2-methyl-2-[4-(2-methylpropyl)phenyl]-1,3-benzodioxolane-5-carboxylic acid | 181297-59-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 2-methyl-2-[4-(2-methylpropyl)phenyl]-1,3-benzodioxolane-5-carboxylic acid
• 英文别名: 2-Methyl-2-[4-(2-methylpropyl)phenyl]-1,3-benzodioxole-5-carboxylic acid
• CAS: 181297-59-6
• 化学式: C₁₉H₂₀O₄
• 分子量: 312.365
• InChiKey: SMHUIHXBNYCWHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methyl-2-[4-(2-methylpropyl)phenyl]-1,3-benzodioxolane-5-carboxylic acid 在 盐酸 、 甲基碘化镁 、 氯化亚砜 、 (-)-α-methylbenzylamine 、 potassium carbonate 作用下， 以 吡啶 、 甲苯 、 丁酮 为溶剂， 生成
  参考文献：
  名称：

  The development of non-steroidal dual inhibitors of both human 5α-reductase isozymes

  摘要：

  The design, synthesis and biological properties of homochiral non-steroidal inhibitors of both isozymes of human 5 alpha-reductase are described. The o-hydroxy aniline moiety of the initial lead (1) can be replaced by a 3-acyl indole isostere, whilst the minimum energy conformation of the benzyl ether in the potent inhibitor (3) is mimicked by the conformationally locked benzodioxolane system in the potent non-steroidal inhibitor (7). Pharmacokinetics and oral efficacy in a rat model of BPH are presented for (3) and (7). Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00261-2
• 作为产物：
  描述：

  1-(1,1-二甲氧基乙基)-4-异丁基苯 在 sodium hydroxide 、 甲磺酸异丙酯 作用下， 以 水 为溶剂， 生成 2-methyl-2-[4-(2-methylpropyl)phenyl]-1,3-benzodioxolane-5-carboxylic acid
  参考文献：
  名称：

  The development of non-steroidal dual inhibitors of both human 5α-reductase isozymes

  摘要：

  The design, synthesis and biological properties of homochiral non-steroidal inhibitors of both isozymes of human 5 alpha-reductase are described. The o-hydroxy aniline moiety of the initial lead (1) can be replaced by a 3-acyl indole isostere, whilst the minimum energy conformation of the benzyl ether in the potent inhibitor (3) is mimicked by the conformationally locked benzodioxolane system in the potent non-steroidal inhibitor (7). Pharmacokinetics and oral efficacy in a rat model of BPH are presented for (3) and (7). Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00261-2

文献信息

• INDOLE DERIVATIVES AS STEROID 5 ALPHA-REDUCTASE INHIBITORS
  申请人：Pfizer Limited

  公开号：EP0628040A1

  公开（公告）日：1994-12-14
• ステロイド５α−レダクタ―ゼ阻害物質としてのインド―ル誘導体
  申请人：PFIZER

  公开号：JP2540016B2

  公开（公告）日：1996-10-02
• US5767139A
  申请人：——

  公开号：US5767139A

  公开（公告）日：1998-06-16
• [EN] INDOLE DERIVATIVES AS STEROID 5 ALPHA-REDUCTASE INHIBITORS
  申请人：PFIZER LIMITED

  公开号：WO1993017014A1

  公开（公告）日：1993-09-02

  (EN) The present invention provides compounds of formula (I) and the pharmaceutically acceptable salts thereof, wherein X is O, NH, N(C1-C4 alkyl), direct link, C1-C4 alkylene, C2-C4 alkenylene or C2-C4 alkynylene, said alkylene, alkenylene and alkynylene being optionally substituted by C1-C4 alkyl or aryl; Y is methylene, C2-C6 alkylene optionally interrupted by O, C2-C6 alkenylene or C2-C6 alkynylene, all of which may be optionally substituted by C1-C6 alkyl, or is a group of formula (II) wherein m and n are each independently selected from O and an integer of from 1 to 5, with the proviso that the sum of m and n is not greater than 5, and p is an integer of from 2 to 6; R is H, OH, halo, C1-C4 alkyl or C1-C4 alkoxy; R1, R2, R3 and R4 are each independently selected from H, C1-C4 alkyl, C1-C4 alkoxy, OH, halo, -CF3, -CO2(C1-C4 alkyl), -CONH2, -CONH(C1-C4 alkyl) and -CON(C1-C4 alkyl)2; R5 is -COOH, -COOR7, -CONR8R9 or tetrazol-5-yl; and R6 is (III) or (IV), together with pharmaceutically compositions containing, uses of, processes for the preparation of and intermediates used in the preparation of, such compounds.(FR) L'invention concerne des composés de la formule (I) et leurs sels acceptables sur le plan pharmaceutique. Dans cette formule: X est O, NH, N(C1-C4)alkyle, une liaison directe, un (C1-C4)alkylène, un (C2-C4)alcénylène ou un (C2-C4)alcynylène, ledit alkylène, alcénylène ou alcynylène étant le cas échéant substitué avec un (C1-C4)alkyle ou un aryle; Y est un méthylène, un (C2-C6)alkylène le cas échéant coupé par un O, un (C2-C6)alcénylène ou un (C2-C6)alcynylène, qui peuvent tous être le cas échéant substitués avec un groupe (C1-C6)alkyle, ou encore un groupe de la formule (II) dans laquelle m et n sont choisis chacun d'une manière indépendante parmi O et les nombres entiers de 1 à 5, avec comme condition que la somme de m et de n ne soit pas supérieure à 5 et que p soit un nombre entier entre 2 et 6; R est H, OH, halo, un (C1-C4)alkyle ou un (C1-C4)alcoxy; R1, R2, R3 et R4 sont chacun d'une manière indépendante choisis parmi H, (C1-C4)alkyle, (C1-C4)alcoxy, OH, halo, -CF3, -CO2(C1-C4)alkyle, -CONH2, -CONH(C1-C4)alkyle et -CON[(C1-C4)alkyle]2; R5 est -COOH, -COOR7, -CONR8R9 ou tétrazol-5-yl; et R6 est formule (III) ou formule (IV). L'invention concerne également les compositions pharmaceutiques contenant ces composés, les procédés de leur préparation et les intermédiaires utilisés dans leur préparation.
• The development of non-steroidal dual inhibitors of both human 5α-reductase isozymes
  作者：J. Blagg、S.A. Ballard、K. Cooper、P.W. Finn、P.S. Johnson、F. MacIntyre、G.N. Maw、P.L. Spargo

  DOI：10.1016/s0960-894x(96)00261-2

  日期：1996.7

  The design, synthesis and biological properties of homochiral non-steroidal inhibitors of both isozymes of human 5 alpha-reductase are described. The o-hydroxy aniline moiety of the initial lead (1) can be replaced by a 3-acyl indole isostere, whilst the minimum energy conformation of the benzyl ether in the potent inhibitor (3) is mimicked by the conformationally locked benzodioxolane system in the potent non-steroidal inhibitor (7). Pharmacokinetics and oral efficacy in a rat model of BPH are presented for (3) and (7). Copyright (C) 1996 Elsevier Science Ltd