Synthesis, characterization and reactions of 2-deoxo-5-deazaalloxazines.
5-Deazaflavins and their homologues have been known as potential riboflavin antagonists, bioreductives, and compounds with potent antitumor activity. 2-Amino-4-methylquinoline-3-carbonitrile (2) was prepared as unreported starting material for several interesting 2-deoxo-5-deazalloxazine derivatives. Cyclization of 2 using formamide afforded the 2,4-deoxo-5-deazaalloxazine derivative 7, which was subjected to deamination with nitrous acid to give the 2-deoxo-5-deazaalloxazine (8). The compound 8 was also obtained via 13 by treating the latter with refluxing formic acid or formamide and used as a precursor for synthesis of several 2-deoxo-5-deazaalloxazines 18, 19, 20, 21 and 22. The pharmacological and biological properties of these compounds are still under investigation.
Sarhan
A E
AE
Chemistry Department, Faculty of Science, Assiut University, 71516, Assiut, Egypt. elwareth@acc.aun.eun.eg
Hozien
Z A
ZA
El-Sherief
H A
HA
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry; D005415:Flavins / Q000138:chemical synthesis* / Q000737:chemistry; D011621:Pteridines / Q000138:chemical synthesis* / Q000737:chemistry; D011744:Pyrimidinones / Q000138:chemical synthesis* / Q000737:chemistry; D012256:Riboflavin / Q000037:antagonists & inhibitors; D013057:Spectrum Analysis
D000970:Antineoplastic Agents; D000998:Antiviral Agents; D005415:Flavins; D011621:Pteridines; D011744:Pyrimidinones; C008173:isoalloxazine; D012256:Riboflavin