ammonium 4-(benzothiazol-2-yl)phenylsulphamate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ammonium 4-(benzothiazol-2-yl)phenylsulphamate
• 英文别名: azanium;N-[4-(1,3-benzothiazol-2-yl)phenyl]sulfamate
• 化学式: C₁₃H₉N₂O₃S₂*H₄N
• 分子量: 323.397
• InChiKey: OBXJRQRBVWSTPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-(2-苯并噻唑基)苯胺 在 碳酸甲丙酯 、 氯磺酸 、 ammonium hydroxide 作用下， 反应 1.0h， 以69%的产率得到ammonium 4-(benzothiazol-2-yl)phenylsulphamate
  参考文献：
  名称：

  Antitumour Benzothiazoles. Part 15: The Synthesis and Physico-Chemical Properties of 2-(4-Aminophenyl)benzothiazole Sulfamate Salt Derivatives

  摘要：

  A series of sulfamate salt derivatives of the potent and selective 2-(4-aminophenyl)benzothiazole: antitumour agents has been prepared and their evaluation as potential prodrugs for parenteral administration carried out. The salts were sparingly soluble under aqueous conditions (pH 4-9), and degradation to the active free amine was shown to occur under strongly acidic conditions. The salts were found to be markedly less active than their parent amines against sensitive human tumour cell lines in vitro. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00142-1

文献信息

• 2-arylbenzazole compounds
  申请人：Cancer Research Campaign Technology Limited

  公开号：US06034246A1

  公开（公告）日：2000-03-07

  There are disclosed herein 2-phenylbenzazole compounds having a 3'-substituent and a 4'-NR.sup.2 R.sup.6 substituent in the phenyl group where R.sup.5 and R.sup.6 are each hydrogen or alkyl, or where the $'-NR.sup.5 R.sup.6 substituent is N-acyl (or N-benzoyl). There are also disclosed 2-phenylbenzazole compounds in the form of 4'-N sulphamate salts. Such compounds exhibit significant selective cytotoxic activity in respect of tumor cells and provide potentially useful chemotherapeutic agents for selective treatment of a range of cancers.

  本文披露了含有3'-取代基和4'-NR.sup.2 R.sup.6取代基的2-苯基苯并咪唑化合物，其中苯基中的R.sup.5和R.sup.6分别为氢或烷基，或者4'-NR.sup.5 R.sup.6取代基为N-酰基（或N-苯甲酰基）。还披露了以4'-N磺酸盐形式存在的2-苯基苯并咪唑化合物。这些化合物在肿瘤细胞中表现出显著的选择性细胞毒活性，并为选择性治疗多种癌症提供了潜在有用的化疗药物。
• 2-ARYLBENZAZOLE COMPOUNDS
  申请人：Cancer Research Ventures Limited

  公开号：EP0812319B1

  公开（公告）日：2002-07-10
• US6034246A
  申请人：——

  公开号：US6034246A

  公开（公告）日：2000-03-07
• [EN] 2-ARYLBENZAZOLE COMPOUNDS<br/>[FR] COMPOSES 2-ARYLBENZAZOLE
  申请人：CANCER RESEARCH CAMPAIGN TECHNOLOGY LIMITED

  公开号：WO1996026932A1

  公开（公告）日：1996-09-06

  (EN) There are disclosed herein 2-phenylbenzazole compounds having a 3'-substituent and a 4'-NR5R6 substituent in the phenyl group where R5 and R6 are each hydrogen or alkyl, or where the 4'-NR5R6 substituent is N-acyl (or N-benzoyl). There are also disclosed 2-phenylbenzazole compounds in the form of 4'-N sulphamate salts. Such compounds exhibit significant selective cytotoxic activity in respect of tumor cells and provide potentially useful chemotherapeutic agents for selective treatment of a range of cancers.(FR) Cette invention concerne des composés 2-phénylbenzazole ayant un substituant en 3' et un substituant NR5R6 en 4' dans le groupe phényle, R5 et R6 étant chacun l'hydrogène ou un alkyle, ou le substituant NR5R6 en 4' étant un N-acyle (ou un N-benzoyle). L'invention se rapporte également à des composés 2-phényl-benzazole sous la forme de sels de sulphamate portant N en 4'. De tels composés présentent une activité cytotoxique sélective significative vis-à-vis des cellules tumorales et permettent de disposer d'agents chimiothérapeutiques potentiellement utiles pour le traitement sélectif d'un certain nombre de cancers.
• Antitumour Benzothiazoles. Part 15: The Synthesis and Physico-Chemical Properties of 2-(4-Aminophenyl)benzothiazole Sulfamate Salt Derivatives
  作者：Dong-Fang Shi、Tracey D Bradshaw、Mei-Sze Chua、Andrew D Westwell、Malcolm F.G Stevens

  DOI：10.1016/s0960-894x(01)00142-1

  日期：2001.4

  A series of sulfamate salt derivatives of the potent and selective 2-(4-aminophenyl)benzothiazole: antitumour agents has been prepared and their evaluation as potential prodrugs for parenteral administration carried out. The salts were sparingly soluble under aqueous conditions (pH 4-9), and degradation to the active free amine was shown to occur under strongly acidic conditions. The salts were found to be markedly less active than their parent amines against sensitive human tumour cell lines in vitro. (C) 2001 Elsevier Science Ltd. All rights reserved.