An efficient Heck-type C-glycosylation of glycals via the C-N bond cleavage of aryl hydrazines has been developed. The flexibility of the reaction was tested by the substrate scope, consisting of glycals from different carbohydrate origins as well as aryl hydrazines with various substituents. Pure α-C-glycosides were obtained when (3R)-glycals were employed, whereas α,β mixtures were observed with (3S)-glycals.
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http://dx.doi.org/10.1021/jo401032r | DOI Listing |
Chemistry
January 2025
Janssen Pharmaceutica NV, chemcial process R&D, BELGIUM.
The manuscript describes the development of an efficient synthetic route to cinnolines, facilitating faster access to JNJ-8003 related Respiratory Syncytial Virus (RSV) non-nucleoside (NNI) inhibitors. Starting from correctly functionalized aryl halides, a Sonogashira reaction followed by SNAr reaction with hydrazine 1,2-dicabroxylate reagents provided dihydrocinnolines directly via in situ 6-endo-dig cyclization. The dihydrocinnolines were conveniently transformed to corresponding cinnolines in one step.
View Article and Find Full Text PDFSci Rep
January 2025
Bioinformatics Centre, Savitribai Phule Pune University, Pune, Maharashtra, 411007, India.
COVID-19 has proved to be a global health crisis during the pandemic, and the emerging JN.1 variant is a potential threat. Therefore, finding alternative antivirals is of utmost priority.
View Article and Find Full Text PDFJ Org Chem
January 2025
Department of Chemistry, Indian Institute of Science Education and Research (IISER) Tirupati, Tirupati 517619, India.
The development of efficient and robust catalytic systems based on earth-abundant transition metals for fundamentally new transformations is crucial for sustainable chemical synthesis. Herein, an effective and selective Ni-catalyzed dehydrogenative coupling of alcohols with hydrazines with the liberation of ammonia gas is reported. Although several methods were documented for the -alkylation reaction, the present strategy is conceptually novel, and the reaction proceeds through a pathway involving N-N bond cleavage of phenylhydrazine followed by hydrogen autotransfer.
View Article and Find Full Text PDFMolecules
December 2024
Medicinal Chemistry Laboratory, Department of Biosciences, Jamia Millia Islamia, New Delhi 110025, India.
In response to the escalating crisis of antimicrobial resistance (AMR), there is an urgent need to research and develop novel antibiotics. This study presents the synthesis and assessment of innovative 4-aminoquinoline-benzohydrazide-based molecular hybrids bearing aryl aldehydes () and substituted isatin warheads (), characterized using multispectroscopic techniques with high purity confirmed by HRMS. The compounds were evaluated against a panel of clinically relevant antibacterial strains including the Gram-positive , , and and a Gram-negative bacterial strain.
View Article and Find Full Text PDFJ Org Chem
December 2024
Pfizer Oncology Medicinal Chemistry, San Diego, California 92121, United States.
A 3-step modular procedure combining carboxylic acids with acyl hydrazines provides access to medicinally relevant [1,2,4]-fused triazoles. Good to excellent yields are achieved with tolerance of aliphatic and aryl substituents as well as 5-, 6-, and 7-membered rings for the fused ring. Conditions that can avoid column chromatography and be applicable for both small scale discovery efforts as well as large scale development processes are demonstrated within.
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