AlCl 3 induced (hetero)arylation of 2,3-dichloroquinoxaline: A one-pot synthesis of mono/disubstituted quinoxalines as potential antitubercular agents

K. Shiva Kumar; D. Rambabu; Sandhya Sandra; Ravikumar Kapavarapu; G. Rama Krishna; M. V. Basaveswara Rao; Kiranam Chatti; C. Malla Reddy; Parimal Misra; Manojit Pal

doi:10.1016/j.bmc.2012.01.012

AlCl ₃ induced (hetero)arylation of 2,3-dichloroquinoxaline: A one-pot synthesis of mono/disubstituted quinoxalines as potential antitubercular agents

K. Shiva Kumar, D. Rambabu, Sandhya Sandra, Ravikumar Kapavarapu, G. Rama Krishna, M. V. Basaveswara Rao, Kiranam Chatti, C. Malla Reddy, Parimal Misra, Manojit Pal

Research output: Contribution to journal › Article › peer-review

45 Scopus citations

Abstract

A direct and single-step method has been developed for the synthesis of mono and 2,3-disubstituted quinoxalines by using a AlCl ₃ induced (hetero)arylation of 2,3-dichloroquinoxaline. Both symmetrical and unsymmetrical 2,3-disubstituted quinoxalines can be prepared conveniently by using this method under appropriate reaction conditions. The reaction proceeds via C-C bond formation and can be utilized for the preparation of a variety of quinoxaline derivatives from readily available starting materials and reagents. The molecular structure of a representative compound was confirmed by single crystal X-ray diffraction study. Some of the compounds synthesized were tested for chorismate mutase inhibitory properties in vitro and one compound showed promising activity representing one of the few examples of chorismate mutase inhibition by a heteroarene based small molecule.

Original language	English
Pages (from-to)	1711-1722
Number of pages	12
Journal	Bioorganic and Medicinal Chemistry
Volume	20
Issue number	5
DOIs	https://doi.org/10.1016/j.bmc.2012.01.012
State	Published - 1 Mar 2012
Externally published	Yes

Keywords

AlCl
Chorismate mutase
Indole
Quinoxalines
X-ray

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

Access to Document

10.1016/j.bmc.2012.01.012

Cite this

Kumar, K. S., Rambabu, D., Sandra, S., Kapavarapu, R., Krishna, G. R., Basaveswara Rao, M. V., Chatti, K., Reddy, C. M., Misra, P., & Pal, M. (2012). AlCl ₃ induced (hetero)arylation of 2,3-dichloroquinoxaline: A one-pot synthesis of mono/disubstituted quinoxalines as potential antitubercular agents. Bioorganic and Medicinal Chemistry, 20(5), 1711-1722. https://doi.org/10.1016/j.bmc.2012.01.012

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abstract = "A direct and single-step method has been developed for the synthesis of mono and 2,3-disubstituted quinoxalines by using a AlCl 3 induced (hetero)arylation of 2,3-dichloroquinoxaline. Both symmetrical and unsymmetrical 2,3-disubstituted quinoxalines can be prepared conveniently by using this method under appropriate reaction conditions. The reaction proceeds via C-C bond formation and can be utilized for the preparation of a variety of quinoxaline derivatives from readily available starting materials and reagents. The molecular structure of a representative compound was confirmed by single crystal X-ray diffraction study. Some of the compounds synthesized were tested for chorismate mutase inhibitory properties in vitro and one compound showed promising activity representing one of the few examples of chorismate mutase inhibition by a heteroarene based small molecule.",

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Kumar, KS, Rambabu, D, Sandra, S, Kapavarapu, R, Krishna, GR, Basaveswara Rao, MV, Chatti, K, Reddy, CM, Misra, P & Pal, M 2012, 'AlCl ₃ induced (hetero)arylation of 2,3-dichloroquinoxaline: A one-pot synthesis of mono/disubstituted quinoxalines as potential antitubercular agents', Bioorganic and Medicinal Chemistry, vol. 20, no. 5, pp. 1711-1722. https://doi.org/10.1016/j.bmc.2012.01.012

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AU - Kumar, K. Shiva

AU - Rambabu, D.

AU - Sandra, Sandhya

AU - Kapavarapu, Ravikumar

AU - Krishna, G. Rama

AU - Basaveswara Rao, M. V.

AU - Chatti, Kiranam

AU - Reddy, C. Malla

AU - Misra, Parimal

AU - Pal, Manojit

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