Abstract
Quinoxaline derivatized with coumarin viz., 3a–f and with sydnones viz., 7a–0 were synthesized using pyridine as catalyst. Among the coumarin derivatives, 3a and 3b have been screened for anticancer activity against 60 human cancer cell lines at NIH (USA). Compound 3a has shown 55.75 % GI against Melanoma (MALME-M) tumor cell line. Further, the sydnone derivatives 7d–i inhibited the Mycobacterium tuberculae H37RV.
Similar content being viewed by others
References
Abu-Hashem AA, Gouda MA, Badria FA (2010) Synthesis of some new pyrimido[2′,1′:2,3]thiazolo[4,5-b]quinoxaline derivatives as anti- inflammatory and analgesic agents. Eur J Med Chem 45:1976–1981
Bansode S, Kamble R (2012) Synthesis of novel 2-(3′-arylsydnon-4′-ylidene)-5′-substituted-[1,3,4]-thiadiazolylamines and [1,3,4]-thiadiazol-2′-yl-3-oxo-[1,2,4]-triazoles as antimicrobial agents. Med Chem Res 21:867–873
Chandra Shekhar A, Shanthan Rao P, Narsaiah B, Allanki AD, Singh PS (2014) Emergence of pyrido quinoxalines as new family of antimalarial agents. Eur J Med Chem 77:280–287
Chandrasekhar R, Nanjan MJ (2012) Sydnones: a brief review. Mini Rev Med Chem 12:1359–1365
Cooke D, Fitzpatrick B, O’Kennedy R, McCormack T, Egan D (1997) Coumarins—multifaceted molecules with many analytical and other applications. In: Kennedy RO, Thornes RD (eds) Coumarins: biology, applications and mode of action. Wiley, Chichester, pp 303–332
Dalia HS (2013) Synthesis, characterization, anti-bacterial and anti-fungal activities of new quinoxaline 1,4-di-N-oxide derivatives. Int J Org Chem 3:65–72
Dorababu A, Kamble RR, Kattimani PP, Kariduraganavar MY, Kamble AA (2014) Ceric ammonium nitrate catalysed stereoselective synthesis of β-aminoketones using 3-Aryl-4-formylsydnones. Lett Org Chem 11:244–249
Esther V, Raquel V, Asuncio´n B, Beatriz S, Silvia P, Ignacio A, Joseph AM, Anne JL, Scott GF, Sang-hyun C, Antonio M, Robert CG (2008) Efficacy of quinoxaline-2-carboxylate 1,4-Di-N-oxide derivatives in experimental tuberculosis. Antimicrob Agents Chemother 52:3321–3326
Fun HK, Chia TS, Nitinchandra Kalluraya B, Shetty S (2012) 4-Bromoacetyl-3-phenylsydnone. Acta Cryst E 68:o2103
Gireesh TM, Kamble RR, Taj T, Kattimani PP, Meti GY (2013) Synthesis of novel imidazo[2,1-b][1,3,4]thiadiazoles appended to sydnone as anticancer agents. Med Chem Res 22:4367–4375
Hadda TB, Rahima B, Kerbal A, Bouchra FB, Akkurt M, Demailly G, Benazza M (2007) Synthesis and antitubercular activity of spiroheterocycles: 2,2′,4′,5′-tetra-substituted-1,2,2′,4′-tetrahydro-4H-spiro[isoquinoline-3,3′-pyrazol]-4-ones. ARKIVOC xiv: 276–288. http://dtp.nic.nih.gov/docs/compare.html
Kattimani PP, Kamble RR, Kariduraganavar MY, Dorababu A, Hunnur RK (2013) Synthesis, characterization and in vitro anticancer evaluation of novel 1,2,4-triazolin-3-one derivatives. Eur J Med Chem 62:232–240
Kulkarni MV, Patil VD, Biradar VN, Nanjappa S (1981) Synthesis and biological properties of some 3-heterocyclic substituted coumarins. Arch Pharm 314:435–439
Mohamed GT, Serry AAEB, Magda NAN (2015) Synthesis and biological evaluation of new 3-(4-substituted phenyl)aminoquinoxaline derivatives as anticancer agents. Heterocycl Commun 21:25–35
Musiliyu AM, Badisa VLD, Lekan ML, John C, Andre S, Ahkinyala A (2011) Cytotoxic activity of new acetoxycoumarin derivatives in cancer cell lines. Anticancer Res 31:2017–2022
Noolvi MN, Patel HM, Bhardwaj V, Chauhan A (2011) Synthesis and in vitro antitumor activity of substituted quinazoline and quinoxaline derivatives: search for anticancer agent. Eur J Med Chem 46:2327–2346
Patel AK, Patel NH, Patel MA, Brahmbhatt DI (2010) Synthesis, characterization and antimicrobial activity of some 4-aryl-2,6-di(coumarin-3-yl)pyridines. ARKIVOC 11:28–38
Puratchikody A, Natarajan R, Jayapal M, Doble M (2011) Synthesis, in vitro antitubercular activity and 3D-QSAR of novel quinoxaline derivatives. Chem Biol Drug Des 78:988–998
Radhia EA, Jianrong L, Sophie B, Damien C, Olivier C, Jean-Michel C, Elisabeth MN, Emmanuel M (2014) Synthesis and biological evaluation of new quinoxaline derivatives of ICF01012 as melanoma-targeting probes. ACS Med Chem Lett 5:468–473
Rao GK, Kotnal RB, Pai PNS (2009) Synthesis and evaluation of N′-((substituted phenyl) methylidene)-2-(3-methyl-2-oxoquinoxalin-l (2H)-yl)acetohydrazide for possible antibacterial and antifungal activities. Intl J Biol Chem 3:71–77
Sahm DF, Washington JA (1991) II: Antibacterial susceptibility tests: dilution Methods. In: Balows A (ed) Manual of clinical microbiology, 5th edn. American Society for Microbiology, Washington, DC, pp 1105–1116
Sandra P (2004) Quinoxaline chemistry, synthesis of methyl [4-(Substituted-2-quinoxalinyloxy)phenyl] acetate and evaluation of anticancer activity. II FARMCO 59:185–194
Taj T, Raikar SV, Kamble RR (2014) Synthetic utility of sydnones to couple pharmacologically important heterocycles for antitubercular activity. Arab J Chem 7:900–905
Tegginamath G, Kamble RR, Kattimani PP, Dorababu A, Manikantha M, Hoskeri JH (2013) Synthesis of sydnone substituted biginelli derivatives as hyaluronidase inhibitors. Arch Pharm Chem Life Sci 346:1–9
Zhiwei C, Jianhao B, Weike S (2013) Synthesis and antitumor activity of novel coumarin derivatives via a three-component reaction in water. Chin J Chem 31:507–514
Acknowledgments
The authors acknowledge the NCI, NIH, Bethesda, USA for selecting samples for in vitro anticancer analyses under DTP. The authors are grateful to NGH College of Dental sciences, Belgaum, Karnataka, India for anti-tubercular activity. The authors wish to thank the University Scientific Instrumentation Centre (USIC), Karnataka University, Dharwad, NMR Research Centre, Indian Institute of Science (IISc), Bengaluru, India for carrying out the spectral analyses. The authors (AAK and RRK) are also thankful to UGC, New Delhi for providing financial assistant under UGC-UPE thrust area “Antitumor activity: An Integrated Approach”. Vide F. No. 14-3/2012 (NS/PE).
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Kamble, A.A., Kamble, R.R., Kumbar, M.N. et al. Pyridine-catalyzed synthesis of quinoxalines as anticancer and anti-tubercular agents. Med Chem Res 25, 1163–1174 (2016). https://doi.org/10.1007/s00044-016-1558-2
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00044-016-1558-2