rac-3-(4-cyanophenoxy)-propane-1,2-diol | 57929-02-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: rac-3-(4-cyanophenoxy)-propane-1,2-diol
• 英文别名: 3-(4-cyanophenoxy)propane-1,2-diol；(+/-)-1-O-(4-cyanophenyl)glycerol；4-(2,3-Dihydroxypropoxy)benzonitrile
• CAS: 57929-02-9
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: DMVZVOUWLINXLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  73.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  rac-3-(4-cyanophenoxy)-propane-1,2-diol 以90%的产率得到
  参考文献：
  名称：

  WAGNER G.; HORN H., PHARMAZIE , 1975, 30, NO 6, 353-357

  摘要：

  DOI：
• 作为产物：
  描述：

  4-羟基苯甲腈 、 3-氯-1,2-丙二醇 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以60%的产率得到rac-3-(4-cyanophenoxy)-propane-1,2-diol
  参考文献：
  名称：

  Inhibition of Secreted Phospholipase A₂. 4-Glycerol Derivatives of 4,5-Dihydro-3-(4-tetradecyloxybenzyl)-1,2,4-4H-oxadiazol-5-one with Broad Activities

  摘要：

  Secreted phospholipases A(2) (sPLA(2)s) have been reported to play an important role in various inflammatory conditions and thus represent an attractive therapeutic target. Previous SAR studies from our laboratory have revealed certain important features of our recently discovered specific hGIIA sPLA(2) inhibitors, and we report here the synthesis and biological activities of glycerol-containing derivatives of our lead compound III (Figure 1). Efficient and selective synthesis methods have been developed to make glycerol trisubstituted by different groups on desired positions. In terms of biological activities, the best compounds (A3, A6, and A15) are more active than III (Figure 1), as potent as Me-Indoxam, an sPLA(2)s inhibitor of reference, against hGIIA, hGV, and hGX sPLA(2)s and at least 10 times less active toward the GIB enzymes in two in vitro assay systems. By synthesis of enantiopure (S)-A6, we demonstrated that no important improvement of the inhibitory potency could be achieved by this approach. Furthermore, the results show that the global lipophilicity is likely responsible for the anti-PLA(2) activity and two oxadiazolone moieties seem too big to be accommodated by the active site of the hGIIA enzyme.

  DOI：

  10.1021/jm060082n

文献信息

• [EN] PROCESS FOR THE ISOLATION OF 4-(OXIRANYLMETHOXY)-BENZONITRILES<br/>[FR] PROCÉDÉ D'ISOLEMENT DE 4-(OXIRANYLMÉTHOXY)BENZONITRILES
  申请人：ASTRAZENECA AB

  公开号：WO2006137773A1

  公开（公告）日：2006-12-28

  [EN] There is provided a process for the isolation of a compound of formula I, or a solvate thereof, from a mixture comprising a compound of formula I and a compound of formula II, wherein the mixture of compounds of formulae I and II may be prepared by reaction of a compound of formula III, R²-OH III with a compound of formula IV, and wherein R¹, R² and L¹ have meanings given in the description.
  [FR] La présente invention concerne un procédé d'isolement d'un composé de formule I, [Formule chimique à insérer ici. Voir exemplaire papier] I ou d'un solvate dudit composé, à partir d'un mélange comprenant un composé de formule I et un composé de formule II, [Formule chimique à insérer ici. Voir exemplaire papier] II, le mélange des composés de formule I et de formule II pouvant être préparé par réaction d'un composé de formule III, R²-OH III avec un composé de formule IV, [Formule chimique à insérer ici. Voir exemplaire papier] IV, où R¹, R² et L¹ sont tels que définis dans la description de l'invention.
• Inhibition of Secreted Phospholipase A₂. 4-Glycerol Derivatives of 4,5-Dihydro-3-(4-tetradecyloxybenzyl)-1,2,4-4<i>H</i>-oxadiazol-5-one with Broad Activities
  作者：Mohamed Touaibia、Atimé Djimdé、Fei Cao、Eric Boilard、Sofiane Bezzine、Gérard Lambeau、Catherine Redeuilh、Aazdine Lamouri、France Massicot、François Chau、Chang-Zhi Dong、Françoise Heymans

  DOI：10.1021/jm060082n

  日期：2007.4.1

  Secreted phospholipases A(2) (sPLA(2)s) have been reported to play an important role in various inflammatory conditions and thus represent an attractive therapeutic target. Previous SAR studies from our laboratory have revealed certain important features of our recently discovered specific hGIIA sPLA(2) inhibitors, and we report here the synthesis and biological activities of glycerol-containing derivatives of our lead compound III (Figure 1). Efficient and selective synthesis methods have been developed to make glycerol trisubstituted by different groups on desired positions. In terms of biological activities, the best compounds (A3, A6, and A15) are more active than III (Figure 1), as potent as Me-Indoxam, an sPLA(2)s inhibitor of reference, against hGIIA, hGV, and hGX sPLA(2)s and at least 10 times less active toward the GIB enzymes in two in vitro assay systems. By synthesis of enantiopure (S)-A6, we demonstrated that no important improvement of the inhibitory potency could be achieved by this approach. Furthermore, the results show that the global lipophilicity is likely responsible for the anti-PLA(2) activity and two oxadiazolone moieties seem too big to be accommodated by the active site of the hGIIA enzyme.
• WAGNER G.; HORN H., PHARMAZIE <PHAR-AT>, 1975, 30, NO 6, 353-357
  作者：WAGNER G.、 HORN H.

  DOI：——

  日期：——