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Synthesis, Antimicrobial Evaluation, and Computational Study of Novel Fluorinated Benzofuran Derivatives
Objective: A series of novel fluorine containing ( Z )-5-chloro-2-(4-fluorobenzylidene)-4,6-dimethylbenzofuran-3(2 H )-one ( IVa–IVe ) and ( E )-(5-chloro-3-(4-fluorostyryl)-4,6-dimethylbenzofuran-2-yl)(4-chlorophenyl)methanone derivatives ( Va–Ve ) have been synthesized by using ( E )-1-(3-chloro-6...
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| Published in: | Russian journal of bioorganic chemistry 2024-10, Vol.50 (5), p.1710-1723 |
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| Main Authors: | , , , , , , |
| Format: | Article |
| Language: | English |
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| container_end_page | 1723 |
| container_issue | 5 |
| container_start_page | 1710 |
| container_title | Russian journal of bioorganic chemistry |
| container_volume | 50 |
| creator | Dengale, S. G. Deshmukh, K. K. Akolkar, H. N. Darekar, N. R. Shaikh, M. H. Khedkar, V. M. Kasar, S. D. |
| description | Objective:
A series of novel fluorine containing (
Z
)-5-chloro-2-(4-fluorobenzylidene)-4,6-dimethylbenzofuran-3(2
H
)-one (
IVa–IVe
) and (
E
)-(5-chloro-3-(4-fluorostyryl)-4,6-dimethylbenzofuran-2-yl)(4-chlorophenyl)methanone derivatives (
Va–Ve
) have been synthesized by using (
E
)-1-(3-chloro-6-hydroxy-2,4-dimethylphenyl)-3-(4-fluorophenyl)prop-2-en-1-one (
IIIa–IIIe
).
Methods:
The formation of the synthesized compounds was confirmed by IR,
1
H,
13
C NMR, and mass spectral data. All synthesized compounds were screened for their antimicrobial activity.
Results and Discussion:
Most of the synthesized compounds have shown better antimicrobial activity as compared to standard drug. Molecular docking study against DNA gyrase could provide insights into binding modes and affinities. The binding affinity data was found to be in harmony with the experimental antimicrobial activities.
Conclusions:
Furthermore, analysis of the drug-like properties produced good results qualifying these leads as oral drug candidates. |
| doi_str_mv | 10.1134/S1068162024050194 |
| format | article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_3115023817</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>3115023817</sourcerecordid><originalsourceid>FETCH-LOGICAL-c198t-3d506ac00774087834f9c8fb43c03c8699ac8b2fc9d85ac8db19a43e5fc559403</originalsourceid><addsrcrecordid>eNp1UM9LwzAUDqLgnP4B3gJeV31p0i45zrmpMPQwBW8lTRPX0TUzSQvzrzdzggfx9D7e94P3PoQuCVwTQtnNkkDOSZ5CyiADItgRGpAceEIpvB1HHOlkz5-iM-_XAAQg4wO0Wu7asNK-9iM8aUO9qZWzZS0bPOtl08lQ23aEZVvhqd1su_C9iOwydNUOW4OfbK8bPG866-pWBl3hW91-WtM52eI77eo-Wnrtz9GJkY3XFz9ziF7ns5fpQ7J4vn-cThaJIoKHhFYZ5FIBjMcM-JhTZoTipmRUAVU8F0IqXqZGiYpnEVYlEZJRnRmVZYIBHaKrQ-7W2Y9O-1Csbefiyb6ghGSQUk7GUUUOqvit906bYuvqjXS7gkCxL7T4U2j0pAePj9r2Xbvf5P9NXyg-eFs</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>3115023817</pqid></control><display><type>article</type><title>Synthesis, Antimicrobial Evaluation, and Computational Study of Novel Fluorinated Benzofuran Derivatives</title><source>Springer Nature</source><creator>Dengale, S. G. ; Deshmukh, K. K. ; Akolkar, H. N. ; Darekar, N. R. ; Shaikh, M. H. ; Khedkar, V. M. ; Kasar, S. D.</creator><creatorcontrib>Dengale, S. G. ; Deshmukh, K. K. ; Akolkar, H. N. ; Darekar, N. R. ; Shaikh, M. H. ; Khedkar, V. M. ; Kasar, S. D.</creatorcontrib><description>Objective:
A series of novel fluorine containing (
Z
)-5-chloro-2-(4-fluorobenzylidene)-4,6-dimethylbenzofuran-3(2
H
)-one (
IVa–IVe
) and (
E
)-(5-chloro-3-(4-fluorostyryl)-4,6-dimethylbenzofuran-2-yl)(4-chlorophenyl)methanone derivatives (
Va–Ve
) have been synthesized by using (
E
)-1-(3-chloro-6-hydroxy-2,4-dimethylphenyl)-3-(4-fluorophenyl)prop-2-en-1-one (
IIIa–IIIe
).
Methods:
The formation of the synthesized compounds was confirmed by IR,
1
H,
13
C NMR, and mass spectral data. All synthesized compounds were screened for their antimicrobial activity.
Results and Discussion:
Most of the synthesized compounds have shown better antimicrobial activity as compared to standard drug. Molecular docking study against DNA gyrase could provide insights into binding modes and affinities. The binding affinity data was found to be in harmony with the experimental antimicrobial activities.
Conclusions:
Furthermore, analysis of the drug-like properties produced good results qualifying these leads as oral drug candidates.</description><identifier>ISSN: 1068-1620</identifier><identifier>EISSN: 1608-330X</identifier><identifier>DOI: 10.1134/S1068162024050194</identifier><language>eng</language><publisher>Moscow: Pleiades Publishing</publisher><subject>Affinity ; Binding ; Biochemistry ; Biomedical and Life Sciences ; Biomedicine ; Bioorganic Chemistry ; Chemical synthesis ; Fluorine ; Life Sciences ; Molecular docking ; NMR ; Nuclear magnetic resonance ; Organic Chemistry</subject><ispartof>Russian journal of bioorganic chemistry, 2024-10, Vol.50 (5), p.1710-1723</ispartof><rights>Pleiades Publishing, Ltd. 2024</rights><rights>Pleiades Publishing, Ltd. 2024.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c198t-3d506ac00774087834f9c8fb43c03c8699ac8b2fc9d85ac8db19a43e5fc559403</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,778,782,27911,27912</link.rule.ids></links><search><creatorcontrib>Dengale, S. G.</creatorcontrib><creatorcontrib>Deshmukh, K. K.</creatorcontrib><creatorcontrib>Akolkar, H. N.</creatorcontrib><creatorcontrib>Darekar, N. R.</creatorcontrib><creatorcontrib>Shaikh, M. H.</creatorcontrib><creatorcontrib>Khedkar, V. M.</creatorcontrib><creatorcontrib>Kasar, S. D.</creatorcontrib><title>Synthesis, Antimicrobial Evaluation, and Computational Study of Novel Fluorinated Benzofuran Derivatives</title><title>Russian journal of bioorganic chemistry</title><addtitle>Russ J Bioorg Chem</addtitle><description>Objective:
A series of novel fluorine containing (
Z
)-5-chloro-2-(4-fluorobenzylidene)-4,6-dimethylbenzofuran-3(2
H
)-one (
IVa–IVe
) and (
E
)-(5-chloro-3-(4-fluorostyryl)-4,6-dimethylbenzofuran-2-yl)(4-chlorophenyl)methanone derivatives (
Va–Ve
) have been synthesized by using (
E
)-1-(3-chloro-6-hydroxy-2,4-dimethylphenyl)-3-(4-fluorophenyl)prop-2-en-1-one (
IIIa–IIIe
).
Methods:
The formation of the synthesized compounds was confirmed by IR,
1
H,
13
C NMR, and mass spectral data. All synthesized compounds were screened for their antimicrobial activity.
Results and Discussion:
Most of the synthesized compounds have shown better antimicrobial activity as compared to standard drug. Molecular docking study against DNA gyrase could provide insights into binding modes and affinities. The binding affinity data was found to be in harmony with the experimental antimicrobial activities.
Conclusions:
Furthermore, analysis of the drug-like properties produced good results qualifying these leads as oral drug candidates.</description><subject>Affinity</subject><subject>Binding</subject><subject>Biochemistry</subject><subject>Biomedical and Life Sciences</subject><subject>Biomedicine</subject><subject>Bioorganic Chemistry</subject><subject>Chemical synthesis</subject><subject>Fluorine</subject><subject>Life Sciences</subject><subject>Molecular docking</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Organic Chemistry</subject><issn>1068-1620</issn><issn>1608-330X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNp1UM9LwzAUDqLgnP4B3gJeV31p0i45zrmpMPQwBW8lTRPX0TUzSQvzrzdzggfx9D7e94P3PoQuCVwTQtnNkkDOSZ5CyiADItgRGpAceEIpvB1HHOlkz5-iM-_XAAQg4wO0Wu7asNK-9iM8aUO9qZWzZS0bPOtl08lQ23aEZVvhqd1su_C9iOwydNUOW4OfbK8bPG866-pWBl3hW91-WtM52eI77eo-Wnrtz9GJkY3XFz9ziF7ns5fpQ7J4vn-cThaJIoKHhFYZ5FIBjMcM-JhTZoTipmRUAVU8F0IqXqZGiYpnEVYlEZJRnRmVZYIBHaKrQ-7W2Y9O-1Csbefiyb6ghGSQUk7GUUUOqvit906bYuvqjXS7gkCxL7T4U2j0pAePj9r2Xbvf5P9NXyg-eFs</recordid><startdate>20241001</startdate><enddate>20241001</enddate><creator>Dengale, S. G.</creator><creator>Deshmukh, K. K.</creator><creator>Akolkar, H. N.</creator><creator>Darekar, N. R.</creator><creator>Shaikh, M. H.</creator><creator>Khedkar, V. M.</creator><creator>Kasar, S. D.</creator><general>Pleiades Publishing</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20241001</creationdate><title>Synthesis, Antimicrobial Evaluation, and Computational Study of Novel Fluorinated Benzofuran Derivatives</title><author>Dengale, S. G. ; Deshmukh, K. K. ; Akolkar, H. N. ; Darekar, N. R. ; Shaikh, M. H. ; Khedkar, V. M. ; Kasar, S. D.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c198t-3d506ac00774087834f9c8fb43c03c8699ac8b2fc9d85ac8db19a43e5fc559403</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Affinity</topic><topic>Binding</topic><topic>Biochemistry</topic><topic>Biomedical and Life Sciences</topic><topic>Biomedicine</topic><topic>Bioorganic Chemistry</topic><topic>Chemical synthesis</topic><topic>Fluorine</topic><topic>Life Sciences</topic><topic>Molecular docking</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Organic Chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dengale, S. G.</creatorcontrib><creatorcontrib>Deshmukh, K. K.</creatorcontrib><creatorcontrib>Akolkar, H. N.</creatorcontrib><creatorcontrib>Darekar, N. R.</creatorcontrib><creatorcontrib>Shaikh, M. H.</creatorcontrib><creatorcontrib>Khedkar, V. M.</creatorcontrib><creatorcontrib>Kasar, S. D.</creatorcontrib><collection>CrossRef</collection><jtitle>Russian journal of bioorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dengale, S. G.</au><au>Deshmukh, K. K.</au><au>Akolkar, H. N.</au><au>Darekar, N. R.</au><au>Shaikh, M. H.</au><au>Khedkar, V. M.</au><au>Kasar, S. D.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, Antimicrobial Evaluation, and Computational Study of Novel Fluorinated Benzofuran Derivatives</atitle><jtitle>Russian journal of bioorganic chemistry</jtitle><stitle>Russ J Bioorg Chem</stitle><date>2024-10-01</date><risdate>2024</risdate><volume>50</volume><issue>5</issue><spage>1710</spage><epage>1723</epage><pages>1710-1723</pages><issn>1068-1620</issn><eissn>1608-330X</eissn><abstract>Objective:
A series of novel fluorine containing (
Z
)-5-chloro-2-(4-fluorobenzylidene)-4,6-dimethylbenzofuran-3(2
H
)-one (
IVa–IVe
) and (
E
)-(5-chloro-3-(4-fluorostyryl)-4,6-dimethylbenzofuran-2-yl)(4-chlorophenyl)methanone derivatives (
Va–Ve
) have been synthesized by using (
E
)-1-(3-chloro-6-hydroxy-2,4-dimethylphenyl)-3-(4-fluorophenyl)prop-2-en-1-one (
IIIa–IIIe
).
Methods:
The formation of the synthesized compounds was confirmed by IR,
1
H,
13
C NMR, and mass spectral data. All synthesized compounds were screened for their antimicrobial activity.
Results and Discussion:
Most of the synthesized compounds have shown better antimicrobial activity as compared to standard drug. Molecular docking study against DNA gyrase could provide insights into binding modes and affinities. The binding affinity data was found to be in harmony with the experimental antimicrobial activities.
Conclusions:
Furthermore, analysis of the drug-like properties produced good results qualifying these leads as oral drug candidates.</abstract><cop>Moscow</cop><pub>Pleiades Publishing</pub><doi>10.1134/S1068162024050194</doi><tpages>14</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1068-1620 |
| ispartof | Russian journal of bioorganic chemistry, 2024-10, Vol.50 (5), p.1710-1723 |
| issn | 1068-1620 1608-330X |
| language | eng |
| recordid | cdi_proquest_journals_3115023817 |
| source | Springer Nature |
| subjects | Affinity Binding Biochemistry Biomedical and Life Sciences Biomedicine Bioorganic Chemistry Chemical synthesis Fluorine Life Sciences Molecular docking NMR Nuclear magnetic resonance Organic Chemistry |
| title | Synthesis, Antimicrobial Evaluation, and Computational Study of Novel Fluorinated Benzofuran Derivatives |
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