1-(cyclopropylmethyl)-1H-indole-3-carboxylic acid | 128200-22-6

• 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: 1-(cyclopropylmethyl)-1H-indole-3-carboxylic acid
• 英文别名: 1-(cyclopropylmethyl)indole-3-carboxylic acid
• CAS: 128200-22-6
• 化学式: C₁₃H₁₃NO₂
• mdl: MFCD20085243
• 分子量: 215.252
• InChiKey: NQARVUKZERKXQQ-UHFFFAOYSA-N

物化性质

• 沸点：
  431.9±18.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(cyclopropylmethyl)-1H-indole-3-carboxylic acid 在 草酰氯 、 sodium hydride 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.0h， 生成 1-(cyclopropylmethyl)-N-(3-fluoropyridin-4-yl)-N-methyl-1H-indole-3-carboxamide
  参考文献：
  名称：

  [EN] ORAI CHANNEL INHIBITORS
  [FR] INHIBITEURS DE CANAL ORAI

  摘要：

  本申请提供了公式（I）或公式（II）的化合物，或其药学上可接受的盐。还提供了含有这些化合物的制药组合物，以及使用这些化合物治疗癌症、自身免疫性疾病和炎症性疾病的方法。

  公开号：

  WO2020180876A1
• 作为产物：
  描述：

  1-Cyclopropylmethyl-1H-indole-3-carboxylic acid methyl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 1-(cyclopropylmethyl)-1H-indole-3-carboxylic acid
  参考文献：
  名称：

  Design, synthesis, and biological activity of potent and selective inhibitors of mast cell tryptase

  摘要：

  A new series of novel mast cell tryptase inhibitors is reported, which features the use of an indole structure as the hydrophobic substituent on a m-benzylaminepiperidine template. The best members of this series display good in vitro activity and excellent selectivity against other serine proteases. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.002

文献信息

• Spirocyclic compounds incorporating five-membered rings with two
  申请人：Merck Sharp & Dohme Limited

  公开号：US04940703A1

  公开（公告）日：1990-07-10

  The present invention provides a compound of formula I or a salt or prodrug thereof: ##STR1## wherein the dotted line represents an optional chemical bond in one of the two possible positions; A represents a group of formula II: ##STR2## in which R.sup.1 represents hydrogen, hydroxy, C.sub.1-6 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.1-6 alkoxy, benzyloxy, hydroxy (C.sub.1-6)alkyl, halogen, amino, cyano, nitro, --CONR.sup.6 R.sup.7 or --SO.sub.2 NR.sup.6 R.sup.7, in which R.sup.6 and R.sup.7 independently represent hydrogen, halogen, C.sub.1-6 alkyl, C.sub.2-6 alkenyl or C.sub.2-6 alkynyl; R.sup.2 represents hydrogen, halogen, C.sub.1-6 alkyl, C.sub.1-6 alkoxy or C.sub.1-6 alkylcarbonyl; V represents nitrogen, --CH or --C--; and W represents oxygen, sulphur or --NR.sup.8, in which R.sup.8 represents hydrogen, C.sub.1-6 alkyl, C.sub.2-6 alkenyl or C.sub.2-6 alkynyl; two of X, Y and Z are the same or different and each represents oxygen, sulphur or nitrogen; and the remaining group X, Y or Z is carbon, or Y is carbonyl (C=O); and Q is the residue of an azacyclic or azabicyclic ring system; which compounds are useful in the treatment of psychotic disorders (e.g. schizophrenia and mania); anxiety; alcohol or drug withdrawal or dependence; pain; gastric stasis; gastric dysfunction (such as occurs with dyspepsia, peptic ulcer, reflux oesophagitis and flatulence); migraine, nausea and vomiting; movement disorders; and presenile and senile dementia.

  本发明提供了公式I的化合物或其盐或前药：其中虚线表示两种可能位置中的一个可选化学键；A代表公式II的一个基团：其中R.sup.1代表氢、羟基、C.sub.1-6烷基、C.sub.2-6烯基、C.sub.2-6炔基、C.sub.1-6烷氧基、苄氧基、羟基(C.sub.1-6)烷基、卤素、氨基、氰基、硝基、-CONR.sup.6 R.sup.7或-SO.sub.2 NR.sup.6 R.sup.7，其中R.sup.6和R.sup.7独立地代表氢、卤素、C.sub.1-6烷基、C.sub.2-6烯基或C.sub.2-6炔基；R.sup.2代表氢、卤素、C.sub.1-6烷基、C.sub.1-6烷氧基或C.sub.1-6烷基羰基；V代表氮、-CH或-C-；W代表氧、硫或-NR.sup.8，其中R.sup.8代表氢、C.sub.1-6烷基、C.sub.2-6烯基或C.sub.2-6炔基；X、Y和Z中的两个相同或不同，每个代表氧、硫或氮；剩余的X、Y或Z是碳，或Y是羰基(C=O)；Q是氮杂环或氮杂双环环系统的残基；这些化合物在治疗精神分裂症（如精神分裂症和狂躁症）；焦虑症；酒精或药物戒断或依赖；疼痛；胃排空延迟；胃功能障碍（如消化不良、消化性溃疡、反流性食道炎和胀气）；偏头痛、恶心和呕吐；运动障碍；以及老年性痴呆症和老年性痴呆症方面具有用处。
• Spirocyclic compounds incorporating five-membered rings with two heteroatoms
  申请人：MERCK SHARP & DOHME LTD.

  公开号：EP0337547A1

  公开（公告）日：1989-10-18

  The present invention provides a compound of formula I or a salt or prodrug thereof: wherein the dotted line represents an optional chemical bond in one of the two possible positions; A represents a group of formula II: in which R1 represents hydrogen, hydroxy, C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C1-6 alkoxy, benzyloxy, hydroxy(C1-6)alkyl, halogen, amino, cyano, nitro, -CONR6R7 or -S02NR6R7, in which R6 and R7 independently represent hydrogen, C1-6 alkyl, C2-6 alkenyl or C2-6 alkynyl; R2 represents hydrogen, halogen, C1 -6 alkyl, C1 -6 alkoxy or C1-6 alkylcarbonyl; V represents nitrogen, -CH or -C-; and W represents oxygen, sulphur or -NR8, in which R8 represents hydrogen, C, -6 alkyl, C2-6 alkenyl or C2-6 alkynyl; two of X, Y and Z are the same or different and each represents oxygen, sulphur or nitrogen; and the remaining group X, Y or Z is carbon, or Y is carbonyl (C = 0); and Q is the residue of an azacyclic or azabicyclic ring system; which compounds are useful in the treatment of psychotic disorders (e.g. schizophrenia and mania); anxiety; alcohol or drug withdrawal or,dependence; pain; gastric stasis; gastric dysfunction (such as occurs with dyspepsia, peptic ulcer, reflux oesophagitis and flatulence); migraine, nausea and vomiting; moyement disorders; and presenile and senile dementia,

  本发明提供一种式 I 的化合物或其盐或原药： 其中虚线代表两个可能位置之一的任选化学键；A 代表式 II 的基团： 其中 R1 代表氢、羟基、C1-6 烷基、C2-6 烯基、C2-6 烷炔基、C1-6 烷氧基、苄氧基、羟基（C1-6）烷基、卤素、氨基、氰基、硝基、-CONR6R7 或 -S02NR6R7，其中 R6 和 R7 独立地代表氢、C1-6 烷基、C2-6 烯基或 C2-6 烷炔基； R2 代表氢、卤素、C1-6 烷基、C1-6 烷氧基或 C1-6 烷基羰基； V 代表氮、-CH 或-C-；以及 W 代表氧、硫或-NR8，其中 R8 代表氢、C, -6 烷基、C2-6 烯基或 C2-6 烷炔基； X、Y 和 Z 中的两个相同或不同，各自代表氧、硫或氮；其余基团 X、Y 或 Z 为碳，或 Y 为羰基（C = 0）；以及 Q 是氮杂环或氮双环环系统的残基；这些化合物可用于治疗精神病（如精神分裂症和躁狂症）、焦虑症、酒精或药物戒断或依赖症、疼痛、胃淤血、胃功能障碍（如消化不良、消化性溃疡、反流性食管炎和胀气）、偏头痛、恶心和呕吐、精神错乱以及先天性和老年性痴呆症、
• Comprehensive Characterization of a Systematic Library of Alkyl and Alicyclic Synthetic Cannabinoids Related to CUMYL-PICA, CUMYL-BUTICA, CUMYL-CBMICA, and CUMYL-PINACA
  作者：Liesl K. Janssens、Adam Ametovski、Eric Sparkes、Rochelle Boyd、Felcia Lai、Callan J. Maloney、Dane Rhook、Roy R. Gerona、Matthew Connolly、Huiling Liu、David E. Hibbs、Elizabeth A. Cairns、Samuel D. Banister、Christophe P. Stove

  DOI：10.1021/acschemneuro.2c00408

  日期：2023.1.4
• Orai Channel Inhibitors
  申请人：Beth Israel Deaconess Medical Center, Inc.

  公开号：US20220153735A1

  公开（公告）日：2022-05-19

  The present application provides a compound of Formula (I) or Formula (II), or a pharmaceutically acceptable salt thereof. Pharmaceutical compositions containing these compounds, and methods of using these compounds for treating cancer, autoimmune diseases, and inflammatory diseases are also provided.
• US4940703A
  申请人：——

  公开号：US4940703A

  公开（公告）日：1990-07-10