(R)-3-[1-(3-Methoxy-phenyl)-meth-(E)-ylideneaminooxy]-2-methyl-propionic acid methyl ester | 430425-06-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-3-[1-(3-Methoxy-phenyl)-meth-(E)-ylideneaminooxy]-2-methyl-propionic acid methyl ester
• 英文别名: methyl (2R)-3-[(E)-(3-methoxyphenyl)methylideneamino]oxy-2-methylpropanoate
• CAS: 430425-06-2
• 化学式: C₁₃H₁₇NO₄
• 分子量: 251.282
• InChiKey: LLHWOVPBTDALKC-WWNSAXIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  57.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-3-[1-(3-Methoxy-phenyl)-meth-(E)-ylideneaminooxy]-2-methyl-propionic acid methyl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以36%的产率得到(R)-3-[1-(3-Methoxy-phenyl)-meth-(E)-ylideneaminooxy]-2-methyl-propionic acid
  参考文献：
  名称：

  Enantiopure 3-(arylmethylidene)aminoxy-2-methylpropionic acids: synthesis and antiinflammatory properties

  摘要：

  Some optically active 3-(arylmethylidene)aminoxy- (3a-g, 4a-g) and fluorenylideneaminoxy-2-methylpropionic acids (5, 6), were prepared as analogues of the antiinflammatory arylpropionic acids of type B, in which the aromatic group is substituted by an MAOM moiety. Some of the new compounds. tested in vivo for their antiinflammatory properties by means of the carrageenan-induced paw edema method in rats, exhibited activity indices similar to that shown in the same test by ibuprofen. Compounds 3a.b and 4a,b, for which at least one of the two enantiomers had shown an inhibition value higher than 40% in the in vivo test, were assayed for their in vitro enzymatic inhibitory activity. showing percentage inhibition values between 40 and 50% at a concentration of 10 muM against COX-2: at the same concentration, they appeared to be devoid of any activity towards COX-1. Compounds 3a.b and 4a,b also proved to possess a similar toxicity. The lack of enantioselectivity shown by compounds 3-6 was tentatively explained in terms of a conformational freedom of the enantiomers which allows their quasi-superimposition. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01275-2
• 作为产物：
  描述：

  (-)-甲基-D-BATA-羟基异丁酸酯 在 一水合肼 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 25.0h， 生成 (R)-3-[1-(3-Methoxy-phenyl)-meth-(E)-ylideneaminooxy]-2-methyl-propionic acid methyl ester
  参考文献：
  名称：

  Enantiopure 3-(arylmethylidene)aminoxy-2-methylpropionic acids: synthesis and antiinflammatory properties

  摘要：

  Some optically active 3-(arylmethylidene)aminoxy- (3a-g, 4a-g) and fluorenylideneaminoxy-2-methylpropionic acids (5, 6), were prepared as analogues of the antiinflammatory arylpropionic acids of type B, in which the aromatic group is substituted by an MAOM moiety. Some of the new compounds. tested in vivo for their antiinflammatory properties by means of the carrageenan-induced paw edema method in rats, exhibited activity indices similar to that shown in the same test by ibuprofen. Compounds 3a.b and 4a,b, for which at least one of the two enantiomers had shown an inhibition value higher than 40% in the in vivo test, were assayed for their in vitro enzymatic inhibitory activity. showing percentage inhibition values between 40 and 50% at a concentration of 10 muM against COX-2: at the same concentration, they appeared to be devoid of any activity towards COX-1. Compounds 3a.b and 4a,b also proved to possess a similar toxicity. The lack of enantioselectivity shown by compounds 3-6 was tentatively explained in terms of a conformational freedom of the enantiomers which allows their quasi-superimposition. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01275-2

文献信息

• Enantiopure 3-(arylmethylidene)aminoxy-2-methylpropionic acids: synthesis and antiinflammatory properties
  作者：A Balsamo

  DOI：10.1016/s0223-5234(01)01275-2

  日期：2001.10

  Some optically active 3-(arylmethylidene)aminoxy- (3a-g, 4a-g) and fluorenylideneaminoxy-2-methylpropionic acids (5, 6), were prepared as analogues of the antiinflammatory arylpropionic acids of type B, in which the aromatic group is substituted by an MAOM moiety. Some of the new compounds. tested in vivo for their antiinflammatory properties by means of the carrageenan-induced paw edema method in rats, exhibited activity indices similar to that shown in the same test by ibuprofen. Compounds 3a.b and 4a,b, for which at least one of the two enantiomers had shown an inhibition value higher than 40% in the in vivo test, were assayed for their in vitro enzymatic inhibitory activity. showing percentage inhibition values between 40 and 50% at a concentration of 10 muM against COX-2: at the same concentration, they appeared to be devoid of any activity towards COX-1. Compounds 3a.b and 4a,b also proved to possess a similar toxicity. The lack of enantioselectivity shown by compounds 3-6 was tentatively explained in terms of a conformational freedom of the enantiomers which allows their quasi-superimposition. (C) 2001 Editions scientifiques et medicales Elsevier SAS.