Sains Malaysiana 41(8)(2012): 977–982

Diorganotin(IV) Alkylcyclohexyldithiocarbamate Compounds: Synthesis,

Characterization and Biological Activities

(Sebatian Diorganostanum(IV) Alkilsikloheksilditiokarbamat: Sintesis,

Pencirian dan Aktiviti Biologi)

Normah Awang*

Environmental Health Programme, Faculty of Health Sciences

Universiti Kebangsaan Malaysia, Jalan Raja Muda Abdul Aziz

50300 Kuala Lumpur, Malaysia

Ibrahim Baba

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

Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia

Received: 14 April 2010 / Accepted: 21 February 2012

ABSTRACT

Three new compounds of dibutyltin(IV) with N-alkylcyclohexyldithiocarbamate were successfully synthesized using in situ methods. Elemental analysis data of these complexes were in agreement with the general formula of (C4H9)2Sn[S2CNR(C6H11)]2 (R = CH3, C2H5, i-C3H7). Infrared spectra showed that the thioureide bands, ν(C=N) appeared in the region of 1475 - 1479 cm-1, ν(C=S) bands in the region of 978 - 998 cm-1 and ν(Sn-S) bands in the region of 375 – 389 cm-1. Crystal structure of dibutyltin(IV) ethylcyclohexyldithiocarbamate showed a triclinic system and space group P-1. The crystal structure of the dithiocarbamate ligands were bidentically chelated to the tin atom with Sn-S unsymmetrical: Sn(1)-S(1) = 2.9255(11) and Sn(1)-S(2) = 2.5419(10); Sn(1)-S(3) = 2.8922(9) and Sn(1)-S(4) = 2.5293(10)Å. These compounds were screened for antibacterial activity against four bacteria species using the disc diffusion method. The results showed that (C4H9)2Sn[S2CN(i-C3H7)(C6H11)]2 was mildly active against those three bacteria. Whereas all of these compounds exhibited in vitro cytotoxicity activity toward human leukemic promyelocites HL-60 cell line with CD50 values lower than 1.00 μg/mL.

Keywords: Biological activities; dibutyltin(IV); dithiocarbamate

ABSTRAK

Tiga sebatian baru dibutilstanum(IV) dengan ligan N-alkilsikloheksilditiokarbamat telah berjaya disintesis menggunakan kaedah in situ. Data analisis unsur sebatian ini bersetuju dengan formula umum (C4H9)2Sn[S2CNR(C6H11)]2 (R = CH3, C2H5, i-C3H7). Spektrum inframerah menunjukkan jalur tioureida, ν(C=N) berada pada julat 1475 - 1479 cm-1, ν(C=S) berada dalam julat 978 - 998 cm-1 dan ν(Sn-S) berada pada julat 375 – 389 cm-1. Struktur hablur sebatian dibutilstanum(IV) etilsikloheksilditiokarbamat adalah bersistem triklinik dengan kumpulan ruang P-1. Ligan ditiokarbamat mengkelat kepada logam stanum secara bidentat dengan ikatan Sn-S yang tidak simetri: Sn(1)-S(1) = 2.9255(11) dan Sn(1)-S(2) = 2.5419(10); Sn(1)-S(3) = 2.8922(9) dan Sn(1)-S(4) = 2.5293(10) Å. Sebatian ini telah diuji ke atas empat spesies bakteria dan didapati (C4H9)2Sn[S2CN(i-C3H7)(C6H11)]2 mempunyai aktiviti yang sederhana terhadap tiga bakteria. Ketiga-tiga sebatian ini menunjukkan aktiviti sitotoksik secara in vitro terhadap titisan sel leukemia promielosit manusia, HL-60 dengan nilai CD₅₀ kurang daripada 1.0 μg/mL.

Kata kunci: Aktiviti biologi; dibutilstanum(IV); ditiokarbamat

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*Corresponding author; email: norm@ukm.my