(2S)-N-{4-[N-(1''-pyrenyl)-butane-4'-carboxamide]-oxy-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal | 678154-63-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: (2S)-N-{4-[N-(1''-pyrenyl)-butane-4'-carboxamide]-oxy-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal
• CAS: 678154-63-7
• 化学式: C₃₈H₄₁N₃O₆S₂
• 分子量: 699.892
• InChiKey: DOQSRFOFWAZDOQ-PMERELPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.13
• 重原子数：
  49.0
• 可旋转键数：
  15.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  111.01
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (2S)-N-{4-[N-(1''-pyrenyl)-butane-4'-carboxamide]-oxy-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal 在 calcium carbonate 、 mercury dichloride 、 tin(ll) chloride 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 17.0h， 生成 7-methoxy-8-[N-(1''-pyrenyl)-butane-4'-carboxamide]-oxy-(11aS)-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one
  参考文献：
  名称：

  Synthesis and antitumour activity of pyrene-linked pyrrolo [2,1-c]benzodiazepine hybrids

  摘要：

  Pyrene-linked pyrrolobenzodiazepine hybrids have been synthesized that exhibit potential anticancer activity in a number of human tumour cell lines. These hybrids also exhibit much enhanced DNA-binding ability in comparison to the parent pyrrolobenzodiazepine ring system (DC-81). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.10.050
• 作为产物：
  描述：

  1-硝基芘 在 三乙胺 、 tin(ll) chloride 、 氯甲酸异丁酯 作用下， 以 乙酸乙酯 为溶剂， 反应 17.0h， 生成 (2S)-N-{4-[N-(1''-pyrenyl)-butane-4'-carboxamide]-oxy-5-methoxy-2-nitrobenzoyl}pyrrolidine-2-carboxaldehyde diethyl thioacetal
  参考文献：
  名称：

  Synthesis and antitumour activity of pyrene-linked pyrrolo [2,1-c]benzodiazepine hybrids

  摘要：

  Pyrene-linked pyrrolobenzodiazepine hybrids have been synthesized that exhibit potential anticancer activity in a number of human tumour cell lines. These hybrids also exhibit much enhanced DNA-binding ability in comparison to the parent pyrrolobenzodiazepine ring system (DC-81). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.10.050

文献信息

• PYRENE-LINKED PYRROLO[2,1--C][1,4]BENZODIAZEPINE HYBRIDS USEFUL AS ANTI-CANCER AGENTS
  申请人：COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH

  公开号：US20040192677A1

  公开（公告）日：2004-09-30

  The present invention relates to a process for the preparation of novel pyrrolo [2,1 -c][1,4]benzodiazepine hybrids useful as antitumour agents. This invention also relates to a process for the preparation of new pyrrolo[2,1-c][1,4]benzodiazepine hybrids as potential antitumour agents. More particularly, it provides a process for the preparation of 7-methoxy-8-[N-(1″-pyrenyl)-alkane-3′-carboxamide]-oxy-(11aS)-1,2,3,11a-tetraydro 5H-pyrrolo[2,1 -c][1,4]benzodiazepin-5-one, with aliphatic chain length variation of these compounds and it also describes the DNA binding, aticancer (antitumour) activity. The structral formula of this novel pyrrolo[2,1-c][1,4]benzodiazepine is given below: 1

  本发明涉及一种制备新型吡咯并[2,1-c][1,4]苯二氮平杂化物的过程，该杂化物可用作抗肿瘤药物。本发明还涉及一种制备新型吡咯并[2,1-c][1,4]苯二氮平杂化物的过程，作为潜在的抗肿瘤药物。更具体地，它提供了一种制备7-甲氧基-8-[N-(1″-芘基)-烷基-3′-羧酰胺]-氧-(11aS)-1,2,3,11a-四氢-5H-吡咯并[2,1-c][1,4]苯并噻唑-5-酮的过程，这些化合物的脂肪链长度变化，以及它还描述了DNA结合，抗癌（抗肿瘤）活性。这种新型吡咯并[2,1-c][1,4]苯二氮平杂化物的结构式如下：1