5-氯-3-甲基-1H-吲哚-2-羧酸乙酯 | 16382-20-0

• 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
• 中文名称: 5-氯-3-甲基-1H-吲哚-2-羧酸乙酯
• 英文名称: ethyl 5-chloro-3-methyl-1H-indole-2-carboxylate
• 英文别名: 5-chloro-3-methyl-1H-indole-2-carboxylic acid ethyl ester
• CAS: 16382-20-0
• 化学式: C₁₂H₁₂ClNO₂
• mdl: MFCD00458319
• 分子量: 237.686
• InChiKey: KERASJPARWIHBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P280
• 危险性描述：
  H302,H317

反应信息

• 作为反应物：
  描述：

  5-氯-3-甲基-1H-吲哚-2-羧酸乙酯 在 一水合肼 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 6.0h， 生成 5-chloro-3-methyl-N-(8-phenyl-3-oxo-1-thia-4-azaspiro-[4.5]decan-4-yl)-1H-indole-2-carboxamide
  参考文献：
  名称：

  Superior inhibition of influenza virus hemagglutinin-mediated fusion by indole-substituted spirothiazolidinones

  摘要：

  The influenza virus hemagglutinin (HA) mediates membrane fusion after viral entry by endocytosis. The fusion process requires drastic low pH-induced HA refolding and is prevented by arbidol and tert-butylhydroquinone (TBHQ). We here report a class of superior inhibitors with indole-substituted spirothiazolidinone structure. The most active analogue 5f has an EC50 value against influenza A/H3N2 virus of 1 nM and selectivity index of almost 2000. Resistance data and in silico modeling indicate that 5f combines optimized fitting in the TBHQ/arbidol HA binding pocket with a capability for endosomal accumulation. Both criteria appear relevant to achieve superior inhibitors of HA-mediated fusion.

  DOI：

  10.1016/j.bmc.2019.115130
• 作为产物：
  描述：

  2-乙基乙酰乙酸乙酯 在 盐酸 作用下， 以 乙醇 为溶剂， 生成 5-氯-3-甲基-1H-吲哚-2-羧酸乙酯
  参考文献：
  名称：

  Hiremath, Shivayogi P.; Thakar, Shreeram B.; Purohit, Muralidhar G., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 9, p. 770 - 774

  摘要：

  DOI：

文献信息

• Phenylaminopropanol derivatives and methods of their use
  申请人：Kim Younghee Callain

  公开号：US20050222148A1

  公开（公告）日：2005-10-06

  The present invention is directed to phenylaminopropanol derivatives of formula I: or a pharmaceutically acceptable salt thereof, compositions containing these derivatives, and methods of their use for the prevention and treatment of conditions ameliorated by monoamine reuptake including, inter alia, vasomotor symptoms (VMS), sexual dysfunction, gastrointestinal and genitourinary disorders, chronic fatigue syndrome, fibromylagia syndrome, nervous system disorders, and combinations thereof, particularly those conditions selected from the group consisting of major depressive disorder, vasomotor symptoms, stress and urge urinary incontinence, fibromyalgia, pain, diabetic neuropathy, and combinations thereof.

  本发明涉及式I的苯胺丙醇衍生物： 或其药学上可接受的盐，含有这些衍生物的组合物，以及它们用于通过单胺再摄取改善的症状的预防和治疗方法，包括但不限于血管运动症状（VMS）、性功能障碍、胃肠道和泌尿系统疾病、慢性疲劳综合征、纤维肌痛综合征、神经系统疾病，以及其中的组合，特别是从包括重性抑郁障碍、血管运动症状、压力性和切勿性尿失禁、纤维肌痛、疼痛、糖尿病性神经病变以及其中的组合的一组中选择的那些症状。
• Substituted n-(indole-2-carbonyl-) amides and derivatives as glycogen phosphorylase inhibitors
  申请人：Pfizer Inc.

  公开号：US06297269B1

  公开（公告）日：2001-10-02

  Compounds of the formula I: and their compositions are useful as glycogen phosphorylase inhibitors.

  公式I的化合物及其组合物可用作糖原磷酸化酶抑制剂。
• [EN] PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR MODULATORS<br/>[FR] MODULATEURS DES RECEPTEURS ACTIVES PAR LES PROLIFERATEURS DE PEROXYSOMES
  申请人：LILLY CO ELI

  公开号：WO2005054176A1

  公开（公告）日：2005-06-16

  The present invention is directed to a compound of formula (I), or a pharmaceutically acceptable salt, solvate hydrate or stereoisomer thereof, which is useful in treating or preventing disorders mediated by a peroxisome proliferator activated receptor (PPAR) such as syndrome X, type II diabetes, hyperglycemia, hyperlipidemia, obesity, coagaulopathy, hypertension, arteriosclerosis, and other disorders related to syndrome X and cardiovascular diseases.

  本发明涉及一种式（I）的化合物，或其药学上可接受的盐、溶剂合物、水合物或立体异构体，可用于治疗或预防由过氧化物酶体增殖物激活受体（PPAR）介导的疾病，如X综合征、2型糖尿病、高血糖、高脂血症、肥胖、凝血障碍、高血压、动脉粥样硬化以及其他与X综合征和心血管疾病相关的疾病。
• Indole-2-carboxamides as Allosteric Modulators of the Cannabinoid CB₁ Receptor
  作者：Francesco Piscitelli、Alessia Ligresti、Giuseppe La Regina、Antonio Coluccia、Ludovica Morera、Marco Allarà、Ettore Novellino、Vincenzo Di Marzo、Romano Silvestri

  DOI：10.1021/jm201485c

  日期：2012.6.14

  We synthesized new N-phenylethyl-1H-indole-2-carboxamides as the first SAR study of allosteric modulators of the CB1 receptor. The presence of the carboxamide functionality was required in order to obtain a stimulatory effect. The maximum stimulatory activity on CB1 was exerted by carboxamides 13 (EC50 = 50 nM) and 21 (EC50 = 90 nM) bearing a dimethylamino or piperidinyl group, respectively, at position

  我们合成了新的N-苯乙基-1 H-吲哚-2-羧酰胺作为CB 1受体的变构调节剂的第一个SAR研究。为了获得刺激作用，需要羧酰胺官能团的存在。CB 1的最大刺激活性是由分别在苯乙部分的4位带有二甲氨基或哌啶基的羧酰胺13（EC 50 = 50 nM）和21（EC 50 = 90 nM）发挥的。吲哚的5。
• [EN] INDOLE DERIVATIVES AND USES THEREOF FOR TREATING A CANCER<br/>[FR] DÉRIVÉS D'INDOLE ET LEURS UTILISATIONS POUR LE TRAITEMENT D'UN CANCER
  申请人：UNIV CLAUDE BERNARD LYON

  公开号：WO2022008475A1

  公开（公告）日：2022-01-13

  The present invention relates to indole derivatives of formula (I') as CK2 inhibitor and pharmaceutical compositions comprising the same. The present invention further relates to the use of such compounds of formula (I) for use for preventing and/or treating a cancer.

  本发明涉及一种具有如下式（I'）的吲哚衍生物作为CK2抑制剂，以及包含该衍生物的药物组合物。本发明还涉及利用该式（I）化合物用于预防和/或治疗癌症的用途。