苯基-(4-苯基-2-苯基氨基-噻唑-5-基)-甲酮 | 4123-32-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 苯基-(4-苯基-2-苯基氨基-噻唑-5-基)-甲酮
• 英文名称: phenyl-1-(4-phenyl-2-phenylamino-1,3-thiazol-5-yl)methanone
• 英文别名: 2-phenylamino-4-phenyl-5-benzoylthiazole；(2-anilino-4-phenyl-thiazol-5-yl)-phenyl-methanone；(2-anilino-4-phenyl-thiazol-5-yl)-phenyl ketone；(2-Anilino-4-phenyl-thiazol-5-yl)-phenyl-keton；2-N-Phenylamino-4-phenyl-5-benzoylthiazole；2-Phenylamino-4-phenyl-5-benzoyl-thiazol；Phenyl-(4-phenyl-2-phenylamino-thiazol-5-yl)-methanone；(2-anilino-4-phenyl-1,3-thiazol-5-yl)-phenylmethanone
• CAS: 4123-32-4
• 化学式: C₂₂H₁₆N₂OS
• 分子量: 356.448
• InChiKey: LQFHHNJNCSFAOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934100090

反应信息

• 作为反应物：
  描述：

  苯基-(4-苯基-2-苯基氨基-噻唑-5-基)-甲酮 在 sodium nitrite 作用下， 以 溶剂黄146 为溶剂， 生成 [2-(N-nitroso-anilino)-4-phenyl-thiazol-5-yl]-phenyl-methanone
  参考文献：
  名称：

  Ziemelis,Z. et al., Doklady Chemistry, 1965, vol. 164, p. 840 - 843

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(5-benzoyl-4-phenyl-thiazol-2-yl)-N-phenyl-acetamide 在 盐酸 作用下， 生成 苯基-(4-苯基-2-苯基氨基-噻唑-5-基)-甲酮
  参考文献：
  名称：

  Muraw'ewa; Schtschukina, Doklady Akademii Nauk SSSR, 1959, vol. 126, p. 1274,1275, 1277

  摘要：

  DOI：

文献信息

• One Pot Synthesis and Antimicrobial Activity of Substituted 2-Aminothiazoles
  作者：Abdullah Sulaiman Al-Ayed

  DOI：10.14233/ajchem.2015.19092

  日期：——

  In this work, we described a preparation of substituted 2-aminothiazoles by two different methods using a one-pot procedure and starting from methoxymethylene-3-aryl-thiourea (2). The synthesized 2-aminothiazoles (5a-h) were characterized on the basis of elemental analysis and their spectral (IR, 1H NMR and 13C NMR) data and evaluated their biological activities. The majority of compounds were found to exhibit significant antimicrobial activity.

  在这项工作中，我们描述了通过两种不同的方法，使用一步法从甲氧基亚甲基-3-芳基-硫脲（2）开始制备取代的2-氨基噻唑。合成的2-氨基噻唑（5a-h）通过元素分析及其光谱（IR、1H NMR和13C NMR）数据进行表征，并评估了其生物活性。大多数化合物被发现具有显著的抗微生物活性。
• An efficient one-pot synthesis of functionally diverse 2-aminothiazoles from isothiocyanates, amidines/guanidines and halomethylenes
  作者：Hitesh B. Jalani、Amit N. Pandya、Dhaivat H. Pandya、Jayesh A. Sharma、V. Sudarsanam、Kamala K. Vasu

  DOI：10.1016/j.tetlet.2013.07.122

  日期：2013.9

  efficient one-pot method for the synthesis of 2-aminothiazoles using simple starting materials like isothiocyanates, amidines/guanidines and various halomethylenes is reported. The synthesis of 2-aminothiazoles involves reactions such as nucleophilic addition, S-alkylation and intramolecular nucleophilic substitution in which amines departs as the leaving group.

  报道了一种有效的一锅法，该方法使用诸如异硫氰酸酯，am /胍和各种卤代亚甲基之类的简单原料来合成2-氨基噻唑。2-氨基噻唑的合成涉及诸如亲核加成，S-烷基化和分子内亲核取代的反应，其中胺作为离去基团离开。
• Iodine‐Mediated Three‐Component Strategy to Synthesize 2‐Aminothiazoles from β‐Diketones/β‐ketoesters, Arylamines and Ammonium Thiocyanate
  作者：Abigail Philips、Ajithkumar Arumugam、Yuvaprabhu Eswaramoorthy、Siva Senthil Kumar Boominathan、Gopal Chandru Senadi

  DOI：10.1002/ejoc.202201233

  日期：2022.12.12

  A one-pot, three-component protocol for the synthesis of 2-aminothiazoles promoted by iodine from readily available starting materials such as b-diketones/b-ketoesters, arylamines, and NH4SCN has been developed. A wide range of arylamines was tolerated well to produce the expected polysubstituted 2-aminothiazoles in moderate to good yields. The characteristic features of this methodology include operational

  已经开发了一种一锅三组分方案，用于从容易获得的起始材料（如 b-二酮/b-酮酯、芳基胺和 NH4SCN）合成 2-氨基噻唑。广泛的芳胺耐受性良好，以中等至良好的产率生产预期的多取代 2-氨基噻唑。该方法的特点包括操作简便、无金属反应条件、克级可扩展性、官能团耐受性和反应时间短。
• Dahiya, Rajinder; Pujari, H. K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 966
  作者：Dahiya, Rajinder、Pujari, H. K.

  DOI：——

  日期：——
• 2-Amino-5-benzoyl-4-phenylthiazoles: Development of potent and selective adenosine A1 receptor antagonists
  作者：Anja B. Scheiff、Swapnil G. Yerande、Ali El-Tayeb、Wenjin Li、Gajanan S. Inamdar、Kamala K. Vasu、Vasudevan Sudarsanam、Christa E. Müller

  DOI：10.1016/j.bmc.2010.01.072

  日期：2010.3

  A series of 2-amino-5-benzoyl-4-phenylthiazole derivatives was investigated in radioligand binding studies at adenosine receptor (AdoR) subtypes with the goal to obtain potent and A(1)-selective antagonists. Acylation of the 2-amino group was found to be crucial for high A(1) affinity. The best compound of the present series was 2-benzoylamino-5-p-methylbenzoyl-4-phenylthiazole (16m) showing a K-i value of 4.83 nM at rat and 57.4 nM at human A(1) receptors combined with high selectivity versus the other AdoR subtypes. The compound behaved as an antagonist in GTP shift assays at A(1) receptors. Compound 16m may serve as a new lead structure for the development of second-generation non-xanthine-derived A(1) antagonists which have potential as novel drugs. (C) 2010 Elsevier Ltd. All rights reserved.