1-benzyl-3-(4'-hydroxymethylphenyl)indazole | 170632-51-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-benzyl-3-(4'-hydroxymethylphenyl)indazole
• 英文别名: 1-Benzyl-3-(p-hydroxymethylphenyl)indazole；[4-(1-benzyl-1H-indazol-3-yl)-phenyl]-methanol；[4-(1-benzylindazol-3-yl)phenyl]methanol
• CAS: 170632-51-6
• 化学式: C₂₁H₁₈N₂O
• 分子量: 314.387
• InChiKey: FUIFWIQDRYVTCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzyl-3-(4'-hydroxymethylphenyl)indazole 在 manganese(IV) oxide 作用下， 以 丙酮 为溶剂， 反应 20.0h， 以80.1%的产率得到4-(1-苄基-1H-吲唑-3-基)苯甲醛
  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
• 作为产物：
  描述：

  1-benzyl-3-(4'-ethoxycarbonylphenyl)indazole 在 calcium borohydride 作用下， 生成 1-benzyl-3-(4'-hydroxymethylphenyl)indazole
  参考文献：
  名称：

  Synthesis of 1-Benzyl-3-(5‘-hydroxymethyl-2‘-furyl)indazole Analogues as Novel Antiplatelet Agents

  摘要：

  1-Benzyl-3-(5'-hydroxymethyl-2'-furyl)indazole (28, YC-1) was selected as the lead compound for systemic structural modification. After screening for antiplatelet activity, SARs of YC-1 analogues were established. Among these potent active derivatives, compounds 29, 30, 31, 44, and 45 functioned as potent activators of sGC and inhibitors of PDE5 with potency comparable to that of YC-1. In addition, compound 58 was found to be a selective and potent inhibitor of protease-activated receptor type 4 (PAR4)-dependent platelet activation.

  DOI：

  10.1021/jm010001h

文献信息

• Novel fused pyrazolyl compound
  申请人：Kuo Sheng-Chu

  公开号：US20050215612A1

  公开（公告）日：2005-09-29

  A fused pyrazolyl compound of the following formula: wherein A, Ar 1 , Ar 2 , R 1 , R 2 , R 3 , and R 4 , are as defined herein. Also disclosed is a pharmaceutical composition containing an effective amount of the above-described fused pyrazolyl compound.

  一种具有下述通式的融合吡唑基化合物：其中A、Ar1、Ar2、R1、R2、R3和R4如本文所定义。还披露了一种含有上述融合吡唑基化合物有效量的药物组合物。
• Synthesis of indole analogs of 1-benzyl-3-(5'-hydroxymethy 1-2' -furyl) indazole (YC-1) as anti-platelet agents
  申请人：Kuo Sheng-Chu

  公开号：US20060106041A1

  公开（公告）日：2006-05-18

  The present invention synthesizes a series of novel indole analogs of 1-benzyl-3-(5′-hydroxymethyl-2′-furyl)indazole (YC-1), and their anti-platelet activity.

  本发明合成了一系列新型吲哚类似物，包括1-苄基-3-(5'-羟甲基-2'-呋喃基)吲哚唑（YC-1）及其抗血小板活性。
• Method of treating disorders related to protease-activated receptors-induced cell activation
  申请人：——

  公开号：US20020004518A1

  公开（公告）日：2002-01-10

  A method of treating a disorder related to cell activation induced by protease-activated receptors. The method includes administering to a subject in need thereof a compound having a pyrazolyl core; an aryl group, via an via an alkylene linker, bonded to 1-N of the pyrazolyl core; a second aryl group fused at 4-C and 5-C of the pyrazolyl core; and a third aryl group bonded directly to 3-C of the pyrazolyl core.

  一种治疗与蛋白酶激活受体引起的细胞活化相关障碍的方法。该方法包括向需要的受试者施用具有吡唑基核的化合物；通过烷基连接剂与吡唑基核的1-N键合的芳基团；在吡唑基核的4-C和5-C处融合的第二个芳基团；以及直接与吡唑基核的3-C键合的第三个芳基团。
• Blockade of voltage dependent sodium channels
  申请人：——

  公开号：US20030171403A1

  公开（公告）日：2003-09-11

  Compounds of formula (1), and pharmaceutically acceptable salts thereof, are capable of blockading voltage-dependent sodium channels and are useful in particular, in treating glaucoma and multiple sclerosis.

  式（1）的化合物及其药学上可接受的盐能够阻断电压依赖性钠通道，并且在治疗青光眼和多发性硬化症方面具有用处。
• Compounds, compositions and methods
  申请人：Park Jong-Wan

  公开号：US20050187276A1

  公开（公告）日：2005-08-25

  The present invention provides methods and pharmaceutical compositions for inhibiting expressions of HIF and HIF regulated genes, inhibiting angiogenesis, inducing cell cycle arrest in tumor cells, and treating cell proliferating diseases or conditions.

  本发明提供了一种抑制HIF和HIF调节基因表达、抑制血管生成、诱导肿瘤细胞细胞周期停滞和治疗细胞增殖性疾病或情况的方法和制药组合物。