Ethyl 4-[3-(3,4-dihydroxybenzoyl)indol-1-yl]butanoate | 152360-09-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: Ethyl 4-[3-(3,4-dihydroxybenzoyl)indol-1-yl]butanoate
• CAS: 152360-09-3
• 化学式: C₂₁H₂₁NO₅
• 分子量: 367.401
• InChiKey: ATNCNLYQHYCDFO-UHFFFAOYSA-N

物化性质

• 沸点：
  610.5±55.0 °C(predicted)
• 密度：
  1.26±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  88.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl 4-[3-(3,4-dihydroxybenzoyl)indol-1-yl]butanoate 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Dual-acting agents with α1-adrenoceptor antagonistic and steroid 5α-reductase inhibitory activities. Synthesis and evaluation of arylpiperazine derivatives

  摘要：

  A series of arylpiperazine derivatives were prepared and evaluated for their alpha(1)-adrenoceptor antagonistic activities and 5 alpha-reductase inhibitory activities. SAR study led to the identification of the potent dual-acting compound 2f, which had a pA(2) value of 7.5 for alpha(1)-adrenoceptor antagonism and an IC50 value of 1.5 nM for 5 alpha-reductase inhibition. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00230-9
• 作为产物：
  描述：

  ethyl 4-[3-([2,2-diphenyl-1,3-benzodioxolan-5-yl]carbonyl)indol-1-yl]butanoate 以 溶剂黄146 为溶剂， 反应 5.0h， 生成 Ethyl 4-[3-(3,4-dihydroxybenzoyl)indol-1-yl]butanoate
  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 derivative for treating overproduction of dihydrotestosterone
  申请人：Zeria Pharmaceutical Co., Ltd.

  公开号：US05760040A1

  公开（公告）日：1998-06-02

  The present invention relates to an indole derivative represented by formula (1) or a salt thereof, and a pharmaceutical containing the derivative or the salt: ##STR1## wherein R.sup.1 represents lower alkyl; R.sup.2 represents hydrogen or phenyl which may be substituted by at least one lower alkyl, lower alkoxy or a halogen atom; R.sup.3 represents hydrogen, lower alkyl, lower alkoxy, or phenylalkyloxy which may be substituted by halogen or lower alkyl; R.sup.4 represents hydrogen, lower alkyl or lower alkoxy; R.sup.5 represents hydrogen or lower alkyl; and n represents an integer of 1 to 5. This compound has the effects of both blocking .alpha..sub.1 -adrenergic receptors and inhibiting testosterone 5.alpha.-reductases, and is useful as a remedy and/or a preventive for diseases caused by dihydrotestosterone overproduction, such as prostatic hypertrophy, and diseases accompanying the same, such as urination disorder, male pattern alopecia, acne, and so forth.

  本发明涉及一种由公式（1）表示的吲哚衍生物或其盐，以及含有该衍生物或盐的制药物：##STR1## 其中R.sup.1代表较低的烷基；R.sup.2代表氢或苯基，该苯基可以被至少一个较低的烷基，较低的烷氧基或卤素原子取代；R.sup.3代表氢，较低的烷基，较低的烷氧基或苯基烷氧基，该苯基烷氧基可以被卤素或较低的烷基取代；R.sup.4代表氢，较低的烷基或较低的烷氧基；R.sup.5代表氢或较低的烷基；n代表1至5的整数。该化合物具有阻断α.sub.1-肾上腺素受体和抑制睾酮5α-还原酶的作用，并且可用作治疗和/或预防由二氢睾酮过度产生引起的疾病，例如前列腺肥大以及伴随其发生的疾病，例如排尿障碍，男性型脱发，痤疮等。
• INDOLE DERIVATIVE AND MEDICINE CONTAINING THE SAME
  申请人：ZERIA PHARMACEUTICAL CO., LTD.

  公开号：EP0753511A1

  公开（公告）日：1997-01-15

  The present invention relates to an indole derivative represented by formula (1) or a salt thereof, and a pharmaceutical containing the derivative or the salt: [wherein R1 represents lower alkyl; R2 represents hydrogen or phenyl which may be substituted by at least one lower alkyl, lower alkoxy or a halogen atom; R3 represents hydrogen, lower alkyl, lower alkoxy, or phenylalkyloxy which may be substituted by halogen or lower alkyl; R4 represents hydrogen, lower alkyl or lower alkoxy; R5 represents hydrogen or lower alkyl; and n represents an integer of 1 to 5]. This compound has the effects of both blocking α1-adrenergic receptors and inhibiting testosterone 5α-reductases, and is useful as a remedy and/or a preventive for diseases caused by dihydrotestosterone overproduction, such as prostatic hypertrophy, and diseases accompanying the same, such as urination disorder, male pattern alopecia, acne, and so forth.

  本发明涉及一种由式（1）表示的吲哚衍生物或其盐，以及一种含有该衍生物或该盐的药物： [其中 R1 代表低级烷基；R2 代表氢或苯基，可被至少一个低级烷基、低级烷氧基或卤素原子取代；R3 代表氢、低级烷基、低级烷氧基或苯基烷氧基，可被卤素或低级烷基取代；R4 代表氢、低级烷基或低级烷氧基；R5 代表氢或低级烷基；n 代表 1 至 5 的整数]。该化合物具有阻断α1-肾上腺素能受体和抑制睾酮 5α-还原酶的作用，可用于治疗和/或预防双氢睾酮过度分泌引起的疾病，如前列腺肥大，以及伴随前列腺肥大的疾病，如排尿障碍、男性型脱发、痤疮等。
• 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
• 4-INDOL-1-YL BUTYRIC ACID DERIVATIVES, THEIR PREPARATION AND THEIR USE AS INHIBITORS OF ALPHA1-ADRENERGIC RECEPTORS AND TESTOSTERONE 5ALPHA-REDUCTASES
  申请人：ZERIA PHARMACEUTICAL CO., LTD.

  公开号：EP0753511B1

  公开（公告）日：2001-07-11
• US5767139A
  申请人：——

  公开号：US5767139A

  公开（公告）日：1998-06-16