2-(4-phenyl-thiazol-2-ylamino)-thiazol-4-one | 52413-92-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-phenyl-thiazol-2-ylamino)-thiazol-4-one
• 英文别名: (2Z)-2-[(4-phenyl-1,3-thiazol-2-yl)imino]-1,3-thiazolidin-4-one
• CAS: 52413-92-0
• 化学式: C₁₂H₉N₃OS₂
• 分子量: 275.355
• InChiKey: YULCUMBOJUSBNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(4-phenyl-thiazol-2-ylamino)-thiazol-4-one 在 溴 、 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 生成 5-bromo-5-[bromo-(2-chloro-phenyl)-methyl]-2-(4-phenyl-thiazol-2-ylamino)-thiazol-4-one
  参考文献：
  名称：

  Dhal,P.N. et al., Journal of the Indian Chemical Society, 1973, vol. 50, p. 680 - 684

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基-4-苯基噻唑 在 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 5.0h， 生成 2-(4-phenyl-thiazol-2-ylamino)-thiazol-4-one
  参考文献：
  名称：

  新型二元噻唑基杂环化合物的合成及其作为 COVID-19 主要蛋白酶 (Mpro) 抑制剂的分子对接研究。

  摘要：

  分离的多核二元杂环化合物包含噻唑结构单元与苯并呋喃、吡咯、噻唑或噻吩通过甲酰胺和/或仲胺作为连接点结合。其合成策略基于利用 2-氯乙酰氨基-4-苯基噻唑与水杨醛、乙腈衍生物、硫氰酸铵、3-巯基丙烯腈衍生物和/或 3-巯基丙烯酸酯衍生物进行环缩合反应合成二元杂环化合物。已制备的基于二元噻唑的杂环作为蛋白酶 (Mpro) 抑制剂通过分子对接进行了研究，以使用羟氯喹作为参考分子来可视化它们的方向和与 COVID-19 单元的相互作用。

  DOI：

  10.1134/s1070363221090231

文献信息

• 2-Thiazolylimino/Heteroarylimino-5-arylidene-4-thiazolidinones as New Agents with SHP-2 Inhibitory Action
  作者：A. Geronikaki、P. Eleftheriou、P. Vicini、I. Alam、A. Dixit、A. K. Saxena

  DOI：10.1021/jm8004306

  日期：2008.9.11

  SHP-2, a nonreceptor protein tyrosine phosphatase encoded by the PTPN11 gene, mediates cell signaling by growth factors and cytokines via the RAS/MAP kinase pathway. Somatic mutations in PTPN11 gene account for approximately 18% of juvenile myelomonocytic leukemia (JMML) patients. Moreover, SHP-2 mutations leading to continuously active enzyme were found in more than 50% of Noonan syndrome patients and are considered to be responsible for the high tendency of these patients to juvenile leukemias and other cancer types. Recently SHP-2 became a new drug target, but till flow little has been done in this field. In the present study, 172-thiazolylimino/heteroarylimino-5-arylidene-4-thiazolidinones divided into three series of derivatives bearing thiazole-, benzo[d]thiazole-, and benzo[d]isothizole rings were tested for SHP-2 inhibitory activity. Most of the compounds were good SHP-2 inhibitors. Benzo[d]thiazole derivatives exhibited the best inhibitory action. Docking studies revealed that hydrophobic interactions and hydrogen bond formation stabilize enzyme-inhibitor complex.
• 5-Nitro-heteroarylidene analogs of 2-thiazolylimino-4-thiazolidinones as a novel series of antibacterial agents
  作者：Nouraddin Hosseinzadeh、Mohammad Hasani、Alireza Foroumadi、Hamid Nadri、Saeed Emami、Nasrin Samadi、Mohammad Ali Faramarzi、Parastoo Saniee、Farideh Siavoshi、Neda Abadian、Yasaman Mahmoudjanlou、Amirhossein Sakhteman、Alireza Moradi、Abbas Shafiee

  DOI：10.1007/s00044-012-0224-6

  日期：2013.5

  In the pursuit of novel antibacterial agents with the 2-thiazolylimino-4-thiazolidinone as a core structure, a series of 5-nitro-heteroarylidene and 5-(2-oxoindolin-3-ylidene) analogs of 2-thiazolylimino-5-arylidene-4-thiazolidinone were synthesized and their antibacterial activities were evaluated against some strains of Gram-positive and Gram-negative bacteria, as well as Helicobacter pylori strains. Biological data indicated that 5-nitrofuran analog 5a and 5-nitroimidazole analog 7a containing no substitutions on the thiazole ring were the most potent compounds.
• Synthesis and biological evaluation of some 5-arylidene-2-(1,3-thiazol-2-ylimino)-1,3-thiazolidin-4-ones as dual anti-inflammatory/antimicrobial agents
  作者：I. Apostolidis、K. Liaras、A. Geronikaki、D. Hadjipavlou-Litina、A. Gavalas、M. Soković、J. Glamočlija、A. Ćirić

  DOI：10.1016/j.bmc.2012.10.046

  日期：2013.1

  As a part of our ongoing studies in developing new derivatives as dual antimicrobial/anti-inflammatory agents we describe the synthesis of novel 5-arylidene-2-(1,3-thiazol-2-ylimino)-1,3-thiazolidin-4-ones. All newly synthesized compounds were tested for their anti-inflammatory activity using carrageenan mouse paw edema bioassay. Their COX-1/LOX inhibitory activities were also determined. Moreover, all compounds were evaluated for their antimicrobial and antifungal activities against a panel of Gram positive, Gram negative bacteria and moulds. All tested compounds exhibited better antimicrobial activity than commercial drugs, bifonazole, ketoconazole, ampicillin and streptomycin. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of New Binary Thiazole-Based Heterocycles and Their Molecular Docking Study as COVID-19 Main Protease (Mpro) Inhibitors
  作者：E. Abdel-Latif、T. K. Khatab、A. Fekri、M. E. Khalifa

  DOI：10.1134/s1070363221090231

  日期：2021.9

  those is based on utilization of 2-chloroacetamido-4-phenylthiazole in the synthesis of binary heterocyclic compounds by cyclocondensation with salicylic aldehyde, acetonitrile derivatives, ammonium thiocyanate, 3-mercaptoacrylonitrile derivatives, and/or 3-mercaptoacrylate derivatives. The prepared binary thiazole-based heterocycles have been studied as protease (Mpro) inhibitors by molecular docking for

  分离的多核二元杂环化合物包含噻唑结构单元与苯并呋喃、吡咯、噻唑或噻吩通过甲酰胺和/或仲胺作为连接点结合。其合成策略基于利用 2-氯乙酰氨基-4-苯基噻唑与水杨醛、乙腈衍生物、硫氰酸铵、3-巯基丙烯腈衍生物和/或 3-巯基丙烯酸酯衍生物进行环缩合反应合成二元杂环化合物。已制备的基于二元噻唑的杂环作为蛋白酶 (Mpro) 抑制剂通过分子对接进行了研究，以使用羟氯喹作为参考分子来可视化它们的方向和与 COVID-19 单元的相互作用。
• Dhal,P.N. et al., Journal of the Indian Chemical Society, 1973, vol. 50, p. 680 - 684
  作者：Dhal,P.N. et al.

  DOI：——

  日期：——