methyl 4-(1H-indazol-3-yl)benzoate | 1001084-41-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 4-(1H-indazol-3-yl)benzoate
• CAS: 1001084-41-8
• 化学式: C₁₅H₁₂N₂O₂
• 分子量: 252.272
• InChiKey: IQWNSOIWTZPSLO-UHFFFAOYSA-N

物化性质

• 沸点：
  468.2±28.0 °C(Predicted)
• 密度：
  1.272±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-(1H-indazol-3-yl)benzoate 在 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 16.0h， 生成 4-(1H-indazol-3-yl)benzoic acid
  参考文献：
  名称：

  WO2020198478A5

  摘要：

  公开号：

  WO2020198478A5
• 作为产物：
  描述：

  4-(4,5,6,7-tetrahydro-1H-indazol-3-yl)benzoic acid methyl ester 在 palladium on activated charcoal 作用下， 以 萘烷 为溶剂， 反应 24.0h， 以82.7%的产率得到methyl 4-(1H-indazol-3-yl)benzoate
  参考文献：
  名称：

  Synthesis and antiplatelet activity of ethyl 4-(1-benzyl-1H-indazol-3-yl)benzoate (YD-3) derivatives

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2007.10.070

文献信息

• [EN] BI-DENTATE COMPOUNDS AS KINASE INHIBITORS<br/>[FR] COMPOSÉS BIDENTATE EN TANT QU'INHIBITEURS DE KINASE
  申请人：BURNHAM INST MEDICAL RESEARCH

  公开号：WO2009018490A1

  公开（公告）日：2009-02-05

  The present invention provides compound having the general structure A or pharmaceutically acceptable salts thereof: Het-L-P (A) wherein Het is an aromatic moiety comprising a heterocyclic structure mimicking ATP, P is a docking site derived peptide or a docking site peptide mimetic, and L is a linking moiety, wherein L links the ATP mimetic to the docking site peptide moiety. The compounds having the general structure A can serve as inhibitors of kinases, such as the kinases JNK, Erk and P38.

  本发明提供了具有一般结构A或其药学上可接受的盐的化合物：Het-L-P（A），其中Het是包含模拟ATP的杂环结构的芳香基团，P是源自肽的结合位点或模拟结合位点的肽，L是连接基团，其中L将ATP模拟物连接到结合位点肽基团。具有一般结构A的化合物可以作为激酶的抑制剂，例如激酶JNK、Erk和P38。
• Design, Synthesis and Anticandidal Evaluation of Indazole and Pyrazole Derivatives
  作者：Karen Rodríguez-Villar、Alicia Hernández-Campos、Lilián Yépez-Mulia、Teresita del Rosario Sainz-Espuñes、Olivia Soria-Arteche、Juan Francisco Palacios-Espinosa、Francisco Cortés-Benítez、Martha Leyte-Lugo、Bárbara Varela-Petrissans、Edgar A. Quintana-Salazar、Jaime Pérez-Villanueva

  DOI：10.3390/ph14030176

  日期：——

  a series of indazole and pyrazole derivatives were designed in this work, employing bioisosteric replacement, homologation, and molecular simplification as new anticandidal agents. Compounds were synthesized and evaluated against C. albicans, C. glabrata, and C. tropicalis strains. The series of 3-phenyl-1H-indazole moiety (10a–i) demonstrated to have the best broad anticandidal activity. Particularly

  由念珠菌属酵母引起的念珠菌病是浅表和粘膜感染的第二大原因，也是血液感染的第四大原因。尽管可获得一些治疗念珠菌病的抗真菌药物，但对当前疗法的耐药菌株正在出现。因此，寻找新的候选化合物无疑是当务之急。在这方面，在这项工作中设计了一系列吲唑和吡唑衍生物，采用生物等位取代，同源化和分子简化作为新的抗候选药物。合成化合物并针对白色念珠菌，光滑念珠菌和热带念珠菌菌株进行评估。3-苯基-1 H-吲唑部分系列（10a–i被证明具有最佳的广泛的抗候选活性。特别地，具有N，N-二乙基羧酰胺取代基的化合物10g对白色念珠菌和对咪康唑敏感的和抗性的光滑念珠菌物种最具活性。因此，3-苯基-1 H-吲唑支架代表了开发具有新化学型的新抗候选药物的机会。
• Rhodium‐Catalysed Selective C−H Allylation of 1<i>H</i>‐Indazoles with Vinylethylene Carbonate: Easily Introducing Allylic Alcohol
  作者：Xiang Zhao、Junwei Huang、Yadong Feng、Xiuling Cui

  DOI：10.1002/ejoc.202300823

  日期：2023.10.21

  An efficient rhodium(III)-catalyzed C−H bond activation/allylation reaction of 3-aryl-1H-indazoles with easily available vinylethylene carbonate has been reported. A series of allyl alcohol substituted 3-aryl-1H-indazoles were obtained.

  据报道，铑(III)催化的3-芳基-1H-吲唑与容易获得的乙烯基碳酸亚乙酯发生有效的CH键活化/烯丙基化反应。获得了一系列烯丙醇取代的3-芳基-1H-吲唑。
• WO2020198478A5
  申请人：——

  公开号：WO2020198478A5

  公开（公告）日：2022-10-25
• 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.