5-[(1E)-2-(2,5-二羟基苯基)乙烯基]-2-羟基-苯甲酸 | 150258-63-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 5-[(1E)-2-(2,5-二羟基苯基)乙烯基]-2-羟基-苯甲酸
• 中文别名: 环丁烷1,2-二甲腈
• 英文名称: trans-1-(3'-carboxy-4'-hydroxyphenyl)-2-(2'',5''-dihydroxyphenyl)ethene
• 英文别名: 5-(2-(2,5-Dihydroxyphenyl)vinyl)-2-hydroxybenzoic acid；5-[(E)-2-(2,5-dihydroxyphenyl)ethenyl]-2-hydroxybenzoic acid
• CAS: 150258-63-2
• 化学式: C₁₅H₁₂O₅
• 分子量: 272.257
• InChiKey: AYPFKZQQTSLEJG-HNQUOIGGSA-N

物化性质

• 熔点：
  221-223°C dec.
• 沸点：
  563.9±50.0 °C(Predicted)
• 密度：
  1.508±0.06 g/cm3(Predicted)
• 溶解度：
  溶于DMSO、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(苄氧基)-5-甲酰基苯甲酸苄酯 在 sodium hydroxide 、 potassium tert-butylate 、 三溴化硼 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.5h， 生成 5-[(1E)-2-(2,5-二羟基苯基)乙烯基]-2-羟基-苯甲酸
  参考文献：
  名称：

  Non-amine based analogs of lavendustin A as protein-tyrosine kinase inhibitors

  摘要：

  The fermentation product lavendustin A (1) is a protein-tyrosine kinase (PTK) inhibitor whose active pharmacophore has previously been shown to reside in the more simplified salicyl-containing benzylamine 2. Amine 2 bears some structural resemblance to two other natural product PTK inhibitors, erbstatin (3) and piceatannol (4). Non-amine containing analogues of 2 were therefore synthesized which incorporated additional aspects of either erbstatin or piceatannol. Examination of these inhibitors in immunoprecipitated p56lck, epidermal growth factor receptor (EGFR), and c-erb B-2/HER 2/neu PTK preparations showed that compound 12 (IC50 = 60 nM) was one of the most potent p56lck inhibitors reported to date. These results demonstrate that nitrogen is not an essential component of the lavendustin A pharmacophore 2 and that 1,2-diarylethanes and -ethenes bearing a salicyl moiety appear to be valuable structural motifs for the construction of extremely potent PTK inhibitors.

  DOI：

  10.1021/jm00072a022

文献信息

• Disubstituted lavendustin A analogs and pharmaceutical compositions comprising the analogs
  申请人：THE UNITED STATES GOVERNMENT as represented by THE DEPARTMENT OF HEALTH AND HUMAN SERVICES

  公开号：EP1367046A9

  公开（公告）日：2004-05-12

  Disubstituted lavendustin A analogs that are PTK inhibitors having antiproliferative activity are described. Preferred compounds of the present invention, without limitation, satisfy either Formula 1 or Formula 2. Currently preferred compounds ,based on in vivo biological activity, are 4'-adamantylbenzoate-1'-N-1,4-dihydroxybenzylamine and 4'-adamantylmethylbenzoate-1'-N-1,4-dihydroxybenzylamine. The present invention also provides pharmaceutical compositions comprising effective amounts of disubstituted lavendustin A analogs. Such compositions also may comprise other active ingredients, other materials conventionally used in the formulation of pharmaceutical composition, and mixtures thereof. The compounds and compositions of the present invention can be used for treating subjects to, for example, inhibit the proliferation of living cells in the treatment of proliferative diseases.

  描述了具有抗增殖活性的PTK抑制剂的二取代拉文杜斯汀A类似物。本发明的优选化合物，不受限于，满足Formula 1或Formula 2中的任一种。根据体内生物活性，目前优选的化合物是4'-金刚烷基苯甲酸酯-1'-N-1,4-二羟基苯乙胺和4'-金刚烷基甲基苯甲酸酯-1'-N-1,4-二羟基苯乙胺。本发明还提供了含有二取代拉文杜斯汀A类似物有效量的药物组合物。这种组合物还可以包括其他活性成分、传统用于制备药物组合物的其他材料以及它们的混合物。本发明的化合物和组合物可用于治疗受试者，例如，在治疗增殖性疾病中抑制活细胞的增殖。
• Selective inhibition of C4-PEP carboxylases
  申请人：Heinrich Heine Universität Düsseldorf

  公开号：US10188107B2

  公开（公告）日：2019-01-29

  The present invention relates to the use of a compound, a salt or solvate thereof as C4 plant selective herbicide wherein said compound has a structure according to formula (I) wherein A is a cyclic alkyl, aryl, heterocycloalkyl, or heteroaryl group, and B is a cyclic alkyl, aryl, heterocycloalkyl, or heteroaryl group, and wherein R1, R2, R3, R4 and R5 are, independently of each other H or an alkyl group, and wherein integer i is 0 or 1, preferably 1, and the bond (a) is a single or double bond, and wherein in case (a) is a double bond, n is 0 and X is O or S, and wherein in case (a) is a single bond n is 1, and X is H or an alkyl group, and wherein the bond (b) is a single or double bond, and wherein in case (b) is a double bond, m and p are 0, and wherein in case (b) is a single bond m and p are both 1, and/or according to formula (II) including tautomeric structures thereof, wherein R01 and R02 are independently of each other selected from the group consisting of H, OH, carboxylic acid, ester, alkyl, alkoxy and halogen, wherein Y1 is selected from the group consisting of (S(═O)2), S(═O)) and (C(═O)), and wherein Y2 is O, and wherein r is 0 or 1 and wherein in case r is 0, q and s are 1, and wherein in case r is 1, q and s are 0, and wherein R01, R02, R04, R05, R06, R07, R04#, R05#, R06#, R07#, R09, R010, R011 and R012 are independently of each other selected from the group consisting of H, OH, —SO3H, carboxylic acid, ester, alkyl, alkoxy and halogen, said compound being capable of binding to the malate binding site comprised by a phosphoenolpyruvate carboxylase from a C4 plant, thereby inhibiting said phosphoenolpyruvate carboxylase.

  本发明涉及一种化合物、其盐或溶液作为 C4 植物选择性除草剂的用途，其中所述化合物具有符合式 (I) 的结构，其中 A 是环烷基、芳基、杂环烷基或杂芳基，B 是环烷基、芳基、杂环烷基或杂芳基，R1、R2、R3、R4 和 R5 相互独立地为 H 或烷基、其中整数 i 为 0 或 1，优选 1，键（a）为单键或双键，在（a）为双键的情况下，n 为 0，X 为 O 或 S，在（a）为单键的情况下，n 为 1，X 为 H 或烷基，键（b）为单键或双键，在（b）为双键的情况下，m 和 p 为 0，在（b）为单键的情况下，m 和 p 均为 1、和/或根据式（II），包括其同分异构体结构，其中 R01 和 R02 各自独立地选自 H、OH、羧酸、酯、烷基、烷氧基和卤素组成的组、其中 Y1 选自（S(═O)2）、S(═O)）和（C(═O)）组成的组，Y2 为 O，r 为 0 或 1，在 r 为 0 的情况下，q 和 s 为 1，在 r 为 1 的情况下、其中 R01、R02、R04、R05、R06、R07、R04#、R05#、R06#、R07#、R09、R010、R011 和 R012 相互独立地选自 H、OH、-SO3H、羧酸、酯、烷基、烷氧基和卤素组成的组、烷基、烷氧基和卤素，所述化合物能够与来自 C4 植物的磷酸烯醇丙酮酸羧化酶所包含的苹果酸结合位点结合，从而抑制所述磷酸烯醇丙酮酸羧化酶。
• SELECTIVE INHIBITION OF C4-PEP CARBOXYLASES
  申请人：HEINRICH HEINE UNIVERSITÄT DÜSSELDORF

  公开号：US20150366206A1

  公开（公告）日：2015-12-24

  The present invention relates to the use of a compound, a salt or solvate thereof as C4 plant selective herbicide wherein said compound has a structure according to formula (I) wherein A is a cyclic alkyl, aryl, heterocycloalkyl, or heteroaryl group, and B is a cyclic alkyl, aryl, heterocycloalkyl, or heteroaryl group, and wherein R 1 , R 2 , R 3 , R 4 and R 5 are, independently of each other H or an alkyl group, and wherein integer i is 0 or 1, preferably 1, and the bond (a) is a single or double bond, and wherein in case (a) is a double bond, n is 0 and X is O or S, and wherein in case (a) is a single bond n is 1, and X is H or an alkyl group, and wherein the bond (b) is a single or double bond, and wherein in case (b) is a double bond, m and p are 0, and wherein in case (b) is a single bond m and p are both 1, and/or according to formula (II) including tautomeric structures thereof, wherein R 01 and R 02 are independently of each other selected from the group consisting of H, OH, carboxylic acid, ester, alkyl, alkoxy and halogen, wherein Y 1 is selected from the group consisting of (S(=0)2), S(=0)) and (C(═O)), and wherein Y 2 is O, and wherein r is 0 or 1 and wherein in case r is 0, q and s are 1, and wherein in case r is 1, q and s are 0, and wherein R 01 , R 02 , R 04 , R 05 , R 06 , R 07 , R 04# , R 05# , R 06# , R 07# , R 09 , R 010 , R 011 and R 012 are independently of each other selected from the group consisting of H, OH, —SO3H, carboxylic acid, ester, alkyl, alkoxy and halogen, said compound being capable of binding to the malate binding site comprised by a phosphoenolpyruvate carboxylase from a C4 plant, thereby inhibiting said phosphoenolpyruvate carboxylase.
• [EN] SELECTIVE INHIBITION OF C4-PEP CARBOXYLASES<br/>[FR] INHIBITION SÉLECTIVE DE PEP CARBOXYLASES DE PLANTES EN C4
  申请人：HEINRICH HEINE UNIVERSITÄT DÜSSELDORF

  公开号：WO2014111448A1

  公开（公告）日：2014-07-24

  The present invention relates to the use of a compound, a salt or solvate thereof as C4 plant selective herbicide wherein said compound has a structure according to formula (I) wherein A is a cyclic alkyl, aryl, heterocycloalkyl, or heteroaryl group, and B is a cyclic alkyl, aryl, heterocycloalkyl, or heteroaryl group, and wherein R1, R2, R3, R4 and R5 are, independently of each other H or an alkyl group, and wherein integer i is 0 or 1, preferably 1, and the bond (a) is a single or double bond, and wherein in case (a) is a double bond, n is 0 and X is O or S, and wherein in case (a) is a single bond n is 1, and X is H or an alkyl group, and wherein the bond (b) is a single or double bond, and wherein in case (b) is a double bond, m and p are 0, and wherein in case (b) is a single bond m and p are both 1, and/or according to formula (II) including tautomeric structures thereof, wherein R01 and R02 are independently of each other selected from the group consisting of H, OH, carboxylic acid, ester, alkyl, alkoxy and halogen, wherein Y 1 is selected from the group consisting of (S(=0)2), S(=0)) and (C(=O)), and wherein Y2 is O, and wherein r is 0 or 1 and wherein in case r is 0, q and s are 1, and wherein in case r is 1, q and s are 0, and wherein R01, R02, R04, R05, R06, R07, R04#, R05#, R06#, R07#, R09, R010, R011 and R012 are independently of each other selected from the group consisting of H, OH, -SO3H, carboxylic acid, ester, alkyl, alkoxy and halogen, said compound being capable of binding to the malate binding site comprised by a phosphoenolpyruvate carboxylase from a C4 plant, thereby inhibiting said phosphoenolpyruvate carboxylase.
• Non-amine based analogs of lavendustin A as protein-tyrosine kinase inhibitors
  作者：Mark S. Smyth、Irena Stefanova、Frank Hartmann、Ivan D. Horak、Nir Osherov、Alexander Levitzki、Terrence R. Burke

  DOI：10.1021/jm00072a022

  日期：1993.10

  The fermentation product lavendustin A (1) is a protein-tyrosine kinase (PTK) inhibitor whose active pharmacophore has previously been shown to reside in the more simplified salicyl-containing benzylamine 2. Amine 2 bears some structural resemblance to two other natural product PTK inhibitors, erbstatin (3) and piceatannol (4). Non-amine containing analogues of 2 were therefore synthesized which incorporated additional aspects of either erbstatin or piceatannol. Examination of these inhibitors in immunoprecipitated p56lck, epidermal growth factor receptor (EGFR), and c-erb B-2/HER 2/neu PTK preparations showed that compound 12 (IC50 = 60 nM) was one of the most potent p56lck inhibitors reported to date. These results demonstrate that nitrogen is not an essential component of the lavendustin A pharmacophore 2 and that 1,2-diarylethanes and -ethenes bearing a salicyl moiety appear to be valuable structural motifs for the construction of extremely potent PTK inhibitors.