1999
DOI: 10.1021/jm980707k
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Potent Inhibition of Influenza Sialidase by a Benzoic Acid Containing a 2-Pyrrolidinone Substituent

Abstract: On the basis of the lead compound 4-(N-acetylamino)-3-guanidinobenzoic acid (BANA 113), which inhibits influenza A sialidase with a Ki of 2.5 microM, several novel aromatic inhibitors of influenza sialidases were designed. In this study the N-acetyl group of BANA 113 was replaced with a 2-pyrrolidinone ring, which was designed in part to offer opportunities for introduction of spatially directed side chains that could potentially interact with the 4-, 5-, and/or 6-subsites of sialidase. While the parent struct… Show more

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Cited by 62 publications
(42 citation statements)
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“…For the synthesis of these new derivatives (compounds 34-40, Figure 3), different approaches have been used. The reported one-pot synthesis of 4-(2-oxopyrrolydin-1-yl)benzoic acid (36), starting from 4-aminobenzoic acid and ethyl 4-bromobutyrate, [16] suffers from low yields and was not suitable for preparing the corresponding 2-and 3-carboxy derivatives. Some of them (35, 36 and 37) were obtained by the Goldberg arylation starting from the corresponding 2-or 3-iodo carboxylic acids (or methylesters), but the yields were quite low (less than 60 %).…”
Section: Resultsmentioning
confidence: 99%
“…For the synthesis of these new derivatives (compounds 34-40, Figure 3), different approaches have been used. The reported one-pot synthesis of 4-(2-oxopyrrolydin-1-yl)benzoic acid (36), starting from 4-aminobenzoic acid and ethyl 4-bromobutyrate, [16] suffers from low yields and was not suitable for preparing the corresponding 2-and 3-carboxy derivatives. Some of them (35, 36 and 37) were obtained by the Goldberg arylation starting from the corresponding 2-or 3-iodo carboxylic acids (or methylesters), but the yields were quite low (less than 60 %).…”
Section: Resultsmentioning
confidence: 99%
“…In total, 126 known NIs were prepared in this study, and their bioactivities against influenza A virus were mainly taken from the literature [12,16,[22][23][24][25][26] ( Table 1). IC 50 values are available for most inhibitors except for a series of pyrrolidine NIs [12], for which IC 50 values were calculated from K i values using the Cheng-Prusoff equation [27].…”
Section: Methodsmentioning
confidence: 99%
“…(1) for the ring numbering system). Based on these ideas, diverse compounds have been synthesized and tested, and using the classification system of Varma and Hansch [50], the results are shown in Tables 2-10 [51][52][53][54][55][56][57][58][59][60][61].…”
Section: Structure-based Anti-neuraminidase Designmentioning
confidence: 99%