Synthesis, anti-inflammatory, bactericidal activities and docking studies of novel 1,2,3-triazoles derived from ibuprofen using click chemistry.
BACKGROUND
Nonsteroidal anti-inflammatory drugs are of vast therapeutic benefit in the treatment of different types of inflammatory conditions. 1,2,3-Triazoles and their derivatives have a wide range of applications as anti-bacterial, anti-fungal, anti-tubercular, cytostatic, anti-HIV, anti-allergic, anti-neoplastic and anti-inflammatory (AI) agents. Considering the individual biological and medicinal importance of ibuprofen and 1,2,3-triazoles, we wanted to explore novel chemical entities based on ibuprofen and triazole moieties towards their biological significance.


RESULTS
Click chemistry has utilized as an ideal strategy to prepare novel ibuprofen-based 1,4-disubstituted 1,2,3-triazole containing molecules. These compounds were screened for their in vivo AI activity, among all the synthesized analogues 13o was shown potent effect than the reference AI drug ibuprofen at the same concentration (10 mg/kg body weight). Compounds 13l, 13g, 13c, 13k, 13i, 13n, 13m and 13j were shown significant AI activity. These triazole analogues were also screened for their bactericidal profile. Compounds 13c, 13i, 13l and 13o exhibited considerable bactericidal activity against gram positive and gram negative strains. In addition to this, molecular docking studies were also carried out into cyclooxygenase-2 active site to predict the affinity and orientation of these novel compounds (13a-q).


CONCLUSIONS
In summary, we have designed and synthesized 1,2,3-triazole analogues of ibuprofen in good yields using Click chemistry approach. AI and bactericidal activities of these compounds were evaluated and shown remarkable results.
Department of Chemistry, University College of Science, Saifabad, Osmania University, Hyderabad, Telangana 500004 India.
Kishore Kumar
KK
Angajala
Department of Chemistry, University College of Science, Saifabad, Osmania University, Hyderabad, Telangana 500004 India.
Sunitha
S
Vianala
Department of Chemistry, University College of Science, Saifabad, Osmania University, Hyderabad, Telangana 500004 India.
Ramesh
R
Macha
Department of Chemistry, University College of Science, Saifabad, Osmania University, Hyderabad, Telangana 500004 India.
M
M
Raghavender
Chaitanya College of Pharmacy Education and Research, Kishanpura, Hanamkonda, Warangal, Telangana 506001 India.
Murali Krishna
MK
Thupurani
Department of Chemistry, University College of Science, Saifabad, Osmania University, Hyderabad, Telangana 500004 India.
P J
PJ
Pathi
Anti-inflammatory; Bactericidal; Click chemistry; Docking; Ibuprofen; Triazoles