3-methoxymethyl-2,5,9-trimethyl-furo[3,2-g]chromen-7-one | 62442-60-8

• 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-methoxymethyl-2,5,9-trimethyl-furo[3,2-g]chromen-7-one
• 英文别名: 4'-methoxymethyl-4,5',8-trimethyl psoralen；4'-Methoxymethyl-4,5'8-trimethylpsoralen；7H-Furo(3,2-g)(1)benzopyran-7-one, 3-(methoxymethyl)-2,5,9-trimethyl-；3-(methoxymethyl)-2,5,9-trimethylfuro[3,2-g]chromen-7-one
• CAS: 62442-60-8
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: UPAKHQWBZFCLMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-二甲基-2-丁烯 、 3-methoxymethyl-2,5,9-trimethyl-furo[3,2-g]chromen-7-one 以 苯 为溶剂， 以21%的产率得到6-(methoxymethyl)-2,5,10,11,11,12,12-heptamethyl-4,15-dioxatetracyclo[7.6.0.03,7.010,13]pentadeca-1(9),2,5,7-tetraen-14-one
  参考文献：
  名称：

  Hager, Alicia J.; Evans, Sheryl P.; Otsuki, Tetsuo, Chemistry Letters, 1990, # 3, p. 409 - 412

  摘要：

  DOI：
• 作为产物：
  描述：

  4,5‘,8-三甲基]补骨脂素 在 溶剂黄146 作用下， 反应 6.0h， 生成 3-methoxymethyl-2,5,9-trimethyl-furo[3,2-g]chromen-7-one
  参考文献：
  名称：

  Alkoxypsoralens, Novel Nonpeptide Blockers of Shaker-Type K⁺ Channels:  Synthesis and Photoreactivity

  摘要：

  A series of psoralens and structurally related 5,7-disubstituted coumarins was synthesized and investigated for their K+ channel blocking activity as well as for their phototoxicity to Artemia salina and their ability to generate singlet oxygen and to photomodify DNA. After screening the compounds on Ranvier nodes of the toad Xenopus Laevis, the affinities of the most promising compounds, which proved to be psoralens bearing alkoxy substituents in the 5-position or alkoxymethyl substituents in the neighboring 4- or 4'-position, to a number of homomeric K+ channels were characterized. All compounds exhibited the highest affinity to Kv1.2. 5,8-Diethoxypsoralen (10d) was found to be an equally potent inhibitor of Kv1.2 and Kv1.3, while lacking the phototoxicity normally inherent in psoralens. The reported compounds represent a novel series of nonpeptide blockers of Shaker-type K+ channels that could be further developed into selective inhibitors of Kv1.2 or Kv1.3.

  DOI：

  10.1021/jm981032o

文献信息

• Psoralens
  申请人：Hoffmann-La Roche Inc.

  公开号：US04124598A1

  公开（公告）日：1978-11-07

  New psoralen compounds have been synthesized. The compounds all include the addition of substituent groups at the 4' position on the basic trioxsalen structure. Specifically, the compounds have the structure: ##STR1## wherein X may be any desired substituent such as halogenated alkyls, alcohols, ethers, aminoalkyls, etc. The new substituted psoralens exhibit high solubility in aqueous solution and low dissociation constants from deoxyribonucleic acid (DNA), as well as a reactivity with ribonucleic acids (RNA). Such psoralen compounds find use in the study of secondary structures of nucleic acids; as inhibitors of RNA replication; in the inactivation of viruses; and in the photo chemotherapy of psoriasis.

  新的苦参素化合物已经合成。这些化合物都包括在基本的三氧苯并结构的4'位置上添加取代基团。具体来说，这些化合物具有以下结构：##STR1## 其中X可以是任何所需的取代基团，如卤代烷基，醇，醚，氨基烷基等。这些新的取代苦参素在水溶液中具有高溶解度，并且从脱氧核糖核酸（DNA）中具有低离解常数，以及与核糖核酸（RNA）反应性。这些苦参素化合物可用于研究核酸的二级结构；作为RNA复制的抑制剂；在病毒灭活中使用；以及在牛皮癣的光化学治疗中使用。
• Chloroquine coupled nucleic acids and methods for their synthesis
  申请人：Kosak M. Kenneth

  公开号：US20060040879A1

  公开（公告）日：2006-02-23

  This invention discloses compositions and methods for preparing chloroquine-coupled nucleic acid compositions. The prior art has shown that chloroquines given as free drug in high enough concentration, enhances the release of various agents from cellular endosomes into the cytoplasm. The purpose of these compositions is to provide a controlled amount of chloroquine at the same site where the nucleic acid needs to be released, thereby reducing the overall dosage needed. The compositions comprise a chloroquine substance coupled to a nucleic acid directly or through a variety of pharmaceutical carrier substances. The carrier substances include polysaccharides, synthetic polymers, proteins, micelles and other substances for carrying and releasing the chloroquine compositions in the body for therapeutic effect. The compositions can also include a biocleavable linkage for carrying and releasing nucleic acids for therapeutic or other medical uses. The invention also discloses nucleic acid carrier compositions that are coupled to targeting molecules for targeting the delivery of nucleic acids to their site of action.

  本发明披露了制备氯喹偶联核酸组合物的组成和方法。先前的研究表明，以足够高的浓度给予氯喹作为自由药物，可以增强细胞内体内各种物质从内体泡中释放到细胞质中。这些组合物的目的是在核酸需要释放的同一位置提供受控量的氯喹，从而降低所需的总剂量。该组合物包括直接或通过各种药物载体物质偶联的氯喹物质和核酸。载体物质包括多糖、合成聚合物、蛋白质、胶束和其他用于在体内携带和释放氯喹组合物以达到治疗效果的物质。该组合物还可以包括生物可降解连接来携带和释放用于治疗或其他医疗用途的核酸。本发明还披露了偶联到靶向分子的核酸载体组合物，用于将核酸传递到其作用位置。
• Inactivated target cells, methods of using same and vaccines and diagnostic kits containing same
  申请人：Kronenberg, Lee H.

  公开号：EP0066886A2

  公开（公告）日：1982-12-15

  The present invention describes the inactivation of target cells by treatment of said cells with psoralens and irradiation with long wave length ultraviolet light. The inactivated cells are shown to be antigenic and are shown to be non-infective. These cells are useful as target antigens for in vitro assays of cellular immunity. Diagnostic kits containing the inactivated, target cells are prepared for use in serologic assays. Since the inactivated cells are immunogenic and non-infective, they are also useful as vaccines.

  本发明描述了用补骨脂素处理靶细胞并用长波紫外线照射使其失活的方法。灭活细胞具有抗原性和非感染性。这些细胞可作为细胞免疫体外检测的目标抗原。含有灭活靶细胞的诊断试剂盒可用于血清学检测。由于灭活细胞具有免疫原性和非感染性，因此也可用作疫苗。
• Photochemical decontamination treatment of whole blood or blood components
  申请人：DIAMOND SCIENTIFIC CO.

  公开号：EP0124363A2

  公开（公告）日：1984-11-07

  Biological compositions are freed of functional polynucleotides by treatment of the biological composition with psoralen derivatives under irradiation conditions in which the proteins retain their original physiological activities and any polynucleotide present is rendered inactive.

  在辐照条件下，用补骨脂素衍生物处理生物组合物，使蛋白质保持其原有的生理活性，而存在的任何多核苷酸则失去活性，从而使生物组合物中的功能性多核苷酸消失。
• Canine distemper virus vaccine
  申请人：DIAMOND SCIENTIFIC CO.

  公开号：EP0506147A2

  公开（公告）日：1992-09-30

  A vaccine composition for animals susceptible to infection by canine distemper virus is disclosed. The vaccine comprises an immunologically effective amount of an inactivated canine distemper virus in combination with a non-toxic pharmaceutically acceptable immunologic adjuvant, inactivation of the canine distemper virus being effected by exposure of the virus to long wavelength ultraviolet light ultraviolet radiation or gamma radiation in the presence of a furocoumarin.

  本发明公开了一种用于易受犬瘟热病毒感染的动物的疫苗组合物。该疫苗由免疫有效量的灭活犬瘟热病毒与无毒的药学上可接受的免疫佐剂组合而成，灭活犬瘟热病毒的方法是在呋喃香豆素的存在下，将病毒暴露于长波长紫外线或伽马射线中。