3-acetoxymethyl-5-amino-6-benzyloxy-1-t-butoxycarbonyl-2,3-dihydro-1H-indole | 132628-60-5

• 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: 3-acetoxymethyl-5-amino-6-benzyloxy-1-t-butoxycarbonyl-2,3-dihydro-1H-indole
• 英文别名: 3-Acetoxymethyl-5-amino-6-benzyloxy-1-t-butoxycarbonylindoline；tert-butyl 3-(acetyloxymethyl)-5-amino-6-phenylmethoxy-2,3-dihydroindole-1-carboxylate
• CAS: 132628-60-5
• 化学式: C₂₃H₂₈N₂O₅
• 分子量: 412.486
• InChiKey: VGDDLJTVOVKQQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  91.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-acetoxymethyl-5-amino-6-benzyloxy-1-t-butoxycarbonyl-2,3-dihydro-1H-indole 在 咪唑 、 碳酸氢钠 、 potassium carbonate 、 间氯过氧苯甲酸 、 copper(II) oxide 、 copper dichloride 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 15.0h， 生成 methyl 5-amino-6-benzyloxy-1-t-butoxycarbonyl-3-(t-butyldimethylsilyloxy)methyl-2,3-dihydro-1H-indole-4-carboxylate
  参考文献：
  名称：

  First total synthesis of dl-duocarmycin A

  摘要：

  DOI：

  10.1016/s0040-4039(00)97151-x
• 作为产物：
  描述：

  3-acetoxymethyl-6-benzyloxy-1-t-butoxycarbonyl-2,3-dihydro-5-nitro-1H-indole 在 platinum(IV) oxide 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以95%的产率得到3-acetoxymethyl-5-amino-6-benzyloxy-1-t-butoxycarbonyl-2,3-dihydro-1H-indole
  参考文献：
  名称：

  Synthetic studies on duocarmycin. 1. Total synthesis of dl-duocarmycin A and its 2-epimer

  摘要：

  The title synthesis was first achieved by employing novel methoxycarbonylation of the C-4-position of the 5-aminoindoline by way of the isatin and subsequent Dieckmann cyclization to the methyl 2-methylindoxyl-2- carboxylate as key steps. In vitro cytotoxicity assay against P388 murine leukemia obviously disclosed that cytotoxicities of the synthesized compounds are comparable and almost half of that of natural (+)-duocarmycin A.

  DOI：

  10.1016/s0040-4020(01)86993-3

文献信息

• Intermediates for the preparation of duocarmycin SA and derivatives
  申请人：Kyorin Pharmaceutical Co., Ltd.

  公开号：US06066742A1

  公开（公告）日：2000-05-23

  Indole derivatives shown by the formulae (1), (2a) and (2b) ##STR1## (wherein R.sup.1 is a protecting group for amino group; R.sup.2 is a protecting group for hydroxyl group; R.sup.3 is a protecting group for hydroxyl group; R.sup.4 is a C.sub.1 -C.sub.6 linear or branched lower alkyl group, or benzyl group), and pyrroloindole derivatives shown by formula (3) ##STR2## (wherein R.sup.1 is a protecting group for amino group; R.sup.2 is a protecting group for hydroxyl group; R.sup.3 is a protecting group for hydroxyl group; R.sup.4 is a C.sub.1 -C.sub.6 linear or branched lower alkyl group, or benzyl group), both of which are intermediates for duocarmycin SA, which is expected to be used as an anticancer agent, and derivatives thereof; and a method for producing the same.

  公式(1)、(2a)和(2b)所示的吲哚衍生物##STR1## (其中R.sup.1是氨基保护基；R.sup.2是羟基保护基；R.sup.3是羟基保护基；R.sup.4是C.sub.1-C.sub.6线性或支链低烷基或苄基)，以及公式(3)所示的吡咯吲哚衍生物##STR2## (其中R.sup.1是氨基保护基；R.sup.2是羟基保护基；R.sup.3是羟基保护基；R.sup.4是C.sub.1-C.sub.6线性或支链低烷基或苄基)，两者均为duocarmycin SA的中间体，预计用作抗癌剂及其衍生物；以及制备它们的方法。
• TRIFLUOROMETHYLPYRROLOINDOLE CARBOXYLIC ESTER DERIVATIVE AND PROCESS FOR PRODUCING THE SAME
  申请人：KYORIN PHARMACEUTICAL CO., LTD.

  公开号：EP0656360A1

  公开（公告）日：1995-06-07

  Trifluoromethylpyrroloindole carboxylic ester derivatives represented by general formulae (1) and (2) having an antitumor activity, optically active isomers thereof, and pharmacologically acceptable salts thereof, wherein R represents lower alkyl; R¹ represents an α-amino acid residue, etc.; R² represents hydrogen, a hydroxyl-protecting group, etc.; and Y represents halogen, arylsulfonyloxy, etc.

  通式(1)和(2)代表的具有抗肿瘤活性的三氟甲基吡咯吲哚羧酸酯衍生物、其光学活性异构体及其药理上可接受的盐，其中R代表低级烷基；R¹代表α-氨基酸残基等；R²代表氢、羟基保护基等；Y代表卤素、芳基磺酰氧基等。
• Synthesis and Cytotoxicity of Various Structural Types of Novel Cyclopropapyrroloindole(CPI) Derivatives
  作者：Yasumichi Fukuda、Hirosuke Furuta、Yoshie Kusama、Hiroyuki Ebisu、Yasuo Oomori、Shiro Terashima

  DOI：10.3987/com-98-s21

  日期：——

  The various structural types of novel cyclopropapyrroloindole(CPI) derivatives (7 similar to 10) were synthesized and their cytotoxicity was evaluated. Among these derivatives, 3-methoxycarbonylCPI(3-MCCPI) derivatives (8a,b) and cyclopropapyrrolocarbazole (CPC) derivative (10a) were found to exhibit comparable cytotoxicity to U-73,975 (adozelesin) (1).
• First total synthesis of dl-duocarmycin A
  作者：Yasumichi Fukuda、Kazuhiko Nakatani、Yoshio Ito、Shiro Terashima

  DOI：10.1016/s0040-4039(00)97151-x

  日期：1990.1
• Synthesis and antitumor activity of novel cyclopropapyrroloindole(CPI) derivatives bearing methoxycarbonyl and trifluoromethyl groups
  作者：Yasumichi Fukuda、Hirosuke Furuta、Futoshi Shiga、Yasuo Oomori、Yoshie Kusama、Hiroyuki Ebisu、Shiro Terashima

  DOI：10.1016/s0960-894x(97)00288-6

  日期：1997.7

  The title synthesis was achieved by employing oxidative cyclization of the enaminoester as a key step. Some of these novel 3-methoxycarbonyl-2-trifluoromethylcyclopropapyrroloindole (MCTFCPI) derivatives, dl-10c,d, (+)-10d, and (S)-21b were found to exhibit antitumor activity against murine leukemia and murine solid tumors more prominent than that of the known CPI derivatives dl-4 and the clinical trial candidates 5 and 7. (C) 1997 Elsevier Science Ltd.