4-(3-phenylthioureido)benzenesulfonamide | 4474-05-9

• 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-(3-phenylthioureido)benzenesulfonamide
• 英文别名: 1-phenyl-3-(4-sulfamoylphenyl)thiourea；4-(3-phenyl-thioureido)-benzenesulfonamide；N-phenyl-N'-(4-sulfamoyl-phenyl)-thiourea；N-Phenyl-N'-(4-sulfamoyl-phenyl)-thioharnstoff；N-Phenylthiocarbamoyl-sulfanilsaeure-amid
• CAS: 4474-05-9
• 化学式: C₁₃H₁₃N₃O₂S₂
• 分子量: 307.397
• InChiKey: OOWRWZBEYIUVQH-UHFFFAOYSA-N

物化性质

• 熔点：
  190-191 °C
• 沸点：
  496.1±55.0 °C(Predicted)
• 密度：
  1.487±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(3-phenylthioureido)benzenesulfonamide 以 四氢呋喃 、 乙酰氯 为溶剂， 反应 12.0h， 生成 4-[4,6-Dioxo-3-phenyl-2-sulfanylidene-5-(2,2,2-trifluoroacetyl)-1,3-diazinan-1-yl]benzenesulfonamide
  参考文献：
  名称：

  苯磺酰胺类抗糖尿病和抗菌药的新巴比妥和硫代巴比妥酸氟类似物的合成及生物学评价

  摘要：

  一种新颖的一系列巴比妥和硫代巴比妥酸（苯磺酰胺衍生物的2 - 12）是由不同的脲基的缩合和环化反应和磺胺的硫脲衍生物为原料合成。不同的取代基已在C-5和巴比妥硫代巴比妥酸的被纳入。氟和三氟乙酰基取代基已安装在各个位置，并使用相应的非氟化类似物进行了比较生物筛选。评价合成的化合物的抗微生物和抗糖尿病活性。一些具有氟取代的目标化合物显示出非常好的抗菌和抗糖尿病活性。

  DOI：

  10.1016/j.jfluchem.2012.06.032
• 作为产物：
  描述：

  硫代异氰酸苯酯 、 磺胺 生成 4-(3-phenylthioureido)benzenesulfonamide
  参考文献：
  名称：

  新合成的异硫氰酸酯衍生物对病原植物微生物的抗菌活性

  摘要：

  合成了异硫氰酸酯与半胱氨酸的十五种反应产物，异硫氰酸酯与2,3-二巯基-1-丙醇的七种反应产物以及异硫氰酸酯与磺酰胺的四种反应产物。研究了它们对病原植物微生物的抗菌活性。

  DOI：

  10.1002/jps.2600651039

文献信息

• INHIBITORS OF CARBONIC ANHYDRASE IX
  申请人：Zimmerman Craig

  公开号：US20090175794A1

  公开（公告）日：2009-07-09

  Novel radiopharmaceuticals that are useful in diagnostic imaging and therapeutic treatment of disease characterized by over expression of CA-IX comprise a complex that contains a sulfonamide moiety which is capable of binding the active catalytic site of CA-IX, and a radionuclide adapted for radioimaging and/or radiotherapy:

  具有在诊断成像和治疗过度表达CA-IX疾病中有用的新型放射性药物，包括一种含有磺胺基团的复合物，该基团能够结合CA-IX的活性催化位点，以及适用于放射成像和/或放射治疗的放射性核素：
• Tuning the Dual Inhibition of Carbonic Anhydrase and Cyclooxygenase by Dihydrothiazole Benzensulfonamides
  作者：Rita Meleddu、Simona Distinto、Filippo Cottiglia、Rossella Angius、Marco Gaspari、Domenico Taverna、Claudia Melis、Andrea Angeli、Giulia Bianco、Serenella Deplano、Benedetta Fois、Sonia Del Prete、Clemente Capasso、Stefano Alcaro、Francesco Ortuso、Matilde Yanez、Claudiu T. Supuran、Elias Maccioni

  DOI：10.1021/acsmedchemlett.8b00352

  日期：2018.10.11

  hCOX-2 isozyme, indicating that 2,3,4-trisubstituted 2,3-dihydrothiazoles are a promising scaffold for the inhibition of hCA isozymes and of hCOX-2 enzyme. The nature of the substituent at the dihydrothiazole ring position 4 influenced the activity and selectivity toward both enzyme families. EMAC10111g resulted as the best performing compound toward both enzyme families and exhibited preferential activity

  合成了一系列新颖的4-[（3-苯基-4-芳基-2,3-二氢-1,3-噻唑-2-亚甲基）氨基]苯-1-磺酰胺（EMAC10111a–g），并对其进行了测定人碳酸酐酶同工酶I，II，IX和XII以及环氧合酶同工型。这些衍生物中的大多数优先抑制hCA同工型II和XII和hCOX-2同工酶，表明2,3,4-三取代的2,3-二氢噻唑是抑制hCA同工酶和hCOX-2酶的有前途的支架。在二氢噻唑环位置4的取代基的性质影响了对两个酶家族的活性和选择性。EMAC10111g是针对这两个酶家族表现最佳的化合物，并且对hCA XII和hCOX-2同工酶表现出优先活性。
• The Preparation of Sulfanilamide Derivatives Containing a Urea or Thiourea Grouping
  作者：Jay S. Roth、Ed. F. Degering

  DOI：10.1021/ja01217a042

  日期：1945.1
• 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.
• Abdel-Monem, Wafaa R, Bollettino Chimico Farmaceutico, 2004, vol. 143, # 6, p. 239 - 247
  作者：Abdel-Monem, Wafaa R

  DOI：——

  日期：——