29May 2017

MICROWAVE ASSISTED PICTET-SPENGLER SYNTHESIS OF SOME TETRAHYDROISOQUINOLINE DERIVATIVES AND THEIR BIOLOGIAL EFFICACY STUDIES.

  • Assistant Professor and Head, Department of Chemistry, M. B. Patel College, Deori, 441901(M.S.), India.
  • Associate Professor and Head, Department of Chemistry, Bhawabhuti. College, Amgaon, 441902(M.S.), India.
  • Associate Professor, Govt. Vidarbha Institute of Science and Humanities, Amravati, 444604(M.S.), India.
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In the present research article, a one pot synthesis of novel 1,2,3,4-tetrahydro-6,7-dimethoxy-1-(substitutedphenyl)isoquinoline(THIQ) derivatives using 2-(3,4-dimethoxy)phenylethylamine, substituted benzaldehyde with toluene in tetrahydrofuran(THF) under microwave condition is reported. The structures of the newly synthesised compounds were confirmed using modern analytical IR, NMR and MS techniques. The synthesized THIQ derivatives were screened for antibacterial activities against gram positive and gram negative bacteria. The biological efficacies of the synthesized derivatives were investigated in the form of zone of inhibition (mm) against E. coli, S. aureus and P. aeruginosa. Few of the derivatives have been found to possess significant antibacterial activities and can have potential applications in pharmacological/medical science.

  1. Hoogerwerff, S.; van Dorp, W. A., Recl. Trav. Chim. Pays-Bas, (1885) 4, 125.
  2. Hoogerwerff, S.; van Dorp, W. A., Recl. Trav. Chim. Pays-Bas, (1885) 4, 285.
  3. Maske, R. H. F., In The Alkaloids. Chemistry and Biology, Manske, R. H. F., Ed.; Academic: New
  4. York, (1960); Vol. 7, p 423.
  5. Stanek, J., In The Alkaloids. Chemistry and Biology, Manske, R. H. F., Ed.; Academic: New York,
  6. (1960); Vol. 7, p 433.
  7. Kulka, M., In The Alkaloids. Chemistry and Biology, Manske, R. H. F., Ed.; Academic: New York, (1960); Vol. 7, p 439.
  8. Lundstrom, J., In The Alkaloids. Chemistry and Biology, Brossi, A., Ed.; Academic: New York, (1983);Vol. 21, p 255.
  9. Kametani, T., The Chemistry of Isoquinoline Alkaloids, Elsevier: Amsterdam, (1969).
  10. Shamma, M., The Isoquinoline Alkaloids, Academic: New York, (1972).
  11. Philippson, J. D., The Chemistry and Pharmacology of Isoquinoline Alkaloids, Springer: Heidelberg,(1985).
  12. Bischler, A.; Napieralski, B. Dtsch. Chem. Ges. (1893), 26, 1903?1908.
  13. Bergstrom, F. W. Rev. (1944), 35, 77?277.
(a) Whaley, W. M.; Govindachari, T. R. Org. React. (1951), 6, 151; for superacids approach, see:??????? (b) Yokoyama, A.;Ohwada, T.; Shudo, K. J. Org. Chem. (1999), 64, 611. (a) Kametani, T.; Fukumoto, K.; Agui, H.; Yagi, H.; Kigasawa, K.; Sugahara, H.; Hiiragi, M.;?????????? Hayasaka, T.; Ishimaru, H. J. Chem. Soc. (C) (1968), 112; (b) Kametani, T.; Fukumoto, K. Heterocycles (1975), 3, 311; (c) Bates, H. A. J. Org. Chem. (1981), 46, 4931.
  1. Pal, B.; Jaisankar, P.; Giri, V. S. Synth. Commun. (2003), 33, 2339?2348.
  2. Mesangeau, C.; Yous, S.; Peres, B.; Lesieur, D.; Besson, T. Tetrahedron Lett. (2005), 46, 2465?2468.
  3. Yen, Y.-H.; Chu, Y.-H. Tetrahedron Lett. (2004), 45, 8137?8140.
  4. Kuo, F.-M.; Tseng, M.-C.; Yen, Y.-H.; Chu, Y.-H. Tetrahedron (2004), 60, 12075?12084.
  5. Campiglia, P.; Gomez-Monterrey, I.; Lama, T.; Novellino, E.; Grieco, P. Diversity (2004), 8, 427?430.
  6. Pal, B.; Jaisankar, P.; Giri, V. S. Commun. (2003), 33, 2339?2348.
  7. Gitto, R.; Ferro, S.; Agnello, S.; De Luca, L.; De Sarro, G.; Russo, E.; Vullo, D.; Supuran, C. T.; Chimirri, Bioorg. Med. Chem. (2009), 17, 3659?3664.
  8. Emelia Awuah and Alfredo Capretta Org. Chem. (2010), 75, 5627?5634

[Sachin S. Chourasia, Pralhad K. Rahangdale and Farhin Inam. (2017); MICROWAVE ASSISTED PICTET-SPENGLER SYNTHESIS OF SOME TETRAHYDROISOQUINOLINE DERIVATIVES AND THEIR BIOLOGIAL EFFICACY STUDIES. Int. J. of Adv. Res. 5 (May). 1789-1793] (ISSN 2320-5407). www.journalijar.com

Dr.P.K.Rahangdale
Ex-chairman, board of studies in chemistry, RTM, Nagpur University, Nagpur

DOI:

Article DOI: 10.21474/IJAR01/4310      
DOI URL: https://dx.doi.org/10.21474/IJAR01/4310

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