3-(4-phenoxyphenoxy)-propan-1-ol | 63402-63-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(4-phenoxyphenoxy)-propan-1-ol
• 英文别名: 3-(4-phenoxyphenoxy)propan-1-ol
• CAS: 63402-63-1
• 化学式: C₁₅H₁₆O₃
• mdl: MFCD11614055
• 分子量: 244.29
• InChiKey: YYVVQNBUGRCBLS-UHFFFAOYSA-N

物化性质

• 沸点：
  380.0±22.0 °C(Predicted)
• 密度：
  1.138±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-phenoxyphenoxy)-propan-1-ol 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 3-(4-phenoxyphenoxy)propyl thiocyanate
  参考文献：
  名称：

  Structure−Activity Relationship of New Growth Inhibitors of Trypanosoma cruzi

  摘要：

  Several drugs bearing the 4-phenoxyphenoxy skeleton and other closely related structures were designed, synthesized, and evaluated as antiproliferative agents against Trypanosoma cruzi, the etiologic agent of Chagas' disease. The new class of drugs was envisioned by modifying the nonpolar 4-phenoxyphenoxy moiety replacing selected aromatic protons by different groups via electrophilic aromatic substitution reactions as well as introducing a sulfur atom at the polar extreme. Of the designed compounds, sulfur-containing derivatives were shown to be potent antireplicative agents against T. cruzi. Among these drugs, 4-phenoxyphenoxyethyl thiocyanate (compound 56) proved to be an extremely active growth inhibitor of the epimastigote forms of T. cruzi and displayed an IC50 of 2.2 mu M. Under the same assay conditions, this drug was much more active than Nifurtimox, one of the drugs currently in clinical use to control this disease. This thiocyanate derivative was also a very active inhibitor against the intracellular form of the parasite at the nanomolar level. Other sulfur derivatives prepared also exhibited very potent antiproliferative action against T. cruzi. The presence of a sulfur atom at the polar extreme for this family of compounds seems to be very important for biological action because this atom was always associated with high inhibition values. 4-Phenoxyphenoxyethyl thiocyanate presents very good prospective not only as a lead drug but also as a potential chemotherapeutic agent.

  DOI：

  10.1021/jm970860z
• 作为产物：
  描述：

  1-(烯丙氧基)-4-苯氧基苯 在 sodium hydroxide 、 双氧水 、 diborane(6) 作用下， 生成 3-(4-phenoxyphenoxy)-propan-1-ol
  参考文献：
  名称：

  设计，合成和抗弗氏锥虫对新型与苯甲威相关的细胞生长抑制剂的评估

  摘要：

  设计并合成了与昆虫生长调节剂苯氧威（1）有关的几种化合物。测试了这些化合物作为克氏锥虫细胞（表皮鞭毛）的生长抑制剂。化合物6，16，18，和22分别为针对非常活跃克氏锥虫使它们要么有前途的良好候选的血库灭菌恰加斯“-disease监视，而化合物11，12，13，和19显示出中等程度的活性。

  DOI：

  10.1002/hlca.19950780513

文献信息

• LTA4 Hydrolase inhibitors
  申请人：G.D. SEARLE & CO.

  公开号：EP1221441A2

  公开（公告）日：2002-07-10

  The present invention provides compounds of the formula Ar1-Q-Ar2-Y-R-Z and pharmaceutically acceptable salts thereof wherein Ar1 and Ar2 are optionally substituted aryl moieties, Z is an optionally substituted nitrogen-containing moiety which may be an acyclic, cyclic or bicyclic amine or an optionally substituted monocyclic or bicyclic nitrogen-containing heteroaromatic moiety; Q is a linking group capable of linking two aryl groups; R is an alkylene moiety; Y is a linking moiety capable of linking an aryl group to an alkylene moiety and wherein Z is bonded to R through a nitrogen atom. The compounds and pharmaceutical compositions of the present invention are useful in the treatment of inflammatory diseases which are mediated by LTB4 production, such as proriasis, ulcerative colitis, IBD and asthma.

  本发明提供了具有公式Ar1-Q-Ar2-Y-R-Z的化合物及其药用可接受的盐，其中Ar1和Ar2是可选地取代的芳基部分，Z是可选地取代的含氮部分，可以是环状、环状或双环状的胺，或可选地取代的单环或双环的含氮杂芳基部分；Q是能够连接两个芳基团的连接基团；R是烷基亚基；Y是能够连接芳基团和烷基亚基的连接基团，并且其中Z通过氮原子与R键合。本发明的化合物和药物组合物在治疗由LTB4产生介导的炎症性疾病中是有用的，例如银屑病、溃疡性结肠炎、炎症性肠病和哮喘。
• Design, Synthesis, and Biological Evaluation of New Growth Inhibitors of <i>Trypanosoma cruzi</i> (Epimastigotes)
  作者：Andrea J. Schvartzapel、Li Zhong、Roberto Docampo、Juan B. Rodriguez、Eduardo G. Gros

  DOI：10.1021/jm9607616

  日期：1997.7.1

  search for new chemotherapeutic agents against Chagas' disease, several drugs structurally related to the insect growth regulator Fenoxycarb and the naturally occurring juvenile hormone of insects were designed, synthesized, and evaluated as antiproliferative agents against the parasite responsible of this disease. Isoprenoid derivatives (compounds 33, 34, 36, and 37) were potent growth inhibitors of Trypanosoma

  作为我们旨在寻找新的针对查加斯病的化学治疗剂的项目的继续，设计，合成并评估了几种与昆虫生长调节剂苯氧威和天然存在的昆虫幼体激素有关的药物，作为抗寄生虫的抗增殖剂对这种疾病负责。类异戊二烯衍生物（化合物33、34、36和37）是克鲁斯锥虫锥鞭毛虫的有效生长抑制剂。另外，考虑到对化合物30观察到的高活性和相关化合物的抑制作用，在这些抑制剂的极性极端处结合的烯丙基醚部分被证明是设计新药的有希望的基团。
• Switching subtype-selectivity: Fragment replacement strategy affords novel class of peroxisome proliferator-activated receptor α/δ (PPARα/δ) dual agonists
  作者：Ryuta Shioi、Shogo Okazaki、Tomomi Noguchi-Yachide、Minoru Ishikawa、Makoto Makishima、Yuichi Hashimoto、Takao Yamaguchi

  DOI：10.1016/j.bmcl.2017.05.037

  日期：2017.7

  contain a carboxylic acid (CA) or thiazolidinedione (TZD) structure (acidic head group) that is essential for activity. We recently discovered non-CA/TZD class PPARα/δ partial agonists, which contain an acetamide moiety and adjacent methyl group, linked to a 1,2,4-oxadiazole ring (“fragment a”). We hypothesized that the acetamide structure might interact with the CA/TZD-binding pocket. To test this

  过氧化物酶体增殖物激活受体（PPAR）是治疗血脂异常，2型糖尿病，心血管疾病，非酒精性脂肪肝和非酒精性脂肪性肝炎的重要药物靶标，并且人们已经在努力开发新的PPAR配体。但是，大多数现有的PPAR配体都含有对活性至关重要的羧酸（CA）或噻唑烷二酮（TZD）结构（酸性头基）。我们最近发现了非CA / TZD类PPARα/δ部分激动剂，其中包含与1，2，4-恶二唑环（“片段a”）相连的乙酰胺部分和相邻的甲基。我们假设乙酰胺结构可能与CA / TZD结合口袋相互作用。为了验证这一想法，我们首先用一种在PPAR激动剂中经常发现的α-烷氧基-CA结构取代了其中一种化合物中的片段a。第二，我们用乙酰胺基片段a取代了一些报道的PPAR激动剂的α-烷氧基-CA头基。通过基于细胞的报告基因分析评估了合成的杂化化合物对PPAR（PPARα，PPARγ和PPARδ）的激动活性。所有杂种分子均表现出PPAR激动活性
• N-substituted azoles and insecticide, arachnicide, and nematocide
  申请人：BASF Aktiengesellschaft

  公开号：US04943585A1

  公开（公告）日：1990-07-24

  ##STR1## N-substituted azoles of the formula I where R.sup.1, R.sup.2, R.sup.3 are each hydrogen, halogen, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.3 -C.sub.10 -cycloalkyl, nitro or cyano, Q is an unsubstituted or substituted azole group of the formula IIa-IIf ##STR2## R.sup.4 to R.sup.15 denoting hydrogen, halogen, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.3 -C.sub.10 -cycloalkyl or aryl which is unsubstituted or mono- di- or trisubstituted by halogen, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl or C.sub.1 -C.sub.4 -haloalkoxy, and X is, in the case of the azole group IIa, --CH.sub.2 -- or -O(CH.sub.2).sub.n --, n being one of the integers 1, 2 or 3, or, in the case of the azole groups IIb-IIf, --OCH.sub.2 --, pesticides containing compounds I as active ingredients, and a process for combating pests.

  式I的N-取代咪唑化合物，其中R.sup.1、R.sup.2、R.sup.3分别为氢、卤素、C.sub.1 -C.sub.8 -烷基、C.sub.1 -C.sub.8 -氧基、C.sub.1 -C.sub.4 -卤代烷基、C.sub.1 -C.sub.4 -卤代氧基、C.sub.3 -C.sub.10 -环烷基、硝基或氰基，Q为式IIa-IIf的未取代或取代咪唑基团 ##STR2## 其中R.sup.4至R.sup.15表示氢、卤素、C.sub.1 -C.sub.8 -烷基、C.sub.1 -C.sub.4 -卤代烷基、C.sub.1 -C.sub.4 -氧基、C.sub.3 -C.sub.10 -环烷基或芳基，该芳基未取代或经卤素、C.sub.1 -C.sub.8 -烷基、C.sub.1 -C.sub.8 -氧基、C.sub.1 -C.sub.4 -卤代烷基或C.sub.1 -C.sub.4 -卤代氧基的单取代、双取代或三取代，X为，在咪唑基IIa的情况下，--CH.sub.2 --或-O(CH.sub.2).sub.n --，n为整数1、2或3之一，或在咪唑基IIb-IIf的情况下，--OCH.sub.2 --，含有化合物I作为活性成分的杀虫剂，以及用于防治害虫的方法。
• N-phenoxyphenoxymethyl-triazoles and a method for controlling pests
  申请人：BASF Aktiengesellschaft

  公开号：US05187182A1

  公开（公告）日：1993-02-16

  N-substituted azoles of the formula I ##STR1## where R.sup.1,R.sup.2, R.sup.3 are each hydrogen, halogen, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.3 -C.sub.10 -cycloalkyl, nitro or cyano, Q is an unsubstituted or substituted azole group of the formulae IIa-IIf ##STR2## R.sup.4 to R.sup.15 denoting hydrogen, halogen, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.3 -C.sub.10 -cycloalkyl or aryl which is unsubstituted or mono-, di- or trisubstituted by halogen, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl or C.sub.1 -C.sub.4 -haloalkoxy, and X is, in the case of the azole group IIa, --CH.sub.2 -- or --O(CH.sub.2).sub.n --, n being one of the integers 1, 2 or 3, or, in the case of the azole groups IIb-IIf, --OCH.sub.2 --, pesticides containing compounds I as active ingredients, and a process for combating pests.

  式I中，N-取代咪唑化合物的结构为：##STR1## 其中，R.sup.1、R.sup.2和R.sup.3分别代表氢、卤素、C.sub.1-C.sub.8烷基、C.sub.1-C.sub.8氧烷基、C.sub.1-C.sub.4卤代烷基、C.sub.1-C.sub.4卤代氧烷基、C.sub.3-C.sub.10环烷基、硝基或氰基；Q代表未取代或取代的咪唑基，其结构为式IIa-IIf：##STR2## 其中，R.sup.4至R.sup.15代表氢、卤素、C.sub.1-C.sub.8烷基、C.sub.1-C.sub.4卤代烷基、C.sub.1-C.sub.4氧烷基、C.sub.3-C.sub.10环烷基或苯基，苯基可以未取代或单、二或三取代，取代基为卤素、C.sub.1-C.sub.8烷基、C.sub.1-C.sub.8氧烷基、C.sub.1-C.sub.4卤代烷基或C.sub.1-C.sub.4卤代氧烷基。X在咪唑基IIa中为--CH.sub.2--或--O(CH.sub.2).sub.n--，其中n为1、2或3的整数，在咪唑基IIb-IIf中为--OCH.sub.2--。含有式I化合物作为活性成分的杀虫剂以及一种用于防治害虫的方法。