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[6-methyl-3-phenyl-6,11-dihydro-5H-indolizino [6,7-b]indole-1,2-diyl]bis(methylene)bis(ethylcarbamate) | 1422377-14-7

中文名称
——
中文别名
——
英文名称
[6-methyl-3-phenyl-6,11-dihydro-5H-indolizino [6,7-b]indole-1,2-diyl]bis(methylene)bis(ethylcarbamate)
英文别名
[6-methyl-3-phenyl-6,11-dihydro-5H-indolizino[6,7-b]indole-1,2-diyl]bis(methylene) bis(ethylcarbamate);BO-1941;[2-(ethylcarbamoyloxymethyl)-9-methyl-1-phenyl-4,10-dihydroindolizino[6,7-b]indol-3-yl]methyl N-ethylcarbamate
[6-methyl-3-phenyl-6,11-dihydro-5H-indolizino [6,7-b]indole-1,2-diyl]bis(methylene)bis(ethylcarbamate)化学式
CAS
1422377-14-7
化学式
C29H32N4O4
mdl
——
分子量
500.597
InChiKey
YNFQXRIVCPPBGY-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    3.8
  • 重原子数:
    37
  • 可旋转键数:
    9
  • 环数:
    5.0
  • sp3杂化的碳原子比例:
    0.31
  • 拓扑面积:
    86.5
  • 氢给体数:
    2
  • 氢受体数:
    4

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为产物:
    描述:
    methyl (3S)-1,2,3,4-tetrahydro-β-carboline-3-carboxylate 在 lithium aluminium tetrahydride 、 乙酸酐 、 sodium hydride 、 三乙胺 作用下, 以 四氢呋喃乙醚二氯甲烷 、 mineral oil 为溶剂, 反应 18.75h, 生成 [6-methyl-3-phenyl-6,11-dihydro-5H-indolizino [6,7-b]indole-1,2-diyl]bis(methylene)bis(ethylcarbamate)
    参考文献:
    名称:
    Novel Antitumor Indolizino[6,7-b]indoles with Multiple Modes of Action: DNA Cross-Linking and Topoisomerase I and II Inhibition
    摘要:
    A series of bis(hydroxymethyl)indolizino[6,7-b]indoles and their bis(alkylcarbamates) were synthesized for antitumor studies. These agents were designed as hybrid molecules of beta-carboline (topoisomerase inhibition moiety) and bis(hydroxymethyl)pyrrole (DNA cross-linking moiety). The preliminary antitumor studies indicated that these agents exhibited significant cytotoxicity against a variety of human tumor cells in vitro. Treatment of human breast carcinoma MX-1 xenograft-bearing nude mice with compounds 18b and 28c achieved more than 99% tumor remission. We also observed that 18a displayed potent therapeutic efficacy against human lung adenocarcinoma A549 and colon cancer HT 29 xenografts. These results revealed that compound 18a was more potent than irinotecan against HT 29 cells and was as potent as irinotecan against A549 cells in xenograft models. Furthermore, we demonstrated that these derivatives possess multiple modes of action, such as induction of DNA cross-linking, inhibition of topoisomerase I and II, and cell-cycle arrest at the S-phase.
    DOI:
    10.1021/jm301788a
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文献信息

  • METHODS FOR TREATING SMALL CELL LUNG CANCERS BY USING PHARMACEUTICAL COMPOSITIONS OR COMBINATIONS COMPRISING INDOLIZINO[6,7-B]INDOLE DERIVATIVES
    申请人:SU Tsann-Long
    公开号:US20190247371A1
    公开(公告)日:2019-08-15
    A method for treating small cell lung cancer (SCLC). In the method, a therapeutically effective amount of a compound of Formula I: wherein R 1 , R 2 and R 3 have the definitions disclosed in the specification is administered alone or in combination with one or more anticancer agents, or surgery, radiation therapy, chemotherapy, and/or targeted therapy.
  • US8703951B2
    申请人:——
    公开号:US8703951B2
    公开(公告)日:2014-04-22
  • Novel Antitumor Indolizino[6,7-<i>b</i>]indoles with Multiple Modes of Action: DNA Cross-Linking and Topoisomerase I and II Inhibition
    作者:Ravi Chaniyara、Satishkumar Tala、Chi-Wei Chen、Xiuguo Zang、Rajesh Kakadiya、Li-Fang Lin、Ching-Huang Chen、Shin-I Chien、Ting-Chao Chou、Tung-Hu Tsai、Te-Chang Lee、Anamik Shah、Tsann-Long Su
    DOI:10.1021/jm301788a
    日期:2013.2.28
    A series of bis(hydroxymethyl)indolizino[6,7-b]indoles and their bis(alkylcarbamates) were synthesized for antitumor studies. These agents were designed as hybrid molecules of beta-carboline (topoisomerase inhibition moiety) and bis(hydroxymethyl)pyrrole (DNA cross-linking moiety). The preliminary antitumor studies indicated that these agents exhibited significant cytotoxicity against a variety of human tumor cells in vitro. Treatment of human breast carcinoma MX-1 xenograft-bearing nude mice with compounds 18b and 28c achieved more than 99% tumor remission. We also observed that 18a displayed potent therapeutic efficacy against human lung adenocarcinoma A549 and colon cancer HT 29 xenografts. These results revealed that compound 18a was more potent than irinotecan against HT 29 cells and was as potent as irinotecan against A549 cells in xenograft models. Furthermore, we demonstrated that these derivatives possess multiple modes of action, such as induction of DNA cross-linking, inhibition of topoisomerase I and II, and cell-cycle arrest at the S-phase.
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