Pyridinyl analogues

Miesel (1976) obtained active analogues of diilubenzuron by repladng the /K hloroaniline moiety by substituted aminopyrazines. As an extension of their earlier work DeMilo et al. (1978) have synthesised and tested a series of new analogues where the aniline portion of the diilubenzuron molecule has been exchanged for various substituted heterocycles such as isoxazoles, thiazoles, thiadiazoles, pyridines, pyrimidines, 5-triazines and bicyclic heterocycles. The most active derivatives were the 4-bromo- (112) and 4-chloro-2-pyridinyl analogues (113) but none was as active as diilubenzuron. 

Pyridinyl analogues 145 were obtained using water as solvent and the resulting 1,4-dihydeopyridine were subsequently aromatized by ferric chloride or potassium permanganate in a one-pot synthesis. ... 

Copper(l) analogues [(L)Cu(MeCN)][CF3S03] (747) [yellow, four-coordinate (two amine donors, one of the two pyridinyl groups and an MeCN] and [(L)Cu(MeCN)][BF4] (748) [red, five-coordinate (two tertiary amine, two pyridinyl and an MeCN] [L as that in copper(II) complex (241)] were structurally characterized and redox properties of these complexes were also investigated.224... 

A series of novel 4-substituted-l,4-dihydroquinolines 140 were prepared and found to exhibit moderate to excellent mammalian topo II inhibitory activity. Among the compounds prepared, in general, the nitrogen analogues are the most active compounds and the sulfur analogue is the least active one. The most potent analogue 140 (X=NH-2-pyridinyl), had a topo II potency nearly equivalent to VP-16, a clinically useful topo II interactive antitumor agent, q. (55) [197]. 

The ESR hyperfine coupling constants have been established experimentally (67MI20402) for the pyridinyl radical (134 R = H) and deuterated analogues, produced by y irradiation of a solid solution of pyridine in ethanol at 77 K, but the signs of the couplings are not known experimentally and are made solely on the basis of Huckel MO calculations. INDO MO calculations on this radical, together with the radical anions of quinoline, isoquinoline and acridine h ve also been carried out (740MR(6)5). 

Syntheses, nicotinic acetylcholine receptor binding, and antinociceptive properties of 2-exo-2-(2 -Substituted 5-pyridinyl)-7-azabicyclo[2.2.1]heptanes. Epibatidine-analogues, J. Med. Chem. 

There has been considerable interest in the thienothiazine ring system from the pharmaceutical and pharmacological view point since 1976 when tenoxicam (4-hydroxy-2-methyl-7V-2-pyridinyl-2//-thieno[2,3-c]-l,2-thiazine-3-carboxamide-1,1-dioxide) (376) was patented by Hoffmann-La Roche as an antiinflammatory agent. Since then there have been hundreds of references to analogues, and to related compounds, and their pharmacological action, metabolism, and analytical methods for these compounds. It would be beyond the scope of this chapter to attempt to review these data. 

Eisai Co Ltd. (Japan) synthesized 4-alkoxyalkoxy-pyridine analogues of omeprazole and selected E-3810 [35], rabeprazole, as their candidate drug (Fig. 2.17). Rabeprazole, which has the 4-methoxypropoxy-3-methyl-pyridinyl moiety in its chemical structure, is largely similar to omeprazole (as are pantoprazole and lansoprazole) and has now also reached the market. 

The 4-substituted analogue of the current invention, (E)-4- 4-[2-(4-pyridinyl)-ethenyl]-phenoxy -butyric acid ethyl ester, (I), was also prepared by the author and is discussed. 

Concurrently with the studies in the aryl-cyclohexenyl systems, we undertook the study of amide functionality in the 4-position of the cyclohexyl ring. Benzamides such as sulpiride comprise a well-known class of DA antagonists. But when applied in a somewhat different context, benzamide functionality attached via the cyclohexyl tether to an aryl amine led to DA partial agonists. A series of analogues probed the importance of distance and stereochemistry between the pyridinyl piperazine and the benzamide functionalities and some analogues were found to have potent activity as DA autoreceptor agonists.77... 

Carroll, F.L. Liang, F. Navarro, H.A. Brieaddy, L.E. Abraham, R Damaj, M.I. Martin, B. R. Synthesis, nicotinic acetylcholine receptor binding, and antinociceptive properties of 2-cxo-2-(2 -substituted 5 -pyridinyl)-7-azabicyclo [2.2.1]heptanes. Epibatidine analogues. J. Med. Chem. 44(13),2229-2237. 

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