ethyl 2-butyl-1,3-thiazole-4-carboxylate | 59936-89-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 2-butyl-1,3-thiazole-4-carboxylate
• 英文别名: 2-butyl-thiazole-4-carboxylic acid ethyl ester
• CAS: 59936-89-9
• 化学式: C₁₀H₁₅NO₂S
• 分子量: 213.301
• InChiKey: ICAKJYYIQMLRRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-butyl-1,3-thiazole-4-carboxylate 在 sodium hydroxide 作用下， 生成 2-butyl-thiazole-4-carboxylic acid
  参考文献：
  名称：

  Clemence; Le Martret; Fournex, European Journal of Medicinal Chemistry, 1976, vol. 11, # 6, p. 567 - 570

  摘要：

  DOI：
• 作为产物：
  描述：

  Tetra-O-benzoyl-aldehydo-D-arabinose 在 吡啶 、 三氯溴甲烷 、 palladium 10% on activated carbon 、 盐酸羟胺 、 氢气 、 sodium acetate 、 甲基磺酰氯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 79.0h， 生成 ethyl 2-[(3'S)-3',4'-bis(benzoyloxy)butyl]-1,3-thiazole-4-carboxylate 、 ethyl 2-butyl-1,3-thiazole-4-carboxylate
  参考文献：
  名称：

  2-Substituted thiazole-4-carboxamide derivatives as tiazofurin mimics: synthesis and in vitro antitumour activity

  摘要：

  Tiazofurin analogues bearing a 5-hydroxymethy1-2-methyl-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol moiety as a sugar mimic (2 and 3), and two novel thiazole-based acyclo-C-nucleosides 4 and 16 have been synthesized in multistep sequences starting from D-xylose (compounds 2 and 3) or from D-arabinose (compounds 4 and 16). All synthesized analogues showed potent in vitro antitumour activities against a panel of human tumour cell lines. Flow cytometry data suggest that cytotoxic effects of analogues 2-4 and 16 in the culture of 1(562 cells might be mediated by apoptosis. It was also found that these analogues induced changes in cell cycle distribution of 1(562 cells. Results of western blot analysis (upregulation of Bax and downregulation of Bc1-2, activation of caspase-3 and the presence of a PARP cleavage product) suggest that tiazofurin mimics (2-4 and 16) in 1(562 cells induced apoptosis in a caspasedependent way. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.02.035

文献信息

• Asymmetric synthesis of 2-alkyl-3-thiazoline carboxylates: stereochemistry of the MnO2-mediated oxidation of cis- and trans-2-alkyl-thiazolidine-(4R)-carboxylates
  作者：Xavier Fernandez、Elisabet Duñach

  DOI：10.1016/s0957-4166(01)00219-1

  日期：2001.6

  The asymmetric synthesis of a series of 3-thiazoline carboxylates, 2, was effected by MnO2 oxidation of the corresponding cis/trans thiazolidines, 1. The stereochemistry of the oxidation reaction was studied using NMR and chiral GC analyses. Compounds 2 were obtained with enantiomeric excesses (e.e.s) in the range of 40–100%.

  一系列3-噻唑啉羧酸盐2的不对称合成是通过MnO 2氧化相应的顺/反噻唑烷1来实现的。使用NMR和手性GC分析研究了氧化反应的立体化学。获得的化合物2的对映体过量（ee）在40-100％的范围内。
• Compounds
  申请人：Alcaraz Lilian

  公开号：US20090298807A1

  公开（公告）日：2009-12-03

  The present invention relates to spirocyclic amide derivatives of the formula I, pharmaceutically acceptable salts thereof, a process for their preparation, pharmaceutical compositions containing them, and their use in therapy.

  本发明涉及公式 I 的螺环酰胺衍生物，其药学上可接受的盐，其制备方法，含有它们的制药组合物以及它们在治疗中的应用。
• HETEROCYCLYL-SUBSTITUTED ANTI-HYPERCHOLESTEROLEMIC COMPOUNDS
  申请人：Morriello Gregori J.

  公开号：US20100069347A1

  公开（公告）日：2010-03-18

  This invention provides cholesterol absorption inhibitors of Formula I: and the pharmaceutically acceptable salts thereof, wherein R 12 is a hydroxylated alkyl group and R 9 contains a heterocyclic ring. The compounds are useful for lowering plasma cholesterol levels, particularly LDL cholesterol, and for treating atherosclerosis and preventing atherosclerotic disease events.

  本发明提供了I式胆固醇吸收抑制剂及其药学上可接受的盐，其中R12是一个羟基化的烷基基团，而R9包含一个杂环环。这些化合物对降低血浆胆固醇水平，特别是低密度脂蛋白胆固醇，以及治疗动脉粥样硬化和预防动脉粥样硬化疾病事件具有用处。
• Compouds
  申请人：Alcaraz Lilian

  公开号：US20120322788A1

  公开（公告）日：2012-12-20

  The present invention relates to spirocyclic amide derivatives of the formula I, pharmaceutically acceptable salts thereof, a process for their preparation, pharmaceutical compositions containing them, and their use in therapy.

  本发明涉及公式I的螺环酰胺衍生物，其药学上可接受的盐，其制备方法，含有它们的制药组合物以及它们在治疗中的用途。
• Chemo- and regioselective synthesis of alkyl-3-thiazoline carboxylates
  作者：Xavier Fernandez、Roland Fellous、Louisette Lizzani-Cuvelier、Michel Loiseau、Elisabet Duñach

  DOI：10.1016/s0040-4039(00)02321-2

  日期：2001.2

  The synthesis of a series of allyl substituted 3-thiazoline-carboxylates was carried out from the corresponding thiazolidines, by a MnO2-mediated oxidation reaction under mild conditions. The reaction was chemoselective towards the amine-imine oxidation and was also regioselective, affording the unsaturation at the 3-position of the heterocycle. (C) 2001 Published by Elsevier Science Ltd.