Syntheses, Antibacterial, Cytotoxic and Antifungal Effects of New 3-Carboxy-1-phenacylpyridinium Salts

Abstract

Thirteen pyridine-3-carboxylic acid salt derivatives with various substituted phenacyl residues were prepared and their cytotoxicity, antibacterial and antifungal activities tested. Compounds 5 and 11 proved to be active in the brine shrimp bioassay, compounds 7, 9-12 and 14 showed promising antibacterial activities, whereas none of the compounds tested against 15 fungal cultures proved to be active. Extensive spectroscopic techniques were employed to confirm the structure of the synthetic products.

Synthesis and Biological Evaluation of Isomeric Derivatives of Naturally Occurring Spatozoate

“…IR spectra (KBr discs) were recorded with a JASCO (Tokyo, Japan) spectrometer and electron impact mass spectra (EIMS) were determined with a Finnigan MAT-312 (Bremen, Germany), Varian MAT-112 (Bremen, Germany) double focusing mass spectromeeter connected to a PDP 11/34 (DEC) computer system; the data are tabulated as m/z and 3-nitrobenzyl alcohol was used as matrix. 1 H NMR and 13 C NMR spectra were performed in CDCl 3 , d 4 -MeOH and d 6 -acetone containing ca. 1 % tetramethylsilane as an internal standard with a Bruker (Rheinstetten-Forchheim, Germany) AM 300 and AM 400 spectrometer, respectively.…”

“…Colourless oil (95 mg, 58 %);13 C-NMR (63 MHz, CDCl 3 ): δ 167.0, 167.0, 140.5, 137.8, 132.2, 132.0, 131.7, 130.9, 130.6, 129.5, 129.3, 128.4, 127.8, 125.7, 65.1, 64.9, 30.7, 21.7, 19.3, 13.7 [10]; MS (EI, 70 eV): m/z ( %) = 327 (M + +1, 12), 309 (3), 253 (8), 207 (17), 191 (23), 165 (23), 154 (43), 135 (72), 119 (100), 77 (19), 55 (13), 43 (51). , 166.2, 143.7, 137.9, 132.2, 130.8, 129.7, 129.7, 129.3, 129.3, 129.1, 128.1, 127.7, 127.4, 65.1, 64.9, 30.7, 21.6, 19.3, 13.Hz, 3H, 5''-H); 13 C NMR (63 MHz, CDCl 3 ): δ 166.9, 165.4, 137.4, 132.3, 131.8, 131.8, 131.2, 130.9, 139.0, 129.3, 129.0, 128.3, 128.2, 127.9, 65.4, 65.1, 30.7, 19.3, 13.7[10]; MS (EI, 70 eV): m/z ( %) = 392 (M + +1, 78), 319(16), 207 (100), 191(19), 185 (53), 157(21), 133 (62), 104 (24), 89 (9), 75(18), 43(15).…”