2-(4-氰基苯基)-4-甲基-1,3-噻唑-5-羧酸 | 187998-77-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-(4-氰基苯基)-4-甲基-1,3-噻唑-5-羧酸
• 中文别名: 5-噻唑羧酸,2-(4-氰基苯基)-4-甲基-
• 英文名称: 2-(4-cyano-phenyl)-4-methyl-thiazole-5-carboxylic acid
• 英文别名: 2-(4-cyanophenyl)-4-methyl-1,3-thiazole-5-carboxylic Acid
• CAS: 187998-77-2
• 化学式: C₁₂H₈N₂O₂S
• 分子量: 244.274
• InChiKey: WFRWISYYACTKRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2-(2,4-Difluorophenyl)-3-(N-methylamino)-1-(1H-1,2,4-triazol-1-yl)-2-butanol 、 2-(4-氰基苯基)-4-甲基-1,3-噻唑-5-羧酸 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 2-(4-cyanophenyl)-N-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1,2,4-triazol-1-yl)propyl]-N,4-dimethyl-thiazole-5-carboxamide
  参考文献：
  名称：

  New Azole Antifungals. 2. Synthesis and Antifungal Activity of Heterocyclecarboxamide Derivatives of 3-Amino-2-aryl-1-azolyl-2-butanol

  摘要：

  A series of 92 azole antifungals containing an amido alcohol unit was synthesized. The nature and substitution of the amide portion was systematically modified in search of improved antifungal activity, especially against filamentous fungi. The compounds were tested in vitro against a variety of clinically important pathogens and in vivo (po) in a murine candidosis model. Thiazole and thiophene carboxamides carrying both a substituted phenyl ring and a small alkyl. group were best suited for activity against filamentous fungi. In a subset of these compounds, the amide portion was conformationally locked by means of a pyrimidone ring and it was proven that only an orthogonal orientation of the phenyl ring yields bioactive products. A tendency to display long plasma elimination half-lives was observed in both series. Two compounds, 74 and 107, representative of the open and cyclic amides, respectively, were chosen for further studies, based on their excellent activity in in vivo murine models of candidosis and aspergillosis. This work describes the SARs found within this series. The next paper displays the results obtained in a related series of compounds, the quinazolinones.

  DOI：

  10.1021/jm970726e
• 作为产物：
  描述：

  2-(4-cyano-phenyl)-4-methyl-thiazole-5-carboxylic acid ethyl ester 在 lithium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以92%的产率得到2-(4-氰基苯基)-4-甲基-1,3-噻唑-5-羧酸
  参考文献：
  名称：

  [EN] ARYL PIPERIDINE DERIVATIVES AS INDUCERS OF LDL-RECEPTOR EXPRESSION FOR THE TREATMENT OF HYPERCHOLESTEROLEMIA
  [FR] DERIVES DE PIPERIDINE-ARYLE SERVANT D'INDUCTEURS DE L'EXPRESSION DU RECEPTEUR LDL POUR LE TRAITEMENT DE L'HYPERCHOLESTEROLEMIE

  摘要：

  这项发明涉及一种新型化合物，可以上调LDL受体（LDL-r）的表达，并涉及其制备过程、含有它们的药物组合物以及它们的医疗用途。更具体地，这项发明涉及式（I）的新型芳香基哌啶及其在治疗中的应用。

  公开号：

  WO2004006922A1

文献信息

• [EN] ARYL PIPERIDINE DERIVATIVES AS INDUCERS OF LDL-RECEPTOR EXPRESSION FOR THE TREATMENT OF HYPERCHOLESTEROLEMIA<br/>[FR] DERIVES DE PIPERIDINE-ARYLE SERVANT D'INDUCTEURS DE L'EXPRESSION DU RECEPTEUR LDL POUR LE TRAITEMENT DE L'HYPERCHOLESTEROLEMIE
  申请人：GLAXO GROUP LTD

  公开号：WO2004006922A1

  公开（公告）日：2004-01-22

  This invention relates to novel compounds which up-regulate LDL receptor (LDL-r) expression and to processes for their preparation, pharmaceutical compositions containing them and their medical use. More particularly, this invention relates to novel aromatic piperidines of formula (I) and their use in therapy.

  这项发明涉及一种新型化合物，可以上调LDL受体（LDL-r）的表达，并涉及其制备过程、含有它们的药物组合物以及它们的医疗用途。更具体地，这项发明涉及式（I）的新型芳香基哌啶及其在治疗中的应用。
• [EN] ARYL PIPERIDINE DERIVATIVES AND USE THEREOF TO REDUCE ELEVATED LEVELS OF LDL-CHOLESTEROL<br/>[FR] DERIVES D'ARYLE PIPERIDINE ET UTILISATION DE CEUX-CI POUR REDUIRE DES TAUX ELEVES DE LDL-CHOLESTEROL
  申请人：GLAXO GROUP LTD

  公开号：WO2004006924A1

  公开（公告）日：2004-01-22

  This invention relates to novel compounds which up-regulate LDL receptor (LDL-r) expression and to processes for their preparation, pharmaceutical compositions containing them and their medical use. More particularly, this invention relates to novel aromatic piperidines and their use in therapy.

  这项发明涉及一种新型化合物，可以上调LDL受体（LDL-r）的表达，并涉及其制备方法、含有它们的药物组合物以及它们的医疗用途。更具体地说，这项发明涉及新型芳香基哌啶类化合物及其在治疗中的应用。
• [EN] NOVEL COMPOUND, METHOD FOR PREPARATION THEREOF, AND ANTIFUNGAL COMPOSITION COMPRISING THE SAME<br/>[FR] NOUVEAU COMPOSÉ, PROCÉDÉ DE PRÉPARATION DE CELUI-CI, ET COMPOSITION ANTIFONGIQUE LE COMPRENANT
  申请人：DAE WOONG PHARMA

  公开号：WO2015069011A1

  公开（公告）日：2015-05-14

  Disclosed are a compound having an excellent antifungal activity, a composition containing the same, and its use for prevention and treatment of fungal infectious diseases.

  揭示了一种具有优异抗真菌活性的化合物，以及包含该化合物的组合物，以及其用于预防和治疗真菌感染性疾病的用途。
• Aryl piperidine derivatives and use thereof to reduce elevated levels of ldl-cholesterol
  申请人：Bouillot Marie Jeanne Anne

  公开号：US20060122432A1

  公开（公告）日：2006-06-08

  This invention relates to novel compounds which up-regulate LDL receptor (LDL-r) expression and to processes for their preparation, pharmaceutical compositions containing them and their medical use. More particularly, this invention relates to novel aromatic piperidines and their use in therapy.

  该发明涉及一种新型化合物，该化合物可上调低密度脂蛋白受体（LDL-r）表达，以及其制备过程、含有该化合物的药物组合物及其医疗用途。更具体地说，该发明涉及一种新型芳香环戊胺类化合物及其在治疗中的应用。
• Aryl piperidine derivatives as inducers of ldl-receptor expression for the treatment of hypercholesterolemia
  申请人：Bouillot Jeanne Anne Marie

  公开号：US20060052384A1

  公开（公告）日：2006-03-09

  This invention relates to novel compounds which up-regulate LDL receptor (LDL-r) expression and to processes for their preparation, pharmaceutical compositions containing them and their medical use. More particularly, this invention relates to novel aromatic piperidines and their use in therapy.

  本发明涉及一种新型化合物，其上调LDL受体（LDL-r）表达，并涉及其制备过程、含有它们的制药组合物及其医学用途。更具体地说，本发明涉及新型芳香基哌啶及其在治疗中的应用。