PEG-400 Mediated an Efficient Green Synthesis of Isoxazolyl Indole-3-Carboxylic Acid Esters via Nentizescu Condensation Reaction and Their Anti-Inflammatory and Analgesic Activity
| Autor: | Praveen Kumar Pittala, Rajanarendar Eligeti, Y N Reddy, Nagi Reddy Modugu, Nagaraju Dharavath |
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| Rok vydání: | 2017 |
| Předmět: |
Indole test
PEG 400 chemistry.chemical_classification 010405 organic chemistry medicine.drug_class Carboxylic acid Analgesic Substrate (chemistry) General Chemistry 010402 general chemistry Condensation reaction 01 natural sciences Anti-inflammatory 0104 chemical sciences chemistry.chemical_compound chemistry Functional group medicine Organic chemistry |
| Zdroj: | ChemistrySelect. 2:5110-5114 |
| ISSN: | 2365-6549 |
| Popis: | Polyethylene glycol-400 (PEG-400) has been discovered as an efficient and eco-friendly reaction medium for the synthesis of new isoxazolyl indole-3-carboxylic acid esters 11 from 4-amino-3-methyl-5-styrylisoxazoles 7. Compounds 7 on treatment with β-keto ester 8 afforded the corresponding isoxazolylamino-2-butenoates 9 at ambient temperature in PEG-400. The Nentizescu condensation of compounds 9 with 1,4-benzoquinone 10 to give the title compounds isoxazolyl indole-3-craboxylic acid esters 11 under PEG-400. Structures of compounds 9 and 11 were established on the basis of IR, 1H NMR, 13C NMR and HRMS analysis. All the final compounds 11 a–s were evaluated for their anti-inflammatory and analgesic activities. Among the compounds tested, the compounds 11 b, 11 g, 11 n, 11 o, 11 p and 11 s exhibited significant anti-inflammatory and potent analgesic activities as that of standard drugs. The advantages of this protocol are: operational simplicity, environmental safety, broad substrate scope, excellent functional group tolerance, and good yields. The PEG-400 can be recovered and reused. |
| Databáze: | OpenAIRE |
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