(E) 2-styryl-6-carboxymethyl-1,1'-biphenyl-3'-carboxylic acid | 163117-98-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E) 2-styryl-6-carboxymethyl-1,1'-biphenyl-3'-carboxylic acid
• 英文别名: 2-styryl-6-carboxymethyl-1,1'-biphenyl-3'-carboxylic acid；3-[2-(carboxymethyl)-6-[(E)-2-phenylethenyl]phenyl]benzoic acid
• CAS: 163117-98-4
• 化学式: C₂₃H₁₈O₄
• 分子量: 358.394
• InChiKey: KGKBKNVVOPOLMA-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  stannane 、 3'-Carboethoxy-(E)-2-[(5,6,7,8-tetrahydro-5,5,8,8,-tetramethyl-2-naphthalenyl)-1-propenyl]-[1,1'-biphenyl]-6-acetic acid, ethyl ester 、 (E) 2-styryl-6-carboxymethyl-1,1'-biphenyl-3'-carboxylic acid 、 3'-carboethoxy-2-trifluoromethylsulphonyloxy-1,1'-biphenyl-6-acetic acid, ethyl ester 以 正己烷 、 乙酸乙酯 为溶剂， 生成 3'-carboxy-(E)-2-[(5,6,7,8-tetrahydro-5,5,8,8,-tetramethyl-2-naphthalenyl)-1-propenyl]-[1,1'-biphenyl]-6-acetic acid
  参考文献：
  名称：

  Biaryl phospholipase A.sub.2 inhibitors

  摘要：

  某些新型联苯化合物是有效的磷脂酶A.sub.2（PLA.sub.2）抑制剂。

  公开号：

  US05391817A1
• 作为产物：
  描述：

  3'-carboethoxy-2-trifluoromethylsulphonyloxy-1,1'-biphenyl-6-acetic acid, ethyl ester 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium hydroxide 、 lithium chloride 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.33h， 生成 (E) 2-styryl-6-carboxymethyl-1,1'-biphenyl-3'-carboxylic acid
  参考文献：
  名称：

  Biaryl diacid inhibitors of human s-PLA 2 with anti-inflammatory activity

  摘要：

  Twenty-four hydrophobic dicarboxylic acids are described which were evaluated as inhibitors of 14 kDa human platelet phospholipase A(2) (HP-PLA(2)). In general, biarylacetic acid derivatives were found to be more active than biaryl acids or biaryl-propanoic acids. More potent inhibitors were obtained when hydrophobic groups were attached to the biaryl acid nucleus using an olefin linkage as compared to an ether linkage. Compounds with larger hydrophobic groups were usually more potent inhibitors of HP-PLA(2). Five of the compounds disclosed in this report (2, 4, 28, 36b and 36i) were found to possess significant anti-inflammatory activity in a phorbol ester induced mouse ear edema model of chronic inflammation. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00047-x

文献信息

• Biaryl phospholipase A2 inhibitors
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：EP0664282A1

  公开（公告）日：1995-07-26

  Biaryl compounds, effective phospholipase A₂ (PLA₂) inhibitors of Formulas I and II: wherein: Y= COOH, CH₂CO₂H, H, F, Cl, Br, I, COOR', CH₂CO₂R', CONH₂, COR'', CHO, CH₂OH, CH₂OR'', OH, OR'', CF₃, C₁₋₆ alkyl, C₁₋₆ alkenyl, C₁₋₆ haloalkyl, NO₂, P(O) (OH)₂, SO₂H, or SO₃H; Z= H, F, Cl, Br, I, CONH₂, COR'', CHO, CH₂OH, CH₂OR'', OH, OR'', CF₃, C₁₋₆ alkyl, C₁₋₆ alkenyl, C₁₋₆ haloalkyl, NO₂, P(O)(OH)₂, SO₂H, or SO₃H; X= (CH₂)n, n = 0, 1, or 2; or a cis or trans CH=CH; R= substituted or unsubstituted alkyl, aryl, arylalkyl, alkyloxy, arylalkyloxy, alkenyl, or arylalkenyl groups with the proviso that R must have 8 or more carbons; R'= H, C₁₋₆ alkyl, C(R¹)₂OC(O)R², CH₂CH₂NR³R⁴, CH₂CH₂CH₂NR³R⁴, or other groups yielding physiologically hydrolyzable esters; R''= C₁₋₆ alkyl; R¹= H, CH₃, C₂H₅, CH₂CH₂CH₃; R₂= C₆₋₁₂ aryl, C₁₋₇ linear, branched or cyclic alkyl, or C₁₋₇ linear branched or cyclic alkoxy; R³= R⁴, or, it may be linked with R⁴, to form a C₃-C₆ cycloalkyl or a -CH₂CH₂OCH₂CH₂- group; and R⁴= C₁₋₃ alkyl; or salts thereof.

  式 I 和 II 的有效磷脂酶 A₂（PLA₂）抑制剂--联苯化合物： 其中 Y= COOH、CH₂CO₂H、H、F、Cl、Br、I、COOR'、CH₂CO₂R'、CONH₂、COR''、CHO、CH₂OH、CH₂OR''、OH、OR''、CF₃、C₁₋₆ 烷基、C₁₋₆ 烯基、C₁₋₆ 卤代烷基、NO₂、P(O) (OH)₂、SO₂H 或 SO₃H； Z= H、F、Cl、Br、I、CONH₂、COR''、CHO、CH₂OH、CH₂OR''、OH、OR''、CF₃、C₁₋₆ 烷基、C₁₋₆ 烯基、C₁₋₆ 卤代烷基、NO₂、P(O)(OH)₂、SO₂H 或 SO₃H； X= (CH₂)n，n = 0、1 或 2；或顺式或反式 CH=CH； R= 取代或未取代的烷基、芳基、芳烷基、烷氧基、芳烷氧基、烯基或芳烯基，但 R 必须具有 8 个或 8 个以上碳原子； R'＝H、C₁₋₆烷基、C(R¹)₂OC(O)R²、CH₂CH₂NR³R⁴、CH₂CH₂CH₂NR³R⁴或其他可产生生理性水解酯的基团； R''= C₁₋₆ 烷基； R¹= h、ch₃、c₂h₅、ch₂ch₂ch₃； R₂= C₆₋₁₂ 芳基，C₁₋₇ 直链、支链或环状烷基，或 C₁₋₇ 直链、支链或环状烷氧基； R³= R⁴，或可与 R⁴ 连接，形成 C₃-C₆ 环烷基或 -CH₂CH₂OCH₂CH₂- 基团；以及 R⁴= C₁₋₃ 烷基；或其盐。
• US5391817A
  申请人：——

  公开号：US5391817A

  公开（公告）日：1995-02-21