The synthesis of triazolyl azido alcohols from terminal alkyne via oxirane ring-opening of epichlorohydrin, followed by click reaction with alkynes, and subsequent azidation of chlorohydroxy triazoles was achieved under a one-pot methodology. The developed triazolyl azido alcohols were further utilized for the synthesis of a diverse range of morpholine-fused triazoles of chemotherapeutic value. The structure of all developed compounds has been elucidated using IR, NMR, MS, and elemental analysis, where four of them have been characterized by single-crystal X-ray analysis.
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ACS Omega
October 2017
Garware Research Centre, Department of Chemistry, Department of Chemistry, Institute of Bio-informatics and Biotechnology, and Central Instrumentation Facility, Savitribai Phule Pune University (Formerly University of Pune), Ganeshkhind Road, Pune 411007, India.
Synthesis of iminosugars , , , and and N-alkyl (ethyl, butyl, hexyl, octyl, decyl, and dodecyl) derivatives - and - spiro-linked with morpholine-fused 1,2,3-triazole is described. Conformation of the piperidine ring in each spiro-iminosugar was evaluated by H NMR spectroscopy, and conformational change in N-alkylated compounds - with respect to parent spiro-iminosugar is supported by density functional theory calculations. Out of 16 new spiro-iminosugars, the spiro-iminosugars (IC = 0.
View Article and Find Full Text PDFEur J Med Chem
September 2015
Department of Medicinal Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Hyderabad 500 037, India. Electronic address:
A series of new spirooxindole-derived morpholine-fused-1,2,3-triazole derivatives has been synthesized from isatin spiro-epoxides. The protocol involves regiospecific isatin-epoxide ring opening with azide nucleophile followed by sequential O-propargylation, and intramolecular 1,3-dipolar cycloaddition reaction. These compounds have been evaluated for their antiproliferative activity against selected human tumor cell lines of lung (A549), breast (MCF-7), cervical (HeLa), and prostate (DU-145).
View Article and Find Full Text PDFJ Org Chem
June 2014
Department of Chemistry, Centre of Advanced Study, Faculty of Science, Banaras Hindu University, Varanasi-221005, India.
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