109098-43-3Relevant articles and documents
A novel five-step synthetic route to 1,3,4-oxadiazole derivatives with potent α-glucosidase inhibitory potential and their in silico studies
Iftikhar, Muhammad,Shahnawaz,Saleem, Muhammad,Riaz, Naheed,Aziz-ur-Rehman,Ahmed, Ishtiaq,Rahman, Jameel,Ashraf, Muhammad,Sharif, Muhammad S.,Khan, Shafi U.,Htar, Thet T.
, (2019)
A series of new N-aryl/aralkyl derivatives of 2-methyl-2-{5-(4-chlorophenyl)-1,3,4-oxadiazole-2ylthiol}acetamide were synthesized by successive conversions of 4-chlorobenzoic acid (a) into ethyl 4-chlorobenzoate (1), 4-chlorobenzoylhydrazide (2) and 5-(4-chlorophenyl)-1,3,4-oxadiazole-2-thiol (3), respectively. The required array of compounds (6a–n) was obtained by the reaction of 1,3,4-oxadiazole (3) with various electrophiles (5a–n) in the presence of DMF (N,N-dimethylformamide) and sodium hydroxide at room temperature. The structural determination of these compounds was done by infrared, 1H-NMR (nuclear magnetic resonance), 13C-NMR, electron ionization mass spectrometry, and high-resolution electron ionization mass spectrometry analyses. All compounds were evaluated for their α-glucosidase inhibitory potential. Compounds 6a, 6c–e, 6g, and 6i were found to be promising inhibitors of α-glucosidase with IC50 values of 81.72 ± 1.18, 52.73 ± 1.16, 62.62 ± 1.15, 56.34 ± 1.17, 86.35 ± 1.17, 52.63 ± 1.16 μM, respectively. Molecular modeling and ADME (absorption, distribution, metabolism, excretion) predictions supported the findings. The current synthesized library of compounds was achieved by utilizing very common raw materials in such a way that the synthesized compounds may prove to be promising drug leads.
Microwave-assisted synthesis of triazole derivatives conjugated with piperidine as new anti-enzymatic agents
Abbasi, Muhammad A.,Ali Shah, Syed A.,Htar, Thet T.,Iqbal, Javed,Khalid, Hira,Khan, Shafi U.,Laulloo, Sabina J.,Rasool, Shahid,Rehman, Aziz-ur-,Siddiqui, Sabahat Z.,Virk, Naeem A.
, (2020/01/25)
The current study was aimed for the study of piperidine-based triazole compounds for their biological potential against various enzymes. A novel library of compounds, 9a-r, having piperidine, 1,2,4-triazole, and propanamides was synthesized through consecutive steps including the formation of sulfonamide, hydrazide, 1,2,4-triazole, and thio-ether. Initially, 4-methoxybenzenesulfonyl chloride (1) and ethyl isonipecotate (2) were utilized to develop ethyl 1-(4-methoxyphenylsulfonyl)-4-piperidinecarboxylate (3). The product 3 was converted into respective hydrazide (4) which was further cyclized into 1,2,4-triazole (5) nucleus. A series of propanamides, 8a-r, were synthesized from different amines, 6a-r. These electrophiles, 8a-r, were reacted with compound 5 under conventional and microwave-assisted protocols to acquire the library of hybrids, 9a-r. The structural confirmations were availed by 1H-NMR, 13C-NMR, and IR techniques. The whole series was evaluated for biological potential against acetylcholinesterase (AChE) and α-glucosidase enzymes. The biological evaluation ranges low to high in potential for different compounds based on the structural variations of synthesized compounds. Almost all the compounds remained active against both the enzymes except a few ones. The bovine serum albumin (BSA) binding study demonstrated the flow of drug in the body, and the docking study explained the interactions responsible for active behavior of synthesized compounds.
