chloroacetic acid 1-(2,2-dimethylpropionyl)-1H-indol-6-yl ester | 160252-47-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: chloroacetic acid 1-(2,2-dimethylpropionyl)-1H-indol-6-yl ester
• 英文别名: 6-chloroacetoxy-1-pivaloylindole；chloro-acetic acid 1-(2,2-dimethyl-propionyl)-1H-indol-6-yl ester；[1-(2,2-dimethylpropanoyl)indol-6-yl] 2-chloroacetate
• CAS: 160252-47-1
• 化学式: C₁₅H₁₆ClNO₃
• 分子量: 293.75
• InChiKey: FVELASUFOUWLQX-UHFFFAOYSA-N

物化性质

• 沸点：
  400.4±20.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  48.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  chloroacetic acid 1-(2,2-dimethylpropionyl)-1H-indol-6-yl ester 在 三氯化铝 乙酸酐 作用下， 以 1,1-二氯乙烷 为溶剂， 以36%的产率得到3-acetyl-6-chloroacetoxy-1-pivaloylindole
  参考文献：
  名称：

  Indole derivatives with antiviral activity

  摘要：

  该化合物的化学式如下：其中R1为氢、低烷基或可选择取代的芳基磺酰基等；R2为氢、低烷基或可选择取代的芳基烷基等；R3、R4、R5和R6分别独立为氢、卤素、三卤代低烷基等；X为羟基或可选择取代的氨基；Y为COOR（R为氢或酯残基）、可选择取代的芳基或可选择取代的杂环烷基；具有整合酶抑制活性，可作为抗HIV药物使用。

  公开号：

  US06333323B1
• 作为产物：
  描述：

  1-[6-(氯乙酰基)-1H-吲哚-1-基]-2,2-二甲基-1-丙酮 在 disodium hydrogenphosphate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以80%的产率得到chloroacetic acid 1-(2,2-dimethylpropionyl)-1H-indol-6-yl ester
  参考文献：
  名称：

  Facile Synthesis of 6-Hydroxyindole and 6-Methoxyindole via Regioselective Friedel-Crafts Acylation and Baeyer-Villiger Oxidation

  摘要：

  本研究描述了一种从吲哚开始的 6-羟基吲哚和 6-甲氧基吲哚的简便合成方法。对 1-特戊酰基吲哚进行区域选择性氯乙酰化，然后进行拜耳-维里格氧化反应，从而在吲哚环的 6 位引入氧功能。对 6-氯乙酰基-1-特戊酰吲哚进行脱乙酰化可得到 6-羟基吲哚，通过甲基化可转化为 6-甲氧基吲哚。从吲哚中提取 6-羟基吲哚和 6-甲氧基吲哚的总收率分别为 54% 和 37%。

  DOI：

  10.1055/s-1994-25626

文献信息

• [EN] FUSED HETEROCYCLIC ISOXAZOLINE DERIVATIVES AND THEIR USE AS ANTI-DEPRESSANTS<br/>[FR] DERIVES D'ISOXAZOLINE HETEROCYCLIQUES FUSIONNES ET LEUR UTILISATION EN TANT QU'ANTIDEPRESSEURS
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2004018483A1

  公开（公告）日：2004-03-04

  The invention concerns fused heterocyclic isoxazoline derivatives of Formula (I), the pharmaceutically acceptable acid or base addition salts thereof, the stereochemically isomeric forms thereof and the N-oxide form thereof, more in particular, tetrahydropyranoisoxazole, hexahydroisoxazolopyridine, tetrahydrothiopyrano isoxazole and hexahydrobenzoisoxazole derivatives fused to a heterocyclic ring system via the 6-membered ring of the bicyclic moiety as well as processes for their preparation, pharmaceutical compositions comprising them and their use as a medicine, in particular for treating depression, anxiety, movement disorders, psychosis, Parkinson's disease and body weight disorders including anorexia nervosa and bulimia, wherein the variables are defined as in Claim 1. The compounds have surprisingly been shown to have selective serotonine (5-HT) reuptake inhibitor activity as well as α2-adrenoceptor antagonist activity, compounds according to the invention are also suitable for treatment and/or prophylaxis in diseases where either one of the activities alone or the combination of said activities may be of therapeutic use.

  该发明涉及Formula (I)的融合杂环异氧化烷衍生物，其药学上可接受的酸或碱盐，其立体化异构体以及其N-氧化物形式，更具体地说，通过双环部分的6元环连接到杂环环系统的四氢吡喃异氧化烷，六氢异氧化烷吡啶，四氢硫代吡喃异氧化烷和六氢苯并异氧化烷衍生物，以及它们的制备方法，包含它们的制药组合物以及它们作为药物的用途，特别是用于治疗抑郁症、焦虑症、运动障碍、精神病、帕金森病和体重紊乱，包括厌食症和暴食症，其中变量的定义如权利要求书第1项所述。这些化合物被惊人地证明具有选择性的5-羟色胺（5-HT）再摄取抑制剂活性以及α2-肾上腺素受体拮抗剂活性，根据本发明的化合物也适用于治疗和/或预防在该活性之一或该活性的组合可能具有治疗用途的疾病。
• A Facile Preparation of 1-(6-Hydroxyindol-1-yl)-2,2-dimethylpropan-1-one.
  作者：Vassilis John Demopoulos、Ioannis Nicolaou、Chariklia Zika

  DOI：10.1248/cpb.51.98

  日期：——

  An effective synthesis of 1-(6-hydroxyindol-1-yl)-2,2-dimethylpropan-1-one (4) was developed starting from 1H-indole (2). The key step involved suitable utilization of 4-(1-pyrrolidino)pyridine for the removal of the chloroacetyl moiety from chloroacetic acid 1-(2,2-dimethylpropionyl)-1H-indol-6-yl ester (3); a possible mechanism is, also, presented. Compound 4 might lead to selectively substituted derivatives, either on the phenolic-OH or the indolyl-NH, with putative biological interest. In this respect, we found that the core structure of 1H-indol-6-ol (1) possesses a degree of aldose reductase inhibitory potential, at a concentration of 100 μM.

  以 1H-吲哚（2）为起点，开发出了 1-(6-羟基吲哚-1-基)-2,2-二甲基丙-1-酮（4）的有效合成方法。关键步骤是适当利用 4-(1-吡咯烷基)吡啶去除氯乙酸 1-(2,2-二甲基丙酰基)-1H-吲哚-6-基酯（3）中的氯乙酰基；同时还提出了一种可能的机理。化合物 4 可能会产生选择性取代的衍生物，无论是在酚-OH 还是在吲哚-NH 上，都可能具有生物学意义。在这方面，我们发现 1H-indol-6-ol (1) 的核心结构具有一定程度的醛糖还原酶抑制潜力，浓度为 100 μ<小>M。
• Indole derivatives having an antiviral activity
  申请人：——

  公开号：US20030181499A1

  公开（公告）日：2003-09-25

  A compound of the formula: 1 wherein R 1 is hydrogen, lower alkyl, or optionally substituted arylsulfonyl, or the like, R 2 is hydrogen, lower alkyl, or optionally substituted aralkyl, or the like, R 3 , R 4 , R 5 , and R 6 each is independently hydrogen, halogen, trihalogenated lower alkyl, or the like, X is hydroxy or optionally substituted amino, Y is COOR (E is hydrogen or an ester residue), optionally substituted aryl, or optionally substituted heteroaryl, has integrase inhibition activity, and is useful as an anti-HIV drug.

  该化合物的公式为1，其中R1为氢、较低的烷基、或可选取代的芳基磺酰基等；R2为氢、较低的烷基、或可选取代的芳基烷基等；R3、R4、R5和R6分别独立地为氢、卤素、三卤代较低的烷基等；X为羟基或可选取代的氨基；Y为COOR（E为氢或酯基残基）、可选取代的芳基或可选取代的杂环基。该化合物具有整合酶抑制活性，可用作抗HIV药物。
• Fused heterocyclic isoxazoline derivatives and their use as anti-derpressants
  申请人：Andres-Gil Ignacio Jose

  公开号：US20060116378A1

  公开（公告）日：2006-06-01

  The invention concerns fused heterocyclic isoxazoline derivatives of Formula (I), the pharmaceutically acceptable acid or base addition salts thereof, the stereochemically isomeric forms thereof and the N-oxide form thereof, more in particular, tetrahydropyranoisoxazole, hexahydroisoxazolopyridine, tetrahydrothiopyrano isoxazole and hexahydrobenzoisoxazole derivatives fused to a heterocyclic ring system via the 6-membered ring of the bicyclic moiety as well as processes for their preparation, pharmaceutical compositions comprising them and their use as a medicine, in particular for treating depression, anxiety, movement disorders, psychosis, Parkinson's disease and body weight disorders including anorexia nervosa and bulimia, wherein the variables are defined as in Claim 1. The compounds have surprisingly been shown to have selective serotonine (5-HT) reuptake inhibitor activity as well as α 2 -adrenoceptor antagonist activity, compounds according to the invention are also suitable for treatment and/or prophylaxis in diseases where either one of the activities alone or the combination of said activities may be of therapeutic use.

  本发明涉及公式（I）的融合杂环异噁唑衍生物，其药学上可接受的酸或碱盐，其立体化异构体形式和N-氧化物形式，更具体地，通过双环基团的6元环与杂环环系统融合的四氢吡喃异噁唑，六氢异噁唑吡啶，四氢硫代吡喃异噁唑和六氢苯并异噁唑衍生物，以及其制备方法，包括它们的制药组合物和作为药物的用途，特别是用于治疗抑郁症，焦虑症，运动障碍，精神病，帕金森病和体重障碍，包括厌食症和贪食症，其中变量的定义如权利要求1所述。这些化合物已被证明具有选择性的5-羟色胺（5-HT）再摄取抑制剂活性以及α2-肾上腺素受体拮抗剂活性，根据本发明的化合物也适用于治疗和/或预防单独或联合使用这些活性可能具有治疗用途的疾病。
• INDOLE DERIVATIVES WITH ANTIVIRAL ACTIVITY
  申请人：SHIONOGI & CO., LTD.

  公开号：EP1069111A1

  公开（公告）日：2001-01-17

  A compound of the formula: wherein R1 is hydrogen,lower alkyl, or optionally substituted arylsulfonyl, or the like, R2 is hydrogen, lower alkyl, or optionally substituted aralkyl, or the like, R3, R4, R5, and R6 each is independently hydrogen, halogen, trihalogenated lower alkyl, or the like, X is hydroxy or optionally substituted amino, Y is COOR (R is hydrogen or an ester residue), optionally substituted aryl, or optionally substituted heteroaryl, has intense integrase inhibition activity, and is useful as an anti-HIV drug.

  式中的化合物： 式中 R1 是氢、低级烷基或任选取代的芳基磺酰基或类似物、 R2 是氢、低级烷基或任选取代的芳烷基或类似物、 R3、R4、R5 和 R6 各自独立地为氢、卤素、三卤代低级烷基或类似物、 X 是羟基或任选取代的氨基、 Y 是 COOR（R 是氢或酯残基）、任选取代的芳基或任选取代的杂芳基、 具有强烈的整合酶抑制活性，可用作抗艾滋病毒药物。