New series of triazole derivatives coupled with amino acids 1a‐h were obtained via multicomponent reaction of 2‐hydroxy benzaldehyde or 2‐hydroxy acetophenone with thiosemicarbazide and different amino acids. The obtained compounds were reacted with p‐toluinesulfonyl chloride 2 to give the corresponding sulfonamides 3a‐h. Compound 1b was allowed to react with different aromatic aldehydes or cyclic ketone under alkaline conditions to afford the expected imino compounds 4a‐d and 6a‐c, respectively. These compounds were allowed to react with ethyl glycolate to yield the expected thiazolidinone derivatives 5a‐d or 7a‐c, respectively. Structures of the newly synthesized compounds were found to be in accordance with their elemental analyses and spectral data. The obtained compounds exhibited very prominent in vitro and in vivo antihyperglycemic effect at a dose of 40 mg/kg body weight compared to the standard drug gliclazide and control. The antidiabetic effect was investigated using oral glucose tolerance test in normal and non‐insulin‐dependent diabetes mellitus (NIDDM) in STZ‐rat model. Compounds 3a‐h, 5b, 5c, 5d, 7a, 7b, and 7c showed significant activity in lowering blood glucose (more than 80%) compared to the NIDDM control.
All melting points were determined on a Koffler melting point apparatus and are uncorrected. 1 H-NMR and 13 C NMR spectra were recorded on a Bruker avance 400 MHz spectrometer using TMS as internal reference (chemical shifts in , ppm), and IR spectra were obtained on a Nicolet 710 FT-IR spectrometer (KBr, max in cm -1 ). Mass spectra were recorded on a GC-MSQP 1000EX Schimadzu at the Microanalytical laboratory, Cairo University, Cairo, Egypt. Elemental analyses were recorded on Vario El Fab-Nr elemental analyzer (Cairo University).
S2. Experimental Procedures
General procedure for preparation of ionic liquid Piperidinium acetate-IL:Piperidine (0.9 mL, 0.1 mol) was cooled in an ice bath with continuous stirring then was treated with acetic acid (0.6 g, 0.1 mol) drop-wise through a separating funnel.After reaction completion water vapor was removed under reduced pressure using rotatory evaporator then the product was stored in a vacuum desicator. White solid (13.5
A new series of [1,2,4]-triazole bearing amino acid derivatives were synthesized under green chemistry conditions and evaluated for their antimicrobial activities.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.