5'-O-(2-naphthylmethyl)thymidine | 144846-02-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5'-O-(2-naphthylmethyl)thymidine
• 英文别名: 5'-O-[(naphthalen-2-yl)methyl]thymidine；1-[(2R,4S,5R)-4-hydroxy-5-(naphthalen-2-ylmethoxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 144846-02-6
• 化学式: C₂₁H₂₂N₂O₅
• 分子量: 382.416
• InChiKey: CSCWBEUTIZIKJK-IPMKNSEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  88.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-氰乙基N,N-二异丙基氯亚磷酰胺 、 5'-O-(2-naphthylmethyl)thymidine 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以60%的产率得到5'-O-(2-naphthylmethyl)thymidine 3'-O-(2-cyanoethyl N,N-diisopropyl)phosphoramidite
  参考文献：
  名称：

  Biologically Active Oligodeoxyribonucleotides - II¹: Structure Activity Relationships of Anti-HIV-1 Pentadecadeoxyribonucleotides Bearing 5′-End-Modifications

  摘要：

  5'-End-modified pentadecadeoxyribonucleotides (15mers) with a sequence complementary to the tat 2nd splicing acceptor region of human immunodeficiency virus type 1 (HIV-1) were prepared and evaluated for anti-HIV-1 activity. The structures of modified 15mers were confirmed by negative ion LSI mass spectroscopy, and the anti-HIV-1 activities were evaluated in vitro by MTT assay using MT-4 cells. While the unmodified 15mer had no activity in our assay system, the 15mers bearing modifications with trityl-type substituents at the 5'-end showed potent anti-HIV-1 activities.

  DOI：

  10.1080/15257779408012159
• 作为产物：
  描述：

  2-溴甲基萘 以33%的产率得到5'-O-(2-naphthylmethyl)thymidine
  参考文献：
  名称：

  Modified oligodeoxyribonucleoditides

  摘要：

  提供用于治疗或预防哺乳动物（可能是人类）病毒感染的化合物。这些化合物是寡脱氧核糖核酸衍生物，并提供了一种新颖的合成这些化合物的途径，以及更普遍有用的中间体。活性化合物的一般结构式为（1）：其中R.sub.1、R.sub.2和R.sub.3是氢原子、烷基、所定义的芳基和蒽醌基；Z是碳或硅；或者R.sub.2、R.sub.3和Z一起代表芴基或蒽基；R.sub.4是氢原子、所定义的烷基、所定义的芳基；Y.sub.1、Y.sub.3和Y.sub.4是氧、硫或>NH；Y.sub.2是氧、硫、>NH、烷基或苯基；X是所定义的烷基；m和n为0至10；B是链长为3至9的寡脱氧核糖核苷酸；或其盐。

  公开号：

  US05674856A1

文献信息

• EP558749
  申请人：——

  公开号：——

  公开（公告）日：——
• 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 - II¹: Structure Activity Relationships of Anti-HIV-1 Pentadecadeoxyribonucleotides Bearing 5′-End-Modifications
  作者：Hitoshi Hotoda、Kenji Momota、Hidehiko Furukawa、Takemichi Nakamura、Masakatsu Kaneko、Satcshi Kimura、Kawu Shimada

  DOI：10.1080/15257779408012159

  日期：1994.7

  5'-End-modified pentadecadeoxyribonucleotides (15mers) with a sequence complementary to the tat 2nd splicing acceptor region of human immunodeficiency virus type 1 (HIV-1) were prepared and evaluated for anti-HIV-1 activity. The structures of modified 15mers were confirmed by negative ion LSI mass spectroscopy, and the anti-HIV-1 activities were evaluated in vitro by MTT assay using MT-4 cells. While the unmodified 15mer had no activity in our assay system, the 15mers bearing modifications with trityl-type substituents at the 5'-end showed potent anti-HIV-1 activities.