An eco-friendly catalytic system for multicomponent, one-pot synthesis of novel spiro-chromeno indoline-triones and their anti-prostate cancer potentials evaluated via alkaline phosphatase inhibition mechanism
| Autor: | A. Sivakumar, V. Violet Dhayabaran, M. Rajesh Kumar, A. Manikandan |
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| Rok vydání: | 2018 |
| Předmět: |
Male
Reaction mechanism Indoles One-pot synthesis Antineoplastic Agents 01 natural sciences Biochemistry Catalysis Structure-Activity Relationship 03 medical and health sciences chemistry.chemical_compound 0302 clinical medicine Drug Discovery Humans Spiro Compounds Enzyme Inhibitors Molecular Biology Dose-Response Relationship Drug Molecular Structure 010405 organic chemistry Isatin Organic Chemistry Prostatic Neoplasms Regioselectivity Alkaline Phosphatase Combinatorial chemistry 0104 chemical sciences Molecular Docking Simulation chemistry 030220 oncology & carcinogenesis Yield (chemistry) Indoline Alkaline phosphatase |
| Zdroj: | Bioorganic Chemistry. 81:44-54 |
| ISSN: | 0045-2068 |
| Popis: | A green and efficient straightforward tactic for the one-pot regioselective synthesis of novel 10,10-dimethyl-9,10,11,11a-tetrahydro-6H-spiro[chromeno[4,3–b]chromene-7,3′-indoline]-2′,6,8 (7aH) -triones (4a-n) in one-pot modus has been established using eco-friendly p-toluenesulphonic acid as catalyst. Among the solvents that were used for synthesis, 4a-n were suitably synthesized with maximum yield (90–98%) in water. We avoided column purification and the formed by-product in the process is environmental-friendly. Hence, this reaction may consider as an astonishing piece work in this study, why because, the reaction mechanism that depends on the nature of the group attached to the isatin ring nitrogen atom. The main advantage of this protocol includes short reaction time, good yield, easy to work-up, practical simplicity, high regioselectivity and reduced pollutant, cost and avoids tedious purification. These pharmaceutically important compounds (4a-n) were recognized for their alkaline phosphatase inhibition and prostate cancer medication capabilities. The selective activity relation between alkaline phosphatase and prostate cancer was unveiled through the interaction of 4a-n to Human alkaline phosphatase (PDB ID: 1EW2 ). |
| Databáze: | OpenAIRE |
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