N-Benzolsulfonyl-dithiocarbamidsaeure-methylester | 20902-00-5

• 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: N-Benzolsulfonyl-dithiocarbamidsaeure-methylester
• 英文别名: methyl N-(benzenesulfonyl)carbamodithioate
• CAS: 20902-00-5
• 化学式: C₈H₉NO₂S₃
• 分子量: 247.363
• InChiKey: FEGLFSLWHIVPBO-UHFFFAOYSA-N

物化性质

• 熔点：
  142 °C(Solv: benzene (71-43-2))
• 沸点：
  386.6±25.0 °C(Predicted)
• 密度：
  1.409±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-Benzolsulfonyl-dithiocarbamidsaeure-methylester 在 盐酸 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 水 、 丙酮 为溶剂， 反应 24.0h， 生成 N-[2,3-dihydro-3-(4-methoxyphenyl)-2-thiazolylidene]phenylsulfonamide
  参考文献：
  名称：

  Synthesis, structural characterization and thromboxane A2 receptor antagonistic activity of 3-substituted 2-[(arylsulfonyl)imino]-2,3-dihydrothiazolyl derivatives

  摘要：

  A series of new 2-[(arylsulfonyl)imino]-2,3-dihydrothiazolyl derivatives substituted on the heterocyclic N by a phenoxyacetic moiety was prepared according to a Hantzsch's synthesis between N, N'-disubstituted thioureas and chloroacetaldehyde. The regiochemistry of the cyclocondensation reaction was established by high resolution NMR methods. Potential thromboxane A(2)/prostaglandin H-2 (TxA(2)/PGH(2)) receptor antagonism was evaluated using human platelet aggregation assays and radioligand binding studies. The results showed that the affinity for the TxA(2)/PGH(2) receptor was strongly dependent on the position of the oxyacetic acid side chain. On the basis of the X-ray crystal analysis of compound 9f, a molecular modelling was undertaken on compounds 3d, 3e, and 3f. Comparison with the 3D structure of sulotroban was discussed. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80082-8
• 作为产物：
  描述：

  monosodium mono((phenylsulfonyl)carbonimidodithioate) 、 碘甲烷 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 N-Benzolsulfonyl-dithiocarbamidsaeure-methylester
  参考文献：
  名称：

  Synthesis, structural characterization and thromboxane A2 receptor antagonistic activity of 3-substituted 2-[(arylsulfonyl)imino]-2,3-dihydrothiazolyl derivatives

  摘要：

  A series of new 2-[(arylsulfonyl)imino]-2,3-dihydrothiazolyl derivatives substituted on the heterocyclic N by a phenoxyacetic moiety was prepared according to a Hantzsch's synthesis between N, N'-disubstituted thioureas and chloroacetaldehyde. The regiochemistry of the cyclocondensation reaction was established by high resolution NMR methods. Potential thromboxane A(2)/prostaglandin H-2 (TxA(2)/PGH(2)) receptor antagonism was evaluated using human platelet aggregation assays and radioligand binding studies. The results showed that the affinity for the TxA(2)/PGH(2) receptor was strongly dependent on the position of the oxyacetic acid side chain. On the basis of the X-ray crystal analysis of compound 9f, a molecular modelling was undertaken on compounds 3d, 3e, and 3f. Comparison with the 3D structure of sulotroban was discussed. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80082-8

文献信息

• α-Carbonic Anhydrases Possess Thioesterase Activity
  作者：Muhammet Tanc、Fabrizio Carta、Andrea Scozzafava、Claudiu T. Supuran

  DOI：10.1021/ml500470b

  日期：2015.3.12

  carboxylic, sulfonic, and phosphate esters. Here we prove by kinetic, spectroscopic, and MS studies that they also possess thioesterase activity with a dithiocarbamate ester as a substrate (PhSO2NHCSSMe). Its CA-mediated hydrolysis leads to benzenesulfonamide, methyl mercaptan, and COS. The CA thioesterase activity may be useful for designing prodrug enzyme inhibitors, whereas some CA isoforms may use this activity

  α-碳酸酐酶（CAs，EC 4.2.1.1）具有催化多功能性，可与羧酸，磺酸和磷酸酯作为酯酶使用。在这里，我们通过动力学，光谱和MS研究证明，它们也具有以二硫代氨基甲酸酯为底物（PhSO2NHCSSMe）的硫酯酶活性。它的CA介导的水解作用会导致苯磺酰胺，甲硫醇和COS。CA硫酯酶的活性可能对设计前药酶抑制剂有用，而某些CA同工型可能会利用此活性来调节生理/病理过程，这可能适合药物开发。具有多种作用机制的代理。
• Hans; Dehne, Pharmazie, 1983, vol. 38, # 7, p. 441 - 442
  作者：Hans、Dehne

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  日期：——
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Ag: MVol.B7, 1.20.6.3, page 103 - 104
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• Hans; Dehne, Pharmazie, 1981, vol. 36, # 7, p. 474 - 476
  作者：Hans、Dehne

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  日期：——
• Gompper,R.; Haegele,W., Chemische Berichte, 1966, vol. 99, p. 2885 - 2899
  作者：Gompper,R.、Haegele,W.

  DOI：——

  日期：——