4,6-dichloro-5-(3-isopropyl-4-methoxy-phenoxy)-1H-indole-2-carboxylic acid ethyl ester | 503632-12-0

• 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: 4,6-dichloro-5-(3-isopropyl-4-methoxy-phenoxy)-1H-indole-2-carboxylic acid ethyl ester
• 英文别名: 4,6-dichloro-5-(4-methoxy-3-isopropylphenoxy)-1H-indole-2-carboxylic acid ethyl ester；ethyl 4,6-dichloro-5-(4-methoxy-3-propan-2-ylphenoxy)-1H-indole-2-carboxylate
• CAS: 503632-12-0
• 化学式: C₂₁H₂₁Cl₂NO₄
• 分子量: 422.308
• InChiKey: MWWACBCEEGTOPG-UHFFFAOYSA-N

物化性质

• 沸点：
  529.3±50.0 °C(Predicted)
• 密度：
  1.300±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  60.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,6-dichloro-5-(3-isopropyl-4-methoxy-phenoxy)-1H-indole-2-carboxylic acid ethyl ester 在 sodium hydroxide 、 三溴化硼 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 4,6-Dichloro-5-(4-hydroxy-3-isopropyl-phenoxy)-1H-indole-2-carboxylic acid
  参考文献：
  名称：

  Thyroid receptor ligands. Part 5: Novel bicyclic agonist ligands selective for the thyroid hormone receptor β

  摘要：

  Based on the examination of the crystal structure of rat TR beta complexed with 3,5,3'-triiodo-L-thyronine (2) a novel TR beta-selective indole derivative 6b was prepared and tested in vitro. This compound was found to be 14 times selective for TR beta over TR alpha in binding and its beta-selectivity could be rationalized through the comparison of the X-ray crystallographic structures of 6b complexed with TR alpha and TR beta. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.11.077
• 作为产物：
  描述：

  3,5-二氯-4-(3'-异丙基-4'-甲氧基苯氧基)-硝基苯 生成 4,6-dichloro-5-(3-isopropyl-4-methoxy-phenoxy)-1H-indole-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Indole carboxylic acids as thyroid receptor ligands

  摘要：

  一种化合物的公式1，其中W，R1，R2，R3，R4，R5，R6，R7，R8和R13如本文所定义，在治疗肥胖、超重症、高脂血症、青光眼、心律失常、皮肤疾病、甲状腺疾病、甲状腺功能减退症、甲状腺癌及相关疾病和疾病（如糖尿病、动脉粥样硬化、高血压、冠心病、充血性心力衰竭、高胆固醇血症、抑郁症、骨质疏松症和脱发）的治疗中有用。

  公开号：

  US20030078289A1

文献信息

• [EN] IDOL DERIVATIVES AS NEW THYROID RECEPTOR AGONIST LIGANDS AND METHODS<br/>[FR] DERIVES D'INDOL UTILISES COMME NOUVEAUX LIGANDS AGONISTES DU RECEPTEUR DE LA THYROIDE
  申请人：KAROBIO AB

  公开号：WO2004018421A1

  公开（公告）日：2004-03-04

  This invention relates to novel compounds of the general formula (I), which are thyroid receptor ligands, and are preferably selective for the thyroid hormone receptor Beta and to methods of preparing such compound. In addition, a method is provided for preventing, inhibiting or treating diseases or disorders associated with metabolism dysfunction or which are dependent upon the expression of a T3 regulated gene, wherein a compound as described herein is administered in a therapeutically effective amount.

  本发明涉及一般式(I)的新化合物，这些化合物是甲状腺受体配体，且优选选择性作用于甲状腺激素受体Beta，并提供了制备这种化合物的方法。此外，提供了一种用于预防、抑制或治疗与代谢功能紊乱有关或依赖于T3调控基因表达的疾病或疾病的方法，其中根据本文所述的化合物以治疗有效剂量的方式给予。
• US6723744B2
  申请人：——

  公开号：US6723744B2

  公开（公告）日：2004-04-20
• Indole carboxylic acids as thyroid receptor ligands
  申请人：——

  公开号：US20030078289A1

  公开（公告）日：2003-04-24

  A compound of the formula 1 wherein W, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 13 are as defined herein, useful in the treatment of obesity, overweight condition, hyperlipidemia, glaucoma, cardiac arrhythmias, skin disorders, thyroid disease, hypothyroidism, thyroid cancer and related disorders and diseases such as diabetes mellitus, atherosclerosis, hypertension, coronary heart disease, congestive heart failure, hypercholesteremia, depression, osteoporosis and hair loss.

  一种化合物的公式1，其中W，R1，R2，R3，R4，R5，R6，R7，R8和R13如本文所定义，在治疗肥胖、超重症、高脂血症、青光眼、心律失常、皮肤疾病、甲状腺疾病、甲状腺功能减退症、甲状腺癌及相关疾病和疾病（如糖尿病、动脉粥样硬化、高血压、冠心病、充血性心力衰竭、高胆固醇血症、抑郁症、骨质疏松症和脱发）的治疗中有用。
• Thyroid receptor ligands. Part 5: Novel bicyclic agonist ligands selective for the thyroid hormone receptor β
  作者：Ana-Maria Garcia Collazo、Konrad F. Koehler、Neeraj Garg、Mathias Färnegårdh、Bolette Husman、Liu Ye、Jan Ljunggren、Karin Mellström、Johnny Sandberg、Marlena Grynfarb、Harri Ahola、Johan Malm

  DOI：10.1016/j.bmcl.2005.11.077

  日期：2006.3

  Based on the examination of the crystal structure of rat TR beta complexed with 3,5,3'-triiodo-L-thyronine (2) a novel TR beta-selective indole derivative 6b was prepared and tested in vitro. This compound was found to be 14 times selective for TR beta over TR alpha in binding and its beta-selectivity could be rationalized through the comparison of the X-ray crystallographic structures of 6b complexed with TR alpha and TR beta. (C) 2005 Elsevier Ltd. All rights reserved.