Microwave-assisted CAN-catalyzed solvent-free synthesis of N-allyl quinolone-based pyrano[4,3-b]chromene and benzopyrano[3,2-c]chromene derivatives and their antimicrobial activity

Medicinal Chemistry Research

Volumn 22, Issue 2, 2013, Pages 905-915

  Jardosh, Hardik H ^a   Patel, Manish P ^a  

^a SARDAR PATEL UNIVERSITY   (India)

Author keywords

Antimicrobial activity; Atom economy; Microwave assisted synthesis; N allyl quinolones; Pyranochromenes; Solvent free synthesis

Indexed keywords

10 (1 ALLYL 2 OXO 1,2 DIHYDROQUINOLIN 3 YL) 3 METHYL 7,8 DIHYDROPYRANO[4,3 B]CHROMENE 1,9(6H,10H) DIONE; 10 (1 ALLYL 2 OXO 1,2 DIHYDROQUINOLIN 3 YL) 3,7,7 TRIMETHYL 7,8 DIHYDROPYRANO[4,3 B]CHROMENE 1,9(6H,10H) DIONE; 10 (1 ALLYL 6 CHLORO 2 OXO 1,2 DIHYDROQUINOLIN 3 YL) 3 METHYL 7,8 DIHYDROPYRANO[4,3 B]CHROMENE 1,9(6H,10H) DIONE; 10 (1 ALLYL 6 CHLORO 2 OXO 1,2 DIHYDROQUINOLIN 3 YL) 3,7,7 TRIMETHYL 7,8 DIHYDROPYRANO[4,3 B]CHROMENE 1,9(6H,10H) DIONE; 10 (1 ALLYL 6 METHOXY 2 OXO 1,2 DIHYDROQUINOLIN 3 YL) 3 METHYL 7,8 DIHYDROPYRANO[4,3 B]CHROMENE 1,9(6H,10H) DIONE; 10 (1 ALLYL 6 METHOXY 2 OXO 1,2 DIHYDROQUINOLIN 3 YL) 3,7,7 TRIMETHYL 7,8 DIHYDROPYRANO[4,3 B]CHROMENE 1,9(6H,10H) DIONE; 10 (1 ALLYL 6 METHYL 2 OXO 1,2 DIHYDROQUINOLIN 3 YL) 3 METHYL 7,8 DIHYDROPYRANO[4,3 B]CHROMENE 1,9(6H,10H) DIONE; 10 (1 ALLYL 6 METHYL 2 OXO 1,2 DIHYDROQUINOLIN 3 YL) 3,7,7 TRIMETHYL 7,8 DIHYDROPYRANO[4,3 B]CHROMENE 1,9(6H,10H) DIONE; 7 (1 ALLYL 2 OXO 1,2 DIHYDROQUINOLIN 3 YL) 10,10 DIMETHYL 9,11 DIHYDROBENZOPYRANO[3,2 C]CHROMENE 6,8(7H) DIONE; 7 (1 ALLYL 2 OXO 1,2 DIHYDROQUINOLIN 3 YL) 9,10,11 TRIDIHYDROBENZOPYRANO[3,2 C]CHROMENE 6,8(7H) DIONE; 7 (1 ALLYL 6 CHLORO 2 OXO 1,2 DIHYDROQUINOLIN 3 YL) 10,10 DIMETHYL 9,11 DIHYDROBENZOPYRANO[3,2 C]CHROMENE 6,8(7H) DIONE; 7 (1 ALLYL 6 CHLORO 2 OXO 1,2 DIHYDROQUINOLIN 3 YL) 9,10,11 TRIHYDROBENZOPYRANO[3,2 C]CHROMENE 6,8(7H) DIONE; 7 (1 ALLYL 6 METHOXY 2 OXO 1,2 DIHYDROQUINOLIN 3 YL) 10,10 DIMETHYL 9,11 DIHYDROBENZOPYRANO[3,2 C]CHROMENE 6,8(7H) DIONE; 7 (1 ALLYL 6 METHOXY 2 OXO 1,2 DIHYDROQUINOLIN 3 YL) 9,10,11 TRIDIHYDROBENZOPYRANO[3,2 C]CHROMENE 6,8(7H) DIONE; 7 (1 ALLYL 6 METHYL 1,2 DIHYDROQUINOLIN 3 YL) 9,10,11 TRIDIHYDROBENZOPYRANO[3,2 C]CHROMENE 6,8(7H) DIONE; 7 (1 ALLYL 6 METHYL 2 OXO 1,2 DIHYDROQUINOLIN 3 YL) 10,10 DIMETHYL 9,11 DIHYDROBENZOPYRANO[3,2 C]CHROMENE 6,8(7H) DIONE; AMPICILLIN; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; BENZOPYRANO[3,2 C]CHROMENE DERIVATIVE; CHLORAMPHENICOL; CHROMENE DERIVATIVE; CIPROFLOXACIN; GRISEOFULVIN; NYSTATIN; PYRANO[4,3 B]CHROMENE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CONTROLLED STUDY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROSCOPY; MICROWAVE IRRADIATION; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION;

EID: 84873999734     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-012-0085-z     Document Type: Article

References (29)

1. Bianchi G, Tava A (1987) Synthesis of (2R)-(+)-2,3-dihydro-2,6-dimethyl- 4H-pyran-4-one, a homologue of pheromones of a species in the hepialidae family. Agric Biol Chem 51:2001-2002. doi: 10.1271/bbb1961.51.2001
2. Constable DJC, Curzons AD, Cunningham VL (2002) Metrics to 'green' chemistry - which are the best? Green Chem 4:521-527. doi: 10.1039/b206169b
3. Hiramoto K, Nasuhara A, Michiloshi K, Kato T, Kikugawa K (1997) DNA strand-breaking activity and mutagenicity of 2,3-dihydro-3,5-dihydroxy-6-methyl- 4H-pyran-4-one (DDMP), a Maillard reaction product of glucose and glycine. Mutat Res 395:47-56. doi: 10.1016/S1383-5718(97)00141-1
4. Infectious Diseases Society of America (2010) The 10 × 20 initiative: pursuing a global commitment to develop 10 new antibacterial drugs by 2020. Clin Infect Dis 50:1081-1083. doi: 10.1086/652237
5. Kategaonkar AH, Labade VB, Shinde PV, Kategaonkar AH, Shingate BB, Shingare MS (2010) Synthesis and antimicrobial activity of tetrazolo[1,5-a]- quinoline-4-carbonitrile derivatives. Monatsh Chem 141:787-791. doi: 10.1007/s00706-010-0324-2
6. Kathrotiya HG, Patel MP (2011) Microwave-assisted synthesis of 3′-indolyl substituted 4H-chromenes catalyzed by DMAP and their antimicrobial activity. Med Chem Res. doi: 10.1007/s00044-011-9861-4
7. Kaur K, Jain M, Reddy RP, Jain R (2010) Quinolines and structurally related heterocycles as antimalarials. Eur J Med Chem 45:3245-3264. doi: 10.1016/j.ejmech.2010.04.011
8. Kidwai M, Negi N (1997) Synthesis of some novel substituted quinolines as potent analgesic agents. Monatsh Chem 128:85-89. doi: 10.1007/BF00807642
9. Kumar A, Srivastava S, Gupta G, Chaturvedi V, Sinha S, Srivastava R (2011) Natural product inspired diversity oriented synthesis of tetrahydroquinoline scaffolds as antitubercular agent. ACS Comb Sci 13:65-71. doi: 10.1021/co100022h
10. Lew A, Krutzik PO, Hart ME, Chamberlin AR (2002) Increasing rates of reaction: microwave-assisted organic synthesis for combinatorial chemistry. J Comb Chem 4:95-105. doi: 10.1021/cc010048o
11. Li J, Tan JZ, Chen LL et al (2006) Design, synthesis and antitumor evaluation of a new series of N-substituted-thiourea derivatives. Acta Pharmacol Sin 27:1259-1271. doi: 10.1111/j.1745-7254.2006.00437.x
12. Makawana JA, Patel MP, Patel RG (2011) Synthesis and in vitro antimicrobial evaluation of penta-substituted pyridine derivatives bearing the quinoline nucleus. Med Chem Res. doi: 10.1007/s00044-011-9568-6
13. Miceli MH, Bernardoa SM, Lee SA (2009) In vitro analyses of the combination of high-dose doxycycline and antifungal agents against candida albicans biofilms. Int J Antimicrob Agents 34:326-332. doi: 10.1016/j. ijantimicag.2009.04.011
14. Mohr SJ, Chirigos MA, Fuhrman FS, Pryor JW (1975) Pyran copolymer as an effective adjuvant to chemotherapy against a murine leukemia and solid tumor. Cancer Res 35:3750-3754. http://cancerres.aacrjournals.org/content/35/12/3750
15. Mungra DC, Patel MP, Patel RG (2011a) Microwave-assisted synthesis of some new tetrazolo [1,5-a]quinoline-based benzimidazoles catalyzed by p-TsOH and investigation of their antimicrobial activity. Med Chem Res 20:782-789. doi: 10.1007/s00044-010-9388-0
16. Mungra DC, Patel MP, Rajani DP, Patel RG (2011b) Synthesis and identification of β-aryloxyquinolines and their pyrano[3,2-c]chromene derivatives as a new class of antimicrobial and antituberculosis agents. Eur J Med Chem 46:4192-4200. doi: 10.1016/j.ejmech.2011.06.022
17. Nair V, Deepthi A (2007) Cerium(IV) ammonium nitrate a versatile single-electron oxidant. Chem Rev 107:1862-1891. doi: 10.1021/cr068408n
18. NCCLS (National Committee for Clinical Laboratory Standards) (2002) Performance standards for antimicrobial susceptibility testing: twelfth informational supplement. ISBN 1-56238-454-6, M100-S12, M7
19. Parent KE Cleaning up with atom economy. Green Chemistry Institute American Chemical Society, Washington. http://portal.acs.org/portal/fileFetch/C/ CTP-005634/pdf/CTP-005634.pdf
20. Praveen C, Ayyanar A, Perumal PT (2011) Practical synthesis, anticonvulsant, and antimicrobial activity of N-allyl and N-propargyl di(indolyl)indolin-2-ones. Bioorg Med Chem Lett 21:4072-4077. doi: 10.1016/j.bmcl.2011.04.117
21. Shafiee A, Motamedi R, Firuzi O, Meili S, Mehdipour AR, Miri R (2011) Synthesis and cytotoxic activity of novel benzopyrano[3,2-c]chromene-6,8-dione derivatives. Med Chem Res 20:466-474. doi: 10.1007/s00044-010-9340-3
22. 2-catalyzed three component, one-pot cyclocondensation reaction of some new octahydroquinazolinone derivatives and access their bio-potential. Med Chem Res. doi: 10.1007/s00044-011-9628-y
23. Shah NM, Patel MP, Patel RG (2011) An efficient and facile synthesis of 1H-Pyrazolo[1,2-b]phthalazine-5,10-dione derivatives of biological interest. J Heterocycl Chem. doi: 10.1002/jhet.918
24. Smith WP, Sollis LS, Howes DP, Cherry CP, Starkey DI, Cobley NK (1998) Dihydropyrancarboxamides related to zanamivir: a new series of inhibitors of influenza virus sialidases. 1. Discovery, synthesis, biological activity, and structure-activity relationships of 4-guanidino- and 4-amino-4h-pyran-6- carboxamides. J Med Chem 41:787-797. doi: 10.1021/jm970374b
25. Songa J, Thamlikitkul V, Hsueh P (2011) Clinical and economic burden of community-acquired pneumonia amongst adults in the Asia-Pacific region. Int J Antimicrob Agents 38:108-117. doi: 10.1016/j.ijantimicag.2011.02.017
26. Sridharan V, Menendez JC (2010) Cerium(IV) ammonium nitrate as a catalyst in organic synthesis. Chem Rev 110:3805-3849. doi: 10.1021/cr100004p
27. Srivastava A, Singh RM (2005) Vilsmeier-Haack reagent: a facile synthesis of 2-chloro-3-formylquinolines from N-arylacetamides and transformation into different functionalities. Indian J Chem 44B:1868-1875
28. Strekowski L, Mokrosz JL, Honkan VA, Czarny A, Cegla MT, Patterson SE, Wydra RL, Schinazi RF (1991) Synthesis and quantitative structure-activity relationship analysis of 2-(aryl or heteroaryl)quinolin-4-amines, a new class of anti-HIV-1 agents. J Med Chem 34:1739-1746. doi: 10.1021/jm00109a031
29. Thumar NJ, Patel MP (2011) Synthesis, characterization and biological activity of some new carbostyril bearing 1H-pyrazole moiety. Med Chem Res. doi: 10.1007/s00044-011-9693-2