(1R,4S)-4-amino-3-fluorocyclopent-2-enecarboxylic acid | 918452-09-2

• 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: (1R,4S)-4-amino-3-fluorocyclopent-2-enecarboxylic acid
• 英文别名: (1R,4S)-4-amino-3-fluorocyclopent-2-ene-1-carboxylic acid
• CAS: 918452-09-2
• 化学式: C₆H₈FNO₂
• 分子量: 145.133
• InChiKey: HYFGNSPBWCIGEO-UCORVYFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 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：
  63.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (1S,4R)-6-fluoro-2-(4-methoxybenzyl)-2-azabicyclo[2.2.1]hept-5-en-3-one 在 盐酸 、 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 生成 (1R,4S)-4-amino-3-fluorocyclopent-2-enecarboxylic acid
  参考文献：
  名称：

  Fluorinated Conformationally Restricted γ-Aminobutyric Acid Aminotransferase Inhibitors

  摘要：

  On the basis of the structures of several potent inhibitor molecules for gamma-aminobutryric acid aminotransferase (GABA-AT) that were previously reported, six modified fluorine-containing conformationally restricted analogues were designed, synthesized, and tested as GABA-AT inhibitors. The syntheses of all six molecules followed from a readily synthesized ketone intermediate. Three of the molecules were found to be irreversible inhibitors of GABA-AT with comparable or larger k(inact)/K-I values than that of vigabatrin, a clinically used antiepilepsy drug, and the other three were reversible inhibitors. A possible mechanism for inactivation by one of the inactivators is proposed.

  DOI：

  10.1021/jm0608715

文献信息

• [EN] METHODS AND SYSTEMS FOR MODULATING HEPATIC GABA PRODUCTION OR RELEASE TO ALTER FOOD INTAKE IN MONOGASTRIC SPECIES<br/>[FR] PROCÉDÉS ET SYSTÈMES POUR MODULER LA PRODUCTION OU LA LIBÉRATION DE GABA HÉPATIQUE POUR MODIFIER L'APPORT ALIMENTAIRE CHEZ DES ESPÈCES MONOGASTRIQUES
  申请人：UNIV ARIZONA

  公开号：WO2021062048A2

  公开（公告）日：2021-04-01

  Methods and compositions (such as compounds, drugs, molecules, etc,) for modulating food intake, e.g., increasing food intake or reducing food intake, in a monogastric animal species. Certain methods herein feature administering to the animal a composition that depresses hepatic GABA production, depresses GABA release, inhibits expression or activity of GABA transaminase, inhibits expression or activity of particular GABA transporters associated with export of GABA, increases expression or activity of particular GABA transporters associated with GABA re- uptake, etc. The methods may help decrease food intake and subsequently improve weight loss. Certain methods herein may feature administering to the animal a composition that activates hepatic GABA production, activates GABA release, increases expression or activity of GABA transaminase, increases expression or activity of particular GABA transporters associated with export of GABA, decreases expression or activity of particular GABA transporters associated with GABA re-uptake, etc. The methods may help increase food intake, and subsequently help promote weight gain.
• [EN] METHODS AND COMPOSITIONS TO ALTER HEPATIC GABA RELEASE TO TREAT OBESITY-RELATED CONDITIONS<br/>[FR] PROCÉDÉS ET COMPOSITIONS POUR MODIFIER LA LIBÉRATION DE GABA HÉPATIQUE POUR TRAITER DES PROBLÈMES DE SANTÉ LIÉS À L'OBÉSITÉ
  申请人：UNIV ARIZONA

  公开号：WO2021203033A2

  公开（公告）日：2021-10-07

  Methods and compositions for treating conditions caused by altered hepatic GABA production and release, including hyperinsulinemia, insulin resistance, type II diabetes, obesity, and obesity-related conditions. The present invention describes hepatic GABA as a hepatokine. The methods herein feature manipulating the expression and/or activity of specific GABA transporters, e.g., increasing expression of SLC6A12 and/or SLC6A13 genes or increasing activity of the proteins for which they encode, BGT1 and/or GAT2; or decreasing expression of SLC6A6 and SLC6A8 genes or increasing the activity of the proteins for which they encode, TauT and/or CRT, which can increase hepatic GABA re-uptake or decrease hepatic GABA release to improve insulin sensitivity and prevent hypertension.
• Fluorinated Conformationally Restricted γ-Aminobutyric Acid Aminotransferase Inhibitors
  作者：Hejun Lu、Richard B. Silverman

  DOI：10.1021/jm0608715

  日期：2006.12.1

  On the basis of the structures of several potent inhibitor molecules for gamma-aminobutryric acid aminotransferase (GABA-AT) that were previously reported, six modified fluorine-containing conformationally restricted analogues were designed, synthesized, and tested as GABA-AT inhibitors. The syntheses of all six molecules followed from a readily synthesized ketone intermediate. Three of the molecules were found to be irreversible inhibitors of GABA-AT with comparable or larger k(inact)/K-I values than that of vigabatrin, a clinically used antiepilepsy drug, and the other three were reversible inhibitors. A possible mechanism for inactivation by one of the inactivators is proposed.