3-thioureidobenzenesulfonamide | 5657-42-1

• 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: 3-thioureidobenzenesulfonamide
• 英文别名: (3-sulfamoyl-phenyl)-thiourea；(3-Sulfamoyl-phenyl)-thioharnstoff；3-[(aminocarbonothioyl)amino]benzenesulfonamide；3-Thioureido-benzenesulfonamide；(3-sulfamoylphenyl)thiourea
• CAS: 5657-42-1
• 化学式: C₇H₉N₃O₂S₂
• 分子量: 231.299
• InChiKey: RHQOJJGJLHNWMI-UHFFFAOYSA-N

物化性质

• 沸点：
  459.9±55.0 °C(Predicted)
• 密度：
  1.578±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  139
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-thioureidobenzenesulfonamide 在 溴 作用下， 以 氯仿 为溶剂， 反应 24.0h， 生成 2-amino-4-bromobenzo[d]thiazole-5-sulfonamide
  参考文献：
  名称：

  一系列苯并[d]噻唑-5-和6-磺酰胺的合成和碳酸酐酶I，II，VII和IX抑制研究。

  摘要：

  合成了一系列苯并[d]噻唑-5-和6-磺酰胺，并使用乙恶唑酰胺（EZA）作为先导分子，研究了对几种人（h）碳酸酐酶（CA，EC 4.2.1.1）同工型的抑制作用。2-氨基取代的，2-酰基氨基和卤代的（杂环上的溴和碘衍生物）化合物产生了几种有趣的针对胞质hCA I，II和VII以及跨膜的，与肿瘤相关的hCA的抑制剂IX同工型。检测到了几种靶向hCA II，VII和IX的亚纳摩尔/低纳摩尔异构体选择性磺酰胺抑制剂。用这种小系列衍生物抑制CA的结构与活性之间存在着尖锐的结构-活性关系，即使在支架或2-氨基部分发生微小变化后，活性也发生了重要变化，

  DOI：

  10.1080/14756366.2017.1356295
• 作为产物：
  描述：

  3-aminobenzenesulfonamide hydrochloride 、 苯甲酰基异硫氰酸酯 在 N,N-二异丙基乙胺 、 水 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 60.0h， 以76%的产率得到3-thioureidobenzenesulfonamide
  参考文献：
  名称：

  [EN] THIAZOLE DERIVATIVES
  [FR] DERIVES DE THIAZOLE

  摘要：

  公式（I）的化合物以及其药学上可接受的盐和酯，其中R1至R4具有权利要求1中给出的意义，可用于制备药物组合物。

  公开号：

  WO2004014884A1

文献信息

• Aminothiazole derivatives
  申请人：——

  公开号：US20040038990A1

  公开（公告）日：2004-02-26

  Compounds of formula I 1 as well as pharmaceutically acceptable salts and esters thereof, wherein R 1 to R 4 have the significance given in the specification, and the compounds, salts and esters can be used for the treatment of obesity.

  化合物I1的公式及其药学上可接受的盐和酯，其中R1至R4具有规范中所给定的意义，这些化合物、盐和酯可用于治疗肥胖症。
• Thiazole Derivatives and Use Thereof
  申请人：Quattropani Anna

  公开号：US20090029998A1

  公开（公告）日：2009-01-29

  The present invention is related to thiazole derivatives of Formula (I) in particular for the treatment and/or prophylaxis of autoimmune disorders and/or inflammatory diseases, cardiovascular diseases, neurodegenerative diseases, bacterial or viral infections, kidney diseases, platelet aggregation, cancer, transplantation, graft rejection or lung injuries.

  本发明涉及公式（I）的噻唑衍生物，特别是用于治疗和/或预防自身免疫性疾病和/或炎症性疾病，心血管疾病，神经退行性疾病，细菌或病毒感染，肾脏疾病，血小板聚集，癌症，移植，移植排斥或肺损伤。
• THIAZOLE DERIVATIVES AND USE THEREOF
  申请人：QUATTROPANI Anna

  公开号：US20140228365A1

  公开（公告）日：2014-08-14

  The present invention is related to thiazole derivatives of Formula (I) in particular for the treatment and/or prophylaxis of autoimmune disorders and/or inflammatory diseases, cardiovascular diseases, neturodegenerative diseases, bacterial or viral infections, kidney diseases, platelet aggregation, cancer, transplantation, graft rejection or lung injuries.

  本发明涉及式(I)的噻唑衍生物，特别是用于治疗和/或预防自身免疫性疾病和/或炎症性疾病、心血管疾病、神经退行性疾病、细菌或病毒感染、肾脏疾病、血小板聚集、癌症、移植、移植排斥或肺损伤。
• A library of novel allosteric inhibitors against fructose 1,6-bisphosphatase
  作者：Sabrina Heng、Kimberly R. Gryncel、Evan R. Kantrowitz

  DOI：10.1016/j.bmc.2009.04.030

  日期：2009.6

  The identification of a proper lead compound for fructose 1,6-bisphosphatase (FBPase) is a critical step in the process of developing novel therapeutics against type-2 diabetes. Herein, we have successfully generated a library of allosteric inhibitors against FBPase as potential anti-diabetic drugs, of which, the lead compound 1b was identified through utilizing a virtual high-throughput screening (vHTS) system, which we have developed. The thiazole-based core structure was synthesized via the condensation of alpha-bromoketones with thioureas and substituents on the two aryl rings were varied. 4c was found to inhibit pig kidney FBPase approximately fivefold better than 1b. In addition, we have also identified 10b, a tight binding fragment, which can be use for fragment-based drug design purposes. (C) 2009 Elsevier Ltd. All rights reserved.
• Carbonic anhydrase inhibitors - Part 49: Synthesis of substituted ureido and thioureido derivatives of aromatic/heterocyclic sulfonamides with increased affinities for isozyme I
  作者：Claudiu T. Supuran、Andrea Scozzafava、Bogdan C. Jurca、Marc A. Ilies

  DOI：10.1016/s0223-5234(98)80033-0

  日期：1998.2

  Reaction of nine aromatic/heterocyclic sulfonamides containing a free amino group with aryl isocyanates/isothiocyanates or allyl isothiocyanate afforded the corresponding urea/thiourea derivatives, which were characterized by standard physico-chemical procedures and assayed as inhibitors of three isozymes of carbonic anhydrase (CA), i.e. hCA I, hCA II and bCA IV (h = human, b = bovine isozyme). Another series of compounds, 1,5-disubstituted-2-thiobiuret derivatives, were prepared by reaction of 3,4-dichlorophenyl isocyanate with thioureido-containing aromatic/heterocyclic sulfonamides. Good inhibition of all these three CA isozymes was observed with the new compounds, but an exciting finding was that the ureas/thioureas and especially the above-mentioned thiobiurets reported here have an increased affinity to the slow isozyme hCA I, generally less susceptible to inhibition by sulfonamides, as compared to the rapid isozymes hCA II and bCA IV. Some of the new compounds might constitute good lead molecules for developing more selective CA I inhibitors. (C) Elsevier, Paris.