Novel isochroman-triazoles and thiadiazole hybrids: Design, synthesis and antimicrobial activity

Abstract

In this study, new isochroman-triazole (6a-e) and thiadiazole (7a-e) conjugates were obtained by heterocyclization of isochromanyl thiosemicarbazides (5a-e) under basic and acidic catalysis respectively. The latter were obtained by the treatment of corresponding acetohydrazide (4) with suitably substituted phenylisothiocyanates. The acetohydrazide (4) is accessible from methyl 2-(6,7,8-trimethoxy-1-methyl-3,4-dihydro-1H-isochromen-1-yl)acetate (3) obtainable by oxa-Pictet-Spengler reaction of 2-(3,4,5-trimethoxyphenyl)ethanol (2) with methyl acetoacetate in the presence of p-TsOH. The isochromanyl triazoles (6a-e) and isochromanyl thiadiazoles (7a-e) were screened for their in vitro antibacterial activity against four bacterial strains and were found to exhibit moderate to good activity toward the tested microorganisms, compared to ampicillin, the standard drug. In vitro antifungal activity was also determined against four fungal strains using fluconazole as standard and the most active compounds were identified in each case. ª 2015 Production and hosting by Elsevier B.V. on behalf of King Saud University. This is an open access article under the CC BY-NC-ND license (http://creativecommons.org/licenses/by-nc-nd/4.0/).

Novel Aldimine‐Type Schiff Bases of 4‐Amino‐5‐[(3,4,5‐trimethoxyphenyl)methyl]‐1,2,4‐triazole‐3‐thione/thiol: Docking Study, Synthesis, Biological Evaluation, and Anti‐Tubulin Activity

“…) . The hybrid structures of triazole ring and TMP moiety were also introduced as antitumor (compound 3 ) , antimicrobial (compound 4 ) , and antimitotic agents (compound 5 ) (Fig. ).…”

Tautomers of homophthalic anhydride in the ground and excited electronic states: analysis through energy, hardness and vibrational signatures

“…The antioxidant properties of one of its derivatives, 4-acyl isochroman-1, 3-diones, are well established by Saba et al [20]. The antifungal and antibacterial activities of its thiadiazole and triazole hybrids are established as well as its use as an inhibitor to microbial activities are well demonstrated [21]. The catalytic reactions of isochroman-1,3-diones with 4-dimethylaminopyridine are found to occur with isomerization process [22].…”

Hybrid Pharmacophore Design, Molecular Docking, Synthesis, and Biological Evaluation of Novel Aldimine‐Type Schiff Base Derivatives as Tubulin Polymerization Inhibitor

“…Furthermore, the TMP group is also present in the structure of trimetrexate and trimethoprim ( Figure ) identified as one of the most important inhibitor of human and prokaryotic dihydrofolate reductase (DHFR), respectively . In addition, the TMP ring exhibited the key role in the structure of many synthesized compounds evaluated for antimicrobial, anti‐HIV (by inhibition of reverse transcriptase activity), and antileishmanial activity …”