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Pyridine derivatives of isoindoline

Isoindoline and its derivatives have attracted great attention from medicinal and synthetic organic chemists due to their wide range of biological activities. They are present in many natural and synthetic biologically active compounds. For example, staurosporine, isolated from bacteria Streptomices staurosporeus, acts as protein kinase C inhibitor ; indoprofen, synthetic derivative of isoindoline, is an anti-inflammatory drug ; pazinaclone is anxiolytic agent.[1] N-substituted derivatives of isoindoline inhibit dipeptidyl peptidases 8 and 9 which are active in Type II diabetes.[2] There are also many reports on their antitumor activity.[3, 4] Here we present synthesis of pyridine derivatives of isoindoline substituted in positions 1 and 2 as potentially biologically active compounds. Condensation of o-phthalaldehyde and substituted amino-pyridines in absolute ethanol at room temperature gave desired 1-iminopyridil-2-pyridil-isoindolines. All compounds are characterized by 1H and 13C NMR spectroscopy as well as UV and IR spectroscopy. References: 1. Kundu, N. G. ; Khan, M. W. ; Mukhopadhyay, R. J. Indian Chem. Soc. 2001, 78, 671-688. 2. Van Goethem S. ; Van der Veken, P. ; Dubois, V. ; Soroka, A. ; Lambeir, A.-M. ; Chen, X. ; Haemers, A. ; Scharpe, S. ; De Meester, I. ; Augustyns, K. Bioorg. Med. Chem. Lett. 2008, 18, 4159-4162. 3. Bregger, D. ; Citarella, R. ; Dutia, M. ; Greenberger, L. ; Hallett, W. ; Paul, R. ; Powell, D. J. Med. Chem. 1999, 42, 2145-2161. 4. Masterson, L. A. ; Croker, S. J. ; Jenkins, T. C. ; Howard, P. W. ; Thurston, D. E. Bioorg. Med. Chem. Lett. 2004, 14, 901-904.

isoindoline; pyridine; heterocycles; synthesis; NMR spectroscopy

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