New 5-modified 2′-deoxyuridine derivatives: synthesis and antituberculosis activity

被引：6
|
作者：
Shmalenyuk, E. R. [1 ]
Karpenko, I. L. [1 ]
Chernousova, L. N. [2 ]
Chizhov, A. O. [3 ]
Smirnova, T. G. [2 ]
Andreevskaya, S. N. [2 ]
Alexandrova, L. A. [1 ]
机构：
[1] Russian Acad Sci, VA Engelhardt Mol Biol Inst, Moscow 119991, Russia
[2] Russian Acad Med Sci, Cent TB Res Inst, Moscow 107564, Russia
[3] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Moscow 119991, Russia
来源：
RUSSIAN CHEMICAL BULLETIN | 2014年 / 63卷 / 05期
基金：
俄罗斯基础研究基金会;
关键词：
nucleosides; 2 '-deoxyuridine; synthesis; inhibitor; antimycobacterial activity; tuberculosis; Mycobacterium tuberculosis; TUBERCULOSIS; C5;
D O I：
10.1007/s11172-014-0572-0
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
New 2'-deoxyuridine derivatives containing long-chain hydrophilic substituents or hydrophilic groups at the 5 position of uracil were synthesized. 5-[4-(2-Carboxyethylcarbonylamino)-butyloxymethyl]-2'-deoxyuridine completely inhibits the growth of Mycobacterium tuberculosis at a concentration of 50 mu g mL(-1). However, oligo(ethylene glycol) derivatives do not exhibit activity even at high concentrations.
引用
收藏
页码：1197 / 1200
页数：4
相关论文
共 50 条
  • [31] SYNTHESIS AND ANTIVIRAL ACTIVITY OF THE CARBOCYCLIC ANALOGS OF 5-ETHYL-2'-DEOXYURIDINE AND OF 5-ETHYNYL-2'-DEOXYURIDINE
    SHEALY, YF
    ODELL, CA
    ARNETT, G
    SHANNON, WM
    JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (01) : 79 - 84
  • [32] Synthesis and antituberculosis activity of some new 2-quinoxalinecarbonitriles
    Montoya, ME
    Sainz, Y
    Ortega, MA
    De Cerain, AL
    Monge, A
    FARMACO, 1998, 53 (8-9): : 570 - 573
  • [33] Synthesis of water-soluble prodrugs of 5-modified 2MODIFIER LETTER PRIME-deoxyuridines and their antibacterial activity
    Negrya, Sergey D.
    Jasko, Maxim, V
    Solyev, Pavel N.
    Karpenko, Inna L.
    Efremenkova, Olga, V
    Vasilyeva, Byazilya F.
    Sumarukova, Irina G.
    Kochetkov, Sergey N.
    Alexandrova, Liudmila A.
    JOURNAL OF ANTIBIOTICS, 2020, 73 (04): : 236 - 246
  • [34] Synthesis of some chalcones derivatives series and their antituberculosis activity
    Noviany, Noviany
    Osman, Hasnah
    Mohamad, Suriyati
    Hadi, Sutopo
    Satria, Heri
    Buhani, Buhani
    PURE AND APPLIED CHEMISTRY, 2024, 96 (03) : 351 - 368
  • [35] Antituberculosis: Synthesis and Antimycobacterial Activity of Novel Benzimidazole Derivatives
    Yoon, Yeong Keng
    Ali, Mohamed Ashraf
    Choon, Tan Soo
    Ismail, Rusli
    Wei, Ang Chee
    Kumar, Raju Suresh
    Osman, Hasnah
    Beevi, Farzana
    BIOMED RESEARCH INTERNATIONAL, 2013, 2013
  • [36] Antituberculosis agents, I: Synthesis and antituberculosis activity of 2-aryl-1,3,4-thiadiazole derivatives
    Foroumadi, A
    Mirzaei, M
    Shafiee, A
    PHARMAZIE, 2001, 56 (08): : 610 - 612
  • [37] 5-MODIFIED DDUTP DERIVATIVES AS TERMINATING SUBSTRATES FOR REVERSE TRANSCRIPTASES - PHOSPHODIESTERASE HYDROLYSIS OF OLIGONUCLEOTIDES TERMINATED BY THESE DERIVATIVES
    DYACHENKO, LB
    CHENCHIK, AA
    LUKIN, MA
    ALEKSANDROVA, LA
    KRAEVSKII, AA
    BIBILASHVILI, RS
    MOLECULAR BIOLOGY, 1994, 28 (01) : 67 - 74
  • [38] Synthesis and biological activity of O-alkyl-3-N-aminoacyloxymethyl-5-fluoro-2'-deoxyuridine derivatives
    Harada, N
    Hongu, M
    Kawaguchi, T
    Ohohashi, M
    Oda, K
    Hashiyama, T
    Tsujihara, K
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1996, 44 (06) : 1196 - 1201
  • [39] Temperature controlled stereoselectivity in the synthesis of 5-halo-2′-deoxyuridine derivatives
    Lagerwall, Tom
    Heinonen, Petri
    Oivanen, Mikko
    TETRAHEDRON LETTERS, 2015, 56 (43) : 5950 - 5953
  • [40] 5-BROMOETHINYL-2'-DEOXYURIDINE - SYNTHESIS AND BIOLOGICAL-ACTIVITY
    EGER, K
    JALALIAN, M
    BIOLOGICAL CHEMISTRY HOPPE-SEYLER, 1990, 371 (09): : 781 - 781
12345