ANTIMICROBIAL AND ANTIVIRAL ACTIVITY OF SPIROINDOLINONES BEARING BENZOTHIAZOLE MOIETY

Ö. GÜZEL AKDEMİR, N. KARALI G. ERMUT
458 95

Öz


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:

ÖZET
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, 1H 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.
Key words: Spiroindolinones, benzothiazole, antimicrobial activity,
antituberculosis activity, antiviral activity.


Anahtar kelimeler


Spiroindolinones, benzothiazole, antimicrobial activity, antituberculosis activity, antiviral activity.

Tam metin:

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Referanslar


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