allyl {[1-(4-butoxybenzoyl)-2-methyl-1H-indol-4-yl]oxy}acetate | 359586-07-5

• 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: allyl {[1-(4-butoxybenzoyl)-2-methyl-1H-indol-4-yl]oxy}acetate
• 英文别名: 1-(4-Butoxybenzoyl)-2-methylindol-4-yloxyacetic Acid Allyl Ester；Prop-2-enyl 2-[1-(4-butoxybenzoyl)-2-methylindol-4-yl]oxyacetate
• CAS: 359586-07-5
• 化学式: C₂₅H₂₇NO₅
• 分子量: 421.493
• InChiKey: YLENNJIWRSQXEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  66.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  allyl {[1-(4-butoxybenzoyl)-2-methyl-1H-indol-4-yl]oxy}acetate 在 四(三苯基膦)钯 吗啉 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以79%的产率得到1-(4-Butoxybenzoyl)-2-methylindol-4-yloxyacetic Acid
  参考文献：
  名称：

  Development of prostaglandin D2 receptor antagonist: discovery of highly potent antagonists

  摘要：

  The process of discovery for highly potent prostaglandin D-2 (PGD(2)) receptor antagonists is reported. A series of N-(p-alkoxy)benzoyl-2-methylindole-4-acetic acids were synthesized and identified as a new class of selective PGD(2) receptor antagonists. Most of them exhibited strong PGD(2) receptor antagonism in binding studies and the cAMP formation assay. The structure-activity relationships (SAR), including subtype selectivity of the synthesized compounds, are also discussed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.06.024
• 作为产物：
  描述：

  methyl [(2-methyl-1H-indol-4-yl)oxy]acetate 在 sodium hydroxide 、 sodium hydride 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.5h， 生成 allyl {[1-(4-butoxybenzoyl)-2-methyl-1H-indol-4-yl]oxy}acetate
  参考文献：
  名称：

  Development of prostaglandin D2 receptor antagonist: discovery of highly potent antagonists

  摘要：

  The process of discovery for highly potent prostaglandin D-2 (PGD(2)) receptor antagonists is reported. A series of N-(p-alkoxy)benzoyl-2-methylindole-4-acetic acids were synthesized and identified as a new class of selective PGD(2) receptor antagonists. Most of them exhibited strong PGD(2) receptor antagonism in binding studies and the cAMP formation assay. The structure-activity relationships (SAR), including subtype selectivity of the synthesized compounds, are also discussed. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.06.024

文献信息

• Indole derivatives, process for preparation of the same and use thereof
  申请人：——

  公开号：US20030176400A1

  公开（公告）日：2003-09-18

  Indole derivatives represented by formula (I): 1 (wherein all symbols are described in the description), a process for the preparation of the same and a DP receptor antagonist comprising it as an active ingredient. Since the compounds of formula (I) binds to and are antagonistic to a DP receptor, they are useful in for the prevention and/or treatment of diseases, for example, allergic diseases (allergic rhinitis, allergic conjunctivitis, atopic dermatitis, bronchial asthma, food allergy, etc., systemic mastocytosis; disorders due to systemic mastocyte activation, anaphylactic shock, bronchoconstriction, urticaria, eczema, etc.), diseases accompanied with itching (atopic dermatitis, urticaria, etc.), secondary diseases caused by behaviors (scratching behaviors, beating, etc.) (cataract, retinal detachment, inflammation, infection, sleep disorder, etc.), inflammation, chronic obstructive pulmonary disease, ischemic reperfusion disorder, cerebrovascular disorder, pleuritis complicated by rheumatoid arthritis, ulcerative colitis, and the like.

  Indole 衍生物的化学式（I）：1（其中所有符号在描述中有描述），以及制备该化合物的方法和作为活性成分的 DP 受体拮抗剂。由于化合物的化学式（I）与 DP 受体结合并具有拮抗作用，因此它们在预防和/或治疗疾病方面非常有用，例如过敏性疾病（过敏性鼻炎、过敏性结膜炎、特应性皮炎、支气管哮喘、食物过敏等）、全身肥大细胞增多症；由于全身肥大细胞激活引起的疾病、过敏性休克、支气管痉挛、荨麻疹、湿疹等）、伴有瘙痒的疾病（特应性皮炎、荨麻疹等）、由行为引起的继发性疾病（搔抓行为、殴打等）（白内障、视网膜脱离、炎症、感染、睡眠障碍等）、炎症、慢性阻塞性肺病、缺血再灌注障碍、脑血管障碍、风湿性关节炎并发的胸膜炎、溃疡性结肠炎等。
• INDOLE DERIVATIVES, PROCESS FOR PREPARATION OF THE SAME AND USE THEREOF
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP1262475A1

  公开（公告）日：2002-12-04

  Indole derivatives represented by formula (I): (wherein all symbols are described in the description), a process for the preparation of the same and a DP receptor antagonist comprising it as an active ingredient. Since the compounds of formula (I) binds to and are antagonistic to a DP receptor, they are useful in for the prevention and/or treatment of diseases, for example, allergic diseases (allergic rhinitis, allergic conjunctivitis, atopic dermatitis, bronchial asthma, food allergy, etc., systemic mastocytosis; disorders due to systemic mastocyte activation, anaphylactic shock, bronchoconstriction, urticaria, eczema, etc.), diseases accompanied with itching (atopic dermatitis, urticaria, etc.), secondary diseases caused by behaviors (scratching behaviors, beating, etc.) (cataract, retinal detachment, inflammation, infection, sleep disorder, etc.), inflammation, chronic obstructive pulmonary disease, ischemic reperfusion disorder, cerebrovascular disorder, pleuritis complicated by rheumatoid arthritis, ulcerative colitis, and the like.

  由式（I）代表的吲哚衍生物： 式（I）代表的吲哚衍生物（其中所有符号已在描述中说明）、制备该衍生物的工艺以及以其为活性成分的 DP 受体拮抗剂。由于式 (I) 化合物与 DP 受体结合并对其具有拮抗作用，因此可用于预防和/或治疗疾病，例如过敏性疾病（过敏性鼻炎、过敏性结膜炎、特应性皮炎、支气管哮喘、食物过敏等）、系统性肥大细胞增多症、过敏性结膜炎、过敏性皮炎、支气管哮喘、食物过敏等、全身性肥大细胞增多症；全身性肥大细胞活化引起的疾病、过敏性休克、支气管收缩、荨麻疹、湿疹等）、伴有瘙痒的疾病（异位性皮炎、荨麻疹等）、由行为（抓挠行为、殴打等）引起的继发性疾病（白内障、视网膜病变等）。白内障、视网膜脱落、炎症、感染、睡眠障碍等）、炎症、慢性阻塞性肺病、缺血再灌注障碍、脑血管障碍、类风湿性关节炎并发胸膜炎、溃疡性结肠炎等。
• US6743793B2
  申请人：——

  公开号：US6743793B2

  公开（公告）日：2004-06-01
• US7098234B2
  申请人：——

  公开号：US7098234B2

  公开（公告）日：2006-08-29
• Development of prostaglandin D2 receptor antagonist: discovery of highly potent antagonists
  作者：Kazuhiko Torisu、Kaoru Kobayashi、Maki Iwahashi、Yoshihiko Nakai、Takahiro Onoda、Toshihiko Nagase、Isamu Sugimoto、Yutaka Okada、Ryoji Matsumoto、Fumio Nanbu、Shuichi Ohuchida、Hisao Nakai、Masaaki Toda

  DOI：10.1016/j.bmc.2004.06.024

  日期：2004.9

  The process of discovery for highly potent prostaglandin D-2 (PGD(2)) receptor antagonists is reported. A series of N-(p-alkoxy)benzoyl-2-methylindole-4-acetic acids were synthesized and identified as a new class of selective PGD(2) receptor antagonists. Most of them exhibited strong PGD(2) receptor antagonism in binding studies and the cAMP formation assay. The structure-activity relationships (SAR), including subtype selectivity of the synthesized compounds, are also discussed. (C) 2004 Elsevier Ltd. All rights reserved.