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Design and Synthesis of Human Immunodeficiency Virus Entry Inhibitors: Sulfonamide as an Isostere for the α-Ketoamide Groupстатья
Статья опубликована в высокорейтинговом журнале
Информация о цитировании статьи получена из
Web of Science,
Scopus
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 16 декабря 2014 г.
- Авторы: Lu R.J., Tucker J.A., Zinevitch T.V., Kirichenko O., Konoplev Vitalii, Kuznetsova Svetlana, Sviridov Sergey, Pickens Jason, Tandel Sagun, Brahmachary Enugurthi, Yang Yang
- Журнал: Journal of Medicinal Chemistry
- Том: 50
- Номер: 26
- Год издания: 2007
- Издательство: American Chemical Society
- Местоположение издательства: United States
- Первая страница: 6535
- Последняя страница: 6544
- Аннотация: The crystal structures of many tertiary R-ketoamides reveal an orthogonal arrangement of the two carbonyl groups. Based on the hypothesis that the R-ketoamide HIV attachment inhibitor BMS 806 (formally BMS378806, 26) might bind to its gp120 target via a similar conformation, we designed and synthesized a series of analogs in which the ketoamide group is replaced by an isosteric sulfonamide group. The most potent of these analogs, 14i, demonstrated antiviral potency comparable to 26 in the M33 pseudotyped antiviral assay. Flexible overlay calculations of a ketoamide inhibitor with a sulfonamide inhibitor revealed a single conformation of each that gave significantly better overlap of key pharmacophore features than other conformations and thus suggest a possible binding conformation for each class.
- Добавил в систему: Зиневич Татьяна Витальевна