Synthesis, Crystal Structure and Cholinesterase Enzymes Inhibitory Activities of New Pyridine Alkaloid Derivative

Raza Murad Ghalib; Rokiah Hashim; Sayed Hasan Mehdi; M. Fátima C. Guedes Da Silva; Othman Sulaiman; Fiona How Ni Foong; Fumio Kawamura; Ali Jawad; Yousif Algamal; Kit-Lam Chan; Vikneswaran Murugaiyah

doi:10.14233/ajchem.2015.19102

Issue

Vol. 27 No. 11 (2015): Vol 27 Issue 11

Issue Published : July 16, 2015

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

Synthesis, Crystal Structure and Cholinesterase Enzymes Inhibitory Activities of New Pyridine Alkaloid Derivative

https://doi.org/10.14233/ajchem.2015.19102

Raza Murad Ghalib

Department of Chemistry, Faculty of Sciences and Arts-Khulais, University of Jeddah, Khulais, P.O. Box-355, Postal Code-21921, Kingdom of Saudi Arabia; Department of Chemistry, Kulliyyah of Science, International Islamic University Malaysia, Kuantan, Pahang, Malaysia

Rokiah Hashim

School of Industrial Technology, Universiti Sains Malaysia, Pulau-Pinang 11800, Malaysia

Sayed Hasan Mehdi

School of Industrial Technology, Universiti Sains Malaysia, Pulau-Pinang 11800, Malaysia

M. Fátima C. Guedes Da Silva

Centro de Química Estrutural, Complexo I, Instituto Superior Técnico, Av. Rovisco Pais, 1049-00 Lisboa, Portugal

Othman Sulaiman

School of Industrial Technology, Universiti Sains Malaysia, Pulau-Pinang 11800, Malaysia

Fiona How Ni Foong

Department of Chemistry, Kulliyyah of Science, International Islamic University Malaysia, Kuantan, Pahang, Malaysia

Fumio Kawamura

Wood Extractives Laboratory, Department of Biomass Chemistry, Forestry and Forest Products Research Institute, Tsukuba 305-8687, Japan

Ali Jawad

Department of Applied Physics, Zakir Husain College of Engineering and Technology, Aligarh Muslim University, Aligarh-202 002, India

Yousif Algamal

Department of Chemistry, Faculty of Sciences and Arts-Khulais, University of Jeddah, Khulais, P.O. Box-355, Postal Code-21921, Kingdom of Saudi Arabia

Kit-Lam Chan

Discipline of Pharmaceutical Chemistry, School of Pharmaceutical Sciences, Universiti Sains Malaysia, Pulau-Pinang 11800, Malaysia

Vikneswaran Murugaiyah

Discipline of Pharmacology, School of Pharmaceutical Sciences, Universiti Sains Malaysia, Pulau-Pinang 11800, Malaysia

Corresponding Author(s) : Raza Murad Ghalib

raza2005communications@gmail.com

Asian Journal of Chemistry, Vol. 27 No. 11 (2015): Vol 27 Issue 11
Article Published : July 16, 2015

Abstract

A new pyridine alkaloid derivative named as 2-(6-benzyl-4-oxo-5-phenyl-1,4-dihydro pyridine-3-yl)-benzoic acid ethylester (3) has been prepared by the reaction of ninhydrin with 1,3-diphenylacetone p-tosylhydrazone and the structure has been established with the help of spectral analysis and X-ray analysis. The title compound demonstrated potent inhibitory activity against butyrylcholinesterase (BChE; IC₅₀ = 4.91 μM) comparable to physostigmine (IC₅₀ = 4.72 × 10^-1 μM). However it showed moderate inhibitory activity against acetylcholinesterase (AChE; IC₅₀ = 82.00 μM)). It was BChE selective over AChE, in contrast to physostigmine, which was more AChE selective. Being a potent and selective BChE inhibitor, it may serve as a new class of drug for prevention of the progression of neurodegeneration as well for symptomatic treatment of Alzheimer patient.

Keywords

Pyridine alkaloid Acetylcholinesterase Butyrylcholinesterase

Murad Ghalib, R., Hashim, R., Hasan Mehdi, S., Fátima C. Guedes Da Silva, M., Sulaiman, O., How Ni Foong, F., … Murugaiyah, V. (2015). Synthesis, Crystal Structure and Cholinesterase Enzymes Inhibitory Activities of New Pyridine Alkaloid Derivative. Asian Journal of Chemistry, 27(11), 4092–4096. https://doi.org/10.14233/ajchem.2015.19102

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References

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N.K. Gusarova, S.F. Malysheva, L.A. Oparina, N.A. Belogorlova, A.P. Tantsyrev, L.N. Parshina, B.G. Sukhov, R.T. Tlegenov and B.A. Trofimova, ARKIVOC, 260 (2009); doi:10.3998/ark.5550190.0010.725.

A. Chaubey and S.N. Pandeya, Asian J. Pharm. Clin. Res., 4, 5 (2011).

H. Nadri, M. Pirali-Hamedani, A. Moradi, A. Sakhteman, A. Vahidi, V. Sheibani, A. Asadipour, N. Hosseinzadeh, M. Abdollahi, A. Shafiee and A. Foroumadi, DARU J. Pharm. Sci., 21, 15 (2013).

F.A. Attaby, A.M. Abdel-Fattah, L.M. Shaif and M.M. Elsayed, Afinidad, 66, 540 (2009).

V. Tougu, Curr. Med. Chem-CNS Agents, 1, 155 (2001); doi:10.2174/1568015013358536.

M.F. Lipton, C.M. Sorensen, A.C. Sadler and R.H. Shapiro, J. Organomet. Chem., 186, 155 (1980); doi:10.1016/S0022-328X(00)89863-0.

J.C. Jung, K.S. Kim and Y.H. Kim, Synth. Commun., 22, 1583 (1992); doi:10.1080/00397919208021631.

S. Cacchi, F. La-Torre and D. Misiti, Synthesis, 301 (1977); doi:10.1055/s-1977-24366.

S. Cacchi, D. Misiti and M. Felici, Synthesis, 147 (1980); doi:10.1055/s-1980-28954.

E. Rasolofonjatovo, B. Tréguier, O. Provot, A. Hamze, E. Morvan, J.D. Brion and M. Alami, Tetrahedron Lett., 52, 1036 (2011); doi:10.1016/j.tetlet.2010.12.093.

W.R. Bamford and T.S. Stevens, J. Chem. Soc., 4735 (1952); doi:10.1039/jr9520004735.

G. Rosini and G. Baccolini, J. Org. Chem., 39, 826 (1974); doi:10.1021/jo00920a017.

J.F.W. Keana, D.P. Dolata and J. Ollerenshaw, J. Org. Chem., 68, 3815 (1973); doi:10.1021/jo00961a042.

T. Ueda and T. Tsuji, NII-Electronic Library Service, 9, 71 (1961).

A.-H. García-Muñoz, M. Tomás-Gamasa, M.C. Pérez-Aguilar, E. Cuevas-Yañez and C. Valdés, Eur. J. Org. Chem., 2012, 3925 (2012); doi:10.1002/ejoc.201200647.

A. Zhou, L. Wu, D. Li, Q. Chen, X. Zhang and W. Xia, Chin. J. Chem., 30, 1862 (2012); doi:10.1002/cjoc.201200387.

SMART & SAINT Software Reference Manuals, version 4.0, Siemens Energy & Automation, Inc., Analytical Instrumentation, Madison, WI (1996).

G.M. Sheldrick, SADABS Software for Empirical Absorption Correction, University of Gottingen, Germany (1996).

SHELXTL, version 5.03, Siemens Energy & Automation, Inc., Analytical Instrumentation, Madison, WI (1996).

T. Ahmed and A.H. Gilani, Pharmacol. Biochem. Behav., 91, 554 (2009); doi:10.1016/j.pbb.2008.09.010.

M. Weinstock and E. Groner, Chem. Biol. Interact., 175, 216 (2008); doi:10.1016/j.cbi.2008.03.014.

M. Mesulam, A. Guillozet, P. Shaw and B. Quinn, Neurobiol. Dis., 9, 88 (2002); doi:10.1006/nbdi.2001.0462.

A.N. Cokugras, Turk. J. Biochem., 28, 54 (2003).

A.L. Guillozet, M.-M. Mesulam, J.F. Smiley and D.C. Mash, Ann. Neurol., 42, 909 (1997); doi:10.1002/ana.410420613.

C.G. Ballard and E.K. Perry, Acta Neurol. Taiwan, 12, 109 (2003).

N.H. Greig, T. Utsuki, D.K. Ingram, Y. Wang, G. Pepeu, C. Scali, Q.-S. Yu, J. Mamczarz, H.W. Holloway, T. Giordano, D. Chen, K. Furukawa, K. Sambamurti, A. Brossi and D.K. Lahiri, Proc. Natl. Acad. Sci. USA, 102, 17213 (2005); doi:10.1073/pnas.0508575102.

Issue

Vol. 27 No. 11 (2015): Vol 27 Issue 11

Synthesis, Crystal Structure and Cholinesterase Enzymes Inhibitory Activities of New Pyridine Alkaloid Derivative

Corresponding Author(s) : Raza Murad Ghalib

Abstract

Keywords

Full Article

Download Citation

References

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