Novel 5′-Norcarbocyclic Derivatives of Bicyclic Pyrrolo- and Furano[2,3-d]Pyrimidine Nucleosides

被引:7
|
作者
Klimenko, Anna A. [1 ]
Matyugina, Elena S. [1 ]
Logashenko, Evgeniya B. [2 ]
Solyev, Pavel N. [1 ]
Zenkova, Marina A. [2 ]
Kochetkov, Sergey N. [1 ]
Khandazhinskaya, Anastasia L. [1 ]
机构
[1] Russian Acad Sci, Engelhardt Inst Mol Biol, 32 Vavilov St, Moscow 119991, Russia
[2] Russian Acad Sci, Inst Chem Biol & Fundamental Med, Siberian Branch, 8 Lavrentiev Ave, Novosibirsk 630090, Russia
来源
MOLECULES | 2018年 / 23卷 / 10期
基金
俄罗斯基础研究基金会;
关键词
5 '-norcarbocyclic nucleoside analogues; antiproliferative properties; structure-activity relationship; BIOLOGICAL EVALUATION; ANALOGS; INHIBITORS; POTENT; VZV;
D O I
10.3390/molecules23102654
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
Here we report the synthesis and biological activity of new 5'-norcarbocyclic derivatives of bicyclic pyrrolo-and furano[2,3-d]pyrimidines with different substituents in the heterocyclic ring. Lead compound 3i, containing 6-pentylphenyl substituent, displays inhibitory activity with respect to a number of tumor cells with a moderate selectivity index value. Compound 3i induces cell death by the apoptosis pathway with the dissipation of mitochondrial potential.
引用
收藏
页数:12
相关论文
共 50 条
  • [21] SYNTHESIS OF THE NOVEL PYRROLO[2,3-D]PYRIMIDINE ALKALOID RIGIDIN
    EDSTROM, ED
    WEI, Y
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1993, 205 : 245 - ORGN
  • [22] A NOVEL SYNTHETIC APPROACH TO PYRROLO[2,3-D]PYRIMIDINE ANTIFOLATES
    MIWA, T
    HITAKA, T
    AKIMOTO, H
    JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (07): : 1696 - 1701
  • [23] SYNTHESIS OF A NOVEL PYRROLO[2,3-D]PYRIMIDINE ALKALOID, RIGIDIN
    EDSTROM, ED
    WEI, Y
    JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (02): : 403 - 407
  • [24] A NOVEL SYNTHETIC APPROACH TO PYRROLO[2,3-D]PYRIMIDINE ANTIFOLATES
    MIWA, T
    HITAKA, T
    AKIMOTO, H
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1991, 202 : 113 - ORGN
  • [25] Novel pyrrolo[2,3-d]pyrimidine ring forming methodology
    Watson, SE
    Khandkar, F
    Bui, M
    Markovich, A
    Taylor, EC
    SYNTHETIC COMMUNICATIONS, 1998, 28 (20) : 3885 - 3894
  • [26] SYNTHESIS AND CHEMICAL REACTIVITY OF NUCLEOSIDES RELATED TO PYRROLO[2,3-D]PYRIMIDINE NUCLEOSIDE ANTIBIOTICS
    TOWNSEND, LB
    MILNE, GH
    TRANSACTIONS OF THE NEW YORK ACADEMY OF SCIENCES, 1974, 36 (07): : 705 - 705
  • [27] Toward Pyrrolo[2,3-d]pyrimidine Scaffolds
    El Kaim, Laurent
    Grimaud, Laurence
    Wagschal, Simon
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (15): : 5343 - 5346
  • [28] Pyrrolo[2,3-d]pyrimidine derivatives in the synthesis of a novel heterocyclic system 2a,5a,7-triazaacenaphthylene
    Lyubov V. Muzychka
    Iryna O. Yaremchuk
    Evgenii V. Verves
    Oleg B. Smolii
    Chemistry of Heterocyclic Compounds, 2019, 55 : 397 - 400
  • [29] Pyrrolo[2,3-d]pyrimidine derivatives in the synthesis of a novel heterocyclic system 2a,5a,7-triazaacenaphthylene
    Muzychka, Lyubov V.
    Yaremchuk, Iryna O.
    Verves, Evgenii V.
    Smolii, Oleg B.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2019, 55 (4-5) : 397 - 400
  • [30] NOVEL PYRROLO[2,3-D]PYRIMIDINE ANTIFOLATES - SYNTHESIS AND ANTITUMOR ACTIVITIES
    MIWA, T
    HITAKA, T
    AKIMOTO, H
    NOMURA, H
    JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (02) : 555 - 560