Synthesis and Antimicrobial Activity of Some New Thiadiazoles, Thioamides, 5-Arylazothiazoles and Pyrimido[4,5-d][1,2,4]triazolo[4,3-a]pyrimidines.

Abdou Abdelhamid,Ibrahim El Sayed,Mangoud Mangoud,Mohamed Hussein

doi:10.3390/molecules21081072

Abstract

A novel series of 1,3,4-thiadiazoles, 5-arylazothiazoles and hexahydropyrimido-[4,5-d][1,2,4]triazolo[4,3-a]pyrimidines were synthesized via reaction of hydrazonoyl halides with each of alkyl carbothioates, carbothioamides and 7-thioxo-5,6,7,8-tetrahydropyrimido-[4,5-d]pyrimidine-2,4(1H,3H)-diones in the presence of triethylamine. The structures of the newly synthesized compounds were established based on their spectral data, elemental analyses and alternative synthetic routes whenever possible. Also, the newly synthesized compounds were screened for their antimicrobial activity against various microorganisms.

Highlights

Hydrazonoyl halides have been widely used as reagents for the synthesis of heterocyclic compounds, both through condensation reactions, and as precursors of nitrilimines, which can undergo cycloaddition with dipolarophiles [1,2]. 1,3,4-Thiadiazoles are among the most common heterocyclic pharmacophores
Streptococcus pneumoniae was susceptible to compounds 13b, and 14b when compared to the Bacillus subtilis was susceptible to compounds 13b, 14b, and 15b when compared to the Pseudomonas aeruginosa was susceptible to compounds 13b, 15a, and 26d when compared to their standard Gentamicin
Streptococcus pneumoniae was susceptible to compounds 12b, 13b, and 14b when compared to an ampicillin standard

Summary

Introduction

Hydrazonoyl halides have been widely used as reagents for the synthesis of heterocyclic compounds, both through condensation reactions, and as precursors of nitrilimines, which can undergo cycloaddition with dipolarophiles [1,2]. 1,3,4-Thiadiazoles are among the most common heterocyclic pharmacophores. 1,3,4-Thiadiazoles are among the most common heterocyclic pharmacophores. Hydrazonoyl halides have been widely used as reagents for the synthesis of heterocyclic compounds, both through condensation reactions, and as precursors of nitrilimines, which can undergo cycloaddition with dipolarophiles [1,2]. They display a broad spectrum of biological activities, including antimicrobial [3]. 1,2,4-Triazolopyrimidines have attracted growing interest due to their important pharmacological activities, such as antitumor, antimalarial, antimicrobial, anti-inflammatory, antifungal properties, and their potency in macrophage activation [23,24,25,26,27] Thiazoles can found in drugs developed for the treatment of allergies [13], hypertension [14], inflammation [15], schizophrenia [16], bacterial infections [17], HIV [18], sleep disorders [19] and more recently, for the treatment of pain [20], as fibrinogen receptor antagonists with antithrombotic activity [21], and as new inhibitors of bacterial DNA gyrase B [22]. 1,2,4-Triazolopyrimidines have attracted growing interest due to their important pharmacological activities, such as antitumor, antimalarial, antimicrobial, anti-inflammatory, antifungal properties, and their potency in macrophage activation [23,24,25,26,27]

Methods

Results

Conclusion