Microwave Assisted Synthesis of Benzo-Azacrown Ethers and In Vitro Inhibition Studies on hCA I–II
In this study, macro-ringed benzo-aza-oxa-crown ethers were synthesized by a cyclization reaction between 2,2′-dithiodianiline and mono/di/tri/tetraethylene glycol dichloride/dibromide with Cs 2 CO 3 as a catalyst under nitrogen atmosphere by the S N 2 mechanism using the microwave synthesis method,...
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| Veröffentlicht in: | Russian journal of general chemistry 2023-02, Vol.93 (2), p.440-448 |
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| creator | Sapmaz, A. Çalışır, Ü. Akkemik, E. Çiçek, B. |
| description | In this study, macro-ringed benzo-aza-oxa-crown ethers were synthesized by a cyclization reaction between 2,2′-dithiodianiline and mono/di/tri/tetraethylene glycol dichloride/dibromide with Cs
2
CO
3
as a catalyst under nitrogen atmosphere by the S
N
2 mechanism using the microwave synthesis method, which is one of the green chemistry methods. Structural characterizations of the original 2,2′-dithiodibenzo crown ether derivatives were confirmed with melting point, FT-IR,
1
H NMR,
13
C NMR, LC-MS/MS, elemental analysis, UV and fluorescence spectroscopy methods. In addition, the inhibition effects of these synthesized four crown ethers on human erythrocyte carbonic anhydrase (hCA I–II) isoenzyme activities were investigated. The synthesized compounds include aromatic benzene rings, nitrogen, sulfur, and oxygen donor atoms. The effects of aromaticity,
S
,
S
′-disulfide bond, nitrogen and oxygen donor atoms on the activity of carbonic anhydrase isoenzyme have been studied. (1,8,11,18)-Tetraaza[2,3-6,7-12,13-16,17]tetrabenzo-(4,5,14,15)-tetrathiocycloeicosane showed the highest inhibition effect on hCA I (
K
i
= 0.353±0.154 µM) and hCA II (
K
i
= 1.588±0.998 µM) enzyme. |
| doi_str_mv | 10.1134/S1070363223020275 |
| format | Article |
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2
CO
3
as a catalyst under nitrogen atmosphere by the S
N
2 mechanism using the microwave synthesis method, which is one of the green chemistry methods. Structural characterizations of the original 2,2′-dithiodibenzo crown ether derivatives were confirmed with melting point, FT-IR,
1
H NMR,
13
C NMR, LC-MS/MS, elemental analysis, UV and fluorescence spectroscopy methods. In addition, the inhibition effects of these synthesized four crown ethers on human erythrocyte carbonic anhydrase (hCA I–II) isoenzyme activities were investigated. The synthesized compounds include aromatic benzene rings, nitrogen, sulfur, and oxygen donor atoms. The effects of aromaticity,
S
,
S
′-disulfide bond, nitrogen and oxygen donor atoms on the activity of carbonic anhydrase isoenzyme have been studied. (1,8,11,18)-Tetraaza[2,3-6,7-12,13-16,17]tetrabenzo-(4,5,14,15)-tetrathiocycloeicosane showed the highest inhibition effect on hCA I (
K
i
= 0.353±0.154 µM) and hCA II (
K
i
= 1.588±0.998 µM) enzyme.</description><identifier>ISSN: 1070-3632</identifier><identifier>EISSN: 1608-3350</identifier><identifier>DOI: 10.1134/S1070363223020275</identifier><language>eng</language><publisher>Moscow: Pleiades Publishing</publisher><subject>Aromatic compounds ; Aromaticity ; Benzene ; Carbonic anhydrase ; Chemical analysis ; Chemical synthesis ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; Crown ethers ; Dichlorides ; Enzymes ; Fluorescence ; Fluorescence spectroscopy ; Melting points ; Nitrogen ; NMR ; Nuclear magnetic resonance ; Oxygen</subject><ispartof>Russian journal of general chemistry, 2023-02, Vol.93 (2), p.440-448</ispartof><rights>Pleiades Publishing, Ltd. 2023</rights><rights>COPYRIGHT 2023 Springer</rights><rights>Pleiades Publishing, Ltd. 2023.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c355t-21752bce822e2bf05f3e0da42fcc2c584e08542e76de1aef2d7990df1bc5ea413</citedby><cites>FETCH-LOGICAL-c355t-21752bce822e2bf05f3e0da42fcc2c584e08542e76de1aef2d7990df1bc5ea413</cites><orcidid>0000-0002-2610-0523 ; 0000-0002-4177-4884</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1134/S1070363223020275$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1134/S1070363223020275$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27923,27924,41487,42556,51318</link.rule.ids></links><search><creatorcontrib>Sapmaz, A.</creatorcontrib><creatorcontrib>Çalışır, Ü.</creatorcontrib><creatorcontrib>Akkemik, E.</creatorcontrib><creatorcontrib>Çiçek, B.</creatorcontrib><title>Microwave Assisted Synthesis of Benzo-Azacrown Ethers and In Vitro Inhibition Studies on hCA I–II</title><title>Russian journal of general chemistry</title><addtitle>Russ J Gen Chem</addtitle><description>In this study, macro-ringed benzo-aza-oxa-crown ethers were synthesized by a cyclization reaction between 2,2′-dithiodianiline and mono/di/tri/tetraethylene glycol dichloride/dibromide with Cs
2
CO
3
as a catalyst under nitrogen atmosphere by the S
N
2 mechanism using the microwave synthesis method, which is one of the green chemistry methods. Structural characterizations of the original 2,2′-dithiodibenzo crown ether derivatives were confirmed with melting point, FT-IR,
1
H NMR,
13
C NMR, LC-MS/MS, elemental analysis, UV and fluorescence spectroscopy methods. In addition, the inhibition effects of these synthesized four crown ethers on human erythrocyte carbonic anhydrase (hCA I–II) isoenzyme activities were investigated. The synthesized compounds include aromatic benzene rings, nitrogen, sulfur, and oxygen donor atoms. The effects of aromaticity,
S
,
S
′-disulfide bond, nitrogen and oxygen donor atoms on the activity of carbonic anhydrase isoenzyme have been studied. (1,8,11,18)-Tetraaza[2,3-6,7-12,13-16,17]tetrabenzo-(4,5,14,15)-tetrathiocycloeicosane showed the highest inhibition effect on hCA I (
K
i
= 0.353±0.154 µM) and hCA II (
K
i
= 1.588±0.998 µM) enzyme.</description><subject>Aromatic compounds</subject><subject>Aromaticity</subject><subject>Benzene</subject><subject>Carbonic anhydrase</subject><subject>Chemical analysis</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>Crown ethers</subject><subject>Dichlorides</subject><subject>Enzymes</subject><subject>Fluorescence</subject><subject>Fluorescence spectroscopy</subject><subject>Melting points</subject><subject>Nitrogen</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Oxygen</subject><issn>1070-3632</issn><issn>1608-3350</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNp1kE1OwzAQhSMEElA4ADtLrAPjcZy0y1DxE6mIRYFt5DpjatTaYKcgWHEHbshJcFUkFgh54fG8941HL8uOOJxwLorTKYcKRCkQBSBgJbeyPV7CMBdCwnaqk5yv9d1sP8ZHAA5Q4l6mr60O_lW9EKtjtLGnjk3fXD-n9GDesDNy7z6v39Xa5th5UkJkynWsceze9sGnYm5ntrfesWm_6iwl0LH5uGbN18dn0xxkO0YtIh3-3IPs7uL8dnyVT24um3E9ybWQss-RVxJnmoaIhDMD0giCThVotEYthwXBUBZIVdkRV2Swq0Yj6AyfaUmq4GKQHW_mPgX_vKLYt49-FVz6shUcy5HAqpTJdbJxPagFtdYZ3wel0-loabV3ZGzq11UhqgJKKBLAN0BKIMZApn0KdqnCW8uhXYff_gk_MbhhYvK6Bwq_q_wPfQOgDYXt</recordid><startdate>20230201</startdate><enddate>20230201</enddate><creator>Sapmaz, A.</creator><creator>Çalışır, Ü.</creator><creator>Akkemik, E.</creator><creator>Çiçek, B.</creator><general>Pleiades Publishing</general><general>Springer</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-2610-0523</orcidid><orcidid>https://orcid.org/0000-0002-4177-4884</orcidid></search><sort><creationdate>20230201</creationdate><title>Microwave Assisted Synthesis of Benzo-Azacrown Ethers and In Vitro Inhibition Studies on hCA I–II</title><author>Sapmaz, A. ; Çalışır, Ü. ; Akkemik, E. ; Çiçek, B.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c355t-21752bce822e2bf05f3e0da42fcc2c584e08542e76de1aef2d7990df1bc5ea413</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Aromatic compounds</topic><topic>Aromaticity</topic><topic>Benzene</topic><topic>Carbonic anhydrase</topic><topic>Chemical analysis</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>Crown ethers</topic><topic>Dichlorides</topic><topic>Enzymes</topic><topic>Fluorescence</topic><topic>Fluorescence spectroscopy</topic><topic>Melting points</topic><topic>Nitrogen</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Oxygen</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sapmaz, A.</creatorcontrib><creatorcontrib>Çalışır, Ü.</creatorcontrib><creatorcontrib>Akkemik, E.</creatorcontrib><creatorcontrib>Çiçek, B.</creatorcontrib><collection>CrossRef</collection><jtitle>Russian journal of general chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sapmaz, A.</au><au>Çalışır, Ü.</au><au>Akkemik, E.</au><au>Çiçek, B.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Microwave Assisted Synthesis of Benzo-Azacrown Ethers and In Vitro Inhibition Studies on hCA I–II</atitle><jtitle>Russian journal of general chemistry</jtitle><stitle>Russ J Gen Chem</stitle><date>2023-02-01</date><risdate>2023</risdate><volume>93</volume><issue>2</issue><spage>440</spage><epage>448</epage><pages>440-448</pages><issn>1070-3632</issn><eissn>1608-3350</eissn><abstract>In this study, macro-ringed benzo-aza-oxa-crown ethers were synthesized by a cyclization reaction between 2,2′-dithiodianiline and mono/di/tri/tetraethylene glycol dichloride/dibromide with Cs
2
CO
3
as a catalyst under nitrogen atmosphere by the S
N
2 mechanism using the microwave synthesis method, which is one of the green chemistry methods. Structural characterizations of the original 2,2′-dithiodibenzo crown ether derivatives were confirmed with melting point, FT-IR,
1
H NMR,
13
C NMR, LC-MS/MS, elemental analysis, UV and fluorescence spectroscopy methods. In addition, the inhibition effects of these synthesized four crown ethers on human erythrocyte carbonic anhydrase (hCA I–II) isoenzyme activities were investigated. The synthesized compounds include aromatic benzene rings, nitrogen, sulfur, and oxygen donor atoms. The effects of aromaticity,
S
,
S
′-disulfide bond, nitrogen and oxygen donor atoms on the activity of carbonic anhydrase isoenzyme have been studied. (1,8,11,18)-Tetraaza[2,3-6,7-12,13-16,17]tetrabenzo-(4,5,14,15)-tetrathiocycloeicosane showed the highest inhibition effect on hCA I (
K
i
= 0.353±0.154 µM) and hCA II (
K
i
= 1.588±0.998 µM) enzyme.</abstract><cop>Moscow</cop><pub>Pleiades Publishing</pub><doi>10.1134/S1070363223020275</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0002-2610-0523</orcidid><orcidid>https://orcid.org/0000-0002-4177-4884</orcidid></addata></record> |
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| language | eng |
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| subjects | Aromatic compounds Aromaticity Benzene Carbonic anhydrase Chemical analysis Chemical synthesis Chemistry Chemistry and Materials Science Chemistry/Food Science Crown ethers Dichlorides Enzymes Fluorescence Fluorescence spectroscopy Melting points Nitrogen NMR Nuclear magnetic resonance Oxygen |
| title | Microwave Assisted Synthesis of Benzo-Azacrown Ethers and In Vitro Inhibition Studies on hCA I–II |
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