(p-fluorobenzylidene)cyanothioacetamide | 68029-40-3

• 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: (p-fluorobenzylidene)cyanothioacetamide
• 英文别名: (E)-2-cyano-3-(4-fluorophenyl)prop-2-enethioamide；2-Cyano-3-(4-fluorophenyl)-2-propenethioamide
• CAS: 68029-40-3
• 化学式: C₁₀H₇FN₂S
• 分子量: 206.243
• InChiKey: TXTBVZMAVKCLRA-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 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：
  81.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (p-fluorobenzylidene)cyanothioacetamide 在 N-甲基吗啉 、 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 6.02h， 生成 5-cyano-4-(4-fluorophenyl)-2-methyl-6-phenacylsulfanyl-N-phenylpyridine-3-carboxamide
  参考文献：
  名称：

  Acetoacetanilides in synthesis of 4-aryl-5-arylcarbamoyl-6-methyl-3-cyanopyridine-2(1H)-thiones

  摘要：

  DOI：

  10.1007/bf02321397
• 作为产物：
  描述：

  2-氰基硫代乙酰胺 、 对氟苯甲醛 在 N-甲基吗啉氧化物 作用下， 以 乙醇 为溶剂， 以62%的产率得到(p-fluorobenzylidene)cyanothioacetamide
  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

• Reactions of Cyanothioformamide and Thiohydantoin Derivatives With Some Arylidenes of Cyanothioacetamide and Other Elecetrophilic and Nucleophilic Reagents
  作者：A. M. Sh. El-Sharief、F. F. Mahmoud、N. M. Taha、E. M. Ahmed

  DOI：10.1080/104265090517343

  日期：2005.2

  Abstract N-(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)cyanothioformamide was synthesized from the corresponding 4-amino-pyrazole. Various cyanothioformamides were reacted with different arylidenes of cyanothioacetamide to produce either 4-imino-5-thioxo-3-(pyrroline & pyrrolidine)carbonitrile or pyrrolo[3,2-d]thiazole. Interaction of thiohydantoin with the arylidenes of either malononitrile

  摘要 以相应的4-氨基-吡唑为原料合成了N-(1,5-二甲基-3-氧代-2-苯基-2,3-二氢-1H-吡唑-4-基)氰硫代甲酰胺。各种氰硫代甲酰胺与氰硫代乙酰胺的不同亚芳基反应生成 4-imino-5-thioxo-3-(pyrroline & pyrrolidine)carbonitrile 或吡咯并 [3,2-d] 噻唑。乙内酰脲与丙二腈或氰基硫代乙酰胺的亚芳基的相互作用提供了相同的 5-氨基噻喃[2,3-d]-咪唑-6-腈。此外，乙内酰脲与氯乙酸的苯胺和邻氨基苯甲酸反应分别生成噻吩并[2,3-d]-咪唑-2-酮和咪唑并[4,5-b]喹啉-2,9-二酮。
• Stereoselective Synthesis of<i>trans</i>-2,3-Disubstituted 5-Amino-4-cyano-2,3-dihydrothiophenes
  作者：A. M. Shestopalov、O. P. Bogomolova、V. P. Litvinov

  DOI：10.1055/s-1991-26445

  日期：——

  Interaction of 1-(1-adamantylcarbonylmethyl)pyridinium bromide (1) with arylmethylenecyanothioacetamides 2 proceeds stereoselectively with formation of 2-(1-adamantylcarbonyl)-5-amino-3-aryl-4-cyano-2,3-dihydrothiophenes. Dihydrothiophenes were obtained in a good yield by three-component condensation of pyridinium bromide 1, aldehydes and cyanothioacetamide in presence of triethylamine.

  1-(1-金刚烷基羰基甲基)溴化吡啶鎓（1）与芳基亚甲基硫代氰乙酰胺 2 相互作用，立体选择性地生成 2-(1-金刚烷基羰基)-5-氨基-3-芳基-4-氰基-2,3-二氢噻吩。 在三乙胺存在下，通过溴化吡啶鎓 1、醛类和硫代氰乙酰胺的三组分缩合，可以获得收率很高的二氢噻吩。
• 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
• Unexpected formation of 4-aryl-3-cyano-6-phenylpyridine-2(1H-thiones from the reaction of arylmethylenecyanothioacetamides with benzoyl-1,1,1-trifluoroacetone
  作者：V. D. Dyachenko、A. N. Chernega

  DOI：10.1007/s10593-006-0027-0

  日期：2005.12
• Goncharenko, M. P.; Sharanin, Yu. A.; Shestopalov, A. M., Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 7.2, p. 1362 - 1370
  作者：Goncharenko, M. P.、Sharanin, Yu. A.、Shestopalov, A. M.、Litvinov, V. P.、Turov, A. V.

  DOI：——

  日期：——