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Titolo:
Synthesis and phosphodiesterase inhibitory activity of new sildenafil analogues containing a carboxylic acid group in the 5 '-sulfonamide moiety of aphenyl ring
Autore:
Kim, DK; Lee, JY; Lee, N; Ryu, DH; Kim, JS; Lee, S; Choi, JY; Ryu, JH; Kim, NH; Im, GJ; Choi, WS; Kim, TK;
Indirizzi:
SK Chem, Life Sci Res Ctr, Suwon 440745, Kyungki Do, South Korea SK Chem Suwon Kyungki Do South Korea 440745 0745, Kyungki Do, South Korea
Titolo Testata:
BIOORGANIC & MEDICINAL CHEMISTRY
fascicolo: 11, volume: 9, anno: 2001,
pagine: 3013 - 3021
SICI:
0968-0896(200111)9:11<3013:SAPIAO>2.0.ZU;2-H
Fonte:
ISI
Lingua:
ENG
Soggetto:
ERECTILE DYSFUNCTION; NUCLEOTIDE PHOSPHODIESTERASE; IMPOTENCE;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Citazioni:
22
Recensione:
Indirizzi per estratti:
Indirizzo: Kim, DK SK Chem, Life Sci Res Ctr, 600 Jungja Dong, Suwon 440745, Kyungki Do, South Korea SK Chem 600 Jungja Dong Suwon Kyungki Do South Korea 440745 Korea
Citazione:
D.K. Kim et al., "Synthesis and phosphodiesterase inhibitory activity of new sildenafil analogues containing a carboxylic acid group in the 5 '-sulfonamide moiety of aphenyl ring", BIO MED CH, 9(11), 2001, pp. 3013-3021

Abstract

New sildenafil analogues possessing a carboxylic acid group in the 5'-sulfonamide of the phenyl ring, 9a-I, were prepared from the readily available starting compounds 6a-b and cyclic amines 3-5 in a three-step sequence. In the enzyme assays, it has been shown that all the target compounds 9a-I proved to be more potent in inhibiting phosphodiesterase type 5 (PDE5) than sildenafil by 4-38-fold. The effects on the IC50 values were investigated by varying the alkoxy group (R) of the phenyl ring, the sulfonamide type (X), and the length of the methylene chain linking the carboxylic acid, and the results were discussed in detail. From this study, we have clearly demonstrated that introduction of a carboxylic acid group to the 5'-sulfonamide moiety of the phenyl ring greatly enhanced PDE5 inhibitory activity, probably by mimicking the phosphate group of cGMP. The piperidinyl propionic acid derivative 9i, which showed the highest PDE5 inhibitory activity and comparable to better selectivity over PDE isozymes in comparison with sildenafil, has been selected for more detailed biological investigations. (C) 2001 Elsevier Science Ltd. All rights reserved.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 06/04/20 alle ore 20:14:06