2-ethoxycarbonylmethylthio-2-thiazolin-4-one | 51126-34-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 2-ethoxycarbonylmethylthio-2-thiazolin-4-one
• 英文别名: 2-carboethoxymethylthio-2-thiazolin-4-one；ethyl 2-(4-oxo-4,5-dihydrothiazol-2-ylthio)acetate；2-carbethoxymethylthio-2-thiazolin-4-one；2-carbethoxymethylthio-2-thiazol-4(5H)-one；Ethyl [(4-oxo-4,5-dihydro-1,3-thiazol-2-yl)thio]acetate；ethyl 2-[(4-oxo-1,3-thiazol-2-yl)sulfanyl]acetate
• CAS: 51126-34-2
• 化学式: C₇H₉NO₃S₂
• mdl: MFCD00726014
• 分子量: 219.285
• InChiKey: RAYUAJGVGHMQCV-UHFFFAOYSA-N

物化性质

• 熔点：
  78-79 °C(Solv: isopropanol (67-63-0))
• 沸点：
  327.9±44.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  对甲氨基酚 、 2-ethoxycarbonylmethylthio-2-thiazolin-4-one 以 异丙醇 为溶剂， 反应 2.0h， 以73%的产率得到2-[(4-hydroxyphenyl)methylamino]thiazol-4(5H)-one
  参考文献：
  名称：

  Synthesis of 5-arylidene-2-amino-4-azolones and evaluation of their anticancer activity

  摘要：

  Series of novel 5-arylidene-2-arylaminothiazol-4(5H)-ones and 2-aryl(benzyl)amino-1H-imidazol-4(5H)ones were synthesized from appropriate 2-alkylthioazol-4-ones using nucleophilic substitution in position 2 by various anilines and benzylamines and Knoevenagel reaction. X-ray structural studies of 22 revealed the structure to be intermediate between amino and imino tautomeric forms. All the target compounds were evaluated for the anticancer activity in vitro in standard National Cancer Institute 60 cancer cell lines assay. Majority of compounds showed significant antitumor cytotoxicity effect at micromolar and submicromolar level (Mean Log GI(50) ranges -5.77 to -4.35). Some of the most potent compounds, namely 10 and 13, possessed selectively high effect on all leukemia cell lines at submicromolar level (Mean Log GI50 [leukemia lines], respectively, -6.41 and -6.29), which are probably associated with immunosuppressive activity. Individual cancer cell lines sensitivity to synthesized compounds and SAR studies are discussed. COMPARE analysis allowed to disclose probable modes of anticancer action for synthesized compounds, in particular showed number of high correlations with activity patterns of alkylating agents (PCC similar to 0.606-0.731). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.073
• 作为产物：
  描述：

  罗丹宁 、 氯乙酸乙酯 在 三乙胺 作用下， 以 异丙醇 、 丙酮 为溶剂， 反应 5.0h， 以60%的产率得到2-ethoxycarbonylmethylthio-2-thiazolin-4-one
  参考文献：
  名称：

  [EN] SPIRO-THIAZOLONES
  [FR] SPIRO-THIAZOLONES

  摘要：

  本发明提供了作为V1a受体调节剂的螺环噻唑酮，特别是作为V1a受体拮抗剂，它们的制备方法，含有它们的药物组合物以及它们作为药物的用途。本化合物在周围和中枢作用下，对于不当分泌加压素、焦虑、抑郁症、强迫症、自闭症谱系障碍、精神分裂症、攻击性行为和相位错位睡眠障碍，特别是时差反应等症状具有治疗作用。

  公开号：

  WO2016075181A1

文献信息

• Design, Synthesis, and Anti-Inflammatory Evaluation of Novel Diphenylthiazole-Thiazolidinone Hybrids
  作者：Ahmed H. Abdelazeem、Samir A. Salama、Ibrahim A. Maghrabi

  DOI：10.1002/ardp.201500104

  日期：2015.7

  A series of diphenylthiazole–thiazolidinone hybrids was synthesized and evaluated in vitro and in vivo as anti‐inflammatory/analgesic agents. The inhibition of cyclooxygenase (COX) enzymes was suggested as a molecular mechanism for the hybrids to exert their anti‐inflammatory action. Of these compounds, 13b, 14, and 15b showed the most potent COX inhibitory activity with IC50 values between 2.03 and

  合成了一系列二苯基噻唑-噻唑烷酮杂化物，并作为抗炎/镇痛剂在体外和体内进行了评估。环加氧酶（COX）的抑制被认为是杂种发挥抗炎作用的分子机制。在这些化合物中，13b、14 和 15b 显示出最有效的 COX 抑制活性，IC50 值介于 2.03 和 12.27 µM 之间，但具有不同的选择性。使用三种动物模型在体内进一步评估了所有化合物的抗炎/镇痛活性。有趣的是，COX 测定的结果与体内测定的结果一致，其中最有效的 COX 抑制剂 13b、14 和 15b 与双氯芬酸相比表现出最高的抗炎/镇痛活性。相反，
• Synthesis of novel thiazolone-based compounds containing pyrazoline moiety and evaluation of their anticancer activity
  作者：Dmytro Havrylyuk、Borys Zimenkovsky、Olexandr Vasylenko、Lucjusz Zaprutko、Andrzej Gzella、Roman Lesyk

  DOI：10.1016/j.ejmech.2008.09.032

  日期：2009.4

  for obtaining a series of 5-arylidene derivatives 3–10, 13–18. Alternatively 11, 12 and their 5-arylidene derivatives were synthesized by means of 3-phenyl-5-aryl-1-thiocarbamoyl-2-pyrazoline as S,N-binucleophile via [2 + 3]-cyclocondensation approach. The structures of compounds were determined by 1H, 13C NMR, LC–MS, EI-MS and X-ray analysis. The in vitro anticancer activity of synthesized compounds

  为了检查抗癌活性，获得了几种含有5-芳基-3-苯基-4，5-二氢-1 H-吡唑-1-基骨架的新型基于噻唑酮的化合物。5-芳基-3-苯基-4,5-二氢吡唑与4-硫代-2--2-噻唑烷酮或2-乙氧基甲硫基-2-噻唑啉-4-酮的反应生成起始4-（1和2）或2-取代（11和12），其中使用了Knoevenagel缩合获得一系列5-亚芳基衍生物的噻唑酮3 - 10，13 - 18。可替代地11，12并通过[2 + 3]-环缩合反应，以3-苯基-5-芳基-1-硫代氨基甲酰基-2-吡唑啉为S，N-双亲核试剂合成了它们的5-亚芳基衍生物。化合物的结构通过1 H，13 C NMR，LC-MS，EI-MS和X射线分析确定。在体外合成的化合物的抗癌活性是由国家癌症研究所测试，其中大部分显示在白血病，黑色素瘤，肺癌，结肠癌，中枢神经系统癌，卵巢癌，肾癌，前列腺癌和乳腺癌细胞系中的抗癌活性。讨论了结构与活性之间的关
• Synthesis and anticancer activity evaluation of 4-thiazolidinones containing benzothiazole moiety
  作者：Dmytro Havrylyuk、Ludmyla Mosula、Borys Zimenkovsky、Olexandr Vasylenko、Andrzej Gzella、Roman Lesyk

  DOI：10.1016/j.ejmech.2010.08.008

  日期：2010.11

  alternatively by a counter synthesis method based on the reaction of 2-chloro-N-(6-methylbenzothiazol-2-yl)-acetamide and ammonium thiocyanate. The structures of compounds have been determined by 1H, 13C NMR, IR and X-ray analysis. In vitro anticancer activity of the synthesized compounds was tested by the National Cancer Institute and two (6, 16) of them has revealed the anticancer activity on leukemia, melanoma

  已经进行了几种具有苯并噻唑部分的新颖的4-噻唑烷酮的抗肿瘤筛选。（苯并噻唑-2-基）肼与三硫代羰基二乙醇酸或6-甲基-2-氨基苯并噻唑与2-乙氧基甲硫基-2-噻唑啉-4-酮的反应产生了起始的3-（1）或2-取代的（11）4这已经在Knoevenagel缩合随后被用于获取一系列5-亚芳基衍生物的-thiazolidinones 2-10，12-16。或者，根据2-氯-N-（6-甲基苯并噻唑-2-基）-乙酰胺与硫氰酸铵的反应，通过反合成方法得到化合物11。化合物的结构由1 H确定，13 C NMR，IR和X射线分析。体外合成的化合物的抗癌活性是由美国国家癌症研究所和两个（测试6，16）的他们已经揭示于白血病，黑色素瘤，肺癌，结肠癌，中枢神经系统癌，卵巢癌，肾癌，前列腺癌和乳腺癌细胞系中的抗癌活性。在测试的化合物中，2- 2- [3-（苯并噻唑-2-基氨基）-4-氧代-2-硫代噻唑烷啶-5-亚甲基甲基]
• Spiro-thiazolones
  申请人：Hoffmann-La Roche Inc.

  公开号：US10092551B2

  公开（公告）日：2018-10-09

  Spiro-thiazolones of formula I wherein X1, X2, X3, X4, R2, R3, R4, R5, R6 and R7 are as defined herein, which act as V1a receptor modulators, and in particular as V1a receptor antagonists, their manufacture, pharmaceutical compositions containing them and their use as medicaments for treatment of inappropriate secretion of vasopressin, anxiety, depressive disorders, obsessive compulsive disorder, autistic spectrum disorders, schizophrenia, aggressive behavior and phase shift sleep disorders, in particular jetlag.

  式 I 的螺噻唑啉酮 其中 X1、X2、X3、X4、R2、R3、R4、R5、R6 和 R7 如本文所定义，它们可作为 V1a 受体调节剂，尤其是 V1a 受体拮抗剂，其制造方法、含有它们的药物组合物以及它们作为药物的用途可用于治疗血管加压素分泌不当、焦虑症、抑郁症、强迫症、自闭症谱系障碍、精神分裂症、攻击行为和相移睡眠障碍，尤其是时差。
• Synthesis and Anticancer Activity of Novel Nonfused Bicyclic Thiazolidinone Derivatives
  作者：Dmytro Havrylyuk、Borys Zimenkovsky、Roman Lesyk

  DOI：10.1080/10426500802247563

  日期：2009.3.10

  A series of new 2-4-oxo-2-[(4-oxothiazolidin-2-ylidene)-hydrazono]-thiazolidin-5-yl}-N-arylacetamides (4a-e), 5-(2-oxo-2-aryl-ethyl)-2-[(4-oxothiazolidin-2-ylidene)-hydrazono]-thiazolidine-4-ones (5a-d), 2-(4-oxo-2-[(2-oxothiazolidin-4-ylidene)-hydrazono]-thiazolidin-5-yl)-N-arylacetamides (7a-e), and 5-(2-oxo-2-aryl-ethyl)-2-[(2-oxothiazolidin-4-ylidene)-hydrazono]-thiazolidine-4-ones (8a-d) have been synthesized starting from 2-thioxothiazolidin-4-one and 4-thioxothiazolidin-2-one through a multistep reaction sequence. 2-Thioxothiazolidin-4-one was alkylated via the intermediate formation of the triethylammonium salt 1 by ethyl chloroacetate. Compound 2 and 4-thioxothiazolidin-2-one reacted with thiosemicarbazides to give the 1-(4-thiazolidinone-2-ylidene)-4-R-thiosemicarbazones (3a,b) and 1-(2-thiazolidinone-4-ylidene)thiosemicarbazones (6a,b), respectively. Following [2+3]-cyclization of thiazolidinone-substituted thiosemicarbazones (3a,b and 6a,b) with N-arylmaleimides and aroylacrylic acids as equivalents of dielectrophilic synthon [C2]2 +, novel non-fused bicyclic thiazolidinones (4a-e, 5a-d, 7a-e, 8a-d) were synthesized. The structures of the new compounds (4a-e, 5a-d, 7a-e, 8a-d) were established on the basis of their elemental analysis and 1H NMR and mass spectral data. Eight of the synthesized compounds were tested, and three of them displayed different levels of antitumor activity. The most efficient antitumor agent2-4-oxo-3-furylmethyl-2-[(4-oxothiazolidin-2-ylidene)-hydrazono]-thiazolidin-5-yl}-N-4-chlorophenylacetamide (4d) was found to be active against leukemia, melanoma, lung, colon, CNS, ovarian, renal, prostate, and breast cancer cell lines with mean lgGI50 and lgTGI values of -5.35 and -4.78, respectively.