An efficient and simple synthesis of highly congested 2-benzyloxy-3-benzyloxymethyl-5-sec-aminobiphenyl-4-carbonitriles 3a–e has been delineated through base catalyzed ring transformation of 6-aryl-4-sec-amino-2H-pyran-2-one-3-carbonitriles 1 by 1,3-bisbenzyloxypropan-2-one 2. Debenzylation of both the O-benzyl groups of 3a–e with boron trichloride provided the corresponding diols, 2-hydroxy-3-hydroxymethyl -5-sec-aminobiphenyl-4-carbonitriles 4a–e in very good yields.

An innovative and efficient synthesis of highly congested 2-amino-3-aminomethyl-5-methylsulfanyl/sec-aminobiphenyl-4-carbonitriles 4 has been delineated through base catalyzed ring transformation of 6-aryl-4-methylsulfanyl/sec-amino-2H-pyran-2-one-3-carbonitriles 1 with Boc-protected 1,3-diamino-2-propanone 2, followed by TFA catalyzed hydrolysis of the intermediate [3-tert-butoxycarbonylaminomethyl-4-cyano-5-methylsulfanyl/sec-aminobiphenyl-2-yl]carbamic acid tert-butyl ester 3 in moderate yields as the TFA salts.

Five new structural analogues of substituted-1H-quinolinones (19, 20, 23, 24, and 26) have been synthesized and evaluated for Staphylococcus aureus methionyl-tRNA synthetase enzyme inhibitory activity. These compounds were also tested against pathogens of six S. aureus, two Enterococcus faecalis, and one Enterococcus faecium. Among all the synthesized quinolinones, compound 20 displayed significant inhibitory activities in the strains of E. faecalis and E. faecium.

The synthesis of various ferrocenylarenes (3, 5a, 6) and heteroarenes (5b, c, 7) frorn 6-ferrocenyl-4-methylsulfanyl-2H-pyran-2-one-3-carbonitrile 1 through nucleophile induced ring transfomation reactions has been delineated. (C) 2004 Published by Elsevier Ltd.

An expedient synthesis of 1,3-diaryl-4-(3,3′-diindolyl)methylpyrazoles 3a–m has been developed using Amberlyst 15 catalyzed condensation of 1,3-diaryl-4-formyl pyrazoles 2 with indoles 1. This reaction was further extended to the synthesis of 4,4′-bis(3,3′-diindolyl)methylphenoxy-alkanes 5a–b by coupling of 4,4′–di(formylphenoxy)alkane 4 with indole 1.

A series of (3-pyridin-2-yl-thiouriedo)alkanoic acid esters (5a–j) have been synthesized by the reaction of pyridin-2-yl-dithiocarbamic acid methyl ester (2) and amino acid esters (4). Most of the synthesized compounds have been evaluated against glucose-6-phosphatase enzyme but only four compounds (5g–j) displayed significant inhibitory activity of the enzyme.

Biaryls, 7-naphthyl-5-s-amino-2,3-dihydrobenzo[b]thiophene-4-carbonitriles (3a–e), 8-(1-naphthyl)-6-s-amino-isothiochroman-5-carbonitriles (6a–d), 4-(1-naphthyl)-2-s-aminobezocycloalkene-1-carbonitriles (6e–j), 8-naphthyl-6-s-amino-2-ethyl-1,2,3,4-tetrahydro-isoquinoline-5-carbonitrle (6k–n), 1-naphthyl-3-s-amino-10H-9-thia-phenantherene-4-carbonitriles (8a–e) and 1-(1-naphthyl)-3-s-amino-9,10-dihydrophenantherene-4-carbonitriles (8f–i) have been prepared through carbanion induced ring transformation reactions of 6-naphthyl-3-cyano-4-s-amino-2H-pyran-2-ones (1) from respective ketones (2, 5, and 7). These compounds have been evaluated for their glucose-6-phosphatase inhibitory activity and only 6a, c, j, m, c, d, h displayed significant inhibition of the glucose-6-phosphatase.

A series of 2-sec-amino-3H-quinazolin-4-ones (4a–p) and 4-sec-amino-2-chloroquinazolines (5a–b) have been synthesized by nucleophilic substitution reaction of 2-chloro-4(3H)-quinazolones (3) and 2,4-dichloroquinazolines (2) with amines, respectively. Most of the synthesized compounds were evaluated for antihyperglycemic activity but only 4a,b,d,j,o displayed significant reduction in blood glucose level in streptozotocin and sucrose loaded rat models.

A general and efficient synthesis of 8-aryl-5-methoxycarbonyl-6-methylsulfanyl-3,4-dihydro-2(1H)-naphthalenones 4a–i and 8-aryl-5-cyano-6-sec-amino-3,4-dihydro-2(1H)-naphthalenones 4l–r has been delineated from the acid hydrolysis of 8-aryl-5-methoxycarbonyl-6-methylsulfanyl-3,4-dihydro-2(1H)-naphthalenone-(2,2-dimethyltrimethylene)ketals 3a–i and 8-aryl-5-cyano-6-sec-amino-3,4-dihydro-2(1H)-naphthalenone-(2,2-dimethyltrimethylene) ketals 3l–r, obtained from the reaction of 6-aryl-3-methoxycarbonyl-4-methylsulfanyl-2H-pyran-2-ones 1a–i and 3-cyano-6-aryl-4-sec-amino-2H-pyran-2-ones 1l–r with 1,4-cyclohexanedione mono-(2,2-dimethyltrimethylene)ketal 2.