Synthesis of tetrazole ribonucleosides and their evaluation as antiviral agents

Abstract

Synthesis of 1-beta-D-ribofuranosyltetrazole and two 5-substituted derivatives, i.e., the 5-carboxamide and 5-acetamide, is described. The stereochemical structure of the parent tetrazole ribonucleoside has been established by means of nuclear Overhauser effect and x-ray crystallography. By analogy to the parent compound, the two 5-substituted tetrazole nucleosides are also assigned the beta configuration on the basis of the NMR coupling constant of the anomeric proton and the site of N-ribosylation is determined by 13C NMR studies. Results are also presented on antiviral testing of these synthetic tetrazole nucleosides against influenza A2/Asian/J-305 virus infection in mice.

8-Chloro-5,5-dimethyl-5,6-dihydrotetrazolo[1,5-c]quinazoline

“…For applications of tetrazole derivatives, see: Upadhayaya et al (2004); Poonian et al (1976); Ismail et al (2006); Mulwad & Kewat (2008); Uchida et al (1989). For ring conformations, see: Boeyens (1978).…”

“…A number of tetrazole derivatives were reported as to be antifungal agents (Upadhayaya et al, 2004), antiviral agents (Poonian et al, 1976), angiotensin II AT 1 receptor antagonists (Ismail et al, 2006), antibacterial agents (Mulwad & Kewat, 2008) and anti-ulcer agents (Uchida et al, 1989). On the basis of these considerations, our particular attention was directed to synthesize some tetrazole derivatives.…”

Three‐Component Synthesis of Tetrazolo Anthraquinone as a Representation of a New Heterocyclic System

“…Moreover, as one of the polynitrogen electron‐rich backbone heterocycles, tetrazoles occupy an outstanding position in the arena of therapeutic and pesticidal chemistry due to a diversity of biological and pharmacological activity ,. On one hand, Tetrazoles and its derivatives contain significant antiviral, antibacterial, antimicrobial, anti‐inflammatory, and anticancer properties, among them such prominent drug molecules as antihypertensive drugs Losartan and its resemblance or the peptidase inhibitor CGS‐26303; on the other hand, they also display various pesticidal activity and are used as insecticides, fungicides, and plant growth regulators …”

Synthesis of New Tetrazole Derivatives of Spiro‐ and Bis‐barbiturates

“…An alternate methodology to overcome these shortcomings was developed for the first time by Sharpless et al 2 5-Substituted-tetrazoles are reported to possess antibacterial, (17), 3 antifungal (TAK-456, 18), 4 antiviral (19), 5 analgesic (20), 6 anti-inflammatory (21), 7 antiulcer 8 and antihypertensive activities. 9 Some examples such as Irbesartan (22), Valsartan (23), Tasosartan (24), and Losartan (25) are shown in Fig.…”