1994
DOI: 10.1021/jm00043a020
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Triazolinone Biphenylsulfonamide Derivatives as Orally Active Angiotensin II Antagonists with Potent AT1 Receptor Affinity and Enhanced AT2 Affinity

Abstract: Several series of 2,4-dihydro-2,4,5-trisubstituted-3H-1,2,4-triazol-3-ones with acidic sulfonamide replacements of tetrazole at the 2'-position of the biphenyl-4-ylmethyl side chain at N4 were prepared and tested as angiotensin II (AII) antagonists. Preferred substituents on the triazolinone ring were n-butyl at C5 and 2-(trifluoromethyl)phenyl at N2. Subnanomolar IC50 values at the AT1 receptor subtype were observed for a variety of acylsulfonamides, including aroyl, heteroaroyl, and cycloalkylcarbonyl deriva… Show more

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Cited by 38 publications
(14 citation statements)
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“…1 (a). The configuration cost was 14.23, which is in agreement to standard requirement of configuration (Ashton et al, 1994) cost that should not exceed a maximum value of 17 (corresponds to a number of 2 17 pharmacophore models) because high values may lead to a chance correlation of the generated hypothesis. Thus, hypothesis 1 was considered as the best pharmacophore model for NMDA inhibitory activity and was used to predict the activity of all the 17 training set compounds.…”
Section: Pharmacophore Generationsupporting
confidence: 81%
“…1 (a). The configuration cost was 14.23, which is in agreement to standard requirement of configuration (Ashton et al, 1994) cost that should not exceed a maximum value of 17 (corresponds to a number of 2 17 pharmacophore models) because high values may lead to a chance correlation of the generated hypothesis. Thus, hypothesis 1 was considered as the best pharmacophore model for NMDA inhibitory activity and was used to predict the activity of all the 17 training set compounds.…”
Section: Pharmacophore Generationsupporting
confidence: 81%
“…Hypothesis1 had total cost close to fixed cost (124.52), lower error cost (103.409), lowest root-mean-square (RMS) divergence (0.408), best correlation ( r = 0.977), and good internal test set prediction ( r test-set = 0.93). The configuration cost of the hypothesis exceeded the limit of 17 bits but can be accepted as the model achieves other validation criterion [11,12]. …”
Section: Resultsmentioning
confidence: 99%
“…N -acylsulfonamide (sulfacetamide) is well known basic common structural motif [1], which is present as a functional group in a wide range of therapeutics [2]. The formation of N -acylsulfonamides (sulfacetamides) is synthetically important for easy access to various structures [3]. Molecules containing acylsulfonamide (sulfacetamide) functional groups have been explored as HCV protease inhibitors and CXCR 2 antagonists [4].…”
Section: Introductionmentioning
confidence: 99%