4-toluenesulfinylureido-hystamine

• 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: 4-toluenesulfinylureido-hystamine
• 英文别名: 1-[2-(1H-imidazol-5-yl)ethyl]-3-(4-methylphenyl)sulfonylurea
• 化学式: C₁₃H₁₆N₄O₃S
• 分子量: 308.361
• InChiKey: FQSKBIRASYBLEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  组胺 在 盐酸 、 三乙胺 、 肼 作用下， 以 1,4-二氧六环 、 乙醇 、 甲苯 、 乙腈 为溶剂， 反应 11.0h， 生成 4-toluenesulfinylureido-hystamine
  参考文献：
  名称：

  Novel carbonic anhydrase isozymes I, II and IV activators incorporating sulfonyl-histamino moieties

  摘要：

  Sulfonylamido(ureido) derivatives of histamine were synthesized by an original procedure in order to obtain tight-binding activators of the zinc enzyme carbonic anhydrase (CA), exploiting the binding energy of the alkyl/arylsulfonyl moieties with amino acid residues at the entrance of the active site. In contrast to the lead molecule, histamine, the new derivatives possessed higher affinity for three different CA isozymes, as evidenced by compairing the affinity constants of these compounds for isozyme CA II. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00310-8

文献信息

• 4-Toluenesulfonylureido derivatives of amines, amino acids and dipeptides: a novel class of potential antitumor agents
  作者：Antonio Mastrolorenzo、Andrea Scozzafava、Claudiu T. Supuran

  DOI：10.1016/s0928-0987(00)00122-6

  日期：2000.10

  The screening of a series of arylsulfonylureido derivatives of amines (such as histamine, or dopamine), aliphatic/aromatic amino acids (such as Gly, beta -Ala, Val, Lys, Arg, Phe, Tyr, DOPA, etc.) and dipeptides (such as GlyGly, beta -AlaHis) led to the identification of three derivatives that possess tumor growth inhibitory properties against several leukemia, non-small cell lung, ovarian, melanoma, colon, CNS, renal, and breast cancer cell lines in vitro. The new derivatives were prepared by reaction of 4-toluenesulfonyl isocyanate with (protected) amines, amino acids or dipeptides. The mechanism of antitumor action with these new derivatives is not known at the moment but it may imply uncoupling of mitochondria, as for the structurally related diarylsulfonylurea sulofenur, an investigational anticancer agent. (C) 2000 Elsevier Science B.V. All rights reserved.
• COMPOSITIONS AND METHODS FOR TREATING FRIEDREICH'S ATAXIA
  申请人：Testi Roberto

  公开号：US20130109658A1

  公开（公告）日：2013-05-02

  A method of treating Friedreich's Ataxia with compounds of formula I including pharmaceutically acceptable salts, tautomers or stereoisomers of compounds of formula Lp.
• US8703749B2
  申请人：——

  公开号：US8703749B2

  公开（公告）日：2014-04-22
• [EN] COMPOSITIONS AND METHODS FOR TREATING FRIEDREICH'S ATAXIA<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR TRAITER L'ATAXIE DE FRIEDREICH
  申请人：TESTI ROBERTO

  公开号：WO2011070444A2

  公开（公告）日：2011-06-16

  A method of treating Friedreich's Ataxia with compounds of formula I including pharmaceutically acceptable salts, tautomers or stereoisomers of compounds of formula Lp.
• Novel carbonic anhydrase isozymes I, II and IV activators incorporating sulfonyl-histamino moieties
  作者：Fabrizio Briganti、Andrea Scozzafava、Claudiu T. Supuran

  DOI：10.1016/s0960-894x(99)00310-8

  日期：1999.7

  Sulfonylamido(ureido) derivatives of histamine were synthesized by an original procedure in order to obtain tight-binding activators of the zinc enzyme carbonic anhydrase (CA), exploiting the binding energy of the alkyl/arylsulfonyl moieties with amino acid residues at the entrance of the active site. In contrast to the lead molecule, histamine, the new derivatives possessed higher affinity for three different CA isozymes, as evidenced by compairing the affinity constants of these compounds for isozyme CA II. (C) 1999 Elsevier Science Ltd. All rights reserved.