(3'Z,4'aS)-3'-(hydroxymethylidene)-4'a-methylspiro[1,3-dioxolane-2,5'-4,6,7,8-tetrahydronaphthalene]-2'-one | 694526-50-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3'Z,4'aS)-3'-(hydroxymethylidene)-4'a-methylspiro[1,3-dioxolane-2,5'-4,6,7,8-tetrahydronaphthalene]-2'-one
• CAS: 694526-50-6
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: ZYWIVAWEAWFVFV-XPSMFNQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3'Z,4'aS)-3'-(hydroxymethylidene)-4'a-methylspiro[1,3-dioxolane-2,5'-4,6,7,8-tetrahydronaphthalene]-2'-one 在 盐酸 、 sodium acetate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 溶剂黄146 、 苯 为溶剂， 反应 29.0h， 生成 (4R,4'aS,5R)-4,5-dibutyl-1'-(4-fluorophenyl)-4'a-methylspiro[1,3-dioxolane-2,5'-4,6,7,8-tetrahydrobenzo[f]indazole]
  参考文献：
  名称：

  Novel ketal ligands for the glucocorticoid receptor: in vitro and in vivo activity

  摘要：

  A novel series of selective ligands for the human glucocorticoid receptor is described. Structure-activity studies focused on variation of B-ring size, ketal ring size, and ketal substitution. These analogs were found to be potent and selective ligands for GR and have partial agonist profiles in functional assays for transactivation (TAT, GS) and transrepression (IL-6). Of these compounds, 27, 28, and 35 were evaluated further in a mouse LPS-induced TNF-alpha secretion model. Compound 28 had an ED50 Of 14.1 mg/kg compared with 0.5 mg/kg for prednisolone in the same assay. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.027
• 作为产物：
  描述：

  (S)-(+)-3,4,8,8a-四氢-8a-甲基-1,6-(2H,7H)-萘醌 在 sodium hydride 、 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 3.5h， 生成 (3'Z,4'aS)-3'-(hydroxymethylidene)-4'a-methylspiro[1,3-dioxolane-2,5'-4,6,7,8-tetrahydronaphthalene]-2'-one
  参考文献：
  名称：

  Novel ketal ligands for the glucocorticoid receptor: in vitro and in vivo activity

  摘要：

  A novel series of selective ligands for the human glucocorticoid receptor is described. Structure-activity studies focused on variation of B-ring size, ketal ring size, and ketal substitution. These analogs were found to be potent and selective ligands for GR and have partial agonist profiles in functional assays for transactivation (TAT, GS) and transrepression (IL-6). Of these compounds, 27, 28, and 35 were evaluated further in a mouse LPS-induced TNF-alpha secretion model. Compound 28 had an ED50 Of 14.1 mg/kg compared with 0.5 mg/kg for prednisolone in the same assay. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.027

文献信息

• SELECTIVE SPIROCYCLIC GLUCOCORTICOID RECEPTOR MODULATORS
  申请人：Merck & Co., Inc.

  公开号：EP1617806B1

  公开（公告）日：2009-11-04
• 1H-benzo[F]indazol-5-YL derivatives as selective glucocorticoid receptor modulators
  申请人：Ali Amjad

  公开号：US20080076795A1

  公开（公告）日：2008-03-27

  The present invention encompasses compounds of Formula I: or pharmaceutically acceptable salts or hydrates thereof, which are useful as selective glucocorticoid receptor ligands for treating a variety of autoimmune and inflammatory diseases or conditions. Pharmaceutical compositions and methods of use are also included.
• US7282591B2
  申请人：——

  公开号：US7282591B2

  公开（公告）日：2007-10-16
• US7411073B2
  申请人：——

  公开号：US7411073B2

  公开（公告）日：2008-08-12
• US7625937B2
  申请人：——

  公开号：US7625937B2

  公开（公告）日：2009-12-01