Ethyl 5-(3-oxopropyl)-1-phenylpyrazole-4-carboxylate | 1431322-81-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: Ethyl 5-(3-oxopropyl)-1-phenylpyrazole-4-carboxylate
• 英文别名: ethyl 5-(3-oxopropyl)-1-phenylpyrazole-4-carboxylate
• CAS: 1431322-81-4
• 化学式: C₁₅H₁₆N₂O₃
• 分子量: 272.304
• InChiKey: UYFWOXWCXYJOCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  61.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 5-(3-oxopropyl)-1-phenylpyrazole-4-carboxylate 、 (3S,5S)-4-aminoadamantan-1-ol 在 三乙酰氧基硼氢化钠 、 溶剂黄146 、 sodium hydroxide 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 氯仿 、 甲醇 、 水 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Discovery of novel 7-membered cyclic amide derivatives that inhibit 11beta-hydroxysteroid dehydrogenase type 1

  摘要：

  A series of novel 5-trans-hydroxyadamantan-2-yl-5,6,7,8-tetrahydropyrazolo[4,3-c]azepin-4(1H)-ones that inhibit 11beta-hydroxysteroid dehydrogenase type 1 are described. We discovered these 7-membered cyclic amide derivatives by introducing a distinctive linker through pharmacophore analysis of known ligands included in X-ray co-crystal structures. Further optimization using docking studies led to highly potent inhibitors 15b and 27, which furthermore showed the potent efficacy in in vivo studies. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.090
• 作为产物：
  描述：

  6-(苄氧基)-3-氧代己酸乙酯 在 10% palladium hydroxide on charcoal 、 氢气 、 戴斯-马丁氧化剂 、 叔丁醇 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 Ethyl 5-(3-oxopropyl)-1-phenylpyrazole-4-carboxylate
  参考文献：
  名称：

  Discovery of novel 7-membered cyclic amide derivatives that inhibit 11beta-hydroxysteroid dehydrogenase type 1

  摘要：

  A series of novel 5-trans-hydroxyadamantan-2-yl-5,6,7,8-tetrahydropyrazolo[4,3-c]azepin-4(1H)-ones that inhibit 11beta-hydroxysteroid dehydrogenase type 1 are described. We discovered these 7-membered cyclic amide derivatives by introducing a distinctive linker through pharmacophore analysis of known ligands included in X-ray co-crystal structures. Further optimization using docking studies led to highly potent inhibitors 15b and 27, which furthermore showed the potent efficacy in in vivo studies. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.090

文献信息

• Discovery of novel 7-membered cyclic amide derivatives that inhibit 11beta-hydroxysteroid dehydrogenase type 1
  作者：Shuji Udagawa、Satoshi Sakami、Takahiro Takemura、Mikiya Sato、Takahiro Arai、Aiko Nitta、Takumi Aoki、Koji Kawai、Tomokatsu Iwamura、Seiji Okazaki、Takehiro Takahashi、Mie Kaino

  DOI：10.1016/j.bmcl.2013.01.090

  日期：2013.3

  A series of novel 5-trans-hydroxyadamantan-2-yl-5,6,7,8-tetrahydropyrazolo[4,3-c]azepin-4(1H)-ones that inhibit 11beta-hydroxysteroid dehydrogenase type 1 are described. We discovered these 7-membered cyclic amide derivatives by introducing a distinctive linker through pharmacophore analysis of known ligands included in X-ray co-crystal structures. Further optimization using docking studies led to highly potent inhibitors 15b and 27, which furthermore showed the potent efficacy in in vivo studies. (C) 2013 Elsevier Ltd. All rights reserved.