O-dimethoxytrityl hexaethylene glycol monosuccinate

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: O-dimethoxytrityl hexaethylene glycol monosuccinate
• 英文别名: O-(4,4'-dimethoxytrityl)-hexaethylene glycol succinate；4-[2-[2-[2-[2-[2-[2-[Bis(4-methoxyphenyl)-phenylmethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]-4-oxobutanoic acid
• 化学式: C₃₇H₄₈O₁₂
• 分子量: 684.781
• InChiKey: ZSKPKLUVMXRKQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  49
• 可旋转键数：
  28
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  五氯酚 、 O-dimethoxytrityl hexaethylene glycol monosuccinate 在 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Biologically active oligodeoxyribonucleotides—IX.1 Synthesis and anti-HIV-1 activity of hexadeoxyribonucleotides, TGGGAG, bearing 3′- and 5′-end-modification

  摘要：

  We have determined that hexadeoxyribonucleotides (5'TGGGAG3'), with modified aromatic groups such as a trityl group at the 5'-end, have anti-HIV-1 activity in vitro. The 6-mer bearing a 3,4-dibenzyloxybenzyl (3,4-DBB) group at the 5'-end had the most potent activity and the least cytotoxicity. When the 3'-end of the 5'-(3,4-DBB)-modified 6-mer was substituted with a 2-hydroxyethylphosphate, a 2-hydroxyethylthiophosphate, or a methylphosphate group at the 3'-end, anti-HIV-1 activity increased. Moreover, among various 3'- and 5'-end-modified 6-mers that were tested, the 6-mer (R-95288) bearing a 3,4-DBB group at the 5'-end and a 2-hydroxyethylphosphate group at the 3'-end was the most stable, when incubated with mouse, rat, or human plasma. Therefore, R-95288 was chosen as the best candidate for possible use in therapy on the basis of its anti-HIV-1 activity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00161-2
• 作为产物：
  描述：

  丁二酸酐 、 O1-(二甲氧基三苯甲基)HEXA乙烯GLYCOL 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 O-dimethoxytrityl hexaethylene glycol monosuccinate
  参考文献：
  名称：

  Biologically active oligodeoxyribonucleotides—IX.1 Synthesis and anti-HIV-1 activity of hexadeoxyribonucleotides, TGGGAG, bearing 3′- and 5′-end-modification

  摘要：

  We have determined that hexadeoxyribonucleotides (5'TGGGAG3'), with modified aromatic groups such as a trityl group at the 5'-end, have anti-HIV-1 activity in vitro. The 6-mer bearing a 3,4-dibenzyloxybenzyl (3,4-DBB) group at the 5'-end had the most potent activity and the least cytotoxicity. When the 3'-end of the 5'-(3,4-DBB)-modified 6-mer was substituted with a 2-hydroxyethylphosphate, a 2-hydroxyethylthiophosphate, or a methylphosphate group at the 3'-end, anti-HIV-1 activity increased. Moreover, among various 3'- and 5'-end-modified 6-mers that were tested, the 6-mer (R-95288) bearing a 3,4-DBB group at the 5'-end and a 2-hydroxyethylphosphate group at the 3'-end was the most stable, when incubated with mouse, rat, or human plasma. Therefore, R-95288 was chosen as the best candidate for possible use in therapy on the basis of its anti-HIV-1 activity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00161-2

文献信息

• Modified oligodeoxyribonucleotides, their preparation and their therapeutic use
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0611075B1

  公开（公告）日：1996-12-18
• US5674856A
  申请人：——

  公开号：US5674856A

  公开（公告）日：1997-10-07
• US5807837A
  申请人：——

  公开号：US5807837A

  公开（公告）日：1998-09-15
• Biologically active oligodeoxyribonucleotides—IX.1 Synthesis and anti-HIV-1 activity of hexadeoxyribonucleotides, TGGGAG, bearing 3′- and 5′-end-modification
  作者：Makoto Koizumi、Rika Koga、Hitoshi Hotoda、Kenji Momota、Toshinori Ohmine、Hidehiko Furukawa、Toshinori Agatsuma、Takashi Nishigaki、Koji Abe、Toshiyuki Kosaka、Shinya Tsutsumi、Junko Sone、Masakatsu Kaneko、Satoshi Kimura、Kaoru Shimada

  DOI：10.1016/s0968-0896(97)00161-2

  日期：1997.12

  We have determined that hexadeoxyribonucleotides (5'TGGGAG3'), with modified aromatic groups such as a trityl group at the 5'-end, have anti-HIV-1 activity in vitro. The 6-mer bearing a 3,4-dibenzyloxybenzyl (3,4-DBB) group at the 5'-end had the most potent activity and the least cytotoxicity. When the 3'-end of the 5'-(3,4-DBB)-modified 6-mer was substituted with a 2-hydroxyethylphosphate, a 2-hydroxyethylthiophosphate, or a methylphosphate group at the 3'-end, anti-HIV-1 activity increased. Moreover, among various 3'- and 5'-end-modified 6-mers that were tested, the 6-mer (R-95288) bearing a 3,4-DBB group at the 5'-end and a 2-hydroxyethylphosphate group at the 3'-end was the most stable, when incubated with mouse, rat, or human plasma. Therefore, R-95288 was chosen as the best candidate for possible use in therapy on the basis of its anti-HIV-1 activity. (C) 1997 Elsevier Science Ltd.