2-(4-甲氧基苯基)-3-[(4-甲氧基苯基)甲基]-1,3-噻唑烷-4-酮 | 918538-40-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-(4-甲氧基苯基)-3-[(4-甲氧基苯基)甲基]-1,3-噻唑烷-4-酮
• 英文名称: 2-(4-methoxyphenyl)-3-(4-methoxybenzyl)-1,3-thiazolidin-4-one
• 英文别名: 3-(4-methoxybenzyl)-2-(4-methoxyphenyl)-1,3-thiazolidin-4-one；2-(4-Methoxyphenyl)-3-[(4-methoxyphenyl)methyl]-1,3-thiazolidin-4-one
• CAS: 918538-40-6
• 化学式: C₁₈H₁₉NO₃S
• 分子量: 329.42
• InChiKey: LPCGZPBDKODJPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  64.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  dithiodiacetic anhydride 、 (E)-N-(4-甲氧基苄基)-1-(4-甲氧基苯基)甲亚胺 以 2-甲基四氢呋喃 为溶剂， 以86%的产率得到2-(4-甲氧基苯基)-3-[(4-甲氧基苯基)甲基]-1,3-噻唑烷-4-酮
  参考文献：
  名称：

  使用二硫代二甘醇酐意外合成 2-烯基和 2-芳基-4-噻唑烷酮

  摘要：

  环酸酐，包括硫包埋酸酐，如硫二甘醇酸酐，是通过与亚胺的正式环加成反应（即卡斯塔尼奥利-库什曼反应 (CCR)）合成复杂有机分子的有用偶极合成子。在这里，我们公开了一种嵌入二硫化物的酸酐（即，二硫代二甘醇酐）出人意料地与芳基醛亚胺进行了有效的形式环加成反应，得到了官能化的 4-噻唑烷酮，而没有因 CCR 引起的并发症。重要的是，当使用 1,3-氮杂二烯时，得到的 2-alkenyl-4-thiazolidinones 没有因磺胺-迈克尔反应或 Tamura 反应引起的并发症。这些 4-噻唑烷酮构成了几种药物的核心，这些药物具有广泛的生物活性，包括抗 HIV 和抗癌。目前的策略消除了对巯基乙酸的需求，这是一种与强烈难闻气味相关的替代环化伙伴。随之而来的N,S-杂环然后参与几个选择性片段生长过程，包括氧化成亚砜、砜和环氧砜。

  DOI：

  10.1039/d2nj03719j

文献信息

• Synthesis and Antimycobacterial Activity of 2-aryl-3-(arylmethyl)-1,3-thiazolidin-4-ones
  作者：Claudia R.B. Gomes、Marcele Moreth、Victor Facchinetti、Marcus V.N. de Souza、Walcimar T. Vellasco Junior、Maria Cristina da Silva Lourenco、Wilson Cunico

  DOI：10.2174/157018010791163451

  日期：2010.6.1

  Fifteen new heterocyclic thiazolidinones have been synthesized from one-pot reactions of piperonylamine, arenealdehydes and mercaptoacetic acid. These compounds plus ten 2-aryl-3-(benzyl)-1,3-thiazolidin-4-ones which had been previously synthesized, were evaluated as antibacterial agents against Mycobacterium tuberculosis H37Rv using the Alamar Blue susceptibility test and their activity expressed as the minimum inhibitory concentration (MIC) in μg/mL. Six of the series exhibited modest activity when compared to the first line drugs such as isoniazid (INH) and rifampicin (RIP). Therefore this class of compounds could be a good starting point to develop new lead compounds in the treatment of multi-drug resistant tuberculosis.

  通过哌丙基胺、异醛和巯基乙酸的一锅反应，合成了 15 个新的杂环噻唑烷酮。采用阿拉玛蓝药敏试验，将这些化合物和以前合成的 10 个 2-芳基-3-（苄基）-1,3-噻唑烷-4-酮作为抗结核分枝杆菌 H37Rv 的抗菌剂进行了评估，其活性以最小抑菌浓度（MIC）表示，单位为 μg/mL。与异烟肼（INH）和利福平（RIP）等一线药物相比，六种系列化合物表现出适度的活性。因此，这类化合物可能是开发治疗耐多药结核病新先导化合物的良好起点。
• An Unexpected Formation of 2-Aryl-3-benzyl-1,3-thiazolidin-4-ones
  作者：Wilson Cunico、Liliane Capri、Claudia Gomes、Rosangela Sizilio、Solange Wardell

  DOI：10.1055/s-2006-950213

  日期：2006.10

  The reactions of l-valine, arenealdehydes, mercaptoacetic acid and DIPEA produce 2-aryl-3-benzyl-1,3-thiazolidin-4-ones with moderate yields (48-65%). Characterization of the 1,3-thiazolidin-4-ones was achieved by NMR and confirmed by X-ray crystallography.

  L-缬氨酸、芳烃醛、巯基乙酸和 DIPEA 反应生成 2-芳基-3-苄基-1,3-噻唑烷-4-酮，产率中等 (48-65%)。 1,3-噻唑烷-4-酮的表征通过 NMR 实现，并通过 X 射线晶体学证实。
• One-pot synthesis of 2-isopropyl-3-benzyl-1,3-thiazolidin-4-ones and 2-phenyl-3-isobutyl-1,3-thiazolidin-4-ones from valine, arenealdehydes and mercaptoacetic acid
  作者：Wilson Cunico、Claudia R.B. Gomes、Maria de Lourdes G. Ferreira、Liliane R. Capri、Marcio Soares、Solange M.S.V. Wardell

  DOI：10.1016/j.tetlet.2007.06.101

  日期：2007.8

  A three-component one-pot synthesis of 2-isopropyl-3-benzyl-1,3-thiazolidin-4-ones and 2-phenyl-3-isobutyl-1,3-thiazolidin-4-ones front valine, arenealdehydes and mercaptoacetic acid with good yields is reported. Characterization of products was generally achieved by NMR techniques and specifically for 2-isopropyl-3-(4-nitrobenzyl)-1,3-thiazolidin-4-one by X-ray crystallography. (C) 2007 Elsevier Ltd. All rights reserved.
• Five symmetrically substituted 2-aryl-3-benzyl-1,3-thiazolidin-4-ones: supramolecular structures in zero, one and two dimensions
  作者：Wilson Cunico、Liliane R. Capri、C. R. B. Gomes、Solange M. S. V. Wardell、John N. Low、Christopher Glidewell

  DOI：10.1107/s0108270106055272

  日期：2007.2.15

  There are no direction-specifc interactions between the molecules of 3-(2-methoxybenzyl)-2-(2-methoxyphenyl)-1,3-thiazolidin- 4-one, C18H19NO3S, (I); the molecules of 3-(4-nitrobenzyl)-2-(4-nitrophenyl)-1,3-thiazolidin-4-one, C16H13N3O5S, (II), are linked by four independent C-(HO)-O-... hydrogen bonds into complex chains of fused rings. In 3-(4-methoxybenzyl)- 2-(4-methoxyphenyl)-1,3-thiazolidin-4-one, (III), isomeric with (I), the molecules are linked into sheets by a combination of C-(HO)-O-... and C-H-...pi(arene) hydrogen bonds, while in 3-(2- nitrobenzyl)- 2-(2- nitrophenyl)-1,3-thiazolidin-4- one, (IV), isomeric with (II), the sheets are built from three independent C-(HO)-O-... hydrogen bonds and one C-H-...pi(arene) hydrogen bond, and reinforced by an aromatic pi-pi stacking interaction. In 3-(2-fluorobenzyl)-2(2-fluorophenyl)-1,3-thiazolidin-4-one, C16H13F2NOS, (V), where the 2-aryl ring exhibits orientational disorder, the molecules are linked into sheets by a combination of C-(HO)-O-... and C-H-...pi(arene) hydrogen bonds, and the sheets are linked in pairs, forming bilayers, by an aromatic pi-pi stacking interaction.