Synthesis of new spiroindolinones incorporating a benzothiazole moiety as antioxidant agents
| Autor: | Süheyla Özbey, Nilgün Karalı, Aydın Salman, Özlen Güzel, Nurten Ozsoy |
|---|---|
| Rok vydání: | 2010 |
| Předmět: |
Models
Molecular Indoles Magnetic Resonance Spectroscopy Antioxidant DPPH medicine.medical_treatment Trolox equivalent antioxidant capacity Antineoplastic Agents Crystallography X-Ray Chemical synthesis Antioxidants Lipid peroxidation chemistry.chemical_compound Cell Line Tumor Drug Discovery medicine Humans Moiety Spiro Compounds Benzothiazoles Pharmacology ABTS Molecular Structure Organic Chemistry General Medicine chemistry Benzothiazole Nuclear chemistry |
| Zdroj: | European Journal of Medicinal Chemistry. 45:1068-1077 |
| ISSN: | 0223-5234 |
| DOI: | 10.1016/j.ejmech.2009.12.001 |
| Popis: | 3H-Spiro[1,3-benzothiazole-2,3'-indol]-2'(1'H)-ones 3a-c and 4a-e were synthesized from treating the 5-substituted 1H-indole-2,3-diones with 2-aminothiophenol in ethanol. The structures were confirmed by elemental analyses, spectrometry (IR, (1)H NMR, (13)C NMR, HSQC-2D and LCMS-APCI) and single crystal X-ray analysis. The new compounds were screened for their antioxidant activities such as the Fe(3+)/ascorbate system induced inhibition of lipid peroxidation (LP) in liposomes, trolox equivalent antioxidant capacity (TEAC), scavenging effect on diphenylpicryl hydrazine (DPPH*), and reducing power. These compounds showed potent scavenging activities against DPPH* and 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS*(+)) radicals, reducing powers, and strong inhibitory capacity on lipid peroxidation. Compound 4a incorporating methyl both at R(1) and R(2) was found to be the most potent antioxidant described in this study. Compounds 3b and 4b were selected as representative compounds by the National Cancer Institute for screening against anticancer activity and these compounds were found to be cytotoxic against CNS cancer cell line SNB-75 in the primary screen. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full Text from ScienceDirect