1-(2-adamantyl)-3-(4-methoxyphenyl)urea

• 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: 1-(2-adamantyl)-3-(4-methoxyphenyl)urea
• 英文别名: 1-adamantan-2-yl-3-(4-methoxy-phenyl)-urea
• 化学式: C₁₈H₂₄N₂O₂
• 分子量: 300.401
• InChiKey: XMDMNOXHNSLROT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氨基金刚烷 、 对甲氧基苯异氰酸酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到1-(2-adamantyl)-3-(4-methoxyphenyl)urea
  参考文献：
  名称：

  The structure–activity relationship of urea derivatives as anti-tuberculosis agents

  摘要：

  The treatment of tuberculosis is becoming more difficult due to the ever increasing prevalence of drug resistance. Thus, it is imperative that novel anti-tuberculosis agents, with unique mechanisms of action, be discovered and developed. The direct anti-tubercular testing of a small compound library led to discovery of adamantyl urea hit compound 1. In this study, the hit was followed up through the synthesis of an optimization library. This library was generated by systematically replacing each section of the molecule with a similar moiety until a clear structure-activity relationship was obtained with respect to antitubercular activity. The best compounds in this series contained a 1-adamantyl-3-phenyl urea core and had potent activity against Mycobacterium tuberculosis plus an acceptable therapeutic index. It was noted that the compounds identified and the pharmacophore developed is consistent with inhibitors of epoxide hydrolase family of enzymes. Consequently, the compounds were tested for inhibition of representative epoxide hydrolases: M. tuberculosis EphB and EphE; and human soluble epoxide hydrolase. Many of the optimized inhibitors showed both potent EphB and EphE inhibition suggesting the antitubercular activity is through inhibition of multiple epoxide hydrolase enzymes. The inhibitors also showed potent inhibition of humans soluble epoxide hydrolase, but limited cytotoxicity suggesting that future studies must be towards increasing the selectivity of epoxide hydrolase inhibition towards the M. tuberculosis enzymes. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.034

文献信息

• 2-Adamantylurea derivatives as selective 11B-HSD1 inhibitors
  申请人：Merck Sante

  公开号：EP1801098A1

  公开（公告）日：2007-06-27

  The present invention relates to 2-adamantylurea derivatives of formula I as selective inhibitors of the enzyme 11-beta-hydroxysteroid dehydrogenase type 1 (11β-HSD1) and the use of such compounds for the treatment and prevention of metabolic syndrome, diabetes, insulin resistance, obesity, lipid disorders, glaucoma, osteoporosis, cognitive disorders, anxiety, depression, immune disorders, hypertension and other diseases and conditions.

  本发明涉及公式I的2-金刚烷基脲衍生物，作为选择性抑制酶11-β-羟基类固醇脱氢酶1（11β-HSD1）的药物，并利用这些化合物治疗和预防代谢综合征、糖尿病、胰岛素抵抗、肥胖、脂质紊乱、青光眼、骨质疏松症、认知障碍、焦虑、抑郁、免疫紊乱、高血压以及其他疾病和症状。
• 2-ADAMANTYLUREA DERIVATIVES AS SELECTIVE 11BETA-HSD1 INHIBITORS
  申请人：Carniato Denis

  公开号：US20090227631A1

  公开（公告）日：2009-09-10

  The present invention relates to 2-adamantylurea derivatives of formula I as selective inhibitors of the enzyme 11-beta-hydroxysteroid dehydrogenase type 1 (11β-HSD1) and the use of such compounds for the treatment and prevention of metabolic syndrome, diabetes, insulin resistance, obesity, lipid disorders, glaucoma, osteoporosis, cognitive disorders, anxiety, depression, immune disorders, hypertension and other diseases and conditions.

  本发明涉及式I的2-金刚烷基脲衍生物，作为选择性抑制酶11-β-羟基类固醇脱氢酶1型（11β-HSD1）的抑制剂及其在代谢综合征、糖尿病、胰岛素抵抗、肥胖、脂质紊乱、青光眼、骨质疏松症、认知障碍、焦虑、抑郁、免疫障碍、高血压和其他疾病和病况的治疗和预防中的应用。
• 2-ADAMANTYLUREA DERIVATIVES AS SELECTIVE 11B-HSD1 INHIBITORS
  申请人：CARNIATO Denis

  公开号：US20120172396A1

  公开（公告）日：2012-07-05

  The present invention relates to 2-adamantylurea derivatives of formula I as selective inhibitors of the enzyme 11-beta-hydroxysteroid dehydrogenase type 1 (11β-HSD1) and the use of such compounds for the treatment and prevention of metabolic syndrome, diabetes, insulin resistance, obesity, lipid disorders, glaucoma, osteoporosis, cognitive disorders, anxiety, depression, immune disorders, hypertension and other diseases and conditions.

  本发明涉及式I的2-金刚烷基脲衍生物，作为选择性抑制酶11-β-羟基类固醇脱氢酶1型（11β-HSD1）的抑制剂，并且利用这些化合物治疗和预防代谢综合征、糖尿病、胰岛素抵抗、肥胖症、脂质紊乱、青光眼、骨质疏松症、认知障碍、焦虑症、抑郁症、免疫障碍、高血压和其他疾病和病况。
• US8188288B2
  申请人：——

  公开号：US8188288B2

  公开（公告）日：2012-05-29
• US8466200B2
  申请人：——

  公开号：US8466200B2

  公开（公告）日：2013-06-18