Propan-2-yl 1h-indazole-3-carboxylate | 67364-16-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: Propan-2-yl 1h-indazole-3-carboxylate
• CAS: 67364-16-3
• 化学式: C₁₁H₁₂N₂O₂
• mdl: MFCD24740748
• 分子量: 204.228
• InChiKey: OUFDBISQRSEEQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 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：

  Propan-2-yl 1h-indazole-3-carboxylate 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 copper(II) acetate monohydrate 、 potassium carbonate 、 三乙胺 、 双三氟甲烷磺酰亚胺银盐 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 26.0h， 生成 isopropyl 7-allyl-1-(diisopropylcarbamoyl)-1H-indazole-3-carboxylate
  参考文献：
  名称：

  铑(III)-催化的吲唑的区域选择性C7-烯丙基化

  摘要：

  已经开发了一种有效的铑催化区域选择性 C-H 烯丙基化 N,N-二异丙基氨基甲酰基吲唑与烯丙基碳酸酯作为烯丙基化剂。该方法可以轻松获得具有高区域选择性、广泛底物范围和广泛官能团耐受性的 C7 烯丙基化吲唑。

  DOI：

  10.1055/s-0039-1691488
• 作为产物：
  描述：

  吲唑-3-羧酸 、 异丙醇 在 硫酸 作用下， 生成 Propan-2-yl 1h-indazole-3-carboxylate
  参考文献：
  名称：

  Design, synthesis and evaluation of N-benzoylindazole derivatives and analogues as inhibitors of human neutrophil elastase

  摘要：

  Human neutrophil elastase (HNE) plays an important role in tumour invasion and inflammation. A series of N-benzoylindazoles was synthesized and evaluated for their ability to inhibit HNE. We found that this scaffold is appropriate for HNE inhibitors and that the benzoyl fragment at position 1 is essential for activity. The most active compounds inhibited HNE activity with IC50 values in the submicromolar range. Furthermore, docking studies indicated that the geometry of an inhibitor within the binding site and energetics of Michaelis complex formation were key factors influencing the inhibitor's biological activity. Thus, N-benzoylindazole derivatives and their analogs represent novel structural templates that can be utilized for further development of efficacious HNE inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.036

文献信息

• Design, synthesis and evaluation of N-benzoylindazole derivatives and analogues as inhibitors of human neutrophil elastase
  作者：Letizia Crocetti、Maria Paola Giovannoni、Igor A. Schepetkin、Mark T. Quinn、Andrei I. Khlebnikov、Agostino Cilibrizzi、Vittorio Dal Piaz、Alessia Graziano、Claudia Vergelli

  DOI：10.1016/j.bmc.2011.06.036

  日期：2011.8

  Human neutrophil elastase (HNE) plays an important role in tumour invasion and inflammation. A series of N-benzoylindazoles was synthesized and evaluated for their ability to inhibit HNE. We found that this scaffold is appropriate for HNE inhibitors and that the benzoyl fragment at position 1 is essential for activity. The most active compounds inhibited HNE activity with IC50 values in the submicromolar range. Furthermore, docking studies indicated that the geometry of an inhibitor within the binding site and energetics of Michaelis complex formation were key factors influencing the inhibitor's biological activity. Thus, N-benzoylindazole derivatives and their analogs represent novel structural templates that can be utilized for further development of efficacious HNE inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.
• Rhodium(III)-Catalyzed Regioselective C7-Allylation of Indazoles
  作者：Jiyou Huo、Hongshun Yuan、Lanting Xu、Xianhua Pan

  DOI：10.1055/s-0039-1691488

  日期：2020.1

  An efficient rhodium-catalyzed regioselective C–H allylation of N,N-diisopropylcarbamoyl indazoles with allylic carbonates as allylating agents has been developed. This methodology provides facile access to C7-allylated indazoles with high regioselectivity, ample substrate scope and broad functional group tolerance.

  已经开发了一种有效的铑催化区域选择性 C-H 烯丙基化 N,N-二异丙基氨基甲酰基吲唑与烯丙基碳酸酯作为烯丙基化剂。该方法可以轻松获得具有高区域选择性、广泛底物范围和广泛官能团耐受性的 C7 烯丙基化吲唑。