Improved synthesis, antibacterial activity and potential carcinogenicity of 5-amino-1,2,4-thiadiazol-3(2H)-one

Pharmazie

Volumn 59, Issue 10, 2004, Pages 756-762

  Piskala A ^a   Vachalkova A ^b   Masojidkova M ^a   Horvathova K ^b   Ovesna Z ^b   Paces V ^c   Novotný, Ladislav ^d  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^b INSTITUTE OF CHEMISTRY   (Slovakia)

^c INSTITUTE OF MOLECULAR GENETICS   (Czech Republic)

^d KUWAIT UNIVERSITY   (Kuwait)

Author keywords

[No Author keywords available]

Indexed keywords

1 CYANOUREA DERIVATIVE; 5 AMINO 1,2,4 THIADIAZOL 3(2H) ONE; CYSTEINE; CYTOSINE DERIVATIVE; HYDROGEN SULFIDE; METHYL GROUP; PYRIMIDINE DERIVATIVE; SILVER DERIVATIVE; SULFUR DERIVATIVE; THIADIAZINE DERIVATIVE; THIOBIURET; UNCLASSIFIED DRUG; UREA DERIVATIVE;

ALKALINITY; ANTIBACTERIAL ACTIVITY; ARTICLE; CONCENTRATION RESPONSE; DEGRADATION KINETICS; DRUG ACTIVITY; DRUG CARCINOGENICITY; DRUG SYNTHESIS; GROWTH INHIBITION; HUMAN; HUMAN CELL; OXIDATION; POLAROGRAPHY; STRUCTURE ANALYSIS;

ANTI-BACTERIAL AGENTS; BENZOPYRANS; CARCINOGENS; CELL LINE, TUMOR; CHROMATOGRAPHY, THIN LAYER; ENBUCRILATE; FURANS; HUMANS; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; POLAROGRAPHY; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; SPECTROPHOTOMETRY, ULTRAVIOLET; SULFITES;

EID: 6344225543     PISSN: 00317144     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (43)

1. Antonello S, Benassi R, Gavioli G, Taddei F, Maran F (2002) Theoretical and electrochemical analysis of dissociative electron transfers proceeding through formation of loose radical anion species: reduction of symmetrical and unsymmetrical disulfides. J Am Chem Soc 124: 7529-7538.
2. Beisler JA, Abassi MM, Driscoll JS (1979) Synthesis and antitumor activity of 5-azacytosine arabinoside. J Med Chem 22: 1230-1234.
3. Bieling H, Earth P, Beyer H (1964) Über den Cyanharnstoff. Z Chem 4: 146-147.
4. Benjamin FJ (1980) The chemistry of the degradation of 5-azacytidine and some derivatives of 5-azacytosine. Ph.D. Thesis. University of Kansas, 1979
5. Carr BI, Reilly JG, Smith SS, Winberg C, Riggs A (1984) The tumorigenicity of 5-azacytidine in the male Fischer rat. Carcinogenesis (Lond) 5: 1583-1590.
6. Carr BI, Rahbar S, Asmeron Y, Riggs A, Winberg CD (1988) Carcinogenicity and haemoglobin synthesis induction by cytidine analogues. Br J Cancer 57: 395-402.
7. Chwang TL, Němec J, Welch AD (1980) Synthesis and characterization of 5-amino-2-(β-D-ribofuranosyl)-1,2,4-thiadiazoline-3-one, a sulfur-containing analog of cytidine. J Carbohydr Nucleosides Nucleotides 7: 159-166.
8. Čihák A, Šorm F (1965) Biochemical effects and metabolic transformations of 5-azacytidine in Escherichia coli. Collect Czech Chem Commun 30: 2091-2102.
9. Glover AB, Leyland-Jones BR, Chun HG, Davies B, Hoth DF (1987) Azacitidine: 10 years later. Cancer Treat Rep 71: 737-746.
10. Grem JL, Shoemaker DD, Hoth DF, King SA, Plowman J, Zaharko D, Grieshaber CK, Harrison Jr SD, Cradock JC, Leyland-Jones B (1987) Arabinosyl-5- azacytosine: a novel nucleoside entering clinical trials. Invest New Drugs 5: 315-328.
11. Hecht O (1892) Über Thiobiurete. Ber Dtsch Chem Ges 25: 749-758.
12. Hocek M, Holy̌ A, Votruba I, Dvořáková H (2000) Synthesis and cytostatic activity of substituted 6-phenylpurine bases and nucleosides: application of the Suzuki-Miyaura cross-coupling reactions of 6-chloropurine derivatives with phenylboronic acids. J Med Chem 43: 1817-1825.
13. Kantarjian HM, O'Brien SM, Keating M, Beran M, Estey E, Giralt S, Kornblau S, Rios MB, deVos D, Talpaz M (1997) Results of decitabine therapy in the accelerated and blastic phases of chronic myelogenous leukemia. Leukemia 11: 1617-1620.
14. Koechlin BA, Rubio F, Palmer S, Gabriel T, Duschinsky R (1966) The metabolism of 5-fluorocytosine-2-14-C and of cytosine-14-C in the rat and the disposition of 5-fluorocytosine-2-14-C in man. Biochem Pharmacol 15: 435-446.
15. Kurzer F (1965) 1,2,4-Thiadiazoles. Adv Heterocycl Chem 5: 119-204.
16. Kurzer F, Taylor SA (1958) Thiadiazoles. Part VI. 5-Amino-3-hydroxy-1,2, 4-thiadiazole derivatives. J Chem Soc 379-386.
17. Mertes MP, Pískala A, Škutchan J, Veselý J (1984) Synthesis and antileukemic activity of 1-β-D-arabinofuranosyl-5-azacytosine and its α-Danomer. Nucleic Acids Res, Symp Ser No 14: 237-238.
18. Novotný L, Vachálková A, Pískala A (1994) Polarographic reduction and potential cancerogenity of synthetic 1,3,5-triazine bases and nucleosides. Collect Czech Chem Commun 59: 1691-1698.
19. Novotný L, Vachálková A, Pískala A (1995) Polarographic reduction and potential carcinogenity of substituted 1,3,5-triazine nucleosides. Collect Czech Chem Commun 60: 1469-1475.
20. Novotný L, Vachálková A, Pískala A, Petrášová R, Blešová B (1996a) Potential carcinogenicity of the synthetic 1,3,6-triazine (6-aza) nucleic acid analogues determined by DC polarography. I. Nucleobases. Neoplasma 43: 403-406.
21. Novotný L, Vachálková A, Pískala A (1996b) Investigation of the polarographic properties and potential carcinogenity of some hydroxyurea derivatives by DC polarography. Collect Czech Chem Commun 61: 656-662.
22. Novotný L, Vachálková A, Pískala A (1999a) Potential carcinogenicity of the synthetic 1,3,6-friazine (6-aza-pyrimidine) nucleic acid analogues determined by DC polarography. II. Nucleosides of 6-azauracil. Neoplasma 46: 156-160.
23. Novotný L, Vachálková A, Pískala A (1999b) Polarographic properties and potential carcinogenicity of some natural nucleosides and their synthetic analogues. Bioelectrochem Bioenerg 48: 129-134.
24. Osmak M, Bordukalo T, Ristov AA, Jernej B, Kosmrlj J, Polanc S (2000) Diazenes as modificators of drug-resistance in tumor cells. Neoplasma 47: 390-395.
25. Párkányi C, Yuan HL, Cho NS, Jaw J-H J, Woodhouse TE, Aung TL (1989) 2-(2′,3′-dihydroxypropyl)-5-amino-2H-1,2,4-thiadiazol-3- one and 3-(2′,3′-dihydroxypropyl)-5-amino-3H-1,3,4-thiadiazol-2-one. J Heterocycl Chem 26: 1331-1334.
26. Perrin DD (1963) Buffers of low ionic strength for spectrophotometric pK determinations. Aust J Chem 16: 572-578.
27. Pískala A, Šorm F (1964) Nucleic acids components and their analogues. LI. Synthesis of 1-glycosyl derivatives of 5-azauracil and 5-azacytosine. Collect Czech Chem Commun 29: 2060-2076.
28. Pískala A, Šorm F (1978) 4-Amino-1-β-D-ribofuranosyl- s-triazin-2(1H)-one (5-azacytidine). Direct synthesis of a 5-azapyrimidine ribonucleoside by the trimethylsilyl procedure. In: Townsend LB, Tipson RS (eds) Nucleic Acid Chemistry, Part 1, Wiley, New York, p. 435-441.
29. Pískala A, Šorm F (1978) Anomeric 4-amino-1-(2-deoxy-D- erythro-pentofuranosyl)-S-triazin-2(1H)-ones (2′-deoxy-5-azacytidine and its α-D anomer). Synthesis of 5-azapyrimidine deoxyribonucleosides via acylglycosyl isocyanates. In: Townsend LB, Tipson RS (eds) Nucleic Acid Chemistry, Part 1, Wiley, New York, p. 443-449.
30. Pískala A, Hanna NB, Masojídková M, Otmar M, Fiedler P, Ubik K (2003) Synthesis of N4-alkyl-5-azacytidines and their base-pairing with carbamoylguanidines-a contribution to explanation of the mutagenicity of 2′-deoxy-5-azacytidine. Collect Czech Chem Commun 68: 711-743.
31. Pliml J, Šorm F (1964) Synthesis of 2-deoxy-D-ribofuranosyl-5- azacytosine. Collect Czech Chem Commun 29: 2576-2577.
32. Revankar GR, Robins RK (1976) Synthesis of certain 1,2,4-thiadiazole nucleosides J Heterocycl Chem 13: 169-170.
33. Revankar GR, Robins RK (ICN Pharmaceuticals, Inc.) (1978) 1,2,4-Thiadiazolidine-3,5-dione. US 4 093 624 (CI 260-302D; C07D285/08), 06 Jun 1978, Appl 763,913, 31 Jan 1977. C.A. 89: 180309.
34. Riddick JA, Bunger WB (1970) In: Organic Solvents, Vol II, Weissberger A (ed), N,N-dimethylformamide. Wiley Interscience, New York, p. 836-840.
35. Rivard GE, Momparler RL, Demers J, Benoit P, Raymond R, Lin K, Momparler LF (1981) Phase I study on 5-aza-2′-deoxycytidine in children with acute leukemia. Leukemia Res 5: 453-462.
36. Škoda J, Čihák A, Gut J, Prystaš M, Pískala A, Párkányi C, Šorm F (1962) Nucleic acid components and their analogues. XXIII. Inhibition of growth of Escherichia coli by derivatives of pyrimidine, 5-azauracil, 6-azauracil and some simpler models of these derivatives Collect Czech Chem Commun 27: 1736-1743.
37. Slotta KH, Tschesche R (1929) Über Isocyanate, VI: Kondensationen von Methylisocyanat mit Cyanamid unter dem Einfluß von Triäthyl-phosphin. Ber Dtsch Chem Ges 62: 137 145.
38. Šorm F, Pískala A, Čihák A, Veselý J (1964) 5-Azacytidine, a new, highly effective cancerostatic. Experientia 20: 202-203.
39. Šorm F, Pískala A (Československá akademie věd/Czechoslovac Academy of Sciences) (1966) 5-Aza-1-glycosylcytosines. Neth Appl 6 414 959 (C1 C 07 d), 23 June 23 1965, Czech Appl 22 Dec 1963; C.A. 64: 2154.
40. Stiborová M (2002) Aromatické nitrosloučeniny: kontaminanty životnflio prostředí a potenciá lní karcinogeny pro člověka (in Czech). Chem Listy 96: 784-791.
41. Vachálková A, Novotný L, Pískala A (1993) Polarographic reduction and cancerogenic index tg α of 5-aza nucleosides. Neoplasma 40: 289-292.
42. Wilhelm M, O'Brien S, Rios MB, Estey E, Keating MJ, Plunkett W, Sorenson M, Kantarjian HM (1999) Phase I study of arabinosyl-5-azacytidine (fazarabine) in adult acute leukemia and chronic myelogenous leukemia in blastic phase. Leuk Lymphoma 34: 511-518.
43. Wunderlich A (1886) Über Carbamincyamide. Ber Dtsch Chem Ges 19: 448-456.