1-<5-phenyl-2-(phenylmethoxy)phenyl>ethanone | 56926-48-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-<5-phenyl-2-(phenylmethoxy)phenyl>ethanone
• 英文别名: 2-benzyloxy-5-phenylacetophenone；2-Benzyloxy-5-phenylacetophenon；1-(4-benzyloxy-biphenyl-3-yl)-ethanone；1-(4-Benzyloxy-biphenyl-3-yl)-aethanon；Ethanone, 1-[4-(phenylmethoxy)[1,1'-biphenyl]-3-yl]-；1-(5-phenyl-2-phenylmethoxyphenyl)ethanone
• CAS: 56926-48-8
• 化学式: C₂₁H₁₈O₂
• 分子量: 302.373
• InChiKey: UDQSXHYANJXCPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-<5-phenyl-2-(phenylmethoxy)phenyl>ethanone 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 2-hydroxy-5-phenylacetophenone
  参考文献：
  名称：

  Synthesis of ethyl 6-substituted-chroman- and -chromone-2-carboxylates. Comparative structure-activity study employing the 6-phenyl and phenoxy analogs in the triton hyperlipidemic rat model

  摘要：

  To explore the effect of lipophilicity on antilipidemic activity in the Triton WR-1339 induced hyperlipidemic rat model we synthesized the 6-cyclohexyl, phenyl, and phenoxy analogs of ethyl chroman-2-carboxylate. Results obtained were analyzed in light of the biological activity observed for the 6-chloro-substituted and unsubstituted chromans, the 6-chlorochroman-4-one ester, and the 6-chloro-, phenyl-, and phenoxychromone esters. The suggestion is made that chromones likely exert their antilipidemic effects by a somewhat different set of mechanisms than do the chromans and clofibrate. Whereas the 6-chlorochromanone ester is inactive, the 6-chlorochromone ester is active in both normal and hyperlipidemic Sprague-Dawley rats. The major differential effect was observed for ethyl 6-cyclohexylchroman-2-carboxylate which did not lower cholesterol levels but returned triglyceride levels to normal in hyperlipidemic rats.

  DOI：

  10.1021/jm00243a015
• 作为产物：
  描述：

  4-乙酰氧基联苯 在 sodium hydroxide 、 三氯化铝 、 四丁基溴化铵 作用下， 以 二氯甲烷 、 邻二氯苯 为溶剂， 反应 48.0h， 生成 1-<5-phenyl-2-(phenylmethoxy)phenyl>ethanone
  参考文献：
  名称：

  WB4101-Related Compounds:  New, Subtype-Selective α₁-Adrenoreceptor Antagonists (or Inverse Agonists?)

  摘要：

  Our previous structure-affinity relationship study had considered the enantiomers of the naphthodioxane, tetrahydronaphthodioxane, and 2-methoxy-1-naphthoxy analogues ( compounds 1, 3, and 2, respectively) of 2-(2,6-dimethoxyphenoxyethylaminomethyl)-1,4-benzodioxane, the well-known alpha(1)-adrenoceptor (alpha(1)-AR) antagonist WB4101, showing that such modifications significantly modulate the affinity and selectivity profile for alpha(1)-AR subtypes and 5-HT1A receptor. Here, we extend investigations to antagonist activity enclosing new enantiomeric pairs, namely those of the methoxytetrahydronaphthoxy and methoxybiphenyloxy WB4101 analogues (4 and 5-7, respectively) and of a double- modified WB4101 derivative ( 8) resulting from hybridization between 2 and 3. We found that (S)-2 is a very potent (pA(2) 10.68) and moderately selective alpha(1D)-AR antagonist and the hybrid (S)-8 is a potent (pA(2) 7.98) and highly selective alpha(1A)-AR antagonist. Both of these compounds and (S)-WB4101 seem to act as inverse agonists in a vascular model. The results, which generally validate the logic we followed in designing these eight compounds, are acceptably rationalized by comparative SAR analysis of binding and functional affinities.

  DOI：

  10.1021/jm060358r

文献信息

• Synthetic aci-reductones. 3,4-Dihydroxy-2H-1-benzopyran-2-ones and their cis- and trans-4a,5,6,7,8,8a-hexahydro diastereomers. Antiaggregatory, antilipidemic, and redox properties compared to the 4-substituted 2-hydroxytetronic acids
  作者：Donald T. Witiak、Sung K. Kim、Ashok K. Tehim、Kent D. Sternitzke、Richard L. McCreery、Sung U. Kim、Dennis R. Feller、Karl J. Romstedt、Vaijinath S. Kamanna、Howard A. I. Newman

  DOI：10.1021/jm00402a032

  日期：1988.7

  platelets. Results are compared to aci-reductones belonging to the 4-aryl- and 4-spiroalkyl-2-hydroxytetronic acid systems (4,5a,b). Redox potentials for all aci-reductones were determined with cyclic voltammetry. It would appear that the 4-aryl-2-hydroxytetronic acids represent leads for further study as antiatherosclerotic drugs owing to their favorable antilipidemic and antiaggregatory properties whereas

  合成属于6-或7-单或双取代的3,4-二羟基-2H-1-苯并吡喃-2-酮（6-10）及其顺式和反式aci还原酮的合成方法描述了-4a，5、6、7、8、8a-六氢非对映异构体（11、12）。使用Meldrum's synthon（2,2-二甲基-1,3-二恶烷-4,6-dione，49）可方便地制备六氢苯并吡喃酮aci-还原酮。在胆固醇喂养的大鼠模型中评估了其中某些物质的抗血脂活性，并研究了所有类似物抑制人血小板聚集的能力。将结果与属于4-芳基-和4-螺烷基-2-羟基tetronic酸体系的aci-还原酮进行比较（4,5a，b）。用循环伏安法测定所有aci还原酮的氧化还原电位。
• Aralkyl ethers of acyl-phenols
  申请人：DOW CHEMICAL CO

  公开号：US02109458A1

  公开（公告）日：1938-03-01
• WITIAK D. T.; HEILMAN W. P.; SANKARAPPA S. K.; CAVESTRI R. C.; NEWMAN H. +, J. MED. CHEM. <JMCM-AR>, 1975, 18, NO 9, 934-942
  作者：WITIAK D. T.、 HEILMAN W. P.、 SANKARAPPA S. K.、 CAVESTRI R. C.、 NEWMAN H. +

  DOI：——

  日期：——
• WB4101-Related Compounds:  New, Subtype-Selective α₁-Adrenoreceptor Antagonists (or Inverse Agonists?)
  作者：Marco Pallavicini、Roberta Budriesi、Laura Fumagalli、Pierfranco Ioan、Alberto Chiarini、Cristiano Bolchi、Maria Paola Ugenti、Simona Colleoni、Marco Gobbi、Ermanno Valoti

  DOI：10.1021/jm060358r

  日期：2006.11.30

  Our previous structure-affinity relationship study had considered the enantiomers of the naphthodioxane, tetrahydronaphthodioxane, and 2-methoxy-1-naphthoxy analogues ( compounds 1, 3, and 2, respectively) of 2-(2,6-dimethoxyphenoxyethylaminomethyl)-1,4-benzodioxane, the well-known alpha(1)-adrenoceptor (alpha(1)-AR) antagonist WB4101, showing that such modifications significantly modulate the affinity and selectivity profile for alpha(1)-AR subtypes and 5-HT1A receptor. Here, we extend investigations to antagonist activity enclosing new enantiomeric pairs, namely those of the methoxytetrahydronaphthoxy and methoxybiphenyloxy WB4101 analogues (4 and 5-7, respectively) and of a double- modified WB4101 derivative ( 8) resulting from hybridization between 2 and 3. We found that (S)-2 is a very potent (pA(2) 10.68) and moderately selective alpha(1D)-AR antagonist and the hybrid (S)-8 is a potent (pA(2) 7.98) and highly selective alpha(1A)-AR antagonist. Both of these compounds and (S)-WB4101 seem to act as inverse agonists in a vascular model. The results, which generally validate the logic we followed in designing these eight compounds, are acceptably rationalized by comparative SAR analysis of binding and functional affinities.
• Synthesis of ethyl 6-substituted-chroman- and -chromone-2-carboxylates. Comparative structure-activity study employing the 6-phenyl and phenoxy analogs in the triton hyperlipidemic rat model
  作者：Donald T. Witiak、William P. Heilman、Shankar K. Sankarappa、Richard C. Cavestri、Howard A. I. Newman

  DOI：10.1021/jm00243a015

  日期：1975.9

  To explore the effect of lipophilicity on antilipidemic activity in the Triton WR-1339 induced hyperlipidemic rat model we synthesized the 6-cyclohexyl, phenyl, and phenoxy analogs of ethyl chroman-2-carboxylate. Results obtained were analyzed in light of the biological activity observed for the 6-chloro-substituted and unsubstituted chromans, the 6-chlorochroman-4-one ester, and the 6-chloro-, phenyl-, and phenoxychromone esters. The suggestion is made that chromones likely exert their antilipidemic effects by a somewhat different set of mechanisms than do the chromans and clofibrate. Whereas the 6-chlorochromanone ester is inactive, the 6-chlorochromone ester is active in both normal and hyperlipidemic Sprague-Dawley rats. The major differential effect was observed for ethyl 6-cyclohexylchroman-2-carboxylate which did not lower cholesterol levels but returned triglyceride levels to normal in hyperlipidemic rats.