N-(1H-5-Indazolyl)-N-(1-phenethyl-4-piperidyl)amine | 118142-50-0

• 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: N-(1H-5-Indazolyl)-N-(1-phenethyl-4-piperidyl)amine
• 英文别名: N-[1-(2-phenylethyl)piperidin-4-yl]-1H-indazol-5-amine
• CAS: 118142-50-0
• 化学式: C₂₀H₂₄N₄
• 分子量: 320.437
• InChiKey: MCYVKDVSGUBCBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  44
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲氧基乙酰氯 、 N-(1H-5-Indazolyl)-N-(1-phenethyl-4-piperidyl)amine 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 0.5h， 以57%的产率得到N-(1H-indazol-5-yl)-2-methoxy-N-[1-(2-phenylethyl)piperidin-4-yl]acetamide
  参考文献：
  名称：

  New 4-(heteroanilido)piperidines, structurally related to the pure opioidagonist fentanyl, with agonist and/or antagonist properties

  摘要：

  A research program based on certain heterocyclic modifications (12-50) of the fentanyl (1) molecule has generated a novel class of opioids. In the mouse hot-plate test, these compounds were weaker analgesics than 1. Two types of antagonists were observed in morphine-treated rabbits: those (e.g., 28) that reversed both respiratory depression and analgesia and those (e.g. 32) that selectively reversed respiratory depression. Evaluation of in vitro binding affinities to rat brain opioid receptors was inconclusive for a common locus of action for the agonist as well as the antagonist component. Further pharmacological evaluation of 32, N-(2-pyrazinyl)-N-(1-phenethyl-4-piperidinyl)-2-furamide, in the rat showed it to be a potent analgesic (ED50 = 0.07 mg/kg, tail-flick test) with little cardiovascular and respiratory depression when compared to fentanyl.

  DOI：

  10.1021/jm00123a028
• 作为产物：
  描述：

  N-(2-苯乙基)-4-哌啶酮 在 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 N-(1H-5-Indazolyl)-N-(1-phenethyl-4-piperidyl)amine
  参考文献：
  名称：

  New 4-(heteroanilido)piperidines, structurally related to the pure opioidagonist fentanyl, with agonist and/or antagonist properties

  摘要：

  A research program based on certain heterocyclic modifications (12-50) of the fentanyl (1) molecule has generated a novel class of opioids. In the mouse hot-plate test, these compounds were weaker analgesics than 1. Two types of antagonists were observed in morphine-treated rabbits: those (e.g., 28) that reversed both respiratory depression and analgesia and those (e.g. 32) that selectively reversed respiratory depression. Evaluation of in vitro binding affinities to rat brain opioid receptors was inconclusive for a common locus of action for the agonist as well as the antagonist component. Further pharmacological evaluation of 32, N-(2-pyrazinyl)-N-(1-phenethyl-4-piperidinyl)-2-furamide, in the rat showed it to be a potent analgesic (ED50 = 0.07 mg/kg, tail-flick test) with little cardiovascular and respiratory depression when compared to fentanyl.

  DOI：

  10.1021/jm00123a028

文献信息

• Nitrogen-containing compounds having kinase inhibitory activity and drugs containing the same
  申请人：——

  公开号：US20040102437A1

  公开（公告）日：2004-05-27

  Compounds having an Rho kinase inhibitory activity. These compounds include the compound of general formula (I): Het-X-Z, pharmaceutically acceptable salts thereof and solvates of the same, wherein Het represents a monocyclic or dicyclic heterocycle group containing at least one nitrogen atom (for example, pyridyl, phthalimido); X represents (i) an —NH—C(═O)—NH-Q1- group, (ii) an —NH—C(═O)-Q2- group, etc. (wherein Q1 and Q2 represent each a bond, alkylene or alkenylene); and Z represents hydrogen, halogeno, a monocyclic, dicyclic ortricyclic carbon cycle or heterocycle, etc. (for example, optionally substituted phenyl).

  具有Rho激酶抑制活性的化合物。这些化合物包括通式（I）的化合物：Het-X-Z，其药学上可接受的盐和溶剂化物，其中Het表示含有至少一个氮原子的单环或双环杂环基团（例如吡啶基，邻苯二甲酰亚胺基）；X表示（i）一个—NH—C(═O)—NH-Q1-基团，（ii）一个—NH—C(═O)-Q2-基团等（其中Q1和Q2分别表示键，烷基或烯基）；Z表示氢，卤素，单环，双环或三环碳环或杂环等（例如可选取代苯基）。
• NITROGEN-CONTAINING COMPOUNDS HAVING KINASE INHIBITORY ACTIVITY AND DRUGS CONTAINING THE SAME
  申请人：Kyowa Hakko Kirin Co., Ltd.

  公开号：EP1256574B1

  公开（公告）日：2012-01-18
• BAGLEY, JEROME R.;WYNN, RICHARD L.;RUDO, FRIEDA G.;DOORLEY, BRIAN M.;SPEN+, J. MED. CHEM., 32,(1989) N, C. 663-671
  作者：BAGLEY, JEROME R.、WYNN, RICHARD L.、RUDO, FRIEDA G.、DOORLEY, BRIAN M.、SPEN+

  DOI：——

  日期：——
• US7217722B2
  申请人：——

  公开号：US7217722B2

  公开（公告）日：2007-05-15
• New 4-(heteroanilido)piperidines, structurally related to the pure opioidagonist fentanyl, with agonist and/or antagonist properties
  作者：Jerome R. Bagley、Richard L. Wynn、Frieda G. Rudo、Brian M. Doorley、H. Kenneth Spencer、Theodore Spaulding

  DOI：10.1021/jm00123a028

  日期：1989.3

  A research program based on certain heterocyclic modifications (12-50) of the fentanyl (1) molecule has generated a novel class of opioids. In the mouse hot-plate test, these compounds were weaker analgesics than 1. Two types of antagonists were observed in morphine-treated rabbits: those (e.g., 28) that reversed both respiratory depression and analgesia and those (e.g. 32) that selectively reversed respiratory depression. Evaluation of in vitro binding affinities to rat brain opioid receptors was inconclusive for a common locus of action for the agonist as well as the antagonist component. Further pharmacological evaluation of 32, N-(2-pyrazinyl)-N-(1-phenethyl-4-piperidinyl)-2-furamide, in the rat showed it to be a potent analgesic (ED50 = 0.07 mg/kg, tail-flick test) with little cardiovascular and respiratory depression when compared to fentanyl.