ANTIMICROBIAL AND ANTIVIRAL ACTIVITY OF SPIROINDOLINONES BEARING BENZOTHIAZOLE MOIETY

Abstract

In this study, 5-chloro-1'-methyl-5'-nitro-3H-spiro[1,3-benzothiazole2,3'-indole]-2'(1'H)-one (3u) was synthesized by the reaction of 1-methyl5-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, H 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: [e-mail]

Keywords

• Spiroindolinones
• benzothiazole
• antimicrobial activity
• antituberculosis activity
• antiviral activity.

ANTIMICROBIAL AND ANTIVIRAL ACTIVITY OF SPIROINDOLINONES BEARING BENZOTHIAZOLE MOIETY

Abstract

Bu çalışmada 1-metil-5-nitro-1H-indol-2,3-dion (1m) ile 2-amino- 4-klorotiyofenol (2)'ün etanollü ortamdaki reaksiyonundan 5-kloro-1'- metil-5'-nitro-3H-spiro[1,3-benzotiyazol-2,3'-indol]-2'(1'H)-on (3u) bileşiği sentezlenmiştir. 3u nun yapısı spektral (IR, 1 H NMR, HSQC- 2D, LCMS-ESI) bulgular ve elemental analiz ile kanıtlanmıştır. Yeni spiroindolinon türevi 3u, daha önce rapor edilen benzotiyazol ya da 5-klorobenzotiyazol artığı taşıyan spiroindolinon türevleri 3a-t ile birlikte seçilen bakteri suşlarına karşı in vitro antibakteriyel aktivite için test edilmiştir. Test edilen bileşikler içinde 3i ve 3l Staphylococcus aureus ve Candida albicans'a karşı en yüksek etkinlik göstermiştir. Yalnız 3b Staphylococcus epidermidis' e karşı önemli derecede etkili bulunmuştur. 3a-n nin Mycobacterium tuberculosis H37Rv karşı in vitro antitüberküloz etkileri incelenmiştir; ama test edilen bileşiklerin çoğu zayıf antitüberküloz etki göstermiştir. Tüm bileşikler CRFK, HeLa ve HEL hücrelerinde DNA ve RNA virüslerine karşı ayrıca test edilmiştir. Test edilen bileşiklerin sitotoksisiteleri standartlara kıyasla genellikle çok yüksektir.

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