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Abstract
Enaminonitrile derivative, 6-amino-4-(2-chloro-5-nitrophenyl)-3-methyl-1,4-dihydropyrano[2,3- c]pyrazole-5-carbonitrile (1) was synthesized. This compound was utilized as a building block for the synthesis of new 3-methyl pyrazolopyran moiety incorporated with different heterocycles involving pyrimidinone (2), oxazinone (4a,b) and iminopyrimdine (8), in addition to novel derivatives including diacetyl derivative (5), benzoyl derivative (6), carbamodithioic acid (10) and urea derivative (13). Spectral techniques, FTIR, 1H NMR and Mass spectroscopy and elemental analysis were used to characterize the synthesized compounds. Screening and evaluation of these products as antimicrobial agents showed that the derivatives 5, 6, 10 and 13 possess a potent activity.
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References
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References
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M. El-Far, G.A. Elmegeed, E.F. Eskander, H.M. Rady and M.A. Tantawy, Eur. J. Med. Chem., 44, 3936 (2009); https://doi.org/10.1016/j.ejmech.2009.04.020.
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R. Maggi, R. Ballini, G. Sartori and R. Sartorio, Tetrahedron Lett., 45, 2297 (2004); https://doi.org/10.1016/j.tetlet.2004.01.115.
A.O. Abdelhamid and M.A.M. Afifi, J. Adv. Res., 1, 137 (2010); https://doi.org/10.1016/j.jare.2010.03.005.
A.A. Al-Amiery, R.I. Al-Bayati, F.M. Saed, W.B. Ali, A.A.H. Kadhum and A.B. Mohamad, Molecules, 17, 10377 (2012); https://doi.org/10.3390/molecules170910377.
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A.A. Fayed, H.M. Hosni, E.M. Flefel and A.E.E. Amr, World J. Chem., 4, 58 (2009).
S.M. Sondhi, N. Singh, M. Johar and A. Kumar, Bioorg. Med. Chem., 13, 6158 (2005); https://doi.org/10.1016/j.bmc.2005.06.063.
A.A. Abu-Hashem, M.F. El-Shehry and F.A. Badria, Acta Pharm., 60, 311 (2010); https://doi.org/10.2478/v10007-010-0027-6.
J. Svetlik, L. Veizerova, T. Liptaj and J. Kubista, ARKIVOC, 79 (2009); https://doi.org/10.3998/ark.5550190.0010.a09.
O.A. Fathalla, I.F. Zeid, M.E. Haiba, A.M. Soliman, S.I. Abd-Elmoez and W.S. Serwy, World J. Chem., 4, 127 (2009).
S.A. El-Assiery, G.H. Sayed and A. Fouda, Acta Pharm., 54, 143 (2004).
M. Li, S.W. Wang, L.R. Wen, W.Y. Qi and H.Z. Yang, Chin. J. Struct. Chem., 24, 64 (2005).
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S.I. Alqasoumi, A.M. AlTaweel, A.M. Alafeefy, E. Noaman and M.M. Ghorab, Eur. J. Med. Chem., 45, 738 (2010); https://doi.org/10.1016/j.ejmech.2009.11.021.
A.D. Broom, J.L. Shim and G.L. Anderson, J. Org. Chem., 41, 1095 (1976); https://doi.org/10.1021/jo00869a003.
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M.M. Ghorab and A.Y. Hassan, Phosphorus Sulfur Silicon Rel. Elem., 141, 251 (1998); https://doi.org/10.1080/10426509808033737.
P. Sharma, N. Rane and V.K. Gurram, Bioorg. Med. Chem. Lett., 14, 4185 (2004); https://doi.org/10.1016/j.bmcl.2004.06.014.
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M.M. Hanna, Eur. J. Med. Chem., 55, 12 (2012); https://doi.org/10.1016/j.ejmech.2012.06.048.
S.V. Shinde, W.N. Jadhav and N.N. Karade, Orient. J. Chem., 26, 307 (2010).
R.B. Lichtner, G. Hutchinson and K. Hellmann, Eur. J. Cancer Clin. Oncol., 25, 945 (1989); https://doi.org/10.1016/0277-5379(89)90152-1.
J.I. DeGraw, P.H. Christie, W.T. Colwell and F.M. Sirotnak, J. Med. Chem., 35, 320 (1992); https://doi.org/10.1021/jm00080a017.
H.D. Thomas, K. Saravanan, L.Z. Wang, M.J. Lin, J.S. Northen, H. Barlow, M. Barton, D.R. Newell, R.J. Griffin, B.T. Golding and N.J. Curtin, Mol. Cancer Ther., 8, 1828 (2009); https://doi.org/10.1158/1535-7163.MCT-08-1208.
N.C. Petal and A.G. Mehta, Asian J. Chem., 13, 1385 (2001).
B.S. Holla, M. Mahalinga, M.S. Karthikeyan, P.M. Akberali and N.S. Shetty, Bioorg. Med. Chem., 14, 2040 (2006); https://doi.org/10.1016/j.bmc.2005.10.053.
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N.M. Yousif, F.A. Gad and H.H. Sayed, Egypt. J. Chem., 35, 101 (1992).
N.M. Yousif, F.A. Gad and H.H. Sayed, Egypt. J. Pharm. Sci., 37, 145 (1996).
H.H. Sayed, Indian J. Chem., 37B, 1054 (1998).
H.H. Sayed and F.A. Fahmy, Egypt. J. Chem., 44, 365 (2001).
A.E. Rashad, H.H. Sayed, A.H. Shamroukh and H.M. Awad, Phosphorus Sulfur Rel. Elem., 180, 2767 (2005); https://doi.org/10.1080/104265090968118.
F.M.E. Abdel-Megeid, N.A. Hassan, M.A. Zahran and A.E. Rashad, Sulfur Lett., 21, 269 (1998).
A. El-Ziaty, A. Abdalh, A. Hamed, S. Shiba and A. Abdullha, Eur. J. Chem., 3, 65 (2012); https://doi.org/10.5155/eurjchem.3.1.65-70.518.
A.K. El-Ziaty and S.A. Shiba, Synth. Commun., 37, 4043 (2007); https://doi.org/10.1080/00397910701575491.
W.S.I. Abou-Elmagd, A.K. EL-Ziaty and A.A. Abdalha, Heterocycl. Commun., 21, 179 (2015); https://doi.org/10.1515/hc-2015-0008.
A.K. Elziaty, O.E.A. Mostafa, E.A. El- Bordany, M. Nabil and H.M.F. Madkour, Int. J. Sci. Eng. Res., 5, 727 (2014).
M.R. Mahmoud, S.A. Shiba, A.K. El-Ziaty, F.S.M. Abu El-Azm and M.F. Ismail, Synth. Commun., 44, 1094 (2014); https://doi.org/10.1080/00397911.2013.846381.
A.K. El-Ziaty, A.M. Hussein and M.R. Mahmoud, World Appl. Sci. J., 17, 101 (2012).
M.M. Elshahawi, A.K. EL-Ziaty, J.M. Morsy and A.F. Aly, J. Heterocycl. Chem., 53, 1443 (2016); https://doi.org/10.1002/jhet.2445.
M.M. El-Shahawi and A.K. El-Ziaty, J. Chem., Article ID 5610707 (2017); https://doi.org/10.1155/2017/5610707.
A.K. El-Ziaty, G. Bassioni, A.M.A. Hassan, H.A. Derbala and M.S. Abdel-Aziz, , J. Chem., Article ID 5286462 (2016); https://doi.org/10.1155/2016/5286462.