2-[1-(2-chlorobenzyl)-1H-indol-3-yl]-2-oxo-N-(pyridin-4-yl)acetamide

• 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: 2-[1-(2-chlorobenzyl)-1H-indol-3-yl]-2-oxo-N-(pyridin-4-yl)acetamide
• 英文别名: N-(Pyridin-4-yl)-[1-(2-chlorobenzyl)indol-3-yl]glyoxylamide；2-[1-[(2-chlorophenyl)methyl]indol-3-yl]-2-oxo-N-pyridin-4-ylacetamide
• 化学式: C₂₂H₁₆ClN₃O₂
• 分子量: 389.841
• InChiKey: BMVCJHZEGJYLHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  64
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(1H-indol-3-yl)-2-oxo-N-(pyridin-4-yl)acetamide 、 邻氯氯苄 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 2.25h， 以45%的产率得到2-[1-(2-chlorobenzyl)-1H-indol-3-yl]-2-oxo-N-(pyridin-4-yl)acetamide
  参考文献：
  名称：

  Synthesis and structure–activity relationships of N-aryl(indol-3-yl)glyoxamides as antitumor agents

  摘要：

  The synthesis and study of the structure-activity relationships of cytotoxic compounds based on N-pyridinyl or N-aryl-2-(1-benzylindol-3-yl)glyoxamide skeleton, represented by the lead structures D-24241 and D-24851, are described. The presence of N-(pyridin-4-yl) moiety was crucial for activity and 2-[1(4-chloro-3-nitrobenzyl)-1H-indol-3-yl]-2-oxo-N-(pyridin-4-yl) acetamide (55), the most potent derivative, showed IC(50) = 39 nM, 51 nM and 11 nM against HeLa/KB (human cervix carcinoma), L1210 (murine leukemia) and SKOV3 (human ovarian carcinoma) cell lines proliferation assay, respectively, as active as the lead compounds. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.07.048

文献信息

• N-substituted indole-3-glyoxylamides having anti-asthmatic, antiallergic and immunosuppressant/immuno-modulating action
  申请人：ASTA Medica AG

  公开号：US06344467B1

  公开（公告）日：2002-02-05

  The invention relates to novel N-substituted indole-3-glyoxylamides, to processes for their preparation and to their pharmaceutical use. The compounds have antiasthmatic, antiallergic and immunosuppressant/immunomodulating actions.

  这项发明涉及新型N-取代吲哚-3-甘氨酰胺，以及它们的制备过程和药用。这些化合物具有抗哮喘、抗过敏和免疫抑制/免疫调节作用。
• United states patent office
  申请人：ASTA Medica Aktiengesellschaft

  公开号：US20030023093A1

  公开（公告）日：2003-01-30

  The invention relates to the use of N-substituted indole-3-glyoxylamides of the general formula I as antitumor agents 1 and to a pharmaceutical composition having antitumor action, characterized in that it contains at least one of the compounds of the general formula 1, if appropriate also in the form of the physiologically tolerable acid addition salts or N-oxides. Furthermore, the invention also includes antitumor agents comprising as active compound one or more N-substituted indole-3-glyoxylamides according to the general formula 1 and, if appropriate, their physiologically tolerable acid addition salts and, if possible, N-oxides and a pharmaceutically utilizable carrier and/or diluent or auxiliary substance in the form of tablets, coated tablets, capsules, solutions for infusion or ampoules, suppositories, patches, powder preparations which can be employed by inhalation, suspensions, creams and ointments.

  本发明涉及使用一般式I的N-取代吲哚-3-甘氧酰胺作为抗肿瘤剂，以及具有抗肿瘤作用的药物组合物，其特征在于至少含有一种一般式1的化合物，必要时也可以是生理耐受的酸加盐或N-氧化物的形式。此外，本发明还包括作为活性化合物的一种或多种N-取代吲哚-3-甘氧酰胺抗肿瘤剂，以及必要时它们的生理耐受的酸加盐和可能的N-氧化物，以及可用于制药的载体和/或稀释剂或辅助物质的药物组合物，包括片剂、包衣片剂、胶囊、输注溶液或安瓿、栓剂、贴片、可通过吸入使用的粉剂制剂、悬浮液、乳霜和软膏。
• N-substituted indole-3glyoxylamides having anti-asthmatic, antiallergic and immunosuppressant/immuno-modulating action
  申请人：——

  公开号：US20020161025A1

  公开（公告）日：2002-10-31

  The invention relates to novel N-substituted indole-3-glyoxylamides, to processes for their preparation and to their pharmaceutical use. The compounds have antiasthmatic, antiallergic and immunosuppressant/immunomodulating actions.

  本发明涉及新型N-取代的吲哚-3-甘氧酰胺，其制备方法以及它们的药用。该化合物具有抗哮喘、抗过敏和免疫抑制/免疫调节作用。
• Indolyl-3-glyoxylic acid derivatives having antitumor action
  申请人：Nickel Bernd

  公开号：US20080027110A1

  公开（公告）日：2008-01-31

  The invention relates to the use of N-substituted indole-3-glyoxylamides of the general formula I as antitumor agents and to a pharmaceutical composition having antitumor action, characterized in that it contains at least one of the compounds of the general formula 1, if appropriate also in the form of the physiologically tolerable acid addition salts or N-oxides. Furthermore, the invention also includes antitumor agents comprising as active compound one or more N-substituted indole-3-glyoxylamides according to the general formula 1 and, if appropriate, their physiologically tolerable acid addition salts and, if possible, N-oxides and a pharmaceutically utilizable carrier and/or diluent or auxiliary substance in the form of tablets, coated tablets, capsules, solutions for infusion or ampoules, suppositories, patches, powder preparations which can be employed by inhalation, suspensions, creams and ointments.

  本发明涉及使用一般式I的N-取代吲哚-3-甘氧酰胺作为抗肿瘤剂，以及具有抗肿瘤作用的药物组合物，其特征在于至少含有一种一般式1的化合物，如适当，还可以是生理耐受的酸加成盐或N-氧化物的形式。此外，本发明还包括作为活性化合物的一种或多种N-取代吲哚-3-甘氧酰胺的抗肿瘤剂，以及它们的生理耐受的酸加成盐和可能的N-氧化物，以及在片剂、包衣片剂、胶囊、输注溶液或安瓿、栓剂、贴片、可通过吸入使用的粉剂制剂、悬浮液、乳霜和软膏等药物可利用载体和/或稀释剂或辅助物质的形式。
• N-SUBSTITUIERTE INDOL-3-GLYOXYLAMIDE MIT ANTIASTHMATISCHER, ANTIALLERGISCHER UND IMMUNSUPPRESSIVER/IMMUNMODULIERENDER WIRKUNG
  申请人：Baxter Healthcare SA

  公开号：EP0931063B1

  公开（公告）日：2006-10-18