3-Methyl-6-isopropoxyxanthone | 155726-26-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-Methyl-6-isopropoxyxanthone
• 英文别名: 3-Methyl-6-propan-2-yloxyxanthen-9-one
• CAS: 155726-26-4
• 化学式: C₁₇H₁₆O₃
• 分子量: 268.312
• InChiKey: KLWFPRSIQDQPPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Methyl-6-isopropoxyxanthone 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 乙腈 为溶剂， 反应 12.0h， 生成 3-(1H-imidazol-1-yl)methyl-6-isopropoxy-9H-xanthen-9-one
  参考文献：
  名称：

  Drifting of heme-coordinating group in imidazolylmethylxanthones leading to improved selective inhibition of CYP11B1

  摘要：

  An abnormal increase in glucocorticoid levels is responsible for pathological disorders affecting different organs and systems, and the selective inhibition of appropriate steroidogenic enzymes represents a validated strategy to restore their physiological levels. In continuing, our studies on CYP11B inhibitors, in this paper a small series of 6-substituted 3-imidazolylmethylxanthones was designed and synthesized, according to the data acquired from previously reported series of derivatives and from a purposely-performed docking study. The new compounds proved to be potent inhibitors of CYP11B isoforms, being effective on CYP1161 in the low nanomolar range and improving selectivity with respect to CYP11B2, compared to previously reported related compounds. These data further confirmed that a suitable mutual arrangement of the imidazolylmethyl pharmacophore and a properly selected substituent on the xanthone core allows a fine tuning of the activity towards the different CYPs and further corroborate the role of the xanthone scaffold as a privileged structure in this field. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.07.078

文献信息

• Xanthone derivatives, their preparation and use
  申请人：INVERNI DELLA BEFFA S.P.A.

  公开号：EP0586960B1

  公开（公告）日：1996-02-07
• US5516794A
  申请人：——

  公开号：US5516794A

  公开（公告）日：1996-05-14