Furan-2-ylmethyl-(4-phenoxy-benzyl)-amine | 169943-51-5

• 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: Furan-2-ylmethyl-(4-phenoxy-benzyl)-amine
• 英文别名: N-(furan-2-ylmethyl)-1-(4-phenoxyphenyl)methanamine
• CAS: 169943-51-5
• 化学式: C₁₈H₁₇NO₂
• 分子量: 279.338
• InChiKey: ICLQZIFLDRIGNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  34.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4,6-三甲基苯基异氰酸酯 、 Furan-2-ylmethyl-(4-phenoxy-benzyl)-amine 以 二氯甲烷 为溶剂， 以98%的产率得到1-Furan-2-ylmethyl-1-(4-phenoxy-benzyl)-3-(2,4,6-trimethyl-phenyl)-urea
  参考文献：
  名称：

  Inhibitors of acyl-CoA: cholesterol O-acyltransferase (ACAT). Part 1: Identification and structure-activity relationships of a novel series of substituted N-alkyl-N-biphenylylmethyl-N′-arylureas

  摘要：

  A series of N-alkyl-N-biphenylylmethyl-N'-arylurea and related derivatives represented by 1 have been prepared and evaluated for their ability to inhibit acyl-CoA:cholesterol O-acyltransferase in vitro and to lower plasma cholesterol levels in cholesterol-fed rats in vivo. Linking of two phenyl groups via oxygen and introduction of fluorine at appropriate positions on the biphenyl moiety improved in vitro and in vivo activity, From this series of analogs, compound 40 (FR179254), which had potent in vitro potency (rabbit intestinal microsomes IC50 = 25 nM), showed excellent plasma cholesterol-lowering activity when administered via the diet (ED50 = 0.045 mg/kg). However, the hypocholesterolemic effect of this compound was moderate when dosed by oral gavage in PEG400 as a vehicle (ED50 = 5.3 mg/kg). Modification of the N'-aryl moiety led to the identification of compound 50 (FR182980) which was efficacious in both dosing models (ED50 = 0.034 mg/kg and 0.11 mg/kg, respectively). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(97)10009-8
• 作为产物：
  描述：

  4-苯氧基苯甲醛 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 Furan-2-ylmethyl-(4-phenoxy-benzyl)-amine
  参考文献：
  名称：

  Inhibitors of acyl-CoA: cholesterol O-acyltransferase (ACAT). Part 1: Identification and structure-activity relationships of a novel series of substituted N-alkyl-N-biphenylylmethyl-N′-arylureas

  摘要：

  A series of N-alkyl-N-biphenylylmethyl-N'-arylurea and related derivatives represented by 1 have been prepared and evaluated for their ability to inhibit acyl-CoA:cholesterol O-acyltransferase in vitro and to lower plasma cholesterol levels in cholesterol-fed rats in vivo. Linking of two phenyl groups via oxygen and introduction of fluorine at appropriate positions on the biphenyl moiety improved in vitro and in vivo activity, From this series of analogs, compound 40 (FR179254), which had potent in vitro potency (rabbit intestinal microsomes IC50 = 25 nM), showed excellent plasma cholesterol-lowering activity when administered via the diet (ED50 = 0.045 mg/kg). However, the hypocholesterolemic effect of this compound was moderate when dosed by oral gavage in PEG400 as a vehicle (ED50 = 5.3 mg/kg). Modification of the N'-aryl moiety led to the identification of compound 50 (FR182980) which was efficacious in both dosing models (ED50 = 0.034 mg/kg and 0.11 mg/kg, respectively). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(97)10009-8

文献信息

• CYCLOBUTANE DERIVATIVES AS INHIBITORS OF SQUALENE SYNTHETASE AND PROTEIN FARNESYLTRANSFERASE
  申请人：Abbott Laboratories

  公开号：EP0677039A1

  公开（公告）日：1995-10-18
• UREA DERIVATIVES AND THEIR USE AS ACAT-INHIBITORS
  申请人：FUJISAWA PHARMACEUTICAL CO., LTD.

  公开号：EP0784612A1

  公开（公告）日：1997-07-23
• US5631401A
  申请人：——

  公开号：US5631401A

  公开（公告）日：1997-05-20
• US5783593A
  申请人：——

  公开号：US5783593A

  公开（公告）日：1998-07-21
• [EN] CYCLOBUTANE DERIVATIVES AS INHIBITORS OF SQUALENE SYNTHETASE AND PROTEIN FARNESYLTRANSFERASE<br/>[FR] DERIVES DE CYCLOBUTANE UTILISES EN TANT QU'INHIBITEURS DE LA SQUALENE-SYNTHETASE ET DE LA FARNESYLTRANSFERASE PROTEIQUE
  申请人：ABBOTT LABORATORIES

  公开号：WO1995012572A1

  公开（公告）日：1995-05-11

  (EN) The present invention provides a compound of formula (I) processes for the preparation of the compounds of the invention in addition to intermediates useful in these processes, a pharmaceutical composition, and a method of treating disorders resulting from an excess of cholesterol or cancer or a fungal infection.(FR) L'invention concerne un composé de formule (I) ainsi que ses procédés de préparation, des intermédiaires utiles dans ces procédés, une composition pharmaceutique, et un procédé de traitement de troubles résultant d'un excédent de cholestérol, d'un cancer ou d'une infection fongique.