5'-O-benzhydrylthymidine

• 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-benzhydrylthymidine
• 英文别名: 1-[(2R,4S,5R)-5-(benzhydryloxymethyl)-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• 化学式: C₂₃H₂₄N₂O₅
• 分子量: 408.454
• InChiKey: RNVXELWKYXKWIZ-XUVXKRRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 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-benzhydrylthymidine 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70%的产率得到5'-O-benzhydrylthymidine 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：

  3',5'-di-O-benzhydrylthymidine 在 palladium dichloride 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 32.0h， 生成 5'-O-benzhydrylthymidine
  参考文献：
  名称：

  A Straightforward Diphenylmethyl Protection Method and Deprotection of Some Pyrimidine Nucleosides

  摘要：

  已有人报道苯甲基保护一类和二类醇的方法，通过与金属烷氧化物反应。我们的目标是寻找普遍适用且非常温和的条件，用于核苷的醇保护和去保护，采用二苯基甲基基团。我们在一些嘧啶核苷中实现了这一点，使用PdCl2作为过渡金属催化剂，并通过优化实现了70-90%的产率。然而，其他核苷的溶解性不足限制了其更广泛的应用。

  DOI：

  10.3390/molecules18078524

文献信息

• Modified oligodeoxyribonucleoditides
  申请人：Sankyo Company, Limited

  公开号：US05674856A1

  公开（公告）日：1997-10-07

  Compounds for the treatment or prophylaxis of a viral infection in a mammal, which may be human, are provided. The compounds are oligodeoxyribonucleic acid derivatives, and a novel route to such compounds is also provided together with intermediates of more general utility. The active compounds are of the general formula (1): ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are hydrogen atoms, alkyl groups, aryl groups as defined, and anthraquinonyl groups as defined; Z is carbon or silicon; or R.sub.2, R.sub.3 and Z together represent fluorenyl or xanthenyl; R.sub.4 is a hydrogen atom, an alkyl group as defined, an aryl group as defined; Y.sub.1, Y.sub.3 and Y.sub.4 are oxygen, sulfur or >NH; Y.sub.2 is oxygen, sulfur, >NH, alkylene or phenylene; X is alkylene group as defined; m and n are 0 to 10; and B is an oligodeoxyribonucleotide of chain length 3 to 9; or salts thereof.

  提供了用于治疗或预防哺乳动物（包括人类）病毒感染的化合物。这些化合物是寡聚脱氧核糖核酸衍生物，同时提供了一种新的制备这些化合物的方法以及更通用的中间体。活性化合物的一般式（1）如下：##STR1##其中R.sub.1、R.sub.2和R.sub.3是氢原子、烷基、芳基（如定义）和蒽醌基（如定义）；Z是碳或硅；或R.sub.2、R.sub.3和Z共同表示芴基或黄酮基；R.sub.4是氢原子、烷基（如定义）、芳基（如定义）；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是烷基（如定义）；m和n为0到10；B是链长为3到9的寡聚脱氧核糖核酸；或其盐。
• Composition and method for the treatment or prophylaxis of viral
  申请人：Sankyo Company, Limited

  公开号：US05807837A1

  公开（公告）日：1998-09-15

  A composition and method of treatment or prophylaxis of a viral infection in a mammal, such as a human, are provided. The compounds in the composition and which are administered in the method, are oligodeoxyribonucleic acid derivatives of the formula (1): ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are hydrogen atoms, alkyl groups, aryl groups, and anthraquinonyl groups; Z is carbon or silicon; or R.sub.2, R.sub.3 and Z together represent fluorenyl or xanthenyl; R.sub.4 is a hydrogen atom, an alkyl group or an aryl group; Y.sub.1, Y.sub.3 and Y.sub.4 are oxygen, sulfur or >NH; Y.sub.2 is oxygen, sulfur, >NH, alkylene or phenylene; X is an alkylene group; m and n are each 0 to 10; and B is an oligodeoxyribonucleotide of a chain length of 3 to 9, or salts thereof.

  提供了哺乳动物，如人类的病毒感染的组合物和治疗或预防方法。组合物中的化合物以及在方法中被管理的化合物是公式（1）的寡脱氧核糖核酸衍生物：##STR1##其中R.sub.1，R.sub.2和R.sub.3是氢原子，烷基，芳基和蒽醌基；Z是碳或硅；或R.sub.2，R.sub.3和Z一起代表芴基或黄酮基；R.sub.4是氢原子，烷基或芳基；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是烷基；m和n分别为0至10；B是链长为3至9的寡脱氧核糖核酸或其盐。
• 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。
• 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