5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-chloromethyl-7-acetylamino-1,2-dihydro-3H-benz[e]indole | 261763-56-8

• 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: 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-chloromethyl-7-acetylamino-1,2-dihydro-3H-benz[e]indole
• 英文别名: 7-acetylamino-5-benzyloxy-1-chloromethyl-1,2-dihydrobenzo[e]indole-3-carboxylic acid tert-butyl ester；Tert-butyl 7-acetamido-1-(chloromethyl)-5-phenylmethoxy-1,2-dihydrobenzo[e]indole-3-carboxylate
• CAS: 261763-56-8
• 化学式: C₂₇H₂₉ClN₂O₄
• 分子量: 480.991
• InChiKey: ZZYAFFDBHOBGIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-chloromethyl-7-acetylamino-1,2-dihydro-3H-benz[e]indole 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 生成 N-(5-Benzyloxy-1-chloromethyl-2,3-dihydro-1H-benzo[e]indol-7-yl)-acetamide
  参考文献：
  名称：

  Synthesis and cytotoxicity evaluation of novel C7–C7, C7–N3 and N3–N3 dimers of 1-chloromethyl-5-hydroxy-1,2-dihydro-3H-benzo[e]indole (seco-CBI) with pyrrole and imidazole polyamide conjugates

  摘要：

  合成了1-氯甲基-5-羟基-1,2-二氢-3H-苯并[e]吲哚（seco-CBI）与吡咯和咪唑聚酰胺的C7–C7、C7–N3和N3–N3二聚体，并通过NCI对三种类型的癌细胞进行了初步抗癌评估。

  DOI：

  10.1039/b303650m
• 作为产物：
  描述：

  N-(tert-butyloxycarbonyl)-N-(3-chloro-2-propen-1-yl)-4-benzyloxy-1-iodo-6-nitro-2-naphthylamine 在 三氯化铁 、 一水合肼 作用下， 生成 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-chloromethyl-7-acetylamino-1,2-dihydro-3H-benz[e]indole
  参考文献：
  名称：

  Jia, Guofeng; Iida, Hirokazu; Lown, J. William, Synlett, 2000, # 5, p. 603 - 606

  摘要：

  DOI：

文献信息

• Design and Synthesis of Bis 1-Chloromethyl-5-hydroxy-1,2- dihydro-3<i>H</i>-benz[<i>e</i>]indole (<i>s</i><i>eco</i>-CBI)-Pyrrole Polyamide Conjugates
  作者：Rohtash Kumar、J. William Lown

  DOI：10.1021/ol020047k

  日期：2002.5.1

  [GRAPHICS]The design and synthesis of bis 1-chloromethyl-5-hydroxy-1,2-dihydro-3H-benz[e]indole (seco-CBI)-pyrrole polyamide conjugates (13, 17) as DNA minor groove binding agents are described.
• Design, synthesis and cytotoxicity evaluation of 1-chloromethyl-5-hydroxy-1,2-dihydro-3 H -benz[ e ]indole ( seco -CBI) dimers
  作者：Guofeng Jia、J.William Lown

  DOI：10.1016/s0968-0896(00)00088-2

  日期：2000.7

  Three types of 1-chloromethyl-5-hydroxy-1,2-dihydro-3H-benz[e]indole (seco-CBI) dimers were designed, synthesized and evaluated in vitro by NCI against nine types of cancer cells. Biological results showed that the antitumor activities of these seco-CBI dimers were strongly related to the position and length of the linker and generally with potency increasing in the order of C7-C7 dimers (22i-iv) < C7-N3 dimers (28i-iv) < N3-N3 dimers (25i-iv). Compound 28iv showed significant activity against CCRT-CEM, HL-60 (TB), MOLT-4, and SR leukemia cell lines and the MCF 7 breast cancer cell line with GI(50) values < 0.01 mu M. N3-N3 dimer 25i displayed striking potency against leukemia, CNS cancer, melanoma and prostate cancer cell lines with GI(50) values < 0.01 mu M against all the cell lines and showed the highest overall potency of the agents examined (GMG = 0.0120 mu M). (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis and cytotoxicity evaluation of novel C7–C7, C7–N3 and N3–N3 dimers of 1-chloromethyl-5-hydroxy-1,2-dihydro-3H-benzo[e]indole (seco-CBI) with pyrrole and imidazole polyamide conjugates
  作者：Rohtash Kumar、J. William Lown

  DOI：10.1039/b303650m

  日期：——

  The C7–C7, C7–N3 and N3–N3 dimers of 1-chloromethyl-5-hydroxy-1,2-dihydro-3H-benzo[e]indole (seco-CBI) with pyrrole and imidazole polyamides were synthesized and preliminary anti-cancer evaluation carried out by NCI against three types of cancer cells.

  合成了1-氯甲基-5-羟基-1,2-二氢-3H-苯并[e]吲哚（seco-CBI）与吡咯和咪唑聚酰胺的C7–C7、C7–N3和N3–N3二聚体，并通过NCI对三种类型的癌细胞进行了初步抗癌评估。
• Jia, Guofeng; Iida, Hirokazu; Lown, J. William, Synlett, 2000, # 5, p. 603 - 606
  作者：Jia, Guofeng、Iida, Hirokazu、Lown, J. William

  DOI：——

  日期：——