Design, synthesis and biological evaluation of furan based α-aminophosphonate derivatives as anti-Alzheimer agent
A series of novel α -aminophosphonates bearing furan motif were designed and were synthesized under solvent-free condition and further evaluated for inhibition activity of acetylcholinesterase (AChE), butyrylcholinesterase (BuChE), and antioxidant property. All the synthesized compounds 4(a-h) showe...
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Veröffentlicht in: | Journal of the Iranian Chemical Society 2022, Vol.19 (7), p.3103-3116 |
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creator | Uparkar, Jasmin J. Dhavan, Pratik P. Jadhav, Bhaskar L. Pawar, Suresh D. |
description | A series of novel
α
-aminophosphonates bearing furan motif were designed and were synthesized under solvent-free condition and further evaluated for inhibition activity of acetylcholinesterase (AChE), butyrylcholinesterase (BuChE), and antioxidant property. All the synthesized compounds 4(a-h) showed good inhibition against AChE (IC
50
= 0.88–4.46 µM) and BuChE (IC
50
= 2.30–18.59 µM). Compound 4c was found to have maximum inhibitory potential against AChE with IC
50
= 0.884 ± 0.002 µM while IC
50
= 2.297 ± 0.091µM BuChE, suggesting that the synthesized compound are dual-inhibitors. Molecular docking studies suggested that the compound binds to both peripheral anionic site and catalytic anionic site which corroborate with the results obtained in kinetic inhibition suggesting a mixed-type inhibition. Predicted ADME showed good drug-likeness properties. Further, antioxidant activity using DPPH radical was performed; it was observed that all the compounds showed promising antioxidant activity. The highest antioxidant property was exhibited by compound 4c with IC
50
value 30.04 when compared to ascorbic acid.
Graphical abstract |
doi_str_mv | 10.1007/s13738-022-02515-w |
format | Article |
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α
-aminophosphonates bearing furan motif were designed and were synthesized under solvent-free condition and further evaluated for inhibition activity of acetylcholinesterase (AChE), butyrylcholinesterase (BuChE), and antioxidant property. All the synthesized compounds 4(a-h) showed good inhibition against AChE (IC
50
= 0.88–4.46 µM) and BuChE (IC
50
= 2.30–18.59 µM). Compound 4c was found to have maximum inhibitory potential against AChE with IC
50
= 0.884 ± 0.002 µM while IC
50
= 2.297 ± 0.091µM BuChE, suggesting that the synthesized compound are dual-inhibitors. Molecular docking studies suggested that the compound binds to both peripheral anionic site and catalytic anionic site which corroborate with the results obtained in kinetic inhibition suggesting a mixed-type inhibition. Predicted ADME showed good drug-likeness properties. Further, antioxidant activity using DPPH radical was performed; it was observed that all the compounds showed promising antioxidant activity. The highest antioxidant property was exhibited by compound 4c with IC
50
value 30.04 when compared to ascorbic acid.
Graphical abstract</description><identifier>ISSN: 1735-207X</identifier><identifier>EISSN: 1735-2428</identifier><identifier>DOI: 10.1007/s13738-022-02515-w</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer Berlin Heidelberg</publisher><subject>Analytical Chemistry ; Antioxidants ; Ascorbic acid ; Biochemistry ; Chemical synthesis ; Chemistry ; Chemistry and Materials Science ; Inorganic Chemistry ; Molecular docking ; Organic Chemistry ; Original Paper ; Physical Chemistry</subject><ispartof>Journal of the Iranian Chemical Society, 2022, Vol.19 (7), p.3103-3116</ispartof><rights>Iranian Chemical Society 2022</rights><rights>Iranian Chemical Society 2022.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c319t-5ba5f9a8d8ea5095df1bf3abfad426fd020cdcf1e4835e4bbc568e7f8d74d7183</citedby><cites>FETCH-LOGICAL-c319t-5ba5f9a8d8ea5095df1bf3abfad426fd020cdcf1e4835e4bbc568e7f8d74d7183</cites><orcidid>0000-0002-9642-2368</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s13738-022-02515-w$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s13738-022-02515-w$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>315,781,785,27926,27927,41490,42559,51321</link.rule.ids></links><search><creatorcontrib>Uparkar, Jasmin J.</creatorcontrib><creatorcontrib>Dhavan, Pratik P.</creatorcontrib><creatorcontrib>Jadhav, Bhaskar L.</creatorcontrib><creatorcontrib>Pawar, Suresh D.</creatorcontrib><title>Design, synthesis and biological evaluation of furan based α-aminophosphonate derivatives as anti-Alzheimer agent</title><title>Journal of the Iranian Chemical Society</title><addtitle>J IRAN CHEM SOC</addtitle><description>A series of novel
α
-aminophosphonates bearing furan motif were designed and were synthesized under solvent-free condition and further evaluated for inhibition activity of acetylcholinesterase (AChE), butyrylcholinesterase (BuChE), and antioxidant property. All the synthesized compounds 4(a-h) showed good inhibition against AChE (IC
50
= 0.88–4.46 µM) and BuChE (IC
50
= 2.30–18.59 µM). Compound 4c was found to have maximum inhibitory potential against AChE with IC
50
= 0.884 ± 0.002 µM while IC
50
= 2.297 ± 0.091µM BuChE, suggesting that the synthesized compound are dual-inhibitors. Molecular docking studies suggested that the compound binds to both peripheral anionic site and catalytic anionic site which corroborate with the results obtained in kinetic inhibition suggesting a mixed-type inhibition. Predicted ADME showed good drug-likeness properties. Further, antioxidant activity using DPPH radical was performed; it was observed that all the compounds showed promising antioxidant activity. The highest antioxidant property was exhibited by compound 4c with IC
50
value 30.04 when compared to ascorbic acid.
Graphical abstract</description><subject>Analytical Chemistry</subject><subject>Antioxidants</subject><subject>Ascorbic acid</subject><subject>Biochemistry</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Inorganic Chemistry</subject><subject>Molecular docking</subject><subject>Organic Chemistry</subject><subject>Original Paper</subject><subject>Physical Chemistry</subject><issn>1735-207X</issn><issn>1735-2428</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNp9kE1OwzAUhCMEEqVwAVaW2BKwkzh2l1X5lSqxAYmd5cTPqavULnbSqtyKi3AmXAJix2L0ZvHNPGmS5JzgK4Ixuw4kZzlPcZZFUULT7UEyIiynaVZk_PDXY_Z6nJyEsMSYMkyLUeJvIJjGXqKws90i-oCkVagyrnWNqWWLYCPbXnbGWeQ00r2XFlUygEKfH6lcGevWCxeirOwAKfBmE-kNxKJ9V2fSafu-ALMCj2QDtjtNjrRsA5z93HHycnf7PHtI50_3j7PpPK1zMulSWkmqJ5IrDpLiCVWaVDqXlZaqyEqtcIZrVWsCBc8pFFVV05ID01yxQjHC83FyMfSuvXvrIXRi6Xpv40uRlayknJR8T2UDVXsXggct1t6spN8JgsV-WzFsK-K24ntbsY2hfAiFCNsG_F_1P6kvDCSBLg</recordid><startdate>2022</startdate><enddate>2022</enddate><creator>Uparkar, Jasmin J.</creator><creator>Dhavan, Pratik P.</creator><creator>Jadhav, Bhaskar L.</creator><creator>Pawar, Suresh D.</creator><general>Springer Berlin Heidelberg</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-9642-2368</orcidid></search><sort><creationdate>2022</creationdate><title>Design, synthesis and biological evaluation of furan based α-aminophosphonate derivatives as anti-Alzheimer agent</title><author>Uparkar, Jasmin J. ; Dhavan, Pratik P. ; Jadhav, Bhaskar L. ; Pawar, Suresh D.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c319t-5ba5f9a8d8ea5095df1bf3abfad426fd020cdcf1e4835e4bbc568e7f8d74d7183</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Analytical Chemistry</topic><topic>Antioxidants</topic><topic>Ascorbic acid</topic><topic>Biochemistry</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Inorganic Chemistry</topic><topic>Molecular docking</topic><topic>Organic Chemistry</topic><topic>Original Paper</topic><topic>Physical Chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Uparkar, Jasmin J.</creatorcontrib><creatorcontrib>Dhavan, Pratik P.</creatorcontrib><creatorcontrib>Jadhav, Bhaskar L.</creatorcontrib><creatorcontrib>Pawar, Suresh D.</creatorcontrib><collection>CrossRef</collection><jtitle>Journal of the Iranian Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Uparkar, Jasmin J.</au><au>Dhavan, Pratik P.</au><au>Jadhav, Bhaskar L.</au><au>Pawar, Suresh D.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design, synthesis and biological evaluation of furan based α-aminophosphonate derivatives as anti-Alzheimer agent</atitle><jtitle>Journal of the Iranian Chemical Society</jtitle><stitle>J IRAN CHEM SOC</stitle><date>2022</date><risdate>2022</risdate><volume>19</volume><issue>7</issue><spage>3103</spage><epage>3116</epage><pages>3103-3116</pages><issn>1735-207X</issn><eissn>1735-2428</eissn><abstract>A series of novel
α
-aminophosphonates bearing furan motif were designed and were synthesized under solvent-free condition and further evaluated for inhibition activity of acetylcholinesterase (AChE), butyrylcholinesterase (BuChE), and antioxidant property. All the synthesized compounds 4(a-h) showed good inhibition against AChE (IC
50
= 0.88–4.46 µM) and BuChE (IC
50
= 2.30–18.59 µM). Compound 4c was found to have maximum inhibitory potential against AChE with IC
50
= 0.884 ± 0.002 µM while IC
50
= 2.297 ± 0.091µM BuChE, suggesting that the synthesized compound are dual-inhibitors. Molecular docking studies suggested that the compound binds to both peripheral anionic site and catalytic anionic site which corroborate with the results obtained in kinetic inhibition suggesting a mixed-type inhibition. Predicted ADME showed good drug-likeness properties. Further, antioxidant activity using DPPH radical was performed; it was observed that all the compounds showed promising antioxidant activity. The highest antioxidant property was exhibited by compound 4c with IC
50
value 30.04 when compared to ascorbic acid.
Graphical abstract</abstract><cop>Berlin/Heidelberg</cop><pub>Springer Berlin Heidelberg</pub><doi>10.1007/s13738-022-02515-w</doi><tpages>14</tpages><orcidid>https://orcid.org/0000-0002-9642-2368</orcidid></addata></record> |
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subjects | Analytical Chemistry Antioxidants Ascorbic acid Biochemistry Chemical synthesis Chemistry Chemistry and Materials Science Inorganic Chemistry Molecular docking Organic Chemistry Original Paper Physical Chemistry |
title | Design, synthesis and biological evaluation of furan based α-aminophosphonate derivatives as anti-Alzheimer agent |
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