methyl 3-(2-chloro-2-oxoacetyl)-1H-indole-7-carboxylate | 313337-48-3

• 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: methyl 3-(2-chloro-2-oxoacetyl)-1H-indole-7-carboxylate
• 英文别名: (7-methoxycarbonyl-indol-3-yl)-oxoacetyl chloride
• CAS: 313337-48-3
• 化学式: C₁₂H₈ClNO₄
• 分子量: 265.653
• InChiKey: LLEKXQUBWGPIRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  76.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-(2-chloro-2-oxoacetyl)-1H-indole-7-carboxylate 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 生成 N¹,N⁴-bis(3-(2-(7-(methoxycarbonyl)-1H-indol-3-yl)-2-oxoacetamido)propyl)butane-1,4-diaminium 2,2,2-trifluoroacetate
  参考文献：
  名称：

  Exploration of the antibiotic potentiating activity of indolglyoxylpolyamines

  摘要：

  A series of substituted di-indolglyoxylamido-spermine analogues were prepared and evaluated for intrinsic antimicrobial properties and the ability to enhance antibiotic action. As a compound class, intrinsic activity was typically observed towards Gram-positive bacteria and the fungus Cryptococcus neoformans, with notable exceptions being the 5-bromo- and 6-chloro-indole analogues which also exhibited modest activity (MIC 34-50 mu M) towards the Gram-negative bacteria Escherichia coli and Klebsiella pneumoniae. Several analogues enhanced the activity of doxycycline towards the Gram-negative bacteria Pseudomonas aeruginosa, E. coli, K. pneumoniae and Acinetobacter baumannii. Of particular note was the identification of five antibiotic enhancing analogues (5-Br, 7-F, 5-Me, 7-Me, 7-Me) which also exhibited low to no cytotoxicity and red blood cell haemolytic properties. The mechanisms of action of the 5-Br and 7-F analogues were attributed to the ability to disrupt the integrity of, and depolarize, bacterial membranes. (C) 2019 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2019.111708
• 作为产物：
  描述：

  7-吲哚甲酸 在 硫酸 作用下， 以 乙醚 为溶剂， 反应 20.0h， 生成 methyl 3-(2-chloro-2-oxoacetyl)-1H-indole-7-carboxylate
  参考文献：
  名称：

  [EN] INDOLYLMALEIMIDES AS SOFT PAN-PKC INHIBITORS
  [FR] INDOLYLMALÉIMIDES SERVANT D'INHIBITEURS DOUX DE PAN-PKC

  摘要：

  本发明涉及新的激酶抑制剂，更具体地是软性PKC抑制剂，包括这些抑制剂的组合物，特别是制药品，以及这些抑制剂在疾病治疗和预防中的用途。具体来说，本发明涉及新的软性PKC抑制剂组合物，特别是制药品，包括这些抑制剂，以及这些抑制剂在疾病治疗和预防中的用途。此外，本发明涉及治疗方法和使用所述化合物制造药物的方法，适用于多种治疗适应症，包括自身免疫和炎症性疾病。

  公开号：

  WO2013004709A1

文献信息

• Antiviral indoleoxoacetyl piperazine derivatives
  申请人：Bristol-Myers Squibb Company

  公开号：US06469006B1

  公开（公告）日：2002-10-22

  This invention provides compounds having drug and bio-affecting properties, their pharmaceutical compositions and method of use. In particular, the invention is concerned with indoleoxoacetyl piperazine derivatives. These compounds possess unique antiviral activity, whether used alone or in combination with other antivirals, antiinfectives, immunomodulators or HIV entry inhibitors. More particularly, the present invention relates to the treatment of HIV and AIDS.

  本发明提供了具有药物和生物影响性质的化合物，其制药组合物和使用方法。特别地，本发明涉及到吲哚氧乙酰哌嗪衍生物。这些化合物具有独特的抗病毒活性，无论是单独使用还是与其他抗病毒药物、抗感染药物、免疫调节剂或HIV进入抑制剂联合使用。更具体地，本发明涉及治疗HIV和艾滋病。
• EP1105135A4
  申请人：——

  公开号：EP1105135A4

  公开（公告）日：2001-12-12
• ANTIVIRAL INDOLEOXOACETYL PIPERAZINE DERIVATIVES
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：EP1105135A1

  公开（公告）日：2001-06-13
• US6469006B1
  申请人：——

  公开号：US6469006B1

  公开（公告）日：2002-10-22
• [EN] ANTIVIRAL INDOLEOXOACETYL PIPERAZINE DERIVATIVES<br/>[FR] DERIVES D'INDOLEOXOACETYLPIPERAZINE, A PROPRIETES ANTIVIRALES
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2000076521A1

  公开（公告）日：2000-12-21

  This invention provides compounds having drug and bio-affecting properties, their pharmaceutical compositions and method of use. In particular, the invention is concerned with indoleoxoacetyl piperazine derivatives. These compounds possess unique antiviral activity, whether used alone or in combination with other antivirals, antiinfectives, immunomodulators or HIV entry inhibitors. More particularly, the present invention relates to the treatment of HIV and AIDS.