Synthesis and antiproliferative activity in vitro of new 2-aminobenzimidazole derivatives. Reaction of 2-arylideneaminobenzimidazole with selected nitriles containing active methylene group

Abstract

A series of pyrimido[1,2-a]benzimidazole and α-cyanocinnamic acid derivatives have been synthesized in the reactions of Schiff bases 2–7 with selected nitriles containing an active methylene group: malononitrile 8–12, cyanoacetamide 13–16, benzyl cyanide 17–21, benzoylacetonitrile 22–24, cyanoacetate methyl ester 25–28 and benzylacetamide 29. The structures 8–29 were confirmed by the results of elementary analysis and their IR, 1H-, 13C-NMR and MS spectra. The products 8–29 of various chemical structure pyrimido[1,2-a] benzimidazole 8–12, 14–16, 17–21, 23–24, 26 and α-cyanocinnamic acid derivatives 13, 22, 25, 27, 28 were obtained, which are of interest for biological studies or which can be substrates for further synthesis. The selected compounds 10, 13, 14, 17, 19, 21, 23–25 and 28 were screened for their antiproliferative activity in vitro against neoplastic and normal cell lines. The most active two compounds were: 2-(o-bromophenylene)-3-cyano-4-phenyl-1,2-dihydropyrimido[1,2-a]benzimidazole (24) and 3-cyano-4-phenyl-2-(2,4-dimethoxyphenyl)-1,2-dihydropyrimido[1,2-a]benzimidazole (23). However, similarly like cisplatin used as the control, they showed no selectivity towards cancer cells, by inhibiting proliferation of normal mouse fibroblasts in similar manner.

Synthesis and styrene copolymerization of novel dimethyl and dimethoxy ring-substituted isobutyl phenylcyanoacrylates

“…The molecular weights of the polymers was determined relative to polystyrene standards in THF solutions with sample concentrations 0.8% (w/v) by gel permeation chromatography (GPC) using a Altech 426 HPLC pump at an elution rate of 1.0 mL/min; Phenogel 5μ Linear column at 25ºC and Viscotek 302 RI detector. 1 H and 13 C NMR spectra were obtained on 10-25% (w/v) IPCA or polymer solutions in CDCl 3 at ambient temperature using Avance 300 MHz spectrometer. CHN-elemental analyses of IPCA compounds and nitrogen analysis of the copolymers were performed by Midwest Microlab, LLC (IN).…”

Synthesis and styrene copolymerization of novel fluoro, methyl, and phenoxy ring-disubstituted isobutyl phenylcyanoacrylates

“…The molecular weights of the polymers was determined relative to polystyrene standards in THF solutions with sample concentrations 0.8% (w/v) by gel permeation chromatography (GPC) using a Altech 426 HPLC pump at an elution rate of 1.0 mL/min; Phenogel 5μ Linear column at 25ºC and Viscotek 302 RI detector. 1 H and 13 C NMR spectra were obtained on 10-25% (w/v) IPCA or polymer solutions in CDCl3 at ambient temperature using Avance 300 MHz spectrometer. CHN-elemental analyses of IPCA compounds and nitrogen analysis of the copolymers were performed by Midwest Microlab, LLC (IN).…”

Synthesis and styrene copolymerization of novel trisubstituted ethylenes: 4. Halogen ring-substituted octyl phenylcyanoacrylates

“…Cyanoacrylates is family of vinyl monomers renowned for their high reactivity, instant adhesive properties, and wide-ranging applications [1][2][3]. Trisubstituted ethylenes (TSE), ring-functionalized (R 1 ) alkyl (R 2 ) phenylcyanoacrylates, R 1 PhCH = C(CN)CO2R 2 (PCA) continue to attract attention as compounds with variety of applications [4][5][6][7][8][9][10][11][12][13][14]. Thus, methoxy ring-substituted methyl phenylcyanoacrylate, MPCA was used in synthesis of pyridotriazines and triazolopyridines [4].…”