1-tert-butoxycarbonyl-2-methyl-1H-indol-4-yl acetic acid | 359585-99-2

• 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: 1-tert-butoxycarbonyl-2-methyl-1H-indol-4-yl acetic acid
• 英文别名: 1-t-butoxycarbonyl-2-methylindole-4-acetic acid；2-[2-methyl-1-[(2-methylpropan-2-yl)oxycarbonyl]indol-4-yl]acetic acid
• CAS: 359585-99-2
• 化学式: C₁₆H₁₉NO₄
• 分子量: 289.331
• InChiKey: BMXFLXXRFAIXRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-tert-butoxycarbonyl-2-methyl-1H-indol-4-yl acetic acid 在 四氢吡咯 、 sodium hydroxide 、 四丁基氯化铵 、 potassium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 benzyl [1-(4-butoxybenzoyl)-2-methyl-1H-indol-4-yl]acetate
  参考文献：
  名称：

  Discovery of orally active prostaglandin D2 receptor antagonists

  摘要：

  A series of N-(p-alkoxy)benzoyl-2-methylindole-4-acetic acids were synthesized and evaluated for prostaglandin D-2 (DP) receptor affinity and antagonist activity. Some of them exhibited strong receptor binding and were potent in the cAMP formation assays. These antagonists also suppressed allergic inflammatory responses such as the PGD(2)-induced increase of microvascular permeability. Structure-activity relationship (SAR) data are presented. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.039
• 作为产物：
  描述：

  2-methyl-1H-indol-4-yl trifluoromethanesulfonate 在 TEA 4-二甲氨基吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 bis(cyclohexanyl)borane 、 四丁基碘化铵 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 1-tert-butoxycarbonyl-2-methyl-1H-indol-4-yl acetic acid
  参考文献：
  名称：

  Discovery of orally active prostaglandin D2 receptor antagonists

  摘要：

  A series of N-(p-alkoxy)benzoyl-2-methylindole-4-acetic acids were synthesized and evaluated for prostaglandin D-2 (DP) receptor affinity and antagonist activity. Some of them exhibited strong receptor binding and were potent in the cAMP formation assays. These antagonists also suppressed allergic inflammatory responses such as the PGD(2)-induced increase of microvascular permeability. Structure-activity relationship (SAR) data are presented. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.039

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。
• 17-Beta-hydroxysteroid dehydrogenase-II inhibitors
  申请人：——

  公开号：US20030087952A1

  公开（公告）日：2003-05-08

  17-beta-hydroxysteroid dehydrogenase-I1 inhibitors having the structural formula 1 wherein the phenyl group labeled A and the group —C(R 4 )(R 6 )Y are oriented cis to each other; W represents 0 or S; R 1 represents —H or optionally substituted —(C 1 -C 4 )alkyl; n represents 0 or an integer of 1-3; and R 2 represents any of a variety of substituents on ring A. R 4 generally represents —H but may be a bond terminating at the ortho position of ring A. Y represents fluorine, —OR 5 , or —SR 5 , and R 5 represents —H. optionally substituted —(C 1 -C 4 )alkyl, optionally substituted -phenyl, optionally substituted —(C 1 -C 4 )alkyl-phenyl, or optionally substituted —(C 1 -C 4 )acyl. R 6 represents any of a variety of groups as defined in the specification and claims, including heteroaryl, arylalkyl, heteroarylalkyl, arylalkenyl, heteroarylalkenyl, alkynyl, arylalkynyl, heteroarylalkynyl, aryl, and indolyl. Pharmaceutically acceptable salts and N-oxides of these materials are also included. Also claimed are pharmaceutical compositions containing these materials and methods of using them.

  17-beta-羟基类固醇脱氢酶I1抑制剂具有结构式1，其中苯基A和基团—C(R4)(R6)Y相对取向；W代表0或S；R1代表—H或可选择取代的—(C1-C4)烷基；n代表0或1-3的整数；R2代表环A上的各种取代基之一。R4通常代表—H，但可能是终止在环A的邻位的键。Y代表氟、—OR5或—SR5，R5代表—H、可选择取代的—(C1-C4)烷基、可选择取代的苯基、可选择取代的—(C1-C4)烷基-苯基或可选择取代的—(C1-C4)酰基。R6代表根据说明书和索赔中定义的各种基团之一，包括杂芳基、芳基烷基、杂芳基烷基、芳基烯基、杂芳基烯基、炔基、芳基炔基、杂芳基炔基、芳基和吲哚基。还包括这些物质的药用合适盐和N-氧化物。还声明包含这些物质的药物组合物和使用它们的方法。
• Indole derivatives, process for producing the same and drugs containing the same as the active ingredient
  申请人：Torisu Kazuhiko

  公开号：US20050004096A1

  公开（公告）日：2005-01-06

  Indole derivatives represented by formula (I) wherein all symbols represent the same as that in specification), production methods thereof, and DP receptor antagonist comprising them as active ingredients. Since the compounds of formula (I) binds and antagonizes to DP receptor, they are useful for the prevention and/or treatment against allergic diseases, diseases accompanied with itching, secondary diseases generated by behaviors caused by itching, inflammation, chronic obstructive pulmonary disease, ischemic reperfusion disorder, cerebrovascular disorder, pleuritis complicated by rheumatoid arthritis, ulcerative colitis.

  公式（I）所表示的吲哚衍生物（其中所有符号均与规范中相同），其生产方法以及包含它们作为活性成分的DP受体拮抗剂。由于公式（I）中的化合物结合并拮抗DP受体，因此它们对于预防和/或治疗过敏性疾病、伴随瘙痒的疾病、由瘙痒引起的行为所致的继发疾病、炎症、慢性阻塞性肺疾病、缺血再灌注障碍、脑血管疾病、风湿性关节炎并发的胸膜炎、溃疡性结肠炎等具有用处。
• 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。
• INDOLE DERIVATIVES, PROCESS FOR PRODUCING THE SAME AND DRUGS CONTAINING THE SAME AS THE ACTIVE INGREDIENT
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP1424325A1

  公开（公告）日：2004-06-02

  Indole derivatives represented by formula (I)    wherein all symbols represent the same as that in specification), production methods thereof, and DP receptor antagonist comprising them as active ingredients. Since the compounds of formula (I) binds and antagonizes to DP receptor, they are useful for the prevention and/or treatment against allergic diseases, diseases accompanied with itching, secondary diseases generated by behaviors caused by itching, inflammation, chronic obstructive pulmonary disease, ischemic reperfusion disorder, cerebrovascular disorder, pleuritis complicated by rheumatoid arthritis, ulcerative colitis.

  由式（I）代表的吲哚衍生物 其中所有符号均与说明书中的符号相同）的吲哚衍生物、其生产方法以及以它们为活性成分的 DP 受体拮抗剂。 由于式（I）化合物能结合并拮抗 DP 受体，因此可用于预防和/或治疗过敏性疾病、伴随瘙痒的疾病、由瘙痒引起的行为所导致的继发性疾病、炎症、慢性阻塞性肺病、缺血性再灌注疾病、脑血管疾病、类风湿性关节炎并发的胸膜炎、溃疡性结肠炎。