Synthesis, in-vitro cytotoxicity of 4H-benzo[h]chromene derivatives and structure—activity relationships of 4-aryl group and 3-, 7-positions
A series of 2-amino-4 H -benzo[ h ]chromene and 2,7-diamino-4 H -benzo[ h ]chromene derivatives were prepared as potential cytotoxic agents. The structures of the synthesised compounds were established on the basis of spectral data. The in-vitro cytotoxic activity of the synthesised compounds agains...
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| Veröffentlicht in: | Chemical papers 2016-09, Vol.70 (9), p.1279-1292 |
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| creator | El-Agrody, Ahmed M. El-Mawgoud, Heba K. Abd Fouda, Ahmed M. Khattab, Essam S. A. E. H. |
| description | A series of 2-amino-4
H
-benzo[
h
]chromene and 2,7-diamino-4
H
-benzo[
h
]chromene derivatives were prepared as potential cytotoxic agents. The structures of the synthesised compounds were established on the basis of spectral data. The in-vitro cytotoxic activity of the synthesised compounds against the cell lines MCF-7, HCT-116 and HepG-2 was investigated in comparison with vinblastine and colchicine, using an MTT colorimetric assay. The structure-activity relationship of 4
H
-benzo[
h
]chromenes with modification at the 3-, 4- and 7-positions was explored. The results of the anti-tumour evaluation revealed that compounds
VIIIc, VIId, VIIb, VIIe, VIIIg
and
VIIIc, VIId, VIIb, VIIe, VIIIg, VIIc, VIIIe, Vf, IIIa
inhibited the growth of MCF-7 in comparison with vinblastine and colchicine, while
VIIb, VIId, VIIe, IIIa, VIIa, VIIIc, VIIc, IIId, IIIg, IIIf, IIIb, IIIh, VIIIb, VIIIa, VIIIe, IIIc, Vg, IIIe, VIIIg, Vf, IIIf
inhibited the growth of HCT-116 in comparison with colchicine. In addition, compounds
VIIe, IIIg, IIIa, VIIc
and
VIIe, IIIg, IIIa, VIIc, VIIb, VIIa, VIIIf, VIIIe
inhibited the growth of HepG-2 in comparison with vinblastine and colchicine, respectively. |
| doi_str_mv | 10.1515/chempap-2016-0049 |
| format | Article |
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H
-benzo[
h
]chromene and 2,7-diamino-4
H
-benzo[
h
]chromene derivatives were prepared as potential cytotoxic agents. The structures of the synthesised compounds were established on the basis of spectral data. The in-vitro cytotoxic activity of the synthesised compounds against the cell lines MCF-7, HCT-116 and HepG-2 was investigated in comparison with vinblastine and colchicine, using an MTT colorimetric assay. The structure-activity relationship of 4
H
-benzo[
h
]chromenes with modification at the 3-, 4- and 7-positions was explored. The results of the anti-tumour evaluation revealed that compounds
VIIIc, VIId, VIIb, VIIe, VIIIg
and
VIIIc, VIId, VIIb, VIIe, VIIIg, VIIc, VIIIe, Vf, IIIa
inhibited the growth of MCF-7 in comparison with vinblastine and colchicine, while
VIIb, VIId, VIIe, IIIa, VIIa, VIIIc, VIIc, IIId, IIIg, IIIf, IIIb, IIIh, VIIIb, VIIIa, VIIIe, IIIc, Vg, IIIe, VIIIg, Vf, IIIf
inhibited the growth of HCT-116 in comparison with colchicine. In addition, compounds
VIIe, IIIg, IIIa, VIIc
and
VIIe, IIIg, IIIa, VIIc, VIIb, VIIa, VIIIf, VIIIe
inhibited the growth of HepG-2 in comparison with vinblastine and colchicine, respectively.</description><identifier>ISSN: 0366-6352</identifier><identifier>EISSN: 1336-9075</identifier><identifier>DOI: 10.1515/chempap-2016-0049</identifier><language>eng</language><publisher>Cham: Springer International Publishing</publisher><subject>1-naphthol ; 5-amino-1-naphthol ; Aromatic compounds ; benzo ; Biochemistry ; Biotechnology ; Chemistry ; Chemistry and Materials Science ; Chemistry/Food Science ; chromenes ; Colchicine ; Colorimetry ; Cytotoxicity ; Derivatives ; Industrial Chemistry/Chemical Engineering ; Materials Science ; Medicinal Chemistry ; Original Paper ; SAR ; Toxicity</subject><ispartof>Chemical papers, 2016-09, Vol.70 (9), p.1279-1292</ispartof><rights>Institute of Chemistry, Slovak Academy of Sciences 2016</rights><rights>Copyright Walter de Gruyter GmbH 2016</rights><rights>Institute of Chemistry, Slovak Academy of Sciences 2016.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c539t-32847a30ca5f87985218a36b76b3adf57c992cdf8aad0a19b3b6423e873d8cfb3</citedby><cites>FETCH-LOGICAL-c539t-32847a30ca5f87985218a36b76b3adf57c992cdf8aad0a19b3b6423e873d8cfb3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1515/chempap-2016-0049$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1515/chempap-2016-0049$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27924,27925,41488,42557,51319</link.rule.ids></links><search><creatorcontrib>El-Agrody, Ahmed M.</creatorcontrib><creatorcontrib>El-Mawgoud, Heba K. Abd</creatorcontrib><creatorcontrib>Fouda, Ahmed M.</creatorcontrib><creatorcontrib>Khattab, Essam S. A. E. H.</creatorcontrib><title>Synthesis, in-vitro cytotoxicity of 4H-benzo[h]chromene derivatives and structure—activity relationships of 4-aryl group and 3-, 7-positions</title><title>Chemical papers</title><addtitle>Chem. Pap</addtitle><description>A series of 2-amino-4
H
-benzo[
h
]chromene and 2,7-diamino-4
H
-benzo[
h
]chromene derivatives were prepared as potential cytotoxic agents. The structures of the synthesised compounds were established on the basis of spectral data. The in-vitro cytotoxic activity of the synthesised compounds against the cell lines MCF-7, HCT-116 and HepG-2 was investigated in comparison with vinblastine and colchicine, using an MTT colorimetric assay. The structure-activity relationship of 4
H
-benzo[
h
]chromenes with modification at the 3-, 4- and 7-positions was explored. The results of the anti-tumour evaluation revealed that compounds
VIIIc, VIId, VIIb, VIIe, VIIIg
and
VIIIc, VIId, VIIb, VIIe, VIIIg, VIIc, VIIIe, Vf, IIIa
inhibited the growth of MCF-7 in comparison with vinblastine and colchicine, while
VIIb, VIId, VIIe, IIIa, VIIa, VIIIc, VIIc, IIId, IIIg, IIIf, IIIb, IIIh, VIIIb, VIIIa, VIIIe, IIIc, Vg, IIIe, VIIIg, Vf, IIIf
inhibited the growth of HCT-116 in comparison with colchicine. In addition, compounds
VIIe, IIIg, IIIa, VIIc
and
VIIe, IIIg, IIIa, VIIc, VIIb, VIIa, VIIIf, VIIIe
inhibited the growth of HepG-2 in comparison with vinblastine and colchicine, respectively.</description><subject>1-naphthol</subject><subject>5-amino-1-naphthol</subject><subject>Aromatic compounds</subject><subject>benzo</subject><subject>Biochemistry</subject><subject>Biotechnology</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Chemistry/Food Science</subject><subject>chromenes</subject><subject>Colchicine</subject><subject>Colorimetry</subject><subject>Cytotoxicity</subject><subject>Derivatives</subject><subject>Industrial Chemistry/Chemical Engineering</subject><subject>Materials Science</subject><subject>Medicinal Chemistry</subject><subject>Original Paper</subject><subject>SAR</subject><subject>Toxicity</subject><issn>0366-6352</issn><issn>1336-9075</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>AFKRA</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><recordid>eNqNkcFu1DAURa2qSExLP4CdpW5rsP3iON6BqkKRKrEAVqiKHMeZuJqJg-0MhFW_oCu-kC_BmemCDRUrW9Y59-n5IvSS0VdMMPHa9HY76pFwykpCaaGO0IoBlERRKY7RikJZkhIEf45OYrzLREEFXaGHT_OQehtdvMBuIDuXgsdmTj75H864NGPf4eKaNHb46b_2t6YPfmsHi1sb3E4nt7MR66HFMYXJpCnY3_e_tMnvixvsJiN-iL0b4z6J6DBv8Dr4adxrQC6wJKOPbs-9QM86vYn27PE8RV_eXX2-vCY3H99_uHx7Q4wAlQjwqpAaqNGiq6SqBGeVhrKRZQO67YQ0SnHTdpXWLdVMNdCUBQdbSWgr0zVwis4PuWPw3yYbU33npzDkkTUvKLDlT8VTFKuY4pJJKDLFDpQJPsZgu3oMbpv3rBmtl6D6sZx6KadeysnOm4PzXW-SDa1dh2nOl78G_MuVVDEulwh-iIh53LD-Lxf-ANuJrRA</recordid><startdate>20160901</startdate><enddate>20160901</enddate><creator>El-Agrody, Ahmed M.</creator><creator>El-Mawgoud, Heba K. Abd</creator><creator>Fouda, Ahmed M.</creator><creator>Khattab, Essam S. A. E. H.</creator><general>Springer International Publishing</general><general>De Gruyter</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>8FE</scope><scope>8FG</scope><scope>ABJCF</scope><scope>AFKRA</scope><scope>BENPR</scope><scope>BGLVJ</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>HCIFZ</scope><scope>JG9</scope><scope>L6V</scope><scope>L7M</scope><scope>M7S</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>PTHSS</scope></search><sort><creationdate>20160901</creationdate><title>Synthesis, in-vitro cytotoxicity of 4H-benzo[h]chromene derivatives and structure—activity relationships of 4-aryl group and 3-, 7-positions</title><author>El-Agrody, Ahmed M. ; El-Mawgoud, Heba K. Abd ; Fouda, Ahmed M. ; Khattab, Essam S. A. E. H.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c539t-32847a30ca5f87985218a36b76b3adf57c992cdf8aad0a19b3b6423e873d8cfb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>1-naphthol</topic><topic>5-amino-1-naphthol</topic><topic>Aromatic compounds</topic><topic>benzo</topic><topic>Biochemistry</topic><topic>Biotechnology</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Chemistry/Food Science</topic><topic>chromenes</topic><topic>Colchicine</topic><topic>Colorimetry</topic><topic>Cytotoxicity</topic><topic>Derivatives</topic><topic>Industrial Chemistry/Chemical Engineering</topic><topic>Materials Science</topic><topic>Medicinal Chemistry</topic><topic>Original Paper</topic><topic>SAR</topic><topic>Toxicity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>El-Agrody, Ahmed M.</creatorcontrib><creatorcontrib>El-Mawgoud, Heba K. Abd</creatorcontrib><creatorcontrib>Fouda, Ahmed M.</creatorcontrib><creatorcontrib>Khattab, Essam S. A. E. H.</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Technology Collection</collection><collection>Materials Science & Engineering Collection</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central</collection><collection>Technology Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central Korea</collection><collection>SciTech Premium Collection</collection><collection>Materials Research Database</collection><collection>ProQuest Engineering Collection</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>Engineering Database</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>Engineering Collection</collection><jtitle>Chemical papers</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>El-Agrody, Ahmed M.</au><au>El-Mawgoud, Heba K. Abd</au><au>Fouda, Ahmed M.</au><au>Khattab, Essam S. A. E. H.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, in-vitro cytotoxicity of 4H-benzo[h]chromene derivatives and structure—activity relationships of 4-aryl group and 3-, 7-positions</atitle><jtitle>Chemical papers</jtitle><stitle>Chem. Pap</stitle><date>2016-09-01</date><risdate>2016</risdate><volume>70</volume><issue>9</issue><spage>1279</spage><epage>1292</epage><pages>1279-1292</pages><issn>0366-6352</issn><eissn>1336-9075</eissn><abstract>A series of 2-amino-4
H
-benzo[
h
]chromene and 2,7-diamino-4
H
-benzo[
h
]chromene derivatives were prepared as potential cytotoxic agents. The structures of the synthesised compounds were established on the basis of spectral data. The in-vitro cytotoxic activity of the synthesised compounds against the cell lines MCF-7, HCT-116 and HepG-2 was investigated in comparison with vinblastine and colchicine, using an MTT colorimetric assay. The structure-activity relationship of 4
H
-benzo[
h
]chromenes with modification at the 3-, 4- and 7-positions was explored. The results of the anti-tumour evaluation revealed that compounds
VIIIc, VIId, VIIb, VIIe, VIIIg
and
VIIIc, VIId, VIIb, VIIe, VIIIg, VIIc, VIIIe, Vf, IIIa
inhibited the growth of MCF-7 in comparison with vinblastine and colchicine, while
VIIb, VIId, VIIe, IIIa, VIIa, VIIIc, VIIc, IIId, IIIg, IIIf, IIIb, IIIh, VIIIb, VIIIa, VIIIe, IIIc, Vg, IIIe, VIIIg, Vf, IIIf
inhibited the growth of HCT-116 in comparison with colchicine. In addition, compounds
VIIe, IIIg, IIIa, VIIc
and
VIIe, IIIg, IIIa, VIIc, VIIb, VIIa, VIIIf, VIIIe
inhibited the growth of HepG-2 in comparison with vinblastine and colchicine, respectively.</abstract><cop>Cham</cop><pub>Springer International Publishing</pub><doi>10.1515/chempap-2016-0049</doi><tpages>14</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0366-6352 |
| ispartof | Chemical papers, 2016-09, Vol.70 (9), p.1279-1292 |
| issn | 0366-6352 1336-9075 |
| language | eng |
| recordid | cdi_proquest_journals_2403115155 |
| source | SpringerLink Journals - AutoHoldings |
| subjects | 1-naphthol 5-amino-1-naphthol Aromatic compounds benzo Biochemistry Biotechnology Chemistry Chemistry and Materials Science Chemistry/Food Science chromenes Colchicine Colorimetry Cytotoxicity Derivatives Industrial Chemistry/Chemical Engineering Materials Science Medicinal Chemistry Original Paper SAR Toxicity |
| title | Synthesis, in-vitro cytotoxicity of 4H-benzo[h]chromene derivatives and structure—activity relationships of 4-aryl group and 3-, 7-positions |
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