5-(4-bromo-phenyl)-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid ethyl ester | 1396008-08-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-bromo-phenyl)-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid ethyl ester
• 英文别名: ethyl 5-(4-bromophenyl)-3-methyltriazole-4-carboxylate
• CAS: 1396008-08-4
• 化学式: C₁₂H₁₂BrN₃O₂
• 分子量: 310.15
• InChiKey: UCBHZJMOYBDSHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-bromo-phenyl)-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid ethyl ester 在 叠氮磷酸二苯酯 、 水 、 三乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 5.0h， 生成 [5-(4-bromo-phenyl)-3-methyl-3H-[1,2,3]triazol-4-yl]carbamic acid (R)-1-phenyl-ethyl ester
  参考文献：
  名称：

  [EN] N-ALKYLTRIAZOLE COMPOUNDS AS LPAR ANTAGONISTS
  [FR] COMPOSÉS N-ALKYLTRIAZOLE UTILISÉS COMME ANTAGONISTES DE LPAR

  摘要：

  本文提供了式(I)的化合物，以及其药学上可接受的盐，其中取代基如规范中所披露的那样。这些化合物及含有它们的药物组合物对于治疗炎症性疾病和紊乱，例如肺纤维化等，是有用的...

  公开号：

  WO2013189864A1
• 作为产物：
  描述：

  (4-溴苯基)乙炔 在 四丁基氟化铵 、 水 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 6.67h， 生成 5-(4-bromo-phenyl)-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  [EN] N-ALKYLTRIAZOLE COMPOUNDS AS LPAR ANTAGONISTS
  [FR] COMPOSÉS N-ALKYLTRIAZOLE UTILISÉS COMME ANTAGONISTES DE LPAR

  摘要：

  本文提供了式(I)的化合物，以及其药学上可接受的盐，其中取代基如规范中所披露的那样。这些化合物及含有它们的药物组合物对于治疗炎症性疾病和紊乱，例如肺纤维化等，是有用的...

  公开号：

  WO2013189864A1

文献信息

• [EN] LYSOPHOSPHATIDIC ACID RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DES RÉCEPTEURS D'ACIDE LYSOPHOSPHATIDIQUE
  申请人：INTERMUNE INC

  公开号：WO2013025733A1

  公开（公告）日：2013-02-21

  Compounds, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds to treat, prevent or diagnose diseases, disorders, or conditions associated with one or more of the lysophosphatidic acid receptors are provided.

  提供了化合物、制备这种化合物的方法、包含这种化合物的药物组合物和药物，以及使用这种化合物治疗、预防或诊断与一种或多种赖氨酸磷脂酸受体相关的疾病、紊乱或状况的方法。
• N-ALKYLTRIAZOLE COMPOUNDS AS LPAR ANTAGONISTS
  申请人：Hoffmann-La Roche Inc.

  公开号：US20150133511A1

  公开（公告）日：2015-05-14

  Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of inflammatory diseases and disorders such as, for example, pulmonary fibrosis . . . .

  本文提供的化合物属于公式(I)：以及其药学上可接受的盐，其中取代基如规范中所披露的那样。这些化合物及其含有它们的药物组合物对于治疗炎症性疾病和疾病非常有用，例如肺纤维化。
• N-alkyltriazole compounds as LPAR antagonists
  申请人：Hoffmann-La Roche Inc.

  公开号：US09321738B2

  公开（公告）日：2016-04-26

  Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of inflammatory diseases and disorders such as, for example, pulmonary fibrosis.

  本文提供了式(I)的化合物，以及其药学上可接受的盐，其中取代基如规范中所披露。这些化合物及其含有它们的制药组合物，对于治疗炎症性疾病和疾患，如肺纤维化等，具有有用的作用。
• Discovery of Highly Selective and Orally Active Lysophosphatidic Acid Receptor-1 Antagonists with Potent Activity on Human Lung Fibroblasts
  作者：Yimin Qian、Matthew Hamilton、Achyutharao Sidduri、Stephen Gabriel、Yonglin Ren、Ruoqi Peng、Rama Kondru、Arjun Narayanan、Terry Truitt、Rachid Hamid、Yun Chen、Lin Zhang、Adrian J. Fretland、Ruben Alvarez Sanchez、Kung-Ching Chang、Matthew Lucas、Ryan C. Schoenfeld、Dramane Laine、Maria E. Fuentes、Christopher S. Stevenson、David C. Budd

  DOI：10.1021/jm301022v

  日期：2012.9.13

  Lysophosphatidic acid is a class of bioactive phospholipid that mediates most of its biological effects through LPA receptors, of which six isoforms have been identified. The recent results from LPA1 knockout mice suggested that blocking LPA1 signaling could provide a potential novel approach for the treatment of idiopathic pulmonary fibrosis. Here, we report the design and synthesis of pyrazole- and triazole-derived carbamates as LPA1-selective and LPA1/3 dual antagonists. In particular, compound 2, the most selective LPA1 antagonist reported, inhibited proliferation and contraction of normal human lung fibroblasts (NHLF) following LPA stimulation. Oral dosing of compound 2 to mice resulted in a dose-dependent reduction of plasma histamine levels in a murine LPA challenge model. Furthermore, we applied our novel antagonists as chemistry probes and investigated the contribution of LPA1/2/3 in mediating the pro-fibrotic responses. Our results suggest LPA1 as the major receptor subtype mediating LPA-induced proliferation and contraction of NHLF.
• LYSOPHOSPHATIDIC ACID RECEPTOR ANTAGONISTS
  申请人：Buckman Brad O.

  公开号：US20130072449A1

  公开（公告）日：2013-03-21

  Compounds, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds to treat, prevent or diagnose diseases, disorders, or conditions associated with one or more of the lysophosphatidic acid receptors are provided.