N-(biphenyl-2-thiocarbamoyl)-4-phenylcarboxamide | 19249-97-9

• 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-(biphenyl-2-thiocarbamoyl)-4-phenylcarboxamide
• 英文别名: N-([1,1'-biphenyl]-2-ylcarbamothioyl)benzamide；N-(biphenyl-2-ylcarbamothioyl)benzamide；N-Benzoyl-N'-(o-biphenylyl)-thioharnstoff；2-{[(Benzoylamino)carbothioyl]amino}-1,1'-biphenyl；N-[(2-phenylphenyl)carbamothioyl]benzamide
• CAS: 19249-97-9
• 化学式: C₂₀H₁₆N₂OS
• 分子量: 332.426
• InChiKey: VPCKNCJBXDGMQV-UHFFFAOYSA-N

物化性质

• 熔点：
  198 °C
• 密度：
  1.259±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(biphenyl-2-thiocarbamoyl)-4-phenylcarboxamide 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以99.4%的产率得到(2-苯基苯基)硫脲
  参考文献：
  名称：

  New 2-Aryliminomidazolidines. II. Synthesis and Antihypertensive Activity of 2-(Biphenylimino)imidiazolidines.

  摘要：

  为了提高FR35447（I）的持续作用时间，合成了2-(联苯亚氨基)咪唑烷（III），并对其在清醒的正常血压大鼠中的降压活性进行了测试。2-(4'-氟-[1, 1'-联苯]-2-亚氨基)咪唑烷（III l）展示了优越的降压效力，其持续作用时间与克隆宁（II）相当。文中还描述了III的结构-活性关系。

  DOI：

  10.1248/cpb.40.240
• 作为产物：
  描述：

  2-氨基联苯 、 苯甲酰基异硫氰酸酯 以 丙酮 为溶剂， 反应 1.0h， 以56.3%的产率得到N-(biphenyl-2-thiocarbamoyl)-4-phenylcarboxamide
  参考文献：
  名称：

  New 2-Aryliminomidazolidines. II. Synthesis and Antihypertensive Activity of 2-(Biphenylimino)imidiazolidines.

  摘要：

  为了提高FR35447（I）的持续作用时间，合成了2-(联苯亚氨基)咪唑烷（III），并对其在清醒的正常血压大鼠中的降压活性进行了测试。2-(4'-氟-[1, 1'-联苯]-2-亚氨基)咪唑烷（III l）展示了优越的降压效力，其持续作用时间与克隆宁（II）相当。文中还描述了III的结构-活性关系。

  DOI：

  10.1248/cpb.40.240

文献信息

• N‐Heterocyclic Carbene‐Catalyzed Atroposelective Annulation for Access to Thiazine Derivatives with C−N Axial Chirality
  作者：Tingting Li、Chengli Mou、Puying Qi、Xiaolin Peng、Shichun Jiang、Gefei Hao、Wei Xue、Song Yang、Lin Hao、Yonggui Robin Chi、Zhichao Jin

  DOI：10.1002/anie.202010606

  日期：2021.4.19

  A catalytic atroposelective cycloaddition reaction between thioureas and ynals is developed. This reaction features the first NHC‐catalyzed addition of thioureas to acetylenic acylazolium intermediates to eventually set up C−N axial chirality with excellent optical purities. The obtained axially chiral thiazine derivative products bear multiple functional groups and are feasible for further transformations

  开发了硫脲与乙醛之间的催化对位选择性环加成反应。该反应的特征是首次在NHC催化下将硫脲添加到炔基酰基唑鎓中间体中，从而最终以优异的光学纯度建立了CN轴向手性。所获得的轴向手性噻嗪衍生物产物具有多个官能团，并且对于进一步转化是可行的。
• 2-Imidazoline derivatives, process for the preparation thereof and the pharmaceutical composition of the same
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0017484A1

  公开（公告）日：1980-10-15

  Compounds of the general formula: wherein R1 is aryl which may have 1 to 5 substituent(s) selected from the groups consisting of halogen, lower alkyl, lower alkoxy, lower alkanesulfonamido, mono(or di or tri)-halo(lower)alkyl, carbomoyl, hydroxy, nitro, amino, cyano, sulfamoyl, N,N-di(lower)alkylsulfamoyl, and di(lower- )alkylamino which may form a 3 to 7-membered ring with or without an oxygen or nitrogen atom;

  通式如下的化合物 其中 R1 为芳基，可具有 1 至 5 个取代基，这些取代基可选自以下基团：卤素、低级烷基、低级烷氧基、低级烷磺酰胺基、单（或二或三）卤（低级）烷基、碳酰基、羟基、硝基、氨基、氰基、氨基磺酰基、N,N-二（低级）烷基氨基磺酰基和二（低级）烷基氨基，这些取代基可与或不与氧原子或氮原子形成 3 至 7 元环；
• Creating an Antibacterial with in Vivo Efficacy: Synthesis and Characterization of Potent Inhibitors of the Bacterial Cell Division Protein FtsZ with Improved Pharmaceutical Properties
  作者：David J. Haydon、James M. Bennett、David Brown、Ian Collins、Greta Galbraith、Paul Lancett、Rebecca Macdonald、Neil R. Stokes、Pramod K. Chauhan、Jignesh K. Sutariya、Narendra Nayal、Anil Srivastava、Joy Beanland、Robin Hall、Vincent Henstock、Caterina Noula、Chris Rockley、Lloyd Czaplewski

  DOI：10.1021/jm9016366

  日期：2010.5.27

  3-Methoxybenzamide (1) is a weak inhibitor of the essential bacterial cell division protein FtsZ. Alkyl derivatives of 1 are potent antistaphylococcal compounds with suboptimal drug-like properties. Exploration of the structure activity relationships of analogues of these inhibitors led to the identification of potent antistaphylococcal compounds with improved pharmaceutical properties.
• Gupta, K. A.; Saxena, Anil K.; Jain, Padam C., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 3, p. 228 - 233
  作者：Gupta, K. A.、Saxena, Anil K.、Jain, Padam C.

  DOI：——

  日期：——
• Structural and vibrational study on N-(biphenyl-2-thiocarbamoyl)-4-phenylcarboxamide
  作者：Aamer Saeed、Mauricio F. Erben、Michael Bolte

  DOI：10.1016/j.molstruc.2010.10.013

  日期：2011.1

  A new thiourea derivative, N-(biphenyl-2-thiocarbamoyl)-4-phenylcarboxamide, is synthesized and characterized by elemental analysis, FTIR, NMR and the single crystal X-ray diffraction study. The title compound crystallizes with two molecules in the asymmetric unit. The dihedral angle between the two aromatic rings in the biphenyl unit is 47.9(2) and 56.52(19), respectively, for the two molecules in the asymmetric unit. The molecular conformation is stabilized by intramolecular N-H ... O hydrogen bond. The crystal packing shows that the molecules form centrosymmetric dimers connected by N-H ... S hydrogen bonds. The vibrational properties have been studied by FTIR and FT-Raman spectroscopy along with quantum chemical calculations at the B3LYP/6-311 + G* level of approximation. The main normal modes related with the thioamide bands are discussed. (C) 2010 Elsevier B.V. All rights reserved.