2-(2-(benzyloxy)phenyl)propanenitrile | 134940-26-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(2-(benzyloxy)phenyl)propanenitrile
• 英文别名: 2-(2-benzyloxyphenyl)propionitrile；2-(2-Benzyloxyphenyl)-propionitrile；2-(2-phenylmethoxyphenyl)propanenitrile
• CAS: 134940-26-4
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: KAEMHYXYPPYCFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-(benzyloxy)phenyl)propanenitrile 在 三甲基铝 ammonium chloride 作用下， 以 氯仿 、 甲苯 为溶剂， 生成 2-(2-benzyloxyphenyl)propionamidine
  参考文献：
  名称：

  Ortho substituted aromatic compounds useful as antagonists of the pain

  摘要：

  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。

  公开号：

  US05811459A1
• 作为产物：
  描述：

  1-(2-苄氧基苯基)-乙醇 在 盐酸 、 calcium chloride 作用下， 以 1,4-二氧六环 、 二甲基亚砜 为溶剂， 反应 2.0h， 生成 2-(2-(benzyloxy)phenyl)propanenitrile
  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

• PHARMACEUTICALLY ACTIVE SUBSTITUTED AROMATIC COMPOUNDS
  申请人：ZENECA LIMITED

  公开号：EP0733033A1

  公开（公告）日：1996-09-25
• US5811459A
  申请人：——

  公开号：US5811459A

  公开（公告）日：1998-09-22
• [EN] PHARMACEUTICALLY ACTIVE SUBSTITUTED AROMATIC COMPOUNDS<br/>[FR] COMPOSES AROMATIQUES SUBSTITUES PHARMACEUTIQUEMENT ACTIFS
  申请人：ZENECA LIMITED

  公开号：WO1996011902A1

  公开（公告）日：1996-04-25

  (EN) The present invention relates to compounds of formula (I), wherein: A, B and D are various ring systems as defined in the description, R1 is one of a variety of groups as defined in the description, R3 is hydrogen or C1-4 alkyl and Z is of the formula -(CH(R5))m-, -(CHR5)pCR5=CR5(CHR5)q-, -(CHR5)rC(=O)CR5(CHR5)s- or -(CHR5t)C(=O) (CHR5)u-, wherein m is 2, 3 or 4, p and q are independently 0, 1 or 2 providing p+q is not greater than 2, one of r and s is 0 and the other is 1 and t and u are independently 0, 1, 2 or 3 providing t + u is not less than 1 or greater than 3; and R5 is hydrogen, methyl, ethyl, hydroxy, methoxy or ethoxy; and N-oxides where chemically possible; and S-oxides where chemically possible; and pharmaceutically acceptable salt and $i(in vivo) hydrolysable ester amide thereof. Processes for their preparation, their use as therapeutic agents and pharmaceutical compositions containing them.(FR) L'invention concerne des composés représentés par la formule (I): dans laquelle: A, B et D représentent différents systèmes cycliques, tels qu'ils sont définis dans la description, R1 représente un groupe parmi une variété de groupes, tels qu'ils sont définis dans la description, R3 représente hydrogène ou alkyle C1-4 et Z est représenté par la formule -(CH(R5))m-, -(CHR5)pCR5=CR5(CHR5)q-, -(CHR5)rC(=O)CR5(CHR5)s- ou -(CHR5t) C(=O) (CHR5)u-, dans laquelle m vaut 2, 3 ou 4, p et q valent indépendamment 0, 1 ou 2 sachant que p + q n'est pas supérieur à 2, r ou s vaut 0 et l'autre vaut 1 et t et u valent indépendamment 0, 1, 2 ou 3 à condition que t + u ne soit pas inférieur à 1 ou supérieur à 3; R5 représente hydrogène, méthyle, éthyle, hydroxy, méthoxy ou éthoxy; N-oxydes si cela est chimiquement possible; S-oxydes si cela est chimiquement possible; ainsi que leur sel pharmaceutiquement acceptable et leur amide d'ester hydrolysable $i(in vivo). Procédés servant à les préparer, leur utilisation en tant qu'agents thérapeutiques et compositions pharmaceutiques les contenant.
• 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。
• Potential antitumor agents. 63. Structure-activity relationships for side-chain analogs of the colon 38 active agent 9-oxo-9H-xanthene-4-acetic acid
  作者：Gordon W. Rewcastle、Graham J. Atwell、Bruce C. Baguley、Maruta Boyd、Lindy L. Thomsen、Li Zhuang、William A. Denny

  DOI：10.1021/jm00113a027

  日期：1991.9

  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.