2-(2-(benzyloxy)phenyl)propanoic acid | 134940-28-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 2-(2-(benzyloxy)phenyl)propanoic acid
• 英文别名: 2-(2-benzyloxyphenyl)propionic acid；2-(2-Phenylmethoxyphenyl)propanoic acid
• CAS: 134940-28-6
• 化学式: C₁₆H₁₆O₃
• 分子量: 256.301
• InChiKey: XZPXZZDSAQHXPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-(benzyloxy)phenyl)propanoic acid 在 palladium on activated charcoal 氢气 、 对甲苯磺酸 作用下， 以 乙醇 、 甲苯 为溶剂， 生成 3-methyl-3H-benzofuran-2-one
  参考文献：
  名称：

  Potential antitumor agents. 63. Structure-activity relationships for side-chain analogs of the colon 38 active agent 9-oxo-9H-xanthene-4-acetic acid

  摘要：

  A series of 16 analogues of the solid tumor active compound 9-oxo-9H-xanthene-4-acetic acid (XAA), with variations in the acetic acid side chain, have been prepared and evaluated for their ability to cause early haemorrhagic necrosis of colon 38 tumors in mice. The results extend the previous SAR for this class and confirm the necessity for a carboxylic acid group in a fixed disposition with respect to the xanthenone chromophore. None of the compounds showed superior potency to XAA itself, with virtually all alterations in the nature of the anionic center or its geometry with respect to the chromophore greatly reducing or abolishing activity. However, alpha-methylation of the side chain was permissible, and the two enantiomers of 5-methyl-alpha-methyl-XAA were separated and tested. Both were active, but the S-(+) enantiomer was much more dose-potent than the R-(-) enantiomer, in both the in vivo tumor necrosis assay and an in vitro assay measuring the stimulation of nitric oxide production by macrophages. This suggests that the enantiomers have different intrinsic activities, rather than differing in their vivo metabolism.

  DOI：

  10.1021/jm00113a027
• 作为产物：
  描述：

  氯化苄 在 盐酸 、 氢氧化钾 、 sodium hydroxide 、 sodium tetrahydroborate 、 四丁基溴化铵 、 calcium chloride 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 2-(2-(benzyloxy)phenyl)propanoic acid
  参考文献：
  名称：

  Potential antitumor agents. 63. Structure-activity relationships for side-chain analogs of the colon 38 active agent 9-oxo-9H-xanthene-4-acetic acid

  摘要：

  A series of 16 analogues of the solid tumor active compound 9-oxo-9H-xanthene-4-acetic acid (XAA), with variations in the acetic acid side chain, have been prepared and evaluated for their ability to cause early haemorrhagic necrosis of colon 38 tumors in mice. The results extend the previous SAR for this class and confirm the necessity for a carboxylic acid group in a fixed disposition with respect to the xanthenone chromophore. None of the compounds showed superior potency to XAA itself, with virtually all alterations in the nature of the anionic center or its geometry with respect to the chromophore greatly reducing or abolishing activity. However, alpha-methylation of the side chain was permissible, and the two enantiomers of 5-methyl-alpha-methyl-XAA were separated and tested. Both were active, but the S-(+) enantiomer was much more dose-potent than the R-(-) enantiomer, in both the in vivo tumor necrosis assay and an in vitro assay measuring the stimulation of nitric oxide production by macrophages. This suggests that the enantiomers have different intrinsic activities, rather than differing in their vivo metabolism.

  DOI：

  10.1021/jm00113a027

文献信息

• [EN] AMINOMETHYL-BIARYL DERIVATIVES AS COMPLEMENT FACTOR D INHIBITORS AND USES THEREOF<br/>[FR] DÉRIVÉS D'AMINOMÉTHYL-BIARYL EN TANT QU'INHIBITEURS DU FACTEUR D DU COMPLÉMENT ET LEURS UTILISATIONS
  申请人：NOVARTIS AG

  公开号：WO2015009977A1

  公开（公告）日：2015-01-22

  The present invention provides a compound of formula (I), a method for manufacturing the compounds of the invention, and its therapeutic uses. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition.

  本发明提供了一种公式(I)的化合物，一种制造本发明化合物的方法及其治疗用途。本发明进一步提供了一种药物活性剂的组合物和一种药物组合物。
• Ortho substituted aromatic compounds useful as antagonists of the pain
  申请人：Zeneca Limited

  公开号：US05811459A1

  公开（公告）日：1998-09-22

  The invention relates to compounds of the formula (I): ##STR1## wherein A, B and D are various ring systems such as phenyl, R.sup.1 includes carboxy, R.sup.3 is hydrogen or C.sub.1-4 alkyl and Z is a linking group such as --(CH(R.sup.5)).sub.m -- wherein m is 2, 3 or 4, and R.sub.5 includes hydrogen and methyl; and pharmaceutically acceptable salts and in vivo hydrolysable esters or amides thereof, processes for preparing these compounds, pharmaceutical compositions comprising them, and their use in the treatment of pain.

  该发明涉及以下式(I)的化合物：##STR1## 其中A、B和D是各种环系统，如苯基，R.sup.1包括羧基，R.sup.3是氢或C.sub.1-4烷基，Z是连接基，如--(CH(R.sup.5)).sub.m--其中m为2、3或4，R.sub.5包括氢和甲基；以及其药学上可接受的盐和体内可水解的酯或酰胺，制备这些化合物的方法，包含它们的药物组合物，以及它们在治疗疼痛中的用途。
• PHARMACEUTICALLY ACTIVE SUBSTITUTED AROMATIC COMPOUNDS
  申请人：ZENECA LIMITED

  公开号：EP0733033A1

  公开（公告）日：1996-09-25
• AMINOMETHYL-BIARYL DERIVATIVES AS COMPLEMENT FACTOR D INHIBITORS AND USES THEREOF
  申请人：Novartis AG

  公开号：EP3022182A1

  公开（公告）日：2016-05-25
• US4889952A
  申请人：——

  公开号：US4889952A

  公开（公告）日：1989-12-26