European Journal of Chemistry 2015, 6(2), 163-168 | doi: https://doi.org/10.5155/eurjchem.6.2.163-168.1224 | Get rights and content






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Synthesis of novel cyanoacetamides derivatives and their urease inhibition studies


Abdul Rauf (1) , Khalil Ahmed Nazish (2) , Faiz-ul Hassan Nasim (3) , Asma Yaqoob (4) , Ashfaq Mahmood Qureshi (5,*)

(1) Department of Chemistry, The Islamia University of Bahawalpur, Bahawalpur, 63100, Pakistan
(2) Department of Chemistry, The Islamia University of Bahawalpur, Bahawalpur, 63100, Pakistan
(3) Department of Chemistry, The Islamia University of Bahawalpur, Bahawalpur, 63100, Pakistan
(4) Department of Chemistry, The Islamia University of Bahawalpur, Bahawalpur, 63100, Pakistan
(5) Institute of Chemical Sciences, Bahauddin Zakariya University, Multan, 60800, Pakistan
(*) Corresponding Author

Received: 19 Nov 2014 | Revised: 06 Jan 2015 | Accepted: 18 Jan 2015 | Published: 30 Jun 2015 | Issue Date: June 2015

Abstract


The present study reports a convenient approach for the synthesis of cyanoacetamide based derivatives (7-27) via two-step process involving Knoevenagel reaction, followed by three component reaction to avail desired compounds. All the synthesized compounds were obtained in good to excellent yield and extensively characterized employing 1H NMR, 13C NMR, mass spectrometry and physical parameters. Further, these compounds were screened for urease inhibition. All of the synthesized compounds exhibited good to excellent urease activity notably compound 15 and 19 showed excellent urease inhibition activity with IC50 value ~17.34 μg/mL and 36.75 μg/mL in comparison to thiourea (used as standard) having IC50 value ~27.5 μg/mL.


Keywords


Furan; Thiophene; Cyanoactamides; Urease inhibition activity; Knoevenagel condensation; N,N-Dimethyl barbituric acid

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DOI: 10.5155/eurjchem.6.2.163-168.1224

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References

[1]. Fadda, A. A.; Bondock, S.; Rabie, R.; Etman, H. A. Turk. J. Chem. 2008, 32, 259-286.

[2]. Shishoo, C. J.; Devani, M. B.; Ananthan, S.; Jain, K. S.; Bhadti, V. S.; Mohan; S.; Patel, L. J. Indian J. Chem. B 1989, 28, 1039-1047.

[3]. Hazra, K.; Saravanan, J.; Mohan, S.Asian J. Chem. 2007, 19, 3541-3544.

[4]. Zhuravel, I. O.; Kovalenko, S. M.; Ivachtchenko, A. V.; Balakin, K. V.; Kazmirchuk, V. Bioorg. Med. Chem. Lett. 2005, 15(24), 5483-5487.
http://dx.doi.org/10.1016/j.bmcl.2005.08.081

[5]. Geissler, A. E.; Huppatz, J. L.; Phillips, J. N. Pestic. Sci. 1980, 11, 432-438.
http://dx.doi.org/10.1002/ps.2780110410

[6]. Shams H. Z., Elkholy, Y. M.; Azzam, R. A.; Mohareb, R. M. Phosphorus Sulfur 1999, 155, 215-233.
http://dx.doi.org/10.1080/10426509908044984

[7]. Ismail, M. M. F.; Ammar, Y. A.; El-Zahaby, H. A. S.; Eisa, S. I.; Barakat, S. E. Arch. Pharm. Life Sci. 2007, 340, 476-482.
http://dx.doi.org/10.1002/ardp.200600197

[8]. Litvinov, V. P. Russ. Chem. Rev. 1999, 68, 737-763.
http://dx.doi.org/10.1070/RC1999v068n09ABEH000533

[9]. Ghani, U. N.; Atta-ur-Rahman; Choudhary, M. I.; Ullah, N.; James, M. N. J. Mol. Biol. 2001, 314(3), 519-525.
http://dx.doi.org/10.1006/jmbi.2001.5148

[10]. Qureshi, A. M.; Qadir, M.; Rauf, A.; Idrees, M.; Mumtaz, S.; Najam-ul-Haq, M.; Aziz-ur-rehman; Ismail, M.; Athar, M.; Khushal, R.; Riaz, S.; Bokhari, H. Lett. Drug Des. Discov. 2011, 8(10), 980-987.

[11]. Halliwell, B.; Gutteridge, J. M. Meth. Enzymol. 1990, 186, 1-85.

[12]. Rauf, A.; Liaqat, S.; Qureshi, A. M.; Yaqub, M.; Aziz-ur-Rehman, Hassan, M. U.; Chohan, Z. H.; Nasim, F. U. H.; Hadda, T. B. J. Med. Chem. Res. 2012, 21, 60-74.
http://dx.doi.org/10.1007/s00044-010-9491-2

[13]. Shaukat, A.; Rasool, N.; Ullah, A.; Nasim, F. H.; Yaqoob, A.; Zubair, M.; Rashid, U.; Riaz, M. Molecules, 2013, 18, 14711-14725.
http://dx.doi.org/10.3390/molecules181214711

[14]. Garrat, D. C. Quantitative analysis of drugs. 3rd edition, Chapman & Hall Ltd, 1964.
http://dx.doi.org/10.1007/978-1-4613-3380-7_1

[15]. Qureshi, A. M.; Saira, M.; Rauf, A.; Ashraf, M.; Nasar, R.; Zahid, H. C. J. Enzym. Inhib. Med. Chem. 2015, 30, 119-125.
http://dx.doi.org/10.3109/14756366.2014.895717

[16]. Rauf, A.; Ahmed. F.; Qureshi, A. M.; Aziz-ur-Rehman; Khan, A.; Qadir, M. I.; Choudhary, M. I.; Chohan, Z. H.; Youssoufi, M. H.; Hadda T. B. J. Chin. Chem. Soc. 2011, 58, 528-537.
http://dx.doi.org/10.1002/jccs.201190017

[17]. Upadhyay, L. S. B. Ind. J. BioTech. 2012, 11, 381-388.

How to cite


Rauf, A.; Nazish, K.; Nasim, F.; Yaqoob, A.; Qureshi, A. Eur. J. Chem. 2015, 6(2), 163-168. doi:10.5155/eurjchem.6.2.163-168.1224
Rauf, A.; Nazish, K.; Nasim, F.; Yaqoob, A.; Qureshi, A. Synthesis of novel cyanoacetamides derivatives and their urease inhibition studies. Eur. J. Chem. 2015, 6(2), 163-168. doi:10.5155/eurjchem.6.2.163-168.1224
Rauf, A., Nazish, K., Nasim, F., Yaqoob, A., & Qureshi, A. (2015). Synthesis of novel cyanoacetamides derivatives and their urease inhibition studies. European Journal of Chemistry, 6(2), 163-168. doi:10.5155/eurjchem.6.2.163-168.1224
Rauf, Abdul, Khalil Ahmed Nazish, Faiz-ul Hassan Nasim, Asma Yaqoob, & Ashfaq Mahmood Qureshi. "Synthesis of novel cyanoacetamides derivatives and their urease inhibition studies." European Journal of Chemistry [Online], 6.2 (2015): 163-168. Web. 25 Oct. 2020
Rauf, Abdul, Nazish, Khalil, Nasim, Faiz-ul, Yaqoob, Asma, AND Qureshi, Ashfaq. "Synthesis of novel cyanoacetamides derivatives and their urease inhibition studies" European Journal of Chemistry [Online], Volume 6 Number 2 (30 June 2015)

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DOI Link: https://doi.org/10.5155/eurjchem.6.2.163-168.1224

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