1-(2-carboxyethyl) 3-p-chlorophenylthiouree | 3744-12-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-(2-carboxyethyl) 3-p-chlorophenylthiouree
• 英文别名: N-[(4-chloro-phenyl)-thiocarbamoyl]-β-alanine；N-<4-Chlor-phenyl>-N'-<2-hydroxycarbonyl-aethyl>-thioharnstoff；N-<4-Chlor-phenyl>-N'-<2-hydroxycarbonyl-ethyl>-thioharnstoff；3-[(4-Chlorophenyl)carbamothioylamino]propanoic acid
• CAS: 3744-12-5
• 化学式: C₁₀H₁₁ClN₂O₂S
• 分子量: 258.729
• InChiKey: RIIKGQQQCKYJBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  93.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-carboxyethyl) 3-p-chlorophenylthiouree 在 potassium carbonate 、 N,N'-羰基二咪唑 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 1.67h， 生成 3-(4-chlorophenyl)-2-(2-oxo-2-phenylethylthio)-5,6-dihydropyrimidin-4(3H)-one
  参考文献：
  名称：

  A Facile Synthesis and Chemoselective Reactions of Dihydrothiouracils

  摘要：

  A highly efficient procedure was devised for the synthesis of 3-(3-arylthioureido)propanoic/butanoic acid and its cyclization to (3-aryl/3-aryl-6-methyl)-2-thioxotetrahydropyrimidin-4(1H)-one derivatives. Carbonyl diimidazole proved to be a very effective coupling reagent for the cyclization. Studies carried out to examine the ambident nature of the thioamide moiety towards substitution reactions demonstrated the preference for alkylation at sulfur, and acylation and 1,4-addition at nitrogen.

  DOI：

  10.1055/s-0032-1317133
• 作为产物：
  描述：

  4-氯异硫氰酸苯酯 、 β-丙氨酸 在 sodium carbonate 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以70%的产率得到1-(2-carboxyethyl) 3-p-chlorophenylthiouree
  参考文献：
  名称：

  Synthèse, activité antiparasitaire et antifongique de thiouréines à motif aminoacide

  摘要：

  Sixteen compounds, close to aryl or aralkylthioureines, with a beta-alanine or gamma-aminobutyric acid chain, were synthesized for in vitro screening towards 3 types of nematodes, 8 classes of opportunist germs and 34 classes of yeasts. Their anthelminthic activity was very weak, but on the other hand, 7 compounds were effective against yeasts and/or opportunist germs, with an MIC < 50-mu-g/ml.

  DOI：

  10.1016/0223-5234(91)90122-4

文献信息

• [EN] INHIBITORS OF UDP-GALACTOPYRANOSE MUTASE THWART MYCOBACTERIAL GROWTH<br/>[FR] INHIBITEURS DE UDP-GALACTOPYRANOSE EMPÊCHANT LA CROISSANCE MYCOBACTÉRIENNE
  申请人：WISCONSIN ALUMNI RES FOUND

  公开号：WO2009132310A1

  公开（公告）日：2009-10-29

  Compounds which inhibit microbial growth or attenuate the virulence of pathogen microorganisms. Compounds of the invention inhibit UDP-galactopyranose mutase (UGM) and have activity as inhibitors of microbial growth of microorganisms which contain this enzyme and particularly those microorganisms in which this enzyme is responsible for the incorporation of galactofuranose residues, particularly for uridine 5'-diphosphate (UDP) galactopyranose mutase. Compounds of the invention inhibit UDP- galactopyranose mutase (UGM) and have activity to attenuate virulence of pathogenic microorganisms, including mycobacteria.

  抑制微生物生长或减弱病原微生物毒力的化合物。本发明的化合物抑制UDP-半乳糖吡喃糖醇异构酶（UGM），并具有抑制含有该酶的微生物生长的活性，特别是那些该酶负责将半乳糖呋喃糖醇残基纳入其中的微生物，特别是尿苷5'-二磷酸（UDP）半乳糖吡喃糖醇异构酶。本发明的化合物抑制UDP-半乳糖吡喃糖醇异构酶（UGM），并具有减弱病原微生物毒力的活性，包括分枝杆菌。
• Formation of 3-Substituted 2-Thio-4-oxo-hexahydro-1,3-diazines and 2-Substituted Imino-6-oxo-1,3-thiazanes from 1-Substituted 3-Carboxyethylthioureas and Interconversion of Both Cyclic Systems
  作者：A. Prosen、B. Stanovnik、M. Tišler

  DOI：10.1021/jo01029a503

  日期：1964.6
• Formation of dihydrouracils via cyclization of N-substituted 3-thioureidopropanoic acids and facile desulfurization
  作者：Carina M.L. Delpiccolo、Fernando Albericio、Robert A. Schiksnis、Enrique L. Michelotti

  DOI：10.1016/j.tet.2007.06.042

  日期：2007.9

  Cyclization of N-3 substituted 3-thioureidopropanoic acids in isobutyric anhydride at high temperature resulted in the unexpected formation of N-3, N-1-substituted dihydrouracils, as confirmed by thorough spectroscopic characterization. A mechanism based on the identification of intermediates observed at lower reaction temperatures is proposed. (C) 2007 Elsevier Ltd. All rights reserved.
• Synthèse, activité antiparasitaire et antifongique de thiouréines à motif aminoacide
  作者：R Caujolle、M Payard、PR Loiseau、H Amarouch、MD Linas、JP Séguéla、C Bories、PM Loiseau、P Gayral

  DOI：10.1016/0223-5234(91)90122-4

  日期：1991.10

  Sixteen compounds, close to aryl or aralkylthioureines, with a beta-alanine or gamma-aminobutyric acid chain, were synthesized for in vitro screening towards 3 types of nematodes, 8 classes of opportunist germs and 34 classes of yeasts. Their anthelminthic activity was very weak, but on the other hand, 7 compounds were effective against yeasts and/or opportunist germs, with an MIC < 50-mu-g/ml.
• A Facile Synthesis and Chemoselective Reactions of Dihydrothiouracils
  作者：Vipin Nair、Varun Kumar、Gopal Khatik、Anang Pal、Mohan Praneeth、Sanjay Bhattarai

  DOI：10.1055/s-0032-1317133

  日期：——

  A highly efficient procedure was devised for the synthesis of 3-(3-arylthioureido)propanoic/butanoic acid and its cyclization to (3-aryl/3-aryl-6-methyl)-2-thioxotetrahydropyrimidin-4(1H)-one derivatives. Carbonyl diimidazole proved to be a very effective coupling reagent for the cyclization. Studies carried out to examine the ambident nature of the thioamide moiety towards substitution reactions demonstrated the preference for alkylation at sulfur, and acylation and 1,4-addition at nitrogen.