Synthesis and Characterization of Some New Bis-Chalconesand Their Transformation to Bis-Thiocarbamoyl-2- Pyrazoline Derivatives
Keywords:
Microwave, Grinding, Chalcone, Thiosemicarbazide, PyrazolineAbstract
The starting materials alkoxy and benzyloxyacetophenones (1a-j, 2 and 3) have been prepared on the basis of Williamson synthesis of ether. The prepared and the available starting materials were reacted with terphthalaldehyde using green methods, Ultrasound , Microwave and solvent-free grinding method to give anew series of bis- chalcones (4a-s).The prepared bis- chalcones were subjected to react with thiosemicarbazide according to the Michael addition reaction to afford new biologically active bis-pyrazolinedeivatives(5a-s). The structure of the synthesized compounds were characterized by spectral methods: FT-IR, 1H-nmr, 13C-nmr andMass spectrometry.
References
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Sahu, S.K., Banerjee, M. A., Samantray, C.B. and Azam M.A.(2008). Synthesis, Analgesic, Anti-inflammatory and Antimicrobial Activities of Some Novel Pyrazoline Derivatives, Tropical Journal of Pharmaceutical Research., 7 (2), 961-968.
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Seebacher, W., Michl, G., Belaj, F., Brun, R., Saf, R. Weis, R. (2003). One-pot syntheses of 2-pyrazoline derivative.,Tetrahedron 59, 2811-2819.
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Vanstone, A.E., Mail G.K., & Lynn, K.(1989). U.S. Patent Re.33,109-10.
Azarifar, D., and Shaebanzadeh, M. (2002). Synthesis and Characterization of New 3,5-DinaphthylSubstituted 2-Pyrazolines and Study of Their Antimicrobial Activity, molecules, 7, 885-895
Azizur, R. M.d., Anees, A. S.(2010). Pyrazoline Derivatives: A Worthy Insight into the Recent Advances and Potential Pharmacological Activities, International Journal of Pharmaceutical Sciences and Drug Research. 2(3): 165-175.
Asha B., Mohammad A., Amir A. (2006). Synthesis and antiamoebic activity of new 1-N-substituted thiocarbamoyl-3,5-diphenyl-2-pyrazoline derivatives. , European Journal of Medicinal Chemistry 41, 63-70.
Asha, B., Mohammad, A., Amir A. (2007). Syntheses, characterization and in vitro antiamoebic activity of new Pd(II) complexes with 1-N-substituted , European Journal of Medicinal Chemistry 42, 544-551
Buckingham, J. E. (1994). Dictionary of Natural Products, Champan and Hall Chemical data base, CRC press.
Biswajit, C. D., G. Mariappan, S. S., Debjit, B, C.(2010). Anthelmintic and anti-microbial activity of some novel chalcone derivatives, J. Chem. Pharm. Res., 2(1),113-120.
Charles D. H., Babajide O. O., James N. S. (1987). Angoluvarin, an antimicrobial dihydrochalcone from Uvariaangolensis, J. Org. Chem., 52 (23), 5286–5288.
derivatives from 2-chloro-6-ethoxy-4-acetylpyridine, MonatsheftefürChemie - Chemical Monthly, 139, 11, 1409-1415.
Goda F. E., Maorouf A. R., and EL-Bendary, E. R., (2003). Synthesis and Antimicrobial evaluation of new Isoxazolyl and pyrazole Derivatives, Saudi Pharmaceutical Journal, 11, 3, 111-117.
Guofeng, C., Jitai, L., Huiyun D., &Tongshuang, L., C.J.I. 6 (1), 6-8. (2004). Improved ultrasound-induced synthesis of 1,5-diaryl-1,4-pentadien-3-ones
Gareth W. V. Cave & Colin L. Raston. (2001). Efficient synthesis of pyridines via a sequential solvent less aldol condensation and Michael addition, J. Chem. Soc., Perkin Trans. 1, 3258-3264.
Hsieh, H.K., Lee, T.H., Wang, J.P., wang J.J. & Lin, C.N.(1998). Synthesis and anti-inflammatory effect of chalcones and related compounds. Pharmacuetical Research, 15(1), 39-46.
Katritzky, A. R. (2005). Advances in Heterocyclic Chemistry , Academic Press / Elsevier Science & Technology Books.
Li, R., Kenyon, G. L., and Cohen, F. E.(1995). In Vitro Antimalarial Activity of Chalcones and Their Derivatives, J. Med. Chem., 38, 5031-5037.
Mirjalil, B. F. and Zaghaghi, Z. (2008). An Eco-friendly Alternative for the Stereo Regio and Chemo selective Claisen-Schmidt Condensation.J. Chin. chem. Soc., 55, 3, 694-699.
Mei Liu,aPraponWilairat,b Simon L. Croft,Agnes Lay-ChooTand and Mei-Lin Go, Structure– Activity Relationships of Antileishmanial and Antimalarial Chalcones, Bioorganic & Medicinal Chemistry 11 (2003) 2729–2738.
Miranda, C.L., Stevens, J.F., Ivanov, V., McCall, M., Frei, B. Deinzer, M.L., Buhler, D.R.(2000). Antioxidant and prooxidant actions of prenylated and nonprenylated chalcones and flavanones in vitro. J Agric Food Chem. 48(9),3876-3884.
Mao, S. C., Rong, S. L., George K. (2000). A Solid Phase Synthesis of Chalcones by Claisen- Schmidt Condensations, Chinese Chemical Letters., 11, 10, 851−854.
Nielsen, S.F., Christensen, S.B., Cruciani, G., Kharazmi, A.(1998). Liljefors TAntileishmanial chalcones: statistical design, synthesis, and three-dimensional quantitative structure-activity relationship analysis., J Med Chem. 19;41(24):4819-32.
1920: Nada M. A., Hamdi M. H., Nadia G. K., and Omar A. M.(2008). Synthesis and Biological Activity of Some New Pyrazoline and Pyrrolo[3,4-c]pyrazole-4,6-dione Derivatives: Reaction of Nitrilimines with Some Dipolarophiles. Molecules , 13, 1011-1024.
Otera, J. (2000). Modern Carbonyl Chemistry, WILEY-VCH.
Ozdemir, A., Turan-Zitouni, G., Kaplancikli, Z.A, Revia,l G., Demirci, F., Işcan G. (2010). Preparation of some pyrazoline derivatives and evaluation of their antifungal activities.J Enzyme Inhib Med Chem. 25(4), 565-571.
Palaska, E., Aytemir,M., Uzbay I.T. &Erol D. (2001). Synthesis and antidepressant activities of some 3,5- diphenyl-2-pyrazolines. Eur. J. Med. Chem., 36, 539–543.
Sayed A. (2004). Synthesis, antibacterial and antifungal activity of some derivatives of 2-phenyl-chromen-4-one, J. Chem. Sci., 116, 6, 325–331.
Soon S. L., Hye-Sook K., and Dong-Ung L. (2007). In vitro Antimalarial Activity of Flavonoids and Chalcones, Bull. Korean Chem. Soc., 28, 12, 2495-2497
Sahu, S.K., Banerjee, M. A., Samantray, C.B. and Azam M.A.(2008). Synthesis, Analgesic, Anti-inflammatory and Antimicrobial Activities of Some Novel Pyrazoline Derivatives, Tropical Journal of Pharmaceutical Research., 7 (2), 961-968.
Stuart B. (2004). Infrared Spectroscopy, Fundamentals & Applications John Wiley &Sons , Ltd.
Seebacher, W., Michl, G., Belaj, F., Brun, R., Saf, R. Weis, R. (2003). One-pot syntheses of 2-pyrazoline derivative.,Tetrahedron 59, 2811-2819.
Viana, G S., Bandeira, M. A., and Matos, F.(2003). J.Analgesic and antiinflammatory effects of chalcones isolated from MyracrodruonurundeuvaallemãoPhytomedicine.,10(2-3),189-195.
Vanstone, A.E., Mail G.K., & Lynn, K.(1989). U.S. Patent Re.33,109-10.
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Published
2013-06-30
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Hawaiz, F. E., Hussein, F. H., & Azeez, H. J. (2013). Synthesis and Characterization of Some New Bis-Chalconesand Their Transformation to Bis-Thiocarbamoyl-2- Pyrazoline Derivatives. Science Journal of University of Zakho, 1(1), 210–219. Retrieved from https://sjuoz.uoz.edu.krd/index.php/sjuoz/article/view/68
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