Biopolym. Cell. 1998; 14(4):371-380.
Реакції йодування вуглеводного фрагмента піримідинових нуклеозидів як перспективний метод одержання протиретровірусних препаратів
1Шаламай А. С.
  1. Інститут молекулярної біології і генетики НАН України
    Вул. Академіка Заболотного, 150, Київ, Україна, 03680

Abstract

Здійснено аналіз сучасних методів хімічного деоксигенування нуклеозидів, які пов'язані з реакціями нуклеофільного заміщення гідроксильних груп та β -елімінування проміжних активних синтоиів. Показано перспективність йодування вуглеводного залишку піримідинових нуклеозидів за допомогою йодфосфонісвих солей. Вивчено механізм деоксигенування. 5'-О-захищених похідних уридипу та тимінрибозиду, куди входять окремі реакції утворення С2~ та С3-квазіфосфонієвих йодидів, їхнє подальше внутрішньомолекулярне перетворення та β-елімінування 2',3'-дийодпохідних.

References

[1] De Clercq E. Antiviral Activity Spectrum of Nucleoside and Nucleotide Analogues. Nucleosides and Nucleotides. 1991;10(1-3):167–80.
[2] Wright GE, Brown NC. Deoxyribonucleotide analogs as inhibitors and substrates of DNA polymerases. Pharmacol Ther. 1990;47(3):447-97.
[3] Dyatkina N, Minassian S, Kukhanova M, Krayevsky A, von Janta-Lipinsky M, Chidgeavadze Z, Beabealashvilli R. Properties of 2',3'-dideoxy-2',3'-dehydrothymidine 5'-triphosphate in terminating DNA synthesis catalyzed by several different DNA polymerases. FEBS Lett. 1987;219(1):151-5.
[4] Chidzhavadze ZG, Bibilashvili RSh, Rozovskaia TA, Atrazhev AM, Tarusova NB, Minasian ShKh, Diatkina NB, Atrazheva ED, Kukhanova MK, Papchikhin AV, et al. [Conformation limited nucleoside-5'-phosphates as termination substrates for DNA-polymerases]. Mol Biol (Mosk). 1989;23(6):1732-42.
[5] Stavudine (Zerit). Drugs Fut. 1995; 20(20):1088-9.
[6] Stavudine (Zerit). Drugs Fut. 1996; 21(10):1084-6.
[7] Riddler SA, Anderson RE, Mellors JW. Antiretroviral activity of stavudine (2',3'-didehydro-3'-deoxythymidine, D4T). Antiviral Res. 1995;27(3):189-203.
[8] Pavia AT, Gathe J. Clinical efficacy of stavudine (D4T zerit) compared to zidovudine (ZDV, Retrovir) in ZDV-pretreated HIV positive patients. 35th Intersci. Conf. Antirnicrob. Agents Chemother. (Sept. 17-20, San Francisco): Abstrs. San Francisco, 1995: 1169.
[9] Herdewijn P, Balzarini J, De Clercq E, Pauwels R, Baba M, Broder S, Vanderhaeghe H. 3'-substituted 2',3'-dideoxynucleoside analogues as potential anti-HIV (HTLV-III/LAV) agents. J Med Chem. 1987;30(8):1270-8.
[10] Baba M, Pauwels R, Herdewijn P, De Clercq E, Desmyter J, Vandeputte M. Both 2',3'-dideoxythymidine and its 2',3'-unsaturated derivative (2',3'-dideoxythymidinene) are potent and selective inhibitors of human immunodeficiency virus replication in vitro. Biochem Biophys Res Commun. 1987;142(1):128-34.
[11] Chu CK, Schinazi RF, Arnold BH, Cannon DL, Doboszewski B, Bhadti VB, et al. Comparative activity of 2?,3?-saturated and unsaturated pyrimidine and purine nucleosides against human immunodeficiency virus type 1 in peripheral blood mononuclear cells. Biochem Pharmacol. 1988;37(19):3543–8.
[12] Joshi BV, Reese CB. Synthesis of base sensitive 2', 3'-didehydro-2',3'-dideoxynucleotidcs. Abstrs of MRC AIDS Directed Progr Workshop. Warwick: Univ. publ., 1991.
[13] Koshida R, Cox S, Harmenberg J, Gilljam G, Wahren B. Structure-activity relationships of fluorinated nucleoside analogs and their synergistic effect in combination with phosphonoformate against human immunodeficiency virus type 1. Antimicrob Agents Chemother. 1989;33(12):2083–8.
[14] Nakayama T, Asai T, Okazoe T, Suga A, Morizawa Y, Yasuda A. Nucleoside analogs with vinyl fluoride structure; synthesis and anti-HIV activity. Nucleic Acids Symp Ser. 1991;(25):191-2.
[15] Krayevsky AA, Watanabe KA. Modified nucleosides as anti-AIDS drugs: Current status and perspectives. Bioinform. Moscow, 1993: 219.
[16] Horwitz JP, Chua J, Klundt IL, DaRooge MA, Noel M. Nucleosides. VI. The Introduction of Unsaturation into the Carbohydrate of a Pyrimidine Nucleoside via a 2,3?-Anhydro Bond . J Am Chem Soc. 1964;86(9):1896–7.
[17] Horwitz JR, Chua J, Da Rooge MA, Noel M, Klundt IL. Nucleosides. IX. The formation of 2',2'-unsaturated pyrimidine nucleosides via a novel beta-elimination reaction. J Org Chem. 1966;31(1):205-11.
[18] Horwitz JP, Chua J, Noel M, Donatti JT. Nucleosides. XI. 2',3'-dideoxycytidine. J Org Chem. 1967;32(3):817-8.
[19] Lin T-S, Yang J-H, Gao Y-S. Synthesis of 2?,3?-unsaturated and 2?, 3?-dideoxy analogs of 6-azapyrimidine nucleosides as potential anti-hiv agents. Nucleosides Nucleotides. 1990;9(1):97–108.
[20] Mansuri MM, Starrett JE Jr, Ghazzouli I, Hitchcock MJ, Sterzycki RZ, Brankovan V, Lin TS, August EM, Prusoff WH, Sommadossi JP, et al. 1-(2,3-Dideoxy-beta-D-glycero-pent-2-enofuranosyl)thymine. A highly potent and selective anti-HIV agent. J Med Chem. 1989;32(2):461-6.
[21] Vial J-M, Agback P, Chattopadhyaya J. A new Synthesis of 1-(2,3-Dideoxy-?-D-Glycero-Pent-2-Enofuranosyl)- Thymine. A Highly Potent and Selective Anti-Hiv Agent. Nucleosides Nucleotides. 1990;9(2):245–58.
[22] Dudycz LW. Synthesis of 2?,3?-Dideoxyuridine Via the Corey-Winter Reaction. Nucleosides Nucleotides. 1989;8(1):35–41.
[23] Chu CK, Ullas GV, Jeong LS, Ahn SK, Doboszewski B, Lin ZX, Beach JW, Schinazi RF. Synthesis and structure-activity relationships of 6-substituted 2',3'-dideoxypurine nucleosides as potential anti-human immunodeficiency virus agents. J Med Chem. 1990;33(6):1553-61.
[24] Robins MJ, Hansske F, Low NH, Park JI. A mild conversion of vicinal diols to alkenes. Efficient transformation of ribonucleosides into 2?-ene and 2t',3?-dideoxynucleosides. Tetrahedron Lett. 1984; 25(4):367-70.
[25] Chu CK, Bhadti VS, Doboszewski B, Gu ZP, Kosugi Y, Pullaiah KC, Van Roey P. General syntheses of 2',3'-dideoxynucleosides and 2',3'-didehydro-2',3'-dideoxynucleosides . J Org Chem. 1989; 54(9):2217-25.
[26] McDonald FE, Gleason MM. Asymmetric syntheses of stavudine(d4T) and cordycepin by cycloisomerization of alkynyl alcohols to endocyclic enol ethers. Angew Chem Int Ed Engl. 1995;34(3):350–2.
[27] Lipshutz BH, Stevens KL, Lowe RF. A novel route to the anti-HIV nucleoside d4T. Tetrahedron Lett. 1995;36(16):2711–2.
[28] Verheyden JP, Moffatt JG. Halo sugar nucleosides. II. Iodination of secondary hydroxyl groups of nucleosides with methyltriphenoxyphosphonium iodide. J Org Chem. 1970;35(9):2868-77.
[29] Verheyden JP, Moffatt JG. Halo sugar nucleosides. 3. Reactions for the chlorination and bromination of nucleoside hydroxyl groups. J Org Chem. 1972;37(14):2289-99.
[30] Codington JF, Doerr IL, Fox JJ. Synthesis of 2'-fluorothymidinc, 2'-fluorodcoxyuridine and other 2'-halogeno-2'-deoxynucleosides. J Org Chem. 1964. 29(3): 558-64.
[31] Codington JF, Doerr IL, Fox JJ. Nucleosides. XIX. Structure of the 2'-halogeno-2'-deoxypyrimidine nucleosides 1. J Org Chem. 1964; 29(3):564-9.
[32] Garegg PJ, Samuelsson B. Conversion of vicinal diols into olefins using triphenylphosphine and triiodoimidazole. Synthesis. 1979;1979(10):813–4.
[33] Garegg PJ, Samuelsson B. Novel reagent system for converting a hydroxy-group into an iodo-group in carbohydrates with inversion of configuration. J Chem Soc, Chem Commun . 1979;(22):978.
[34] Garegg PJ, Samuelsson B. Novel reagent system for converting a hydroxy-group into an iodo-group in carbohydrates with inversion of configuration. Part 2.J Chem Soc Perkin 1. 1980;2866-8.
[35] Bessodes M, Abushanab E, Panzica RP. A new and versatile method for the preparation of unsaturated sugars. J Chem Soc, Chem Commun. 1981;(1):26.
[36] Kostina VG, Shalamay AS, Usenko LS, Gladkaya VA. Recyclizalion of O2,2'-cyclopyrimidinnucleosicies with the use of haloid derivatives of threevalent phosphor and quasiphosphonic sails. Biopolym Cell. 1997; 13(3):197-201.
[37] Fox JJ, Miller N, Wempen I. Nucleosides. XXIX. 1-?-D-Arabinofuranosyl-5-fluorocytosine and Related Arabino Nucleosides 1 . J Med Chem. 1966;9(1):101–5.