(5-thioxo-4,5-dihydro-[1,3,4]thiadiazol-2-yl)-carbamic acid ethyl ester | 55327-40-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (5-thioxo-4,5-dihydro-[1,3,4]thiadiazol-2-yl)-carbamic acid ethyl ester
• 英文别名: 2-Aethoxycarbonamido-5-mercapto-1,3,4-thiadiazol；ethyl N-(5-sulfanyl-1,3,4-thiadiazol-2-yl)carbamate；ethyl N-(2-sulfanylidene-3H-1,3,4-thiadiazol-5-yl)carbamate
• CAS: 55327-40-7
• 化学式: C₅H₇N₃O₂S₂
• 分子量: 205.261
• InChiKey: OKJDHIGLNFMGQQ-UHFFFAOYSA-N

物化性质

• 熔点：
  204-205 °C
• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5-thioxo-4,5-dihydro-[1,3,4]thiadiazol-2-yl)-carbamic acid ethyl ester 在 氯 、 溶剂黄146 作用下， 生成 (chloro-[1,3,4]thiadiazol-2-yl)-carbamic acid ethyl ester
  参考文献：
  名称：

  Petrow et al., Journal of the Chemical Society, 1958, p. 1508,1511

  摘要：

  DOI：
• 作为产物：
  描述：

  (N'-thiocarbamoyl-hydrazinothiocarbonyl)-carbamic acid ethyl ester 在 盐酸 作用下， 以 乙醇 为溶剂， 生成 (5-thioxo-4,5-dihydro-[1,3,4]thiadiazol-2-yl)-carbamic acid ethyl ester
  参考文献：
  名称：

  双脲的化学-I：硫代双脲和双硫脲的乙氧羰基衍生物的环化

  摘要：

  乙氧基羰基异硫氰酸酯与氨基脲或硫代氨基脲的相互作用分别产生1-乙氧基羰基-2-硫代双脲或联硫脲。前者可与酸中的2-乙氧基碳酰胺基-5-羟基-1,3,4-噻二唑或2（H）-氨基甲酰基-3-羟基-5-烷硫基1,2,4-三唑环化，因此在碱性介质中生成3-羟基-5-巯基-1,2,4-三唑 1-乙氧基羰基联硫脲的闭环类似地进行，在酸的影响下提供5-氨基（或巯基）-2-乙氧基碳酰胺基-1,3,4-噻二唑。碱的作用产生了衍生自3-羟基-5-巯基-1,2,4-三唑的化合物；在选定的实例中，对2（H）-苯基硫代氨基甲酰基衍生物的分离阐明了该反应的过程。1-乙氧基羰基联硫脲的水合肼解产生4-氨基-3-肼基-5-巯基-1,2,4-三唑。

  DOI：

  10.1016/0040-4020(77)80391-8

文献信息

• Chemistry of biureas—II
  作者：R. Esmail、F. Kurzer

  DOI：10.1016/0040-4020(77)80392-x

  日期：1977.1

  Carbonohydrazide and its thio-analogue undergo di-addition with ethoxycarbonyl isothiocyanate. The reaction terminates at the mono-addition stage when one of the hydrazine moieties of the (thio)carbonohydrazide is blocked. The resulting 6-(substiiuted)amino-1-ethoxycarbonyl-thiobiureas and bithioureas are cyclised to the appropriate 1-ethoxycarbonamido-1,3,4-thiadiazoles by acids, and to mercapto-1

  碳酰肼及其硫代类似物与乙氧基羰基异硫氰酸酯进行双加成反应。当（硫代）碳酰肼的肼部分之一被封端时，反应在单加成阶段终止。将所得的6-（取代的）氨基-1-乙氧基羰基-硫代双脲和联硫脲通过酸环化为合适的1-乙氧基碳酰胺基-1,3,4-噻二唑，并通过碱环化为巯基-1,2,4-三唑。
• Design, synthesis, and docking studies of new 1,3,4-thiadiazole-2-thione derivatives with carbonic anhydrase inhibitory activity
  作者：Mohammed K. Abdel-Hamid、Atef A. Abdel-Hafez、Nawal A. El-Koussi、Nadia M. Mahfouz、Alessio Innocenti、Claudiu T. Supuran

  DOI：10.1016/j.bmc.2007.07.044

  日期：2007.11

  A new series of 1,3,4-thiadiazole-2-thione derivatives have been prepared and assayed for the inhibition of three physiologically relevant carbonic anhydrase (CA, EC 4.2. 1. 1) isozymes, the cytosolic human isozymes I and II, and the transmembrane, tumor-associated hCA IX. Against hCA I the investigated thiones, showed inhibition constants in the range of 2.55-222 mu M, against hCA II in the range of 2.0-433 mu M, and against hCA IX in the range of 1.25-148 mu M. Compound 5c, 4-(4,5-dihydro-5-thioxo-1,3,4thiadi izol-2-yl)-1-(5-nitro-2-oxoindolin-3-ylidene)semicarbazide showed interesting inhibition of the turnor-associated hCA IX with K-1 value of 1.25 mu M, being the first non-sulforiamide type inhibitor of such activity. This result is rather important taking into consideration the known antitumor activity of thiones. In addition, docking of the tested compounds into CA II active site was performed in order to predict the affinity and orientation of these compounds at the isozyme active site. The results showed similar orientation of the target compounds at CA II active site compared with reported sulfonamide type CAls with the thione group acting as a zinc-binding moiety. (C) 2007 Elsevier Ltd. All rights reserved.
• ESMAIL R.; KURZER F., TETRAHEDRON <TETR-AB>, 1977, 33, NO 15, 2007-2012
  作者：ESMAIL R.、 KURZER F.

  DOI：——

  日期：——
• KURZER F.; SECKER J. L., TETRAHEDRON<TETR-AB>, 1977, 33, NO 15, 1999-2006
  作者：KURZER F.、 SECKER J. L.

  DOI：——

  日期：——
• Petrow et al., Journal of the Chemical Society, 1958, p. 1508,1511
  作者：Petrow et al.

  DOI：——

  日期：——