Synthesis of Novel Halobenzyloxy and Alkoxy 1,2,4-Triazoles and Evaluation for Their Antifungal and Antibacterial Activities

Abstract

A new class of halobenzyloxy or alkoxy 1,2,4-triazoles and their hydrochlorides were synthesized through cyclization starting from commercially available phenylhydrazine. The structures were characterized by MS, IR and 1 H NMR spectra as well as elemental analyses. All the synthesized compounds were screened for their antibacterial activities in vitro against Staphylococcus aureus (ATCC29213), methicillin-resistant Staphylococcus aureus (N315), Bacillus subtilis, Escherichia coli (ATCC25922), Pseudomonas aeruginosa, Shigella dysenteriae, Eberthella typhosa, and antifungal activities against Candida albicans (ATCC76615), Aspergillus fumigatus by broth microdilution assay method. The results of preliminary bioassay indicated that 3-(2,4-difluorobenzyloxy)-1-phenyl-1H-1,2,4-triazole hydrochloride exhibited the best inhibitory activity with an MIC value of 56.25 µM against P. aeruginosa superior to Chloramphenicol, and showed comparable activity with Chloramphenicol against E. coli (ATCC25922).

Microwave‐Assisted Synthesis of Novel Symmetric Bis‐1,2,4‐triazolin‐3‐ones as Potent Inhibitors of CYP51: An Antifungal Activity Study

“… In case of bis‐1,2,4‐triazole derivatives, the triazole ring efficiently control the physicochemical properties which seem to possess good drug‐like properties and is revealed by its presence in many marketed antifungal drugs viz., Itraconazole, Posaconazole, TAK187, and Syn2869 Figure Methoxy group was introduced in target compounds as it enhances pharmacological properties by increasing the rate of absorption and transport of sample in vivo and they can also bind with the prosthetic group iron (II) ion of cytochrome P450 Triazolyl ring also improves the binding capability with active sites of target enzymes which affect the biological activities, as evidenced by exhibition of some triazolyl derivatives with good antimicrobial activities .…”

“…Methoxy group was introduced in target compounds as it enhances pharmacological properties by increasing the rate of absorption and transport of sample in vivo and they can also bind with the prosthetic group iron (II) ion of cytochrome P450 …”

(Benzylideneamino)triazole–Thione Derivatives of Flurbiprofen: An Efficient Microwave-Assisted Synthesis and In Vivo Analgesic Potential

“…37,38 wR2 = 0.116 (all data, 277 parameters); R1 = 0.040 [5213 data with F 2 > 2σ(F 2 )]. The F atom was modeled as two-fold disordered at atoms C( 14) and C( 16) with major occupancy {75.5(2)%}at C (14). CCDC 1511104 contains the supplementary crystallographic data for this paper.…”

Recent Development of Benzotriazole-based Medicinal Drugs

“…In view of this, the novel benzotriazole derivative 14 as a fluconazole analog was synthesized and could inhibit the growth of C. arachidicoa in percentage of 62.7%, which was better than the commercial fungicide difenoconazole. However, the replacement of benzotriazole ring by other moiety with smaller groups such as alkyl amino, alkoxy, triazolyl or substituted benzyl substituents could favorably inhibit the oxidative remove of sterol C( 14) methyl groups by the cytochrome P450 enzyme, thus enhancing the antifungal activity [67,68].…”