(Z)-5-benzylidene-2-(methylthio)thiazol-4(5H)-one

• 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: (Z)-5-benzylidene-2-(methylthio)thiazol-4(5H)-one
• 英文别名: (5Z)-5-benzylidene-2-methylsulfanyl-1,3-thiazol-4-one
• 化学式: C₁₁H₉NOS₂
• 分子量: 235.331
• InChiKey: NULFHNBGVYXBKE-CLFYSBASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  80
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-5-benzylidene-2-(methylthio)thiazol-4(5H)-one 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 31.0h， 生成 (Z)-2-(5-benzyliden-4-oxo-4,5-dihydrothiazol-2-ylamino)-4-methyl-N-tosylpentanamide
  参考文献：
  名称：

  Structure-based design of rhodanine-based acylsulfonamide derivatives as antagonists of the anti-apoptotic Bcl-2 protein

  摘要：

  A series of novel rhodanine-based acylsulfonamide derivatives were designed, synthesized, and evaluated as small-molecule inhibitors of anti-apoptotic Bcl-2 protein. These compounds exhibit potent antiproliferative activity in three human tumor cell lines (Hep G2, PC-3 and B16-F10). Among them, the most potent compounds 10 and 11 bind to Bcl-2 with a K-i of 20 and 25 nM, respectively. Docking studies demonstrated that these two compounds orient similarly at the binding site of Bcl-2, and the calculated binding affinities (Glide XP score) of compound 10 is more negative than that of compound 11. The binding interactions of compounds with high binding affinity to Bcl-2 protein were analyzed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.079
• 作为产物：
  描述：

  (Z)-5-benzylidene-2-thioxothiazolidin-4-one 以90%的产率得到
  参考文献：
  名称：

  JENSEN L.; THOMSEN I.; LAWESSON S.-O., BULL. SOC. CHIM. BELG. , 1977, 86, NO 8, 639-646

  摘要：

  DOI：

文献信息

• Sulfenyl Ynamides in Gold Catalysis: Synthesis of Oxo‐functionalised 4‐aminoimidazolyl Fused Compounds by Intermolecular Annulation Reactions
  作者：Elsa M. Arce、Scott G. Lamont、Paul W. Davies

  DOI：10.1002/adsc.202000134

  日期：2020.6.15

  medicinal and agrochemical discovery programmes. Sulfenyl substituted ynamides were identified as privileged reactants affording productive gold‐catalysed annulation reactions with these and other nitrenoids. This annulation method provides selective and efficient access into geminally amino‐sulfenyl substituted nitrogen heterocycles under mild reaction conditions.

  已经设计并合成了功能化的N杂环吡啶鎓N-胺类化合物，以评估基于硝烯类化合物的环化策略在咪唑融合的氧取代框架中的重要性，该框架对医学和农业化学发现计划至关重要。亚磺酰基取代的乙酰胺被确定为特有反应物，可与这些和其他硝烯类化合物提供生产性的金催化环化反应。这种环化方法在温和的反应条件下提供了选择性和有效地进入双氨基氨基亚磺酰基取代的氮杂环的途径。
• A facile synthesis of (Z)-5-(substituted)-2-(methylthio)thiazol-4(5H)-one using microwave irradiation and conventional method
  作者：Dattatraya N. Pansare、Devanand B. Shinde

  DOI：10.1016/j.tetlet.2013.12.113

  日期：2014.1

  A new effective approach to the synthesis of some new (Z)-5-(substituted)-2-thioxothiazolidin-4-one 3a–l and (Z)-5-(substituted)-2-(methylthio)thiazol-4(5H)-one 5a–l is reported under microwave irradiation as well as conventional conditions.

  一种新的有效合成一些新的（Z）-5-（取代）-2-硫代噻唑啉酮-4-one 3a - 1和（Z）-5-（取代）-2-（甲硫基）噻唑-4（据报道，在微波辐射以及常规条件下，5 H）-1 5a - l。
• Synthesis, Structure−Activity Relationships, and in Vivo Evaluations of Substituted Di-<i>tert</i>-butylphenols as a Novel Class of Potent, Selective, and Orally Active Cyclooxygenase-2 Inhibitors. 1. Thiazolone and Oxazolone Series
  作者：Yuntao Song、David T. Connor、Robert Doubleday、Roderick J. Sorenson、Anthony D. Sercel、Paul C. Unangst、Bruce D. Roth、Richard B. Gilbertsen、Kam Chan、Denis J. Schrier、Antonio Guglietta、Dirk A. Bornemeier、Richard D. Dyer

  DOI：10.1021/jm9805081

  日期：1999.4.1

  Selective cyclooxygenase-2 (COX-2) inhibitors have been shown to be potent antiinflammatory agents with fewer side effects than currently marketed nonsteroidal antiinflammatory drugs (NSAIDs). Initial mass screening and subsequent structure-activity relationship (SAR) studies have identified 4b (PD138387) as the most potent and selective COX-2 inhibitor within the thiazolone and oxazolone series of di-tert-butylphenols. Compound 4b has an IC50 Of 1.7 mu M against recombinant human COX-2 and inhibited COX-2 activity in the J774A.1 cell line with an IC50 of 0.17 mu M. It was inactive against purified ovine COX-1 at 100 mu M and did not inhibit COX-1 activity in platelets at 20 mu M. Compound 4b was also orally active in vivo with an ED40 of 16 mg/kg in the carrageenan footpad edema (CFE) assay and caused no gastrointestinal (GI) damage in rats at the dose of 100 mg/kg but inhibited gastric prostaglandin E-2 (PGE(2)) production in rats' gastric mucosa by 33% following a dose of 100 mg/kg. The SAR studies of this chemical series revealed that the potency and selectivity are very sensitive to minor structural changes. A simple isosteric replacement led to the reversal of selectivity.
• Design and synthesis of novel bis-thiazolone derivatives as micromolar CDC25 phosphatase inhibitors: Effect of dimerisation on phosphatase inhibition
  作者：Manal Sarkis、Diem Ngan Tran、Stéphanie Kolb、Maria A. Miteva、Bruno O. Villoutreix、Christiane Garbay、Emmanuelle Braud

  DOI：10.1016/j.bmcl.2012.10.072

  日期：2012.12

  CDC25 phosphatases are involved in deregulated cell cycle progression and tumor development with poor prognosis. Among the most potent CDC25 inhibitors, quinonoid-based derivatives have been extensively studied. Dimerisation of heterocyclic quinones has led to IRC-083864, a bis-quinone compound with increased CDC25B inhibitory activity. Thirty-one bis-thiazolone derivatives were synthesized and assayed for CDC25 inhibitory activity. Most of the dimers displayed enhanced inhibitory activities with micromolar IC50 values lower than that observed for each thiazolone scaffold separately. Moreover, most of these compounds were selective CDC25 inhibitors. Dimer 40 showed an IC50 value of 2.9 mu M and could inhibit CDC25 activity without generating reactive oxygen species which is likely to occur with quinone-based inhibitors. Molecular docking studies suggested that the dimers could bind simultaneously to the active site and the inhibitor binding pocket. (C) 2012 Elsevier Ltd. All rights reserved.
• Jadhav, Santosh A.; Shioorkar, Mahesh. G.; Chavan, Omprakash S., Indian Journal of Heterocyclic Chemistry, 2016, vol. 25, # 3-4, p. 201 - 207
  作者：Jadhav, Santosh A.、Shioorkar, Mahesh. G.、Chavan, Omprakash S.、Sarkate, Aniket P.、Farooqui, Mazahar、Shinde, Devanand. B.、Pardeshi, Rajendra K.

  DOI：——

  日期：——