3-溴-1H-吲唑-7-羧酸 | 1040101-01-6

• 物质功能分类: 医药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 中文名称: 3-溴-1H-吲唑-7-羧酸
• 中文别名: 3-溴-1H-7-羧酸吲唑
• 英文名称: 3-Bromo-1H-indazole-7-carboxylic acid
• 英文别名: 3-bromo-2H-indazole-7-carboxylic acid
• CAS: 1040101-01-6
• 化学式: C₈H₅BrN₂O₂
• 分子量: 241.044
• InChiKey: SHOGUOJFKMABOH-UHFFFAOYSA-N

物化性质

• 沸点：
  493.4±25.0 °C(Predicted)
• 密度：
  1.946±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335

反应信息

• 作为反应物：
  描述：

  3-溴-1H-吲唑-7-羧酸 在 氯甲酸乙酯 、 三乙胺 、 氨 作用下， 以 二氯甲烷 为溶剂， 反应 0.84h， 以95%的产率得到3-溴-1H-吲唑-7-甲酰胺
  参考文献：
  名称：

  Inhibitory effects of a series of 7-substituted-indazoles toward nitric oxide synthases: Particular potency of 1H-indazole-7-carbonitrile

  摘要：

  A series of new 7-monosubstituted and 3,7-disubstituted indazoles have been prepared and evaluated as inhibitors of nitric oxide synthases (NOS). 1H-Indazole-7-carbonitrile (6) was found equipotent to 7-nitro-1H-indazole (1) and demonstrated preference for constitutive NOS over inducible NOS. By contrast, 1H-indazole-7-carboxamide (8) was slightly less potent but demonstrated a surprising selectivity for the neuronal NOS. Further substitution of 6 by a Br-atom at carbon-3 of the heterocycle enhanced 10-fold the inhibitory effects. Inhibition of NO formation by 6 appeared to be competitive versus both substrate and the cofactor (6R)-5,6,7,8-tetrahydro-L-biopterin (H4B). In close analogies with 1, compound 6 strongly inhibited the NADPH oxidase activity of nNOS and induced a spin state transition of the heme-Fe-III. Our results are explained with the help of the X-ray structures that identified key-features for binding of 1 at the active site of NOS. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.04.056
• 作为产物：
  描述：

  7-氰基-3-溴-1H-吲唑 在 盐酸 作用下， 反应 48.0h， 以86%的产率得到3-溴-1H-吲唑-7-羧酸
  参考文献：
  名称：

  Inhibitory effects of a series of 7-substituted-indazoles toward nitric oxide synthases: Particular potency of 1H-indazole-7-carbonitrile

  摘要：

  A series of new 7-monosubstituted and 3,7-disubstituted indazoles have been prepared and evaluated as inhibitors of nitric oxide synthases (NOS). 1H-Indazole-7-carbonitrile (6) was found equipotent to 7-nitro-1H-indazole (1) and demonstrated preference for constitutive NOS over inducible NOS. By contrast, 1H-indazole-7-carboxamide (8) was slightly less potent but demonstrated a surprising selectivity for the neuronal NOS. Further substitution of 6 by a Br-atom at carbon-3 of the heterocycle enhanced 10-fold the inhibitory effects. Inhibition of NO formation by 6 appeared to be competitive versus both substrate and the cofactor (6R)-5,6,7,8-tetrahydro-L-biopterin (H4B). In close analogies with 1, compound 6 strongly inhibited the NADPH oxidase activity of nNOS and induced a spin state transition of the heme-Fe-III. Our results are explained with the help of the X-ray structures that identified key-features for binding of 1 at the active site of NOS. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.04.056

文献信息

• [EN] ROCK INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE ROCK ET LEURS UTILISATIONS
  申请人：DIZAL JIANGSU PHARMACEUTICAL CO LTD

  公开号：WO2023226965A1

  公开（公告）日：2023-11-30

  Disclosed herein are compounds of Formula (I), and pharmaceutically acceptable salts thereof, that are useful as ROCK inhibitors. Also disclosed are pharmaceutical compositions comprising a compound of Formula (I), and methods of using such compounds or compositions to treat ROCK-related disorder (e.g., glaucoma).

  本文公开了可用作 ROCK 抑制剂的式 (I) 化合物及其药学上可接受的盐。还公开了包含式（I）化合物的药物组合物，以及使用此类化合物或组合物治疗 ROCK 相关疾病（如青光眼）的方法。