1-Benzoyl-6-chloro-1H-pyrrolo<2,3-b>pyridine | 143468-11-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 1-Benzoyl-6-chloro-1H-pyrrolo<2,3-b>pyridine
• 英文别名: 1-benzoyl-6-chloro-7-azaindole；6-chloro-pyrrolo[2,3-b]pyridin-1-yl-phenyl-methanone；(6-Chloro-1H-pyrrolo[2,3-b]pyridin-1-yl)(phenyl)methanone；(6-chloropyrrolo[2,3-b]pyridin-1-yl)-phenylmethanone
• CAS: 143468-11-5
• 化学式: C₁₄H₉ClN₂O
• 分子量: 256.691
• InChiKey: UNOFAPHIMJQZQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1-Benzoyl-6-chloro-1H-pyrrolo<2,3-b>pyridine 在 aluminum (III) chloride 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.5h， 生成 1-(6-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)ethanone
  参考文献：
  名称：

  Synthesis of novel 7-azaindole derivatives containing pyridin-3-ylmethyl dithiocarbamate moiety as potent PKM2 activators and PKM2 nucleus translocation inhibitors

  摘要：

  Multiple lines of evidence have indicated that pyruvate kinase M2 (PKM2) is upregulated in most cancer cells and it is increasingly recognized as a potential therapeutic target in oncology. In a continuation of our discovery of lead compound 5 and SAR study, the 7-azaindole moiety in compound 5 was systematically optimized. The results showed that compound 6f, which has a difluoroethyl substitution on the 7-azaindole ring, exhibited high PKM2 activation potency and anti-proliferation activities on A375 cell lines. In a xenograft mouse model, oral administration of compound 6f led to significant tumor regression without obvious toxicity. Further mechanistic studies revealed that 6f could influence the translocation of PKM2 into nucleus, as well as induction of apoptosis and autophagy of A375 cells. More importantly, compound 6f significantly inhibited migration of A375 cells in a concentration-dependent manner. Collectively, 6f may serve as a lead compound in the development of potent PKM2 activators for cancer therapy. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.03.003
• 作为产物：
  描述：

  7-氮杂吲哚 在 间氯过氧苯甲酸 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 1-Benzoyl-6-chloro-1H-pyrrolo<2,3-b>pyridine
  参考文献：
  名称：

  一种取代氮杂吲唑甲醛的合成方法

  摘要：

  一种取代氮杂吲唑甲醛的合成方法，其利用专用过滤装置以进行，其特征在于，以7‑氮杂吲哚、3‑氯过氧基苯甲酸为基础原料，经7‑氧代‑7‑氮杂吲哚、1‑苯甲酰基‑6‑氯‑7‑氮杂吲哚、(6‑甲基‑1H‑吡咯并[2,3‑b]吡啶‑1‑基)(苯基)甲酮、6‑甲基‑7‑氮杂‑吲哚过渡，制得最终产物，6‑甲基‑7‑氮杂吲哚‑3‑甲醛。

  公开号：

  CN117820313A

文献信息

• Regioselective Functionalization of 1<i>H</i>-Pyrrolo[2,3-<i>b</i>]pyridine via Its<i>N</i>-Oxide
  作者：Satoshi Minakata、Mitsuo Komatsu、Yoshiki Ohshiro

  DOI：10.1055/s-1992-26193

  日期：——

  Selective functionalization of 1H-pyrrolo[2,3-b]pyridine (7-azaindole) at the 6-position was achieved by Reissert-Henze type reaction. Thus, halogeno (Cl, Br, I), cyano and thiocyanato groups were directly introduced to the pyridine ring of 7-azaindole.

  通过Reissert-Henze型反应，成功实现了在1H-吡咯并[2,3-b]吡啶（7-氮茚）的6-位进行选择性功能化。因此，氯、溴、碘、氰基和硫氰酸基团被直接引入到7-氮茚的吡啶环上。
• 4-(Heteroaryl-methyl and substituted heteroaryl-methyl)-imidazole-2-thiones acting as alpha2 adrenergic agonists
  申请人：Heidelbaugh M. Todd

  公开号：US20060069143A1

  公开（公告）日：2006-03-30

  Compounds of Formula 1 where the variables have the meaning defined in the specification are agonists of alpha 2 adrenergic receptors. Several compounds of the disclosure are specific or selective to alpha 2B and/or alpha 2C adrenergic receptors in preference over alpha 2A adrenergic receptors. Additionally some of the claimed compounds have no or only minimal cardivascular and/or sedatory activity. The compounds of Formula 1 are useful as medicaments in mammals, including humans, for treatment of diseases and or alleviations of conditions which are responsive to treatment by agonists of alpha 2 adrenergic receptors. Compounds of Formula 1 which have no significant cardiovascular and/or sedatory activity are useful for treating pain and other conditions with minimal side effects.

  式1的化合物，其中变量的含义在规范中定义，是α2肾上腺素受体的激动剂。本公开的几种化合物对α2B和/或alpha2C肾上腺素受体具有特异性或选择性，而不是alpha2A肾上腺素受体。此外，一些声明的化合物没有或仅有最小的心血管和/或镇静作用。式1的化合物可用作哺乳动物，包括人类，治疗对α2肾上腺素受体激动剂治疗有反应的疾病和/或缓解条件的药物。具有无显著心血管和/或镇静作用的式1的化合物可用于治疗疼痛和其他具有最小副作用的疾病。
• 4-(HETEROARYL-METHYL AND SUBSTITUTED HETEROARYL-METHYL)-IMIDAZOLE-2-THIONES ACTING AS ALPHA2 ADRENERGIC AGONISTS
  申请人：Heidelbaugh Todd M.

  公开号：US20080221152A1

  公开（公告）日：2008-09-11

  Compounds of Formula 1 where the variables have the meaning defined in the specification are agonists of alpha 2 adrenergic receptors. Several compounds of the disclosure are specific or selective to alpha 2B and/or alpha 2C adrenergic receptors in preference over alpha 2A adrenergic receptors. Additionally some of the claimed compounds have no or only minimal cardiovascular and/or sedatory activity. The compounds of Formula 1 are useful as medicaments in mammals, including humans, for treatment of diseases and or alleviations of conditions which are responsive to treatment by agonists of alpha 2 adrenergic receptors. Compounds of Formula 1 which have no significant cardiovascular and/or sedatory activity are useful for treating pain and other conditions with minimal side effects.

  公式1的化合物，其中变量的含义在说明书中定义，是α2肾上腺素受体的激动剂。本公开的几种化合物对α2B和/或α2C肾上腺素受体具有特异性或选择性，而不是α2A肾上腺素受体。此外，一些声明的化合物没有或只有最小的心血管和/或镇静活性。公式1的化合物在哺乳动物中，包括人类，用于治疗对α2肾上腺素受体激动剂有反应的疾病和/或缓解条件，是有用的药物。具有无显著心血管和/或镇静活性的公式1的化合物可用于治疗疼痛和其他具有最小副作用的病症。
• 一种取代氮杂吲唑甲醛的合成方法
  申请人：北京六合宁远医药科技股份有限公司

  公开号：CN117820313A

  公开（公告）日：2024-04-05

  一种取代氮杂吲唑甲醛的合成方法，其利用专用过滤装置以进行，其特征在于，以7‑氮杂吲哚、3‑氯过氧基苯甲酸为基础原料，经7‑氧代‑7‑氮杂吲哚、1‑苯甲酰基‑6‑氯‑7‑氮杂吲哚、(6‑甲基‑1H‑吡咯并[2,3‑b]吡啶‑1‑基)(苯基)甲酮、6‑甲基‑7‑氮杂‑吲哚过渡，制得最终产物，6‑甲基‑7‑氮杂吲哚‑3‑甲醛。
• US7399868B2
  申请人：——

  公开号：US7399868B2

  公开（公告）日：2008-07-15