1,3-diphenyl-2-(1H-imidazol-1-yl)-propanone | 60851-12-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1,3-diphenyl-2-(1H-imidazol-1-yl)-propanone
• 英文别名: (+/-)-2-(1H-imidazol-1-yl)-1,3-diphenylpropan-1-one；[2-(phenyl)-1-(imidazol-1-yl)ethyl]-(phenyl)-ketone；2-Imidazol-1-yl-1,3-diphenylpropan-1-one
• CAS: 60851-12-9
• 化学式: C₁₈H₁₆N₂O
• 分子量: 276.338
• InChiKey: LUUDTRQITDYXNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-aminooxypentanoic acid hydrochloride 、 1,3-diphenyl-2-(1H-imidazol-1-yl)-propanone 在 吡啶 作用下， 以 重水 为溶剂， 生成 5-[2-Imidazol-1-yl-1,3-diphenyl-prop-(Z)-ylideneaminooxy]-pentanoic acid 、 5-[1-phenyl-2-(imidazol-1-yl)-2-benzylethylidene]aminoxypentanoic acid
  参考文献：
  名称：

  Nucleophilic substitution on α-mesyloxy-O-alkyloximes—I. Enantiospecific synthesis of 2-(imidazol-1-yl)-1,3-diphenylpropan-1-one O-alkyloximes

  摘要：

  An enantiospecific synthesis of (S)- and (R)-(E)-5-[1,3-diphenyl-2-(imidazol-l-yl)propylidene] aminooxypentanoic acids 1 using homochiral phenylalanines as starting material is described. Chiral alpha-hydroxyketones 9 were obtained from alpha-hydroxyacids 7 by Weinreb's ketone synthesis. Imidazole introduction by nucleophilic substitution on mesylate 10 led to 2-(imidazol-1-yl)propan-1-one derivative 3, key intermediate in the synthesis of 1. However, the low configurational stability displayed by compound 3 compromised its use in an enantiospecific synthesis. Homochiral compounds 1 were then obtained by a nucleophilic substitution on alpha-mesyloxy-O-alkyloxymes 14 which were in turn obtained from 9. This nucleophilic substitution on alpha-mesyloxy-O-alkyloxymes was not previously reported either on homochiral compounds or on racemic derivatives. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(96)00505-8
• 作为产物：
  描述：

  N-Methyl-N-methoxy-2-hydroxy-3-phenylpropanamide 在 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.5h， 生成 1,3-diphenyl-2-(1H-imidazol-1-yl)-propanone
  参考文献：
  名称：

  Nucleophilic substitution on α-mesyloxy-O-alkyloximes—I. Enantiospecific synthesis of 2-(imidazol-1-yl)-1,3-diphenylpropan-1-one O-alkyloximes

  摘要：

  An enantiospecific synthesis of (S)- and (R)-(E)-5-[1,3-diphenyl-2-(imidazol-l-yl)propylidene] aminooxypentanoic acids 1 using homochiral phenylalanines as starting material is described. Chiral alpha-hydroxyketones 9 were obtained from alpha-hydroxyacids 7 by Weinreb's ketone synthesis. Imidazole introduction by nucleophilic substitution on mesylate 10 led to 2-(imidazol-1-yl)propan-1-one derivative 3, key intermediate in the synthesis of 1. However, the low configurational stability displayed by compound 3 compromised its use in an enantiospecific synthesis. Homochiral compounds 1 were then obtained by a nucleophilic substitution on alpha-mesyloxy-O-alkyloxymes 14 which were in turn obtained from 9. This nucleophilic substitution on alpha-mesyloxy-O-alkyloxymes was not previously reported either on homochiral compounds or on racemic derivatives. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(96)00505-8

文献信息

• [EN] CHEMICAL COMPOUNDS<br/>[FR] COMPOSES CHIMIQUES
  申请人：ASTRAZENECA AB

  公开号：WO2004011410A1

  公开（公告）日：2004-02-05

  Compounds of formula (I):wherein variable groups are as defined within; for use in the inhibition of 11βHSD1 are described.

  式(I)的化合物：其中变量基团如定义内；用于抑制11βHSD1。
• Agents Combining Thromboxane Receptor Antagonism with Thromboxane Synthase Inhibition: [[[2-(1H-Imidazol-1-yl)ethylidene]amino]oxy]alkanoic Acids
  作者：Paolo Cozzi、Antonio Giordani、Maria Menichincheri、Antonio Pillan、Vittorio Pinciroli、Arsenia Rossi、Roberto Tonani、Daniele Volpi、Monica Tamburin

  DOI：10.1021/jm00047a016

  日期：1994.10

  A new class of compounds combining thromboxane-A2 (TxA2) receptor antagonism and thromboxane synthase inhibition is described. A first series of (E)- and (Z)-[[[2-(1H-imidazol-1-yl)ethylidene]amino]oxy]pentanoic acids showed relevant thromboxane synthase inhibition associated with weak TxA2 receptor antagonism, while a series of (+/-)-(E)-[[[2-(1H-imidazol-1-yl)-3-phenylpropylidene]amino]oxy] pentanoic

  描述了结合血栓烷-A2（TxA2）受体拮抗作用和血栓烷合酶抑制作用的一类新化合物。第一个系列（E）-和（Z）-[[[[2-（1H-咪唑-1-基）亚乙基]氨基]氧基]戊酸显示相关的血栓烷合酶抑制与弱TxA2受体拮抗作用有关，而一系列前者在结构上衍生自（+/-）-（E）-[[[[2-（1H-咪唑-1-基）-3-苯基亚丙基]氨基]氧基]戊酸的戊酸显示有效且均衡的双重活动。讨论了重要的单一活动和双重活动的结构要求。后一个系列的两个紧密同源物，（+/-）-（E）-5-[[[[1-环己基-2-（1H-咪唑-1-基）-3-苯基亚丙基]氨基]氧基]戊酸23c及其对氟苯基类似物23m在凝结期间抑制大鼠全血中TxB2的产生，IC50为0.06和0。37 microM拮抗[3H] SQ 29548与洗涤的人血小板的结合，IC50分别为0.08和0.02 microM。选择这两种化合物进行进一步的药理评估，结果显
• Ketones
  申请人：Barton John Peter

  公开号：US20050272036A1

  公开（公告）日：2005-12-08

  Compounds of formula (I): wherein variable groups are as defined within; for use in the inhibition of 11βHSD1 are described.

  描述了式(I)的化合物：其中变量基团如定义的那样；用于抑制11βHSD1。
• KETONES
  申请人：AstraZeneca AB

  公开号：EP1549600A1

  公开（公告）日：2005-07-06
• Nucleophilic substitution on α-mesyloxy-O-alkyloximes—I. Enantiospecific synthesis of 2-(imidazol-1-yl)-1,3-diphenylpropan-1-one O-alkyloximes
  作者：Antonio Giordani、Alberto Carera、Vittorio Pinciroli、Paolo Cozzi

  DOI：10.1016/s0957-4166(96)00505-8

  日期：1997.1

  An enantiospecific synthesis of (S)- and (R)-(E)-5-[1,3-diphenyl-2-(imidazol-l-yl)propylidene] aminooxypentanoic acids 1 using homochiral phenylalanines as starting material is described. Chiral alpha-hydroxyketones 9 were obtained from alpha-hydroxyacids 7 by Weinreb's ketone synthesis. Imidazole introduction by nucleophilic substitution on mesylate 10 led to 2-(imidazol-1-yl)propan-1-one derivative 3, key intermediate in the synthesis of 1. However, the low configurational stability displayed by compound 3 compromised its use in an enantiospecific synthesis. Homochiral compounds 1 were then obtained by a nucleophilic substitution on alpha-mesyloxy-O-alkyloxymes 14 which were in turn obtained from 9. This nucleophilic substitution on alpha-mesyloxy-O-alkyloxymes was not previously reported either on homochiral compounds or on racemic derivatives. (C) 1997 Elsevier Science Ltd.