[3-(4-methoxyphenyl)-5,10-dihydropyrrolo[1,2-b]isoquinoline-1,2-diyl]bis(methylene) bis(iso-propylcarbamate) | 1262971-99-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: [3-(4-methoxyphenyl)-5,10-dihydropyrrolo[1,2-b]isoquinoline-1,2-diyl]bis(methylene) bis(iso-propylcarbamate)
• 英文别名: [3-(4-methoxyphenyl)-2-(propan-2-ylcarbamoyloxymethyl)-5,10-dihydropyrrolo[1,2-b]isoquinolin-1-yl]methyl N-propan-2-ylcarbamate
• CAS: 1262971-99-2
• 化学式: C₂₉H₃₅N₃O₅
• 分子量: 505.614
• InChiKey: GJWLYONOXCRYMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  90.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  [3-(4-methoxyphenyl)-5,10-dihydropyrrolo[1,2-b]isoquinoline-1,2-diyl]dimethanol 、 异氰酸异丙酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以65%的产率得到[3-(4-methoxyphenyl)-5,10-dihydropyrrolo[1,2-b]isoquinoline-1,2-diyl]bis(methylene) bis(iso-propylcarbamate)
  参考文献：
  名称：

  Novel bifunctional alkylating agents, 5,10-dihydropyrrolo[1,2-b]isoquinoline derivatives, synthesis and biological activity

  摘要：

  A series of linear pyrrolo[1,2-b]isoquinoline derivatives was synthesized for antitumor evaluation. The preliminary antitumor studies reveal that both bis(hydroxymethyl) and their bis(alkylcarbamate) derivatives show significant antitumor activity in inhibiting various human tumor cell growth in vitro. 1,2-Bis(hydroxymethyl)-3-methyl-5,10-dihydropyrrolo[1,2-b] isoquinoline (20a) was selected for antitumor studies in animal models. The results show that this agent can induce complete tumor remission or significant suppression in nude mice bearing human breast (MX-1) xenograft and ovarian (SK-OV-3) xenografts, respectively. Alkaline agarose gel shifting assay showed that 20a is able to cross-link with DNA. Studies on the cell cycle inhibition revealed that this agent induces cell arrest at G2/M phase. The results warrant further antitumor investigation against other human tumor growth in animal models. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.030

文献信息

• Novel bifunctional alkylating agents, 5,10-dihydropyrrolo[1,2-b]isoquinoline derivatives, synthesis and biological activity
  作者：Ravi Chaniyara、Naval Kapuriya、Huajin Dong、Pei-Chih Lee、Sharda Suman、Bhavin Marvania、Ting-Chao Chou、Te-Chang Lee、Rajesh Kakadiya、Anamik Shah、Tsann-Long Su

  DOI：10.1016/j.bmc.2010.11.030

  日期：2011.1

  A series of linear pyrrolo[1,2-b]isoquinoline derivatives was synthesized for antitumor evaluation. The preliminary antitumor studies reveal that both bis(hydroxymethyl) and their bis(alkylcarbamate) derivatives show significant antitumor activity in inhibiting various human tumor cell growth in vitro. 1,2-Bis(hydroxymethyl)-3-methyl-5,10-dihydropyrrolo[1,2-b] isoquinoline (20a) was selected for antitumor studies in animal models. The results show that this agent can induce complete tumor remission or significant suppression in nude mice bearing human breast (MX-1) xenograft and ovarian (SK-OV-3) xenografts, respectively. Alkaline agarose gel shifting assay showed that 20a is able to cross-link with DNA. Studies on the cell cycle inhibition revealed that this agent induces cell arrest at G2/M phase. The results warrant further antitumor investigation against other human tumor growth in animal models. (C) 2010 Elsevier Ltd. All rights reserved.