5-[4-(4-ethoxycarbonylmethyl-cyclohexyl)phenyl]-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid benzyl ester | 1396008-31-3

• 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-(4-ethoxycarbonylmethyl-cyclohexyl)phenyl]-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid benzyl ester
• 英文别名: 5-[4-(4-ethoxycarbonylmethyl-cyclohexyl)-phenyl]-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid benzyl ester；benzyl 5-[4-[4-(2-ethoxy-2-oxoethyl)cyclohexyl]phenyl]-3-methyltriazole-4-carboxylate
• CAS: 1396008-31-3
• 化学式: C₂₇H₃₁N₃O₄
• 分子量: 461.561
• InChiKey: YPPQKNCVNHOBGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  83.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-[4-(4-ethoxycarbonylmethyl-cyclohexyl)phenyl]-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid benzyl ester 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 15.0h， 以97.5%的产率得到5-[4-(4-ethoxycarbonylmethyl-cyclohexyl)phenyl]-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid
  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：

  2-(4-羟基环己基)乙酸乙酯 在 咪唑 、 三甲基氯硅烷 、 碘 、 1,2-二溴乙烷 、 三苯基膦 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 23.0h， 生成 5-[4-(4-ethoxycarbonylmethyl-cyclohexyl)phenyl]-3-methyl-3H-[1,2,3]triazole-4-carboxylic acid benzyl 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] N-ALKYLTRIAZOLE COMPOUNDS AS LPAR ANTAGONISTS<br/>[FR] COMPOSÉS N-ALKYLTRIAZOLE UTILISÉS COMME ANTAGONISTES DE LPAR
  申请人：HOFFMANN LA ROCHE

  公开号：WO2013189864A1

  公开（公告）日：2013-12-27

  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...
• 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。
• US9321738B2
  申请人：——

  公开号：US9321738B2

  公开（公告）日：2016-04-26
• 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.