4-(5-bromo-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethylpentanoic acid ethyl ester | 609807-36-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 4-(5-bromo-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethylpentanoic acid ethyl ester
• 英文别名: ethyl 4-(5-bromo-2,3-dihydro-1-benzofuran-7-yl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanoate
• CAS: 609807-36-5
• 化学式: C₁₇H₂₀BrF₃O₄
• 分子量: 425.243
• InChiKey: KOOCNVKJNQHGJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(5-bromo-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethylpentanoic acid ethyl ester 在 lithium aluminium tetrahydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 5-bromo-7-[2-(2,2-dimethyl-4-trifluoromethyl-[1,3] dioxolan-4-yl)-1,1-dimethylethyl]-2,3-dihydrobenzofuran
  参考文献：
  名称：

  Non-steroidal dissociated glucocorticoid agonists: indoles as A-ring mimetics and function-regulating pharmacophores

  摘要：

  We report a SAR of non-steroidal glucocorticoid mimetics that utilize indoles as A-ring mimetics. Detailed SAR is discussed with a focus on improving PR and MR selectivity, GR agonism, and in vitro dissociation profile. SAR analysis led to compound (R)-33 which showed high PR and MR selectivity, potent agonist activity, and reduced transactivation activity in the MMTV and aromatase assays. The compound is equipotent to prednisolone in the LPS-TNF model of inflammation. In mouse CIA, at 30 mg/kg compound (R)-33 inhibited disease progression with an efficacy similar to the 3 mg/kg dose of prednisolone. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.018
• 作为产物：
  描述：

  3,3,3-三氟丙酮酸乙酯 在 aluminum (III) chloride 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 生成 4-(5-bromo-2,3-dihydrobenzofuran-7-yl)-2-hydroxy-4-methyl-2-trifluoromethylpentanoic acid ethyl ester
  参考文献：
  名称：

  Non-steroidal dissociated glucocorticoid agonists: indoles as A-ring mimetics and function-regulating pharmacophores

  摘要：

  We report a SAR of non-steroidal glucocorticoid mimetics that utilize indoles as A-ring mimetics. Detailed SAR is discussed with a focus on improving PR and MR selectivity, GR agonism, and in vitro dissociation profile. SAR analysis led to compound (R)-33 which showed high PR and MR selectivity, potent agonist activity, and reduced transactivation activity in the MMTV and aromatase assays. The compound is equipotent to prednisolone in the LPS-TNF model of inflammation. In mouse CIA, at 30 mg/kg compound (R)-33 inhibited disease progression with an efficacy similar to the 3 mg/kg dose of prednisolone. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.09.018

文献信息

• Universal building blocks and support media for synthesis of oligonucleotides and their analogs
  申请人：——

  公开号：US20040152905A1

  公开（公告）日：2004-08-05

  Compounds for the synthesis of oligomeric compounds, particularly oligonucleotides and chemically modified oligonucleotide analogs, are provided. In addition, methods for functionalization of a support medium with a first monomeric subunit and methods for the synthesis of oligomeric compounds utilizing the novel compounds bound to support media are provided.

  提供用于合成寡聚化合物，特别是寡核苷酸和化学修饰的寡核苷酸类似物的化合物。此外，还提供了将支持介质功能化为第一单体亚基的方法，以及利用与支持介质结合的新化合物合成寡聚化合物的方法。
• [EN] 1-PROPANOL AND 1-PROPYLAMINE DERIVATIVES AND THEIR USE AS GLUCOCORTICOID LIGANDS<br/>[FR] DERIVES DE 1-PROPANOL ET 1-PROPYLAMINE ET LEUR UTILISATION EN TANT QUE LIGANDS DE GLUCOCORTICOIDE
  申请人：BOEHRINGER INGELHEIM PHARMA

  公开号：WO2004063163A1

  公开（公告）日：2004-07-29

  Compounds of Formula (I) wherein R1, R2 R3, R4, R5, R6, and X are as defiend herein for Formula (IA) and Formula (IB), or a tautomer, prodrug, solvate, or salt thereof; pharmaceutical compositions containing such compounds, and methods of modulating the glucocoricoid receptor function and methods of treating disease-states or conditions mediated by the glucocorticoid receptor function or characterized by inflammatory, allergic, or proliferative processes in a patient using these compounds.

  式(I)的化合物，其中R1、R2、R3、R4、R5、R6和X如式(IA)和式(IB)中所定义，或其异构体、前药、溶剂化合物或盐；含有这些化合物的药物组合物，以及使用这些化合物调节糖皮质激素受体功能的方法，以及使用这些化合物治疗由糖皮质激素受体功能介导或以炎症、过敏或增殖过程为特征的疾病状态或病况的方法。
• [EN] GLUCOCORTICOID MIMETICS, METHODS OF MAKING THEM, PHARMACEUTICAL COMPOSITIONS, AND USES THEREOF<br/>[FR] MIMETIQUES DU GLUCOCORTICOIDE, PROCEDES DE FABRICATION DE CES MIMETIQUES, COMPOSITIONS PHARMACEUTIQUES ET LEURS UTILISATIONS
  申请人：BOEHRINGER INGELHEIM PHARMA

  公开号：WO2003082787A1

  公开（公告）日：2003-10-09

  Compounds of Formula (IA) and Formula (IB) wherein R1, R2, R3, R4, R5, and R6 are as defined herein for Formula (IA) or Formula (IB), or a tautomer, prodrug, solvate,or salt thereof; pharmaceutical compositions containing such compounds, and methods of modulating the glucocorticoid receptor function and methods of treating disease-states or conditions mediated by the glucocorticoid receptor function or characterized by inflammatory, allergic, or proliferative processes in a patient using these compounds.

  式（IA）和式（IB）的化合物，其中R1、R2、R3、R4、R5和R6如本说明所定义的适用于式（IA）或式（IB），或其互变异构体、前药、溶剂化合物或盐；含有这些化合物的药物组合物，以及利用这些化合物调节糖皮质激素受体功能的方法、治疗由糖皮质激素受体功能介导的疾病状态或病情特征或患者体内的炎症、过敏或增殖过程的方法。
• Glucocorticoid mimetics, methods of making them, pharmaceutical compositions, and uses thereof
  申请人：Boehringer Ingelheim Pharmaceuticals, Inc.

  公开号：US20040029932A1

  公开（公告）日：2004-02-12

  Compounds of Formula (IA) and Formula (IB) 1 wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are as defined herein for Formula (IA) or Formula (IB), or a tautomer, prodrug, solvate, or salt thereof; pharmaceutical compositions containing such compounds, and methods of modulating the glucocorticoid receptor function and methods of treating disease-states or conditions mediated by the glucocorticoid receptor function or characterized by inflammatory, allergic, or proliferative processes in a patient using these compounds.

  化合物的公式（IA）和公式（IB）1，其中R1、R2、R3、R4、R5和R6如公式（IA）或公式（IB）所定义，或其互变异构体、前药、溶剂化物或盐；包含这些化合物的药物组合物；以及使用这些化合物调节糖皮质激素受体功能、治疗由糖皮质激素受体功能介导或以炎症、过敏或增生过程为特征的疾病状态或情况的方法。
• GLUCOCORTICOID MIMETICS, METHODS OF MAKING THEM, PHARMACEUTICAL COMPOSITIONS, AND USES THEREOF
  申请人：BOEHRINGER INGELHEIM PHARMACEUTICALS INC.

  公开号：EP1490317A1

  公开（公告）日：2004-12-29