Discovery of Aporphine Analogues as Potential Antiplatelet and Antioxidant Agents: Design, Synthesis, Structure-Activity Relationships, Biological Evaluations, and insilico Molecular Docking Studies
- Authors
- Sharma, Vashundhra; Jaiswal, Pradeep K.; Kumar, Surendra; Mathur, Manas; Swami, Ajit K.; Yadav, Dharmendra K.; Chaudhary, Sandeep
- Issue Date
- 6-Sep-2018
- Publisher
- WILEY-V C H VERLAG GMBH
- Keywords
- alkaloids; antioxidant activity; antiplatelet activity; radicals; structure-activity relationships
- Citation
- CHEMMEDCHEM, v.13, no.17, pp.1817 - 1832
- Journal Title
- CHEMMEDCHEM
- Volume
- 13
- Number
- 17
- Start Page
- 1817
- End Page
- 1832
- URI
- https://scholarworks.bwise.kr/gachon/handle/2020.sw.gachon/3318
- DOI
- 10.1002/cmdc.201800318
- ISSN
- 1860-7179
- Abstract
- To explore the potential of aporphine alkaloids, a novel series of functionalized aporphine analogues with alkoxy (OCH3, OC2H5, OC3H7) functional groups at C1/C2 of ringA and an acyl (COCH3 and COPh) or phenylsulfonyl (SO2Ph and SO2C6H4-3-CH3) functionality at the N6 position of ringB of the aporphine scaffold were synthesized and evaluated for their arachidonic acid (AA)-induced antiplatelet aggregation inhibitory activity and 2,2-diphenyl-1-picrylhydrazyl (DPPH) free-radical-scavenging antioxidant activity, with acetylsalicylic acid and ascorbic acid as standard references, respectively. The preliminary structure-activity relationship related to AA-induced platelet aggregation inhibitory activity results showed that the aporphine analogues 1-[1,2,9,10-tetramethoxy-6a,7-dihydro-4H-dibenzo[de,g]quinolin-6(5H)-yl]ethanone and 1-[2-(benzyloxy)-1,9,10-trimethoxy-6a,7-dihydro-4H-dibenzo[de,g]quinolin-6(5H)-yl]ethanone to be the best compounds of the series. Moreover, the DPPH free-radical-scavenging antioxidant activity results demonstrated that the aporphine analogues 1,2,9,10-tetramethoxy-6-(methylsulfonyl)-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline, 2-ethoxy-1,9,10-trimethoxy-6-(methylsulfonyl)-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline, 1-ethoxy-2,9,10-trimethoxy-6-(methylsulfonyl)-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline, 2,9,10-trimethoxy-6-(methylsulfonyl)-1-propoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline, and 1-(benzyloxy)-2,9,10-trimethoxy-6-(methylsulfonyl)-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline were the best compounds of the series. Moreover, insilico molecular docking simulation studies of the active analogues were also performed.
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