2-(Aralkylated/Arylated/Arenylatedthio) 5-Benzyl-1, 3, 4-oxadiazoles: as less cytotoxic and moderate inhibitors of Cholinesterases. | [Pakistan Journal of Chemistry • 2015]

Author(s):

1. S. Z. Siddiqui: Department of Chemistry, Government College University, Lahore-54000, Pakistan

2. M. A. Abbasi: Department of Chemistry, Government College University, Lahore-54000, Pakistan

3. Aziz-ur-Rehman: Department of Chemistry, Government College University, Lahore-54000, Pakistan

4. M. Irshad: Department of Chemistry, Government College University, Lahore-54000, Pakistan

5. M. Ashraf: Department of Biochemistry and Biotechnology, The Islamia University of Bahawalpur, Bahawalpur- 63100, Pakistan

6. Qurat-ul-Ain: Department of Biochemistry and Biotechnology, The Islamia University of Bahawalpur, Bahawalpur- 63100, Pakistan

7. Bushra Mirza: Department of Biochemistry, Quaid-i-Azam University, Islamabad, 45320, Pakistan

8. H. Ismail: Department of Biochemistry, Quaid-i-Azam University, Islamabad, 45320, Pakistan

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,N'-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.

Page(s): 101-107

DOI: DOI not available

Published: Journal: Pakistan Journal of Chemistry, Volume: 5, Issue: 3, Year: 2015

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