8-(4'-bromobutyloxy)psoralen | 69150-33-0

• 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: 8-(4'-bromobutyloxy)psoralen
• 英文别名: 9-(4-bromobutyloxy)psoralen；8-((4-bromobutyl-1)oxy)psoralen；8-(4'-bromobutoxy)psoralen；9-(4-bromo-butoxy)-furo[3,2-g]chromen-7-one；9-(4-Bromobutoxy)-7H-furo[3,2-g][1]benzopyran-7-one；9-(4-bromobutoxy)furo[3,2-g]chromen-7-one
• CAS: 69150-33-0
• 化学式: C₁₅H₁₃BrO₄
• 分子量: 337.17
• InChiKey: IDYRTLALBUSZFJ-UHFFFAOYSA-N

物化性质

• 沸点：
  500.8±50.0 °C(Predicted)
• 密度：
  1.527±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  8-(4'-bromobutyloxy)psoralen 在 盐酸 、 溴 、 potassium carbonate 作用下， 以 溶剂黄146 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  Alkoxyfurocoumarin derivatives as potential mesolimbic selective antipsychotics

  摘要：

  DOI：

  10.1016/s0223-5234(97)87536-8
• 作为产物：
  描述：

  8-甲氧基补骨脂素 在 吡啶盐酸盐 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 10.42h， 生成 8-(4'-bromobutyloxy)psoralen
  参考文献：
  名称：

  Efficient Cleavage of DNA by Iron(III) Triazacyclononane Derivatives

  摘要：

  Compounds based on (1,4,7-trimethyl-1,4,7-triazacyclononane)iron(III) chloride have been synthesized. Exceedingly low concentrations (approximately 0.5 mu M) of these reagents are required to effect single-stranded oxidative cleavage of plasmid DNA at physiological pH and temperature. Approximately 3 breaks per plasmid per micromolar of reagent occur in 1 h at 37 degrees C. The addition of dithiothreitol dramatically increased the effectiveness of these compounds; only 0.05 mu M of reagent was required for DNA cleavage. When psoralen (a DNA photocross-linking agent) was attached to the iron complex, irradiation further increased the cleavage efficiency. The DNA cleaving abilities rival those of the cytotoxic antitumor drug bleomycin. Unlike bleomycin, the synthetic agents cut DNA with little sequence specificity. The lability of the chloride ligands, the hard acid character of iron(III), and the absence of base specificity in the DNA cleaving reaction suggest that a cationic iron species binds to the phosphate backbone of DNA. The reaction's dependence on reductants and dissolved oxygen suggests that it proceeds by a redox mechanism. Crystals of (1,4,7-trimethyl-1,4,7-triazacyclononane)FeCl3) (L'FeCl3) belong to the monoclinic space group P2(1)/c, with a = 12.321(2)Angstrom, b = 7.3220(10) Angstrom, c = 15.903(3) Angstrom, V = 1434.7(5) Angstrom(3), and Z = 4 at 293 K. Refinement of 145 least squares parameters for 2613 independent reflections with F > 4.0 sigma(F) converged to R = 3.43% and R(W) = 6.45%. The coordination geometry around iron(III) approximates a trigonally distorted octahedron. The N-Fe-N bond angles (77.8 degrees-78.8 degrees) are compressed, while the Cl-Fe-Cl angles (96.7 degrees-97.0 degrees) are expanded from the octahedral value.

  DOI：

  10.1021/ja00119a013

文献信息

• Photochemical and Photobiological Properties of New Bispsoralen Derivatives (Bis[PsCn]PIP, n = 4, 6, 8)¶
  作者：Sung Ki Kim、Han Oh Park、Sang Chul Shim

  DOI：10.1562/0031-8655(2000)072<0472:pappon>2.0.co;2

  日期：——

  Bispsoralen derivatives possessing two psoralens and one piperazine molecule, 1,4-bis[n'-(8-psoralenoxy) alkyl] piperazine (Bis[PsC(n)]PIP, n = 4, 6, 8), show high water solubility, efficient intercalation into DNA and good photocrosslinking efficiency of DNA. Bis(PsC(4))PIP shows high lethality on bacteriophage T7 and can effectively inhibit the amplification of DNA by stopping the polymerase chain reactions in a short period of irradiation time.
• Synthesis and <i>In Vitro</i> Biological Evaluation of Psoralen‐Linked Fullerenes
  作者：Akiko Hashimoto、Takeji Takamura‐Enya、Yoshimitsu Oda

  DOI：10.1111/php.13138

  日期：2019.11

  AbstractPhotodynamic therapy (PDT) is a widely used medicinal treatment for the cancer therapy that utilizes the combination of a photosensitizer (PS) and light irradiation. In this study, we synthesized two novel C60 fullerene derivatives, compounds 1 and 2, with a psoralen moiety that can covalently bind to DNA molecules via cross‐linking to pyrimidine under photoirradiation. Along with several fullerene derivatives, the biological properties of several novel compounds have been evaluated. Compounds 1 and 2, which have been shown to induce the production of hydroxyl radicals using several ROS detecting reagents, induced DNA strand breaks with relatively weak activities in the in vitro detection system using a supercoiled plasmid. However, the psoralen‐bound fullerene with carboxyl groups (2) only showed genotoxicity in the genotoxicity assay system of the umu test. Compound 2 was also seen to have cytotoxic activities in several cancer cell lines at higher doses compared to water‐soluble fullerenes.
• ANTONELLO C.; MARCIANI MAGNO S.; GIA O., ATTI. IST. VENETO SCI., LETT. ED ARTI. CL. SCI. MAT. E NATUR., 1976-1977,+
  作者：ANTONELLO C.、 MARCIANI MAGNO S.、 GIA O.

  DOI：——

  日期：——
• Alkoxyfurocoumarin derivatives as potential mesolimbic selective antipsychotics
  作者：J Bondo Hansen、A Fink-Jensen、L Hansen、EB Nielsen、MA Scheideler

  DOI：10.1016/s0223-5234(97)87536-8

  日期：1997.1
• Efficient Cleavage of DNA by Iron(III) Triazacyclononane Derivatives
  作者：Gail C. Silver、William C. Trogler

  DOI：10.1021/ja00119a013

  日期：1995.4

  Compounds based on (1,4,7-trimethyl-1,4,7-triazacyclononane)iron(III) chloride have been synthesized. Exceedingly low concentrations (approximately 0.5 mu M) of these reagents are required to effect single-stranded oxidative cleavage of plasmid DNA at physiological pH and temperature. Approximately 3 breaks per plasmid per micromolar of reagent occur in 1 h at 37 degrees C. The addition of dithiothreitol dramatically increased the effectiveness of these compounds; only 0.05 mu M of reagent was required for DNA cleavage. When psoralen (a DNA photocross-linking agent) was attached to the iron complex, irradiation further increased the cleavage efficiency. The DNA cleaving abilities rival those of the cytotoxic antitumor drug bleomycin. Unlike bleomycin, the synthetic agents cut DNA with little sequence specificity. The lability of the chloride ligands, the hard acid character of iron(III), and the absence of base specificity in the DNA cleaving reaction suggest that a cationic iron species binds to the phosphate backbone of DNA. The reaction's dependence on reductants and dissolved oxygen suggests that it proceeds by a redox mechanism. Crystals of (1,4,7-trimethyl-1,4,7-triazacyclononane)FeCl3) (L'FeCl3) belong to the monoclinic space group P2(1)/c, with a = 12.321(2)Angstrom, b = 7.3220(10) Angstrom, c = 15.903(3) Angstrom, V = 1434.7(5) Angstrom(3), and Z = 4 at 293 K. Refinement of 145 least squares parameters for 2613 independent reflections with F > 4.0 sigma(F) converged to R = 3.43% and R(W) = 6.45%. The coordination geometry around iron(III) approximates a trigonally distorted octahedron. The N-Fe-N bond angles (77.8 degrees-78.8 degrees) are compressed, while the Cl-Fe-Cl angles (96.7 degrees-97.0 degrees) are expanded from the octahedral value.