A mild, metal-free, and multicomponent route for the preparation of N-acyl amidines from nitroalkene derivatives, dibromo amides, and amines has been developed that accesses an initial α,α-dibromonitroalkane intermediate that can undergo C-C bond cleavage. This protocol offers an alternative approach toward N-acyl amidines and features the rapid construction of amidine frameworks with high diversity and complexity. The procedure also accesses bisamidine and α,β-unsaturated amidines which are challenging targets by traditional methods.
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http://dx.doi.org/10.1021/acs.joc.8b02998 | DOI Listing |
ACS Pharmacol Transl Sci
December 2024
University of Münster, Institute of Pharmaceutical and Medicinal Chemistry, Pharmacampus, Münster 48149, Germany.
The human protein kinase CK2 is a promising target for cancer treatment. Only two CK2 inhibitors have reached clinical trials until today. Among others, a dibenzofuran scaffold has emerged as highly prospective for the development of new CK2 inhibitors.
View Article and Find Full Text PDFJ Med Chem
January 2025
Molecular Biophysics Unit, Indian Institute of Science, Bangalore 560012, India.
FadD32, a fatty acyl-AMP ligase, plays an indispensable role in mycobacterial mycolic acid synthesis and is a validated target for tuberculosis (TB) drug development. The crystal structure of (Mtb)FadD32 has laid the foundation of structure-based drug discovery against this crucial enzyme. Here, we screened the "isoxazole" scaffold containing molecules against MtbFadD32 and identified a compound 2,4-dibromo-6-[3-(trifluoromethyl)-1,2-oxazol-5-yl]phenol (M1) with specific inhibitory activity against Mtb.
View Article and Find Full Text PDFChem Pharm Bull (Tokyo)
December 2024
Faculty of Pharmacy, Osaka Ohtani University.
We have investigated the base-induced long-range halogen dance reactions of 4,5-dibromo- or 4-bromo-5-iodothiazoles bearing sulfur-containing aromatic heterocycles at the C2-position. We have found that the reaction occurs in bithiazole regioisomers or (thiophenyl)thiazole derivatives, in which the C-5 halo group on the thiazole halogen donor regioselectively migrates to a halogen acceptor ring after treatment with lithium bis(trimethylsilyl)amide. The substrate with a thiophen-2-yl substituent required highly basic P
Org Biomol Chem
December 2024
Department of Chemistry, Southern Federal University, Zorge str. 7, 344090 Rostov-on-Don, Russian Federation.
6-Bromo- and 6,7-dibromo-1,3-dimethyl-1-perimidin-2(3)-ones were arylated with arylboronic acids under Suzuki-Miyaura reaction conditions to afford 6-aryl-, 6-bromo-7-aryl- and 6,7-diaryl-1,3-dimethyl-1-perimidin-2(3)-ones. A comparison of the X-ray structural parameters of -diaryl derivatives of 1,3-dimethyl-1-perimidin-2(3)-one, naphthalene and 1,8-bis(dimethylamino)naphthalene (proton sponge) was performed. Based on the data of dynamic H NMR spectroscopy and quantum-chemical calculations, barriers to /-isomerization of 6,7-diaryl-1,3-dimethyl-1-perimidin-2(3)-ones were estimated.
View Article and Find Full Text PDFDalton Trans
December 2024
Department of Chemistry, Engineering Faculty, Inorganic Chemistry Department, Istanbul University-Cerrahpasa, 34320, Istanbul, Turkiye.
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