ethyl 5-cyano-1-ethyl-1H-indole-2-carboxylate | 200185-54-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: ethyl 5-cyano-1-ethyl-1H-indole-2-carboxylate
• 英文别名: ethyl 5-cyano-1-ethylindole-2-carboxylate
• CAS: 200185-54-2
• 化学式: C₁₄H₁₄N₂O₂
• 分子量: 242.277
• InChiKey: MEPNWTVMVBHMEK-UHFFFAOYSA-N

物化性质

• 沸点：
  414.2±25.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 5-cyano-1-ethyl-1H-indole-2-carboxylate 在 盐酸 作用下， 以 水 为溶剂， 以65.6%的产率得到5-cyano-1-ethyl-1H-indole-2-carboxylic acid
  参考文献：
  名称：

  [EN] BENZOIMIDAZOLE DERIVATIVES AS PAD4 INHIBITORS
  [FR] DÉRIVÉS DE BENZOIMIDAZOLE EN TANT QU'INHIBITEURS DE PAD4

  摘要：

  式(I)的化合物：其中X、Y、R1和R3-R11如本文所定义，并其盐为PAD4抑制剂，可能在治疗各种疾病中有用，例如类风湿关节炎、血管炎、系统性红斑狼疮、溃疡性结肠炎、癌症、囊性纤维化、哮喘、皮肤红斑狼疮和牛皮癣。

  公开号：

  WO2016185279A1
• 作为产物：
  描述：

  溴乙烷 、 5-氰基-1H-吲哚-2-羧酸乙酯 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 3.5h， 以59.8%的产率得到ethyl 5-cyano-1-ethyl-1H-indole-2-carboxylate
  参考文献：
  名称：

  [EN] BENZOIMIDAZOLE DERIVATIVES AS PAD4 INHIBITORS
  [FR] DÉRIVÉS DE BENZOIMIDAZOLE EN TANT QU'INHIBITEURS DE PAD4

  摘要：

  式(I)的化合物：其中X、Y、R1和R3-R11如本文所定义，并其盐为PAD4抑制剂，可能在治疗各种疾病中有用，例如类风湿关节炎、血管炎、系统性红斑狼疮、溃疡性结肠炎、癌症、囊性纤维化、哮喘、皮肤红斑狼疮和牛皮癣。

  公开号：

  WO2016185279A1

文献信息

• Compounds as delta opioid agonists
  申请人：Pfizer Inc.

  公开号：US06200978B1

  公开（公告）日：2001-03-13

  Compounds of the formula (I)—shown below—are described. The compounds are useful in the manufacture of a pharmaceutical composition for preventing or treating inflammatory diseases such as arthritis, psoriasis, asthma, or inflammatory bowel disease, disorders of respiratory function, gastrointestinal disorders such as functional bowel disease, functional GI disorders such as irritable bowel syndrome, functional diarrhoea, functional distension, functional pain, non-ulcerogenic dyspepsia or others associated with disorders of motility or secretion, urogenital tract disorders such as incontinence, as analgesics for treating pain including non-somatic pain, or as immunosuppressants to prevent rejection in organ transplant and skin graft.

  化合物的公式（I）如下所示。这些化合物在制造用于预防或治疗炎症性疾病，如关节炎、牛皮癣、哮喘、炎症性肠病、呼吸功能障碍、胃肠功能紊乱、功能性肠道疾病、功能性胃肠障碍（如肠易激综合征）、功能性腹泻、功能性胀气、功能性疼痛、非溃疡性消化不良或与运动或分泌紊乱相关的其他疾病方面非常有用，还可用作镇痛药物，用于治疗包括非体感疼痛在内的疼痛，或作为免疫抑制剂，以预防器官移植和皮肤移植中的排斥反应。
• Benzoimidazole derivatives as PAD4 inhibitors
  申请人：GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED

  公开号：US10407407B2

  公开（公告）日：2019-09-10

  Compounds of formula (I): wherein X, Y, R1 and R3-R11 are as herein defined, and salts thereof are PAD4 inhibitors and may be useful in the treatment of various disorders, for example rheumatoid arthritis, vasculitis, systemic lupus erythematosus, ulcerative colitis, cancer, cystic fibrosis, asthma, cutaneous lupus erythematosis, and psoriasis.

  式（I）：其中 X、Y、R1 和 R3-R11 如本文所定义的化合物及其盐类是 PAD4 抑制剂，可用于治疗各种疾病，例如类风湿性关节炎、血管炎、系统性红斑狼疮、溃疡性结肠炎、癌症、囊性纤维化、哮喘、皮肤红斑狼疮和银屑病。
• Design, synthesis and biological activity of amidinobicyclic compounds (derivatives of DX-9065a) as factor Xa inhibitors: SAR study of S1 and aryl binding sites
  作者：Satoshi Komoriya、Naoaki Kanaya、Takayasu Nagahara、Asako Yokoyama、Kazue Inamura、Yukio Yokoyama、Shin-ichi Katakura、Tsuyoshi Hara

  DOI：10.1016/j.bmc.2004.02.032

  日期：2004.5

  Since factor Xa (fXa) plays a pivotal role in the blood coagulation cascade, inhibition of fXa is thought to be an effective treatment for a variety of thrombotic events. (2,)-2-[4-[[(3S)-l-Acetimidoyl-3-pyrrolidinyl]oxy]phenyl]-3-(7-amidino-2-naphthyl)propanoic acid hydrochloride pentahydrate (DX-9065a) was previously found in our laboratory as a novel orally active factor Xa inhibitor. DX-9065a exhibits a strong inhibitory activity toward fXa by occupying the substrate recognition (called SI) sites and aryl binding sites of fXa. Herein we describe conversions of the amidinonaphthalene and the acetimidoylpyrrolidine moieties of DX-9065a. Some compounds showed remarkably increased in vitro anti-factor Xa and PRCT activities compared with those of DX9065a. The most promising compound 38 showed four times the prolongation of APTT against DX-9065a after oral administration to rats. (C) 2004 Elsevier Ltd. All rights reserved.
• AROMATIC AMIDINE DERIVATIVES USEFUL AS SELECTIVE THROMBIN INHIBITORS
  申请人：C & C Research Laboratories

  公开号：EP0918768B1

  公开（公告）日：2002-01-09
• BENZOIMIDAZOLE DERIVATIVES AS PAD4 INHIBITORS
  申请人：GlaxoSmithKline Intellectual Property Development Limited

  公开号：EP3298003A1

  公开（公告）日：2018-03-28