(±)-4-amino-N-methylcyclopent-1-enecarboxamide | 1443124-66-0

• 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: (±)-4-amino-N-methylcyclopent-1-enecarboxamide
• 英文别名: 4-amino-N-methylcyclopentene-1-carboxamide
• CAS: 1443124-66-0
• 化学式: C₇H₁₂N₂O
• 分子量: 140.185
• InChiKey: SBNIACOOPOEVKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  methyl 4-tert-butoxycarbonylamino-2-cyclopenten-1-carboxylate 在 盐酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 sodium hydroxide 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 反应 6.25h， 生成 (±)-4-amino-N-methylcyclopent-1-enecarboxamide
  参考文献：
  名称：

  γ-Aminobutyric Acid(C) (GABA_C) Selective Antagonists Derived from the Bioisosteric Modification of 4-Aminocyclopent-1-enecarboxylic Acid: Amides and Hydroxamates

  摘要：

  Series of compounds were generated via the bioisosteric replacement of the carboxylate of 4-ACPCA (2) with hydroxamate or amide groups. All compounds from this study exhibited increased selectivity for GABA(C), the most potent being 4-ACPHA (10a, IC50 = 13 mu M) and 4-ACPAM (11a, IC50 = 10 mu M). This provides evidence that a zwitterionic structure is not essential for GABA(C) antagonists, rather the emphasis lies in appropriate heteroatoms to participate in hydrogen bonding.

  DOI：

  10.1021/jm4006548

文献信息

• γ-Aminobutyric Acid(C) (GABA_C) Selective Antagonists Derived from the Bioisosteric Modification of 4-Aminocyclopent-1-enecarboxylic Acid: Amides and Hydroxamates
  作者：Katherine E. S. Locock、Izumi Yamamoto、Priscilla Tran、Jane R. Hanrahan、Mary Chebib、Graham A. R. Johnston、Robin D. Allan

  DOI：10.1021/jm4006548

  日期：2013.7.11

  Series of compounds were generated via the bioisosteric replacement of the carboxylate of 4-ACPCA (2) with hydroxamate or amide groups. All compounds from this study exhibited increased selectivity for GABA(C), the most potent being 4-ACPHA (10a, IC50 = 13 mu M) and 4-ACPAM (11a, IC50 = 10 mu M). This provides evidence that a zwitterionic structure is not essential for GABA(C) antagonists, rather the emphasis lies in appropriate heteroatoms to participate in hydrogen bonding.