N-phenyl-benzimidoyl isothiocyanate | 20800-27-5

• 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-phenyl-benzimidoyl isothiocyanate
• 英文别名: N-Phenyl-benzimidoyl-isothiocyanat；N-Phenyl-benzimidoylisothiocyanat；N-phenylbenzimidoyl isothiocyanate；N-phenylbenzenecarboximidoyl isothiocyanate
• CAS: 20800-27-5
• 化学式: C₁₄H₁₀N₂S
• 分子量: 238.313
• InChiKey: XXVALTCWSBUCNK-UHFFFAOYSA-N

物化性质

• 沸点：
  358.4±25.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-phenyl-benzimidoyl isothiocyanate 在 ammonium hydroxide 、 氯 作用下， 以 四氯化碳 、 二氯甲烷 、 乙腈 为溶剂， 反应 14.5h， 生成 5-amino-2,3-diphenyl-[1,2,4]thiadiazolium; chloride
  参考文献：
  名称：

  Zyabrev, V.S.; Kharchenko, A.V.; Pirozhenko, V.V., Journal of Organic Chemistry USSR (English Translation), 1988, vol. 24, p. 1583 - 1590

  摘要：

  DOI：
• 作为产物：
  描述：

  N-苯甲酰替苯胺 在 氯化亚砜 作用下， 以 丙酮 为溶剂， 反应 4.5h， 生成 N-phenyl-benzimidoyl isothiocyanate
  参考文献：
  名称：

  2,3,5-取代的 [1,2,4]-噻二唑作为 SARS-CoV-2 3C 样蛋白酶共价抑制剂的发现、合成和机制研究

  摘要：

  3C 样蛋白酶 (3CL pro ) 对于严重急性呼吸系统综合症冠状病毒 2 (SARS-CoV-2) 的复制和转录至关重要，使其成为治疗 2019 年冠状病毒病 (COVID-19) 的有希望的靶点。在这项研究中，发现一系列 2,3,5-取代的 [1,2,4]-噻二唑类似物能够抑制 3CL pro作为亚微摩尔水平的非拟肽共价结合剂，IC 50值范围为 0.118至 0.582 μM。有趣的是，这些化合物还显示出以相同水平的IC 50抑制 PL pro值，但对胰凝乳蛋白酶、组织蛋白酶 B 和组织蛋白酶 L 等蛋白酶的影响可忽略不计。随后，在基于细胞的测定中评估了这些化合物的抗病毒能力，化合物 6g 显示出有效的抗病毒活性，EC 50值为7.249 μM . 有人提出，这些化合物通过开环复分解反应机制与催化性半胱氨酸 145 共价结合。为了理解这种共价结合反应，我们选择了化合物6a，作为已确

  DOI：

  10.1016/j.ejmech.2023.115129

文献信息

• 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。
• Synthesis of Functionally Substituted 1,3-Diaza-1,3-butadienes
  作者：S. N. Mazumdar、M. P. Mahajan

  DOI：10.1055/s-1990-26892

  日期：——

  Three methods for the synthesis of various stable 1,3-diaza-1,3-butadienes from easily available thiourea derivatives are reported.

  报道了三种从易得的硫脲衍生物合成各种稳定的1,3-二氮-1,3-丁二烯的方法。
• Ried,W.; Kaiser,L., Justus Liebigs Annalen der Chemie, 1976, p. 395 - 399
  作者：Ried,W.、Kaiser,L.

  DOI：——

  日期：——
• Synthesis and Biological Evaluation of 2,3,5-Substituted [1,2,4]Thiadiazoles as Allosteric Modulators of Adenosine Receptors
  作者：Adrianus M. C. H. van den Nieuwendijk、Daniele Pietra、Laura Heitman、Anikó Göblyös、Adriaan P. IJzerman

  DOI：10.1021/jm030863d

  日期：2004.1.1

  A number of 2,3,5-substituted [1,2,4]thiadiazole analogues of SCH-202676 (N-(2,3-diphenyl-[1,2,4]thiadiazole-5(2H)-ylidene)methanamine, 7a) were synthesized and tested as potential allosteric modulators of adenosine receptors. All compounds were capable of displacing the binding of the radiolabeled agonist [H-3]CCPA to human A(1) adenosine receptors, whereas modest and varying effects were observed on the binding of [H-3]DPCPX, a radiolabeled antagonist for this receptor subtype. Four compounds, 7a (SCH-202676), 7k (LUF5792), 71 (LUF5794), and 8e (LUF5789), were selected for more detailed characterization. They all proved allosteric inhibitors of agonist binding, with 7k being most potent, whereas their effects on antagonist binding were more ambiguous. Subsequently, experiments were done on human adenosine A(2A) and A(3) receptors. Compounds 7a and 71 displayed peculiar displacement characteristics of both radiolabeled agonist and antagonist binding to A(2A) receptors, whereas 7a showed some activity on A(3) receptors.
• 5-Imino-1,2,4-Thiadiazoles: First Small Molecules As Substrate Competitive Inhibitors of Glycogen Synthase Kinase 3
  作者：Valle Palomo、Daniel I. Perez、Concepcion Perez、Jose A. Morales-Garcia、Ignacio Soteras、Sandra Alonso-Gil、Arantxa Encinas、Ana Castro、Nuria E. Campillo、Ana Perez-Castillo、Carmen Gil、Ana Martinez

  DOI：10.1021/jm201463v

  日期：2012.2.23

  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