100306-70-5Relevant articles and documents
Some new methods for preparing 2,3- and 3,4-diaminopyridines
Campbell,Greene,Lavagnino,et al.
, p. 669 - 672 (1986)
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Structure-activity relationships in Toll-like receptor 7 agonistic 1H-imidazo[4,5-c]pyridines
Yoo, Euna,Crall, Breanna M.,Balakrishna, Rajalakshmi,Malladi, Subbalakshmi S.,Fox, Lauren M.,Hermanson, Alec R.,David, Sunil A.
, p. 6526 - 6545 (2013/09/24)
Engagement of TLR7 in plasmacytoid dendritic cells leads to the induction of IFN-α/β which plays essential functions in the control of adaptive immunity. We had previously examined structure-activity relationships (SAR) in TLR7/8-agonistic imidazoquinolines with a focus on substituents at the N 1, C2, N3 and N4 positions, and we now report SAR on 1H-imidazo[4,5-c]pyridines. 1-Benzyl-2-butyl-1H-imidazo[4,5-c] pyridin-4-amine was found to be a pure TLR7-agonist with negligible activity on TLR8. Increase in potency was observed in N6-substituted analogues, especially in those compounds with electron-rich substituents. Direct aryl-aryl connections at C6 abrogated activity, but TLR7 agonism was reinstated in 6-benzyl and 6-phenethyl analogues. Consistent with the pure TLR7-agonistic behavior, prominent IFN-α induction in human PBMCs was observed with minimal proinflammatory cytokine induction. A benzologue of imidazoquinoline was also synthesized which showed substantial improvements in potency over the parent imidazopyridine. Distinct differences in N6-substituted analogues were observed with respect to IFN-α induction in human PBMCs on the one hand, and CD69 upregulation in lymphocytic subsets, on the other.
Practical amination of nitropyridones by silylation
Singer, Robert A.,Dore, Michael
supporting information, p. 1261 - 1264 (2013/01/03)
A practical method for coupling nitropyridones (1) with primary amines by treatment with hexamethyldisilazane has been developed, avoiding the use of hazardous reagents such as POCl3. The activation of the pyridone by a nitro group is necessary for efficient coupling, leading to aminonitropyridines (3) in good yields. Regioisomers other than 3-nitro-4-pyridone (1) were found to be substantially less reactive but would undergo coupling with primary amines.