(±)-4-amino-N-hydroxycyclopent-1-enecarboxamide | 1443124-62-6

• 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-hydroxycyclopent-1-enecarboxamide
• 英文别名: 4-Acpha；4-amino-N-hydroxycyclopentene-1-carboxamide
• CAS: 1443124-62-6
• 化学式: C₆H₁₀N₂O₂
• 分子量: 142.158
• InChiKey: BPHHTKYPANYJGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  75.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (±)-tert-butyl 3-(tetrahydro-2H-pyran-2-yloxycarbamoyl)cyclopent-3-enylcarbamate 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 0.5h， 以84%的产率得到(±)-4-amino-N-hydroxycyclopent-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

• GABA AGONISTS AND ANTAGONISTS AFFECT DIFFERENTIATION OF HEMATOPOIETIC STEM CELLS AND MEGAKARYOCYTE PROGENITORS
  申请人：The Board of Trustees of the Leland Stanford Junior University

  公开号：US20220218753A1

  公开（公告）日：2022-07-14

  GABRR1 is shown to be expressed on subsets of hematopoietic stem cells (HSCs) and megakaryocyte progenitors (MkPs). Inhibition of GABRR1 inhibits MkP differentiation and reduction of platelet numbers in blood. Overexpression of GABRR1 or treatment with agonists significantly promotes MkP generation and growth of megakaryocytes.
• [EN] GABA AGONISTS AND ANTAGONISTS AFFECT DIFFERENTIATION OF HEMATOPOIETIC STEM CELLS AND MEGAKARYOCYTE PROGENITORS<br/>[FR] AGONISTES ET ANTAGONISTES GABA AFFECTANT LA DIFFÉRENCIATION DE CELLULES SOUCHES HÉMATOPOÏÉTIQUES ET DE PROGÉNITEURS DE MÉGACARYOCYTES
  申请人：UNIV LELAND STANFORD JUNIOR

  公开号：WO2020231935A1

  公开（公告）日：2020-11-19

  GABRR1 is shown to be expressed on subsets of hematopoietic stem cells (HSCs) and megakaryocyte progenitors (MkPs). Inhibition of GABRR1 inhibits MkP differentiation and reduction of platelet numbers in blood. Overexpression of GABRR1 or treatment with agonists significantly promotes MkP generation and growth of megakaryocytes.
• 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.