425704-32-1Relevant articles and documents
Iminonitroso diels-alder reactions for efficient derivatization and functionalization of complex diene-containing natural products
Li, Fangzheng,Yang, Baiyuan,Miller, Marvin J.,Zajicek, Jaroslav,Noll, Bruce C.,Moellmann, Ute,Dahse, Hans-Martin,Miller, Patricia A.
, p. 2923 - 2926 (2007)
A remarkably efficient method for derivatization of complex diene-containing natural products by using stabilized iminonitroso Diels-Alder reactions is described. Turimycin H3, ergosterol, reductiomycin, isoforocidin, colchicine and thebaine were found to react with nitrosopyridines in a highly efficient regio- and stereoselective fashion. Preliminary bioactivity evaluations of turimycin cycloadducts are reported.
Preparation and biological evaluation of novel leucomycin analogs derived from nitroso Diels-Alder reactions
Yang, Baiyuan,Zoellner, Tina,Gebhardt, Peter,Moellmann, Ute,Miller, Marvin J.
, p. 691 - 697 (2010)
A series of 10,13-disubstituted 16-membered macrolides was synthesized using nitroso Diels-Alder reactions of leucomycin A7. Despite the extensive constituent functionalities in leucomycin, the hetero cycloaddition reactions proceeded in a highly regio- and stereoselective fashion. Subsequent chemical modifications of the nitroso cycloadducts, including N-O bond reduction, were also conducted. Most leucomycin derivatives retained antibiotic profiles similar to leucomycin A7, and, in contrast to leucomycin itself, several exhibited moderate antiproliferative and cytotoxic activity.
Identification of triazolopyridine derivatives as a new class of AhR agonists and evaluation of anti-psoriasis effect in a mouse model
Chen, Nanjun,Li, Linli,Tian, Chenyu,Xia, Ziyi,Yang, Shengyong,Zhang, Guo
, (2022/02/05)
The aryl hydrocarbon receptor (AhR), a ligand-dependent transcription factor, can regulate the immune balance of Th17/22 and Treg cells, which plays an important role in the development and maintenance of the skin barrier. We herein report the discovery of triazolopyridine derivatives as a new class of AhR agonists. Structure-activity relationship analyses led to the identification of the most active compound, 6-bromo-2-(4-bromophenyl)-[1,2,4]triazolo[1,5-a]pyridine (12a), with an EC50 (50% effective concentration) value of 0.03 nM. Compound 12a could induce rapid nuclear enrichment of AhR, trigger the transcription of downstream genes and promote skin barrier repair. Topical or oral administration of 12a could significantly alleviate imiquimod (IMQ)-induced psoriasis-like skin lesion. Considering the excellent in vivo anti-psoriasis activity as well as good pharmacokinetic properties, 12a could be a promising lead compound for drug discovery against psoriasis, and deserving further investigation.
Syntheses and biological activity studies of novel sterol analogs from nitroso diels-alder reactions of ergosterol
Yang, Baiyuan,Miller, Patricia A.,Moellmann, Ute,Miller, Marvin J.
scheme or table, p. 2828 - 2831 (2009/12/06)
A serles of novel sterol analogs was prepared using nitroso Dlels-Alder reactions with ergosterol. Most cycloaddltlon reactions proceeded In an excellent reglo- and stereoselective fashion. Further N-O bond cleavage of cycloadducts generated compounds with biological activity In PC-3 and MCF-7 cancer cell lines
BICYCLIC TRIAZOLONE DERIVATIVES AND HERBICIDES CONTAINING THE SAME
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, (2008/06/13)
The present invention provides a bicyclic triazolone derivative represented by the formula:J-Ar [wherein, J is and Ar is ], which has excellent selective weeding activity and weed killer containing the said bicyclic triazolone derivative.