Nano-CuFe 2 O 3 -catalyzed green synthesis of novel quinazolinone-tetrazole hybrids as anti-cancer agents
A novel green protocol has been developed for the synthesis of quinazolinone-tetrazole conjugates (7a-g, 8a-g and 9a-g) using recyclable nano-CuFe O catalyst in water. Initially, 2-mercapto-3-substituted phenethylquinazolin-4(3H)-one (5a-c) was prepared by using nano-CuFe O catalyst in water. Then,...
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| Veröffentlicht in: | Molecular diversity 2023-02, Vol.27 (1), p.425 |
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| creator | Kommula, Dileep Chintakunta, Praveen Kumar Garikapati, Koteswararao Murty, M S R |
| description | A novel green protocol has been developed for the synthesis of quinazolinone-tetrazole conjugates (7a-g, 8a-g and 9a-g) using recyclable nano-CuFe
O
catalyst in water. Initially, 2-mercapto-3-substituted phenethylquinazolin-4(3H)-one (5a-c) was prepared by using nano-CuFe
O
catalyst in water. Then, compounds (5a-c) were reacted with 1-bromo-3-chloropropane under nano-CuFe
O
catalyst in water solvent to give S-alkylated quinazolinone core intermediate (6a-c), which was subsequently reacted with 1-substituted-1H-tetrazole-5-thiol (2a-g) by employing the similar reaction conditions to afford the final target compounds. The regioselective formation of C-S bond was unambiguously confirmed by single-crystal X-ray diffraction. The anti-cancer activity of the derivatives on various cancer cell lines such as SIHA, MD-AMB-231 and HepG2 was evaluated. Remarkably, compounds, 7f, 8f, 9a, 9d and 9f, showed potent activity in MD-AMB-231 cancer cell line (IC
: 9.13-10.3 µM), while the same derivatives showed significant potent activity in SiHa and HepG2 cancer cell lines (IC
: 17.46-27.0 µM). Most significantly, compound 7o (IC
: 8.15 µM) showed potent activity, compared to the drug etoposide (IC
: 18.11 µM) against MD-AMB-231 cell line. Flow cytometry analysis revealed that compounds 7f, 8f, 9a, 9d and 9f arrested the cell growth in the G1 phase in MD-AMB-231 cell line. |
| doi_str_mv | 10.1007/s11030-022-10432-6 |
| format | Article |
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O
catalyst in water. Initially, 2-mercapto-3-substituted phenethylquinazolin-4(3H)-one (5a-c) was prepared by using nano-CuFe
O
catalyst in water. Then, compounds (5a-c) were reacted with 1-bromo-3-chloropropane under nano-CuFe
O
catalyst in water solvent to give S-alkylated quinazolinone core intermediate (6a-c), which was subsequently reacted with 1-substituted-1H-tetrazole-5-thiol (2a-g) by employing the similar reaction conditions to afford the final target compounds. The regioselective formation of C-S bond was unambiguously confirmed by single-crystal X-ray diffraction. The anti-cancer activity of the derivatives on various cancer cell lines such as SIHA, MD-AMB-231 and HepG2 was evaluated. Remarkably, compounds, 7f, 8f, 9a, 9d and 9f, showed potent activity in MD-AMB-231 cancer cell line (IC
: 9.13-10.3 µM), while the same derivatives showed significant potent activity in SiHa and HepG2 cancer cell lines (IC
: 17.46-27.0 µM). Most significantly, compound 7o (IC
: 8.15 µM) showed potent activity, compared to the drug etoposide (IC
: 18.11 µM) against MD-AMB-231 cell line. Flow cytometry analysis revealed that compounds 7f, 8f, 9a, 9d and 9f arrested the cell growth in the G1 phase in MD-AMB-231 cell line.</description><identifier>EISSN: 1573-501X</identifier><identifier>DOI: 10.1007/s11030-022-10432-6</identifier><identifier>PMID: 35503155</identifier><language>eng</language><publisher>Netherlands</publisher><subject>Antineoplastic Agents - chemistry ; Catalysis ; Cell Proliferation ; Drug Screening Assays, Antitumor ; Molecular Structure ; Quinazolinones - chemistry ; Quinazolinones - pharmacology ; Structure-Activity Relationship ; Tetrazoles - pharmacology</subject><ispartof>Molecular diversity, 2023-02, Vol.27 (1), p.425</ispartof><rights>2022. The Author(s), under exclusive licence to Springer Nature Switzerland AG.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><orcidid>0000-0003-1195-665X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/35503155$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kommula, Dileep</creatorcontrib><creatorcontrib>Chintakunta, Praveen Kumar</creatorcontrib><creatorcontrib>Garikapati, Koteswararao</creatorcontrib><creatorcontrib>Murty, M S R</creatorcontrib><title>Nano-CuFe 2 O 3 -catalyzed green synthesis of novel quinazolinone-tetrazole hybrids as anti-cancer agents</title><title>Molecular diversity</title><addtitle>Mol Divers</addtitle><description>A novel green protocol has been developed for the synthesis of quinazolinone-tetrazole conjugates (7a-g, 8a-g and 9a-g) using recyclable nano-CuFe
O
catalyst in water. Initially, 2-mercapto-3-substituted phenethylquinazolin-4(3H)-one (5a-c) was prepared by using nano-CuFe
O
catalyst in water. Then, compounds (5a-c) were reacted with 1-bromo-3-chloropropane under nano-CuFe
O
catalyst in water solvent to give S-alkylated quinazolinone core intermediate (6a-c), which was subsequently reacted with 1-substituted-1H-tetrazole-5-thiol (2a-g) by employing the similar reaction conditions to afford the final target compounds. The regioselective formation of C-S bond was unambiguously confirmed by single-crystal X-ray diffraction. The anti-cancer activity of the derivatives on various cancer cell lines such as SIHA, MD-AMB-231 and HepG2 was evaluated. Remarkably, compounds, 7f, 8f, 9a, 9d and 9f, showed potent activity in MD-AMB-231 cancer cell line (IC
: 9.13-10.3 µM), while the same derivatives showed significant potent activity in SiHa and HepG2 cancer cell lines (IC
: 17.46-27.0 µM). Most significantly, compound 7o (IC
: 8.15 µM) showed potent activity, compared to the drug etoposide (IC
: 18.11 µM) against MD-AMB-231 cell line. Flow cytometry analysis revealed that compounds 7f, 8f, 9a, 9d and 9f arrested the cell growth in the G1 phase in MD-AMB-231 cell line.</description><subject>Antineoplastic Agents - chemistry</subject><subject>Catalysis</subject><subject>Cell Proliferation</subject><subject>Drug Screening Assays, Antitumor</subject><subject>Molecular Structure</subject><subject>Quinazolinones - chemistry</subject><subject>Quinazolinones - pharmacology</subject><subject>Structure-Activity Relationship</subject><subject>Tetrazoles - pharmacology</subject><issn>1573-501X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFjk1qAkEQhZtAiObnAlmEukAnVdPpeABRXMVNFu6kdUrtMFabrh5hPL0T0LXw4OPBx-MZ80r4ToijDyVChxaryhJ-usp-3Zkh-ZGzHmkxMI-qv4i9Su7BDJz36Mj7oYnfQZIdt1OGCubgwK5DCU134hq2mVlAOyk71qiQNiDpyA38tVHCKTVRkrAtXPJ_Y9h1qxxrhdBHSuynZM0Zwpal6LO534RG-eXCJ_M2nfyMZ_bQrvZcLw857kPultdv7qZwBjgRSmU</recordid><startdate>202302</startdate><enddate>202302</enddate><creator>Kommula, Dileep</creator><creator>Chintakunta, Praveen Kumar</creator><creator>Garikapati, Koteswararao</creator><creator>Murty, M S R</creator><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><orcidid>https://orcid.org/0000-0003-1195-665X</orcidid></search><sort><creationdate>202302</creationdate><title>Nano-CuFe 2 O 3 -catalyzed green synthesis of novel quinazolinone-tetrazole hybrids as anti-cancer agents</title><author>Kommula, Dileep ; Chintakunta, Praveen Kumar ; Garikapati, Koteswararao ; Murty, M S R</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-pubmed_primary_355031553</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Antineoplastic Agents - chemistry</topic><topic>Catalysis</topic><topic>Cell Proliferation</topic><topic>Drug Screening Assays, Antitumor</topic><topic>Molecular Structure</topic><topic>Quinazolinones - chemistry</topic><topic>Quinazolinones - pharmacology</topic><topic>Structure-Activity Relationship</topic><topic>Tetrazoles - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kommula, Dileep</creatorcontrib><creatorcontrib>Chintakunta, Praveen Kumar</creatorcontrib><creatorcontrib>Garikapati, Koteswararao</creatorcontrib><creatorcontrib>Murty, M S R</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><jtitle>Molecular diversity</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kommula, Dileep</au><au>Chintakunta, Praveen Kumar</au><au>Garikapati, Koteswararao</au><au>Murty, M S R</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Nano-CuFe 2 O 3 -catalyzed green synthesis of novel quinazolinone-tetrazole hybrids as anti-cancer agents</atitle><jtitle>Molecular diversity</jtitle><addtitle>Mol Divers</addtitle><date>2023-02</date><risdate>2023</risdate><volume>27</volume><issue>1</issue><spage>425</spage><pages>425-</pages><eissn>1573-501X</eissn><abstract>A novel green protocol has been developed for the synthesis of quinazolinone-tetrazole conjugates (7a-g, 8a-g and 9a-g) using recyclable nano-CuFe
O
catalyst in water. Initially, 2-mercapto-3-substituted phenethylquinazolin-4(3H)-one (5a-c) was prepared by using nano-CuFe
O
catalyst in water. Then, compounds (5a-c) were reacted with 1-bromo-3-chloropropane under nano-CuFe
O
catalyst in water solvent to give S-alkylated quinazolinone core intermediate (6a-c), which was subsequently reacted with 1-substituted-1H-tetrazole-5-thiol (2a-g) by employing the similar reaction conditions to afford the final target compounds. The regioselective formation of C-S bond was unambiguously confirmed by single-crystal X-ray diffraction. The anti-cancer activity of the derivatives on various cancer cell lines such as SIHA, MD-AMB-231 and HepG2 was evaluated. Remarkably, compounds, 7f, 8f, 9a, 9d and 9f, showed potent activity in MD-AMB-231 cancer cell line (IC
: 9.13-10.3 µM), while the same derivatives showed significant potent activity in SiHa and HepG2 cancer cell lines (IC
: 17.46-27.0 µM). Most significantly, compound 7o (IC
: 8.15 µM) showed potent activity, compared to the drug etoposide (IC
: 18.11 µM) against MD-AMB-231 cell line. Flow cytometry analysis revealed that compounds 7f, 8f, 9a, 9d and 9f arrested the cell growth in the G1 phase in MD-AMB-231 cell line.</abstract><cop>Netherlands</cop><pmid>35503155</pmid><doi>10.1007/s11030-022-10432-6</doi><orcidid>https://orcid.org/0000-0003-1195-665X</orcidid></addata></record> |
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| subjects | Antineoplastic Agents - chemistry Catalysis Cell Proliferation Drug Screening Assays, Antitumor Molecular Structure Quinazolinones - chemistry Quinazolinones - pharmacology Structure-Activity Relationship Tetrazoles - pharmacology |
| title | Nano-CuFe 2 O 3 -catalyzed green synthesis of novel quinazolinone-tetrazole hybrids as anti-cancer agents |
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