3-fluoro-4,8-dimethyl-5'-iodomethyl-4',5'-dihydrofurocoumarin

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-fluoro-4,8-dimethyl-5'-iodomethyl-4',5'-dihydrofurocoumarin
• 英文别名: 3-Fluoro-4,8-dimethyl-5'-(iodomethyl)-4',5'-dihydropsoralen；6-Fluoro-2-(iodomethyl)-5,9-dimethyl-2,3-dihydrofuro[3,2-g]chromen-7-one
• 化学式: C₁₄H₁₂FIO₃
• 分子量: 374.15
• InChiKey: HLZOGNOCCHPDAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-fluoro-4,8-dimethyl-6-allyl-7-hydroxycoumarin 在 N-碘代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以91%的产率得到3-fluoro-4,8-dimethyl-5'-iodomethyl-4',5'-dihydrofurocoumarin
  参考文献：
  名称：

  合成方法以4,8-二甲基-5' - （ñ -pyridiniummethyl） - 4'，5'- dihydropsoralens和4,8-二甲基- 5' - （ñ -氨甲基） - 4'，5'- dihydropsoralens †往最‡

  摘要：

  新的合成方法，以4,8-二甲基-5' - （ñ -pyridiniummethyl）-4'，5'- dihydropsoralens和4,8- dimemyl -5' - （ñ -氨甲基）-4'，5'- dihydropsoralens是描述。5'-卤甲基-4'，5'-二氢补骨脂素前体是通过4,8-二甲基-6-烯丙基-7-羟基香豆素的亲电闭环反应形成的。闭环反应也可以用于5'-卤代甲基-4-甲基-4'，5'-二氢血管紧张素的合成。该化合物是用于改善补骨脂素紫外线A辐射治疗的潜在治疗剂。

  DOI：

  10.1002/jhet.5570380415

文献信息

• AMINO-AND MERCURIO-SUBSTITUTED 4', 5'-DIHYDROPSORALENS AND THERAPEUTICAL USES THEREOF
  申请人：BUCKMAN LABORATORIES INTERNATIONAL, INC.

  公开号：EP1133498A2

  公开（公告）日：2001-09-19
• US6255324B1
  申请人：——

  公开号：US6255324B1

  公开（公告）日：2001-07-03
• [EN] AMINO- AND MERCURIO-SUBSTITUTED 4',5'-DIHYDROPSORALENS AND THERAPEUTICAL USES THEREOF<br/>[FR] 4',5'-DIHYDROPSORALENES AMINO ET MERCURIO SUBSTITUES ET LEURS UTILISATIONS THERAPEUTIQUES
  申请人：BUCKMAN LABOR INC

  公开号：WO2000031081A2

  公开（公告）日：2000-06-02

  5'- substituted, 4', 5'- dihydropsoralen compounds (5) bearing tertiary amines (and salts thereof), quaternary ammonium moieties or organomercurial moieties are described. Also described are 2- substituted mercurimethyl -2-3- dihydro -benzofurans of formula (7). Also reported are versatile direct syntheses through a hitherto unknown compounds such as 3-R-4, 8-dimethyl -4',5'-dihydro -5'-bromomethylpsoralen or a 3-R-4, 8-dimethyl-4, 5'-dihydro- 5'-iodomethylpsoralen to prepare a structurally diverse array of partially reduced psoralens and benzofurans. The presence of a permanent ammonium charge in these psoralens precludes membrane passage and the mono-unsaturation precludes the cross linking of nuclear DNA, thereby minimizing the mutagenic/carcinogenic side effects long associated with psoralen-derived therapies. The presence of a mercury functionality provides a reactive cell-binding group on these psoralens with unique cytotoxicity without light activation and an enhancement of cytotoxicity activity upon light activation. The invention also relates to these partially reduced and quaternized psoralens, amino-substituted psoralens, and mercurio psoralens display impressive pharmacology against PAM 212 keratinocytes, a model cell line employed as a test system to indicate epidermal cytotoxicity and cancer. The compounds of the invention also have antimicrobicidal activity useful in pharmacologic agents for mammals (e.g. the treatment of tuberculosis) as well as in controlling the growth of microorganisms on substrates and in aqueous systems.