Synthesis and Properties of Some N-(2,3-Dihydrophthalazin-5-yl)amidrazones Incorporating Piperazines and Related Congeners

Banan H. Al-Rawashdeh; Mustafa M. El-Abadelah

doi:10.14233/ajchem.2017.20271

Issue

Vol. 29 No. 3 (2017): Vol 29 Issue 3

Issue Published : December 30, 2016

This work is licensed under a Creative Commons Attribution 4.0 International License.

Synthesis and Properties of Some N-(2,3-Dihydrophthalazin-5-yl)amidrazones Incorporating Piperazines and Related Congeners

https://doi.org/10.14233/ajchem.2017.20271

Banan H. Al-Rawashdeh

Chemistry Department, Faculty of Science, The University of Jordan, Amman 11942, Jordan

Mustafa M. El-Abadelah

Chemistry Department, Faculty of Science, The University of Jordan, Amman 11942, Jordan

Corresponding Author(s) : Mustafa M. El-Abadelah

mustelab@ju.edu.jo

Asian Journal of Chemistry, Vol. 29 No. 3 (2017): Vol 29 Issue 3
Article Published : December 30, 2016

Abstract

A new N-(phthalazin-5-yl)hydrazonoyl chloride derivative (2) is made accessible from luminol via the Japp-Klingemann reaction. In presence of triethyl amine, compound 2 reacted with N-substituted piperazines and related sec-amine congeners to deliver the respective set of new N-(phthalazin-5-yl)amidrazones (4a-h) in fair yield. The chemical structures of the newly synthesized compounds were confirmed by ¹H NMR, ¹³C NMR and ESI-HRMS spectral data. However, the amidrazones (4a-e) were found to display weak to moderate activity against breast cancer cell line (MCF-7) with MIC₅₀ » 25-100 μM/mL.

Keywords

Luminol Hydrazonoyl chloride N-(Substituted)piperazines N-(Pthalazin-5-yl)amidrazones

Al-Rawashdeh, B. H., & El-Abadelah, M. M. (2016). Synthesis and Properties of Some N-(2,3-Dihydrophthalazin-5-yl)amidrazones Incorporating Piperazines and Related Congeners. Asian Journal of Chemistry, 29(3), 605–608. https://doi.org/10.14233/ajchem.2017.20271

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References

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G.C. Barrett, M.M. El-Abadelah and M.K. Hargreaves, J. Chem. Soc. C, 1986 (1970).
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References

H.O. Albrecht, Z. Phys. Chem., 136, 321 (1928).

D. John and B. Robert, Handbook of Optoelectronics, vol. 1, pp. 1415- 1416 (2006).

P. Razvan, H. Gheorghe and U.P.B., Sci. Bull., Series B, 75, 23 (2013).

X. Yang, Y. Guo and A. Wang, Anal. Chim. Acta, 666, 91 (2010).

W. Specht, Angew. Chem., 50, 155 (1937).

V. Patwardhan, Chem. Ind. Digest, 23, 62 (2010).

H.H. Yoshida, R. Nakao, H. Nohta and M. Yamaguchi, Dyes Pigments, 47, 239 (2000).

R. Berthet, A. Zerroukhi, G. Brun, T. Zecheru and C. Cincu, Rev. Roum. Chim., 52, 473 (2007).

T.E. Yeshion, 6th Biolumin. Chemilumin. Proc. Int. Symp., pp. 379-84 (1991).

Y. Iglesias, C. Fente, B.I. Vazquez, C. Franco, A. Cepeda and S. Mayo, Anal. Chim. Acta, 468, 43 (2002).

A. Khalaj, N. Adibpour, A.R. Shahverdi and M. Daneshtalab, Eur. J. Med. Chem., 39, 699 (2004).

C.L.E. Broekkamp, D. Leysen, B.W.M.M. Peeters and R.M. Pinder, J. Med. Chem., 38, 4615 (1995).

H. Naito, S. Ohsuki, R. Atsumi, M. Minami, M. Mochizuki, K. Hirotani, E. Kumazawa and A. Ejima, Chem. Pharm. Bull. (Tokyo), 53, 153 (2005).

M. Ibarra, E. Hong and R. Villalobos-Molina, J. Auton. Pharmacol., 20, 139 (2000).

R.J. Abdel-Jalil, E.Q. El-Momani, M. Hamad, W. Voelter, M.S. Mubarak, B.H. Smith and D.G. Peters, Monatsh. Chem., 141, 251 (2010).

M.S. Mustafa, M.M. El-Abadelah, M.A. Zihlif, R.G. Naffa and M.S. Mubarak, Molecules, 16, 4305 (2011).

M.N. Abu-Aisheh, M.S. Mustafa, M.M. El-Abadelah, R.G. Naffa, S.I. Ismail, M.A. Zihlif, M.O. Taha and M.S. Mubarak, Eur. J. Med. Chem., 54, 65 (2012).

A.Y. Habashneh, M.M. El-Abadelah, M.A. Zihlif, A. Imraish and M.O. Taha, Arch. Pharm. Chem. Life Sci., 347, 415 (2014).

S. Musameh, S. S. Sabri, M. M. El-Abadelah, J. A. Zahra, M. M. Abadleh and W. Voelter, Lett. Org. Chem., 12, 120 (2016).

A.H. Abdullah, J.A. Zahra, M.M. El-Abadelah, S.S. Sabri, M.A. Khanfar, S.A. Matar and W. Voelter, Z. Naturforsch., 71b, 857 (2016).

R.R. Phillips, Org. React., 10, 143 (1959).

H.C. Yao and P. Resnick, J. Am. Chem. Soc., 84, 3514 (1962).

G.C. Barrett, M.M. El-Abadelah and M.K. Hargreaves, J. Chem. Soc. C, 1986 (1970).

R.N. Butler and F.L. Scott, Chem. Ind., 1216 (1970).

A.F. Hegarty, J.B. Aylward and F.L. Scott, J. Chem. Soc. C, 2587 (1967).

V.A. Galishev, V.N. Chistokletov and A.A. Petrov, Zh. Obshch. Khim., 45, 1695 (1975).

A.S. Shawali and C. Párkanyi, J. Heterocycl. Chem., 17, 833 (1980).

H.M. Hassaneen, H.A.H. Mousa, N.M. Abed and A.S. Shawali, Heterocycles, 27, 695 (1988).

T. Benincori and F. Sannicolo, J. Org. Chem., 53, 1309 (1988).

E.D. Awad, M.M. El-Abadelah, S. Matar, M.A. Zihlif, R.G. Naffa, E.Q. Al-Momani and M.S. Mubarak, Molecules, 17, 227 (2011).

Issue

Vol. 29 No. 3 (2017): Vol 29 Issue 3

Synthesis and Properties of Some N-(2,3-Dihydrophthalazin-5-yl)amidrazones Incorporating Piperazines and Related Congeners

Corresponding Author(s) : Mustafa M. El-Abadelah

Abstract

Keywords

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