Multicomponent synthesis and antimicrobial activity of alkyl 4-arylamino-1,2,6-triaryl-1,2,5,6-tetrahydropyridine-3-carboxylates

Abstract

Reaction of arylamines with aromatic aldehydes and β-ketoesters in the presence of bismuth nitrate or crystalline iodine as a catalyst afforded to alkyl 4-arylamino-1,2,6-triaryl-1,2,5,6-tetrahydropyridine-3carboxy-lates. Antimicrobial activity of the obtained compounds was studied.The IR spectra of compounds Ia-Iy contained absorption bands of stretching vibrations of amino group (3220-3280 cm -1 ) and ester carbonyl moiety in the position 3 (1644-1670 cm -1 ). In the 1 H NMR spectra of compounds Ia-Iy there were the signals of aromatic ring (6.06-7.88 ppm), methylene group in the position 5 as AB system (2.42-2.97, 2.61-3.38 ppm, J 15.6 Hz ), the protons H 6 (4.93-6.12 ppm) and H 2 (5.50-6.40 ppm) as well as of NH group (9.89-10.69 ppm). Mass spectrum ofIa contained the molecular ion peak [M] + with m/z 460 and the fragment ion peaks with m/z 383 [M -Ph] + , 368 [M -PhNH] + , 180 [PhNCH 2 Ph] + , 77 [Ph] + that confirmed the suggested structure. Mass spectra of other compounds Ib-Iy were similar.The assumed mechanism of this reaction is analogous to that described previously in the literature [2,10,12,13,17]. The aromatic amine reacts with βketoester and an aromatic aldehyde in the presence of a catalyst to form enamine A and imine B, respectively.

Tetrahydropyridine: a promising heterocycle for pharmacologically active molecules

“…THP derivatives were also converted into pyridine derivatives that exhibited relatively higher activity. 33 Another multicomponent reaction of aromatic aldehydes, arylamines, and β -ketoester in the presence of bismuth nitrate was carried out by Yankin et al 34 It resulted in the formation of alkyl 4-arylamino-1,2,6-triaryl-1,2,5,6-THPs-3-carboxylates. Compounds 12, 13, 14, and 15 were found to be weakly active antibacterial agents (MIC = 250 µ g/mL against E. coli and S. aureus) as compared to standard antibiotics.…”

“…Compounds 12, 13, 14, and 15 were found to be weakly active antibacterial agents (MIC = 250 µ g/mL against E. coli and S. aureus) as compared to standard antibiotics. 34 Srivastava et al 35 as well as resistant strains of bacteria. Compound 17 was also found to be potent (MIC = 0.12 µ g/mL against different strains of bacteria) and its activity was comparable to that of ciprofloxacin, gatifloxacin, and sparfloxacin.…”

“…Compounds 12, 13, 14, and 15 were found to be weakly active antibacterial agents (MIC = 250 µ g/mL against E. coli and S. aureus) as compared to standard antibiotics. 34 Srivastava et al 35 synthesized another series of 4,5,6,7-tetrahydrothieno [3,2-c]pyridine linked fluoroquinolones, in which the nitrogen of 4,5,6,7-tetrahydrothieno [3,2-c]pyridines was attached to fluoroquinolones at position #7. Among the newly synthesized compounds, 16 (Figure 2) exhibited significant antibacterial activity (MIC = 0.12 µ g/mL against Bacillus subtilis, S. aureus, and S. epidermidis) against susceptible as well as resistant strains of bacteria.…”

A Facile One‐Pot Solvent‐Free Synthesis, in Vitro and in Silico Studies of a Series of Tetrahydropyridine Derivatives as Breast Cancer Inhibitors

“…This catalyst efficiently accelerates inter‐ and intramolecular Mannich reactions to form the THP derivatives at room temperature within 2–3 h with good to excellent yields (Scheme 1). Furthermore, the reaction is metal‐free, solvent‐free and ATA is non‐corrosive, readily available, low cost, versatile, and promotes the efficient synthesis of acid‐catalyzed organic reactions [49–50] …”

A Nonlinear Optically Active Bismuth–Camphorate Coordination Polymer

“…Bismuth‐based CPs remain poorly explored, but become increasingly popular in a form of homoleptically enclosed metal centers due to their sufficiently broad range of potential applications. Therefore, some discrete complexes and CPs have been reported as potential bioactive (biocidic, antidiarrheal and antacid), or bioneutral compounds, gas sorption, luminescent and catalytic materials. In the absence of d‐ or f‐block electrons, Bi III ‐based compounds are transparent in the visible region of the electromagnetic spectrum, whose is highly desirable for its use as stable laser beam modulators, Q‐switches and mode‐lockers with the most spectrometers and devices equipped with laser source.…”