5'-(12-hydroxydodecylthio)-5'-deoxythymidine | 158324-46-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5'-(12-hydroxydodecylthio)-5'-deoxythymidine
• 英文别名: 5'-deoxy-5'-(12-hydroxydodecylthio)thymidine；1-[(2R,4S,5S)-4-hydroxy-5-(12-hydroxydodecylsulfanylmethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 158324-46-0
• 化学式: C₂₂H₃₈N₂O₅S
• 分子量: 442.62
• InChiKey: YJRQJSZZBYKUJR-XUVXKRRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5'-(12-hydroxydodecylthio)-5'-deoxythymidine 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 4.5h， 生成 5'-(12-trityloxydodecylthio)-5'-deoxythymidine 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：

  12-溴-1-十二烷醇 、 5'-thio-thymidine 在 sodium carbonate 作用下， 以 丙酮 为溶剂， 反应 5.0h， 生成 5'-(12-hydroxydodecylthio)-5'-deoxythymidine
  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

文献信息

• ANTISENSE NUCLEIC ACID DERIVATIVE
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0558749A1

  公开（公告）日：1993-09-08

  A compound represented by general formula (1), its salt, and antiviral and antitumor drugs containing the same, wherein k is 0 to 20; m is 0 or 1; n is 4 to 29; X represents OH, methyl, sulfhydryl, C₁ to C₄ alkoxy or C₁ to C₆ monoalkylamino; Y and Z represent each O or S; R¹, R² and R³ may be the same or different from each other and each represents H, C₁ to C₆ alkyl, or C₆ to C₁₀ aryl which may have the substitutent(s) of group α; and D and B represent each independently a residue of any of the compounds of group β; provided that m is 0 when k is 0, and a base sequence containing B is complementary to a tumor gene or a virus gene: group α: OH, C₁ to C₆ alkyl, C₁ to C₆ alkoxy, methylenedioxy, nitro, azido, halogen, C₆ to C₁₀ aryl, C₆ to C₁₀ aryloxy, and aralkyloxy composed of a C₆ to C₁₀ aryl moiety and a C₁ to C₂ alkyl moiety, group β: adenine guanine, cytosine and thymine.

  通式(1)代表的化合物、其盐以及含有该通式的抗病毒和抗肿瘤药物，其中 k 为 0 至 20；m 为 0 或 1；n 为 4 至 29；X 代表 OH、甲基、巯基、C₁ 至 C₄ 烷氧基或 C₁ 至 C₆ 单烷基氨基；Y 和 Z 各自代表 O 或 S；R¹、R²和R³可以相同或不同，各自代表H、C₁至C₆烷基或C₆至C₁₀芳基，可具有α基团的取代基；D和B各自独立地代表β基团的任何化合物的残基；条件是当k为0时，m为0，且含有B的碱基序列与肿瘤基因或病毒基因互补：第 α 组OH, C₁ to C₆ alkyl, C₁ to C₆ alkoxy, methylenedioxy, nitro, azido, halogen, C₆ to C₁₀ aryl, C₆ to C₁₀ aryloxy, and aralkyloxy composed of a C₆ to C₁₀ aryl moiety and a C₁ to C₂ alkyl moiety, group β：腺嘌呤、鸟嘌呤、胞嘧啶和胸腺嘧啶。
• EP558749
  申请人：——

  公开号：——

  公开（公告）日：——