Utilization of transition metal fluoride-based solid support catalysts for the synthesis of sulfonamides: carbonic anhydrase inhibitory activity and study
The applications of solid support catalysts in catalyzing organic reactions are well-evident. In the present study, we explored a transition metal fluoride (FeF 3 ) adsorbed on molecular sieves (4 Å) as a solid support catalyst for the preparation of sulfonamides 3a-3o . The solid support catalyst w...
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| Veröffentlicht in: | RSC advances 2022-01, Vol.12 (5), p.3165-3179 |
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| container_title | RSC advances |
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| creator | Ali, Deedar Amjad, Sayyeda Tayyeba Shafique, Zainab Naseer, Muhammad Moazzam al-Rashida, Mariya Sindhu, Tayyaba Allamgir Iftikhar, Shafia Shah, Muhammad Raza Hameed, Abdul Iqbal, Jamshed |
| description | The applications of solid support catalysts in catalyzing organic reactions are well-evident. In the present study, we explored a transition metal fluoride (FeF
3
) adsorbed on molecular sieves (4 Å) as a solid support catalyst for the preparation of sulfonamides
3a-3o
. The solid support catalyst was characterized
via
X-ray diffraction and AFM analysis. The catalyst was further explored for the synthesis of indoles
6a-h
, 1H-tetrazoles and 1,4-dihydropyridines. The sulfonamides prepared herein were investigated for their potential to inhibit carbonic anhydrase (hCA II, hCA IX and hCA XII). All compounds were found to be active inhibitors with IC
50
values in the low micromolar range. Some compounds were even found to be highly selective inhibitors. Compound
3i
only inhibited hCA II (IC
50
= 2.76 ± 1.1 μM) and had |
| doi_str_mv | 10.1039/d1ra07844e |
| format | Article |
| fullrecord | <record><control><sourceid>rsc</sourceid><recordid>TN_cdi_rsc_primary_d1ra07844e</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>d1ra07844e</sourcerecordid><originalsourceid>FETCH-rsc_primary_d1ra07844e3</originalsourceid><addsrcrecordid>eNqFj8FKxEAMhgdBcNG97F3IC1RnurW6XkXxAfS8pO2URqYzJUmF8VF8WkcRPJpD_oT8_wcxZufslbP7w_XgGO3tXdP4E7OpbdNWtW0PZ2Yr8mZLtTeubt3GfL4qBfpApRQhjaCMUehnm71igDGsiWnwVYfiB5AUqPR1WRIr9FgsWVRgTAw6eZAciwjJN0zWMKaIc4nLfTFzlyL1gHHKAxccUJyoI02cAXuld9IyxMLXdcgX5nTEIH77q-fm8unx5eG5YumPC9OMnI9_f-7_u38BgCldZw</addsrcrecordid><sourcetype>Publisher</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Utilization of transition metal fluoride-based solid support catalysts for the synthesis of sulfonamides: carbonic anhydrase inhibitory activity and study</title><source>DOAJ Directory of Open Access Journals</source><source>Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals</source><source>PubMed Central Open Access</source><source>PubMed Central</source><creator>Ali, Deedar ; Amjad, Sayyeda Tayyeba ; Shafique, Zainab ; Naseer, Muhammad Moazzam ; al-Rashida, Mariya ; Sindhu, Tayyaba Allamgir ; Iftikhar, Shafia ; Shah, Muhammad Raza ; Hameed, Abdul ; Iqbal, Jamshed</creator><creatorcontrib>Ali, Deedar ; Amjad, Sayyeda Tayyeba ; Shafique, Zainab ; Naseer, Muhammad Moazzam ; al-Rashida, Mariya ; Sindhu, Tayyaba Allamgir ; Iftikhar, Shafia ; Shah, Muhammad Raza ; Hameed, Abdul ; Iqbal, Jamshed</creatorcontrib><description>The applications of solid support catalysts in catalyzing organic reactions are well-evident. In the present study, we explored a transition metal fluoride (FeF
3
) adsorbed on molecular sieves (4 Å) as a solid support catalyst for the preparation of sulfonamides
3a-3o
. The solid support catalyst was characterized
via
X-ray diffraction and AFM analysis. The catalyst was further explored for the synthesis of indoles
6a-h
, 1H-tetrazoles and 1,4-dihydropyridines. The sulfonamides prepared herein were investigated for their potential to inhibit carbonic anhydrase (hCA II, hCA IX and hCA XII). All compounds were found to be active inhibitors with IC
50
values in the low micromolar range. Some compounds were even found to be highly selective inhibitors. Compound
3i
only inhibited hCA II (IC
50
= 2.76 ± 1.1 μM) and had <27% inhibition against hCA IX and hCA XII. Similarly,
3e
(IC
50
= 0.63 ± 0.14 μM) only inhibited hCA XII and showed <31% inhibition against hCA II and hCA IX. Molecular docking studies were carried out to rationalize the ligand-binding site interactions. Given the lack of selective CA inhibitors, compounds
3e
and
3i
can provide significant leads for the further development of highly selective CA inhibitors.
The applications of solid support catalysts in catalyzing organic reactions are well-evident.</description><identifier>EISSN: 2046-2069</identifier><identifier>DOI: 10.1039/d1ra07844e</identifier><ispartof>RSC advances, 2022-01, Vol.12 (5), p.3165-3179</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,778,782,862,27911,27912</link.rule.ids></links><search><creatorcontrib>Ali, Deedar</creatorcontrib><creatorcontrib>Amjad, Sayyeda Tayyeba</creatorcontrib><creatorcontrib>Shafique, Zainab</creatorcontrib><creatorcontrib>Naseer, Muhammad Moazzam</creatorcontrib><creatorcontrib>al-Rashida, Mariya</creatorcontrib><creatorcontrib>Sindhu, Tayyaba Allamgir</creatorcontrib><creatorcontrib>Iftikhar, Shafia</creatorcontrib><creatorcontrib>Shah, Muhammad Raza</creatorcontrib><creatorcontrib>Hameed, Abdul</creatorcontrib><creatorcontrib>Iqbal, Jamshed</creatorcontrib><title>Utilization of transition metal fluoride-based solid support catalysts for the synthesis of sulfonamides: carbonic anhydrase inhibitory activity and study</title><title>RSC advances</title><description>The applications of solid support catalysts in catalyzing organic reactions are well-evident. In the present study, we explored a transition metal fluoride (FeF
3
) adsorbed on molecular sieves (4 Å) as a solid support catalyst for the preparation of sulfonamides
3a-3o
. The solid support catalyst was characterized
via
X-ray diffraction and AFM analysis. The catalyst was further explored for the synthesis of indoles
6a-h
, 1H-tetrazoles and 1,4-dihydropyridines. The sulfonamides prepared herein were investigated for their potential to inhibit carbonic anhydrase (hCA II, hCA IX and hCA XII). All compounds were found to be active inhibitors with IC
50
values in the low micromolar range. Some compounds were even found to be highly selective inhibitors. Compound
3i
only inhibited hCA II (IC
50
= 2.76 ± 1.1 μM) and had <27% inhibition against hCA IX and hCA XII. Similarly,
3e
(IC
50
= 0.63 ± 0.14 μM) only inhibited hCA XII and showed <31% inhibition against hCA II and hCA IX. Molecular docking studies were carried out to rationalize the ligand-binding site interactions. Given the lack of selective CA inhibitors, compounds
3e
and
3i
can provide significant leads for the further development of highly selective CA inhibitors.
The applications of solid support catalysts in catalyzing organic reactions are well-evident.</description><issn>2046-2069</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNqFj8FKxEAMhgdBcNG97F3IC1RnurW6XkXxAfS8pO2URqYzJUmF8VF8WkcRPJpD_oT8_wcxZufslbP7w_XgGO3tXdP4E7OpbdNWtW0PZ2Yr8mZLtTeubt3GfL4qBfpApRQhjaCMUehnm71igDGsiWnwVYfiB5AUqPR1WRIr9FgsWVRgTAw6eZAciwjJN0zWMKaIc4nLfTFzlyL1gHHKAxccUJyoI02cAXuld9IyxMLXdcgX5nTEIH77q-fm8unx5eG5YumPC9OMnI9_f-7_u38BgCldZw</recordid><startdate>20220124</startdate><enddate>20220124</enddate><creator>Ali, Deedar</creator><creator>Amjad, Sayyeda Tayyeba</creator><creator>Shafique, Zainab</creator><creator>Naseer, Muhammad Moazzam</creator><creator>al-Rashida, Mariya</creator><creator>Sindhu, Tayyaba Allamgir</creator><creator>Iftikhar, Shafia</creator><creator>Shah, Muhammad Raza</creator><creator>Hameed, Abdul</creator><creator>Iqbal, Jamshed</creator><scope/></search><sort><creationdate>20220124</creationdate><title>Utilization of transition metal fluoride-based solid support catalysts for the synthesis of sulfonamides: carbonic anhydrase inhibitory activity and study</title><author>Ali, Deedar ; Amjad, Sayyeda Tayyeba ; Shafique, Zainab ; Naseer, Muhammad Moazzam ; al-Rashida, Mariya ; Sindhu, Tayyaba Allamgir ; Iftikhar, Shafia ; Shah, Muhammad Raza ; Hameed, Abdul ; Iqbal, Jamshed</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-rsc_primary_d1ra07844e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><creationdate>2022</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ali, Deedar</creatorcontrib><creatorcontrib>Amjad, Sayyeda Tayyeba</creatorcontrib><creatorcontrib>Shafique, Zainab</creatorcontrib><creatorcontrib>Naseer, Muhammad Moazzam</creatorcontrib><creatorcontrib>al-Rashida, Mariya</creatorcontrib><creatorcontrib>Sindhu, Tayyaba Allamgir</creatorcontrib><creatorcontrib>Iftikhar, Shafia</creatorcontrib><creatorcontrib>Shah, Muhammad Raza</creatorcontrib><creatorcontrib>Hameed, Abdul</creatorcontrib><creatorcontrib>Iqbal, Jamshed</creatorcontrib><jtitle>RSC advances</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ali, Deedar</au><au>Amjad, Sayyeda Tayyeba</au><au>Shafique, Zainab</au><au>Naseer, Muhammad Moazzam</au><au>al-Rashida, Mariya</au><au>Sindhu, Tayyaba Allamgir</au><au>Iftikhar, Shafia</au><au>Shah, Muhammad Raza</au><au>Hameed, Abdul</au><au>Iqbal, Jamshed</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Utilization of transition metal fluoride-based solid support catalysts for the synthesis of sulfonamides: carbonic anhydrase inhibitory activity and study</atitle><jtitle>RSC advances</jtitle><date>2022-01-24</date><risdate>2022</risdate><volume>12</volume><issue>5</issue><spage>3165</spage><epage>3179</epage><pages>3165-3179</pages><eissn>2046-2069</eissn><abstract>The applications of solid support catalysts in catalyzing organic reactions are well-evident. In the present study, we explored a transition metal fluoride (FeF
3
) adsorbed on molecular sieves (4 Å) as a solid support catalyst for the preparation of sulfonamides
3a-3o
. The solid support catalyst was characterized
via
X-ray diffraction and AFM analysis. The catalyst was further explored for the synthesis of indoles
6a-h
, 1H-tetrazoles and 1,4-dihydropyridines. The sulfonamides prepared herein were investigated for their potential to inhibit carbonic anhydrase (hCA II, hCA IX and hCA XII). All compounds were found to be active inhibitors with IC
50
values in the low micromolar range. Some compounds were even found to be highly selective inhibitors. Compound
3i
only inhibited hCA II (IC
50
= 2.76 ± 1.1 μM) and had <27% inhibition against hCA IX and hCA XII. Similarly,
3e
(IC
50
= 0.63 ± 0.14 μM) only inhibited hCA XII and showed <31% inhibition against hCA II and hCA IX. Molecular docking studies were carried out to rationalize the ligand-binding site interactions. Given the lack of selective CA inhibitors, compounds
3e
and
3i
can provide significant leads for the further development of highly selective CA inhibitors.
The applications of solid support catalysts in catalyzing organic reactions are well-evident.</abstract><doi>10.1039/d1ra07844e</doi><tpages>15</tpages></addata></record> |
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| source | DOAJ Directory of Open Access Journals; Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; PubMed Central Open Access; PubMed Central |
| title | Utilization of transition metal fluoride-based solid support catalysts for the synthesis of sulfonamides: carbonic anhydrase inhibitory activity and study |
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