Tert-butyl 3-[3-(3-methylphenyl)-1,2,4-oxadiazol-5-yl]azetidine-1-carboxylate | 1403775-95-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: Tert-butyl 3-[3-(3-methylphenyl)-1,2,4-oxadiazol-5-yl]azetidine-1-carboxylate
• 英文别名: tert-butyl 3-[3-(3-methylphenyl)-1,2,4-oxadiazol-5-yl]azetidine-1-carboxylate
• CAS: 1403775-95-0
• 化学式: C₁₇H₂₁N₃O₃
• 分子量: 315.372
• InChiKey: FIXLITSVXGWTFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  68.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Tert-butyl 3-[3-(3-methylphenyl)-1,2,4-oxadiazol-5-yl]azetidine-1-carboxylate 在 盐酸 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 3-(3-Methylphenyl)-5-[1-(3-methylphenyl)sulfonylazetidin-3-yl]-1,2,4-oxadiazole
  参考文献：
  名称：

  Azetidinyl oxadiazoles as potent mGluR5 positive allosteric modulators

  摘要：

  A novel series of aryl azetidinyl oxadiazoles are identified as mGluR5 positive allosteric modulators (PAMs) with improved physico-chemical properties. N-substituted cyclohexyl and exo-norbornyl carboxamides, and carbamate analogs of azetidines are moderate to potent mGluR5 PAMs. The aryl, lower alkyl carboxamides analogs and sulfonamide analogs of azetidines are moderate mGluR5 negative allosteric modulators (NAMs). In the aryl oxadiazole moiety, substituents such as fluoro, chloro and methyl are well tolerated at the meta position while para substituents led to either inactive compounds or NAMs. A tight pharmacophore and subtle 'PAM to NAM switching' with close analogs makes the optimization of the series extremely challenging. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.044
• 作为产物：
  描述：

  3-甲基苄胺肟 、 1-N-Boc-3-吖丁啶羧酸 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 Tert-butyl 3-[3-(3-methylphenyl)-1,2,4-oxadiazol-5-yl]azetidine-1-carboxylate
  参考文献：
  名称：

  Azetidinyl oxadiazoles as potent mGluR5 positive allosteric modulators

  摘要：

  A novel series of aryl azetidinyl oxadiazoles are identified as mGluR5 positive allosteric modulators (PAMs) with improved physico-chemical properties. N-substituted cyclohexyl and exo-norbornyl carboxamides, and carbamate analogs of azetidines are moderate to potent mGluR5 PAMs. The aryl, lower alkyl carboxamides analogs and sulfonamide analogs of azetidines are moderate mGluR5 negative allosteric modulators (NAMs). In the aryl oxadiazole moiety, substituents such as fluoro, chloro and methyl are well tolerated at the meta position while para substituents led to either inactive compounds or NAMs. A tight pharmacophore and subtle 'PAM to NAM switching' with close analogs makes the optimization of the series extremely challenging. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.044

文献信息

• Azetidinyl oxadiazoles as potent mGluR5 positive allosteric modulators
  作者：Mathivanan Packiarajan、Christine G. Mazza Ferreira、Sang-Phyo Hong、Andrew D. White、Gamini Chandrasena、Xiaosui Pu、Robbin M. Brodbeck、Albert J. Robichaud

  DOI：10.1016/j.bmcl.2012.08.044

  日期：2012.10

  A novel series of aryl azetidinyl oxadiazoles are identified as mGluR5 positive allosteric modulators (PAMs) with improved physico-chemical properties. N-substituted cyclohexyl and exo-norbornyl carboxamides, and carbamate analogs of azetidines are moderate to potent mGluR5 PAMs. The aryl, lower alkyl carboxamides analogs and sulfonamide analogs of azetidines are moderate mGluR5 negative allosteric modulators (NAMs). In the aryl oxadiazole moiety, substituents such as fluoro, chloro and methyl are well tolerated at the meta position while para substituents led to either inactive compounds or NAMs. A tight pharmacophore and subtle 'PAM to NAM switching' with close analogs makes the optimization of the series extremely challenging. (c) 2012 Elsevier Ltd. All rights reserved.