Department of Chemistry and Research Centre, Telangana University, Nizamabad, Telangana-503322. India
A new series of 2-phenyl-3-(6-aryl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-3-yl)-4H-4-chromenone 1(a-j) has been synthesized by the reaction of 3(4-amino-5-sulfanyl-4H-1,2,4-triazol-3-yl)-2-phenyl-4H-4-chromenone with a variety of phenacyl bromides in ethanol under reflux. The compound with the 4-bromophenyl (1g) greatest anti A. niger action, while compound (1a) had the least. Except for 1a and 1i, these compounds also shown efficacy against Candida albicans. While others showed moderate to good action, the compound containing the 4-methoxyphenyl (1c) good activity against C. albicans.
Triazoles are the class of heterocyclic compounds1 their azole ring is readily able to bind with a variety of enzymes and receptors in biological system via diverse non-covalent interactions, and thus display versatile biological activities. Among the triazoles, 1,2,4-triazole have drawn great attention due to its wide variety of activities2, many drugs which containing triazole moiety available in market such as antifungal drugs myclobutanil3, tebuconazole4, posaconazole5, Itraconazole6, fluconazole7 and paclobutrazole8, anticancer drugs anastrazole9, litrozole10 and vorozole11, antimigrain drug rizatriptan12 and antiviral drug ribavirin13.
The 1,2,4-triazole substituted with amino and mercapto groups have been reported to possess a variety of biological activities such as antibacterial14, antifungal15, antitubercular16, anticancer17, diuretic18, and hypoglycemic19. The amino and mercapto groups are readymade nucleophilic centers for synthesis of fused heterocyclic systems20. Further, the triazole fused with thiadiazine have promising biological activities such as anti-HIV21, CNS stimulant22, antifungal23, and anti-inflammatory24 and anti-Candidal activity25.
MATERIAL AND METHODS:
Using the cup-plate method26, the compounds (figure 1) 1(a-j) were further tested for their antifungal activity against Aspergillus niger and Candida albicans at 100 g/mL. These compounds antifungal efficacy was compared to that of the accepted reference drug, Amphotericin B. The zones of inhibition that formed are shown in Table 1 and are measured in millimeters.
RESULTS AND DISCUSSION
Antifungal activity
Using the cup-plate method26, the compounds 1(a-j) were further tested for their antifungal activity against Aspergillus niger and Candida albicans at 100 g/mL. These compounds antifungal efficacy was compared to that of the accepted reference drug, Amphotericin B. The zones of inhibition that formed are shown in Table 1 and are measured in millimeters. All of the compounds had antifungal activity against A. niger, according to the antifungal screening findings. The compound with the 4-bromophenyl (1g) had the greatest anti A. niger action, while compound (1a) had the least. Except for 1a and 1i, these compounds also shown efficacy against Candida albicans. While others showed moderate to good action, the compound containing the 4-methoxyphenyl (1c) good activity against C. albicans.
Figure 1: A new series of 2-phenyl-3-(6-aryl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-3-yl)-4H-4-chromenone compounds 1(a-j).
Table 1: Antifungal Activity of Compounds 1(a-j)
|
Compound |
Ar |
Zones of inhibition (mm) at 100 g/Ml |
|
|
A. niger |
C. albicans |
||
|
1a |
Phenyl |
9 |
— |
|
1b |
4-methylphenyl |
13 |
9 |
|
1c |
4-methoxyphenyl |
12 |
14 |
|
1d |
3-methoxyphenyl |
10 |
10 |
|
1e |
4-chlorophenyl |
12 |
13 |
|
1f |
3,4-dichlorophenyl |
10 |
11 |
|
1g |
4-bromophenyl |
17 |
10 |
|
1h |
4-nitrophenyl |
14 |
12 |
|
1i |
3-nitrophenyl |
12 |
— |
|
1j |
4-hydroxyphenyl |
10 |
12 |
|
Amphotericin B |
— |
18 |
16 |
A new series of 2-phenyl-3-(6-aryl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-3-yl)-4H-4-chromenone 1(a-j) has been synthesized by the reaction of 3(4-amino-5-sulfanyl-4H-1,2,4-triazol-3-yl)-2-phenyl-4H-4-chromenone with a variety of phenacyl bromides in ethanol under reflux.27 The compound with the 4-bromophenyl (1g) greatest anti A. niger action, while compound (1a) had the least. Except for 1a and 1i, these compounds also shown efficacy against Candida albicans. While others showed moderate to good action, the compound containing the 4-methoxyphenyl (1c) good activity against C. albicans. The investigated compounds' activity, however, are lower than those of the commonly used standard antibacterial agent.
Conflicts of interest
There are no conflicts to declare.
ACKNOWDGEMENTS
The author is thankful to the head, Department of Chemistry, Telangana University, Nizamabad, Telangana, India, for support and facilities provided.
Financial support and sponsorship
Department of chemistry and research centre, Telangana University.
REFERENCES
G. Nageswara Rao, In Vitro Evaluation of Antifungal Activity of Series of 2-Phenyl-3-(6-aryl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-3-yl)-4H-4-chromenone Compounds, Int. J. of Pharm. Sci., 2024, Vol 2, Issue 11, 1563-1566. https://doi.org/10.5281/zenodo.14236228
10.5281/zenodo.14236228
