Synthesis of Bioactive Heterocycles from 6-Amino-4-(2-chloro-5-nitrophenyl)- 3-methyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile

A.K. Elziaty; G. Bassioni; A.M.A. Hassan; H. A. Derbala

doi:10.14233/ajomc.2018.AJOMC-P104

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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.

Keywords

Enaminonitrile Pyranopyrazole Pyrimidinone Oxazinone Antimicrobial agents

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Elziaty, A., Bassioni, G., Hassan, A., & A. Derbala, H. (2018). Synthesis of Bioactive Heterocycles from 6-Amino-4-(2-chloro-5-nitrophenyl)- 3-methyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile. Asian Journal of Organic & Medicinal Chemistry, 3(1), 23–28. https://doi.org/10.14233/ajomc.2018.AJOMC-P104

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References

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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).
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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.

References

A. Goel and F.V. Singh, Tetrahedron Lett., 46, 5585 (2005); https://doi.org/10.1016/j.tetlet.2005.06.034.

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.

P.V. Pasternak, B.B. Averkiev, M.Y. Antipin, A.S. Peregudov and N.D. Chkanikov, J. Fluor. Chem., 125, 1853 (2004); https://doi.org/10.1016/j.jfluchem.2004.06.008.

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.

A.B.A. El-Gazzar, M.M. El-Enany and M.N. Mahmoud, Bioorg. Med. Chem., 16, 3261 (2008); https://doi.org/10.1016/j.bmc.2007.12.012.

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).

J. Wannberg, D. Dallinger, C.O. Kappe and M.J. Larhed, Comb. Chem., 7, 574 (2005); https://doi.org/10.1021/cc049816c.

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.

A.A. Joshi and C.L. Viswanathan, Antiinfect. Agents Med. Chem., 5, 105 (2006); https://doi.org/10.2174/187152106774755626.

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.

A.B.A. ElGazzar, H.N. Hafez and G.A.M. Nawwar, Eur. J. Med. Chem., 44, 1427 (2009); https://doi.org/10.1016/j.ejmech.2008.09.030.

J.P. De La Cruz, A. Moreno, F. Mérida, J. Carcia-Campos and F.S. de la Cuesta, Pharmacol. Toxicol., 75, 250 (1994); https://doi.org/10.1111/j.1600-0773.1994.tb00356.x.

R. Gupta, A. Jain, R. Joshi and M. Jain, Bull. Korean Chem. Soc., 32, 899 (2011); https://doi.org/10.5012/bkcs.2011.32.3.899.

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.

S. Calus, E. Gondek, A. Danel, B. Jarosz, M. Pokladko and A.V. Kityk, Mater. Lett., 61, 3292 (2007); https://doi.org/10.1016/j.matlet.2006.11.055.

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.

Synthesis of Bioactive Heterocycles from 6-Amino-4-(2-chloro-5-nitrophenyl)- 3-methyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile

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