. Findings from these statistical design and automation studies helped streamline our workflow to achieve 10-fold and 5-fold reductions in the catalyst and cocatalyst loadings, resp., in the synthesis. The application of high-throughput tools combined with a telescoped continuous synthesis method enabled an efficient and safe synthesis of this lead compound using the hazardous coupling reagent HATU while minimizing byproduct formation. In the experiment, the researchers used many compounds, for example, 5-Bromoisoquinolin-8-amine (cas: 90721-35-0Safety of 5-Bromoisoquinolin-8-amine).

5-Bromoisoquinolin-8-amine (cas: 90721-35-0) 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.Safety of 5-Bromoisoquinolin-8-amine

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