Sains Malaysiana 40(5)(2011): 445–450

Synthesis and Antimicrobial Activity of 1-(5-Mercapto-1,3,4-Oxadiazol-2-yl)-2-(Pyridine-2-ylamino)ethanone

(Sintesis dan Aktiviti Antimikrob Sebatian 1-(5-Merkapto-1,3,4-Oksadiazol-2-yl)-2-(Piridine-2-ylamino)etanon

Jumat Salimon^1, *, NadiaSalih¹ & Hasan Hussien^1,2

¹School of Chemical Sciences and Food Technology, Faculty of Science and Technology

Universiti Kebangsaan Malaysia, 43600 Bangi Selangor D.E., Malaysia

²Department of Chemistry, College of Science, Al-Nahrain University, Baghdad, Iraq

Diserahkan: 16 September 2009 / Diterima: 21 June 2010

ABSTRACT

1-(5-Mercapto-1,3,4-oxadiazol-2-yl)-2-(pyridine-2-ylamino)ethanone (3), has been synthesized from 2-(pyridine-2-ylamino)acetohydrazide (2). A yellow colored compound (2) was reacted with carbon disulfide and potassium hydroxide in absolute ethanol to obtain the 1-(5-mercapto-1,3,4-oxadiazol-2-yl)-2-(pyridine-2-ylamino)ethanone. Structures of the synthesized compounds were supported by means of IR, NMR, MS spectroscopic and elemental analysis. The synthesized compounds were evaluated for their antimicrobial activity and were expressed as the corresponding minimum inhibitory concentration (MIC). A brown colored compound (3) with 90% yield has been successfully synthesized. This compound was found to have significant antimicrobial activity with MIC value ranging from 30.2 - 43.2 μg cm-3. The findings of the present study indicate that cyclization of hydrazide acid group of 2-(pyridine-2-ylamino)acetohydrazide (2) into 1,3,4-oxadiazole nucleus resulted in increased antimicrobial activity.

Keywords: 1,3,4-oxadiazoles compound; antimicrobial activity; hydrazide acid

ABSTRAK

Sebatian (3), 1-(5-merkapto-1,3,4-oksadiazol-2-yl)-2-(piridine-2-ylamino)etanon telah disintesis daripada sebatian (2), 2-(pridin-2-ilamino)asetohidrazida. Sebatian (2) yang berwarna kuning telah ditindakbalaskan dengan karbon disulfida dan kalium hidroksida dalam etanol kontang untuk menghasilkan sebatian 1-(5-merkapto-1,3,4-oksadiazol-2-yl)-2-(piridine-2-ylamino)etanon. Struktur sebatian yang disintesis disokong oleh cerapan daripada instrumen IR, NMR, spektroskopi jisim dan analisis unsur. Sebatian yang disintesis telah dinilai untuk aktiviti antimikrob dan dinyatakan sebagai nilai penghantaran kepekatan penghalangan minima (MIC). Sebatian (3) yang berwarna perang dengan peratusan hasil 90% telah berjaya disintesis. Sebatian ini didapati menunjukkan aktiviti antimikrob yang signifikan dengan nilai MIC dalam julat 30.2 - 43.2 μg cm-3. Kajian ini menunjukkan bahawa proses pengsiklikan kumpulan asid hidrazida dalam sebatian 2-(piridin-2-ylamino)asetohidrazida (2) kepada nukleus sebatain 1,3,4-oksadiazol menyebabkan peningkatan dalam aktiviti antimikrobial.

Kata kunci:; aktiviti antimikrob; asid hidrazida; sebatian 1,3,4-oksadiazol

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*Pengarang untuk surat-menyurat; email: jumat@ukm.my