(E)-3-[1-(4-Butoxy-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acrylic acid

• 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: (E)-3-[1-(4-Butoxy-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acrylic acid
• 英文别名: (E)-3-[1-(4-butoxybenzoyl)-5-methoxy-2-methylindol-3-yl]prop-2-enoic acid
• 化学式: C₂₄H₂₅NO₅
• 分子量: 407.466
• InChiKey: AVPLBFNMFHRNDX-ACCUITESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  77.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-甲氧基-2-甲基吲哚 在 sodium hydroxide 、 正丁基锂 、 三氯氧磷 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 正己烷 、 苯 为溶剂， 反应 59.5h， 生成 (E)-3-[1-(4-Butoxy-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acrylic acid
  参考文献：
  名称：

  Development of a prostaglandin D2 receptor antagonist: discovery of a new chemical lead

  摘要：

  A series of N-(p-alkoxy)benzoyl-5-methoxy-2-methylindole-3-acetic acids and N-(p-butoxy)benzoyl-2-methylindole-4-acetic acid were discovered as new chemical leads for a prostaglandin D-2 (PGD(2)) receptor antagonist. Most of them exhibited PGD(2) receptor binding and blocked cyclic adenosine 3',5'-monophosphate (cAMP) formation in vitro. In particular, 2-methylindole-4-acetic acid analog 1 showed markedly increased receptor affinity and cAMP antagonist activity. Chemistry and structure activity relationship (SAR) data are also presented. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.11.011

文献信息

• METHODS AND COMPOSITIONS FOR INHIBITING OR REDUCING HAIR LOSS, ACNE, ROSACEA, PROSTATE CANCER, AND BPH
  申请人：The Trustees of the University of Pennsylvania

  公开号：US20160346186A1

  公开（公告）日：2016-12-01

  This invention provides methods of treating androgenetic alopecia (AGA), acne, rosacea, prostate cancer, and benign prostatic hypertrophy (BPH), comprising the step of contacting a subject with a compound or composition capable of decreasing prostaglandin D2 (PGD2) level or activity, a downstream signaling or receptor pathway thereof, or prostaglandin D2 synthase level or activity; methods of stimulating hair growth, comprising the step of contacting a subject with a compound or composition capable of increasing or decreasing the activity or level of a target gene of the present invention, or with a protein product of the target gene or an analogue or mimetic thereof; and methods of testing for AGA and evaluating therapeutic methods thereof, comprising measuring PGD2 levels.
• US9889082B2
  申请人：——

  公开号：US9889082B2

  公开（公告）日：2018-02-13
• Development of a prostaglandin D2 receptor antagonist: discovery of a new chemical lead
  作者：Kazuhiko Torisu、Kaoru Kobayashi、Maki Iwahashi、Hiromu Egashira、Yoshihiko Nakai、Yutaka Okada、Fumio Nanbu、Shuichi Ohuchida、Hisao Nakai、Masaaki Toda

  DOI：10.1016/j.ejmech.2004.11.011

  日期：2005.5

  A series of N-(p-alkoxy)benzoyl-5-methoxy-2-methylindole-3-acetic acids and N-(p-butoxy)benzoyl-2-methylindole-4-acetic acid were discovered as new chemical leads for a prostaglandin D-2 (PGD(2)) receptor antagonist. Most of them exhibited PGD(2) receptor binding and blocked cyclic adenosine 3',5'-monophosphate (cAMP) formation in vitro. In particular, 2-methylindole-4-acetic acid analog 1 showed markedly increased receptor affinity and cAMP antagonist activity. Chemistry and structure activity relationship (SAR) data are also presented. (c) 2005 Elsevier SAS. All rights reserved.