(Z)-2-Fluoro-3-{8-[2-(4-isopropyl-thiazol-2-yl)-ethyl]-2-morpholin-4-yl-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-acrylic acid ethyl ester | 475059-97-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: (Z)-2-Fluoro-3-{8-[2-(4-isopropyl-thiazol-2-yl)-ethyl]-2-morpholin-4-yl-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-acrylic acid ethyl ester
• 英文别名: Ethyl 2-fluoro-3-[2-morpholin-4-yl-4-oxo-8-[2-(4-propan-2-yl-1,3-thiazol-2-yl)ethyl]pyrido[1,2-a]pyrimidin-3-yl]prop-2-enoate；ethyl 2-fluoro-3-[2-morpholin-4-yl-4-oxo-8-[2-(4-propan-2-yl-1,3-thiazol-2-yl)ethyl]pyrido[1,2-a]pyrimidin-3-yl]prop-2-enoate
• CAS: 475059-97-3
• 化学式: C₂₅H₂₉FN₄O₄S
• 分子量: 500.594
• InChiKey: OLKHPNWQJPYZCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (Z)-2-Fluoro-3-{8-[2-(4-isopropyl-thiazol-2-yl)-ethyl]-2-morpholin-4-yl-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-acrylic acid ethyl ester 在 lithium hydroxide 、 碘 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 (Z)-2-Fluoro-3-{8-[2-(4-isopropyl-1,3-thiazol-2-yl)ethyl]-2-morpholino-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-propenoic acid
  参考文献：
  名称：

  MexAB-OprM specific efflux pump inhibitors in Pseudomonas aeruginosa. Part 4: Addressing the problem of poor stability due to photoisomerization of an acrylic acid moiety

  摘要：

  Exchange of the ethylene tether in a series of pyridopyrimidine-based MexAB-OprM specific efflux pump inhibitors to an amide bond stabilized the olefin of the acrylic acid moiety, preventing facile photoisomerization to the Z-isomer. Furthermore, the activity was drastically improved in the amide tether variants, providing extremely potent acrylic acid and vinyl tetrazole analogues. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.007
• 作为产物：
  描述：

  2-Hydroxy-8-[2-(4-isopropyl-1,3-thiazol-2-yl)ethyl]-4H-pyrido[1,2-a]pyrimidin-4-one 在 正丁基锂 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 生成 (Z)-2-Fluoro-3-{8-[2-(4-isopropyl-thiazol-2-yl)-ethyl]-2-morpholin-4-yl-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-acrylic acid ethyl ester
  参考文献：
  名称：

  MexAB-OprM specific efflux pump inhibitors in Pseudomonas aeruginosa. Part 4: Addressing the problem of poor stability due to photoisomerization of an acrylic acid moiety

  摘要：

  Exchange of the ethylene tether in a series of pyridopyrimidine-based MexAB-OprM specific efflux pump inhibitors to an amide bond stabilized the olefin of the acrylic acid moiety, preventing facile photoisomerization to the Z-isomer. Furthermore, the activity was drastically improved in the amide tether variants, providing extremely potent acrylic acid and vinyl tetrazole analogues. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.007