TY - JOUR
T1 - Synthesis, Molecular Docking and Evaluation of 1,3,4-Oxadiazole-Isobenzofuran Hybrids as Antimicrobial and Anticancer Agents
AU - Nayak, Swarnagowri
AU - Gaonkar, Santosh L.
AU - Hazra, Druti
AU - Chawla, Kiran
AU - Hari, Gangadhar
AU - Pai, K. S.R.
AU - Guru, Bharath Raja
AU - Hakimane, Sushruta S.
N1 - Funding Information:
Swarnagowri Nayak gratefully acknowledge the Department of Science and Technology, Government of India (Sanction no. DST/INSPIRE Fellowship/2018/IF180662 dated 25‐09‐2019) for senior research fellowship under the DST‐INSPIRE scheme. Also, this work was supported by the Manipal Academy of Higher Education.
Funding Information:
Swarnagowri Nayak gratefully acknowledge the Department of Science and Technology, Government of India (Sanction no. DST/INSPIRE Fellowship/2018/IF180662 dated 25-09-2019) for senior research fellowship under the DST-INSPIRE scheme. Also, this work was supported by the Manipal Academy of Higher Education.
Publisher Copyright:
© 2022 Wiley-VHCA AG, Zurich, Switzerland.
PY - 2022/5
Y1 - 2022/5
N2 - In drug discovery, the hybridization of bioactive pharmacophores is a powerful tool for targeting enzymes involved in cancer and microbial cell growth. A combination of 1,3,4-oxadiazole and isobenzofuran may improve the antitumor and antimicrobial properties of the hybrid molecules. A series of hybrid molecules having 1,3,4-oxadiazole and isobenzofuran were synthesized and structural characterization was done by FT-IR, 1H-NMR, 13C-NMR, and mass spectrometry. Molecular docking studies were performed to investigate binding interactions of compounds with proteins (PDB NO: 2R3J and 1GII), and the results were consistent with in vitro anticancer data. All the synthesized compounds were tested for antimicrobial activity against S. aureus, E. faecalis (Gram-positive) and E. coli and P. aeruginosa (Gram-negative) bacterial strains. Among the synthesized compounds, 7a and 7b displayed good activity against the tested bacterial strains. Also, compounds were tested for their anti-tumor activity against breast cancer (MCF-7) and colon cancer (HCT-116) cell lines via SRB assay. In comparison to doxorubicin (1.14 μM), hybrids 7e (4.32 μM), 7f (4.15 μM), 7g (4.66 μM), and 7h (4.83 μM) demonstrated comparable IC50 value against the HCT 116 cell line.
AB - In drug discovery, the hybridization of bioactive pharmacophores is a powerful tool for targeting enzymes involved in cancer and microbial cell growth. A combination of 1,3,4-oxadiazole and isobenzofuran may improve the antitumor and antimicrobial properties of the hybrid molecules. A series of hybrid molecules having 1,3,4-oxadiazole and isobenzofuran were synthesized and structural characterization was done by FT-IR, 1H-NMR, 13C-NMR, and mass spectrometry. Molecular docking studies were performed to investigate binding interactions of compounds with proteins (PDB NO: 2R3J and 1GII), and the results were consistent with in vitro anticancer data. All the synthesized compounds were tested for antimicrobial activity against S. aureus, E. faecalis (Gram-positive) and E. coli and P. aeruginosa (Gram-negative) bacterial strains. Among the synthesized compounds, 7a and 7b displayed good activity against the tested bacterial strains. Also, compounds were tested for their anti-tumor activity against breast cancer (MCF-7) and colon cancer (HCT-116) cell lines via SRB assay. In comparison to doxorubicin (1.14 μM), hybrids 7e (4.32 μM), 7f (4.15 μM), 7g (4.66 μM), and 7h (4.83 μM) demonstrated comparable IC50 value against the HCT 116 cell line.
UR - http://www.scopus.com/inward/record.url?scp=85127588233&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85127588233&partnerID=8YFLogxK
U2 - 10.1002/cbdv.202100956
DO - 10.1002/cbdv.202100956
M3 - Article
C2 - 35304823
AN - SCOPUS:85127588233
SN - 1612-1872
VL - 19
SP - e202100956
JO - Chemistry and Biodiversity
JF - Chemistry and Biodiversity
IS - 5
M1 - e202100956
ER -
