3-(2-羟基乙氧基甲基)-2,5,9-三甲基呋喃并[3,2-g]色烯-7-酮 | 78318-60-2

• 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-(2-羟基乙氧基甲基)-2,5,9-三甲基呋喃并[3,2-g]色烯-7-酮
• 英文名称: 4-(<β-hydroxyethoxy>methyl)-4,5',8-trimethylpsoralen
• 英文别名: 4'-(2-hydroxyethoxy)methyl-4,5',8-trimethyl-psoralen；4’-[(4-hydroxy-2-oxa)butyl]-4,5’,8-trimethylpsoralen；4'-beta-hydroxyethoxymethyl-4,5',8-trimethylpsoralen；4'-(4-hydroxy-2-oxa)butyl-4,5',8-trimethylpsoralen；3-(2-Hydroxy-ethoxymethyl)-2,5,9-trimethyl-furo[3,2-G]chromen-7-one；3-(2-hydroxyethoxymethyl)-2,5,9-trimethylfuro[3,2-g]chromen-7-one
• CAS: 78318-60-2
• 化学式: C₁₇H₁₈O₅
• 分子量: 302.327
• InChiKey: RMFGDCBXXBBDHA-UHFFFAOYSA-N

物化性质

• 熔点：
  151-152 °C
• 沸点：
  502.8±50.0 °C(Predicted)
• 密度：
  1.271±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  68.9
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  3-(2-羟基乙氧基甲基)-2,5,9-三甲基呋喃并[3,2-g]色烯-7-酮 在 吡啶 、 四氯化碳 、 三苯基膦 作用下， 反应 7.0h， 以87%的产率得到4'-(2''-chloroethoxy)methyl-4,5',8-trimethylpsoralen
  参考文献：
  名称：

  Synthesis of antisense oligonucleotides containing 2′-O-psoralenylmethoxyalkyl adenosine for photodynamic regulation of point mutations in RNA

  摘要：

  2'-O-Psoralen-conjugated antisense oligonucleotide was able to recognize a point mutation of mRNA. It had outstanding ability to photo-cross-link only to oligoribonucleotides (ORN) having a point mutation. This type of antisense molecule is the only one of its kind so far. To give high photo-cross-linking efficiency and sequence selectivity to antisense molecules, we synthesized novel photo-reactive oligonucleotides (2'-Ps-xom) containing psoralen at the 2'-O-position adenosine via an ethoxymethylene (2'-Pseom), propoxymethylene (2'-Ps-pom) and butoxymethylene (2'-Ps-bom) linker, respectively. We evaluated the photo-cross-linking efficiency and sequence selectivity in photo-cross-linking of 2'-Ps-xom to the complementary ORN and to an ORN having a mismatch base. Among them, 2'-Ps-eom exhibited superior photo-cross-linking efficiency with high sequence selectivity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.12.001
• 作为产物：
  描述：

  4,5‘,8-三甲基]补骨脂素 在 盐酸 作用下， 以 水 、 丙酮 为溶剂， 反应 16.0h， 生成 3-(2-羟基乙氧基甲基)-2,5,9-三甲基呋喃并[3,2-g]色烯-7-酮
  参考文献：
  名称：

  用于高效、多功能 miRNA-mRNA 交联的 miRNA 探针迷你文库的设计和应用

  摘要：

  MicroRNA 构成一类影响细胞内各种过程的内源性非编码 RNA。通过与目标信使 RNA 3' 非翻译区的部分互补位点进行碱基配对，microRNA 参与大多数人类蛋白质编码基因的转录后调控。它们的失调与许多病理过程和疾病有关。因此，深入了解 microRNA 的作用机制至关重要。在这里，我们提出了探针设计的新概念，以实现高效且与序列无关的 miRNA-mRNA 交联。新策略基于针对所选miRNA使用受控探针混合物，其中通过短的基于寡聚乙二醇的接头将trioxsalen部分引入所选胞苷的N 4 -位置。使用感兴趣的 microRNA 探针微型文库进行的体外光交联实验显示出不同的交联效率，证明了所提出方法的普遍适用性。

  DOI：

  10.1002/chem.202101171

文献信息

• Methods and devices for the removal of psoralens from blood products
  申请人：Cerus Corporation

  公开号：US06544727B1

  公开（公告）日：2003-04-08

  Methods and devices for the removal of psoralens and psoralen photoproducts from blood products are described. The methods include contacting a psoralen- and irradiation-treated blood product with a resin capable of adsorbing psoralens and psoralen photoproducts. The removal process is particularly suitable for use with platelet concentrates and plasma because the process does not have a significant adverse effect on clotting factor function. The methods and devices can be incorporated with apheresis systems and other devices and procedures currently used to process blood products for transfusion.

  描述了用于从血液制品中去除紧性素和紧性素光产物的方法和设备。这些方法包括将经紧性素处理和照射处理的血液制品与能够吸附紧性素和紧性素光产物的树脂接触。去除过程特别适用于血小板浓缩物和血浆，因为该过程对凝血因子功能没有显着不良影响。这些方法和设备可以与目前用于处理输血血液制品的分离系统和其他设备和程序结合使用。
• 4'-Substituted-4,5',8-trialkylpsoralens
  申请人：Thomas C. Elder, Inc.

  公开号：US04269852A1

  公开（公告）日：1981-05-26

  The invention relates to 4,5',8-trialkylpsoralens, having a substituent on the 4' carbon atom which is selected from hydroxyalkoxyalkyl and hydroxyalkylaminoalkyl, which are characterized by enhanced photosensitizing activity, especially oral activity, including comparable maxima, early onset, and especially rapid decline, as well as low toxicity, when contrasted with psoralens of different structure.

  该发明涉及4,5',8-三烷基潘豆素，其在4'碳原子上具有从羟烷氧基烷基和羟基氨基烷基中选择的取代基，其具有增强的光敏活性，特别是口服活性，包括与不同结构的潘豆素相比具有可比的最大值、早期开始和尤其迅速下降，以及低毒性。
• Reactions of furocoumarins. II. Synthetic aminomethyl psoralens<i>via</i>chloromethylation or benzylic bromination
  作者：Kurt D. Kaufman、Dennis J. Erb、Thomas M. Blok、Robert W. Carlson、Donald J. Knoechel、Lincoln Mcbride、Thomas Zeitlow

  DOI：10.1002/jhet.5570190515

  日期：1982.9

  Several psoralen derivatives have been synthesized in order to evaluate their efficacy as photochemotherapeutic (PUVA) agents, including a variety of 4′-substituted-4,5′,8-trimethypsoralen compounds (1d-j). Improved synthesis of the very potent photosensitizers 8-methylpsoralen (6a) and 4,8-dimethylpsoralen (6b) are described and 6a has been shown to undergo formylation in the 4′-position. Free radical

  为了评估其作为光化学治疗剂（PUVA）的功效，已经合成了几种补骨脂素衍生物，包括各种4'-取代的-4,5'，8-三甲基补骨脂素化合物（1d-j）。改进的非常有效的光敏剂8 methylpsoralen（合成6A）和4,8- dimethylpsoralen（图6b）中描述和图6a已被证明在4'-位经历甲酰化。用NBS对6a和6b进行的自由基溴化作用主要产生8-溴甲基衍生物（8a和d），这些衍生物很容易转化为8-氨基甲基衍生物（8c和f）的方法。如果4'-位被阻断，则亲电取代显然主要发生在补骨脂素系统的5'-位。至少，4′-甲基补骨脂素（9）的氯甲基化主要提供5′-氯甲基衍生物（10a和d），这也导致氨基甲基补骨脂素（10c和f）。
• Method and devices for the removal of psoralens from blood products
  申请人：——

  公开号：US20020115585A1

  公开（公告）日：2002-08-22

  Method for removing a pathogen-inactivating compound such as psoralen from a biological fluid such as blood or a blood product. One such method involves treating a blood product which contains a nucleic acid-containing pathogen to be inactivated. This method includes adding a pathogen-inactivating compound such as psoralen to the blood product; irradiating the psoralen and the blood product to form a mixture comprising the blood product, free psoralen, and low molecular weight psoralen photoproducts; and contacting the mixture with a hypercrosslinked resin to remove at least substantially all of the free psoralen and the low molecular weight psoralen photoproducts. A hypercrosslinked resin in this method preferably eliminates a wetting step that a number of other types of resins require before being used to adsorb the pathogen inactivating compound.

  从生物液体（如血液或血液制品）中去除一种病原体灭活化合物（如紫荆素）的方法。其中一种方法涉及处理含有核酸病原体的血液制品以进行灭活。该方法包括向血液制品中添加病原体灭活化合物（如紫荆素）；照射紫荆素和血液制品以形成含有血液制品、游离紫荆素和低分子量紫荆素光产物的混合物；并将该混合物与超交联树脂接触，以去除至少几乎所有的游离紫荆素和低分子量紫荆素光产物。在该方法中，超交联树脂优选地消除了其他类型的树脂在用于吸附病原体灭活化合物之前需要进行的浸润步骤。
• Method for inactivating pathogens in blood using photoactivation of
  申请人：Cerus Corporation

  公开号：US05593823A1

  公开（公告）日：1997-01-14

  Psoralen compounds are synthesized which have substitutions on the 4, 4', 5', and 8 positions of the psoralen, which permit enhanced binding to nucleic acid of pathogens. Higher psoralen binding levels and lower mutagenicity are described, resulting in safer, more efficient, and reliable inactivation of pathogens in blood products. The invention contemplates inactivation methods using the new psoralens which do not compromise the function of blood products for transfusion.

  合成了带有取代基的苯麻酚化合物，这些取代基位于苯麻酚的4、4'、5'和8位，使其能够更好地结合病原体的核酸。描述了更高的苯麻酚结合水平和更低的致突变性，从而在血液制品中更安全、更高效、更可靠地灭活病原体。该发明考虑了使用新苯麻酚进行灭活的方法，这些方法不会损害用于输血的血液制品的功能。