[2-oxo-2-(5-trifluoromethyl-furan-2-yl)-ethyl]-phosphonic acid dimethyl ester | 492471-53-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [2-oxo-2-(5-trifluoromethyl-furan-2-yl)-ethyl]-phosphonic acid dimethyl ester
• 英文别名: [2-(5-trifluoromethyl-furan-2-yl)-2-oxo-ethyl]phosphonic acid dimethyl ester；2-dimethoxyphosphoryl-1-[5-(trifluoromethyl)furan-2-yl]ethanone
• CAS: 492471-53-1
• 化学式: C₉H₁₀F₃O₅P
• 分子量: 286.144
• InChiKey: GDWTYYJRUGOIMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [2-oxo-2-(5-trifluoromethyl-furan-2-yl)-ethyl]-phosphonic acid dimethyl ester 在 sodium hydroxide 、 sodium tetrahydroborate 、 cerium(III) chloride 、 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 7-{(R)-2-[(E)-3-Hydroxy-3-(5-trifluoromethyl-furan-2-yl)-propenyl]-5-oxo-pyrrolidin-1-yl}-heptanoic acid
  参考文献：
  名称：

  Lactams as EP4 prostanoid receptor subtype selective agonists. Part 1: 2-Pyrrolidinones-stereochemical and lower side-chain optimization

  摘要：

  A series of 7-[(5R)-substituted 2-oxo-1-pyrrolidinyl]-heptanoic acids were prepared, their isomeric purity determined, and pharmacologically evaluated. Lactams with affinity for the EP4 receptor displayed agonist behavior. The lower side-chain of the lactam template could be substituted to afford ligands (e.g., 17, 24, 30, 31, and 33) of high potency and greater than 1000-fold affinity for EP4 versus the other EP prostanoid receptors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.01.063
• 作为产物：
  描述：

  methyl 5-(trifluoromethyl)furan-2-carboxylate 、 甲基膦酸二甲酯 在 正丁基锂 作用下， 生成 [2-oxo-2-(5-trifluoromethyl-furan-2-yl)-ethyl]-phosphonic acid dimethyl ester
  参考文献：
  名称：

  Lactams as EP4 prostanoid receptor subtype selective agonists. Part 1: 2-Pyrrolidinones-stereochemical and lower side-chain optimization

  摘要：

  A series of 7-[(5R)-substituted 2-oxo-1-pyrrolidinyl]-heptanoic acids were prepared, their isomeric purity determined, and pharmacologically evaluated. Lactams with affinity for the EP4 receptor displayed agonist behavior. The lower side-chain of the lactam template could be substituted to afford ligands (e.g., 17, 24, 30, 31, and 33) of high potency and greater than 1000-fold affinity for EP4 versus the other EP prostanoid receptors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.01.063

文献信息

• 8-Aza-11-deoxy prostaglandin analogues
  申请人：——

  公开号：US20030120079A1

  公开（公告）日：2003-06-26

  This invention relates to compounds which are generally EP 4 receptor agonists and which are represented by Formula I: 1 wherein A is a —CH 2 —CH 2 —, or —CH═CH—; B is absent, an aryl, or heteroaryl group; R 1 is alkyl, alkenyl, alkynyl, cycloalkylalkyl, heterocyclylalkyl, aryl, arylalkyl or heteroaryl, when B is aryl or heteroaryl and R 3 , R 4 , R 5 and R 6 are not simultaneously hydrogen, or R 1 is heterocyclylalkyl, aryl, or heteroaryl when B is absent and R 3 , R 4 , R 5 and R 6 are simultaneously hydrogen; and the other substituents are as defined in the specification; or individual isomers, racemic or non-racemic mixtures of isomers, or pharmaceutically acceptable salts or solvates thereof. The invention further relates to pharmaceutical compositions containing such compounds, methods for their use as therapeutic agents, and methods of preparation thereof.

  本发明涉及一般为EP4受体激动剂的化合物，其表示为式I：其中A为—CH2—CH2—，或—CH═CH—；B为不存在、芳基或杂芳基；R1为烷基、烯烃基、炔烃基、环烷基烷基、杂环烷基烷基、芳基、芳基烷基或杂芳基，当B为芳基或杂芳基且R3、R4、R5和R6不同时为氢时，或者R1为杂环烷基烷基、芳基或杂芳基，当B为不存在且R3、R4、R5和R6同时为氢时；其他取代基如规范中所定义；或其单体异构体、消旋或非消旋异构体混合物，或其药学上可接受的盐或溶剂。该发明还涉及含有此类化合物的药物组合物、用作治疗剂的方法以及其制备方法。
• 2-pyrrolidone derivatives as prostanoid agonists
  申请人：——

  公开号：US20030064964A1

  公开（公告）日：2003-04-03

  This invention relates to 8-aza prostanoid analogs which are generally EP 4 receptor agonists and are represented by Formula I: 1 wherein Q, B, X, J, Z, A and R 1 -R 6 are as defined, their synthesis and use for treatment of osteoporosis and increasing bone density.

  这项发明涉及一种通常为EP4受体激动剂的8-aza前列腺素类似物，其由以下式I表示：其中Q、B、X、J、Z、A和R1-R6如定义，它们的合成和用于治疗骨质疏松症和增加骨密度。
• 8-aza-11-deoxy prostaglandin analogues
  申请人：Elworthy Todd Richard

  公开号：US06900336B2

  公开（公告）日：2005-05-31

  This invention relates to compounds which are generally EP 4 receptor agonists and which are represented by Formula I: wherein A is a —CH 2 —CH 2 —, or —CH═CH—; B is absent, an aryl, or heteroaryl group; R 1 is alkyl, alkenyl, alkynyl, cycloalkylalkyl, heterocyclylalkyl, aryl, arylalkyl or heteroaryl, when B is aryl or heteroaryl and R 3 , R 4 , R 5 and R 6 are not simultaneously hydrogen, or R 1 is heterocyclylalkyl, aryl, or heteroaryl when B is absent and R 3 , R 4 , R 5 and R 6 are simultaneously hydrogen; and the other substituents are as defined in the specification; or individual isomers, racemic or non-racemic mixtures of isomers, or pharmaceutically acceptable salts or solvates thereof. The invention further relates to pharmaceutical compositions containing such compounds, methods for their use as therapeutic agents, and methods of preparation thereof.

  本发明涉及一类化合物，通常是EP4受体激动剂，其由式I表示：其中A是—CH2—CH2—或—CH═CH—；B是缺失的、芳基或杂芳基基团；当B为芳基或杂芳基且R3、R4、R5和R6不同时为氢时，R1是烷基、烯基、炔基、环烷基烷基、杂环基烷基、芳基、芳基烷基或杂芳基；当B缺失且R3、R4、R5和R6同时为氢时，R1是杂环基烷基、芳基或杂芳基；其他取代基如说明书中定义；或其单个异构体、外消旋或非外消旋异构体混合物或药学上可接受的盐或溶剂。本发明还涉及包含这些化合物的药物组合物、它们作为治疗剂的使用方法以及制备它们的方法。
• 2 PYRROLIDONE DERIVATIVES AS PROSTANOID AGONISTS
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1408961A1

  公开（公告）日：2004-04-21
• PROSTAGLANDIN ANALOGUES-AS EP4 RECEPTOR AGONISTS
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1409455A1

  公开（公告）日：2004-04-21