ANTIMICROBIAL AND ANTIVIRAL ACTIVITY OF SPIROINDOLINONES BEARING BENZOTHIAZOLE MOIETY

SUMMARY In this study, 5-chloro-1'-methyl-5'-nitro-3H-spiro[1,3-benzothiazole- 2,3'-indole]-2'(1'H)-one (3u) was synthesized by the reaction of 1-methyl- 5-nitro-1H-indole-2,3-dione (1m) with 2-amino-4-chlorothiophenol (2) in ethanol. The structure of 3u was confirmed by the spectral (IR, 1H NMR, HSQC-2D, LCMS-ESI) data and elemental analysis. The new spiroindolinone derivative 3u, along with previously reported spiroindolinone derivatives 3a-t bearing benzothiazole or 5-chlorobenzothiazole moiety were tested for in vitro antimicrobial activity against selected strains. Among the tested compounds, 3i and 3l displayed the highest efficacy against Staphylococcus aureus and Candida albicans. Only 3b was found to be significantly active against Staphylococcus epidermidis. 3a-n were evaluated for in vitro antituberculosis activity against Mycobacterium tuberculosis H37Rv, but most of the tested compounds showed weakly antitubercular activity. All compounds were also evaluated against some DNA and RNA viruses in CRFK, HeLa and HEL cells. Cytotoxicities of the tested compounds were generally very high compared to standards. *Correspondence: OZET Bu calismada 1-metil-5-nitro-1H-indol-2,3-dion (1m) ile 2-amino- 4-klorotiyofenol (2)'un etanollu ortamdaki reaksiyonundan 5-kloro-1'- metil-5'-nitro-3H-spiro[1,3-benzotiyazol-2,3'-indol]-2'(1'H)-on (3u) bilesigi sentezlenmistir. 3u nun yapisi spektral (IR, 1H NMR, HSQC- 2D, LCMS-ESI) bulgular ve elemental analiz ile kanitlanmistir. Yeni spiroindolinon turevi 3u, daha once rapor edilen benzotiyazol ya da 5-klorobenzotiyazol artigi tasiyan spiroindolinon turevleri 3a-t ile birlikte secilen bakteri suslarina karsi in vitro antibakteriyel aktivite icin test edilmistir. Test edilen bilesikler icinde 3i ve 3l Staphylococcus aureus ve Candida albicans'a karsi en yuksek etkinlik gostermistir. Yalniz 3b Staphylococcus epidermidis' e karsi onemli derecede etkili bulunmustur. 3a-n nin Mycobacterium tuberculosis H37Rv karsi in vitro antituberkuloz etkileri incelenmistir; ama test edilen bilesiklerin cogu zayif antituberkuloz etki gostermistir. Tum bilesikler CRFK, HeLa ve HEL hucrelerinde DNA ve RNA viruslerine karsi ayrica test edilmistir. Test edilen bilesiklerin sitotoksisiteleri standartlara kiyasla genellikle cok yuksektir. Key words: Spiroindolinones, benzothiazole, antimicrobial activity, antituberculosis activity, antiviral activity.