3-氟-4,8-二甲基-7-羟基香豆素 | 105440-97-9

• 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
• 中文名称: 3-氟-4,8-二甲基-7-羟基香豆素
• 英文名称: 3-fluoro-4,8-dimethyl-7-hydroxycoumarin
• 英文别名: 3-fluoro-7-hydroxy-4,8-dimethylchromen-2-one
• CAS: 105440-97-9
• 化学式: C₁₁H₉FO₃
• 分子量: 208.189
• InChiKey: BFIYZKWJYMZLLF-UHFFFAOYSA-N

物化性质

• 熔点：
  192-193 °C
• 沸点：
  372.3±42.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-氟-4,8-二甲基-7-羟基香豆素 在 四丁基溴化铵 、 potassium carbonate 、 potassium iodide 、 sodium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 反应 6.25h， 生成 6-fluoro-2,3,5,9-tetramethyl-7H-furo[3,2-g]chromen-7-one
  参考文献：
  名称：

  补骨脂素衍生物的设计、合成和抗真菌活性

  摘要：

  已经设计并合成了一系列具有不同取代基的线性呋喃香豆素。它们的结构通过 1H-NMR 光谱、高分辨率质谱 (EI-MS)、IR 和 X 射线单晶衍射证实。在体外评估了所有目标化合物对根瘤菌、灰葡萄孢、黑链格孢、玉米赤霉、黄瓜炭疽和链格孢叶斑病的抗真菌活性，浓度为 100 μg/mL，部分设计化合物显示出潜在的抗真菌活性。化合物 3a (67.9%) 表现出比对照 Osthole (66.1%) 更高的对抗灰葡萄孢的活性。此外，化合物 4b (62.4%) 表现出与 Osthole (69.5%) 对立枯丝核菌相同的抗真菌活性。

  DOI：

  10.3390/molecules22101672
• 作为产物：
  描述：

  2-氟乙酰乙酸乙酯 、 2,6-二羟基甲苯 在 硫酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.5h， 以84%的产率得到3-氟-4,8-二甲基-7-羟基香豆素
  参考文献：
  名称：

  3-取代的5'-（N-吡啶鎓甲基）-4'，5'-二氢补骨脂素的合成方法

  摘要：

  描述了3-取代-5'-（N-吡啶鎓甲基）-4'，5'-二氢补骨脂素的新的合成方法。提出的新途径利用适当取代的香豆素和4'，5'-二氢补骨脂素。建议的化合物代表补骨脂素紫外线辐射治疗的潜在治疗剂。

  DOI：

  10.1002/jhet.5570370106

文献信息

• Amino-and mercurio-substituted 4′,5'-dihydropsoralens and therapeutical uses thereof
  申请人：——

  公开号：US06255324B1

  公开（公告）日：2001-07-03

  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 forumla (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.

  描述了带有三级胺基（及其盐）、季铵基团或有机汞基团的5′-取代、4′,5′-二氢喋啶化合物（5）。 还描述了公式（7）的2-取代汞甲基-2-3-二氢苯并呋喃类化合物。 还报道了通过迄今为止未知的化合物（如3-R-4,8-二甲基-4′,5′-二氢-5′-溴甲基喋啶或3-R-4,8-二甲基-4′,5′-二氢-5′-碘甲基喋啶）直接合成多种结构不同的部分还原喋啶和苯并呋喃。 这些喋啶中永久铵电荷的存在阻止了膜通透性，而单不饱和度阻止了核DNA的交联，从而最大程度地减少了与喋啶衍生疗法长期相关的致突变/致癌副作用。 汞功能团的存在为这些喋啶提供了具有独特细胞毒性的反应性细胞结合基团，无需光激活即可增强细胞毒性活性。 该发明还涉及这些部分还原和季铵化的喋啶、氨基取代的喋啶和汞喋啶对PAM 212角质细胞表现出令人印象深刻的药理学作用，PAM 212角质细胞是作为表皮细胞毒性和癌症指示的测试系统所采用的模型细胞系。 该发明的化合物还具有对哺乳动物有用的抗微生物活性（例如治疗结核病）以及在控制基质和水系统中微生物生长方面的作用。
• TAKAOKA, AKIO;IBRAHIM, M. KAMAL;KAGARUKI, S. R. F.;ISHIKAWA, NOBUO, J. CHEM. SOC. JAP., CHEM. AND IND. CHEM., 1985, N 11, 2169-2176
  作者：TAKAOKA, AKIO、IBRAHIM, M. KAMAL、KAGARUKI, S. R. F.、ISHIKAWA, NOBUO

  DOI：——

  日期：——
• 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.