(+/-)-1-(tert-butyloxycarbonyl)-3-[[(methylsulfonyl)oxy]methyl]-6-nitroindoline | 185433-54-9

• 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: (+/-)-1-(tert-butyloxycarbonyl)-3-[[(methylsulfonyl)oxy]methyl]-6-nitroindoline
• 英文别名: 1-(t-butyloxycarbonyl)-3-(hydroxymethyl)-6-nitroindoline；tert-butyl 3-(hydroxymethyl)-6-nitro-2,3-dihydroindole-1-carboxylate
• CAS: 185433-54-9
• 化学式: C₁₄H₁₈N₂O₅
• 分子量: 294.307
• InChiKey: YRFIRTPJPOONQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  95.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+/-)-1-(tert-butyloxycarbonyl)-3-[[(methylsulfonyl)oxy]methyl]-6-nitroindoline 在 盐酸 、 三乙胺 、 lithium chloride 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.25h， 生成 3-(chloromethyl)-6-nitroindoline
  参考文献：
  名称：

  Tercel, Moana; Denny, William A., Journal of the Chemical Society. Perkin transactions I, 1998, # 3, p. 509 - 519

  摘要：

  DOI：
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 4-二甲氨基吡啶 、 sodium methylate 、 二异丁基氢化铝 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.35h， 生成 (+/-)-1-(tert-butyloxycarbonyl)-3-[[(methylsulfonyl)oxy]methyl]-6-nitroindoline
  参考文献：
  名称：

  Tercel, Moana; Denny, William A., Journal of the Chemical Society. Perkin transactions I, 1998, # 3, p. 509 - 519

  摘要：

  DOI：

文献信息

• Cyclopropylindoles and their seco precursors, and their use as prodrugs
  申请人：Cancer Research Campaign Technology Limited

  公开号：US05985909A1

  公开（公告）日：1999-11-16

  The present invention provides compounds of formula (I) and (II) which may be used as anticancer drugs.

  本发明提供了化合物(I)和(II)的公式，可用作抗癌药物。
• A novel nitro-substituted seco-CI: Application as a reductively activated adept prodrug
  作者：M. Tercel、W.A. Denny、W.R. Wilson

  DOI：10.1016/s0960-894x(96)00508-2

  日期：1996.11

  An alternative synthesis of seco-CI alkylating agents bearing a nitrogen substituent at C-6 is reported. The nitro compound 3 prepared by this route exhibits a 400-fold increase in cytotoxicity against UV4 cells in the presence of a nitroreductase enzyme from Escherichia coli B, suggesting it as a potential prodrug for use in antibody-directed enzyme prodrug therapy. Copyright (C) 1996 Elsevier Science Ltd
• Cytotoxicity and DNA Interaction of the Enantiomers of 6-Amino-3-(chloromethyl)-1-[(5,6,7-trimethoxyindol-2-yl)carbonyl]indoline (Amino-<i>seco</i>-CI-TMI)
  作者：Moana Tercel、Michael A. Gieseg、Jared B. Milbank、Maruta Boyd、Jun-Yao Fan、L. Karin Tan、William R. Wilson、William A. Denny

  DOI：10.1021/tx990069o

  日期：1999.8.1

  The enantiomers of the previously reported racemic 6-amino-3-(chloromethyl)-1-[(5,6,7-trimethoxyindol-2-yl)carbonyl]indoline (amino-seco-CI-TMI) were prepared via resolution of a precursor by chiral HPLC. The only detectable product isolated from reaction of the racemic compound with calf thymus DNA, followed by thermal cleavage, was shown by mass spectrometry and two-dimensional NMR spectroscopy to be the adenine N3 adduct. Polyacrylamide gel electrophoresis assays with the racemate and with each enantiomer also showed adenine to be the only site of alkylation. While the racemic amino compound exhibited sequence selectivity identical to that of the previously characterized phenol analogue, the enantiomers exhibited distinctly different sequence selectivities, allowing the (+) enantiomer to be assigned the "natural" S configuration. The (+)-(S) enantiomer is 3-fold more cytotoxic than the (-)-(R) enantiomer (IC50 values of 240 and 700 nM, respectively, in AA8 cells, after exposure for 4 h).
• CYCLOPROPYLINDOLES AND THEIR SECO PRECURSORS, AND THEIR USE AS PRODRUGS
  申请人：AUCKLAND DIVISION CANCER SOCIETY OF NEW ZEALAND INC.

  公开号：EP0850220A1

  公开（公告）日：1998-07-01
• US5985909A
  申请人：——

  公开号：US5985909A

  公开（公告）日：1999-11-16