3-(4-methylbenzyl)-2-thioxothiazolidin-4-one | 34392-97-7

• 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-methylbenzyl)-2-thioxothiazolidin-4-one
• 英文别名: 3-[(4-Methylphenyl)methyl]-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 34392-97-7
• 化学式: C₁₁H₁₁NOS₂
• mdl: MFCD02983486
• 分子量: 237.346
• InChiKey: ZEZSJEPMPURQRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  77.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3-(4-methylbenzyl)-2-thioxothiazolidin-4-one 在 盐酸 、 亚硝酸异丙酯 作用下， 以 乙醇 为溶剂， 生成 3-(4-Methylbenzyl)-5-oximino-rhodanin
  参考文献：
  名称：

  5-异硝基索尔丹宁。

  摘要：

  DOI：

  10.1021/jm01241a016
• 作为产物：
  描述：

  双(羧甲基)三硫代碳酸盐 、 4-甲基苄胺 以to give the title compound (250 mg, 53% yield)的产率得到3-(4-methylbenzyl)-2-thioxothiazolidin-4-one
  参考文献：
  名称：

  Use of Thiazolidinone Derivatives as Antiangiogenic Agents

  摘要：

  本发明涉及使用通式(I)中的化合物，其中R1、R2和X如说明书中所定义，用于制备药物组合物，用于治疗抑制HIF-1α和p300之间相互作用有益的病理情况，特别是作为治疗实体瘤的抗血管生成药物。

  公开号：

  US20080261980A1

文献信息

• Electrogenerated base-promoted synthesis of<i>N</i>-benzylic rhodanine and carbamodithioate derivatives
  作者：Khalil Tissaoui、Noureddine Raouafi、Khaled Boujlel

  DOI：10.1080/17415990903191752

  日期：2010.2

  Electrogenerated magnesium-associated cyanomethyl anions/bases obtained from the electrochemical reduction of acetonitrile and the oxidation of a sacrificial magnesium rod were successfully used to promote the addition of carbon disulfide to primary benzylic amines. Alkylation with ethyl 3-bromopropionate acid ester or with ethyl 2-bromoacetate acid ester yields the corresponding ring-opened carbamodithioate

  从乙腈的电化学还原和牺牲镁棒的氧化中获得的电生镁相关氰甲基阴离子/碱成功地用于促进二硫化碳向伯苄胺的加成。用 3-溴丙酸乙酯或 2-溴乙酸乙酯烷基化分别产生相应的开环氨基甲二硫代酸酯化合物或环状若丹宁衍生物。还评价了电生碱的量对反应产率的影响。
• Synthesis and biological evaluation of novel rhodanine-based structures with antiviral activity towards HHV-6 virus
  作者：Valentina Gentili、Giulia Turrin、Paolo Marchetti、Sabrina Rizzo、Giovanna Schiuma、Silvia Beltrami、Virginia Cristofori、Davide Illuminati、Greta Compagnin、Claudio Trapella、Roberta Rizzo、Daria Bortolotti、Anna Fantinati

  DOI：10.1016/j.bioorg.2021.105518

  日期：2022.2

  of anti-HHV6 compounds provides a valuable opportunity for developing efficient antiviral therapies. A possible target for antiviral drugs is the virus-cell fusion step. In this study, we synthetized potential fusion intermediates inhibitors based on the rhodanine structure. The obtained derivatives were tested for cytotoxicity and for antiviral activity in human cells infected with HHV6. Level of infection

  对与人类疱疹病毒 6 (HHV-6) 感染或再激活相关的疾病的认识提高，导致人们对评估可用于 HHV-6 疾病临床管理的最佳治疗方案的兴趣日益浓厚。然而，尚未批准专门用于 HHV-6 感染治疗的化合物。出于这个原因，抗 HHV6 化合物的鉴定为开发有效的抗病毒疗法提供了宝贵的机会。抗病毒药物的一个可能目标是病毒-细胞融合步骤。在这项研究中，我们合成了基于罗丹宁结构的潜在融合中间体抑制剂。测试了获得的衍生物在感染 HHV6 的人类细胞中的细胞毒性和抗病毒活性。在感染后长达 7 天的不同时间点通过病毒 DNA 定量监测感染水平。在合成衍生物中，图9e显示对病毒复制的显着抑制作用持续超过7天，这可能归因于罗丹宁部分的亲水性和疏水性取代基的特定组合。我们的结果支持使用这些两亲性融合抑制剂治疗 HHV-6 感染。
• A Concise Approach to N-Substituted Rhodanines through a Base-Assisted One-Pot Coupling and Cyclization Process
  作者：Yongxi Liang、Mei-Lin Tang、Zhipeng Huo、Chenchen Zhang、Xun Sun

  DOI：10.3390/molecules25051138

  日期：——

  An efficient approach to obtain functionalized rhodanines was developed through a base-assisted one-pot coupling and continuous cyclization of a primary amine, carbon disulfide, and methyl (2-chloroacetyl)carbamate. This conversion tolerates a broad range of functional groups and can be used to scale the preparation of N-substituted rhodanines in excellent yields.

  通过碱辅助的一锅法耦合和连续环化，开发了一种高效的方法来获得官能化的罗丹啉。该转化容忍广泛的官能团，并可用于扩大制备N-取代罗丹啉，产率极高。
• Phospholipase D inhibitors and uses thereof
  申请人：Cell Therapeutics, Inc.

  公开号：US20040002526A1

  公开（公告）日：2004-01-01

  The invention is directed to thiazolidinones and the use thereof to inhibit phospholipase D (PLD) activity. The invention further relates to methods of treating cancer and inflammatory diseases using thiazolidinones.

  该发明涉及噻唑烷酮及其用于抑制磷脂酶D（PLD）活性的用途。该发明进一步涉及使用噻唑烷酮治疗癌症和炎症性疾病的方法。
• Thiazolidinone–Peptide Hybrids as Dengue Virus Protease Inhibitors with Antiviral Activity in Cell Culture
  作者：Christoph Nitsche、Verena N. Schreier、Mira A. M. Behnam、Anil Kumar、Ralf Bartenschlager、Christian D. Klein

  DOI：10.1021/jm400828u

  日期：2013.11.14

  The protease of dengue virus is a promising target for antiviral drug discovery. We here report a new generation of peptide hybrid inhibitors of dengue protease that incorporate N-substituted 5-arylidenethiazolidinone heterocycles (rhodanines and thiazolidinediones) as N-terminal capping groups of the peptide moiety. The compounds were extensively characterized with respect to inhibition of various proteases, inhibition mechanisms, membrane permeability, antiviral activity, and cytotoxicity in cell culture. A sulfur/oxygen exchange in position 2 of the capping heterocycle (thiazolidinedione-capped vs rhodanine-capped peptide hybrids) has a significant effect on these properties and activities. The most promising in vitro affinities were observed for thiazolidinedione-based peptide hybrids containing hydrophobic groups with K-i values between 1.5 and 1.8 mu M and competitive inhibition mechanisms. Rhodanine-capped peptide hybrids with hydrophobic substituents have, in correlation with their membrane permeability, a more pronounced antiviral activity in cell culture than the thiazolidinediones.