(11aS)-7-methoxy-8-[4-(4-(9-phenanthryl)phenoxy)butyl]oxy-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one | 1187208-95-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (11aS)-7-methoxy-8-[4-(4-(9-phenanthryl)phenoxy)butyl]oxy-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one
• 英文别名: (11aS)-7-methoxy-8-4-[4-(9-phenanthryl)phenoxy]butoxy-2,3,5,11a-tetrahydro-1H-benzo[e]pyrrolo[1,2-a][1,4]diazepin-5-one；(6aS)-2-methoxy-3-[4-(4-phenanthren-9-ylphenoxy)butoxy]-6a,7,8,9-tetrahydropyrrolo[2,1-c][1,4]benzodiazepin-11-one
• CAS: 1187208-95-2
• 化学式: C₃₇H₃₄N₂O₄
• 分子量: 570.688
• InChiKey: MLKFHWANYFGSIM-MHZLTWQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  43
• 可旋转键数：
  9
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (2S)-N-[4-(4-bromobutyl)oxy-5-methoxy-2-nitrobenzoyl]pyrrolidine-2-carboxaldehyde diethylthioacetal 在 tin(II) chloride dihdyrate 、 potassium carbonate 、 calcium carbonate 、 mercury dichloride 作用下， 以 甲醇 、 水 、 丙酮 、 乙腈 为溶剂， 反应 48.0h， 生成 (11aS)-7-methoxy-8-[4-(4-(9-phenanthryl)phenoxy)butyl]oxy-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one
  参考文献：
  名称：

  [EN] NEW PHENANTHRYLPHENOL LINKED PYRROLO[2,L-NOUVEAUX HYBRIDES DE PYRROLO[2,1-20090917US2005222133A1KAMAL AHMED [IN], et al20051006AA1-6AAHMED KAMAL, G. RAMESH, O. SRINIVAS AND P. RAMULU: "Synthesis and antitumour activity of pyrene-linked pyrrolo[2,1-c][1,4]benzodiazepine hybrids", BIOORGANIC AND MEDICINAL CHEMISTRY LETTERS, vol. 14, no. 2, 3 December 2003 (2003-12-03), pages 471 - 474, XP002540982AHMED KAMAL, G. RAMESH, O. SRINIVAS AND P. RAMULUSynthesis and antitumour activity of pyrene-linked pyrrolo[2,1-c][1,4]benzodiazepine hybridsBIOORGANIC AND MEDICINAL CHEMISTRY LETTERS2003120314247147447111826A1-6A
  [FR] NOUVEAUX HYBRIDES DE PYRROLO[2,1-20090917US2005222133A1KAMAL AHMED [IN], et al20051006AA1-6AAHMED KAMAL, G. RAMESH, O. SRINIVAS AND P. RAMULU: "Synthesis and antitumour activity of pyrene-linked pyrrolo[2,1-c][1,4]benzodiazepine hybrids", BIOORGANIC AND MEDICINAL CHEMISTRY LETTERS, vol. 14, no. 2, 3 December 2003 (2003-12-03), pages 471 - 474, XP002540982AHMED KAMAL, G. RAMESH, O. SRINIVAS AND P. RAMULUSynthesis and antitumour activity of pyrene-linked pyrrolo[2,1-c][1,4]benzodiazepine hybridsBIOORGANIC AND MEDICINAL CHEMISTRY LETTERS2003120314247147447111826A1-6A

  摘要：

  本发明提供了一种通式（6）的化合物，可作为潜在的抗人类癌细胞系肿瘤药物。本发明还提供了一种制备通式（6）的吡咯并[2,1-c][1,4]苯并二氮杂环烃混合物的方法。

  公开号：

  WO2009113109A1

文献信息

• Synthesis and potential cytotoxic activity of new phenanthrylphenol-pyrrolobenzodiazepines
  作者：Ahmed Kamal、Kokkonda Sreekanth、P. Praveen Kumar、Nagula Shankaraiah、G. Balakishan、M. Janaki Ramaiah、S.N.C.V.L. Pushpavalli、Paramita Ray、Manika Pal Bhadra

  DOI：10.1016/j.ejmech.2010.01.054

  日期：2010.6

  New phenanthrylphenol-pyrrolobenzodiazepine (PP-PBD) conjugates have been synthesized and evaluated for their biological activity. One of the compounds 4a has been evaluated for its antiproliferative activity on 57 human tumour cell lines. The growth inhibition of 4a–c has been determined by MTT viability assay on MCF-7 cell line. Among them, 4c showed most potent growth inhibition. Based on this,

  已经合成了新的菲基酚-吡咯并苯并二氮杂（PP-PBD）缀合物，并对其生物学活性进行了评估。已经评估了化合物4a之一对57种人肿瘤细胞系的抗增殖活性。通过MCT-7细胞系的MTT活力测定已确定了4a – c的生长抑制。其中，4c显示出最有效的生长抑制作用。在此基础上，尝试通过细胞周期分析和DNA相互作用研究使它们的作用机理合理化。铅化合物4c对MCF-7细胞生长的影响与细胞周期停滞在G1期有关，随后是细胞凋亡。我们的发现表明，菲基酚-PBD共轭物作为细胞周期蛋白D1抑制剂的4c可以被认为是抗乳腺癌的有前途的先导化合物，有待进一步研究。
• NEW PHENANTHRYLPHENOL LINKED PYRROLO[2,1-C][1,4]BENZODIAZEPINE HYBRIDS AS POTENTIAL ANTITUMOUR AGENTS AND PROCESS FOR THE PREPARATION THEREOF
  申请人：Council of Scientific & Industrial Research

  公开号：EP2294070B1

  公开（公告）日：2011-10-05
• NEW PHENANTHRYLPHENOL LINKED PYRROLO [2, L-C] [L, 4] BENZODIAZEPINE HYBRIDS AS POTENTIAL ANTITUMOUR AGENTS AND PROCESS FOR THE PREPARATION THEREOF
  申请人：Ahmed Kamal

  公开号：US20110207924A1

  公开（公告）日：2011-08-25

  The present invention provides a compounds of general formula (6), useful as potential antitumour agents against human cancer cell lines. The present invention further provides a process for the preparation of pyrrolo[2,1-c][1,4]benzodiazepine hybrids of general formula (6).
• US8217167B2
  申请人：——

  公开号：US8217167B2

  公开（公告）日：2012-07-10
• [EN] NEW PHENANTHRYLPHENOL LINKED PYRROLO[2,L-NOUVEAUX HYBRIDES DE PYRROLO[2,1-20090917US2005222133A1KAMAL AHMED [IN], et al20051006AA1-6AAHMED KAMAL, G. RAMESH, O. SRINIVAS AND P. RAMULU: "Synthesis and antitumour activity of pyrene-linked pyrrolo[2,1-c][1,4]benzodiazepine hybrids", BIOORGANIC AND MEDICINAL CHEMISTRY LETTERS, vol. 14, no. 2, 3 December 2003 (2003-12-03), pages 471 - 474, XP002540982AHMED KAMAL, G. RAMESH, O. SRINIVAS AND P. RAMULUSynthesis and antitumour activity of pyrene-linked pyrrolo[2,1-c][1,4]benzodiazepine hybridsBIOORGANIC AND MEDICINAL CHEMISTRY LETTERS2003120314247147447111826A1-6A<br/>[FR] NOUVEAUX HYBRIDES DE PYRROLO[2,1-20090917US2005222133A1KAMAL AHMED [IN], et al20051006AA1-6AAHMED KAMAL, G. RAMESH, O. SRINIVAS AND P. RAMULU: "Synthesis and antitumour activity of pyrene-linked pyrrolo[2,1-c][1,4]benzodiazepine hybrids", BIOORGANIC AND MEDICINAL CHEMISTRY LETTERS, vol. 14, no. 2, 3 December 2003 (2003-12-03), pages 471 - 474, XP002540982AHMED KAMAL, G. RAMESH, O. SRINIVAS AND P. RAMULUSynthesis and antitumour activity of pyrene-linked pyrrolo[2,1-c][1,4]benzodiazepine hybridsBIOORGANIC AND MEDICINAL CHEMISTRY LETTERS2003120314247147447111826A1-6A
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2009113109A1

  公开（公告）日：2009-09-17

  The present invention provides a compounds of general formula (6), useful as potential antitumour agents against human cancer cell lines. The present invention further provides a process for the preparation of pyrrolo [2,1-c] [l,4]benzodiazepine hybrids of general formula (6).

  本发明提供了一种通式（6）的化合物，可作为潜在的抗人类癌细胞系肿瘤药物。本发明还提供了一种制备通式（6）的吡咯并[2,1-c][1,4]苯并二氮杂环烃混合物的方法。