1-methyl-3-(α-bromoacrylamido)pyrazole-5-carboxylic acid | 177409-52-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-methyl-3-(α-bromoacrylamido)pyrazole-5-carboxylic acid
• 英文别名: 5-(2-Bromoprop-2-enoylamino)-2-methylpyrazole-3-carboxylic acid
• CAS: 177409-52-8
• 化学式: C₈H₈BrN₃O₃
• 分子量: 274.074
• InChiKey: MYYIOBDMJZJJBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  84.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-methyl-3-(α-bromoacrylamido)pyrazole-5-carboxylic acid 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 1-methyl-3-(α-bromoacrylamido)pyrazole 5-carboxyl chlodride
  参考文献：
  名称：

  Acryloyl derivatives analogous to distamycin, process for preparing them, and their use as antitumor agents

  摘要：

  化合物是acryloyl取代的formula（I）的distamycin衍生物，其中：n为2、3或4；m为1或2；X和Y相同或不同，分别选自N和CH，为聚醚杂环链的每个杂环环；R1和R2相同或不同，选自氢、卤素和C1-C4烷基；R3为氢或卤素；B选自（a）、（b）、（c）、（d）、（e）、（f）、（g）和—C≡N；其中R4、R5、R6、R7、R8、R10、R11和R12独立地选自氢或C1-C4烷基；R9为氢或羟基，或其药用可接受的盐；条件是a）R4、R5和R6中至少有一个是烷基；b）聚杂环链内至少有一个杂环环不是吡咯；和c）X和Y对于相同的杂环环不同时为N；这些化合物可用作抗肿瘤剂。

  公开号：

  US06753316B1
• 作为产物：
  描述：

  1-甲基-3-苄氧基-羰基氨基-吡唑-5-羧酸 在 palladium on activated charcoal 苄基三乙基氯化铵 、 氢气 、 potassium carbonate 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-methyl-3-(α-bromoacrylamido)pyrazole-5-carboxylic acid
  参考文献：
  名称：

  Synthesis and antitumor activity of novel distamycin derivatives

  摘要：

  Several distamycin derivatives were synthesized from deformyl distamycin by coupling with different azole carboxylic acids bearing an alkylating moiety. Some of them showed good activities in vitro and in vivo against L 1210 murine leukemia. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00204-1

文献信息

• Synthesis and growth inhibition activity of α-Bromoacrylic heterocyclic and benzoheterocyclic derivatives of distamycin A modified on the amidino moiety
  作者：Pier Giovanni Baraldi、Italo Beria、Paolo Cozzi、Nicoletta Bianchi、Roberto Gambari、Romeo Romagnoli

  DOI：10.1016/s0968-0896(02)00533-3

  日期：2003.3

  The design, synthesis and in vitro activities of novel alpha-bromoacryloyl pyrazole, imidazole and benzoheterocyclic derivatives of distamycin A, in which the amidino moiety has been replaced by moieties of different physico-chemical features are described, and the structure-activity relationships are discussed. In spite of the relevance of these modifications on the distamycin frame, these derivatives showed significant growth inhibitory activity against mouse leukemia L1210 cells. Therefore, the presence of the amidino moiety, and in general of a basic moiety, is not an absolute requirement for biological activity of alpha-bromoacrylic derivatives of distamycin. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Structure-activity relationship of novel tallimustine derivatives: synthesis and antitumor activity
  作者：Pier Giovanni Baraldi、Italo Beria、Barbara Cacciari、Laura Capolongo、Paolo Cozzi、Nicola Mongelli、Romeo Romagnoli、Giampiero Spalluto

  DOI：10.1016/0960-894x(96)00205-3

  日期：1996.6

  Oligopeptide-like derivatives structurally related to the antitumor agent tallimustine, where one or two pyrrole rings were replaced by pyrazole or thiazole rings and bearing benzoyl nitrogen mustard or bromoacryloyl moieties were synthesized and evaluated in vitro and in vivo against L1210 murine leukemia. Compounds 9 and 12 showed antitumor activity higher than or comparable with that of tallimustine. Copyright (C) 1996 Elsevier Science Ltd
• DISTAMYCIN A ANALOGUES AS ANTITUMOUR OR ANTIVIRAL AGENTS
  申请人：Pharmacia Italia S.p.A.

  公开号：EP0722446B1

  公开（公告）日：2002-12-11
• US5753629A
  申请人：——

  公开号：US5753629A

  公开（公告）日：1998-05-19
• US6753316B1
  申请人：——

  公开号：US6753316B1

  公开（公告）日：2004-06-22