tert-butyl 1-methyl-5-[({1-methyl-5-[({1-methyl-5-[(2-oxo-1-imidazolidinyl)carbonyl]-1H-pyrrol-3-yl}amino)carbonyl]-1H-pyrrol-3-yl}amino)carbonyl]-1H-pyrrol-3-ylcarbamate | 386704-68-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: tert-butyl 1-methyl-5-[({1-methyl-5-[({1-methyl-5-[(2-oxo-1-imidazolidinyl)carbonyl]-1H-pyrrol-3-yl}amino)carbonyl]-1H-pyrrol-3-yl}amino)carbonyl]-1H-pyrrol-3-ylcarbamate
• 英文别名: tert-butyl N-[1-methyl-5-[[1-methyl-5-[[1-methyl-5-(2-oxoimidazolidine-1-carbonyl)pyrrol-3-yl]carbamoyl]pyrrol-3-yl]carbamoyl]pyrrol-3-yl]carbamate
• CAS: 386704-68-3
• 化学式: C₂₆H₃₂N₈O₆
• 分子量: 552.59
• InChiKey: YCKPFOADEMKJNR-UHFFFAOYSA-N

物化性质

• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  161
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl 1-methyl-5-[({1-methyl-5-[({1-methyl-5-[(2-oxo-1-imidazolidinyl)carbonyl]-1H-pyrrol-3-yl}amino)carbonyl]-1H-pyrrol-3-yl}amino)carbonyl]-1H-pyrrol-3-ylcarbamate 在 sodium hydroxide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 4-amino-N-[5-[[5-[2-(diaminomethylideneamino)ethylcarbamoyl]-1-methylpyrrol-3-yl]carbamoyl]-1-methylpyrrol-3-yl]-1-methylpyrrole-2-carboxamide
  参考文献：
  名称：

  Syntheses of brostallicin starting from distamycin A

  摘要：

  Two syntheses of brostallicin, a DNA minor groove binder now undergoing phase II studies, starting from distamycin A are described. One approach is based upon the selective hydrolysis via imide activation of the C-terminus amide. Besides employing traditional solution-phase synthesis, the convenient use of a polymer-supported reagent is also discussed. The other one is based upon the Curtius rearrangement of the C-terminus side chain of a convenient intermediate, easily prepared in two steps by straightforward functional group manipulation of distamycin A. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01733-1
• 作为产物：
  描述：

  N-({4-[({4-[({4-[(tert-butoxycarbonyl)amino]-1-methyl-1H-pyrrol-2-yl}carbonyl)amino]-1-methyl-1H-pyrrol-2-yl}carbonyl)amino]-1-methyl-1H-pyrrol-2-yl}carbonyl)-beta-alanine 在 二苯基磷酸 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以65%的产率得到tert-butyl 1-methyl-5-[({1-methyl-5-[({1-methyl-5-[(2-oxo-1-imidazolidinyl)carbonyl]-1H-pyrrol-3-yl}amino)carbonyl]-1H-pyrrol-3-yl}amino)carbonyl]-1H-pyrrol-3-ylcarbamate
  参考文献：
  名称：

  Syntheses of brostallicin starting from distamycin A

  摘要：

  Two syntheses of brostallicin, a DNA minor groove binder now undergoing phase II studies, starting from distamycin A are described. One approach is based upon the selective hydrolysis via imide activation of the C-terminus amide. Besides employing traditional solution-phase synthesis, the convenient use of a polymer-supported reagent is also discussed. The other one is based upon the Curtius rearrangement of the C-terminus side chain of a convenient intermediate, easily prepared in two steps by straightforward functional group manipulation of distamycin A. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)01733-1

文献信息

• Process for preparing distamycin derivatives
  申请人：——

  公开号：US20040082759A1

  公开（公告）日：2004-04-29

  Compounds which are &agr;-halogenoacryloyl distamycin derivatives of formula (I) wherein R 1 is a bromine or chlorine atom; R 2 is a distamycin or distamycin-like framework as set forth in the specification; or a pharmaceutically acceptable salt thereof; are cytotoxic agents particularly effective in the treatment of tumors over expressing GSH/GSTs system and which are poorly responsive or even resistant to conventional antitumor therapies.

  公式（I）中的α-卤代丙烯酰基二氨基链霉素衍生物，其中R1是溴或氯原子；R2是按规范所述的二氨基链霉素或类似二氨基链霉素框架；或其药学上可接受的盐；是细胞毒剂，特别是对于在GSH/GST系统过度表达且对传统抗肿瘤治疗反应不佳甚至耐药的肿瘤的治疗非常有效。
• [EN] PROCESS FOR PREPARING DISTAMYCIN DERIVATIVES<br/>[FR] PROCÉDÉ DE PRÉPARATION DE DÉRIVÉS DE DISTAMYCINE
  申请人：PHARMACIA & UPJOHN SPA

  公开号：WO2002002523A1

  公开（公告）日：2002-01-10

  A process for preparing distamycin derivatives possessing antitumor activity, by starting from distamycin A itself, is described. The process involves the preparation of the novel intermediates of formula (III).

  本发明涉及从distamycin A出发制备具有抗肿瘤活性的distamycin衍生物的方法。该方法涉及制备公式（III）的新型中间体。
• PROCESS FOR PREPARING DISTAMYCIN DERIVATIVES
  申请人：Pharmacia Italia S.p.A.

  公开号：EP1324983A1

  公开（公告）日：2003-07-09
• US6951951B2
  申请人：——

  公开号：US6951951B2

  公开（公告）日：2005-10-04