Synthesis, reactions and pharmacological studies of new series of selenolo [2,3-b]tetrahydroquinoline

  • Authors

    • Magda Abdel-Lattif Magda H. Abd ellattif taif university
    • Mohamed Kobeasy Mohamed I. Kobeasy taif university
    • Shams Abdelhafez shams H. Abd elhafez taif university
  • A novel series of selenolo [2, 3-b] tetrahydroquinoline derivatives were synthesized by the reaction of NaSeH with 2-chloro-3-cyano-4-(4-methoxyphenyl)-5, 6, 7, 8-tetrahydroquinoline 2 followed by reactions with chloro acetone, chloro acetonitrile, ethyl chloroacetate and chloro acetamide to yield 9 and 11a-c respectively. Reactions of 11c with acetic anhydride, cyclohexanone and aromatic aldehyde affording derivatives 12-14 respectively. Spectroscopic (IR, 1HNMR, 13CNMR and MS) were confirmed the structure of the synthesized compounds. Compounds 5a-c, 9, 11a-c, 12, 13 and 14 were investigated for their anti-inflammatory and analgesic activities; in addition, the most active compounds were tested for their acute toxicity.

    Keywords: Tetrahydro Quinolines; Pharmacological Screening; Pyrimidoselenolo Tetrahydroquinolines; Spirocyclohaxanepyrimidoselenolo Tetrahydroquinoline.

  • References

    1. An Efficient Synthesis of Pyrazolo[3,4-b]quinolin-3-amine and Benzo[b][1,8]naphthyridine Derivatives, Yehya M. Elkholy, Molecules 2007, 12, 361-372.
    2. Reaction of 3-aminocyclohex-2-en-1-ones with arylidenemalononitriles: synthesisof N substituted 1, 4, 5, 6, 7, 8- hexahydroquinolin-5-onesLichitsky, B. V., Dudinov, A. A.; Krayushkin, M. M. Arkivoc 2001, 73-79.
    3. The synthesis of 4-aryl-1H-pyrazolo [3, 4-b] quinolines by cyclization of 4 arylidenepyrazolin-5-ones with anilinesChaczatrian, K.; Chaczatrian, G.; Danel, A.; Tomasik P. Arkivoc 2001, 63-69.
    4. An efficient synthesis of benzo[b] [1,8]naphthyridine-3-carboxylic methyl esters (pages 755–758) Nithyadevi V.; Rajendran, S. P.J. Heterocycl. Chem. 2006, 43, 755-758.
    5. Synthesis of 4-azido-3-diazo-3 H-pyrazolo [3, 4-b] quinoline from 3-amino-4-hydrazino-1 H-pyrazolo [3, 4-b] quinoline 1, W Stadlbauer, G Hojas the Chemical Society, Perkin Transactions 1, 2000 -, 3085-3087.
    6. Facile Synthesis of 5, 6, 7, 8-Tetrahydropyrimido [4, 5-b]-quinoline Derivatives Elkholy, Y. M.; Morsy, M. A. Molecules 2006, 11, 890-903.
    7. A NEW APPROACH TO THE SYNTHESIS OF BENZO[b][1,8]NAPHTHYRIDIN-I(IH)ONESVijayalakshmi, S.; Ragunath, L.; Rajendran, S. P. A, Heterocycl. Commun. 2001, 7, 177-182.
    8. Synthesis and Antimicrobial Activity of Novel Pyrazolo[3,4-b]quinoline Derivatives El-Sayed, O. A.; Aboul-Enein, H. Y. Arch. Pharm. (Weinheim) 2001, 334, 117-120. (200104)334:4<117: AID-ARDP117>3.0.CO; 2-9.
    9. Analogues of 1-(3, 10-dibromo-8-chloro-6, 11-dihydro-5H-benzo-[5, 6]-cyclohepta [1, 2-b] pyridin-11-yl)piperidine as inhibitors of farnesyl protein transferase.Wolin, R.; Wang, D., Kelly, J.; Afonso, A.; James, L.; Kirschmeier, P.; Mcphail, A. T. Bioorg. Med. Chem. Lett. 1996, 6, 195- 200.
    10. 1-substituted, 3-carboxy, 7-fluoro,8-disubstituted amino-1,4-dihydrobenzo(b)(1,8)naphthyridin-4-ones; Useful as antimicrobial agents; topical antibiotic for wounds Antoine, M.; Barreau, M.; Descon, C.; Philippe, G.; Guy, P.US Pat. 6548506, 2003
    11. An Efficient Synthesis of Pyrazolo [3, 4-b] quinolin-3-amine and Benzo [b] [1, 8] naphthyridine Derivatives YM Elkholy - Molecules, 2007.
    12. Selenium-Containing Heterocycles: Synthesis and Pharmacological Activities of Some New 4-Methylquinoline-2(1H) Selenone Derivatives (pages 240–246) Shams H. Abdel-Hafez, Mostafa A. Hussein, Arch. Pharm. Chem. Life Sci. 2008, 341, 240 – 246.
    13. Carrageenin-induced edema in hind paw of the rat as an assay for antiiflammatory drugsWinter, C.A., Risley, E.A.G.A.N. Nus Proc. Soc. Exp.Biol.111 (1962) 544-547.
    14. Acetic acid for analgesic screening Koster, R. Anderson, M. De Beer, E.J. Fed.Proc. 18 (1959) 412.
    15. Sztaricskai, F. Takacs, I.E. Pusztai, F. Szabo, G., Csipo, I., Phosphorus Sulfur,Silicon Relat. Elem. 332 (1999) 321-326.
  • Downloads

  • How to Cite

    Abdel-Lattif, M., Kobeasy, M., & Abdelhafez, S. (2014). Synthesis, reactions and pharmacological studies of new series of selenolo [2,3-b]tetrahydroquinoline. International Journal of Basic and Applied Sciences, 3(4), 433-440.