1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid ethyl ester

• 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: 1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid ethyl ester
• 英文别名: 1H-Pyrrolo[2,3-b]pyridin-3-carbonsaeure-aethylester；ethyl 1H-pyrrolo[2,3-b]pyridine-3-carboxylate
• 化学式: C₁₀H₁₀N₂O₂
• 分子量: 190.202
• InChiKey: OYJHFKWECVZRSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid ethyl ester 、 2,4-二氯苯甲酰氯 在 sodium hydride 作用下， 以85.8%的产率得到Ethyl 1-(2,4-dichlorobenzoyl)pyrrolo[2,3-b]pyridine-3-carboxylate
  参考文献：
  名称：

  Acrosin structure-based design, synthesis and biological activities of 7-azaindol derivatives as new acrosin inhibitors

  摘要：

  A series of 7-azaindol derivatives were designed based on the homologous 3D model of human acrosin. These compounds were synthesized and evaluated for their human acrosin inhibitory activities in vitro. Compounds 7a, 7i, 7j, 7k and 7n showed highly inhibitory activity against human acrosin. The three-dimensional structure activity relationship was investigated through a CoMFA model, which provided valuable information to further study of potential human acrosin inhibitors. (C) 2010 Published by Elsevier B.V. on behalf of Chinese Chemical Society.

  DOI：

  10.1016/j.cclet.2010.09.033
• 作为产物：
  描述：

  3-氰基-7-氮杂吲哚 在 盐酸 作用下， 生成 1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Acrosin structure-based design, synthesis and biological activities of 7-azaindol derivatives as new acrosin inhibitors

  摘要：

  A series of 7-azaindol derivatives were designed based on the homologous 3D model of human acrosin. These compounds were synthesized and evaluated for their human acrosin inhibitory activities in vitro. Compounds 7a, 7i, 7j, 7k and 7n showed highly inhibitory activity against human acrosin. The three-dimensional structure activity relationship was investigated through a CoMFA model, which provided valuable information to further study of potential human acrosin inhibitors. (C) 2010 Published by Elsevier B.V. on behalf of Chinese Chemical Society.

  DOI：

  10.1016/j.cclet.2010.09.033

文献信息

• 7-AZAINDOLE DERIVATIVES
  申请人：Klein Markus

  公开号：US20110166175A1

  公开（公告）日：2011-07-07

  Novel 7-azaindole derivatives of the formula (I), in which U, L, R, Y, X 1 , X 2 and X 3 have the meanings indicated in Claim 1 ), are kinase inhibitors and can be used for the treatment of diseases and conditions such as diabetes, obesity, metabolic syndrome (dyslipidaemia), systemic and pulmonary hypertonia, cardiovascular diseases and kidney diseases, generally in any type of fibroses, inflammatory processes, tumours and tumour diseases.

  小说7-氮杂吲哚衍生物的化学式（I），其中U、L、R、Y、X1、X2和X3具有声明中指示的含义，是激酶抑制剂，可用于治疗疾病和病况，如糖尿病、肥胖症、代谢综合征（血脂异常）、系统性和肺动脉高压、心血管疾病和肾脏疾病，通常在任何类型的纤维化、炎症过程、肿瘤和肿瘤疾病中。
• 1H-pyrrolo[2,3-b]pyridine: A new scaffold for human neutrophil elastase (HNE) inhibitors
  作者：Letizia Crocetti、Maria Paola Giovannoni、Igor A. Schepetkin、Mark T. Quinn、Andrei I. Khlebnikov、Niccolò Cantini、Gabriella Guerrini、Antonella Iacovone、Elisabetta Teodori、Claudia Vergelli

  DOI：10.1016/j.bmc.2018.09.034

  日期：2018.11

  belonging to the chymotrypsin family. It is an important target for the development of novel and selective inhibitors for the treatment of inflammatory diseases, especially pulmonary pathologies. Here, we report the synthesis and biological evaluation of a new series of HNE inhibitors with a pyrrolo[2,3-b]pyridine scaffold, which is an isomer of our previously reported indazoles, in order to assess how a

  人嗜中性粒细胞弹性蛋白酶（HNE）是一种有效的丝氨酸蛋白酶，属于胰凝乳蛋白酶家族。它是开发用于治疗炎性疾病，尤其是肺部疾病的新型和选择性抑制剂的重要目标。在这里，我们报道了带有吡咯并[2,3- b ]吡啶骨架的一系列新的HNE抑制剂的合成和生物学评估，吡咯并[2,3- b ]吡啶骨架是我们先前报道的吲唑的异构体，目的是评估氮如何从氮转移。从位置2到位置7影响活动。大多数新化合物是有效的HNE抑制剂，IC 50值在微摩尔/亚微摩尔范围内，有些化合物在低纳摩尔水平下具有活性。例如2a和2b抑制HNE的IC 50值分别为15和14 nM。在双环部分和恶二唑环中，杂原子位置不同的化合物的分子模型表明，酶抑制剂复合物的几何结构与观察到的生物活性相符。对接实验表明，HNE催化三联体Ser195-His57-Asp102中活性吡咯并[2,3- b ]吡啶的取向与抑制剂与酶的相互作用有关。因此，吡咯并[2，3-
• 7-Azaindole. III. Syntheses of 7-Aza Analogs of Some Biologically Significant Indole Derivatives¹
  作者：Michael M. Robison、Bonnie L. Robison

  DOI：10.1021/ja01587a046

  日期：1956.3
• US8466170B2
  申请人：——

  公开号：US8466170B2

  公开（公告）日：2013-06-18
• [DE] 7-AZAINDOLDERIVATE<br/>[EN] 7-AZAINDOLE DERIVATIVES<br/>[FR] DÉRIVÉS DE 7-AZAINDOLE
  申请人：MERCK PATENT GMBH

  公开号：WO2010020308A1

  公开（公告）日：2010-02-25

  Neue 7-Azaindolderivate der Formel (I) worin U, L. R, Y, X1,X2 und X3 die in Anspruch (1) angegebenen Bedeutungen haben, sind Kinase-Inhibitoren und können zur Behandlung von Krankheiten und Leiden wie Diabetes, Fettsucht, metabolisches Syndrom (Dyslipidämie), systemische und pulmonale Hypertonie, Herzkreislauferkrankungen und Nierenerkrankungen, allgemein bei jeglicher Art von Fibrosen, entzündlichen Prozessen, Tumoren und Tumorerkrankungen verwendet werden.