5-(5-hydroxypentynyl)-dUrd | 77876-01-8

• 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-(5-hydroxypentynyl)-dUrd
• 英文别名: 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-(5-hydroxypent-1-ynyl)pyrimidine-2,4-dione；1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(5-hydroxypent-1-ynyl)pyrimidine-2,4-dione
• CAS: 77876-01-8
• 化学式: C₁₄H₁₈N₂O₆
• 分子量: 310.307
• InChiKey: MTJSWISCRCFSQT-QJPTWQEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  119
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-iodo-3',5'-di-O-p-toluyl-2'-deoxyuridine 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 sodium methylate 作用下， 以 甲醇 、 三乙胺 为溶剂， 反应 4.0h， 生成 5-(5-hydroxypentynyl)-dUrd
  参考文献：
  名称：

  核酸相关化合物。31.末端炔烃与5-碘尿嘧啶核苷的平滑高效钯钯催化偶联

  摘要：

  在三乙胺中存在二氯双（三苯基膦）钯和碘化铜（I）的情况下，末端炔烃与受保护的5-碘尿嘧啶核苷的偶联以72-92％的收率得到相应的5-（炔-1-基）尿嘧啶核苷。

  DOI：

  10.1016/0040-4039(81)80115-3

文献信息

• Nucleic acid related compounds. 31. Smooth and efficient palladium-copper catalyzed coupling of terminal alkynes with 5-iodouracil nucleosides
  作者：Morris J. Robins、Philip J. Barr

  DOI：10.1016/0040-4039(81)80115-3

  日期：1981.1

  Coupling of terminal alkynes with protected 5-iodouracil nucleosides in the presence of dichlorobis(triphenylphosphine)palladium and copper(I) iodide in triethylamine gives the corresponding 5-(alkyn-1-yl)uracil nucleosides in 72–92% yields.

  在三乙胺中存在二氯双（三苯基膦）钯和碘化铜（I）的情况下，末端炔烃与受保护的5-碘尿嘧啶核苷的偶联以72-92％的收率得到相应的5-（炔-1-基）尿嘧啶核苷。
• [EN] ANTI-VIRAL PYRIMIDINE NUCLEOSIDE ANALOGUES<br/>[FR] ANALOGUES DE NUCLEOSIDES DE PYRIMIDINE ANTIVIRAUX
  申请人：UNIV CARDIFF

  公开号：WO1998049177A1

  公开（公告）日：1998-11-05

  A compound having formula (I), wherein R is selected from the group comprising C5 to C20 alkyl, C5 to C20 cycloalkyl, halogens, aryl and alkylaryl; R' is selected from the group comprising hydrogen, alkyl, cycloalkyl, halogens, amino, alkylamino, dialkylamino, nitro, cyano, alkyoxy, aryloxy, thiol, alkylthiol, arythiol, alkyl; R'' is selected from the group comprising hydrogen, alkyl, cycloalkyl, halogens, alkyloxy, aryloxy and aryl; Q is selected from the group comprising O, S and CY2, where Y may be the same or different and is selected from H, alkyl and halogens; X is selected from the group comprising O, NH, S, N- alkyl, (CH2)n where n is 1 to 10, and CY2 where Y may be the same or different and is selected from hydrogen, alkyl and halogens; Z is selected from the group comprising O, S, NH, and N alkyl; U'' is H and U' is selected from H and CH2T, or U' and U'' are joined so as to form a ring moiety including Q wherein U'-U'' together is respectively selected from the group comprising -CTH-CT'T''- and -CT=CT- and -CT'=CT'-, so as to provide ring moieties selected from the group comprising formula (II) and (III) wherein T is selected from the group comprising OH, H, halogens, O-alkyl, O-acyl, O-aryl, CN, NH2 and N3; T' is selected from the group comprising H and halogens and where more than one T' is present they may be the same or different; T'' is selected from the group comprising H and halogens, and W is selected from the group comprising H, a phosphate group and a pharmacologically acceptable salt, derivative or prodrug thereof shows potent anti-viral activity against, for example, varicella zoster virus and cytomegalovirus.

  化合物的化学式为（I），其中R选择自C5到C20烷基，C5到C20环烷基，卤素，芳基和烷基芳基的群体；R'选择自氢，烷基，环烷基，卤素，氨基，烷基氨基，双烷基氨基，硝基，氰基，烷氧基，芳氧基，硫醇，烷硫醇，芳硫醇，烷基；R''选择自氢，烷基，环烷基，卤素，烷氧基，芳氧基和芳基；Q选择自O，S和CY2的群体，其中Y可以相同或不同，选择自氢，烷基和卤素；X选择自O，NH，S，N-烷基，（CH2）n，其中n为1至10，和CY2，其中Y可以相同或不同，选择自氢，烷基和卤素；Z选择自O，S，NH和N烷基；U''为H，U'选择自H和CH2T，或U'和U''结合形成包括Q的环基，其中U'-U''分别选择自-CTH-CT'T''-和-CT=CT-和-CT'=CT'-，从而提供从化学式（II）和（III）中选择的环基，其中T选择自OH，H，卤素，O-烷基，O-酰基，O-芳基，CN，NH2和N3；T'选择自H和卤素，当存在多个T'时，它们可以相同或不同；T''选择自H和卤素，W选择自H，磷酸盐基团和药理学上可接受的盐，衍生物或前药，表现出强大的抗病毒活性，例如对带状疱疹病毒和巨细胞病毒。
• ANTI-VIRAL PYRIMIDINE NUCLEOSIDE ANALOGUES
  申请人：University College Cardiff Consultants Limited

  公开号：EP0980377A1

  公开（公告）日：2000-02-23
• US6573247B1
  申请人：——

  公开号：US6573247B1

  公开（公告）日：2003-06-03
• Nucleic acid related compounds. 39. Efficient conversion of 5-iodo to 5-alkynyl and derived 5-substituted uracil bases and nucleosides
  作者：Morris J. Robins、Philip J. Barr

  DOI：10.1021/jo00159a012

  日期：1983.6