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The effect of a thieno[2,3-b]pyridine PLC-γ inhibitor on the proliferation, morphology, migration and cell cycle of breast cancer cells

“…Thieno[2,3-b]pyridine 1 was prepared from 1,3-cyclohexanedione 2 using a modied literature method shown in Scheme 1. 24 First, dione 2 was condensed with dimethylformamide dimethyl acetal (DMFDMA) to give enamine 3 (ref. 25) which was reacted immediately with cyanothioacetamide to give thiohexahydroquinoline 4 in 82% yield.…”

Some reactions of 3-cyano-4-(p-methoxyphenyl)-5-oxo-5,6,7,8-tetrahydro-quinoline-2(1H)-thione; Synthesis of new tetrahydroquinolines and tetrahydrothieno[2,3-b]quinolines

“…The interaction of 3 with two molar amount of phenyl isothiocyanate in hot pyridine gave the dithiouredo derivative 5 (Scheme 2). revealed that only few 3-cyano-5-oxo-5,6,7,8-tetrahydroquinoline-2(1H)thiones have been prepared by using 1,3cyclohexanedione or dimedone [8]. Encouraged by the above finding, we reported herein the synthesis of 3-cyano-4-(p-methoxyphenyl)-5-oxo-5,6,7,8tetrahydroquinoline-2(1H)-thione and its reactions with different reagents to obtain other tetrahydroquinolines as well as tetrahydro-thieno [2,3-b]quinolines with anticipated biological and medicinal importance.…”

Multicomponent Reactions of Carbonyl Compounds and Derivatives of Cyanoacetic Acid: Synthesis of Carbo- and Heterocycles

“…A different four-component reaction of benzaldehyde, malononitrile, the dimer of malononitrile, and piperidine or morpholine was used to prepare substituted 1,6-naphthyridines 229 (Scheme 63) 174. Thienobipyridines 231 were prepared by several different multicomponent reactions (Scheme 64): tetrahydropyridines 230, malononitrile, and acetone (Method A); Michael adducts 232, malononitrile, and acetone (Method B); aldehydes, Meldrum's acid (213), cyanothioacetamide, malononitrile, and acetone (Method C); and tetrahydropyridines 230, unsaturated nitrile 233, and acetone (Method D) 175,176. In reviewing the available information on the multicomponent reactions of cyanoacetic acid derivatives with car-bonyl compounds, it is important to recognize that the applications of such reactions are far from being exhausted.…”