N-(N-Phenyl-benzimidoyl)-N'-phenyl-thioharnstoff | 20800-34-4

• 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-(N-Phenyl-benzimidoyl)-N'-phenyl-thioharnstoff
• 英文别名: 1-phenyl-3-(phenyl-phenyliminomethyl)thiourea；1-phenyl-3-(N-phenylbenzimidoyl)thiourea；N-(N-phenylbenzimidoyl)-N-phenylthiourea；N-phenyl-N'-(phenyl-thiocarbamoyl)-benzamidine；N-phenyl-N'-(N-phenyl-benzimidoyl)-thiourea；N-Phenyl-N'-(N-phenyl-benzimidoyl)-thioharnstoff；(1E)-1-[anilino(phenyl)methylidene]-3-phenylthiourea
• CAS: 20800-34-4
• 化学式: C₂₀H₁₇N₃S
• 分子量: 331.441
• InChiKey: SRAXJVRQKOKBMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.5
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(N-Phenyl-benzimidoyl)-N'-phenyl-thioharnstoff 生成 N-phenyl-N'-(4-phenyl-5-thioxo-[1,2,4]dithiazolidin-3-ylidene)-benzamidine
  参考文献：
  名称：

  Goerdeler,J.; Loebach,W., Chemische Berichte, 1979, vol. 112, p. 517 - 531

  摘要：

  DOI：
• 作为产物：
  描述：

  N-苯基亚胺苄基氯 以 丙酮 为溶剂， 生成 N-(N-Phenyl-benzimidoyl)-N'-phenyl-thioharnstoff
  参考文献：
  名称：

  5-Imino-1,2,4-Thiadiazoles: First Small Molecules As Substrate Competitive Inhibitors of Glycogen Synthase Kinase 3

  摘要：

  Cumulative evidence strongly supports that glycogen synthase kinase-3 (GSK-3) is a pathogenic molecule when it is up-dysregulated, emerging as an important therapeutic target in severe unmet human diseases. GSK-3 specific inhibitors might be promising effective drugs for the treatment of devastating pathologies such as neurodegenerative diseases, stroke, and mood disorders. As GSK-3 has the ability to phosphorylate primed substrates, small molecules able to bind to this site should be perfect drug candidates, able to partially block the activity of the enzyme over some specific substrates. Here, we report substituted 5-imino-1,2,4-thiadiazoles as the first small molecules able to inhibit GSK-3 in a substrate competitive manner. These compounds are cell permeable, able to decrease inflammatory activation and to selectively differentiate neural stem cells. Overall, 5-imino-1,2,4-thiadiazoles are presented here as new molecules able to decrease neuronal cell death and to increase endogenous neurogenesis blocking the GSK-3 substrate site

  DOI：

  10.1021/jm201463v

文献信息

• Hypervalent Iodine(III)-Mediated Solvent-Free, Regioselective Synthesis of 3,4-Disubstituted 5-Imino-1,2,4-thiadiazoles and 2-Aminobenzo[<i>d</i> ]thiazoles
  作者：Nagaraju Tumula、Radha Krishna Palakodety、Sridhar Balasubramanian、Mangarao Nakka

  DOI：10.1002/adsc.201800353

  日期：2018.8.6

  A convenient approach for the synthesis of 3,4‐disubstituted 5‐imino‐1,2,4‐thiadiazoles and 2‐aminobenzo[d]thiazoles has been developed using phenyliodine diacetate (PIDA). This approach involves a metal‐free oxidative C−N, N−S and C−S bond formations under neat conditions. High regioselectivity, solvent‐free conditions, short reaction time and broad functional group compatibility are the notable features

  使用苯基乙酸二乙酸酯（PIDA）已开发出一种方便的合成3,4-二取代的5-亚氨基-1,2,4-噻二唑和2-氨基苯并[ d ]噻唑的方法。该方法涉及在纯净条件下形成无金属的氧化性C-N，N-S和C-S键。高区域选择性，无溶剂条件，较短的反应时间和广泛的官能团相容性是本报告的显着特征。
• Synthesis and regioselective [4+2] cycloaddition/nucleophilic reactions of N-arylamino-1:3-diaza-1:3-butadienes with ketenes and accompanying rearrangements
  作者：Paramita D. Dey、Arun K. Sharma、Sachchida N. Rai、Mohinder P. Mahajan

  DOI：10.1016/0040-4020(95)00372-f

  日期：1995.7

  -butadienes 4 are shown to undergo regioselective reactions with phenyl- and chloroketenes resulting in high yields of 3-aryl-2-methylthio6-phenyl-4(3H)-pyrimidinones 7. Similar reactions with bromo- and iodoketenes, resulted, via aziridinium intermediates 12, in good yields of 3-aryl-S-(N-arylamino)-2-methylthio-6-phenyl4(3H)-pyrimidinones 13, The mechanistic aspects of cycloadditions and semi-empirical

  N-Arylamino-1：3-diaza-1：3-butadienes 4与苯基和氯乙烯酮发生区域选择性反应，导致3-芳基-2-甲基硫代6-苯基-4（3H）-嘧啶酮7的高收率。经由叠氮鎓中间体12与溴和碘酮的类似反应，以高收率产生了3-芳基-S-（N-芳基氨基）-2-甲硫基-6-苯基4（3H）-嘧啶酮13，环加成反应的机理还报道了这些二氮杂丁二烯的​​半经验AM1计算结果。
• Unusual Reactivity of 2,3-diphenylcyclopropenone towards <i>N</i>-imidoylthioureas; Facile Synthesis of 3-aryl-2,5,6-triphenylpyrimidin-4(3<i>H</i>)-one (PART III)
  作者：Ashraf A. Aly、Ahmed M. NourEl-Din、Moshen A.-M. Gomaa、Alan B. Brown、Magda S. Fahmi

  DOI：10.3184/030823407x234563

  日期：2007.8

  2,3-Diphenylcyclopropenone (1) reacts with N-imidoylthioureas 2a–e to form the pyrimidin-4(3 H)-ones 5a–e. The reaction mechanism can be described as due to stepwise addition accompanied by elimination of phenyl isothiocyanate.

  2,3-Diphenylcyclopropenone (1) 与 N-imidoylthioureas 2a-e 反应生成嘧啶-4(3H)-酮 5a-e。反应机理可描述为逐步加成并伴随着异硫氰酸苯酯的消除。
• Extraction–Spectrophotometric Determination of Molybdenum(V) with Imidoyl Derivatives and Thiocyanate
  作者：Khageshwar Singh Patel、Rajendra Kumar Mishra

  DOI：10.1246/bcsj.56.2811

  日期：1983.9

  organic reagents derived from N-phenylbenzimidoyl chloride and thiourea, phenylthiourea or thiosemicarbazide react with Mo(V) in strongly acidic media in the presence of thiocyanate ions to give rise red-orange complexes, insoluble in water but soluble in benzene. The nature of the ligands has been described to be as univalent, bidentate chelating agents which may coordinate to Mo(V) to form complexes with

  来自 N-苯基苯并亚氨基酰氯和硫脲、苯基硫脲或氨基硫脲的三种新型有机试剂在强酸性介质中在硫氰酸根离子存在下与 Mo(V) 反应生成红橙色络合物，不溶于水但溶于苯。配体的性质已被描述为单价双齿螯合剂，可与 Mo(V) 配位以与 Mo 0.2SCN·SR 的组成形成络合物（SCN 表示硫氰酸根离子，SR 表示试剂的去质子化形式） . 发现配合物的摩尔吸收率在 (0.8–1.4)×104 l mol-1 cm-1 范围内，λmax, 465 nm。该方法简单、快速，对钼的选择性高。与金属相关的铁合金元素不干扰测定。
• Facile Synthesis of 4-phenyl-6-[(Z)phenylimino]-3,6-dihydro-1,3,5-thiadiazine-2,2-dicarbonitriles
  作者：Ashraf A. Aly、Kamal M. El-Shaieb

  DOI：10.3184/030823407x207086

  日期：2007.4

  N-Imidoylthioureas 2a–e reacted with 1,1,2,2-tetracyanoethylene (1) to form the thiadiazines 3a–e. In the case of 1e, tricyanovinylation of a phenyl substituent accompanied formation of the thiadiazine ring.

  N-Imidoylthioureas 2a-e 与 1,1,2,2-四氰基乙烯（1）反应生成噻二嗪类化合物 3a-e。在 1e 的情况中，苯基取代基的三氰基乙炔化伴随着噻二嗪环的形成。