Synthesis and Anticancer Activities of Amide-Bridged Coumarin–Quinazolinone Hybrid Compounds
Some novel 3-aminoquinazolin-4( 3H )-one derivatives were synthesized by the reaction of 2-aminobenzhydrazide and corresponding iminoester hydrochlorides and then reacted with coumarin-3-carbonyl chloride to obtain novel coumarin–quinazolinone hybrids. The synthesized hybrid compounds were screened...
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| Veröffentlicht in: | Russian journal of organic chemistry 2024-05, Vol.60 (5), p.918-926 |
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| creator | Çalişkan, Nedime Menteşe, Emre Yilmaz, Fatih Ilhan, Muhammed Süleyman |
| description | Some novel 3-aminoquinazolin-4(
3H
)-one derivatives were synthesized by the reaction of 2-aminobenzhydrazide and corresponding iminoester hydrochlorides and then reacted with coumarin-3-carbonyl chloride to obtain novel coumarin–quinazolinone hybrids. The synthesized hybrid compounds were screened for their anticancer activity against various human cancer and normal cell lines.
N
-{2-[(4-Bromo- and
N
-{2-[(3-bromo-phenyl)methyl]-4-oxoquinazolin-3(4
H
)-yl}-2-oxo-2
H
-1-benzopyran-3-carboxamides exhibited the highest cytotoxic effect on the PC-3 prostate cancer cell line: IC
50
35.3 ± 0.6 and 36.8 ± 0.8 µg/L, respectively.
N
-{2-[(4-Fluoro-,
N
-{2-[(4-bromo-, and
N
-{2-[(3,4-dichloro-phenyl)methyl]-4-oxoquinazolin-3(4
H
)-yl}-2-oxo-2
H
-1-benzopyran-3-carboxamides showed the highest activity against the MCF-7 breast cancer cell line: IC
50
48.5 ± 0.4, 44.8 ± 0.4 and 46.1 ± 0.5 µg/L, respectively. |
| doi_str_mv | 10.1134/S1070428024050142 |
| format | Article |
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3H
)-one derivatives were synthesized by the reaction of 2-aminobenzhydrazide and corresponding iminoester hydrochlorides and then reacted with coumarin-3-carbonyl chloride to obtain novel coumarin–quinazolinone hybrids. The synthesized hybrid compounds were screened for their anticancer activity against various human cancer and normal cell lines.
N
-{2-[(4-Bromo- and
N
-{2-[(3-bromo-phenyl)methyl]-4-oxoquinazolin-3(4
H
)-yl}-2-oxo-2
H
-1-benzopyran-3-carboxamides exhibited the highest cytotoxic effect on the PC-3 prostate cancer cell line: IC
50
35.3 ± 0.6 and 36.8 ± 0.8 µg/L, respectively.
N
-{2-[(4-Fluoro-,
N
-{2-[(4-bromo-, and
N
-{2-[(3,4-dichloro-phenyl)methyl]-4-oxoquinazolin-3(4
H
)-yl}-2-oxo-2
H
-1-benzopyran-3-carboxamides showed the highest activity against the MCF-7 breast cancer cell line: IC
50
48.5 ± 0.4, 44.8 ± 0.4 and 46.1 ± 0.5 µg/L, respectively.</description><identifier>ISSN: 1070-4280</identifier><identifier>EISSN: 1608-3393</identifier><identifier>DOI: 10.1134/S1070428024050142</identifier><language>eng</language><publisher>Moscow: Pleiades Publishing</publisher><subject>Anticancer properties ; Carbonyls ; Chemical synthesis ; Chemistry ; Chemistry and Materials Science ; Coumarin ; Hydrochlorides ; Organic Chemistry ; Phosgene ; Quinazolinones</subject><ispartof>Russian journal of organic chemistry, 2024-05, Vol.60 (5), p.918-926</ispartof><rights>Pleiades Publishing, Ltd. 2024</rights><rights>Pleiades Publishing, Ltd. 2024.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c268t-dae0dcfc80bc7110c2cd49cc59e1409727b7f8ae52191279ea18a5f8845a0e823</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1134/S1070428024050142$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1134/S1070428024050142$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,27901,27902,41464,42533,51294</link.rule.ids></links><search><creatorcontrib>Çalişkan, Nedime</creatorcontrib><creatorcontrib>Menteşe, Emre</creatorcontrib><creatorcontrib>Yilmaz, Fatih</creatorcontrib><creatorcontrib>Ilhan, Muhammed Süleyman</creatorcontrib><title>Synthesis and Anticancer Activities of Amide-Bridged Coumarin–Quinazolinone Hybrid Compounds</title><title>Russian journal of organic chemistry</title><addtitle>Russ J Org Chem</addtitle><description>Some novel 3-aminoquinazolin-4(
3H
)-one derivatives were synthesized by the reaction of 2-aminobenzhydrazide and corresponding iminoester hydrochlorides and then reacted with coumarin-3-carbonyl chloride to obtain novel coumarin–quinazolinone hybrids. The synthesized hybrid compounds were screened for their anticancer activity against various human cancer and normal cell lines.
N
-{2-[(4-Bromo- and
N
-{2-[(3-bromo-phenyl)methyl]-4-oxoquinazolin-3(4
H
)-yl}-2-oxo-2
H
-1-benzopyran-3-carboxamides exhibited the highest cytotoxic effect on the PC-3 prostate cancer cell line: IC
50
35.3 ± 0.6 and 36.8 ± 0.8 µg/L, respectively.
N
-{2-[(4-Fluoro-,
N
-{2-[(4-bromo-, and
N
-{2-[(3,4-dichloro-phenyl)methyl]-4-oxoquinazolin-3(4
H
)-yl}-2-oxo-2
H
-1-benzopyran-3-carboxamides showed the highest activity against the MCF-7 breast cancer cell line: IC
50
48.5 ± 0.4, 44.8 ± 0.4 and 46.1 ± 0.5 µg/L, respectively.</description><subject>Anticancer properties</subject><subject>Carbonyls</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Coumarin</subject><subject>Hydrochlorides</subject><subject>Organic Chemistry</subject><subject>Phosgene</subject><subject>Quinazolinones</subject><issn>1070-4280</issn><issn>1608-3393</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNp1kMFKAzEQhoMoWKsP4G3B8-okm22yx7WoFQoi6tUlTWZrSpvUZFeoJ9_BN_RJTKngQTzNwP_9_zA_IacUzikt-MUDBQGcSWAcSqCc7ZEBHYHMi6Iq9tOe5HyrH5KjGBcAwCkvBuT5YeO6F4w2ZsqZrHad1cppDFmtO_tmO4sx821Wr6zB_DJYM0eTjX2_UsG6r4_P-9469e6X1nmH2WQzS0jSV2vfOxOPyUGrlhFPfuaQPF1fPY4n-fTu5nZcT3PNRrLLjUIwutUSZlpQCpppwyutywoph0owMROtVFgyWlEmKlRUqrKVkpcKULJiSM52uevgX3uMXbPwfXDpZFOAHG1LqESi6I7SwccYsG3WwaZHNg2FZltj86fG5GE7T0ysm2P4Tf7f9A14yXVw</recordid><startdate>20240501</startdate><enddate>20240501</enddate><creator>Çalişkan, Nedime</creator><creator>Menteşe, Emre</creator><creator>Yilmaz, Fatih</creator><creator>Ilhan, Muhammed Süleyman</creator><general>Pleiades Publishing</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20240501</creationdate><title>Synthesis and Anticancer Activities of Amide-Bridged Coumarin–Quinazolinone Hybrid Compounds</title><author>Çalişkan, Nedime ; Menteşe, Emre ; Yilmaz, Fatih ; Ilhan, Muhammed Süleyman</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c268t-dae0dcfc80bc7110c2cd49cc59e1409727b7f8ae52191279ea18a5f8845a0e823</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Anticancer properties</topic><topic>Carbonyls</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Coumarin</topic><topic>Hydrochlorides</topic><topic>Organic Chemistry</topic><topic>Phosgene</topic><topic>Quinazolinones</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Çalişkan, Nedime</creatorcontrib><creatorcontrib>Menteşe, Emre</creatorcontrib><creatorcontrib>Yilmaz, Fatih</creatorcontrib><creatorcontrib>Ilhan, Muhammed Süleyman</creatorcontrib><collection>CrossRef</collection><jtitle>Russian journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Çalişkan, Nedime</au><au>Menteşe, Emre</au><au>Yilmaz, Fatih</au><au>Ilhan, Muhammed Süleyman</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Anticancer Activities of Amide-Bridged Coumarin–Quinazolinone Hybrid Compounds</atitle><jtitle>Russian journal of organic chemistry</jtitle><stitle>Russ J Org Chem</stitle><date>2024-05-01</date><risdate>2024</risdate><volume>60</volume><issue>5</issue><spage>918</spage><epage>926</epage><pages>918-926</pages><issn>1070-4280</issn><eissn>1608-3393</eissn><abstract>Some novel 3-aminoquinazolin-4(
3H
)-one derivatives were synthesized by the reaction of 2-aminobenzhydrazide and corresponding iminoester hydrochlorides and then reacted with coumarin-3-carbonyl chloride to obtain novel coumarin–quinazolinone hybrids. The synthesized hybrid compounds were screened for their anticancer activity against various human cancer and normal cell lines.
N
-{2-[(4-Bromo- and
N
-{2-[(3-bromo-phenyl)methyl]-4-oxoquinazolin-3(4
H
)-yl}-2-oxo-2
H
-1-benzopyran-3-carboxamides exhibited the highest cytotoxic effect on the PC-3 prostate cancer cell line: IC
50
35.3 ± 0.6 and 36.8 ± 0.8 µg/L, respectively.
N
-{2-[(4-Fluoro-,
N
-{2-[(4-bromo-, and
N
-{2-[(3,4-dichloro-phenyl)methyl]-4-oxoquinazolin-3(4
H
)-yl}-2-oxo-2
H
-1-benzopyran-3-carboxamides showed the highest activity against the MCF-7 breast cancer cell line: IC
50
48.5 ± 0.4, 44.8 ± 0.4 and 46.1 ± 0.5 µg/L, respectively.</abstract><cop>Moscow</cop><pub>Pleiades Publishing</pub><doi>10.1134/S1070428024050142</doi><tpages>9</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1070-4280 |
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| issn | 1070-4280 1608-3393 |
| language | eng |
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| source | Springer Online Journals |
| subjects | Anticancer properties Carbonyls Chemical synthesis Chemistry Chemistry and Materials Science Coumarin Hydrochlorides Organic Chemistry Phosgene Quinazolinones |
| title | Synthesis and Anticancer Activities of Amide-Bridged Coumarin–Quinazolinone Hybrid Compounds |
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