4,8-dimethyl-4'-iodomethyl-4',5'-dihydropsoralen | 273409-83-9

• 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
• 英文名称: 4,8-dimethyl-4'-iodomethyl-4',5'-dihydropsoralen
• 英文别名: 4,8-Dimethyl-4'-(iodomethyl)-4',5'-dihydropsoralen；3-(Iodomethyl)-5,9-dimethyl-2,3-dihydrofuro[3,2-g]chromen-7-one
• CAS: 273409-83-9
• 化学式: C₁₄H₁₃IO₃
• 分子量: 356.16
• InChiKey: WUYGZCDBOCXWNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 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：
  3

反应信息

• 作为反应物：
  描述：

  4,8-dimethyl-4'-iodomethyl-4',5'-dihydropsoralen 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到3-bromo-4,8-dimethyl-4'-iodomethyl-4',5'-dihydropsoralen
  参考文献：
  名称：

  4,8-二甲基-4'-（N-吡啶-甲基）-4'，5'-二氢补骨脂素的合成方法及其对 PAM 212 角质形成细胞的活性

  摘要：

  Synthetic approaches to novel 4,8-dimethyl-4'-halomethyl-4',5'-dihydropsoralens as synthetic precursors to 4,8-dimethyl-4'-(N-pyridiniummethyl)-4',5'-dihydropsoralens are described. The compounds are potential therapeutic agents for improved psoralen ultraviolet radiation therapy with reduced mutagenicity.

  DOI：

  10.3987/com-01-9197
• 作为产物：
  描述：

  7-羟基-4,8-二甲基香豆素 在 盐酸 、 tin 、 tetrafluoroboric acid 、 硫酸 、 碘 、 硝酸 、 potassium carbonate 、 sodium iodide 、 tin(ll) chloride 、 sodium nitrite 作用下， 以 乙醇 、 水 、 二甲基亚砜 、 丙酮 为溶剂， 反应 3.5h， 生成 4,8-dimethyl-4'-iodomethyl-4',5'-dihydropsoralen
  参考文献：
  名称：

  4,8-二甲基-4'-（N-吡啶-甲基）-4'，5'-二氢补骨脂素的合成方法及其对 PAM 212 角质形成细胞的活性

  摘要：

  Synthetic approaches to novel 4,8-dimethyl-4'-halomethyl-4',5'-dihydropsoralens as synthetic precursors to 4,8-dimethyl-4'-(N-pyridiniummethyl)-4',5'-dihydropsoralens are described. The compounds are potential therapeutic agents for improved psoralen ultraviolet radiation therapy with reduced mutagenicity.

  DOI：

  10.3987/com-01-9197

文献信息

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

  公开号：EP1144417A1

  公开（公告）日：2001-10-17
• US6177424B1
  申请人：——

  公开号：US6177424B1

  公开（公告）日：2001-01-23
• [EN] 4'-SUBSTITUTED-4',5'-DIHYDROPSORALENS AND THERAPEUTICAL USES THEREOF<br/>[FR] DIHYDROPSORALENES-4', 5' SUBSTITUES EN POSITION 4 ET LEURS UTILISATIONS THERAPEUTIQUES
  申请人：BUCKMAN LABOR INC

  公开号：WO2000032603A1

  公开（公告）日：2000-06-08

  The invention relates to 4'-substituted-4',5'-dihydropsoralen compounds of formula (V). In the formula R is hydrogen, a halogen, CN or an acyl group; T is a halogen, CN, a carboalkoxy group NR?1R2, or (N+R1R2R3)X-, R1 and R2¿ are independently a C¿1?-C6 alkyl, or R?1 and R2¿ together with the nitrogen form a 5-8 member heterocyclic ring, or when T is (N?+R1R2R3)X-, R1 and R2¿ together with the nitrogen form a 5-8 member heterocyclic ring or heterocyclic aromatic ring; R3 is hydroge, a C¿1?-C12 alkyl, or, when R?1 and R2¿ together with the nitrogen form a heterocyclic aromatic ring, R3 is a double bond within the heterocyclic aromatic ring; X is a halide. In another embodiment, the invention relates to processes for preparing 4'-substituted-4',5'-dihydropsoralen compounds described above. The compounds of the invention have beneficial pharmaceutical properties and can be used alone or in pharmaceutical compositions used to treat a proliferative skin disorder and to treat microbial infections in a mammal by administering to the mammal an effective amount of a compound of the invention and then irradiating the mammal with ultraviolet light.
• Synthetic Approaches to 4,8-Dimethyl-4’-(N-pyridinium-methyl)-4’,5’-dihydropsoralens and Their Activity against PAM 212 Keratinocytes
  作者：Marilyn Whittemore、Ned Heindel、Christophe Guillon、Thomas McNeel、Robert Rapp、Thomas Mariano、Diane Heck、Jeffrey Laskin

  DOI：10.3987/com-01-9197

  日期：——

  Synthetic approaches to novel 4,8-dimethyl-4'-halomethyl-4',5'-dihydropsoralens as synthetic precursors to 4,8-dimethyl-4'-(N-pyridiniummethyl)-4',5'-dihydropsoralens are described. The compounds are potential therapeutic agents for improved psoralen ultraviolet radiation therapy with reduced mutagenicity.