(+)-(1R)-1,2-dihydro-1-(hydroxymethyl)-3-(tert-butyloxycarbonyl)-5-(benzyloxy)-8-methyl-3H-furano<3,2-e>indole | 153001-70-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (+)-(1R)-1,2-dihydro-1-(hydroxymethyl)-3-(tert-butyloxycarbonyl)-5-(benzyloxy)-8-methyl-3H-furano<3,2-e>indole
• 英文别名: tert-butyl (8S)-8-(hydroxymethyl)-1-methyl-4-phenylmethoxy-7,8-dihydrofuro[3,2-e]indole-6-carboxylate
• CAS: 153001-70-8
• 化学式: C₂₄H₂₇NO₅
• 分子量: 409.482
• InChiKey: NNJQXYASQHHLRO-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  72.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+)-(1R)-1,2-dihydro-1-(hydroxymethyl)-3-(tert-butyloxycarbonyl)-5-(benzyloxy)-8-methyl-3H-furano<3,2-e>indole 在 盐酸 、 四氯化碳 、 palladium on activated charcoal 、 甲酸铵 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 3.0h， 生成 (S)-8-Chloromethyl-1-methyl-7,8-dihydro-6H-furo[3,2-e]indol-4-ol
  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：

  1-(1-(1-oxa-2-butenyl))-2-methoxy-4-nitrobenzene 在 platinum(IV) oxide sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 PPA 、 二甲基硫 、 偶氮二异丁腈 、 硫酸 、 氢气 、 双氧水 、 三正丁基氢锡 、 吡啶盐酸盐 、 sodium hydride 、 臭氧 、 (-)-Monoisopinocampheylborane 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， -78.0~180.0 ℃ 、137.9 kPa 条件下， 反应 37.91h， 生成 (+)-(1R)-1,2-dihydro-1-(hydroxymethyl)-3-(tert-butyloxycarbonyl)-5-(benzyloxy)-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

文献信息

• Total synthesis and biological properties of novel antineoplastic (chloromethyl)furanoindolines: an asymmetric hydroboration mediated synthesis of the alkylation subunits
  作者：Fariborz Mohamadi、Michael M. Spees、Gilbert S. Staten、Philip Marder、Julia K. Kipka、David A. Johnson、Dale L. Boger、Hamideh Zarrinmayeh

  DOI：10.1021/jm00028a005

  日期：1994.1

  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.