Synthesis, carbonic anhydrase inhibition, anticancer activity, and molecular docking studies of 1,3,4-oxadiazole derivatives

Vanjare, Balasaheb D.; Choi, Nam Gyu; Eom, Young Seok; Raza, Hussain; Hassan, Mubashir; Lee, Ki Hwan; Kim, Song Ja

doi:10.1007/s11030-022-10416-6

Cited by 10 publications

(8 citation statements)

References 53 publications

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“…There are various cytosolic forms (CA I, II, III, and IV) seen in mammals. Four of these forms are membrane‐bound (CA IV, IX, XII, and XIV), secreted (CA VI), and mitochondrial (CA VA, VB) [4] . Fluctuations in CA expression levels can cause cancer, neuropathic pain, altitude sickness, glaucoma, epilepsy, hypertension, and more.…”

Section: Introductionmentioning

confidence: 99%

Imidazole‐hydrazone derivatives: Synthesis, characterization, X‐ray structures and evaluation of anticancer and carbonic anhydrase I–II inhibition properties

et al. 2023

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The nine new imidazole-hydrazone derivatives of Schiff base were synthesized from the condensation reactions of 1-methyl-1H-imidazole-2-carbaldehyde with various substitutedhydrazide derivatives. Structures of the final compounds (1 a-1 i) were characterized by using 1 H NMR, 13 C NMR spectroscopic techniques, elemental analysis, and crystal X-ray diffraction. The in vitro carbonic anhydrase I and II potentials of these synthesized were evaluated. The result suggests that compound 1 a, a 4-methoxy substituted analog with an IC 50 of 0.949 μM, was found to have the most potent hCA I inhibitory activity. Compounds 1 c, 1 d, and 1 h were the most potent compounds on hCA II with IC 50 values of 3.330, 4.454, and 5.66 μM, respectively. All compounds were examined for their cytotoxicity towards human colorectal adenocarcinoma cell (HT29) and rat glioma cell line (C6) compared to mouse fibroblast normal cell line (L929) using the MTT assay method. The compounds 1 a, 1 d, and 1 i exhibited significant antiproliferative activity with less toxicity to a health cell line. Consequently, compound 1 a could be the potential lead for emerging selective cytotoxic compounds directing hCA I. Compound 1 d could be the potential lead for emerging selective cytotoxic compounds directing hCA II.

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Section: Introductionmentioning

confidence: 99%

Imidazole‐hydrazone derivatives: Synthesis, characterization, X‐ray structures and evaluation of anticancer and carbonic anhydrase I–II inhibition properties

et al. 2023

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“…The resulting product is a thioether with a new alkyl or aryl group attached to the sulfur atom of the 1,3,4‐oxadiazole‐2‐thiol ( 2 ) through –CH 2 linkage (Figure 2). [ 28 ] This type of reaction is widely used in organic synthesis to create and modify existing molecules. The structures of the synthetic molecules are characterized using EI‐MS, HREI‐MS, 1 H‐NMR, 13 C‐NMR, and 2D NMR techniques.…”

Section: Resultsmentioning

confidence: 99%

“…2). [28] This type of reaction is widely used in organic synthesis to create and modify existing molecules. The structures of the synthetic molecules are characterized using EI-MS, HREI-MS, 1 H-NMR, 13 C-NMR, and 2D F I G U R E 1 Rationale of the current study.…”

Section: Introductionmentioning

confidence: 99%

Multitargeted inhibition of key enzymes associated with diabetes and Alzheimer's disease by 1,3,4‐oxadiazole derivatives: Synthesis, in vitro screening, and computational studies

Fatima,

Saleem,

Salar

et al. 2023

Archiv der Pharmazie

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A library of 22 derivatives of 1,3,4‐oxadiazole‐2‐thiol was synthesized, structurally characterized, and assessed for its potential to inhibit α‐amylase, α‐glucosidase, acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and antioxidant activities. Most of the tested compounds demonstrated good to moderate inhibition potential; however, their activity was lower than that of the standard acarbose. Significantly, compound 3f exhibited the highest inhibition potential against α‐glucosidase and α‐amylase enzymes, with IC50 values of 18.52 ± 0.09 and 20.25 ± 1.05 µM, respectively, in comparison to the standard acarbose (12.29 ± 0.26; 15.98 ± 0.14 µM). Compounds also demonstrated varying degrees of inhibitory potential against AChE (IC50 = 9.25 ± 0.19 to 36.15 ± 0.12 µM) and BChE (IC50 = 10.06 ± 0.43 to 35.13 ± 0.12 µM) enzymes compared to the standard donepezil (IC50 = 2.01 ± 0.12; 3.12 ± 0.06 µM), as well as DPPH (IC50 = 20.98 ± 0.06 to 52.83 ± 0.12 µM) and ABTS radical scavenging activities (IC50 = 22.29 ± 0.18 to 47.98 ± 0.03 µM) in comparison to the standard ascorbic acid (IC50 = 18.12 ± 0.15; 19.19 ± 0.72). The kinetic investigations have demonstrated that the compounds exhibit competitive‐type inhibition for α‐amylase, noncompetitive‐type inhibition for α‐glucosidase and AChE, and mixed‐type inhibition for BChE. Additionally, a molecular docking study was performed on all synthetic oxadiazoles to explore the interaction details of these compounds with the active sites of the enzymes.

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“…A549 cells were cultured and treated with similar methods to that in the published article. 61 A549 cells were purchased from the Korean Cell Line Bank (Seoul, Korea). The cells were incubated at 37 °C under 5% CO 2 in DMEM (Sigma, St. Louis, MO, USA), supplemented with 10% fetal bovine serum (FBS, WELGENE, Korea) and penicillin (Sigma, 50 units per mL) and streptomycin (Sigma, 50 μg mL −1 ).…”

Section: Methodsmentioning

confidence: 99%

“…Carbonic anhydrase inhibition was measured as described previously. [59][60][61] The technique is based on the precept that p-nitrophenyl acetate is hydrolyzed through carbonic anhydrase to form yellow-colored pnitrophenol, which was measured spectrophotometrically. In short, the reaction mixture contained 120 mL of 50 mM trissulfate buffer (pH 7.6 containing 0.1 mM ZnCl 2 ), 20 mL of inhibitor, and 20 mL of (50 U) bovine enzyme according to the size of the well.…”

Section: Biological Evaluationmentioning

confidence: 99%

Design, synthesis, and in vitro and in silico studies of 1,3,4-thiadiazole-thiazolidinone hybrids as carbonic anhydrase inhibitors

et al. 2023

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Synthesis, carbonic anhydrase inhibition, anticancer activity, and molecular docking studies of 1,3,4-oxadiazole derivatives

Cited by 10 publications

References 53 publications

Imidazole‐hydrazone derivatives: Synthesis, characterization, X‐ray structures and evaluation of anticancer and carbonic anhydrase I–II inhibition properties

Imidazole‐hydrazone derivatives: Synthesis, characterization, X‐ray structures and evaluation of anticancer and carbonic anhydrase I–II inhibition properties

Multitargeted inhibition of key enzymes associated with diabetes and Alzheimer's disease by 1,3,4‐oxadiazole derivatives: Synthesis, in vitro screening, and computational studies

Design, synthesis, and in vitro and in silico studies of 1,3,4-thiadiazole-thiazolidinone hybrids as carbonic anhydrase inhibitors

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