methyl 4-nitro-1-(2-phenylethyl)-1H-pyrazole-3-carboxylate | 1021498-05-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 4-nitro-1-(2-phenylethyl)-1H-pyrazole-3-carboxylate
• 英文别名: 4-nitro-1-phenethyl-1H-pyrazole-3-carboxylic acid methyl ester；Methyl 4-nitro-1-phenethyl-1H-pyrazole-3-carboxylate；methyl 4-nitro-1-(2-phenylethyl)pyrazole-3-carboxylate
• CAS: 1021498-05-4
• 化学式: C₁₃H₁₃N₃O₄
• 分子量: 275.264
• InChiKey: CJIZHMRAXVRTNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  89.9
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2933199090

反应信息

• 作为反应物：
  描述：

  methyl 4-nitro-1-(2-phenylethyl)-1H-pyrazole-3-carboxylate 在 palladium 10% on activated carbon 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 25.0h， 生成 4-[2-(3,4-dimethyl-phenylsulfanyl)-acetylamino]-1-phenethyl-1H-pyrazole-3-carboxylic acid methyl ester
  参考文献：
  名称：

  WO2008/51047

  摘要：

  公开号：
• 作为产物：
  描述：

  methyl 4-nitro-1H-pyrazole-3-carboxylate hydrochloride 、 乙基溴苯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以69%的产率得到methyl 4-nitro-1-(2-phenylethyl)-1H-pyrazole-3-carboxylate
  参考文献：
  名称：

  [EN] NOVEL PYRAZOLODIAZEPINE COMPOUNDS AS A TRANSGLUTAMINASE INHIBITOR, THE PREPARATION METHOD THEREOF AND A COMPOSITION CONTAINING THE SAME
  [FR] NOUVEAUX COMPOSÉS DE PYRAZOLODIAZÉPINE EN TANT QU'INHIBITEUR DE LA TRANSGLUTAMINASE, PROCÉDÉ DE PRÉPARATION ASSOCIÉ ET COMPOSITION LES CONTENANT

  摘要：

  公开号：

  WO2010074480A3

文献信息

• AMINOPYRAZOLE DERIVATIVES, PROCESS FOR THE PREPARATION THEREOF, AND COMPOSITION FOR PREVENTING OR TREATING ISCHEMIC DISEASES CONTAINING THE SAME
  申请人：JUNG Yong-Sam

  公开号：US20100063106A1

  公开（公告）日：2010-03-11

  Provided are aminopyrazole derivatives, a process for the preparation thereof, and a composition for preventing or treating an ischemic disease containing the same. Since the aminopyrazole derivatives of the present invention can reduce an ischemic cell death significantly, they can be effectively used for the prevention and treatment of ischemic diseases mediated by ischemic cell death, or protection of organs.

  提供了氨基吡唑衍生物，其制备方法，以及含有该衍生物的用于预防或治疗缺血性疾病的组合物。由于本发明的氨基吡唑衍生物可以显著减少缺血细胞死亡，因此它们可以有效用于预防和治疗由缺血细胞死亡介导的缺血性疾病，或保护器官。
• Aminopyrazole derivatives, process for the preparation thereof, and composition for preventing or treating ischemic diseases containing the same
  申请人：Korea Research Institute of Chemical Technology

  公开号：US07939550B2

  公开（公告）日：2011-05-10

  Provided are aminopyrazole derivatives, a process for the preparation thereof, and a composition for preventing or treating an ischemic disease containing the same. Since the aminopyrazole derivatives of the present invention can reduce an ischemic cell death significantly, they can be effectively used for the prevention and treatment of ischemic diseases mediated by ischemic cell death, or protection of organs.

  本发明提供了氨基吡唑衍生物及其制备方法和用于预防或治疗缺血性疾病的组合物。由于本发明的氨基吡唑衍生物可以显著减少缺血性细胞死亡，因此它们可以有效地用于预防和治疗由缺血性细胞死亡介导的缺血性疾病，或保护器官。
• The discovery of inhibitors of Fas-mediated cell death pathway using the combined computational method
  作者：Seo Hee Jung、Ji Hee Suh、Eun Hee Kim、Jun Tae Kim、Seung-Eun Yoo、Nam Sook Kang

  DOI：10.1016/j.bmcl.2013.07.018

  日期：2013.9

  In this study, pharmacophore and 3D-QSAR models were developed for analogues of 3-substituted-benzofuran-2-carboxylate as inhibitors of Fas-mediated cell death pathways. Our pharmacophore model has good correspondence with experimental results and can explain the variance in biological activities coherently with respect to the structure of the data set compounds. The predictive power for our synthesized compounds were 0.96 for the pharmacophore model, 0.58 for the comparative molecular field analysis (CoMFA) model, and 0.57 for the comparative molecular similarity analysis (CoMSIA) model. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.
• Synthesis and structure–activity relationships of pyrazolodiazepine derivatives as human P2X7 receptor antagonists
  作者：Ju-Yeon Lee、Juan Yu、Won Je Cho、Hyojin Ko、Yong-Chul Kim

  DOI：10.1016/j.bmcl.2009.09.053

  日期：2009.11

  Screening of library compounds has yielded pyrazolodiazepine derivatives with P2X(7) receptor antagonist activity. To explore the structure -activity relationships (SAR) of these pyrazolodiazepines as human P2X(7) receptor antagonists, derivatives were synthesized by substitutions at positions R-2 and R-3 of the pyrazolodiazepine skeleton. Using a 2'(3')-O-(4-benzoylbenzoyl)ATP (BzATP)-induced fluorescent ethidium uptake assay, the activities of these derivatives were tested in HEK-293 cells stably expressing human P2X(7) receptors. Moreover, the effect of these derivatives was assessed by measuring their effect on IL-1 beta release induced by BzATP-induced activation of differentiated THP-1 cells. A 2-phenethyl pyrazolodiazepine derivative with a 1-methyl-1H-3-indolyl group at position R-2 had fivefold greater activity than the derivative with a 5-isoquinolinyl at R-2. Moreover, a benzyl moiety at R-3 had fivefold greater activity than a bicyclic moiety. The stereochemical effect at C-6 showed a preference for the (R)-isomer. Among the series of active derivatives, compound 23b, with a phenethyl group at R-1, a 3-methyl indole at R-2, and a benzyl at R-3, exhibited activity similar to that of the positive control, KN-62, as shown by the inhibitory effects of IL-1 beta release. (C) 2009 Elsevier Ltd. All rights reserved.
• Discovery and structure–activity relationships of pyrazolodiazepine derivatives as the first small molecule agonists of the Drosophila sex peptide receptor
  作者：Joeng-hyun Kim、Pyeong-hwa Jeong、Ju-Yeon Lee、Jae-hyuk Lee、Young-Joon Kim、Yong-Chul Kim

  DOI：10.1016/j.bmc.2015.02.035

  日期：2015.4

  In behavioral research, the sex peptide receptor in Drosophila melanogaster (DrmSPR) is the most interesting G protein-coupled receptor (GPCR) and is involved in post-mating responses such as increased egg-laying and decreased receptivity of the female; during these responses, the receptors are activated by a specific natural peptide agonist (sex peptide, SP). To discover small molecule agonists for DrmSPR, a compound library based on a pyrazolodiazepine scaffold, which was previously reported as a potential privileged structure, was screened. Structure-activity relationship (SAR) studies of the hit compounds, which exhibited weak agonistic effects (69-72% activation at 100 mu M), were explored through the synthesis of various analogs with substituents at the R-1, R-2, R-3 and R-4 positions of the pyrazolodiazepine skeleton. As a result, compounds 21 and 31 of the 6-benzyl pyrazolodiazepine derivative series were found to be small molecule agonists for DrmSPR with EC50 values of 3-4 mu M. (C) 2015 Elsevier Ltd. All rights reserved.