ethyl 2-[4-(1,1-dimethylethyl)phenyl]-4-methyl-1,3-thiazole-5-carboxylate | 343322-53-2

• 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: ethyl 2-[4-(1,1-dimethylethyl)phenyl]-4-methyl-1,3-thiazole-5-carboxylate
• 英文别名: ethyl 2-(4-(tert-butyl)phenyl)-4-methylthiazole-5-carboxylate；2-(4-tert-butyl-phenyl)-4-methyl-thiazole-5-carboxylic acid ethyl ester；ethyl 2-(4-tert-butylphenyl)-4-methyl-1,3-thiazole-5-carboxylate
• CAS: 343322-53-2
• 化学式: C₁₇H₂₁NO₂S
• 分子量: 303.425
• InChiKey: GKNQMOJEPINFRF-UHFFFAOYSA-N

物化性质

• 沸点：
  408.6±47.0 °C(Predicted)
• 密度：
  1.104±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 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-[4-(1,1-dimethylethyl)phenyl]-4-methyl-1,3-thiazole-5-carboxylate 在 potassium carbonate 、 一水合肼 、 间氯过氧苯甲酸 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 5-(2-(4-(tert-butyl)phenyl)-4-methylthiazol-5-yl)-N-cyclohexyl-1,3,4-oxadiazol-2-amine
  参考文献：
  名称：

  具有恶二唑接头的叔丁基苯基噻唑：一类具有抗生物膜活性的新型口服生物可利用抗生素†

  摘要：

  对具有恶二唑接头的新型叔丁基苯基噻唑系列的结构-活性和结构-动力学关系进行了研究，目的是获得一种新的口服抗菌化合物。制备、纯化和鉴定了 22 种新化合物。检查了它们对耐甲氧西林金黄色葡萄球菌的活性。具有 3-羟基氮杂环丁烷作为含氮侧链的化合物20对 24 种临床分离株显示出有希望的活性，包括对万古霉素耐药的葡萄球菌和肠球菌，MIC 值范围为 4-8 μg mL -1. 该化合物的其他优点包括以剂量依赖性方式根除葡萄球菌生物膜团块的能力，以及在口服剂量 25 mg kg -1后具有高代谢稳定性，生物半衰期超过 5 小时和血浆浓度。C max ) 超过 MIC 值。

  DOI：

  10.1039/c8ra10525a
• 作为产物：
  描述：

  4-叔丁基苯甲酰胺 在 tetraphosphorus decasulfide 、 碳酸氢钠 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 25.0h， 生成 ethyl 2-[4-(1,1-dimethylethyl)phenyl]-4-methyl-1,3-thiazole-5-carboxylate
  参考文献：
  名称：

  Substituted 2-[(4-Aminomethyl)phenoxy]-2-methylpropionic Acid PPARα Agonists. 1. Discovery of a Novel Series of Potent HDLc Raising Agents

  摘要：

  The peroxisome proliferator activated receptors PPAR alpha, PPAR gamma, and PPAR delta are ligand-activated transcription factors that play a key role in lipid homeostasis. The fibrates raise circulating levels of high-density lipoprotein cholesterol and lower levels of triglycerides in part through their activity as PPAR alpha agonists; however, the low potency and restricted selectivity of the fibrates may limit their efficacy, and it would be desirable to develop more potent and selective PPAR alpha agonists. Modification of the selective PPAR delta agonist 1 (GW501516) so as to incorporate the 2-aryl-2-methylpropionic acid group of the fibrates led to a marked shift in potency and selectivity toward PPAR alpha agonism. Optimization of the series gave 25a, which shows EC50 = 4 nM on PPAR alpha and at least 500-fold selectivity versus PPAR delta and PPAR gamma. Compound 25a (GW590735) has been progressed to clinical trials for the treatment of diseases of lipid imbalance.

  DOI：

  10.1021/jm058056x

文献信息

• [EN] NOVEL 2-ARYLTHIAZOLE COMPOUNDS AS PPARALPHA AND PPARGAMA AGONISTS<br/>[FR] NOUVEAUX COMPOSES 2-ARYLTHIAZOLE UTILISES COMME AGONISTES DES RECEPTEURS PPARALPHA ET PPARGAMMA
  申请人：HOFFMANN LA ROCHE

  公开号：WO2004020420A1

  公开（公告）日：2004-03-11

  The present invention relates to compounds of formula (I) wherein Rl to R10, X, Y and n are as defined in the description and claims, and pharmaceutically acceptable salts and esters thereof. The compounds are useful for the treatment of diseases such as diabetes.

  本发明涉及式(I)的化合物，其中R1至R10、X、Y和n如描述和权利要求中所定义，并且其药学上可接受的盐和酯。这些化合物对于治疗疾病如糖尿病是有用的。
• Thiazole derivatives
  申请人：——

  公开号：US20040110807A1

  公开（公告）日：2004-06-10

  The present invention provides compounds of formula (I) 1 wherein R 1 to R 10 , X, Y and n are indicated in the specification, and pharmaceutically acceptable salts and esters thereof. The compounds are useful for the treatment of non-insulin dependent diabetes mellitus.

  本发明提供了式(I)1的化合物，其中R1至R10、X、Y和n在规范中指定，并且其药学上可接受的盐和酯。该化合物可用于治疗非胰岛素依赖型糖尿病。
• Oxadiazolylthiazoles as novel and selective antifungal agents
  作者：Mohamed Hagras、Ehab A. Salama、Ahmed M. Sayed、Nader S. Abutaleb、Ahmed Kotb、Mohamed N. Seleem、Abdelrahman S. Mayhoub

  DOI：10.1016/j.ejmech.2020.112046

  日期：2020.3

  Studying the structure-activity relationships (SAR) of oxadiazolylthiazole antibiotics unexpectedly led us to identify ethylenediamine- and propylenediamine-analogs as potential antimycotic novel lead structures. Replacement of the ethylenediamine moiety for the lead compound 7 with cis-diaminocyclohexyl group (compound 18) significantly enhanced the antifungal activity. In addition to the high safety margin of 18 against mammalian cells, it showed highly selective broad-spectrum activity against fungal cells without inhibiting the human normal microbiota. The antifungal activity of 18 was investigated against 20 drug-resistant clinically important fungi, including Candida species, Cryptococcus, and Aspergillus fumigatus strains. In addition to the low MIC values that mostly ranged between 0.125 and 2.0 mu g/mL, compound 18 outperformed fluconazole in disrupting mature Candida biofilm. (C) 2020 Elsevier Masson SAS. All rights reserved.
• NOVEL 2-ARYLTHIAZOLE COMPOUNDS AS PPARALPHA AND PPARGAMMA AGONISTS
  申请人：F.HOFFMANN-LA ROCHE AG

  公开号：EP1537091A1

  公开（公告）日：2005-06-08
• US6809110B2
  申请人：——

  公开号：US6809110B2

  公开（公告）日：2004-10-26