1-(5'-deoxy-5'-bromo-β-D-threo-pentofuranosyl)thymine | 124685-29-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 2 '，5'-二脱氧核苷
• 英文名称: 1-(5'-deoxy-5'-bromo-β-D-threo-pentofuranosyl)thymine
• 英文别名: 1-[(2R,4R,5S)-5-(bromomethyl)-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
• CAS: 124685-29-6
• 化学式: C₁₀H₁₃BrN₂O₄
• 分子量: 305.128
• InChiKey: LNWMTVFMZSJAFG-BWZBUEFSSA-N

物化性质

• 密度：
  1.672±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(5'-deoxy-5'-bromo-β-D-threo-pentofuranosyl)thymine 在 吡啶 、 4-二甲氨基吡啶 、 叠氮化锂 、 三甲基溴硅烷 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 55.0h， 生成 3'-azido-3',5'-dideoxythymidine-5'-phosphonic acid
  参考文献：
  名称：

  Design, Synthesis, and Structure-Activity Relationship of Novel Dinucleotide Analogs as Agents against Herpes and Human Immunodeficiency Viruses

  摘要：

  A new acyclic nucleoside phosphonate (13) containing an adenine moiety was synthesized, which acted as an excellent inhibitor of calf mucosal adenosine deaminase. This inhibitory property allows it to exert great synergistic effect on certain antiviral agents (e.g., ara-A, 37). Phosphonate 13 was not phosphorylated by the bovine brain guanylate kinase nor by 5-phosphoribosyl 1-pyrophosphate synthetase. Syntheses of biologically active nucleotide phosphonate 40 and its phosphonoamidate derivative 42 were accomplished, which showed remarkable activity against herpes viruses and exhibited low host cell toxicity. 3'-Azido-nucleoside phosphonate 20 and 3'-fluoronucleoside phosphonate 32, as well as the corresponding dinucleotide analogs 47 and 48, and their respective phosphonoamidates 53-56 were also synthesized as new compounds, among which phosphonoamidates 53-56 showed potent activity against human immunodeficiency virus. Phosphonoamidates 55 and 56 bearing a methyl D-alaninate moiety exhibited less cellular toxicity than 53 and 54 bearing a methyl L-alaninate moiety. Nucleotide phosphonate 40 as well as dinucleotide phosphonates 47 and 48 were found susceptible to degradation by phosphodiesterases. Their respective phosphonoamidates 42 and 53-56, however, were completely resistant to snake venom and spleen enzymes.

  DOI：

  10.1021/jm00023a004
• 作为产物：
  描述：

  3',4'-anhydrothymidine 在 三氟化硼乙醚 、 lithium bromide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以70%的产率得到1-(5'-deoxy-5'-bromo-β-D-threo-pentofuranosyl)thymine
  参考文献：
  名称：

  Design, Synthesis, and Structure-Activity Relationship of Novel Dinucleotide Analogs as Agents against Herpes and Human Immunodeficiency Viruses

  摘要：

  A new acyclic nucleoside phosphonate (13) containing an adenine moiety was synthesized, which acted as an excellent inhibitor of calf mucosal adenosine deaminase. This inhibitory property allows it to exert great synergistic effect on certain antiviral agents (e.g., ara-A, 37). Phosphonate 13 was not phosphorylated by the bovine brain guanylate kinase nor by 5-phosphoribosyl 1-pyrophosphate synthetase. Syntheses of biologically active nucleotide phosphonate 40 and its phosphonoamidate derivative 42 were accomplished, which showed remarkable activity against herpes viruses and exhibited low host cell toxicity. 3'-Azido-nucleoside phosphonate 20 and 3'-fluoronucleoside phosphonate 32, as well as the corresponding dinucleotide analogs 47 and 48, and their respective phosphonoamidates 53-56 were also synthesized as new compounds, among which phosphonoamidates 53-56 showed potent activity against human immunodeficiency virus. Phosphonoamidates 55 and 56 bearing a methyl D-alaninate moiety exhibited less cellular toxicity than 53 and 54 bearing a methyl L-alaninate moiety. Nucleotide phosphonate 40 as well as dinucleotide phosphonates 47 and 48 were found susceptible to degradation by phosphodiesterases. Their respective phosphonoamidates 42 and 53-56, however, were completely resistant to snake venom and spleen enzymes.

  DOI：

  10.1021/jm00023a004

文献信息

• Hydrophobically Modified Antisense Oligonucleotides Comprising a Ketal Group
  申请人：INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM)

  公开号：US20160108398A1

  公开（公告）日：2016-04-21

  The present invention concerns an oligonucleotide modified by substitution at the 3′ or the 5′ end by a moiety comprising at least one ketal functional group, wherein the ketal carbon of said ketal functional group bears two saturated or unsaturated, linear or branched, hydrocarbon chains comprising from 1 to 22 carbon atoms, and the use therefore as a medicament, in particular for use for treating cancer.

  本发明涉及一种寡核苷酸，其在3′或5′端被含有至少一个缩醛官能团的基团取代，其中所述缩醛官能团的缩醛碳带有两个饱和或不饱和、线性或支链、碳原子数为1至22的烃链，并且用作药物，特别用于治疗癌症。
• Cleavage of a nucleosidic oxetane with carbanions: synthesis of a highly promising candidate for anti-HIV agents — a phosphonate isostere of AZT 5′-phosphate
  作者：Hiromichi Tanaka、Mariko Fukui、Kazuhiro Haraguchi、Mariko Masaki、Tadashi Miyasaka

  DOI：10.1016/s0040-4039(01)80452-4

  日期：1989.1
• TANAKA, HIROMICHI;FUKUI, MARIKO;HARAGUCHI, KAZUHIRO;MASAKI, MARIKO;MIYASA+, TETRAHEDRON LETT., 30,(1989) N9, C. 2567-2570
  作者：TANAKA, HIROMICHI、FUKUI, MARIKO、HARAGUCHI, KAZUHIRO、MASAKI, MARIKO、MIYASA+

  DOI：——

  日期：——
• US9701962B2
  申请人：——

  公开号：US9701962B2

  公开（公告）日：2017-07-11