58532-75-5Relevant articles and documents
Comparative conventional and microwave assisted synthesis of heterocyclic oxadiazole analogues having enzymatic inhibition potential
Javid, Jamila,Aziz-ur-Rehman,Abbasi, Muhammad A.,Siddiqui, Sabahat Z.,Iqbal, Javed,Virk, Naeem A.,Rasool, Shahid,Ali, Hira A.,Ashraf, Muhammad,Shahid, Wardah,Hussain, Safdar,Ali Shah, Syed A.
, p. 93 - 110 (2020/10/06)
A comparative microwave assisted and conventional synthetic strategies were applied to synthesize heterocyclic 1,3,4-oxadiazole analogues as active anti-enzymatic agents. Green synthesis of compound 1 was achieved by stirring 4-methoxybenzenesulfonyl chloride (a) and ethyl piperidine-4-carboxylate (b). Compound 1 was converted into respective hydrazide (2) by hydrazine and then into 1,3,4-oxadiazole (3) by CS2 on reflux. The electrophiles, N-alkyl/aralkyl/aryl-2-bromopropanamides (6a–p) were synthesized and converted to N-alkyl/aralkyl/aryl-2-propanamide derivatives (7a–p) by reaction with 3 under green chemistry. Microwave assisted method was found to be effective relative to conventional method. 13C-NMR, 1H-NMR and IR techniques were availed to corroborate structures of synthesized compounds and then subjected to screening against lipoxygenase (LOX), α-glucosidase, acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes. A number of compounds presented better potential against these enzymes. The most active compounds against LOX and α-glucosidase enzymes were subjected to molecular docking study to explore their interactions with the active sites of the enzymes.
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.
, (2019/11/03)
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.
Copper-Catalyzed Cross-Coupling of Secondary α-Haloamides with Terminal Alkynes: Access to Diverse 2,3-Allenamides
Lv, Yunhe,Pu, Weiya,Zhu, Xueli,Zhao, Tiantian,Lin, Feifei
supporting information, p. 1397 - 1401 (2018/02/19)
A copper-catalyzed C(sp)?C(sp3) cross-coupling of terminal alkynes with readily available secondary α-haloamides for the efficient synthesis of 2,3-allenamides is realized. The methodology is characterized by its wide substrate scope, which makes it an important complement to traditional methods for synthesizing allenes. A mechanism involving an alkynylcopper species is proposed. (Figure presented.).
