bis(prop-2-enyl) (2S)-2-[[4-[[2-[(2S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl]-4,5-dimethoxyphenyl]carbamoyloxymethyl]phenyl]carbamoylamino]pentanedioate | 848004-45-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: bis(prop-2-enyl) (2S)-2-[[4-[[2-[(2S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl]-4,5-dimethoxyphenyl]carbamoyloxymethyl]phenyl]carbamoylamino]pentanedioate
• CAS: 848004-45-5
• 化学式: C₃₄H₄₂N₄O₁₁
• 分子量: 682.728
• InChiKey: IXPDVOMAHJUDOL-AHWVRZQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  49
• 可旋转键数：
  20
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  191
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  bis(prop-2-enyl) (2S)-2-[[4-[[2-[(2S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl]-4,5-dimethoxyphenyl]carbamoyloxymethyl]phenyl]carbamoylamino]pentanedioate 在 重铬酸吡啶 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以57%的产率得到bis(prop-2-enyl) (2S)-2-[[4-[[(6S,6aS)-6-hydroxy-2,3-dimethoxy-11-oxo-6a,7,8,9-tetrahydro-6H-pyrrolo[2,1-c][1,4]benzodiazepine-5-carbonyl]oxymethyl]phenyl]carbamoylamino]pentanedioate
  参考文献：
  名称：

  Synthesis and biological evaluation of novel pyrrolo[2,1-c][1,4]benzodiazepine prodrugs for use in antibody-directed enzyme prodrug therapy

  摘要：

  The design, synthesis and evaluation of four novel pyrrolo[2,1-c][1,4]benzodiazepine (PBD) prodrugs (1a,b and 2a,b; Fig. 1) for potential use in carboxypeptidase G2 (CPG2)-based anti body-directed enzyme prodrug therapy (ADEPT) is reported. Although all four prodrugs were shown to be less cytotoxic than the released parent PBDs 3 and 4, the urea prodrugs 1b and 2b were found to be too unstable for use in ADEPT, whereas carbamates 1a and 2a are both stable in an aqueous environment and are good substrates for CPG2. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.017
• 作为产物：
  描述：

  [(2S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]pyrrolidin-1-yl]-(2-isocyanato-4,5-dimethoxyphenyl)methanone 在 TEA 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 bis(prop-2-enyl) (2S)-2-[[4-[[2-[(2S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl]-4,5-dimethoxyphenyl]carbamoyloxymethyl]phenyl]carbamoylamino]pentanedioate
  参考文献：
  名称：

  Synthesis and biological evaluation of novel pyrrolo[2,1-c][1,4]benzodiazepine prodrugs for use in antibody-directed enzyme prodrug therapy

  摘要：

  The design, synthesis and evaluation of four novel pyrrolo[2,1-c][1,4]benzodiazepine (PBD) prodrugs (1a,b and 2a,b; Fig. 1) for potential use in carboxypeptidase G2 (CPG2)-based anti body-directed enzyme prodrug therapy (ADEPT) is reported. Although all four prodrugs were shown to be less cytotoxic than the released parent PBDs 3 and 4, the urea prodrugs 1b and 2b were found to be too unstable for use in ADEPT, whereas carbamates 1a and 2a are both stable in an aqueous environment and are good substrates for CPG2. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.017

文献信息

• SYNTHESIS OF PROTECTED PYRROLOBENZODIAZEPINES
  申请人：Spirogen Limited

  公开号：EP1664049B1

  公开（公告）日：2009-12-23
• US7429658B2
  申请人：——

  公开号：US7429658B2

  公开（公告）日：2008-09-30