- Visibility 60 Views
- Downloads 18 Downloads
- DOI 10.18231/j.jpbs.2021.016
-
CrossMark
Synthesis, characterization and antimicrobial activity of novel tetrazoles clubbed with pyrimidine
Introduction
Since they are a diverse group of natural and synthetic products, many of which have biological applications, nitrogen-containing heterocycles are extremely important. Pyrimidine, which is present in DNA and RNA, has a variety of pharmacological properties, including bactericide, fungicide, vermicide, insecticide, anticancer, and antiviral.[1] Some pyrimidine derivatives reported as Anti-HIV-1 agents,[2] antileishmanial,[3]Anti-inflammatory,[4] Anticancer,[5] antimicrobial Antimalarial.[6] To date, a wide range of pyrimidine and pyrimidine-fused heterocyclic compounds have been documented to have anticancer activity through a variety of mechanisms and targets.[7], [8], [9] Pyrimidine derivatives [10], [11] have played a significant role in the evolution of heterocyclic chemistry and have been widely used as pharmacophores and synthons in organic chemistry. A considerable amount of research effort has been centered on these nuclei due to their flexible chemotherapeutic significance. There has been significant progress in this area since the discovery of many synthetic and semi-synthetic antibacterial sulfa products, nitrofuranes, penicillins, cephalosporins, tetracyclines, macrolides, oxazolidinones, and antifungal agents such as fluconazole, ketoconazole, and miconazole, as well as amphotericin B. Despite advancements in antibacterial and antifungal therapies, most antimicrobial drugs still have a long way to go. Antibiotic overuse has resulted in the emergence of multidrug-resistant microbial pathogens.[12] Pyrimidine based heterocycles are potential bioactive molecules and exhibit antimicrobial,[13], [14] anti-inflammatory,[11] antioxidant,[15] anticancer,[16] antihypertensive[17] and anticonvulsant.[18] Tetrazole has a great importance as it is bioactive molecules and exhibit antimicrobial,[19] anti-bacterial[20] anti-inflammatory[21], antioxidant,[22] anticancer[23] ant tubercular,[24] anti-fungal,[24] antihypertensive[25], anticonvulsant[26] and also act as enzyme inhibitors. Inspired from these facts, in present work an attempt is being made to synthesize pyrimidine’s containing tetrazole and evaluate for antimicrobial activity which has not been reported yet. Hence the present work deals with the reaction of 1-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl] ethanone (1) with different aromatic aldehydes in presence of alkaline medium to form (2E)-1-[5-(2,6-dimethylphenyl)- 1H-tetrazol-1-yl]-3-(substituted aryl)prop-2-en-1-one (2a-f). Reaction of (2a-f) with urea and thiourea to produce 5-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]-4-(substituted aryl )pyrimidin-2-ol (3a-f) and 5-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]- 4-(substituted aryl) pyrimidin-2-thiol (4a-f) respectively. The structure of all the various synthesized compounds were assigned on the basis of IR, 1H NMR spectral data and elemental analysis. These compounds were screened for their antimicrobial activity.
Materials and Methods
Melting points were determined with open capillary. FT-IR spectra were recorded on a Jasco model 4010 spectrophotometer,1H NMR spectra were recorded in DMSO on a Varian mercury FT-NMR model YH- 300 instrument using TMS as internal standard. Mass spectra were recorded on GC-MS auto tune EI instrument.
Synthetic procedur
General procedure for the preparation (2E)-1-[5-(2,6-dimethylphenyl)- 1H-tetrazol-1-yl]-3-(substituted aryl) prop-2-en-1-one derivatives [2a-f]
A solution of 5-(2,6-dimethylphenyl)-1H-tetrazole (8.5g,0.05 moles) and heterocyclic aldehydes (0.05 mole) in ethanol (12 ml) was cooled to 5 to 10oC in an ice bath. The cooled solution was treated with drop wise addition of aqueous sodium hydroxide (5 ml, 50%). The reaction mixture was magnetically stirred for 30 min and then left over night. The resulting dark solution was diluted with ice water and carefully acidified using diluted hydrochloric acid. The tetrazole analogues of chalcone which crystallized were collected by filtration after washing with sodium bicarbonate and water. It was further purified by crystallization from ethanol.
Synthesis of 5-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]-4- (substituted ary) pyrimidin-2-ol derivatives [3a-f]
To a solution of 2E)-1-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]- 3-(substituted aryl)prop-2-en-1-one derivatives (2a-f), (0.01mole) in anhydrous ethanol (50 mL), urea (0.01 mole)and aqueous sodium hydroxide (0.01 mole). The reaction mixture was refluxed for 5 hrs and poured into ice cold water the product obtained was filtered, washed with water and crystallized from aqueous ethanol. The purity of the compound was established by TLC using a mixture of hexane and ethyl acetate (7:3) as a mobile phase.
Synthesis of 5-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]-4- (substituted aryl) pyrimidin-2-thiol derivatives [4a-f]
To a solution of 2E)-1-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]-3- (substituted aryl) prop-2-en-1-one derivatives (2a-f), (0.01mole) in anhydrous ethanol (50 mL), thiourea (0.01 mole) and aqueous sodium hydroxide (0.01 mole). The reaction mixture was refluxed for 5 hrs and poured into ice cold water the product obtained was filtered, washed with water and crystallized from aqueous ethanol. The purity of the compound was established by TLC using a mixture of hexane and ethyl acetate (6:4) as a mobile phase.
Antibacterial and antifungal activity
All the newly synthesized compounds were screened for antimicrobial activity against both gram positive S. aureus and gram negative E.coli bacteria and antifungal activity against C. albicans and A. niger according to cup plate method[13] at a concentration 100ug/0.1ml respectively. Streptomycin and clotrimazole were used as standard for comparison of antibacterial and antifungal activity[14] Indian Pharmacopoeia[15]. Solvent dimethyl sulphoxide (DMSO) was used as control. The results of screening are given in[Table 2].
|
Comp no |
R |
Mole. Formula |
MW |
% Yield |
M.P.0C |
Rf. |
Found (Calcd) % |
||
|
C |
H |
N |
|||||||
|
3a |
Fig1 |
C17H15N70 |
333 |
72 |
164 |
0.64 |
61.20 (61.25) |
4.50 (4.54) |
29.39 (29.41) |
|
3b |
Fig2 |
C17H14N602 |
334 |
62 |
172 |
0.65 |
61.04 (61.07) |
4.20 (4.22) |
25.12 (25.14) |
|
3c |
Fig3 |
C18H16N602 |
348 |
65 |
174 |
0.73 |
62.01 (62.06) |
4.60 (4.63) |
24.08 (24.12) |
|
3d |
Fig4 |
C18H16N60S |
364 |
60 |
166 |
0.68 |
59.29 (59.32) |
4.38 (4.43) |
23.04 (23.06) |
|
3e |
Fig5 |
C18H16N60S |
364 |
64 |
164 |
0.65 |
59.29 (59.32) |
4.38 (4.43) |
23.04 (23.06) |
|
3f |
Fig6 |
C18H15N70 |
345 |
74 |
150 |
0.75 |
62.57 (62.60) |
4.33 (4.38) |
28.36 (28.39) |
|
4a |
Fig7 |
C17H14N7S |
348 |
72 |
166 |
0.62 |
58.41 (58.44) |
4.29 (4.33) |
28.03 (28.06) |
|
4b |
Fig8 |
C17H16N6OS |
350 |
66 |
180 |
0.66 |
58.22 (58.27) |
4.00 (4.03) |
23.95 (23.98) |
|
4c |
Fig9 |
C18H16N60S |
364 |
68 |
178 |
0.72 |
59.26 (59.32) |
4.41 (4.43) |
23.05 (23.06) |
|
4d |
Fig10 |
C18H16N6S2 |
380 |
65 |
166 |
0.68 |
56.80 (56.82) |
4.20 (4.24) |
22.06 (22.09) |
|
4e |
Fig11 |
C18H16N6S2 |
380 |
64 |
168 |
0.58 |
56.76 (56.82) |
4.22 (4.24) |
25.04 (22.09) |
|
4f |
Fig12 |
C18H15N7S |
361 |
72 |
185 |
0.75 |
59.77 (59.82) |
4.14 (4.18) |
27.10 (27.13) |
|
Comp. |
Zone of inhibition in mm at 100 µg/0.1ml |
|||
|
|
S. aureus |
E. coli |
C. albicans |
A. niger |
|
3a |
14 |
12 |
20 |
18 |
|
3b |
15 |
13 |
20 |
16 |
|
3c |
18 |
16 |
21 |
15 |
|
3d |
16 |
14 |
18 |
13 |
|
3e |
18 |
15 |
21 |
22 |
|
3f |
20 |
18 |
16 |
12 |
|
4a |
16 |
13 |
15 |
13 |
|
4b |
16 |
14 |
20 |
16 |
|
4c |
18 |
17 |
20 |
14 |
|
4d |
16 |
15 |
18 |
12 |
Synthesis and spectral characterization
A series of 5-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]-4-(substituted aryl) pyrimidin-2-ol (3a-f) and 5-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]-4-(substituted aryl) pyrimidin-2-thiol (4a-f) were synthesized from chalcones of 5-(2,6-dimethylphenyl)-1H-tetrazole. All synthesis steps are presented in scheme 1. The IR spectra shows 1542 (C=N), 1445(C=C) providing the strong evidence for pyrimidine ring. 1H NMR spectrum shows 7.10-7.58 ppm for aromatic protons and 9.7 ppm for OH protons and 13.4 for SH protons were observed at expected signals.
3a:5-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]-4-(1H-pyrrol-2-yl)pyrimidin-2-ol
IR: 3745 (OH), 3050 (Ar-CH), 1540(C=N), 1435(C=C), 1286(N-N=N-),1120 and 1145(Tetrazole ring),.1H NMR: 2.35 (d, 6H, CH3), 6.5-6.8 (d,1H,CH=CH) 7.30 -8.40 (m ,8H, Ar-H), 9.5 (1H, Ar- OH), Mass spectrum (m/z) molecular ion peak at 332 and isotopic peak at 333.
3b: 5-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]-4-(furan-2-yl)pyrimidin-2-ol:
IR: 3744 (OH), 3054 (Ar-CH), 1538 (C=N), 1436(C=C), 1280 (N-N=N-),1120 and 1145(Tetrazole ring) , 780(C-Cl)., 1H NMR: 2.35 (d, 6H, CH3), 6.5-6.8 (d,1H,CH=CH) 7.30 -8.40 (m ,7H, Ar-H), 9.5 (1H, Ar- OH), Mass spectrum (m/z) molecular ion peak at 334 and and isotopic peak at 315.
3c: 5-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]-4-(5-methylfuran-2-yl)pyrimidin-2-ol:
IR: 3742 (OH), 3056 (Ar-CH), 1536 (C=N), 1432(C=C), 1282(N-N=N-),1245(-OCH3) ,1120 and 1145(Tetrazole ring) , 1H NMR: 2.35 (d, 9H, CH3), 6.5-6.8 (d,1H,CH=CH) 7.30 -8.40 (m ,7H, Ar-H), 9.5 (1H, Ar- OH),, Mass spectrum (m/z) molecular ion peak at 348.
3d: 5-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]-4-(5-methylthiophen-2-yl)pyrimidin-2-ol
IR: 3740 (OH), 3058 (Ar-CH), 1546 (-NO2),1530(C=N), 1441(C=C), 1278 (N-N=N-),1120 and 1145(Tetrazole ring) , 1H NMR: 2.35 (d, 9H, CH3), 6.5-6.8 (d,1H,CH=CH) 7.30 -8.40 (m ,7H, Ar-H), 9.5 (1H, Ar- OH),, Mass spectrum (m/z) molecular ion peak at 364.
3e:5-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]-4-(3-methylthiophen-2-yl)pyrimidin-2-ol
IR: 3735 (OH), 3054 (Ar-CH), 1544(C=N), 1435(C=C), 1331(-N(CH3)2,1284 (N-N=N-),1120 and 1145(Tetrazole ring) , 1H NMR: 2.35 (d, 9H, CH3), 6.5-6.8 (d,1H,CH=CH) 7.30 -8.40 (m,7H, Ar-H), 9.5 (1H, Ar- OH), Mass spectrum (m/z) molecular ion peak at 364.
3f: 5-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]-4-(pyridin-2-yl)pyrimidin-2-ol
IR: 3741 (OH), 3052 (Ar-CH), 1544 (C=N), 1436(C=C), 1355(CH3),1284 (N-N=N-),1120 and 1145(Tetrazole ring), 1H NMR: 2.35 (d, 6H, CH3), 6.5-6.8 (d,1H,CH=CH) 7.30 -8.40 (m ,9H, Ar-H), 9.5 (1H, Ar- OH), Mass spectrum (m/z) molecular ion peak at 345.
4a:5-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]-4-(1H-pyrrol-2-yl)pyrimidin-2-thiol
IR:3055 (Ar-CH), 1538(C=N), 1436(C=C), 1288 (N-N=N-), 1120 and 1145 (Tetrazole ring) , 1H NMR: 2.35 (d, 6H, CH3), 6.5-6.8 (d,1H,CH=CH) 7.30 -8.40 (m ,8H, Ar-H), 13.6 (s, 1H, SH), Mass spectrum (m/z) molecular ion peak at 348.
4b: 5-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]-4-(furan-2-yl)pyrimidin2-thiol
IR: 3050 (Ar-CH), 1535(C=N), 1436(C=C), 1286(N-N=N-),1120 and 1145 (Tetrazole ring), 780 (C-Cl)., 1H NMR: 2.35 (d, 8H, CH3), 6.5-6.8 (d,1H,CH=CH) 7.30 -8.40 (m, 8H, Ar-H), 13.6 (s, 1H, SH), Mass spectrum (m/z) molecular ion peak at 350.
4c:5-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]-4-(5-methylfuran-2-yl)pyrimidin-2-thiol
IR: 3052 (Ar-CH), 1544(C=N), 1448(C=C), 1286(N-N=N-),1245(-OCH3), 1120 and 1145(Tetrazole ring) , 1H NMR: 2.35 (d, 9H, CH3), 6.5-6.8 (d,1H,CH=CH) 7.30 -8.40 (m ,7H, Ar-H), 13.6 (s, 1H, SH), Mass spectrum (m/z) molecular ion peak at 364.
4d:45-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]-4-(5-methylthiophen-2-yl)pyrimidin-2-thiol
IR: 3058 (Ar-CH), 1543(C=N), 1560(-NO2),1442(C=C), 1286(N-N=N-), 1120 and 1145(Tetrazole ring), 1H NMR: 2.35 (d, 9H, CH3), 6.5-6.8 (d,1H,CH=CH) 7.30 -8.40 (m ,7H, Ar-H), 13.6 (s, 1H, SH), Mass spectrum (m/z) molecular ion peak at 380.
4e:5-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]-4-(3-methylthiophen-2-yl)pyrimidin-2-thiol
IR:3050 (Ar-CH), 1542(C=N), 1442(C=C), 1331(-N(CH3)2,1286(N-N=N-), 1120 and 1145 (Tetrazole ring), 1H NMR: 2.35 (d, 9H, CH3), 6.5-6.8 (d,1H,CH=CH) 7.30 -8.40 (m,7H, Ar-H), 13.6 (s, 1H, SH), Mass spectrum (m/z) molecular ion peak at 380 and isotopic peak at 381.
4f:5-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]-4-(pyridin-2-yl)pyrimidin-2-thiol
IR: 3051(Ar-CH), 1540(C=N), 1442(C=C), 1355(CH3),1286(N-N=N-),1120 and 1145(Tetrazole ring), 1H NMR: 2.35 (d, 9H, CH3), 6.5-6.8 (d,1H,CH=CH) 7.30 -8.40 (m, 9H, Ar-H), 13.6 (s, 1H, SH), Mass spectrum (m/z) molecular ion peak at 361.
Results and Discussion
The reaction of 5-(2,6-dimethylphenyl)-1H-tetrazole with acetic anhydride to yield 1-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl] ethanone (1) and which then treated with different aromatic aldehydes in presence of alkaline medium to form(2E)-1-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]-3-(substituted aryl) prop-2- en-1-one (2a-f). Reaction of (2a-f) with urea and thiourea to produce 5-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]-4-(substituted aryl ) pyrimidin-2-ol (3a-f) and 5-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]-4-(substituted aryl )pyrimidin-2-thiol (4a-f) respectively. The FT-IR spectra of (3a-f) and (4a-f) showed the absence of peak of keto groups and the new peaks which appeared at 3510 cm-1 due to OH group. This signifies the keto enol tautomeric in synthesized compounds. Some spectral data are listed in Table 2. The FT-IR absorption bands disappearance at (1610-1650) cm-1 is give good evidence for the success step of reaction. These absorption bands due to (NH) amine group stretching frequency is at 3450 cm-1. Also FT-IR spectra of tetrazole showed clear absorption bands at 1286(N-N=N-),1120 and 1145 (Tetrazole ring). The NMR spectra of all the synthesized compounds were determined and the chemical shift values of H1 NMR shows at 2.35 (d, 9H, CH3), 6.5-6.8 (d,1H, CH=CH) 7.30 -8.40 (m, 9H, Ar-H), 9.5 (1H, Ar- OH), 13.6 (s, 1H, SH),. This values indicates the presence of all protons which conforms the structure of the synthesized compounds.
Antibacterial and antifungal activity
The antibacterial activity was evaluated by zone of inhibition method at 100 µg/0.1ml concentration. The results of antibacterial were compared with standard drug ciprofloxacin. Most of the synthesized compounds showed antibacterial activity against the tested Bacteria. It is evident that most of the compounds are very weakly active and few are moderately active against S. aureus and E. coli but compounds 3c, 3d and 3f and compounds 4c, 4d and 4f possess very good activity against S. aureus and E. coli at concentration of 100ug/0.1ml.
Similarly, the results of preliminary antifungal bioassays were compared with standard drug clotrimazole. Most of the synthesized compounds showed antifungal activity against the tested fungi. It is evident that the compounds 3e, 3c and 3a and compounds 4e,4b and 4c possess very good activity against fungi Candida albicans and Aspergillus niger at concentration of 100ug/0.1mL.Compound 3d and 4f showed moderate activity all bacteria and fungi tested
Conclusion
Tetrazole and Pyrimidine an important group of heterocyclic compounds reported to have different biological activities and hence the present studies were undertaken in order to synthesize Tetrazole clubbed with pyrimidines in order to potentiate the combined therapeutic effect of both heterocyclic compounds. So all the synthesized compounds were investigated them for their antibacterial and antifungal activity. Compounds with thiopene, furan and pyrrole substituents on pyrimidine clubbed with Tetrazole exhibited significant antibacterial and antifungal activity when compared with control. The compounds with pyrimidines substituents groups showed significant activity when compared to standard drug ciprofloxacin and clotrimazole respectively.
Source of Funding
None.
Conflict of Interest
None.
References
- A L Stuart, N K Ayisi, G Tourigny, V S Gupta. Antiviral activity, antimetabolic activity, and cytotoxicity of 3′-substituted deoxypyrimidine nucleosides. J Pharm Sci 1985. [Google Scholar] [Crossref]
- S Kumar, B Narasimhan. Therapeutic potential of heterocyclic pyrimidine scaffolds. Chem Cent J 2018. [Google Scholar] [Crossref]
- S N Suryawanshi, S Kumar, R Shivahare, S Pandey, A Tiwari, S Gupta. Design, synthesis and biological evaluation of aryl pyrimidine derivatives as potential leishmanicidal agents. Bioorganic Med Chem Lett 2013. [Google Scholar] [Crossref]
- N M Ahmed, S Nofal, S M Awad. Synthesis, Molecular Modelling and Biological Evaluation of Novel Pyrimidine Derivatives as Anti-inflammatory Agents. J Pharm Res Int 2020. [Google Scholar] [Crossref]
- F Sherbiny. Synthesis and Biological Evaluation of Novel Pyrazolo[3,4-D]Pyrimidine Derivatives of Expected Anticancer Activity. Al-Azhar J Pharm Sci 2021. [Google Scholar] [Crossref]
- A Agarwal, S Chauhan, N Ashutosh, P M S Goyal. Design, synthesis and biological evaluation of aryl pyrimidine derivatives as potential leishmanicidal agents. Bioorganic Med Chem 2005. [Google Scholar]
- V Sharma, N Chitranshi, A K Agarwal. Significance and Biological Importance of Pyrimidine in the Microbial World. Int J Med Chem 2014. [Google Scholar] [Crossref]
- T Tauchi, K Ohyashiki. The second generation of BCR-ABL tyrosine kinase inhibitors. Int J Hematol 2006. [Google Scholar] [Crossref]
- T Selvam, C James, P Vijaysarathy, S K Dniandev. A mini review of pyrimidine and fused pyrimidine marketed drugs. Res Pharm 2012. [Google Scholar]
- A Solankee, K Kapadia, A Ćirić, M Soković, I Doytchinova, A Geronikaki. Synthesis of some new S-triazine based chalcones and their derivatives as potent antimicrobial agents. Eur J Med Chem 2010. [Google Scholar]
- S M Sondhi, M Dinodia, R Rani, R Shukla, R Raghubir. Synthesis, anti-inflammatory and analgesic activity evaluation of some pyrimidine derivatives. Indian J Chem Sec B Org Med Chem 2009. [Google Scholar] [Crossref]
- J M Frère. Beta-lactamases and bacterial resistance to antibiotics. Mol Microbiol 1995. [Google Scholar]
- N R Mohamed, M M T Saidi, Y M Ali, M H Elnagdi. Utility of 6-amino-2-thiouracil as a precursor for the synthesis of pyrido[2,3-d]pyrimidines and their in vitro and in vivo biological evaluation. Sci Pharm 2007. [Google Scholar] [Crossref]
- Y A H Mostafa, M A Hussein, A A Radwan, A E H N Kfafy. Synthesis and antimicrobial activity of certain new 1,2,4-triazolo[1,5-a] pyrimidine derivatives. Arch Pharm Res 2008. [Google Scholar] [Crossref]
- C M Bhalgat, M Ali, B Ramesh, G Ramu. Novel pyrimidine and its triazole fused derivatives: Synthesis and investigation of antioxidant and anti-inflammatory activity,” Arab. J Chem 2014. [Google Scholar]
- M M Mohamed, A K Khalil, E M Abbass, A M El-Naggar. Design, synthesis of new pyrimidine derivatives as anticancer and antimicrobial agents. Synth Commun 2017. [Google Scholar] [Crossref]
- A M Farghaly, O M Aboulwafa, Y A M Elshaier, W A Badawi, H H Haridy, H A E Mubarak. Design, synthesis, and antihypertensive activity of new pyrimidine derivatives endowing new pharmacophores. Med Chem Res 2019. [Google Scholar]
- O Alam, P Mullick, S P Verma, S J Gilani. Synthesis, anticonvulsant and toxicity screening of newer pyrimidine semicarbazone derivatives. Eur J Med Chem 2010. [Google Scholar] [Crossref]
- M A A Radwan, M A Alshubramy, M A Motaal, B A Hemdan, D S El-Kady. Synthesis, molecular docking and antimicrobial activity of new fused pyrimidine and pyridine derivatives. Bioorg Chem 2019. [Google Scholar] [Crossref]
- A F Abbass, E H Zimam. Synthesis, characterization and study biological activity of some new pyrimidine and 1, 2, 3, 4-tetrazole derivatives based on sulfadiazine. Int J ChemTech Res 2016. [Google Scholar]
- P Mohite, R B Pandhare, S G Khanage, V H Bhaskar. Synthesis and Anti-Inflammatory Activity of Some 5-Phenyl-1-(Acyl)-1, 2, 3, 4-Tetrazole. J Pharm Res 2010. [Google Scholar]
- J G Leal. Synthesis and electrochemical and antioxidant properties of chalcogenocyanate oxadiazole and 5-heteroarylchalcogenomethyl-1: H -tetrazole derivatives. New J Chem 2017. [Google Scholar]
- V H Bhaskar, P B Mohite. Synthesis, characterization and evaluation of anticancer activity of some tetrazole derivatives. J Optoelectron Biomed Mater 2010. [Google Scholar]
- S Vembu, P Pavadai, M Gopalakrishnan. Synthesis , in vitro antifungal and antitubercular evaluation of novel amino pyrimidines based tetrazole derivatives. J Pharm Res 2014. [Google Scholar]
- R Vellalacheruvu, S Leela. Novel Route for Synthesis of Antihypertensive Activity of Tetrazole Analogues as a Carbamate and Urea Derivatives. Med Chem 2017. [Google Scholar] [Crossref]
- D C Liu, H J Zhang, C M Jin, Z S Quan. Synthesis and biological evaluation of novel benzothiazole derivatives as potential anticonvulsant agents. Molecules 2016. [Google Scholar] [Crossref]
- Introduction
- Materials and Methods
- Synthetic procedur
- General procedure for the preparation (2E)-1-[5-(2,6-dimethylphenyl)- 1H-tetrazol-1-yl]-3-(substituted aryl) prop-2-en-1-one derivatives [2a-f]
- Synthesis of 5-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]-4- (substituted ary) pyrimidin-2-ol derivatives [3a-f]
- Synthesis of 5-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]-4- (substituted aryl) pyrimidin-2-thiol derivatives [4a-f]
- Antibacterial and antifungal activity
- Synthesis and spectral characterization
- 3a:5-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]-4-(1H-pyrrol-2-yl)pyrimidin-2-ol
- 3b: 5-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]-4-(furan-2-yl)pyrimidin-2-ol:
- 3c: 5-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]-4-(5-methylfuran-2-yl)pyrimidin-2-ol:
- 3d: 5-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]-4-(5-methylthiophen-2-yl)pyrimidin-2-ol
- 3e:5-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]-4-(3-methylthiophen-2-yl)pyrimidin-2-ol
- 3f: 5-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]-4-(pyridin-2-yl)pyrimidin-2-ol
- 4a:5-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]-4-(1H-pyrrol-2-yl)pyrimidin-2-thiol
- 4b: 5-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]-4-(furan-2-yl)pyrimidin2-thiol
- 4c:5-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]-4-(5-methylfuran-2-yl)pyrimidin-2-thiol
- 4d:45-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]-4-(5-methylthiophen-2-yl)pyrimidin-2-thiol
- 4e:5-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]-4-(3-methylthiophen-2-yl)pyrimidin-2-thiol
- 4f:5-[5-(2,6-dimethylphenyl)-1H-tetrazol-1-yl]-4-(pyridin-2-yl)pyrimidin-2-thiol
- Results and Discussion
- Conclusion
- Source of Funding
- Conflict of Interest