*-cis)>-1,6-dioxo-5-oxa-2-azaspiro<3.5>nonane-8-carboxylic acid | 144373-59-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: *-cis)>-1,6-dioxo-5-oxa-2-azaspiro<3.5>nonane-8-carboxylic acid
• 英文别名: (4S,8R)-3,6-dioxo-5-oxa-2-azaspiro[3.5]nonane-8-carboxylic acid
• CAS: 144373-59-1
• 化学式: C₈H₉NO₅
• 分子量: 199.163
• InChiKey: CCVGLMFDAMROFT-NVNXEXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  *-cis)>-1,6-dioxo-5-oxa-2-azaspiro<3.5>nonane-8-carboxylic acid 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.08h， 生成 *,3R^*)>-<(3-hydroxy-2-oxo-3-azetidinyl)methyl>butanedioic acid
  参考文献：
  名称：

  ATP-citrate-lyase as a target for hypolipidemic intervention. Sulfoximine and 3-hydroxy-.beta.-lactam containing analogs of citric acid as potential tight-binding inhibitors

  摘要：

  Citric acid analogues (+/-)-12a,b and (+/-)-17a,b, where one of the primary carboxylates has been replaced by a sulfoximinoyl and a 3-(3-hydroxy-beta-lactamyl) moiety, respectively, have been synthesized and evaluated as inhibitors of ATP-citrate lyase. The design of these inhibitors was based on methionine sulfoximine and tabtoxinine beta-lactam, potent, tight-binding inhibitors of glutamine synthetase. Both ATP-citrate lyase and glutamine synthetase employ phosphate-carboxylate anhydrides as a method for carboxylate activation during catalysis. Only one diastereomer, (+/-)-12a, displayed weak, reversible inhibition, while the remaining citrate analogues (+/-)-12b and (+/-)-17a,b were inactive against the lyase. No time-dependent inactivation of the enzyme was observed.

  DOI：

  10.1021/jm00104a014
• 作为产物：
  描述：

  *-cis)>-2-(tert-butyldimethylsilyl)-6-hydroxy-5-oxa-1-oxo-2-azaspiro<3.5>nonane-8-carboxylic acid benzyl ester 在 palladium on activated charcoal 四丁基氟化铵 、 氢气 、 sodium acetate 、 溶剂黄146 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.83h， 生成 *-cis)>-1,6-dioxo-5-oxa-2-azaspiro<3.5>nonane-8-carboxylic acid
  参考文献：
  名称：

  ATP-citrate-lyase as a target for hypolipidemic intervention. Sulfoximine and 3-hydroxy-.beta.-lactam containing analogs of citric acid as potential tight-binding inhibitors

  摘要：

  Citric acid analogues (+/-)-12a,b and (+/-)-17a,b, where one of the primary carboxylates has been replaced by a sulfoximinoyl and a 3-(3-hydroxy-beta-lactamyl) moiety, respectively, have been synthesized and evaluated as inhibitors of ATP-citrate lyase. The design of these inhibitors was based on methionine sulfoximine and tabtoxinine beta-lactam, potent, tight-binding inhibitors of glutamine synthetase. Both ATP-citrate lyase and glutamine synthetase employ phosphate-carboxylate anhydrides as a method for carboxylate activation during catalysis. Only one diastereomer, (+/-)-12a, displayed weak, reversible inhibition, while the remaining citrate analogues (+/-)-12b and (+/-)-17a,b were inactive against the lyase. No time-dependent inactivation of the enzyme was observed.

  DOI：

  10.1021/jm00104a014

文献信息

• Dolle Roland E., McNair David, Hughes Mark J., Kruse Lawrence I., Eggelst+, J. Med. Chem., 35 (1992) N 26, S 4875-4884
  作者：Dolle Roland E., McNair David, Hughes Mark J., Kruse Lawrence I., Eggelst+

  DOI：——

  日期：——