Citation: Sakineh Asghari, Nastaran Malekian, Roya Esmaeilpour, Mohammad Ahmadipour, Mojtaba Mohseni. Three-component synthesis and antibacterial evaluation of some novel 1,2-dihydroisoquinoline derivatives[J]. Chinese Chemical Letters, ;2014, 25(11): 1441-1444. doi: 10.1016/j.cclet.2014.05.047 shu

Three-component synthesis and antibacterial evaluation of some novel 1,2-dihydroisoquinoline derivatives

1.
a Department of Organic Chemistry, Faculty of Chemistry, University of Mazandaran, Babolsar 47416-95447, Iran;
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b Nano and Biotechnology Research Group, University of Mazandaran, Babolsar 47416-95447, Iran;
3.
c Department of Microbiology, Faculty of Science, University of Mazandaran, Babolsar 47416-95447, Iran

Corresponding author: Sakineh Asghari,
Received Date: 14 April 2014
Available Online: 19 May 2014

Isoquinoline reacts with dialkyl acetylenedicarboxylates in the presence of kojic acid or 8-hydroxyquinoline to generate 1,2-dihydroisoquinoline derivatives. The simplicity, mild reaction conditions and high yields of products make it an interesting process compared to other approaches. The compounds have been analyzed for antibacterial activity against Gram negative and Gram positive bacteria. The results indicated that 1,2-dihydroisoquinolines derived from kojic acid are effective against all of the studied bacteria especially against Bacillus subtilis, while the products obtained from 8-hydroxyquinoline are active only against Gram positive bacteria.
- Kojic acid,
- 8-Hydroxyquinolone,
- Dialkyl acetylenedicarboxylates,
- 1,2-Dihydroisoquinoline,
- Isoquinoline,
- Antibacterial activity
1. [1]
  [1] (a) C.P. Hansch, G. Sammes, J.B. Taylor, Comprehensive Medicinal Chemistry, Pergamon Press, Oxford, 1990; (b) K.W. Bentley, The Isoquinoline Alkaloide, Pergamon Press, London, 1965; (c) K.W. Bentley, b-Phenylethylamines and the isoquinoline alkaloids, Nat. Prob. Rep. 18 (2001) 148-170; (d) J.D. Scott, R.M. Williams, Chemistry and biology of the tetrahydroisoquinoline antitumor antibiotics, Chem. Rev. 102 (2002) 1669-1730.
2. [2]
  [2] (a) B.E. Maryanoff, D.F. Mc Comsey, J.F. Gardocki, et al., Pyrroloisoquinoline antidepressants. 2. In-depth exploration of structure-activity relationships, J. Med. Chem. 30 (1987) 1433-1454; (b) K.L. Sorgi, C.A. Maryanoff, D.F. Mc Comsey, D.W. Graden, B.E. Maryanoff, Asymmetric induction in an enammonium-iminium rearrangement. Mechanistic insight via NMR, deuterium labeling, and reaction rate studies. Application to the stereoselective synthesis of pyrroloisoquinoline antidepressants, J. Am. Chem. Soc. 112 (1990) 3567-3579.
3. [3]
  [3] E. Lukevics, I. Segal, A. Zablotskaya, S. Germane, Synthesis and neurotropic activity of novel quinoline derivatives, Molecules 2 (1997) 180-185.
4. [4]
  [4] (a) L.F. Tietze, N. Rackehmann, I. Miller, Enantioselective total syntheses of the ipecacuanha alkaloid emetine, the alangium alkaloid aubulosine and a novel benzoquinolizidine alkaloid by using a domino process, Chem. Eur. J. 10 (2004) 2722-2731; (b) H.J. Knjlker, S. Agarwal, Total synthesis of the antitumor active pyrrolo[2,1- a]isoquinoline alkaloid (±)-crispine A, Tetrahedron Lett. 46 (2005) 1173-1175.
5. [5]
  [5] J.S. Yadav, B.V. Subba Reddy, N.N. Yadav, M.K. Gupta, Three-component coupling reactions of isoquinolines, dimethyl acetylenedicarboxylate and indoles: a facile synthesis of 3-indolyl-1,2-dihydro-2-isoquinolinyl-2-butenedioate, Tetrahedron Lett. 49 (2008) 2815-2819.
6. [6]
  [6] M. Nassiri, M.T. Maghsoodlou, R. Heydari, S.M. Habibi Khorassani, Novel multicomponent reactions involving isoquinoline or phenanthridine and activated acetylenic ester in the presence of heterocyclic NH or 1,3-dicarbonyl compounds, Mol. Divers. 12 (2008) 111-117.
7. [7]
  [7] I. Yavari, M. Ghazanfarpour-Darjani, M. Sabbaghan, Z. Hossaini, Synthesis of dimethyl 1,2-dihydroisoquinolines through the reaction of isoquinoline and dimethyl acetylenedicarboxylate in the presence of amides, Tetrahedron Lett. 48 (2007) 3749-3751.
8. [8]
  [8] J.S. Yadav, B.V. Subba Reddy, N.N. Yadav, M.K. Gupta, B. Sridhar, Gold(Ⅲ) chloridecatalyzed three-component reaction: a facile synthesis of alkynyl derivatives of 1,2-dihydroquinolines and isoquinolines, J. Org. Chem. 73 (2008) 6857-6859.
9. [9]
  [9] A. Shaabani, A.H. Rezayan, A. Sarvary, M. Heidary, N. Seik Weng, Synthesis of highly stable unusual charge separated pyridinium, isoquinolinium, quinolinium, and Nmethylimidazolium tetronic acid zwitterions, Tetrahedron 65 (2009) 6063-6068.
10. [10]
  [10] E.Y. Xia, J. Sun, R. Yao, C.G. Yan, Synthesis of zwitterionic salts via three component reactions of nitrogen-containing heterocycles, acetylenedicarboxylate and cyclic 1,3-dicarbonyl compounds, Tetrahedron 66 (2010) 3569-3574.
11. [11]
  [11] M. Anary-Abbasinejad, H. Anaraki-Ardakani, M.H. Mosslemina, H.R. Khavasi, Isoquinoline-catalyzed reaction between 4-hydroxycoumarin or 4-hydroxy-6- methylpyran-1-one and dialkyl acetylene dicarboxylates: synthesis of coumarin and pyranopyrane derivative, J. Braz. Chem. Soc. 21 (2010) 319-323.
12. [12]
  [12] I. Yavari, M. Piltan, L. Moradi, Synthesis of pyrrolo[2,1-a]isoquinolines from activated acetylenes, benzoylnitromethanes, and isoquinoline, Tetrahedron 65 (2009) 2067-2071.
13. [13]
  [13] F. Khaleghi, L.B. Din, I. Jantan, W.A. Yaacob, M.A. Khalilzadeh, Facile synthesis of novel 1,4-benzoxazepin-2-one derivatives, Tetrahedron Lett.52 (2011) 7182-7184.
14. [14]
  [14] J. Brtko, L. Rondahl, M. Fickova, et al., Kojic acid and its derivatives: history and present state of art, Cent. Eur. J. Public Health 12 (2004) S16-S20.
15. [15]
  [15] R. Bentley, From miso, saké and shoyu to cosmetics: a century of science for kojic acid, Nat. Prod. Rep. 23 (2006) 1046-1062.
16. [16]
  [16] A.Y. Shen, C.P. Chen, S.A. Roffler, Chelating agent possessing cytotoxicity and antimicrobial activity: 7-morpholinomethyl-8-hydroxyquinoline, Life Sci. 64 (1999) 813-825.
17. [17]
  [17] Y. Higa, M. Kawawbe, K. Nabae, et al., Kojic acid-absence of tumor-initiating activity in rat liver, and of carcinogenic and photo-genotoxic potential in mouse skin, J. Toxicol. Sci. 32 (2007) 143-159.
18. [18]
  [18] P. Collery, F. Lechenault, A. Cazabat, et al., Inhibitory effects of gallium chloride and tris (8-quinolinolato) gallium Ⅲ on A549 human malignant cell line, Anticancer Res. 20 (2000) 955-958.
19. [19]
  [19] F.C. Wehner, P.G. Thiel, S.J. Van Rensburg, I.P.C. Demasius, Mutagenicity to Salmonella typhimurium of some Aspergillus and Penicillium mycotoxins, Mutat. Res. 58 (1978) 193-203.
20. [20]
  [20] D. Hudecova, M. Uher, J. Brtko, Halogenderivatives of kojic acid with antifungal effects, Biologia (Bratislava) 47 (1992) 483-488.
21. [21]
  [21] A. Albert, S.D. Rubbo, R.J. Goldacre, B.G. Balfour, The influence of chemical constitution of antibacterial activity. A study of 8-hydroxyquinolin (oxine) and related compounds, Br. J. Exp. Pathol. XXVⅢ (1947) 69-87.
22. [22]
  [22] El-R. Kenawy, Biologically active polymers IV. Synthesis and antimicrobial activity of polymers containing 8-hydroxyquinoline moiety, J. Appl. Polym. Sci. 82 (2001) 1364-1374.
23. [23]
  [23] S. Asghari, M. Faraji-Najjarkolaee, M. Ahmadipour, Regioselective vinylation of kojic acid using acetylenic esters in the presence of triphenylphosphine or tertbutyl isocyanide, Monatsh. Chem. 141 (2010) 781-786.
24. [24]
  [24] S. Asghari, A. Khabbazi Habibi, One pot three-component regioselective and diastereoselective synthesis of halogenated pyrido[2,1-b][1,3]oxazines, Tetrahedron 68 (2012) 8890-8898.
25. [25]
  [25] R. Huisgen, M. Morikawa, K. Herbig, E. Brunn, 1.4-Dipolare cycloadditionen, Ⅱ. Dreikomponenten-reaktionen des isochinolins mit acetylendicarbonsäureester und verschiedenen dipolarophilen, Chem. Ber. 100 (1967) 1094-1106.
26. [26]
  [26] V. Nair, S. Devipriya, S. Eringathodi, Efficient synthesis of [1,3]oxazino[2,3- a]quinoline derivatives by a novel 1,4-dipolar cycloaddition involving a quinoline- DMAD zwitterion and carbonyl compounds, Tetrahedron Lett. 48 (2007) 3667-3670.
27. [27]
  [27] A.N. Pillai, B. Rema Devi, E. Suresh, V. Nair, An efficient multicomponent protocol for the stereoselective synthesis of oxazinobenzothiazole derivatives, Tetrahedron Lett. 48 (2007) 4391-4393.
28. [28]
  [28] V. Nair, S. Devipriya, E. Suresh, Construction of heterocycles via 1,4-dipolar cycloaddition of quinoline-DMAD zwitterion with various dipolarophiles, Tetrahedron 64 (2008) 3567-3577.
29. [29]
  [29] M. Adib, E. Sheibani, M. Mostofi, K. Ghanbary, H.R. Bijanzadeh, Efficient highly diastereoselective synthesis of 1,8a-dihydro-7H-imidazo[2,1-b][1,3]oxazines, Tetrahedron 62 (2006) 3435-3438.
30. [30]
  [30] I. Yavari, A. Mirzaei, Z. Hossaini, S. Souri, Diastereoselective synthesis of fused[1,3]oxazines from ethyl pyruvate, activated acetylenes and N-heterocycles, Mol. Divers. 14 (2010) 343-347.
31. [31]
  [31] I. Yavari, Z. Hossaini, S. Souri, S. Seyfi, Diastereoselective synthesis of fused[1,3]thiazolo[1,3]oxazins and [1,3]oxazino[2,3-b][1,3]benzothiazoles, Mol. Divers. 13 (2009) 439-443.
32. [32]
  [32] I. Yavari, Z. Hossaini, M. Sabbaghan, M. Ghazanfarpour-Darjani, Reaction of Nheterocycles with acetylenedicarboxylates in the presence of N-alkylisatins or ninhydrin. Efficient synthesis of spiro compounds, Monatsh. Chem. 138 (2007) 677-681.
33. [33]
  [33] I. Yavari, N. Hosseini, L. Moradi, An efficient synthesis of 2-cyano-2-phenyl-2, 11b-dihydro-[1,3]oxazino[2,3-a]isoquinolines by reaction of isoquinoline with electron-deficient acetylenes in the presence of benzoylcyanide, Monatsh. Chem. 139 (2008) 953-956.
34. [34]
  [34] M.B. Teimouri, T. Abbasi, S. Ahmadian, M.R. Poor Heravi, R. Bazhrang, An efficient three-component protocol for the synthesis of novel spiro-oxazinobarbiturates, Tetrahedron 65 (2009) 8120-8124.
35. [35]
  [35] A.A. Esmaeili, H. Vesalipoor, R. Hosseinabadi, et al., An efficient diastereoselective synthesis of spiro pyrido[2,1-b][1,3]oxazines via a novel pyridine-based threecomponent reaction, Tetrahedron Lett. 52 (2011) 4865-4867.
36. [36]
  [36] M. Mohseni, H. Norouzi, J. Hamedi, A. Roohi, Screening of antibacterial producing actinomycetes from sediments of the Caspian Sea, Int. J. Mol. Cell Med. 2 (2013) 64-71.
37. [37]
  [37] S. Asghari, S. Ramezani, M. Mohseni, Synthesis and antibacterial activity of ethyl 2-amino-6-methyl-5-oxo-4-aryl-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carboxylate, Chin. Chem. Lett. 25 (2014) 431-434.
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