1,3-Bis(p-cyanophenoxy)propan-2-ol | 917895-14-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,3-Bis(p-cyanophenoxy)propan-2-ol
• 英文别名: 1,3-bis(4-cyanophenoxy)propan-2-ol；4,4'-[(2-Hydroxypropane-1,3-diyl)bis(oxy)]dibenzonitrile；4-[3-(4-cyanophenoxy)-2-hydroxypropoxy]benzonitrile
• CAS: 917895-14-8
• 化学式: C₁₇H₁₄N₂O₃
• 分子量: 294.31
• InChiKey: OOBLIKSYHAHWGP-UHFFFAOYSA-N

物化性质

• 熔点：
  120 °C
• 沸点：
  542.3±40.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  86.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,3-Bis(p-cyanophenoxy)propan-2-ol 在 吡啶 、 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 1,3-bis(4-cyanophenoxy)propan-2-yl azide
  参考文献：
  名称：

  1,3-双（芳氧基）丙-2-胺的合成及抗衰老活性

  摘要：

  我们在这里描述了从表氯醇四个简单步骤制备的1,3-双（芳氧基）丙-2-胺的抗衰老活性。在所评估的化合物中，三个（4o，4q和4r）显示出对亚马逊利什曼原虫前鞭毛体形式的相当大的活​​性，IC 50值低于10 µM。我们还分析了环取代基的性质和位置对活性的影响。两种胺（4m和4o）在处理被亚马逊菌感染的巨噬细胞时表现出出色的特性，在测试浓度下将寄生虫负担降低了95％以上。

  DOI：

  10.1007/s00044-017-1805-1
• 作为产物：
  描述：

  1,3-二溴-2-丙醇 、 4-羟基苯甲腈 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 1,3-Bis(p-cyanophenoxy)propan-2-ol
  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

• 1,3-Bis(aryloxy)propan-2-ols as potential antileishmanial agents
  作者：Stefânia N. Lavorato、Mariana C. Duarte、Daniela P. Lage、Carlos A. P. Tavares、Eduardo A. F. Coelho、Ricardo J. Alves

  DOI：10.1111/cbdd.13024

  日期：2017.11

  We describe herein the synthesis and antileishmanial activity of 1,3-bis(aryloxy)propan-2-ols. Five compounds (2, 3, 13, 17, and 18) exhibited an effective antileishmanial activity against stationary promastigote forms of Leishmania amazonensis (IC50 < 15.0 μm), and an influence of compound lipophilicity on activity was suggested. Most of the compounds were poorly selective, as they showed toxicity

  我们在本文中描述了1，3-双（芳氧基）丙-2-醇的合成和抗衰老活性。五个化合物（2、3、13、17和18）对亚马逊利什曼原虫的固定前鞭毛体形式（IC50 <15.0μm）表现出有效的抗前鞭毛虫活性，并提出了化合物亲脂性对活性的影响。大多数化合物的选择性较差，因为它们对鼠类巨噬细胞显示毒性，只有17和18具有良好的选择指数（SI≥10.0）。选择了另外五种活性化合物（2、3、13、17和18）来治疗被感染的巨噬细胞，所有这些化合物都能够减少80％以上的内在寄生虫以及数量的减少。在至少一种测试浓度下，被感染的巨噬细胞数量增加了70％以上。共，
• [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.
• Synthesis and antileishmanial activity of 1,3-bis(aryloxy)propan-2-amines
  作者：Stefânia N. Lavorato、Mariana C. Duarte、Daniela P. Lage、Carlos A. P. Tavares、Eduardo A. F. Coelho、Ricardo J. Alves

  DOI：10.1007/s00044-017-1805-1

  日期：2017.5

  We describe herein the antileishmanial activity of 1,3-bis(aryloxy)propan-2-amines, prepared in four simple steps from epichlorohydrin. Among the evaluated compounds, three (4o, 4q, and 4r) displayed considerable activity against Leishmania amazonensis promastigote forms, with IC50 values below 10 µM. We also analyzed the effects of the nature and the position of ring substituent on activity. Two amines

  我们在这里描述了从表氯醇四个简单步骤制备的1,3-双（芳氧基）丙-2-胺的抗衰老活性。在所评估的化合物中，三个（4o，4q和4r）显示出对亚马逊利什曼原虫前鞭毛体形式的相当大的活​​性，IC 50值低于10 µM。我们还分析了环取代基的性质和位置对活性的影响。两种胺（4m和4o）在处理被亚马逊菌感染的巨噬细胞时表现出出色的特性，在测试浓度下将寄生虫负担降低了95％以上。