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Title: Synthesis, Characterization and Biological Evaluation of Bisphenol and Bisphenol Sulfide Derivatives
Authors: Ibrahim, Muhammad
Keywords: Physical Sciences
Organic Chemistry
Issue Date: 2021
Publisher: University of Malakand, Chakdara
Abstract: As per the proposed plan of work, attempts were made to synthesize different derivatives of bisphenol and bisphenol sulfide. Derivatives of bisphenol and bisphenol sulfide such as macrocycles (Scheme 1) and Schiff’s bases (Scheme 2 and 3) were successfully synthesized using standard procedures. The bisphenol sulfide was oxidized to the corresponding bisphenol sulfoxide and sulfone using different oxidizing agents like NaIO4, H2O2/AcOH and metachloroperbenzoic acid with reasonable yields. The synthesized compounds were purified through washing and crystallization where needed. The structures of all the compounds were determined with the help of different spectroscopic techniques such as ESI-MS/HR-MS and 1HNMR. Most of the compounds showed aromatic protons (ArH) peaks in 1H NMR spectra showing the chemical shift in δ 6-8.8 region, the alkyl protons appeared in the region δ 0.8-4.0, the methylene protons (- NCH2CO-) were appeared in the δ 4.0-5.5 region, the amide protons (-CO-NH-) in the region between δ 8-12 , the imine proton (-N=CH-) in the δ 8-9 region, and other substituents (OH, CH3, OCH3, N(CH2CH3) at the imine displaying varying chemical shift values. The ESI-MS/HRMS of the products displayed the molecular ion peaks [M]+ and various characteristics fragments of the compounds. All the synthesized compounds were screened for biological activities such as anticholinesterase and antioxidant. Among the target macrocycles, the most active included 207 with IC50 81.1 ± 0.54 µM, 209 with IC50 76.9 ± 0.24 µM and 213 with IC50 71.2 ± 0.77 µM in comparison to anticholinesterase activity of the standard drug galantamine with IC50 value of 69.7 ± 0.18 µM. Macrocycle 211 was found most potent against butyrylcholinesterase with IC50 value of 55.3 ± 0.54 µM when compared to galantamine that showed IC50 valued of 52.3 ± 0.53 µM. Similarly, compounds 228 and 230 having high inhibitory potential with IC50 of 66.6 ± 0.1 µM and 67.9 ± 0.4 µM against acetylcholinesterase as compared with the standard drug galantamine. Compound 230 also showed high potency against the butyrylcholinesterase with IC50 of 31.5 ± 0.2 µM as compared to standard drug galantamine with IC50 of 52.3 ± 0.53 µM. These hydrazones were also screened for their antioxidant potential. The most active among them was 220 with IC50 of 39.33 ± 0.99 µM as compared to gallic acid taken as positive control with IC50 of 36.0 ± 0.99 µM.
Gov't Doc #: 24842
Appears in Collections:PhD Thesis of All Public / Private Sector Universities / DAIs.

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