Microwave-assisted synthesis of novel 5-substituted benzylidene amino-2-butyl benzofuran-3-yl-4-methoxyphenyl methanones as antileishmanial and antioxidant agents
[Display omitted] A series of 5-substitutedbenzylideneamino-2-butylbenzofuran-3-yl-4-methoxyphenyl methanones is synthesized and evaluated for antileishmanial and antioxidant activities. Compounds 4f (IC50 = 52.0 ± 0.09 µg/ml), 4h (IC50 = 56.0 ± 0.71 µg/ml) and 4l (IC50 = 59.3 ± 0.55 µg/ml) were sho...
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Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2018-02, Vol.28 (3), p.482-487 |
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creator | Patil, Sanjeev R. Bollikonda, Satyanarayana Patil, Rajendra H. Sangshetti, Jaiprakash N. Bobade, Anil S. Asrondkar, Ashish Reddy, Padi Pratap Shinde, Devanand B. |
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A series of 5-substitutedbenzylideneamino-2-butylbenzofuran-3-yl-4-methoxyphenyl methanones is synthesized and evaluated for antileishmanial and antioxidant activities. Compounds 4f (IC50 = 52.0 ± 0.09 µg/ml), 4h (IC50 = 56.0 ± 0.71 µg/ml) and 4l (IC50 = 59.3 ± 0.55 µg/ml) were shown significant antileishmanial when compared with standard sodium stibogluconate (IC50 = 490.0 ± 1.5 µg/ml). Antioxidant study revealed that compounds 4i (IC50 = 2.44 ± 0.47 µg/ml) and 4l (IC50 = 3.69 ± 0.44 µg/ml) have shown potent comparable activity when compared with standard ascorbic acid (IC50 = 3.31 ± 0.34 µg/ml). Molecular docking study was carried out which replicating results of biological activity in case of initial hits 4f and 4h suggesting that these compounds have a potential to become lead molecules in drug discovery process. In silico ADME study was performed for predicting pharmacokinetic profile of the synthesised antileishmanial agents and expressed good oral drug like behaviour. |
doi_str_mv | 10.1016/j.bmcl.2017.12.013 |
format | Article |
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A series of 5-substitutedbenzylideneamino-2-butylbenzofuran-3-yl-4-methoxyphenyl methanones is synthesized and evaluated for antileishmanial and antioxidant activities. Compounds 4f (IC50 = 52.0 ± 0.09 µg/ml), 4h (IC50 = 56.0 ± 0.71 µg/ml) and 4l (IC50 = 59.3 ± 0.55 µg/ml) were shown significant antileishmanial when compared with standard sodium stibogluconate (IC50 = 490.0 ± 1.5 µg/ml). Antioxidant study revealed that compounds 4i (IC50 = 2.44 ± 0.47 µg/ml) and 4l (IC50 = 3.69 ± 0.44 µg/ml) have shown potent comparable activity when compared with standard ascorbic acid (IC50 = 3.31 ± 0.34 µg/ml). Molecular docking study was carried out which replicating results of biological activity in case of initial hits 4f and 4h suggesting that these compounds have a potential to become lead molecules in drug discovery process. In silico ADME study was performed for predicting pharmacokinetic profile of the synthesised antileishmanial agents and expressed good oral drug like behaviour.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2017.12.013</identifier><identifier>PMID: 29258770</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>ADME properties ; Antileishmanial activity ; Antioxidant activity ; Benzofuran derivatives ; Docking study</subject><ispartof>Bioorganic & medicinal chemistry letters, 2018-02, Vol.28 (3), p.482-487</ispartof><rights>2017 Elsevier Ltd</rights><rights>Copyright © 2017 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c356t-573d0c22eb7b46a50007ee287328b28b77dc5b4cf696ed341be32df7eb86ecee3</citedby><cites>FETCH-LOGICAL-c356t-573d0c22eb7b46a50007ee287328b28b77dc5b4cf696ed341be32df7eb86ecee3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X17311733$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29258770$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Patil, Sanjeev R.</creatorcontrib><creatorcontrib>Bollikonda, Satyanarayana</creatorcontrib><creatorcontrib>Patil, Rajendra H.</creatorcontrib><creatorcontrib>Sangshetti, Jaiprakash N.</creatorcontrib><creatorcontrib>Bobade, Anil S.</creatorcontrib><creatorcontrib>Asrondkar, Ashish</creatorcontrib><creatorcontrib>Reddy, Padi Pratap</creatorcontrib><creatorcontrib>Shinde, Devanand B.</creatorcontrib><title>Microwave-assisted synthesis of novel 5-substituted benzylidene amino-2-butyl benzofuran-3-yl-4-methoxyphenyl methanones as antileishmanial and antioxidant agents</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>[Display omitted]
A series of 5-substitutedbenzylideneamino-2-butylbenzofuran-3-yl-4-methoxyphenyl methanones is synthesized and evaluated for antileishmanial and antioxidant activities. Compounds 4f (IC50 = 52.0 ± 0.09 µg/ml), 4h (IC50 = 56.0 ± 0.71 µg/ml) and 4l (IC50 = 59.3 ± 0.55 µg/ml) were shown significant antileishmanial when compared with standard sodium stibogluconate (IC50 = 490.0 ± 1.5 µg/ml). Antioxidant study revealed that compounds 4i (IC50 = 2.44 ± 0.47 µg/ml) and 4l (IC50 = 3.69 ± 0.44 µg/ml) have shown potent comparable activity when compared with standard ascorbic acid (IC50 = 3.31 ± 0.34 µg/ml). Molecular docking study was carried out which replicating results of biological activity in case of initial hits 4f and 4h suggesting that these compounds have a potential to become lead molecules in drug discovery process. In silico ADME study was performed for predicting pharmacokinetic profile of the synthesised antileishmanial agents and expressed good oral drug like behaviour.</description><subject>ADME properties</subject><subject>Antileishmanial activity</subject><subject>Antioxidant activity</subject><subject>Benzofuran derivatives</subject><subject>Docking study</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNp9kU2L1TAUhoMozp3RP-BCunSTmqRp04IbGfwYGHGj4C7k49SbS5pcm_Q69ef4S03nji6FA4c35zkvnLwIvaCkpoR2rw-1noyvGaGipqwmtHmEdpR3HDectI_Rjgwdwf3Av12gy5QOhFBOOH-KLtjA2l4IskO_Pzkzx5_qBFil5FIGW6U15D0UUcWxCvEEvmpxWnTKLi8boCH8Wr2zEKBSkwsRM6yXvPr7SRyXWQXc4NVjjifI-3i3HvcQynxTKsQAqVKlQnYeXNpPKjjli7b3b_HO2dIr9R1CTs_Qk1H5BM8f-hX6-v7dl-uP-Pbzh5vrt7fYNG2XcSsaSwxjoIXmnWoJIQKA9aJhvS4lhDWt5mbshg5sw6mGhtlRgO47MADNFXp19j3O8ccCKcvJJQPeqwBxSZIOYqDdwIUoKDuj5e9SmmGUx9lNal4lJXLLRh7klo3cspGUyZJNWXr54L_oCey_lb9hFODNGYBy5cnBLJNxEAxYN4PJ0kb3P_8__kqlYg</recordid><startdate>20180201</startdate><enddate>20180201</enddate><creator>Patil, Sanjeev R.</creator><creator>Bollikonda, Satyanarayana</creator><creator>Patil, Rajendra H.</creator><creator>Sangshetti, Jaiprakash N.</creator><creator>Bobade, Anil S.</creator><creator>Asrondkar, Ashish</creator><creator>Reddy, Padi Pratap</creator><creator>Shinde, Devanand B.</creator><general>Elsevier Ltd</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20180201</creationdate><title>Microwave-assisted synthesis of novel 5-substituted benzylidene amino-2-butyl benzofuran-3-yl-4-methoxyphenyl methanones as antileishmanial and antioxidant agents</title><author>Patil, Sanjeev R. ; Bollikonda, Satyanarayana ; Patil, Rajendra H. ; Sangshetti, Jaiprakash N. ; Bobade, Anil S. ; Asrondkar, Ashish ; Reddy, Padi Pratap ; Shinde, Devanand B.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c356t-573d0c22eb7b46a50007ee287328b28b77dc5b4cf696ed341be32df7eb86ecee3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>ADME properties</topic><topic>Antileishmanial activity</topic><topic>Antioxidant activity</topic><topic>Benzofuran derivatives</topic><topic>Docking study</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Patil, Sanjeev R.</creatorcontrib><creatorcontrib>Bollikonda, Satyanarayana</creatorcontrib><creatorcontrib>Patil, Rajendra H.</creatorcontrib><creatorcontrib>Sangshetti, Jaiprakash N.</creatorcontrib><creatorcontrib>Bobade, Anil S.</creatorcontrib><creatorcontrib>Asrondkar, Ashish</creatorcontrib><creatorcontrib>Reddy, Padi Pratap</creatorcontrib><creatorcontrib>Shinde, Devanand B.</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Patil, Sanjeev R.</au><au>Bollikonda, Satyanarayana</au><au>Patil, Rajendra H.</au><au>Sangshetti, Jaiprakash N.</au><au>Bobade, Anil S.</au><au>Asrondkar, Ashish</au><au>Reddy, Padi Pratap</au><au>Shinde, Devanand B.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Microwave-assisted synthesis of novel 5-substituted benzylidene amino-2-butyl benzofuran-3-yl-4-methoxyphenyl methanones as antileishmanial and antioxidant agents</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2018-02-01</date><risdate>2018</risdate><volume>28</volume><issue>3</issue><spage>482</spage><epage>487</epage><pages>482-487</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>[Display omitted]
A series of 5-substitutedbenzylideneamino-2-butylbenzofuran-3-yl-4-methoxyphenyl methanones is synthesized and evaluated for antileishmanial and antioxidant activities. Compounds 4f (IC50 = 52.0 ± 0.09 µg/ml), 4h (IC50 = 56.0 ± 0.71 µg/ml) and 4l (IC50 = 59.3 ± 0.55 µg/ml) were shown significant antileishmanial when compared with standard sodium stibogluconate (IC50 = 490.0 ± 1.5 µg/ml). Antioxidant study revealed that compounds 4i (IC50 = 2.44 ± 0.47 µg/ml) and 4l (IC50 = 3.69 ± 0.44 µg/ml) have shown potent comparable activity when compared with standard ascorbic acid (IC50 = 3.31 ± 0.34 µg/ml). Molecular docking study was carried out which replicating results of biological activity in case of initial hits 4f and 4h suggesting that these compounds have a potential to become lead molecules in drug discovery process. In silico ADME study was performed for predicting pharmacokinetic profile of the synthesised antileishmanial agents and expressed good oral drug like behaviour.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>29258770</pmid><doi>10.1016/j.bmcl.2017.12.013</doi><tpages>6</tpages></addata></record> |
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subjects | ADME properties Antileishmanial activity Antioxidant activity Benzofuran derivatives Docking study |
title | Microwave-assisted synthesis of novel 5-substituted benzylidene amino-2-butyl benzofuran-3-yl-4-methoxyphenyl methanones as antileishmanial and antioxidant agents |
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