1-[Amino(phenyl)methylidene]-3-(4-cyanophenyl)thiourea | 1375644-61-3

• 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: 1-[Amino(phenyl)methylidene]-3-(4-cyanophenyl)thiourea
• 英文别名: 1-[amino(phenyl)methylidene]-3-(4-cyanophenyl)thiourea
• CAS: 1375644-61-3
• 化学式: C₁₅H₁₂N₄S
• 分子量: 280.353
• InChiKey: FZYXIYNRTXBRKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[Amino(phenyl)methylidene]-3-(4-cyanophenyl)thiourea 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.05h， 以71%的产率得到4-((3-phenyl-1,2,4-thiadiazol-5-yl)amino)benzonitrile
  参考文献：
  名称：

  高价碘（III）通过分子内氧化SN键形成3-取代的5-氨基-1,2,4-噻二唑

  摘要：

  据报道，通过苯基碘（III）双（三氟乙酸）分子内氧化亚氨基硫脲的SN氮键形成，可以有效合成3-取代的5-芳基氨基-1,2,4-噻二唑。该方案具有无金属方法，广泛的底物范围，非常短的反应时间，良好或优异的收率以及简单的起始原料。

  DOI：

  10.1021/acs.joc.6b01199
• 作为产物：
  描述：

  4-氰基苯基异硫氰酸酯 、 苄脒盐酸盐 在 N,N-二异丙基乙胺 作用下， 以 异丙醇 为溶剂， 以81%的产率得到1-[Amino(phenyl)methylidene]-3-(4-cyanophenyl)thiourea
  参考文献：
  名称：

  Synthesis and biological activity of 2-aminothiazoles as novel inhibitors of PGE2 production in cells

  摘要：

  This Letter presents the synthesis and biological evaluation of a collection of 2-aminothiazoles as a novel class of compounds with the capability to reduce the production of PGE(2) in HCA-7 human adenocarcinoma cells. A total of 36 analogs were synthesized and assayed for PGE(2) reduction, and those with potent cellular activity were counter screened for inhibitory activity against COX-2 in a cell free assay. In general, analogs bearing a 4-phenoxyphenyl substituent in the R-2 position were highly active in cells while maintaining negligible COX-2 inhibition. Specifically, compound 5l (R-1 = Me, R-2 = 4-OPh-Ph, R-3 = CH(OH)Me) exhibited the most potent cellular PGE(2) reducing activity of the entire series (EC50 = 90 nM) with an IC50 value for COX-2 inhibition of >5 mu M in vitro. Furthermore, the anti-tumor activity of analog 1a was analyzed in xenograft mouse models exhibiting promising anti-cancer activity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.013

文献信息

• Hypervalent Iodine(III) Mediated Synthesis of 3-Substituted 5-Amino-1,2,4-thiadiazoles through Intramolecular Oxidative S–N Bond Formation
  作者：Arumugam Mariappan、Kandasamy Rajaguru、Noufal Merukan Chola、Shanmugam Muthusubramanian、Nattamai Bhuvanesh

  DOI：10.1021/acs.joc.6b01199

  日期：2016.8.5

  An efficient synthesis of 3-substituted-5-arylamino-1,2,4-thiadiazoles through intramolecular oxidative S–N bond formation of imidoyl thioureas by phenyliodine(III) bis(trifluoroacetate) is reported. The protocol features a metal-free approach, broad substrate scope, very short reaction times, good to excellent yields, and simple starting materials.

  据报道，通过苯基碘（III）双（三氟乙酸）分子内氧化亚氨基硫脲的SN氮键形成，可以有效合成3-取代的5-芳基氨基-1,2,4-噻二唑。该方案具有无金属方法，广泛的底物范围，非常短的反应时间，良好或优异的收率以及简单的起始原料。
• Synthesis and biological activity of 2-aminothiazoles as novel inhibitors of PGE2 production in cells
  作者：Breland Smith、Hui-Hua Chang、Federico Medda、Vijay Gokhale、Justin Dietrich、Angela Davis、Emmanuelle J. Meuillet、Christopher Hulme

  DOI：10.1016/j.bmcl.2012.03.013

  日期：2012.5

  This Letter presents the synthesis and biological evaluation of a collection of 2-aminothiazoles as a novel class of compounds with the capability to reduce the production of PGE(2) in HCA-7 human adenocarcinoma cells. A total of 36 analogs were synthesized and assayed for PGE(2) reduction, and those with potent cellular activity were counter screened for inhibitory activity against COX-2 in a cell free assay. In general, analogs bearing a 4-phenoxyphenyl substituent in the R-2 position were highly active in cells while maintaining negligible COX-2 inhibition. Specifically, compound 5l (R-1 = Me, R-2 = 4-OPh-Ph, R-3 = CH(OH)Me) exhibited the most potent cellular PGE(2) reducing activity of the entire series (EC50 = 90 nM) with an IC50 value for COX-2 inhibition of >5 mu M in vitro. Furthermore, the anti-tumor activity of analog 1a was analyzed in xenograft mouse models exhibiting promising anti-cancer activity. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of 5-Amino and 3,5-Diamino Substituted 1,2,4-Thiadiazoles by I₂-Mediated Oxidative N–S Bond Formation
  作者：Bingnan Wang、Yinggao Meng、Yiming Zhou、Linning Ren、Jie Wu、Wenquan Yu、Junbiao Chang

  DOI：10.1021/acs.joc.7b00814

  日期：2017.6.2

  An oxidative N–S bond formation reaction has been established for 1,2,4-thiadiazole synthesis employing molecular iodine as the sole oxidant. The features of the present reaction include no use of transition metals, mild reaction conditions, simple operation, and short reaction time. This versatile synthetic approach is broadly applicable to a variety of imidoyl and guanyl thiourea substrates to produce

  已经建立了利用分子碘作为唯一氧化剂合成1,2,4-噻二唑的氧化NS键形成反应。本反应的特征包括不使用过渡金属，反应条件温和，操作简单，反应时间短。这种通用的合成方法广泛适用于各种亚氨基和胍基硫脲底物，以有效和可扩展的方式分别生产5-氨基和3,5-二氨基取代的1,2,4-噻二唑衍生物。