4-(4,5,6,7-tetrahydro-1H-indazol-3-yl)benzoic acid methyl ester | 1001084-40-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(4,5,6,7-tetrahydro-1H-indazol-3-yl)benzoic acid methyl ester
• 英文别名: methyl 4-(4,5,6,7-tetrahydro-1H-indazol-3-yl)benzoate
• CAS: 1001084-40-7
• 化学式: C₁₅H₁₆N₂O₂
• 分子量: 256.304
• InChiKey: RVFHLGWCWVKHPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.74
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  54.98
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(4,5,6,7-tetrahydro-1H-indazol-3-yl)benzoic acid methyl ester 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.5h， 生成 4-[1-(2,6-dichlorobenzoyl)-4,5,6,7-tetrahydro-1H-indazol-3-yl]benzoic acid sodium salt
  参考文献：
  名称：

  縮合二環式ヘテロ環誘導体

  摘要：

  提供具有优良的视黄醇酸受体相关孤儿受体γt抑制作用，并且作为银屑病等治疗药物有用的化合物。通式（Ｉ）表示的化合物或其药理上可接受的盐。【环Ａ为吡咯环、咪唑环或吡唑环；环Ｂ为取代/非取代的苯环、环己二烯环、环戊二烯环、环己烯环等；Ｒ₁为Ｈ、卤原子等；Ｒ₂为Ｈ、卤原子、Ｃ₁−Ｃ₆烷基等；基＝Ｑ−Ｔ−表示的基为基＝ＣＨ−ＣＨ＝ＣＨ−等；Ｚ为基＝ＣＨ−等；基表示为式−Ｕ−Ｖ（ＣＯ₂Ｈ）−Ｗ−的基为，基表示为式−ＣＨ＝ＣＨ−Ｃ（ＣＯ₂Ｈ）＝ＣＨ−等】【选择图】无

  公开号：

  JP2016141632A
• 作为产物：
  描述：

  对苯二甲酸单甲酯 在 草酰氯 、 一水合肼 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.83h， 生成 4-(4,5,6,7-tetrahydro-1H-indazol-3-yl)benzoic acid methyl ester
  参考文献：
  名称：

  縮合二環式ヘテロ環誘導体

  摘要：

  提供具有优良的视黄醇酸受体相关孤儿受体γt抑制作用，并且作为银屑病等治疗药物有用的化合物。通式（Ｉ）表示的化合物或其药理上可接受的盐。【环Ａ为吡咯环、咪唑环或吡唑环；环Ｂ为取代/非取代的苯环、环己二烯环、环戊二烯环、环己烯环等；Ｒ₁为Ｈ、卤原子等；Ｒ₂为Ｈ、卤原子、Ｃ₁−Ｃ₆烷基等；基＝Ｑ−Ｔ−表示的基为基＝ＣＨ−ＣＨ＝ＣＨ−等；Ｚ为基＝ＣＨ−等；基表示为式−Ｕ−Ｖ（ＣＯ₂Ｈ）−Ｗ−的基为，基表示为式−ＣＨ＝ＣＨ−Ｃ（ＣＯ₂Ｈ）＝ＣＨ−等】【选择图】无

  公开号：

  JP2016141632A

文献信息

• Synthesis and antiplatelet activity of ethyl 4-(1-benzyl-1H-indazol-3-yl)benzoate (YD-3) derivatives
  作者：Hua-Sin Chen、Sheng-Chu Kuo、Che-Ming Teng、Fang-Yu Lee、Jih-Pyang Wang、Yu-Chun Lee、Chiung-Wen Kuo、Ching-Che Huang、Chin-Chung Wu、Li-Jiau Huang

  DOI：10.1016/j.bmc.2007.10.070

  日期：2008.2.1

  Previously, ethyl 4-(1-benzyl-1H-indazol-3-yl)benzoate (YD-3) was identified by us as the first non-peptide protease-activated receptor 4 (PAR4) antagonist. To continue on our development of novel anti-PAR4 agents, YD-3 was used as a lead compound and a series of its derivatives were synthesized and evaluated for their selective anti-PAR4 activity. Through structure-activity relationship (SAR) study, we identified the important functional groups contributing to anti-PAR4 activity, and these functional groups were kept intact during subsequent structural modification. Several new compounds with anti-PAR4 activity comparable to YD-3 were identified. Among them, ethyl 4-[1-(3-chlorobenzyl)-1H-indazol-3-yl]benzoate (33) showed the most potent inhibitory effect on PAR4-mediated platelet aggregation, ATP release, and P-selectin expression. On the other hand, ethyl 4-(1-phenyl-1H-indazol-3-yl)benzoate (83) exhibited dual inhibitory effects on PAR4 and thromboxane formation from arachidonic acid. The above findings can be used as guidelines for development of novel antiplatelet drug candidates. (c) 2008 Published by Elsevier Ltd.
• Microwave-assisted synthesis of N-2-benzyl-3-(4-ethoxycarbonylphenyl)indazole derivatives
  作者：H CHEN、L HUANG、F WONG、F LEE、C TENG、S KUO

  DOI：10.1016/s0385-5414(07)81204-4

  日期：2007.12.1

  The microwave-assisted synthesis for promoting N-2 substituted indazoles as the major products were successfully developed by treating 3-(4-ethoxycarbonylphenyl)indazoles with various substituted benzyl chloride (benzyl, o-chlorobenzyl, m-chlorobenzyl, and p-chlorobenzyl chloride) in the presence of two equivalents of triethylamine. The result was better than two trandional methods including the directly substitution with benzyl chloride and Mitsunobu reaction with benzyl alcohol.