(E)-2-cyano-3-(4-nitrophenyl)prop-2-enethioamide | 68029-55-0

• 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: (E)-2-cyano-3-(4-nitrophenyl)prop-2-enethioamide
• CAS: 68029-55-0
• 化学式: C₁₀H₇N₃O₂S
• 分子量: 233.25
• InChiKey: ZJUPLUDEWMWRRF-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-2-cyano-3-(4-nitrophenyl)prop-2-enethioamide 以 乙醇 为溶剂， 反应 20.0h， 生成 7,7-dimethyl-4-(4-nitrophenyl)-5-oxo-2-sulfanyl-1,4,6,8-tetrahydroquinoline-3-carbonitrile;morpholine
  参考文献：
  名称：

  Goncharenko, M. P.; Sharanin, Yu. A.; Shestopalov, A. M., Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 7.2, p. 1362 - 1370

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氰基硫代乙酰胺 、 对硝基苯甲醛 在 N-甲基吗啉氧化物 作用下， 以 乙醇 为溶剂， 以58%的产率得到(E)-2-cyano-3-(4-nitrophenyl)prop-2-enethioamide
  参考文献：
  名称：

  5-Arylidenethioxothiazolidinones as Inhibitors of Tyrosyl–DNA Phosphodiesterase I

  摘要：

  Tyrosyl-DNA phosphodiesterase I (Tdp1) is a cellular enzyme that repairs the irreversible topoisomerase I (Top1)-DNA complexes and confers chemotherapeutic resistance to Top1 inhibitors. Inhibiting Tdp1 provides an attractive approach to potentiating clinically used Top1 inhibitors. However, despite recent efforts in studying Tdp1 as a therapeutic target, its inhibition remains poorly understood and largely underexplored. We describe herein the discovery of arylidene thioxothiazolidinone as a scaffold for potent Tdp1 inhibitors based on an initial tyrphostin lead compound 8. Through structure-activity relationship (SAR) studies we demonstrated that arylidene thioxothiazolidinones inhibit Tdp1 and identified compound 50 as a submicromolar inhibitor of Tdp1 (IC50 = 0.87 mu M). Molecular modeling provided insight into key interactions essential for observed activities. Some derivatives were also active against endogenous Tdp1 in whole cell extracts. These findings contribute to advancing the understanding on Tdp1 inhibition.

  DOI：

  10.1021/jm3008773

文献信息

• Heterocycles Synthesis through Reactions of Nucleophiles with Acrylonitriles. 7. A Novel and Facile One-Step Synthesis of 4<i>H</i>-Thiopyrans
  作者：Fathy Fahim Abdel-Latif

  DOI：10.1246/bcsj.62.3768

  日期：1989.11

  Several new 4H-thiopyrans were synthesized via a facile one-step method. Structures and reaction mechanisms are also reported and supported by another synthetic routes.

  通过一种简单的一步法合成了几种新的4H-噻吡呋。还报告了它们的结构和反应机制，并由其他合成路线进行了支持。
• Reaction of 3-Aryl-2-Cyanoprop-2-ene- Thioamides With Bromonitromethane: A new Method for the Synthesis of Functionalized 1,2,4-Thiadiazoles
  作者：V. V. Dotsenko、S. G. Krivokolysko

  DOI：10.1007/s10593-014-1507-2

  日期：2014.7

  ioamides with bromonitromethane leads to the products of oxidative dimerization, (2Е,2′E)-2,2′-(1,2,4-thiadiazole-3,5-diyl)bis(3-arylacrylonitriles). Their structure was confirmed by the counter synthesis through the oxidation of 3-aryl-2-cyanoprop-2-ene-thioamides by DMSO–HCl system.

  3-芳基-2-氰基丙-2-烯硫酰胺与溴硝基甲烷的反应导致氧化二聚化产物（2Å，2'E）-2,2'-（1,2,4-噻二唑-3,5-二基）双（3-芳基丙烯腈）。通过DMSO-HCl系统氧化3-芳基-2-氰基丙-2-烯硫基酰胺进行反合成，证实了它们的结构。
• Bromine- and iodine-mediated oxidative dimerization of cyanothioacetamide derivatives: synthesis of new functionalized 1,2,4-thiadiazoles
  作者：Bogdan S. Krivokolysko、Victor V. Dotsenko、Nikolay A. Pakholka、Polina G. Dakhno、Vladimir D. Strelkov、Nicolai A. Aksenov、Inna V. Aksenova、Sergey G. Krivokolysko

  DOI：10.1007/s13738-022-02688-4

  日期：2023.3

  6-amino-2,4-diaryl-3,5-dicyano-3,4-dihydro-2H-thiopyran-3-carbothioamides, with bromine or iodine in DMF. The scope and limitations of the reaction are discussed. Partial ring bromination of starting thioamide was observed only in the case of (E)-2-cyano-3-(4-hydroxy-3-methoxyphenyl)prop-2-enethioamide. When treated with bromine in DMF, 2-cyano-2-cyclopentylideneethanthioamide gives 2,2′-(1,2,4-thiadiazole-3

  ( 2E,2 ' E )-2,2'-(1,2,4-thiadiazole-3,5-diyl) bis [3-aryl(hetaryl)-2-cyanoprop-2-entioamides] 通过处理获得( E )-3-aryl(hetaryl)-2-cyanoprop-2-entioamides 或其 [4 + 2] 二聚产物，6-amino-2,4-diaryl-3,5-dicyano-3,4-dihydro- 2 H -thiopyran-3-carbothioamides，在 DMF 中含有溴或碘。讨论了反应的范围和局限性。仅在 ( E )-2-cyano-3-(4-hydroxy-3-methoxyphenyl)prop-2-enethioamide 的情况下观察到起始硫代酰胺的部分环溴化。当在 DMF 中用溴处理时，2-cyano-2-cyclopentylideneethioamide
• Ensembles of rings with a coumarin unit 1. Synthesis of 3-(2-R-thiazol-4-yl)-and 3-(4-R-thiazol-2-yl)coumarins
  作者：Ya. V. Belokon'、S. N. Kovalenko、A. V. Silin、V. M. Nikitchenko

  DOI：10.1007/bf02290865

  日期：1997.10
• Shestopalov, A. M.; Sharanin, Yu. A.; Rodinovskaya, L. A., Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 7.2, p. 1371 - 1375
  作者：Shestopalov, A. M.、Sharanin, Yu. A.、Rodinovskaya, L. A.、Litvinov, V. P.

  DOI：——

  日期：——