Imidazole derivatives. XIII. Synthesis and pharmacological activity of some 1,4,5-substituted 1H-imidazoles

Iradyan, M. A.; Torosyan, A. G.; Mirzoyan, R. G.; Badalyants, I. P.; Isaakyan, Z. S.; Manucharyan, D. Sh.; Dayan, M. Kh.; Sakanyan, G. S.; Dzhagatspanyan, I. A.; Akopyan, N. E.; Ter-Zakharyan, Yu. Z.; Aroyan, A. A.

doi:10.1007/bf01152240

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2008

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“…Chromatographic purification of the crude gave 25 as an off-white solid (1.03 g) in 75% yield. Mp = 110−112 °C (lit . mp = 112−113 °C).…”

Section: Methodsmentioning

confidence: 99%

Structure Based Development of Phenylimidazole-Derived Inhibitors of Indoleamine 2,3-Dioxygenase

et al. 2008

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Indoleamine 2,3-dioxygenase (IDO) is emerging as an important new therapeutic target for the treatment of cancer, chronic viral infections, and other diseases characterized by pathological immune suppression. With the goal of developing more potent IDO inhibitors, a systematic study of 4-phenyl-imidazole (4-PI) derivatives was undertaken. Computational docking experiments guided design and synthesis efforts with analogs of 4-PI. In particular, three interactions of 4-PI analogs with IDO were studied: the active site entrance, the interior of the active site and the heme iron binding. The three most potent inhibitors (1, 17 and 18) appear to exploit interactions with C129 and S167 in the interior of the active site. All three inhibitors are approximately ten-fold more potent than 4-PI. The study represents the first example of enzyme inhibitor development with the recently reported crystal structure of IDO and offers important lessons in the search for more potent inhibitors.

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“…Chromatographic purification of the crude gave 25 as an off-white solid (1.03 g) in 75% yield. Mp = 110−112 °C (lit . mp = 112−113 °C).…”

Section: Methodsmentioning

confidence: 99%

Structure Based Development of Phenylimidazole-Derived Inhibitors of Indoleamine 2,3-Dioxygenase

et al. 2008

View full text Add to dashboard Cite

show abstract

Imidazole derivatives. XIII. Synthesis and pharmacological activity of some 1,4,5-substituted 1H-imidazoles

Cited by 1 publication

References 3 publications

Structure Based Development of Phenylimidazole-Derived Inhibitors of Indoleamine 2,3-Dioxygenase

Structure Based Development of Phenylimidazole-Derived Inhibitors of Indoleamine 2,3-Dioxygenase

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