3,4-dihydro-1H-isoquinoline-2-carbohydrazide | 926630-12-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 3,4-dihydro-1H-isoquinoline-2-carbohydrazide
• CAS: 926630-12-8
• 化学式: C₁₀H₁₃N₃O
• 分子量: 191.233
• InChiKey: UDFKPYAJBQALOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  58.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-dihydro-1H-isoquinoline-2-carbohydrazide 、 氨甲酸,[(1S)-1-甲酰基戊基]-,1,1-二甲基乙基酯 在 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 为溶剂， 生成 {(S)-1-[(3,4-dihydro-1H-isoquinoline-2-carbonyl)-hydrazonomethyl]-pentyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Semicarbazone-based inhibitors of cathepsin K, are they prodrugs for aldehyde inhibitors?

  摘要：

  Starting from potent aldehyde inhibitors with poor drug properties, derivatization to semicarbazones led to the identification of a series of semicarbazone-based cathepsin K inhibitors with greater solubility and better pharmacokinetic profiles than their parent aldehydes. Furthermore, a representative semicarbazone inhibitor attenuated bone resorption in an ex vivo rat calvarial bone resorption model. However, based on enzyme inhibition comparisons at neutral pH, semicarbazone hydrolysis rates, and 13C NMR experiments, these semicarbazones probably function as prodrugs of aldehydes.

  DOI：

  10.1016/j.bmcl.2005.10.108
• 作为产物：
  描述：

  3,4-二氢-2(1H)-异喹啉羰基氯化物 在 肼 作用下， 以 1,4-二氧六环 为溶剂， 生成 3,4-dihydro-1H-isoquinoline-2-carbohydrazide
  参考文献：
  名称：

  Semicarbazone-based inhibitors of cathepsin K, are they prodrugs for aldehyde inhibitors?

  摘要：

  Starting from potent aldehyde inhibitors with poor drug properties, derivatization to semicarbazones led to the identification of a series of semicarbazone-based cathepsin K inhibitors with greater solubility and better pharmacokinetic profiles than their parent aldehydes. Furthermore, a representative semicarbazone inhibitor attenuated bone resorption in an ex vivo rat calvarial bone resorption model. However, based on enzyme inhibition comparisons at neutral pH, semicarbazone hydrolysis rates, and 13C NMR experiments, these semicarbazones probably function as prodrugs of aldehydes.

  DOI：

  10.1016/j.bmcl.2005.10.108

文献信息

• Semicarbazone-based inhibitors of cathepsin K, are they prodrugs for aldehyde inhibitors?
  作者：Kim K. Adkison、David G. Barrett、David N. Deaton、Robert T. Gampe、Anne M. Hassell、Stacey T. Long、Robert B. McFadyen、Aaron B. Miller、Larry R. Miller、J. Alan Payne、Lisa M. Shewchuk、Kevin J. Wells-Knecht、Derril H. Willard、Lois L. Wright

  DOI：10.1016/j.bmcl.2005.10.108

  日期：2006.2

  Starting from potent aldehyde inhibitors with poor drug properties, derivatization to semicarbazones led to the identification of a series of semicarbazone-based cathepsin K inhibitors with greater solubility and better pharmacokinetic profiles than their parent aldehydes. Furthermore, a representative semicarbazone inhibitor attenuated bone resorption in an ex vivo rat calvarial bone resorption model. However, based on enzyme inhibition comparisons at neutral pH, semicarbazone hydrolysis rates, and 13C NMR experiments, these semicarbazones probably function as prodrugs of aldehydes.