Pyrrolo[2,3-d]pyrimidine nucleosides:: Synthesis and antitumor activity of 7-substituted 7-deaza-2′-deoxyadenosines

被引:7
|
作者
Seela, F
Zulauf, M
Chen, SF
机构
[1] Univ Osnabruck, Inst Chem, Organ & Bioorgan Chem Lab, D-49069 Osnabruck, Germany
[2] Piedmont Res Ctr, Morrisville, NC 27560 USA
来源
关键词
D O I
10.1080/15257770008033006
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
A one step synthesis, using the nucleoside 7-iodo-2'-deoxytubercidin (2b) in a Pd(0)/Cu(I)-catalyzed cross coupling reaction furnished a series of 7-alkynyl-2'-deoxytubercidin derivatives. The 7-iodo-, 7-chloro- or 7-bromo 2'-deoxytubercidins 2b-d as well as certain 7-alkynyl derivatives show significant activity against several tumor cell lines, with 7-iodo-2'-deoxytubercidin (2b) as the most effective compound.
引用
收藏
页码:237 / 251
页数:15
相关论文
共 50 条
  • [1] 7-SUBSTITUTED 7-DEAZA-2'-DEOXYGUANOSINES - REGIOSELECTIVE HALOGENATION OF PYRROLO[2,3-D]PYRIMIDINE NUCLEOSIDES
    RAMZAEVA, N
    SEELA, F
    HELVETICA CHIMICA ACTA, 1995, 78 (05) : 1083 - 1090
  • [2] Regioselectivity of the Mannich reaction on pyrrolo[2,3-d]pyrimidine nucleosides related to 7-deaza-2'-deoxyadenosine or 7-deaza-2'-deoxyguanosine
    Seela, F
    Chen, YM
    Zulauf, M
    SYNTHESIS-STUTTGART, 1997, (09): : 1067 - &
  • [3] 7-substituted 7-deaza-2′-deoxyadenosines and 8-aza-7-deaza-2′-deoxyadenosines:: Fluorescence of DNA-base analogues induced by the 7-alkynyl side chain
    Seela, F
    Zulauf, M
    Sauer, M
    Deimel, M
    HELVETICA CHIMICA ACTA, 2000, 83 (05) : 910 - 927
  • [4] 7-nitro-7-deaza-2′-deoxyadenosine and 8-methyl-7-deaza-2′-deoxyguanosine:: Pyrrolo[2,3-d]pyrimidine nucleosides with different sugar conformations
    Seela, F
    Rosemeyer, H
    Zulauf, M
    Chen, YM
    Kastner, G
    Reuter, H
    LIEBIGS ANNALEN-RECUEIL, 1997, (12): : 2525 - 2530
  • [5] Pyrrolo[2,3-d]pyrimidine (7-deazapurine) as a privileged scaffold in design of antitumor and antiviral nucleosides
    Perlikova, Pavla
    Hocek, Michal
    MEDICINAL RESEARCH REVIEWS, 2017, 37 (06) : 1429 - 1460
  • [6] SYNTHESIS OF PYRIDO-[2,3-D]PYRIMIDINE AND PYRROLO-[2,3-D]PYRIMIDINE NUCLEOSIDES
    ITOH, T
    MELIKOHANJANIAN, RG
    ISHIKAWA, I
    KAWAHARA, N
    MIZUNO, Y
    OGURA, H
    JOURNAL OF PHARMACEUTICAL SCIENCES, 1987, 76 (11) : S220 - S220
  • [7] Synthesis of 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine and 2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine
    Hao, Baoyu
    Chen, Xinzhi
    Zhang, Weihan
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2010, 30 (06) : 918 - 922
  • [8] Synthesis of Fluorinated Pyrrolo[2,3-b]pyridine and Pyrrolo[2,3-d]pyrimidine Nucleosides
    Iaroshenko, Viktor O.
    Wang, Yan
    Sevenard, Dmitri V.
    Volochnyuk, Dmitriy M.
    SYNTHESIS-STUTTGART, 2009, (11): : 1851 - 1857
  • [9] 7-Deazapurine DNA: Oligonucleotides containing 7-substituted 7-deaza-2'-deoxyguanosine and 8-aza-7-deaza-2'-deoxyguanosine
    Seela, F
    Ramzaeva, N
    Becher, G
    COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1996, 61 : S258 - S261
  • [10] Synthesis and Anti-HCV Activity of 4-Methoxy-7H-Pyrrolo[2,3-d] Pyrimidine Carbocyclic Nucleosides
    Thiyagarajan, Anandarajan
    Toyama, Masaaki
    Baba, Masanori
    Sharon, Ashoke
    Bal, Chandralata
    NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS, 2016, 35 (06): : 305 - 314