6-amino-3-(chloromethyl)-1-[(5',6',7'-trimethoxyindol-2'-yl)carbonyl]-indoline | 185424-55-9

• 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: 6-amino-3-(chloromethyl)-1-[(5',6',7'-trimethoxyindol-2'-yl)carbonyl]-indoline
• 英文别名: 6-amino-3-(chloromethyl)-1-[(5',6',7'-trimethoxyindol-2'-yl)carbonyl]indoline；1-[(5,6,7-Trimethoxy-1H-indol-2-yl)carbonyl]-3-(chloromethyl)indolin-6-amine；[6-amino-3-(chloromethyl)-2,3-dihydroindol-1-yl]-(5,6,7-trimethoxy-1H-indol-2-yl)methanone
• CAS: 185424-55-9
• 化学式: C₂₁H₂₂ClN₃O₄
• 分子量: 415.876
• InChiKey: FDRIUJFXAJREQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  89.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-amino-3-(chloromethyl)-1-[(5',6',7'-trimethoxyindol-2'-yl)carbonyl]-indoline 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 1.08h， 生成 [3-(chloromethyl)-6-(methylamino)-2,3-dihydroindol-1-yl]-(5,6,7-trimethoxy-1H-indol-2-yl)methanone
  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：

  (+/-)-1-(tert-butyloxycarbonyl)-3-[[(methylsulfonyl)oxy]methyl]-6-nitroindoline 在 platinum(IV) oxide 盐酸 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基乙酰胺 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 80.0 ℃ 、344.73 kPa 条件下， 反应 14.67h， 生成 6-amino-3-(chloromethyl)-1-[(5',6',7'-trimethoxyindol-2'-yl)carbonyl]-indoline
  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

• Radiation-activated cytotoxin therapy of neoplastic disease
  申请人：Auckland Uniservices Limited

  公开号：US06071908A1

  公开（公告）日：2000-06-06

  A method of treating neoplastic disease wherein a patient in need of such treatment is administered an effective amount of a radiation-activated cytotoxin prodrug (RACP) which has low toxicity, which is reducible by reducing agents generated by the radiolysis of water and which, upon reduction, releases a sufficient amount of a cytotoxic effector of sufficient cytotoxic potency to kill tumor cells. The tumor cells are irradiated with ionizing radiation to reduce the prodrug which is present at the locus of the tumor cells to release the cytotoxic effector.

  一种治疗肿瘤性疾病的方法，其中需要接受治疗的患者被给予低毒性的放射活化细胞毒素前药(RACP)的有效剂量，该前药可以通过水的辐解生成的还原剂还原，它的毒性较低，还原后释放足够的细胞毒素，具有足够的细胞毒性杀死肿瘤细胞。肿瘤细胞被电离辐射以还原存在于肿瘤细胞处的前药，释放细胞毒素。
• Radiation-activated cytotoxin therapy
  申请人：AUCKLAND UNISERVICES LIMITED

  公开号：EP1225169A1

  公开（公告）日：2002-07-24

  A method of treating neoplastic disease which comprises the steps of: (a) administering to a patient in need of such treatment an effective amount of a radiation-activated cytotoxin prodrug (RACP) which has low toxicity, which can be reduced by reducing agents generated by the radiolysis of water (the equated electron and/or the hydrogen radical) and which, upon reduction, releases a sufficient amount of an effector of sufficient cytotoxic potency to kill tumour cells; and (b) irradiating said tumour cells to reduce the prodrug which is present at the locus of said tumour cells to release said cytotoxic effector. In preferred embodiments, the RACP is of formula (I), (VI), (VII) or (VIII).

  一种治疗肿瘤性疾病的方法，包括以下步骤 (a) 给需要这种治疗的病人服用有效量的辐射活化细胞毒素原药(RACP)，该原药毒性低，可被水的辐射分解产生的还原剂(等价电子和/或氢自由基)还原，还原后释放出足够量的具有足够细胞毒性效力的效应物，以杀死肿瘤细胞；以及 (b) 对所述肿瘤细胞进行辐照，以还原存在于所述肿瘤细胞部位的原药，从而释放所述细胞毒性效应物。 在优选的实施方案中，RACP 是式 (I)、(VI)、(VII) 或 (VIII)。
• 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
• Nitrogen and sulfur analogues of the secoCI alkylating agent: Synthesis and cytotoxicity
  作者：M. Tercel、W.A. Denny、W.R. Wilson

  DOI：10.1016/s0960-894x(96)00507-0

  日期：1996.11

  The first synthesis of seca-CI alkylating agents bearing a nitrogen or sulfur substituent in place of the oxygen at C-6 is described. In comparison with a phenol, an amino substituent confers reduced but significant cytotoxicity, even when mono- or dimethylated, while sulfur analogues are considerably less potent. Copyright (C) 1996 Elsevier Science Ltd
• 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