3-trans-cinnamoyl-4-hydroxy-benzoic acid | 145602-97-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-trans-cinnamoyl-4-hydroxy-benzoic acid
• 英文别名: 3-trans-Cinnamoyl-4-hydroxy-benzoesaeure；4-Hydroxy-3-trans-cinnamoyl-benzoesaeure；4-hydroxy-3-[(E)-3-phenylprop-2-enoyl]benzoic acid
• CAS: 145602-97-7
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: GIUGEYJJYYXIFU-SOFGYWHQSA-N

物化性质

• 沸点：
  520.5±50.0 °C(Predicted)
• 密度：
  1.336±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  3-trans-cinnamoyl-4-hydroxy-benzoic acid 在 氢氧化钾 、 溴 、 溶剂黄146 作用下， 生成 4-oxo-2-phenyl-4H-chromene-6-carboxylic acid
  参考文献：
  名称：

  Synthesis of carboxylated flavonoids as new leads for LTD4 antagonists

  摘要：

  A series of 3'- and 5'-carboxylated chalcones, 6- or 8-carboxylated flavones and 6-carboxylated flavanones, -flavanols and -flavans were prepared. The compounds were tested for their inhibitory activities against leukotriene D-4 (LTD(4)) induced contraction of guinea-pig ileum. A new and convenient synthetic route to 3-acetyl-2-hydroxybenzoic acid (1d), a key intermediate for the synthesis of 3'-carboxy-2'-hydroxychalcones and 8-carboxylated flavones, was developed. The activities of the tested compounds ranged from 0 to 63% inhibition at 10(-5) M drug concentration against a single challenge of 10(-8) M LTD(4). Several compounds were tested in a radioligand binding assay against [H-3]LTD(4) on guinea-pig lung membrane. The quinoline-containing chalcone 12 and flavone 17 were found to exhibit significant but weak affinities for LTD(4) receptors with pK(D)-values of 4.95 and 4.83, respectively, and are interesting lead structures for the development of rigid LTD(4) antagonists. In contrast, the rest of the compounds tested in the binding assay did not show significant displacement of the radioligand, implying that for these compounds the functional activity is probably not caused by competitive antagonism at the LTD(4) receptor. The exact mechanism of the relaxant activity remains unclear.

  DOI：

  10.1016/s0223-5234(97)89849-2
• 作为产物：
  描述：

  4-乙酰氧基苯甲酸 在 氢氧化钾 、 三氯化铝 作用下， 生成 3-trans-cinnamoyl-4-hydroxy-benzoic acid
  参考文献：
  名称：

  Shah; Shah, Journal of the Indian Chemical Society, 1949, vol. 26, p. 235,237

  摘要：

  DOI：

文献信息

• [EN] BICYCLIC IMIDAZOL DERIVATIVES AGAINST FLAVIVIRIDAE<br/>[FR] DERIVES DE L'IMIDAZOLE BICYCLIQUES DIRIGES CONTRE LES FLAVIVIRIDAE
  申请人：GENELABS TECH INC

  公开号：WO2005012288A1

  公开（公告）日：2005-02-10

  Disclosed are compounds, compositions and methods for treating Flaviviridae family virus infections.

  揭示了用于治疗黄病毒科病毒感染的化合物、组合物和方法。
• Bicyclic heteroaryl derivatives
  申请人：Schmitz Ulrich Franz

  公开号：US20050187390A1

  公开（公告）日：2005-08-25

  Disclosed are compounds, compositions and methods for treating Flaviviridae family virus infections.

  本发明涉及用于治疗黄病毒科病毒感染的化合物、组合物和方法。
• BICYCLIC HETEROARYL DERIVATIVES
  申请人：Schmitz Franz Ulrich

  公开号：US20090081165A1

  公开（公告）日：2009-03-26

  Disclosed are compounds, compositions and methods for treating Flaviviridae family virus infections.

  本发明揭示了用于治疗黄病毒科病毒感染的化合物、组合物和方法。
• Flavone derivative and medicine comprising the same
  申请人：KOWA CO. LTD.

  公开号：EP0834510A2

  公开（公告）日：1998-04-08

  This invention relates to a flavone derivative represented by the formula (1) or a salt thereof, and also to a medicine containing the same. wherein A represents H, halogen, phenyl, naphthyl, a group of the formula (2) in which X is H or halogen, B is -CH=CH-, -CH=N-, -N(R7)- (R7: lower alkyl or alkoxyalkyl), -O- or -S-; W represents a single bond, -CH2O- or -CH=CH-; at least one of R1 to R4 represents -COOH, -CN, alkyloxycarbonyl, tetrazolyl or -CONHR8 (R8: H, lower alkyl or phenylsulfonyl), the remainder thereof individually represent H, halogen, -OH, lower alkyl or lower alkoxyl; R5 represents H, -OH, lower alkoxyl, -O(CH2)mNR9R10 (R9,R10: H or lower alkyl, or coupled together with the adjacent N to form a phthalimido group; m: 1-5), or a group of the formula (3) (n: 1-5, ℓ: 2-3; and R6 represents H, halogen, lower alkyl or lower alkoxyl. A situation where A is H or halogen, W is a single bond and R5 is H is excluded. The compound (1) has excellent cys-LT1 receptor antagonism.

  本发明涉及一种由式（1）表示的黄酮衍生物或其盐，以及含有该衍生物的药物。 其中 A 代表 H、卤素、苯基、萘基、式（2）中 X 为 H 或卤素的基团，B 代表-CH＝CH-、-CH＝N-、-N(R7)-（R7：低级烷基或烷氧基烷基）、-O-或-S-；W 代表单键、-CH2O-或-CH＝CH-；R1 至 R4 中至少有一个代表-COOH、-CN、烷氧羰基、四唑基或-CONHR8（R8：代表 H、卤素、-OH、低级烷基或低级烷氧基；R5 代表 H、-OH、低级烷氧基、-O(CH2)mNR9R10（R9,R10：H或低级烷基，或与相邻的 N 偶联形成酞酰亚胺基团；m：1-5），或式（3）的基团（n：1-5，ℓ：2-3；R6 代表 H、卤素、低级烷基或低级烷氧基。不包括 A 为 H 或卤素、W 为单键、R5 为 H 的情况。化合物（1）具有优异的 cys-LT1 受体拮抗作用。
• Fujise; Abe, Nippon Kagaku Zasshi, 1956, vol. 77, p. 1313
  作者：Fujise、Abe

  DOI：——

  日期：——