4'-(3''-hydroxypropoxy)methyl-4,5',8-trimethylpsoralen | 1137979-28-2

• 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
• 英文名称: 4'-(3''-hydroxypropoxy)methyl-4,5',8-trimethylpsoralen
• 英文别名: 4'-GAMMA-HYDROXYPROPOXYMETHYL-4,5',8-TRIMETHYLPSORALEN；3-(3-Hydroxypropoxymethyl)-2,5,9-trimethylfuro[3,2-g]chromen-7-one
• CAS: 1137979-28-2
• 化学式: C₁₈H₂₀O₅
• 分子量: 316.354
• InChiKey: TUGXRUAACIHYNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  68.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4'-(3''-hydroxypropoxy)methyl-4,5',8-trimethylpsoralen 在 吡啶 、 四氯化碳 、 三苯基膦 作用下， 反应 6.0h， 以94%的产率得到4'-(3''-chloropropoxy)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：

  3-氯甲基-2,5,9-三甲基-7H-呋喃并[3,2-g][1]苯并吡喃-7-酮 、 1,3-丙二醇 以83%的产率得到4'-(3''-hydroxypropoxy)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

文献信息

• 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。
• Synthesis of antisense oligonucleotides containing 2′-O-psoralenylmethoxyalkyl adenosine for photodynamic regulation of point mutations in RNA
  作者：Maiko Higuchi、Akio Kobori、Asako Yamayoshi、Akira Murakami

  DOI：10.1016/j.bmc.2008.12.001

  日期：2009.1

  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.