Pyrimidinthiones (part I): Utility of 2-thioxopyrimidin-6-(1H)ones as ring transformer in the synthesis of fused bi- and tri-cyclic heterocyclic compounds and their potential biological activities
Salem, M. A.I.; H. M. F. Madkour; Marzouk, M. I.; Azab, M. E.; Mahmoud, N. F.H.;
Abstract
The pyrimidinethiones have wide biological and pharmaceutical activities, that have attracted considerable interest in recent years especially as antiviral inhibiting production of hepatitis B virus (HBV), and in vitro insulin-mimetic. Activity of the complexes of pyrimidinone derivatives evaluated from 50% inhibitory concentration promoted us to study the transformation of the 2-thioxopyrimidin-6(1H) ones to fused bi- and tri-cyclic heterocyclic compounds having the pyrimidine moieties and screening their biological activity. The reactivity of 2-mercapto-4-aryl-5-cyanopyrimidin-6(1H)ones (1) towards alkylation by different mono and bifunctional halo-organic compounds has been investigated to give S-monoalkylated products 2, 7 and 9; S- and N-dialkylated products 3, 13 and 14. Treatment of 1 and/or 2 with hydrazine hydrate as a nitrogen nucleophile have been investigated to give 4, treatment of 4 with CS2 and sodium nitrite in the presence of acetic acid (0C) produced 1,2,4-triazolopyrimidin-5(1H)one derivatives (5)and tetrazolo[1,5-a]pyrimidin- 5(1H)ones (6), respectively. Also cyclization of 7 and 9 gave [1,3]thiazolo[3,2-a]pyrimidin-5(1H)one and [1,3]thiazolo[3,2-a]pyrimidin-3,5- dione derivatives 8 and 10 respectively, treatment of 10 with aromatic aldehyde produces 11 which reacted with guanidine HCl to give pyrimido[4,5-d]thiazolo[3, 2-a]pyrimidin-6(1H)one derivative 12. Reaction of 14 with o-phenylenediamine was investigated and gave [1,4]quinoxalino[2,3-b][1,3]thiazolo[3,2-a]pyrimidin- 9(1H)one derivative 15.
Other data
Title | Pyrimidinthiones (part I): Utility of 2-thioxopyrimidin-6-(1H)ones as ring transformer in the synthesis of fused bi- and tri-cyclic heterocyclic compounds and their potential biological activities | Authors | Salem, M. A.I.; H. M. F. Madkour ; Marzouk, M. I.; Azab, M. E.; Mahmoud, N. F.H. | Keywords | Thiazolo[3,2-a]pyrimidinone;Pyrimido[4,5-d]thiazolo[3,2-a]pyrimidinone;Quinoxalino [2,3-b]thiazolo[3,2-a]pyrimidinone | Issue Date | 1-Oct-2008 | Publisher | TAYLOR & FRANCIS LTD | Journal | Phosphorus, Sulfur and Silicon and the Related Elements | Volume | 183 | Issue | 10 | Start page | 2596 | End page | 2614 | ISSN | 10426507 | DOI | 10.1080/10426500801967963 | Scopus ID | 2-s2.0-52949115705 | Web of science ID | WOS:000259646700022 |
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