6-甲基吡唑并[1,5-a]吡啶-3-羧酸乙酯 | 55899-18-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并吡啶类
• 中文名称: 6-甲基吡唑并[1,5-a]吡啶-3-羧酸乙酯
• 英文名称: ethyl 6-methylpyrazolo[1,5-a]pyridine-3-carboxylate
• 英文别名: 6-methyl-pyrazolo[1,5-a]pyridine-3-carboxylic acid ethyl ester
• CAS: 55899-18-8
• 化学式: C₁₁H₁₂N₂O₂
• 分子量: 204.228
• InChiKey: ZAQSZHNYRCSHOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-甲基吡唑并[1,5-a]吡啶-3-羧酸乙酯 在 N,N'-羰基二咪唑 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 24.5h， 生成 (6-methylpyrazolo[1,5-a]pyridin-3-yl)methanol
  参考文献：
  名称：

  Discovery of pyrazolo[1,5-a]pyridines as p110α-selective PI3 kinase inhibitors

  摘要：

  We have made a novel series of pyrazolo[1,5-a]pyridines as PI3 kinase inhibitors, and demonstrated their selectivity for the p110 alpha isoform over the other Class Ia PI3 kinases. We investigated the SAR around the pyrazolo[1,5-a] pyridine ring system, and found compound 5x to be a particularly potent example (p110 alpha IC50 0.9 nM). This compound inhibits cell proliferation and phosphorylation of Akt/PKB, a downstream marker of PI3 kinase activity, and showed in vivo activity in an HCT-116 human xenograft model. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.029
• 作为产物：
  描述：

  3-methyl-N-aminopyridinium mesitylenesulfonate 、 丙炔酸乙酯 以16%的产率得到
  参考文献：
  名称：

  TAMURA Y.; SUMIDA Y.; MIKI Y.; IKEDA M., J. CHEM. SOC. PERKIN TRANS , 1975, PART 1, NO 5, 406-409

  摘要：

  DOI：

文献信息

• [EN] IMIDAZO [1, 2 -A] PYRIDINE AND PYRAZOLO [1, 5 -A] PYRIDINE DERIVATIVES AS TRPV1 ANTAGONISTS<br/>[FR] DÉRIVÉS D'IMIDAZO[1,2-A]PYRIDINE ET DE PYRAZOLO[1,5-A]PYRIDINE EN TANT QU'ANTAGONISTES DU TRPV1
  申请人：GLAXO GROUP LTD

  公开号：WO2012045729A1

  公开（公告）日：2012-04-12

  A compound of formula of formula (I) wherein A represents a single bond, a CH2 group or a CH (Me) group; X1 represents a hydrogen atom, a fluorine atom or a methyl group; X2 represents a hydrogen atom, a fluorine atom, a methyl group or a CH2OH group; X3 represents a hydrogen atom, a fluorine atom or a CH2OH group, and at least two of X1, X2 and X3 are hydrogen; Y represents a C atom and Z represents a N atom or Y represents an N atom and Z represents a C atom. R1 represents a halogen atom, a C1-4 alkyl group, a trifluoromethyl group or a trifluoromethoxy group, and R2 and R3 are each independently selected from a hydrogen atom, a halogen atom, a C1-4 alkyl group, a trifluoromethyl group or a trifluoromethoxy group. or a pharmaceutically acceptable salt or solvate thereof. salt or solvate thereof.

  化合物的化学式为（I），其中A代表一个单键，一个CH2基团或一个CH（Me）基团；X1代表一个氢原子，一个氟原子或一个甲基基团；X2代表一个氢原子，一个氟原子，一个甲基基团或一个CH2OH基团；X3代表一个氢原子，一个氟原子或一个CH2OH基团，且至少两个X1、X2和X3中有两个是氢；Y代表一个碳原子，Z代表一个氮原子，或Y代表一个氮原子，Z代表一个碳原子。R1代表一个卤素原子，一个C1-4烷基基团，一个三氟甲基基团或一个三氟甲氧基团，R2和R3分别独立选择自一个氢原子，一个卤素原子，一个C1-4烷基基团，一个三氟甲基基团或一个三氟甲氧基团，或其药用可接受的盐或溶剂。
• PHTHALAZINONES AND ISOQUINOLINONES AS ROCK INHIBITORS
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US20150353505A1

  公开（公告）日：2015-12-10

  The present invention provides compounds of Formula (I) or stereoisomers, tautomers, or pharmaceutically acceptable salts thereof, wherein all the variables are as defined herein. These compounds are selective ROCK inhibitors. This invention also relates to pharmaceutical compositions comprising these compounds and methods of treating cardiovascular, smooth muscle, oncologic, neuropathologic, autoimmune, fibrotic, and/or inflammatory disorders using the same.

  本发明提供了公式（I）的化合物或其立体异构体，互变异构体或药学上可接受的盐，其中所有变量如此定义。这些化合物是选择性ROCK抑制剂。本发明还涉及包含这些化合物的制药组合物以及使用它们治疗心血管，平滑肌，肿瘤，神经病理，自身免疫，纤维化和/或炎症性疾病的方法。
• Benzimidazolone as potent chymase inhibitor: Modulation of reactive metabolite formation in the hydrophobic (P1) region
  作者：Ho Yin Lo、Peter A. Nemoto、Jin Mi Kim、Ming-Hong Hao、Kevin C. Qian、Neil A. Farrow、Daniel R. Albaugh、Danielle M. Fowler、Richard D. Schneiderman、E. Michael August、Leslie Martin、Melissa Hill-Drzewi、Steven S. Pullen、Hidenori Takahashi、Stéphane De Lombaert

  DOI：10.1016/j.bmcl.2011.05.126

  日期：2011.8

  A new class of chymase inhibitor featuring a benzimidazolone core with an acid side chain and a P-1 hydrophobic moiety is described. Incubation of the lead compound with GSH resulted in the formation of a GSH conjugate on the benzothiophene P-1 moiety. Replacement of the benzothiophene with different heterocyclic systems such as indoles and benzoisothiazole is feasible. Among the P-1 replacements, benzoisothiazole prevents the formation of GSH conjugate and an in silico analysis of oxidative potentials agreed with the experimental outcome. (C) 2011 Elsevier Ltd. All rights reserved.
• US9926282B2
  申请人：——

  公开号：US9926282B2

  公开（公告）日：2018-03-27
• Discovery of pyrazolo[1,5-a]pyridines as p110α-selective PI3 kinase inhibitors
  作者：Jackie D. Kendall、Patrick D. O’Connor、Andrew J. Marshall、Raphaël Frédérick、Elaine S. Marshall、Claire L. Lill、Woo-Jeong Lee、Sharada Kolekar、Mindy Chao、Alisha Malik、Shuqiao Yu、Claire Chaussade、Christina Buchanan、Gordon W. Rewcastle、Bruce C. Baguley、Jack U. Flanagan、Stephen M.F. Jamieson、William A. Denny、Peter R. Shepherd

  DOI：10.1016/j.bmc.2011.11.029

  日期：2012.1

  We have made a novel series of pyrazolo[1,5-a]pyridines as PI3 kinase inhibitors, and demonstrated their selectivity for the p110 alpha isoform over the other Class Ia PI3 kinases. We investigated the SAR around the pyrazolo[1,5-a] pyridine ring system, and found compound 5x to be a particularly potent example (p110 alpha IC50 0.9 nM). This compound inhibits cell proliferation and phosphorylation of Akt/PKB, a downstream marker of PI3 kinase activity, and showed in vivo activity in an HCT-116 human xenograft model. (C) 2011 Elsevier Ltd. All rights reserved.