Synthesis of {2,3-Dihydro-7-halopyrrolo-[(2,1-b)]-quinazolin-9-(1H)-one and 2,3-Dihydro-5,7-dihalopyrrolo-[(2,1-b)]-quinazolin-9-(1H)-one}: New Analogs of Deoxyvasicinone

Abstract

A series of novel halogen-substituted deoxyvasicinone {2,3-dihydro-7-halopyrrolo-[(2,1-b)]-quinazolin-9-(1H)-one and 2,3-dihydro-5,7-dihalopyrrolo-[(2,1-b)]-quinazolin-9-(1H)-one} derivatives was synthesized by condensation of halogenated anthranilic acids (2, 3, 4, 5) with 4-aminobutyric acid (6) in refluxing m-xylene over phosphorus pentoxide for 3 h to give the desired compounds (7a–7d).

GRAPHICAL ABSTRACT

Keywords:

• Adhatoda vasica
• deoxyvasicinone
• vasicine
• vasicinone

ACKNOWLEDGMENTS

The authors thank Gabrielle Jones and Octavia Felton for their assistance during the preparation of this manuscript and the National Institutes of Health (NIH/NIGMS) for support of this work.