3-hydroxymethyl-5-methylcyclohexylaminomethyl-1,2,4-oxadiazole | 291771-30-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-hydroxymethyl-5-methylcyclohexylaminomethyl-1,2,4-oxadiazole
• 英文别名: [5-[[Cyclohexyl(methyl)amino]methyl]-1,2,4-oxadiazol-3-yl]methanol；[5-[[cyclohexyl(methyl)amino]methyl]-1,2,4-oxadiazol-3-yl]methanol
• CAS: 291771-30-7
• 化学式: C₁₁H₁₉N₃O₂
• 分子量: 225.291
• InChiKey: RVFPULZONXWLOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  62.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  cyclohexyl-phenyl-acetyl chloride 、 3-hydroxymethyl-5-methylcyclohexylaminomethyl-1,2,4-oxadiazole 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 苯 为溶剂， 反应 24.0h， 以97%的产率得到Cyclohexyl-phenyl-acetic acid 5-[(cyclohexyl-methyl-amino)-methyl]-[1,2,4]oxadiazol-3-ylmethyl ester
  参考文献：
  名称：

  Design, synthesis and binding at cloned muscarinic receptors of N -[5-(1′-substituted-acetoxymethyl)-3-oxadiazolyl] and N -[4-(1′-substituted-acetoxymethyl)-2-dioxolanyl] dialkyl amines

  摘要：

  Few muscarinic antagonists differentiate between the M-4 and M-2 muscarinic receptors. In a structure-activity study, aimed at discovering leads for the development of a M-4 muscarinic receptor-selective antagonist, we have synthesized and tested at cloned muscarinic receptors the binding of a group of dioxolane- or oxadiazole-dialkyl amines, and compared them to our compound 1, which contains the furan nucleus. Although none of these agents were particularly potent at M-4 receptors (K-d values were typically 30-70 nM), furan derivatives (-)1 and (+)1 were significantly more potent at M-4 receptors than at M-2 receptors (similar to 3- and 4-fold, respectively). The dioxolane derivatives 12b and 12c were more than 10-fold selective for the M-4 versus the M-2 receptors, while the dioxolane derivative 12e was 15-fold more potent at M-4 receptors than for M-2 receptors. However, these agents bound to M-3 receptors with potencies like that for the M-4 receptor, so they are not M-4-selective. The M-4/M-2 relative selectivities of some of our compounds are similar to the better hexahydrosiladifenidol derivatives, and may provide some important structural clues for the development of potent and selective M-4 antagonists. (C) 2000 Elsevier Science Ltd. Ail rights reserved.

  DOI：

  10.1016/s0968-0896(00)00092-4
• 作为产物：
  描述：

  3-benzyloxymethyl-5-methylcyclohexylaminomethyl-1,2,4-oxadiazole 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以77%的产率得到3-hydroxymethyl-5-methylcyclohexylaminomethyl-1,2,4-oxadiazole
  参考文献：
  名称：

  Design, synthesis and binding at cloned muscarinic receptors of N -[5-(1′-substituted-acetoxymethyl)-3-oxadiazolyl] and N -[4-(1′-substituted-acetoxymethyl)-2-dioxolanyl] dialkyl amines

  摘要：

  Few muscarinic antagonists differentiate between the M-4 and M-2 muscarinic receptors. In a structure-activity study, aimed at discovering leads for the development of a M-4 muscarinic receptor-selective antagonist, we have synthesized and tested at cloned muscarinic receptors the binding of a group of dioxolane- or oxadiazole-dialkyl amines, and compared them to our compound 1, which contains the furan nucleus. Although none of these agents were particularly potent at M-4 receptors (K-d values were typically 30-70 nM), furan derivatives (-)1 and (+)1 were significantly more potent at M-4 receptors than at M-2 receptors (similar to 3- and 4-fold, respectively). The dioxolane derivatives 12b and 12c were more than 10-fold selective for the M-4 versus the M-2 receptors, while the dioxolane derivative 12e was 15-fold more potent at M-4 receptors than for M-2 receptors. However, these agents bound to M-3 receptors with potencies like that for the M-4 receptor, so they are not M-4-selective. The M-4/M-2 relative selectivities of some of our compounds are similar to the better hexahydrosiladifenidol derivatives, and may provide some important structural clues for the development of potent and selective M-4 antagonists. (C) 2000 Elsevier Science Ltd. Ail rights reserved.

  DOI：

  10.1016/s0968-0896(00)00092-4

文献信息

• Design, synthesis and binding at cloned muscarinic receptors of N -[5-(1′-substituted-acetoxymethyl)-3-oxadiazolyl] and N -[4-(1′-substituted-acetoxymethyl)-2-dioxolanyl] dialkyl amines
  作者：Stefano Manfredini、Ilaria Lampronti、Silvia Vertuani、Nicola Solaroli、Maurizio Recanatini、David Bryan、Michael McKinney

  DOI：10.1016/s0968-0896(00)00092-4

  日期：2000.7

  Few muscarinic antagonists differentiate between the M-4 and M-2 muscarinic receptors. In a structure-activity study, aimed at discovering leads for the development of a M-4 muscarinic receptor-selective antagonist, we have synthesized and tested at cloned muscarinic receptors the binding of a group of dioxolane- or oxadiazole-dialkyl amines, and compared them to our compound 1, which contains the furan nucleus. Although none of these agents were particularly potent at M-4 receptors (K-d values were typically 30-70 nM), furan derivatives (-)1 and (+)1 were significantly more potent at M-4 receptors than at M-2 receptors (similar to 3- and 4-fold, respectively). The dioxolane derivatives 12b and 12c were more than 10-fold selective for the M-4 versus the M-2 receptors, while the dioxolane derivative 12e was 15-fold more potent at M-4 receptors than for M-2 receptors. However, these agents bound to M-3 receptors with potencies like that for the M-4 receptor, so they are not M-4-selective. The M-4/M-2 relative selectivities of some of our compounds are similar to the better hexahydrosiladifenidol derivatives, and may provide some important structural clues for the development of potent and selective M-4 antagonists. (C) 2000 Elsevier Science Ltd. Ail rights reserved.