(3,5-dibromo-4-(5-isopropyl-4-methoxy-phenoxy)-phenyl)-acetic acid methyl ester | 219692-15-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3,5-dibromo-4-(5-isopropyl-4-methoxy-phenoxy)-phenyl)-acetic acid methyl ester
• 英文别名: methyl [3,5-dibromo-4-(4-methoxy-3-isopropylphenoxy)phenyl] acetate；methyl 3,5-dibromo-4-(4-methoxy-3-isopropylphenoxy)phenyl acetate；3,5-dibromo-4-(3-isopropyl-4-methoxyphenoxy)phenylacetic acid methyl ester；methyl 3,5-dibromo-4-(4-methoxy-3-Isopropyl-phenoxy)phenylacetate；methyl[3,5-dibromo-4-(3-isopropyl-4-methoxyphenoxy)phenyl]acetate；methyl 2-[3,5-dibromo-4-(4-methoxy-3-propan-2-ylphenoxy)phenyl]acetate
• CAS: 219692-15-6
• 化学式: C₁₉H₂₀Br₂O₄
• 分子量: 472.173
• InChiKey: CZXSFWVJGDJJTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3,5-dibromo-4-(5-isopropyl-4-methoxy-phenoxy)-phenyl)-acetic acid methyl ester 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以62%的产率得到KB-131092
  参考文献：
  名称：

  甲状腺受体配体。1.对甲状腺受体beta1具有选择性的激动剂配体。

  摘要：

  内源性甲状腺受体激素3,5,3'，5'-四碘-1-甲状腺素（T（4），1）和3,5,3'-三碘-1-甲状腺素（T（3），2）对哺乳动物的生长，发育和体内平衡具有重大影响。它们调节肠，骨骼和心肌，肝脏和中枢神经系统中的重要基因，影响整体代谢率，胆固醇和甘油三酸酯水平和心率，并影响情绪和整体幸福感。文献表明，甲状腺激素对心脏的许多或大多数作用，特别是对心率和节律的影响，是通过TRalpha（1）亚型介导的，而大多数激素对肝脏和其他组织的作用更多地是通过甲状腺激素介导的。受体的TRbeta（1）同工型。如果可以将不良反应减至最小或消除，则甲状腺激素的某些作用可能在非甲状腺疾病中具有治疗作用。这些潜在有用的功能包括：减轻体重以治疗肥胖症；降低胆固醇以治疗高血脂症；减轻抑郁症；以及刺激骨质疏松症中的骨形成。先前在药理上利用甲状腺激素治疗这些疾病的尝试受到甲亢的表现，特别是心血管毒性的限制。因此，对β

  DOI：

  10.1021/jm021080f
• 作为产物：
  描述：

  2-异丙基苯甲醚 在 三氟甲磺酸 、 caesium carbonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 (3,5-dibromo-4-(5-isopropyl-4-methoxy-phenoxy)-phenyl)-acetic acid methyl ester
  参考文献：
  名称：

  高价碘介导的 C-H 官能化合成二芳基醚

  摘要：

  采用基于高价碘试剂的 C-H 官能化策略来合成二芳基醚。该方法直接将各种芳烃转化为相应的二芳基碘鎓盐，然后进行C-O偶联反应，生成结构多样的二芳基醚。证明了这种方法在复杂分子后期结构修饰中的功效。

  DOI：

  10.1021/acs.orglett.4c02703

文献信息

• Glucocorticoid and thyroid hormone receptor ligands for the treatment of metabolic disorders
  申请人：Karo Bio AB

  公开号：US06492424B1

  公开（公告）日：2002-12-10

  Novel glucocorticoid and thyroid receptor ligands as provided which have the general formula (I): in which R1 is an aliphatic hydrocarbon, an aromatic hydrocarbon, carboxylic acid or ester thereof, alkenyl carboxylic acid or ester thereof, hydroxy, halogen, or cyano, or a pharmaceutically acceptable salt thereof. R2 and R3 are the same or different, and are hydrogen, halogen, alkyl of 1 to 4 carbons, or cycloalkyl of 3 to 5 carbons, at least one of R2 and R3 being other than hydrogen. X is carbonyl or methylene. R4 is an aliphatic, aromatic or heteroaromatic. Y is hydroxyl, methoxy, amino, or alkyl amino. n is an integer from 0 to 4. A method for treating diseases associated with metabolism dysfunction or which are dependent on the expression of a glucocorticoid or thyroid receptor gene such as diabetes, hypercholesterolemia, or obesity using these compounds is also disclosed.

  提供了新型糖皮质激素和甲状腺受体配体，其具有一般式（I）：其中R1为脂肪烃、芳香烃、羧酸或其酯、烯基羧酸或其酯、羟基、卤素、或氰基，或其药用可接受的盐。R2和R3相同或不同，为氢、卤素、1至4碳的烷基，或3至5碳的环烷基，R2和R3中至少一个不是氢。X为羰基或亚甲基。R4为脂肪烃、芳香烃或杂环芳烃。Y为羟基、甲氧基、氨基或烷基氨基。n为0至4的整数。还公开了使用这些化合物治疗与代谢功能障碍有关或依赖于糖皮质激素或甲状腺受体基因表达的疾病的方法，例如糖尿病、高胆固醇血症或肥胖症。
• Compounds active at the glucocorticoid receptor
  申请人：——

  公开号：US20030166725A1

  公开（公告）日：2003-09-04

  This invention relates to novel compounds that are liver selective glucocorticoid receptor antagonists, to methods of preparing such compounds, and to methods for using such compounds in therapy and in the regulation of metabolism, especially lowering blood glucose levels. The compounds referred to are compounds according to the formula (I).

  这项发明涉及一种新型化合物，它们是肝选择性糖皮质激素受体拮抗剂，涉及制备这种化合物的方法，以及使用这种化合物进行治疗和调节新陈代谢的方法，尤其是降低血糖水平。所提到的化合物是根据式(I)的化合物。
• Novel compounds
  申请人：Garg Neeraj

  公开号：US20060135614A1

  公开（公告）日：2006-06-22

  This invention relates to novel compounds, which are thyroid receptor ligands, and to methods of preparing such compounds. 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.

  本发明涉及一种新型化合物，它们是甲状腺受体配体，并提供了制备这些化合物的方法。此外，本发明还提供了一种预防、抑制或治疗与代谢功能紊乱相关的疾病或随着T3调节基因表达而产生的疾病或障碍的方法，其中所述的化合物以治疗有效量的方式给予。
• Compounds active at the glucocorticoid receptor II
  申请人：——

  公开号：US20040063781A1

  公开（公告）日：2004-04-01

  1 This invention relates to novel compounds that are liver selective glucocorticoid receptor antagonists, to methods of preparing such compounds, and to methods for using such compounds in therapy and in the regulation of metabolism, especially lowering blood glucose levels. The compounds referred to are compounds according to the formula 1: wherein X is selected from: CH 2 , CHYR 7 , CHYC(O)R 7 , C═O, C═S, and C═NOR 8 ,; Y is selected from: O, S, and NR 8 ; R 1 is selected from: COOH and heteroaryl; R 2 and R 3 are independently of each other selected from: hydrogen, halogen, and C 1-6 alkyl, provided that one of R 2 or R 3 is other than hydrogen; R 4 is selected from: C 1-6 -alkyl, C 2-6 alkenyl, C 2-6 -alkynyl, halogen, (R 9 )(R 10 )N, R 8 C(Z)N(R 11 ), R 8 OC(Z)N(R 11 ), (R 9 )(R 10 )NC(Z)N(R 11 ),R 8 S(O) 2 N(R 11 ), (R 9 )(R 10 )NS(O) 2 N(R 11 ), and R 8 SC(Z)N(R 11 );R 5 is selected from: (i) C 1-6 -alkyl which is substituted by a group selected from A, provided that A is not halogen; (ii) C 7-12 -alkyl, C 2-12 -alkenyl and C 2-12 -alkynyl; (iii) C 1-2 -alkyl, where one or more carbon atoms are replaced by Y, and where one or more carbons are optionally substituted by a group selected from A, provided that if more than one carbon is replaced by Y, the said Y groups are not directly connected to each other; R 6 is selected from: C 1-12 -alkyl, C 3-8 -cycloalkyl, C 3-8 -heterocycloalkyl, C 2-6 -alkenyl, and C 2-6 -alkynyl, aryl, and heteroaryl; R 7 is optionally selected from hydrogen; R 8 , R 9 , R 10 and R 11 are independently of each other selected from: hydrogen, C 1-6 -alkyl, C 3-8 -cycloalkyl, C 2-6 -alkenyl, C 2-6 -alkynyl, and C 3-8 -heterocycloalkyl, aryl and heteroaryl; or where any pair of R 8 , R 9 , R 10 and R 11 together with the atom or atoms to which they are bound form a ring having 3-7 ring members; or pharmaceutically acceptable salts, stereoisomers or prodrugs thereof.

  本发明涉及一种新型化合物，它们是肝脏选择性糖皮质激素受体拮抗剂，涉及制备这种化合物的方法，以及在治疗和调节新陈代谢方面使用这种化合物的方法，特别是降低血糖水平。所提到的化合物是根据式1的化合物：其中X选自：CH2，CHYR7，CHYC（O）R7，C═O，C═S和C═NOR8; Y选自：O，S和NR8; R1选自：COOH和杂环芳基; R2和R3分别选自：氢，卤素和C1-6烷基，前提是其中一个R2或R3不是氢; R4选自：C1-6烷基，C2-6烯基，C2-6炔基，卤素，（R9）（R10）N，R8C（Z）N（R11），R8OC（Z）N（R11），（R9）（R10）NC（Z）N（R11），R8S（O）2N（R11），（R9）（R10）NS（O）2N（R11）和R8SC（Z）N（R11）; R5选自：（i）被A取代的C1-6烷基，其中A被选择为不是卤素的基团; （ii）C7-12烷基，C2-12烯基和C2-12炔基; （iii）C1-2烷基，其中一个或多个碳原子被Y取代，并且其中一个或多个碳原子可以被选择为被A取代的基团，前提是如果超过一个碳原子被Y取代，则所述的Y基团不直接连接在一起; R6选自：C1-12烷基，C3-8环烷基，C3-8杂环环烷基，C2-6烯基和C2-6炔基，芳基和杂环芳基; R7可选地选自氢; R8，R9，R10和R11分别选自：氢，C1-6烷基，C3-8环烷基，C2-6烯基，C2-6炔基和C3-8杂环环烷基，芳基和杂环芳基; 或其中任何一对R8，R9，R10和R11与它们所结合的原子一起形成具有3-7个环成员的环；或其药学上可接受的盐，立体异构体或前药。
• Benzamide derivatives as thyroid receptor ligands
  申请人：Karo Bio AB

  公开号：US07153997B2

  公开（公告）日：2006-12-26

  This invention relates to novel compounds, which are thyroid receptor ligands, and to methods of preparing such compounds. 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.

  本发明涉及新型化合物，它们是甲状腺受体配体，并涉及制备这种化合物的方法。此外，提供了一种方法，用于预防、抑制或治疗与代谢功能障碍或依赖于T3调节基因表达的疾病或疾病，其中以本文所述的化合物以治疗有效量的方式给予。