Aryl aminopyrazole amides capped with N-alkylbenzamides 13-16 are selective glucocorticoid receptor agonists. 2,6-Disubstituted benzamides have prednisolone-like potency or better in vitro. Good oral exposure was demonstrated in the rat, with compounds with lower lipophilicity, for example N-hydroxyethyl benzamides (e.g., 16e).
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http://dx.doi.org/10.1016/j.bmcl.2008.10.128 | DOI Listing |
Chem Commun (Camb)
January 2024
School of Pharmacy and Key Laboratory of Prevention and Treatment of Cardiovascular and Cerebrovascular Diseases of Ministry of Education, Gannan Medical University, Ganzhou, 341000, P. R. China.
An efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as a single coupling partner was demonstrated, in which fused benzodiazepine skeletons were obtained in excellent yields. This method greatly improved an effective approach to dual C-H unsymmetrical functionalization.
View Article and Find Full Text PDFOrg Lett
October 2023
State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China.
Herein, a highly enantioselective arylation reaction of 3-aryl-5-aminopyrazoles and quinone derivatives was realized using a chiral phosphoric acid catalyst under mild conditions. The reaction has a broad scope with respect to both arylation reaction partners and hence offers rapid access to an array of axially chiral arylpyrazoles with pretty outcomes (up to 95% yield and 99% ee). Notably, the reaction is very efficient, as the catalyst loadings for the model reaction can be reduced to 1 mol % and the enantioselectivity is still maintained.
View Article and Find Full Text PDFChemistry
April 2023
Key Laboratory of Chemistry in Ethnic Medicinal Resources, Key Laboratory of Natural Products Synthetic Biology of Ethnic Medicinal Endophytes, State Ethnic Affairs Commission & Ministry of Education, School of Ethnic Medicine, Yunnan Minzu University, Kunming, 650500, P. R. China.
A chiral phosphoric acid-catalyzed enantioselective aza-Friedel-Crafts reaction of 5-aminopyrazole derivatives with cyclic ketimines attached to a neutral functional group is reported. This protocol allows the formation of pyrazole-based C2-quaternary indolin-3-ones with high enantioselectivities and regioselectivities. Moreover, gram-scale synthesis of the 5-aminopyrazole-based C2-quaternary indolin-3-ones was performed, with no decrease in the yield and enantioselectivity.
View Article and Find Full Text PDFBiomed Pharmacother
December 2022
Key Laboratory of Plant Resources and Chemistry in Arid Regions, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, 40-1 South Beijing Rd, Urumqi 830011, PR China; University of Chinese Academy of Sciences, Yuquan Rd 19 A, Beijing 100049, PR China. Electronic address:
Novel pyrazolo[3,4-d] pyrimidine derivatives bearing carbon-aryl(heteryl)idene moieties were synthesized via a condensation reaction of 5-aminopyrazoles and cyclic lactams. The preparation of the target compounds employed bioisosterism, where a pyrazole ring was a major replacement. Fifteen target compounds were investigated for their antiproliferative activity on five human cancer cell lines; derivative (E)- 1-methyl-9-(3,4,5-trimethoxybenzylidene)- 6,7,8,9-tetrahydropyrazolo[3,4-d]pyrido[1,2-a]pyrimidin-4(1H)-one (10k) showed the highest activity (IC value (0.
View Article and Find Full Text PDFDrug Dev Res
February 2023
Chemistry Department, Faculty of Science (Boys), Al-Azhar University, Nasr City, Cairo, Egypt.
The strategy of utilizing nitrogen compounds in various biological applications has recently emerged as a powerful approach to exploring novel classes of therapeutics to face the challenge of diseases. A series of pyrazolo[1,5-a]pyrimidine-based compounds 3a-l and 5a-f were prepared by the direct cyclo-condensation reaction of 5-amino-1H-pyrazoles 1a, b with 2-(arylidene)malononitriles and 3-(dimethylamino)-1-aryl-prop-2-en-1-ones, respectively. The structures of the new pyrazolo[1,5-a]pyrimidine compounds were confirmed via spectroscopic techniques.
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