Research Article | Open Access Volume 5 | Issue 3 |Paper 02 | doi.org/10.15228/2015.v05.i03.p02 |
S.Z. Siddiqui
Department of Chemistry, Government College University, Lahore-54000, Pakistan
M.A. Abbasi
Department of Chemistry, Government College University, Lahore-54000, Pakistan
Aziz Ur Rehman
Department of Chemistry, Government College University, Lahore-54000, Pakistan
M. Irshad
Department of Chemistry, Government College University, Lahore-54000, Pakistan
M. Ashraf
Department of Biochemistry and Biotechnology; The Islamia University of Bahawalpur, Bahawalpur- 63100, Pakistan
Qurat Ul Ain
Department of Biochemistry and Biotechnology; The Islamia University of Bahawalpur, Bahawalpur- 63100, Pakistan
Bushra Mirza
Department of Biochemistry, Quaid-i-Azam University, Islamabad, 45320, Pakistan
H. Ismail
Department of Biochemistry, Quaid-i-Azam University, Islamabad, 45320, Pakistan
| Received 27 Jan, 2015 | Accepted 10 Feb, 2015 | Published 10 Sep, 2015 |
ABSTRACT:
1, 3, 4-Oxadiazoles are known to possess diverse biological activities and proposed synthetic methodology was aimed to synthesize biologically active 1, 3, 4-oxadiazole-2-thiols derivatives. It was instigated by converting 2-phenylacetic acid (1) to ethyl-2-phenylacetate (2) by Fischer esterification method. The ester underwent hydrazinolysis to afford 2-phenylacetohydrazide (3) which was transformed via ring closure with carbon disulfide in alcoholic base to achieve 5-benzyl-1,3,4-oxadiazole-2-thiol (4). Finally, the parent oxadiazole 4 was reacted with a variety of aralkylated/arylated/arenylated halides (5a-i) in polar aprotic solvent; N,Nˈ-dimethylformamide (DMF) and lithium hydride (LiH) which acted as base under to afford 2- (aralkylated/arylated/arenylatedthio) 5-benzyl-1,3,4-oxadiazoles (6a-i). The synthesized derivatives were screened against acetyl/butyrylcholinesterases for enzyme inhibitory potential. The incorporation of 3-nitro/4-nitrophenyl moieties on S-position of parent oxadiaozle demonstrated decent inhibitory potential against cholinesterases while rest displayed weak inhibition relative to reference standard Eserine. The LD50 data revealed that most of the derivatives were found to be less cytotoxic relative to standard doxorubicin
How to Cite this paper?
APA-7 Style
Siddiqui, S.Z., Abbasi, M.A., Rehman, A.U., Irshad, M., Ashraf, M., Ain, .U., Mirza, B., Ismail, H. (2015). 2-(Aralkylated/Arylated/Arenylatedthio) 5-Benzyl-1, 3, 4-Oxadiazoles: As Less Cytotoxic And Moderate Inhibitors Of Cholinesterases. Pakistan Journal of Chemistry, 5(3), 104-110. https://doi.org/10.15228/2015.v05.i03.p02
ACS Style
Siddiqui, S.Z.; Abbasi, M.A.; Rehman, A.U.; Irshad, M.; Ashraf, M.; Ain, .U.; Mirza, B.; Ismail, H. 2-(Aralkylated/Arylated/Arenylatedthio) 5-Benzyl-1, 3, 4-Oxadiazoles: As Less Cytotoxic And Moderate Inhibitors Of Cholinesterases. Pak. J. Chem. 2015, 5, 104-110. https://doi.org/10.15228/2015.v05.i03.p02
AMA Style
Siddiqui SZ, Abbasi MA, Rehman AU, Irshad M, Ashraf M, Ain U, Mirza B, Ismail H. 2-(Aralkylated/Arylated/Arenylatedthio) 5-Benzyl-1, 3, 4-Oxadiazoles: As Less Cytotoxic And Moderate Inhibitors Of Cholinesterases. Pakistan Journal of Chemistry. 2015; 5(3): 104-110. https://doi.org/10.15228/2015.v05.i03.p02
Chicago/Turabian Style
Siddiqui, S., Z., M. A. Abbasi, Aziz Ur Rehman, M. Irshad, M. Ashraf, Qurat Ul Ain, Bushra Mirza, and H. Ismail. 2015. “2-(Aralkylated/Arylated/Arenylatedthio) 5-Benzyl-1, 3, 4-Oxadiazoles: As Less Cytotoxic And Moderate Inhibitors Of Cholinesterases” Pakistan Journal of Chemistry 5, no. 3: 104-110. https://doi.org/10.15228/2015.v05.i03.p02
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