3-(4-bromo-phenyl)-2-phenylimino-thiazolidin-4-one | 36969-54-7

• 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: 3-(4-bromo-phenyl)-2-phenylimino-thiazolidin-4-one
• 英文别名: 3-(4-Brom-phenyl)-2-phenylimino-thiazolidin-4-on；3-p-Bromo-phenyl-2-phenylimino-4-thiazolidon；3-(4-Bromophenyl)-2-phenylimino-1,3-thiazolidin-4-one；3-(4-bromophenyl)-2-phenylimino-1,3-thiazolidin-4-one
• CAS: 36969-54-7
• 化学式: C₁₅H₁₁BrN₂OS
• 分子量: 347.235
• InChiKey: UBVUSTWKXPZPHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  58
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-bromo-phenyl)-2-phenylimino-thiazolidin-4-one 在 溴 作用下， 生成 3-(2,4-dibromo-phenyl)-2-phenylimino-thiazolidin-4-one
  参考文献：
  名称：

  Farooq; Hunter, Journal of the Indian Chemical Society, 1932, vol. 9, p. 545,549, 550

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(p-bromophenyl)-N'-phenylthiourea 生成 3-(4-bromo-phenyl)-2-phenylimino-thiazolidin-4-one
  参考文献：
  名称：

  THE REACTIONS OF THE FORMAMIDINES. VIII. SOME THIAZOLIDONE DERIVATIVES.

  摘要：

  DOI：

  10.1021/ja01436a027

文献信息

• Synthesis and Biological Evaluation of Halogenated 2-Arylimino-3-arythiazolidine- 4-ones Containing Benzoic Acid Fragments as Antibacterial Agents
  作者：Jie Zhang、Likang Zheng、Huayong Liu、Dan Zhao、Di Qu、Shiqing Han

  DOI：10.2174/15701808113109990031

  日期：2013.10.1

  A series of halogenated 2-arylimino-3-ary-thiazolidine-4-ones containing (5-furan-2-yl)-benzoic acid or (5-thiophene-2-yl)-benzoic acid fragments were synthesized, and evaluated in vitro for their antibacterial activity, antibiofilm activity, erythrocyte hemolysis and cytotoxicity. Compounds (7c, 7f, 7i, 7n and 7p) exhibited excellent potency in inhibiting the growth of Staphylococcus epidermidis ATCC35984 (minimal inhibitory concentration (MIC): 0.8 μg/mL). The five compounds also presented promising antibiofilm activity against S. epidermidis ATCC35984 and none of them showed obvious hemolytic activity and cytotoxicity. Further antibacterial effects of the selected five compounds (7c, 7f, 7i, 7n and 7p) against clinical isolates (methicillin-resistant Staphylococcus epidermidis and methicillin-resistant Staphylococcus aureus) were investigated in comparison with methicillin and ampicillin.7p showed the most potent antibacterial activities among the synthesized compounds.

  合成了包含(5-呋喃-2-基)苯甲酸或(5-噻吩-2-基)苯甲酸片段的一系列卤代2-芳基亚胺-3-芳基-噻唑烷-4-酮，并在体外评估了它们的抗菌活性、抗生物膜活性、红细胞溶血和细胞毒性。化合物(7c、7f、7i、7n和7p)表现出优异的抑制表皮葡萄球菌ATCC35984生长的功效（最小抑制浓度(MIC)：0.8 μg/mL）。这五种化合物还显示出对表皮葡萄球菌ATCC35984有前景的抗生物膜活性，并且均未表现出明显的溶血活性和细胞毒性。进一步研究了选定的五种化合物(7c、7f、7i、7n和7p)对临床分离株（耐甲氧西林表皮葡萄球菌和耐甲氧西林金黄色葡萄球菌）的抗菌效果，并与甲氧西林和氨苄西林进行了比较。7p在合成的化合物中显示出最强的抗菌活性。
• A facile, rapid, one-pot regio/stereoselective synthesis of 2-iminothiazolidin-4-ones under solvent/scavenger-free conditions
  作者：Murugan Sathishkumar、Sangaraiah Nagarajan、Poovan Shanmugavelan、Murugan Dinesh、Alagusundaram Ponnuswamy

  DOI：10.3762/bjoc.9.78

  日期：——

  A rapid and efficient one pot solvent/scavenger-free protocol for the synthesis of 2-iminothiazolidin-4-ones has been developed. Interestingly, the regio/stereoselective synthesis affords the regioisomeric (Z)-3-alkyl/aryl-2-(2-phenylcyclohex-2-enylimino)thiazolidin-4-one as the sole product in good yield. The selectivities observed have been rationalized based on the relative magnitude of the allylic strains developed during the course of the reaction. This is the first report wherein the impact of allylic strains in directing the regiocyclization has been noted.

  已经开发了一种快速高效的单锅无溶剂/清除剂合成2-亚氨基噻唑啉-4-酮的方案。有趣的是，区域/立体选择性合成只产生区异构体(Z)-3-烷基/芳基-2-(2-苯基环己-2-烯基亚氨基)噻唑啉-4-酮，收率良好。观察到的选择性是基于反应过程中产生的联烯应变相对大小的合理化。这是第一篇注意到联烯应变对定向区域环化的影响的报告。
• Pandey,H.N.; Ram,V.J., Journal of the Indian Chemical Society, 1972, vol. 49, p. 171 - 173
  作者：Pandey,H.N.、Ram,V.J.

  DOI：——

  日期：——
• Rao,R.P.; Raj,S., Journal of the Indian Chemical Society, 1973, vol. 50, p. 366
  作者：Rao,R.P.、Raj,S.

  DOI：——

  日期：——
• THE REACTIONS OF THE FORMAMIDINES. VIII. SOME THIAZOLIDONE DERIVATIVES.
  作者：F. B. Dains、Roy Irvin、C. G. Harrel

  DOI：10.1021/ja01436a027

  日期：1921.3