ACETYLCHOLINESTERASE INHIBITION ACTIVITY OF SOME QUINOLINYL SUBSTITUTED TRIAZOLOTHIADIAZOLE DERIVATIVES

© 2015 Muhammad Rafiq^a, Qamar Abbas^a, Muhammad Saleem^b, Muhammad Hanif^c, Ki Hwan Lee^b, and Sung-Yum Seo^{a, #}

^#E-mail: dnalove@kongju.ac.kr

^aDepartment of Biology, Kongju National University, Kongju, 3147701 Korea;
^bDepartment of Chemistry, Kongju National University, Kongju, 3147701 Korea;
^cDepartment of Chemistry, Quaid7i7Azam University, Islamabad, 45320 Pakistan

Received May 12, 2014; in final form 28.08.2014

A series of aralkanoic acids was converted into aralkanoic acid hydrazides through their esters formation. The aralkanoic acid hydrazides upon treatment with carbon disulfide and methanolic potassium hydroxide yielded potassium dithiocarbazinate salts, which on refluxing with aqueous hydrazine hydrate yielded 5-aralkyl-4-amino-3-mercapto-1,2,4-triazoles. The target compounds, 3-aralkyl-6-(substitutedquinolinyl)[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles, were synthesized by condensing various quinolinyl substituted carboxylic acids with 5-aralkyl-4-amino-3-mercapto-1,2,4-triazoles in phosphorus oxychloride. The structures of the newly synthesized triazolothiadiazoles were characterized by IR, ¹H NMR, ¹³C NMR, and elemental analysis studies. The structure of one of the 5-aralkyl-4-amino-3-mercapto-1,2,4-triazoles was unambiguously deduced by single crystal X-ray diffraction analysis. All the synthesized compounds were screened for their acetylcholinesterase inhibition activities. Four of the triazolothiadiazoles exhibited excellent acetylcholinesterase inhibition activities as compared to the reference inhibitor.

Keywords: quinolinyl substituted triazolothiadiazole, X-ray diffraction analysis, acetylcholinesterase inhibition assay.

Биоорг. химия 2015, 41(2): 195–202