5-(2'-aminophenyl)-1,3,4-thiadiazole-2-thiol | 51805-88-0

• 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: 5-(2'-aminophenyl)-1,3,4-thiadiazole-2-thiol
• 英文别名: 5-(2-amino-phenyl)-3H-[1,3,4]thiadiazole-2-thione；2-(2-Aminophenyl)-5-mercapto-1,3,4-thiadiazol；5-(2-aminophenyl)-3H-1,3,4-thiadiazole-2-thione
• CAS: 51805-88-0
• 化学式: C₈H₇N₃S₂
• mdl: MFCD06381406
• 分子量: 209.296
• InChiKey: GQGQUZHRDAYNOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  、 5-(2'-aminophenyl)-1,3,4-thiadiazole-2-thiol 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以32%的产率得到2-((5-(2-aminophenyl)-1,3,4-thiadiazol-2-yl)thio)-N-(6-nitro-1H-benzimidazol-2-yl)acetamide
  参考文献：
  名称：

  Azolylthioacetamides as a potent scaffold for the development of metallo-β-lactamase inhibitors

  摘要：

  In an effort to develop new inhibitors of metallo-beta-lactamases (MbLs), twenty-eight azolylthioacetamides were synthesized and assayed against MbLs. The obtained benzimidazolyl and benzioxazolyl substituted 1-19 specifically inhibited the enzyme ImiS, and 10 was found to be the most potent inhibitor of ImiS with an IC50 value of 15 nM. The nitrobenzimidazolyl substituted 20-28 specifically inhibited NDM-1, with 27 being the most potent inhibitor with an IC50 value of 170 nM. Further studies with 10, 11, and 27 revealed a mixed inhibition mode with competitive and uncompetitive inhibition constants in a similar range as the IC50 values. These inhibitors resulted in a 2-4-fold decrease in imipenem MIC values using E. coli cells producing ImiS or NDM-1. While the source of uncompetitive (possibly allosteric) inhibition remains unclear, docking studies indicate that 10 and 11 may interact orthosterically with Zn2 in the active site of CphA, while 27 could bridge the two Zn(II) ions in the active site of NDM-1 via its nitro group. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.10.038
• 作为产物：
  描述：

  邻氨基苯甲酸 在 盐酸 、 二硫化碳 、 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 44.0h， 生成 5-(2'-aminophenyl)-1,3,4-thiadiazole-2-thiol
  参考文献：
  名称：

  2-氨基苯甲酸及其苯甲酰胺衍生物对核糖核酸酶及其N-和S-葡糖苷的合成及抗菌活性

  摘要：

  通过使D-葡萄糖与5-（2'-氨基亚苯基）-1,3,4-恶二唑-2硫醇7（a， b），5-（2'-氨基亚苯基）-1,3,4-噻二唑-2-硫醇8（a，b），5-（2'-氨基亚苯基）-1,2,4-三唑-3-硫醇9（ a，b）和5-（2′-氨基亚苯基）-4-N-氨基-1,2,4-三唑-3-硫醇10（a，b）。硫醇7（a，b）-10（a，b）是由酰肼3（a，b）合成的，酰肼3（a，b）已经由2-氨基苯甲酸及其苯甲酰氨基衍生物合成。所有合成的化合物均通过IR，UV，1H13CNMR进行表征。在体外针对以下微生物测试了核糖核酸酶和S-糖苷的代表：两种革兰氏阳性细菌金黄色葡萄球菌和蜡状芽孢杆菌，以及两种革兰氏阴性细菌大肠杆菌，铜绿假单胞菌显示出明显的效果。支链淀粉被用作阳性标准。

  DOI：

  10.13005/ojc/320528

文献信息

• An Efficient and Convenient Synthesis of 2-Thio[1,2,4]triazolo[1,5-c]quinazoline and its Derivatives
  作者：Alexandr V. Karpenko、Sergey I. Kovalenko、Svetlana V. Shishkina、Oleg V. Shishkin

  DOI：10.1007/s00706-006-0545-6

  日期：2006.12

  reaction. The title compound 2-thio[1,2,4]triazolo[1,5- c ]quinazoline was obtained after treatment of 4-hydrazinoquinazoline with potassium ethylxanthogenate via a facile in situ Dimroth -like rearrangement of the expected [4,3- c ] system. Its structure was established by X-ray diffraction study and confirmed by an independent synthesis, starting from o -aminobenzonitrile.

  将带有二硫化碳的4-羟基喹唑啉进行再循环反应。 通过乙基黄原酸钾通过 预期的[4,3-]的原位 Dimroth 样重排 用乙基黄原酸钾处理4-肼基喹唑啉后，获得标题化合物2-硫代[1,2,4]三唑并[1,5- c ]喹唑啉。 c ]系统。它的结构是通过X射线衍射研究确定的，并通过独立合成确认，从 邻 氨基苯甲腈开始 。
• Reaction of carbon disulfide with 4-hydrazinoquinazoline
  作者：Gary M. Coppola、Goetz E. Hardtmann

  DOI：10.1021/jo00930a050

  日期：1974.8
• Gegen Thermolyse stabilisierte Formmassen mit geringem Monomerengehalt
  申请人：BAYER AG

  公开号：EP0050261B1

  公开（公告）日：1985-08-14
• Azolylthioacetamides as a potent scaffold for the development of metallo-β-lactamase inhibitors
  作者：Yang Xiang、Ya-Nan Chang、Ying Ge、Joon S. Kang、Yi-Lin Zhang、Xiao-Long Liu、Peter Oelschlaeger、Ke-Wu Yang

  DOI：10.1016/j.bmcl.2017.10.038

  日期：2017.12

  In an effort to develop new inhibitors of metallo-beta-lactamases (MbLs), twenty-eight azolylthioacetamides were synthesized and assayed against MbLs. The obtained benzimidazolyl and benzioxazolyl substituted 1-19 specifically inhibited the enzyme ImiS, and 10 was found to be the most potent inhibitor of ImiS with an IC50 value of 15 nM. The nitrobenzimidazolyl substituted 20-28 specifically inhibited NDM-1, with 27 being the most potent inhibitor with an IC50 value of 170 nM. Further studies with 10, 11, and 27 revealed a mixed inhibition mode with competitive and uncompetitive inhibition constants in a similar range as the IC50 values. These inhibitors resulted in a 2-4-fold decrease in imipenem MIC values using E. coli cells producing ImiS or NDM-1. While the source of uncompetitive (possibly allosteric) inhibition remains unclear, docking studies indicate that 10 and 11 may interact orthosterically with Zn2 in the active site of CphA, while 27 could bridge the two Zn(II) ions in the active site of NDM-1 via its nitro group. (C) 2017 Elsevier Ltd. All rights reserved.
• Synthetic Studies and Antibacterial Activity of Nucleobases and their N- and S-Glucosidesfrom 2-Amino Benzoic Acid and its Benzamido Derivatives
  作者：Samia Benhammadi、Salimairaten Salimairaten、Adil Othman

  DOI：10.13005/ojc/320528

  日期：2016.10.25

  have been synthesized from hydrazides 3(a,b) which already been synthesized from 2-aminobenzoic acid and its benzamido derivative. All synthesized compounds were characterized by IR, UV,1Hand13CNMR. Nucleobases and a representative of S-glycoside were tested in vitro against the following microorganisms: two Gram-positive bacteria Staphylococcus aureus and Bacillus cereusand two Gram-negative bacteria

  通过使D-葡萄糖与5-（2'-氨基亚苯基）-1,3,4-恶二唑-2硫醇7（a， b），5-（2'-氨基亚苯基）-1,3,4-噻二唑-2-硫醇8（a，b），5-（2'-氨基亚苯基）-1,2,4-三唑-3-硫醇9（ a，b）和5-（2′-氨基亚苯基）-4-N-氨基-1,2,4-三唑-3-硫醇10（a，b）。硫醇7（a，b）-10（a，b）是由酰肼3（a，b）合成的，酰肼3（a，b）已经由2-氨基苯甲酸及其苯甲酰氨基衍生物合成。所有合成的化合物均通过IR，UV，1H13CNMR进行表征。在体外针对以下微生物测试了核糖核酸酶和S-糖苷的代表：两种革兰氏阳性细菌金黄色葡萄球菌和蜡状芽孢杆菌，以及两种革兰氏阴性细菌大肠杆菌，铜绿假单胞菌显示出明显的效果。支链淀粉被用作阳性标准。