(R)-tert-butyl 4-(2-(6-benzyl-4-(cyclopropanecarbonyl)-8-oxo-5,6,7,8-tetrahydropyrazolo[4,3-e][1,4]diazepin-2(4H)-yl)ethyl)piperidine-1-carboxylate | 1166989-71-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (R)-tert-butyl 4-(2-(6-benzyl-4-(cyclopropanecarbonyl)-8-oxo-5,6,7,8-tetrahydropyrazolo[4,3-e][1,4]diazepin-2(4H)-yl)ethyl)piperidine-1-carboxylate
• 英文别名: tert-butyl 4-[2-[(6R)-6-benzyl-4-(cyclopropanecarbonyl)-8-oxo-6,7-dihydro-5H-pyrazolo[4,3-e][1,4]diazepin-2-yl]ethyl]piperidine-1-carboxylate
• CAS: 1166989-71-4
• 化学式: C₂₉H₃₉N₅O₄
• 分子量: 521.66
• InChiKey: QLQPJTFWTGFRKM-HSZRJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  96.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(2-(1-(tert-butoxycarbonyl)piperidin-4-yl)ethyl)-4-nitro-1H-pyrazole-3-carboxylic acid 在 palladium on activated charcoal 、 氢气 、 二异丁基氢化铝 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 16.0h， 生成 (R)-tert-butyl 4-(2-(6-benzyl-4-(cyclopropanecarbonyl)-8-oxo-5,6,7,8-tetrahydropyrazolo[4,3-e][1,4]diazepin-2(4H)-yl)ethyl)piperidine-1-carboxylate
  参考文献：
  名称：

  Discovery and structure–activity relationships of pyrazolodiazepine derivatives as the first small molecule agonists of the Drosophila sex peptide receptor

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2015.02.035