Synthesis and Anti-Hepatitis B Virus Activity of Some 2,3-Dihydroxyprop-1-yl Unnatural Hetaryls

Abstract

The sodium salts of some hetaryls of the quinoxalin‐2‐ones 2—4, phthalazine‐1,4‐dione 5, phthalazin‐1‐one 6, and pyridazin‐6‐ones 7 and 8 were alkylated with (±) 2,3‐O‐isopropylidene‐1‐O‐(4‐toluenesulfonyl) glycerol (1) to give the respective tetraseco‐nucleosides 9—15. Their deisopropylidenation with 70% acetic acid in water gave the corresponding 2,3‐dihydroxyprop‐1‐yl hetaryls 16—22. Compounds 16—22 showed varying inhibition activity against Hepatitis B virus (HBV) with low to moderate cytotoxicity, where 18 and 21 showed the highest replication inhibition and low cytotoxicity.

Novel Regioselective Formation of S- and N-Hydroxyl-Alkyls of 5-(3-Chlorobenzo[b]Thien-2-yl)-3-Mercapto-4H-1,2,4-Triazole and A Facile Synthesis of Triazolo-Thiazoles and Thiazolo-Triazoles. Role of Catalyst and Microwave

“…[34][35][36] The combination of solvent-free reaction conditions and microwave irradiation leads to simplicity in operation, less pollution and higher selectivity with several eco-friendly advantages in the context of green chemistry. [37][38][39] Based on the above considerations and in continuation of our work on acyclonucleoside analogues, [40][41][42] we report herein the synthesis of new hydroxy-alkylation of the combined heterocycle 5-(3-chlorobenzo[b]thien-2-yl)-3-mercapto-4H -1,2,4-triazole and the intramolecular dehydrative ring closure of the S-hydroxyalkylated derivatives to triazolo-thiazoles and thiazolo-triazoles. The effect of solid support and MW in accelerating the synthesis have been investigated.…”