3-methyl-4-bromo-5-(N-(tert-butyloxycarbonyl)-N-(2-propyn-1-yl)amino)-7-(benzyloxy)benzofuran | 153001-69-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 3-methyl-4-bromo-5-(N-(tert-butyloxycarbonyl)-N-(2-propyn-1-yl)amino)-7-(benzyloxy)benzofuran
• 英文别名: 3-methyl-4-bromo-5-(N-(t-butyloxycarbonyl)-N-(2-propyn-1yl))amino-7-(benzyloxy)benzofuran；tert-butyl N-(4-bromo-3-methyl-7-phenylmethoxy-1-benzofuran-5-yl)-N-prop-2-ynylcarbamate
• CAS: 153001-69-5
• 化学式: C₂₄H₂₄BrNO₄
• 分子量: 470.363
• InChiKey: DSZMGWBFGDHPCF-UHFFFAOYSA-N

物化性质

• 沸点：
  558.3±50.0 °C(predicted)
• 密度：
  1.352±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  51.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-methyl-4-bromo-5-(N-(tert-butyloxycarbonyl)-N-(2-propyn-1-yl)amino)-7-(benzyloxy)benzofuran 在 盐酸 、 四氯化碳 、 sodium hydroxide 、 palladium on activated charcoal 、 偶氮二异丁腈 、 双氧水 、 三正丁基氢锡 、 甲酸铵 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三苯基膦 、 (-)-Monoisopinocampheylborane 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 30.91h， 生成 (+)-(1R)-1,2-dihydro-1-(chloromethyl)-3-((5-((benzofuran-2-ylcarbonyl)amino)-1H-indol-2-yl)carbonyl)-5-hydroxy-8-methyl-3H-furano<3,2-e>indole
  参考文献：
  名称：

  Total synthesis and biological properties of novel antineoplastic (chloromethyl)furanoindolines: an asymmetric hydroboration mediated synthesis of the alkylation subunits

  摘要：

  1,2-Dihydro-1-(chloromethyl)-5-hydroxy-8-methyl-3H-furano[3,2-e] indole (CFI) as a novel re; placement of the cyclopropylpyrroloindoline (CPI) alkylation subunit of CC-1065, U-71184, and U-73975 (adozelesin) has been synthesized and incorporated into a series of efficacious antineopIastic agents. A partial solution to an asymmetric synthesis of the CFI alkylation subunit has been achieved by the implementation of an asymmetric hydroboration reaction of an intermediate 3-methyleneindoline (13). Extension to the asymmetric synthesis of the CBI and CI alkylation subunits is presented. The demonstration and comparative study of the sequence-selective DNA alkylation properties of the CFI-based agents are detailed, and the preliminary in vitro and in vivo antineoplastic propertes of these agents in the human epidermoid cell lung carcinoma (T222) are described.

  DOI：

  10.1021/jm00028a005
• 作为产物：
  描述：

  3-methyl-5-(N-(tert-butyloxycarbonyl)amino)-7-(benzyloxy)benzofuran 在 N-溴代丁二酰亚胺(NBS) 、 硫酸 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 8.0h， 生成 3-methyl-4-bromo-5-(N-(tert-butyloxycarbonyl)-N-(2-propyn-1-yl)amino)-7-(benzyloxy)benzofuran
  参考文献：
  名称：

  Total synthesis and biological properties of novel antineoplastic (chloromethyl)furanoindolines: an asymmetric hydroboration mediated synthesis of the alkylation subunits

  摘要：

  1,2-Dihydro-1-(chloromethyl)-5-hydroxy-8-methyl-3H-furano[3,2-e] indole (CFI) as a novel re; placement of the cyclopropylpyrroloindoline (CPI) alkylation subunit of CC-1065, U-71184, and U-73975 (adozelesin) has been synthesized and incorporated into a series of efficacious antineopIastic agents. A partial solution to an asymmetric synthesis of the CFI alkylation subunit has been achieved by the implementation of an asymmetric hydroboration reaction of an intermediate 3-methyleneindoline (13). Extension to the asymmetric synthesis of the CBI and CI alkylation subunits is presented. The demonstration and comparative study of the sequence-selective DNA alkylation properties of the CFI-based agents are detailed, and the preliminary in vitro and in vivo antineoplastic propertes of these agents in the human epidermoid cell lung carcinoma (T222) are described.

  DOI：

  10.1021/jm00028a005

文献信息

• Furanoindolines
  申请人：Eli Lilly and Company

  公开号：US05248691A1

  公开（公告）日：1993-09-28

  This invention provides novel furanoindoline compounds effective in inhibiting the growth of solid tumors.

  这项发明提供了一种新型的呋喃吲哚衍生物化合物，能够有效抑制实体肿瘤的生长。
• Furanoindoline derivatives and their use as antitumor agents
  申请人：ELI LILLY AND COMPANY

  公开号：EP0586254A1

  公开（公告）日：1994-03-09

  This invention provides novel furanoindoline compounds of formula I effective in inhibiting the growth of solid tumors.

  本发明提供了有效抑制实体瘤生长的新型式 I 呋喃吲哚啉化合物。
• US5248691A
  申请人：——

  公开号：US5248691A

  公开（公告）日：1993-09-28