(RS)-2-(1-benzyloxy-5-cyclopropylmethyl-4-pyrazolyl)-2-(N-tert-butoxycarbonylamino)acetic acid methyl ester | 936566-83-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (RS)-2-(1-benzyloxy-5-cyclopropylmethyl-4-pyrazolyl)-2-(N-tert-butoxycarbonylamino)acetic acid methyl ester
• CAS: 936566-83-5
• 化学式: C₂₂H₂₉N₃O₅
• 分子量: 415.489
• InChiKey: PMQSXGNMSHNEBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  30.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  91.68
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (RS)-2-(1-benzyloxy-5-cyclopropylmethyl-4-pyrazolyl)-2-(N-tert-butoxycarbonylamino)acetic acid methyl ester 在 palladium on activated charcoal 盐酸 、 lithium hydroxide 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.0h， 生成 (RS)-2-amino-2-(5-cyclopropylmethyl-1-hydroxy-4-pyrazolyl)acetic acid hydrochloride
  参考文献：
  名称：

  Novel 5-substituted 1-pyrazolol analogues of ibotenic acid: Synthesis and pharmacology at glutamate receptors

  摘要：

  5-Substituted 1-pyrazolol analogues of ibotenic acid have been synthesized and pharmacologically characterized on ionotropic and metabotropic glutamate receptors (iGluRs and mGluRs). The syntheses involved introduction of bromide, alkyls, phenyl and arylalkyls in the 5-position of 1-benzyloxypyrazole leading to 5-substituted (RS)-2-amino-(1-hydroxy-4-pyrazolyl)acetic acids (5a-1). The pharmacological activities of the synthesized analogues ranged from the 5-cyclopropylmethyl analogue (5f) with weak but selective affinity for NMDA receptors (IC50 = 35 mu M), over the 5-n-propyl analogue (5c), which was a selective mGluR2 agonist (EC50 = 72 mu M), to the 5-cyclohexylmethyl analogue (5g), which was a selective mGluR2 antagonist (K-i = 32 mu M), and the 5-phenylethyl analogue (5j), which was a weak but apparently selective mGluR1 antagonist (K-i = 230 mu M). This series of compounds afforded GluR ligands with a broad spectrum of pharmacological profiles, and showing potential for development of new compounds with subtype-selective activities at various GluRs. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.02.047
• 作为产物：
  描述：

  1-(苄氧基)吡唑 在 三乙基硅烷 、 正丁基锂 、 异丙基氯化镁 、 一氯化碘 、 potassium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 氯仿 为溶剂， 反应 0.17h， 生成 (RS)-2-(1-benzyloxy-5-cyclopropylmethyl-4-pyrazolyl)-2-(N-tert-butoxycarbonylamino)acetic acid methyl ester
  参考文献：
  名称：

  Novel 5-substituted 1-pyrazolol analogues of ibotenic acid: Synthesis and pharmacology at glutamate receptors

  摘要：

  5-Substituted 1-pyrazolol analogues of ibotenic acid have been synthesized and pharmacologically characterized on ionotropic and metabotropic glutamate receptors (iGluRs and mGluRs). The syntheses involved introduction of bromide, alkyls, phenyl and arylalkyls in the 5-position of 1-benzyloxypyrazole leading to 5-substituted (RS)-2-amino-(1-hydroxy-4-pyrazolyl)acetic acids (5a-1). The pharmacological activities of the synthesized analogues ranged from the 5-cyclopropylmethyl analogue (5f) with weak but selective affinity for NMDA receptors (IC50 = 35 mu M), over the 5-n-propyl analogue (5c), which was a selective mGluR2 agonist (EC50 = 72 mu M), to the 5-cyclohexylmethyl analogue (5g), which was a selective mGluR2 antagonist (K-i = 32 mu M), and the 5-phenylethyl analogue (5j), which was a weak but apparently selective mGluR1 antagonist (K-i = 230 mu M). This series of compounds afforded GluR ligands with a broad spectrum of pharmacological profiles, and showing potential for development of new compounds with subtype-selective activities at various GluRs. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.02.047