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Recyclization of morpholinochromonylidene-thiazolidinone using nucleophiles: facile synthesis, cytotoxic evaluation, apoptosis, cell cycle and molecular docking studies of a novel series of azole, azine, azepine and pyran derivatives
A convenient synthetic approach for construction of a novel series of substituted azoles, azines, azepines and pyrans clubbed with a morpholinothiazolidinone hybrid was achieved. The methodology depended on ring-opening and ring-closure (RORC) of chromone ring in 2-(morpholinoimino)-5-[(4-oxo-4 H -c...
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| Published in: | RSC advances 2023-06, Vol.13 (27), p.18658-18675 |
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| Main Authors: | , , , , , |
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| cited_by | cdi_FETCH-LOGICAL-c429t-cf4596384b963c1b3033258009c3e7230f432471c06d06d448a20a9300b9baa73 |
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| cites | cdi_FETCH-LOGICAL-c429t-cf4596384b963c1b3033258009c3e7230f432471c06d06d448a20a9300b9baa73 |
| container_end_page | 18675 |
| container_issue | 27 |
| container_start_page | 18658 |
| container_title | RSC advances |
| container_volume | 13 |
| creator | Ali, Tarik E Assiri, Mohammed A Alqahtani, Maha N Shati, Ali. A Alfaifi, Mohammad. Y Elbehairi, Serag. E. I |
| description | A convenient synthetic approach for construction of a novel series of substituted azoles, azines, azepines and pyrans clubbed with a morpholinothiazolidinone hybrid was achieved. The methodology depended on ring-opening and ring-closure (RORC) of chromone ring in 2-(morpholinoimino)-5-[(4-oxo-4
H
-chromen-3-yl)methylene]-3-phenylthiazolidin-4-one (
3
) through its reaction with a series of nitrogen and carbon nucleophiles under mild reaction conditions. The cytotoxic effects of all products were evaluated against three cancerous cell lines (MCF-7, HepG-2 and SKOV-3) by the standard SRB method. Fortunately, the products
7
,
11
,
12
,
15
,
19
,
22
,
26
and
28
were found to be the most active against all cancer cell lines, comparable to doxorubicin. Apoptosis was determined using flow cytometry along with cell cycle analysis and supported by molecular docking. The products
7
,
11
,
12
,
15
,
19
,
22
,
26
and
28
induced a significant early-and late-apoptotic effect against all tumor cells. In addition, these products preferred to arrest all cancer cells in the G1 and G2 phases. Finally, molecular docking was attempted to investigate the binding mode of products
12
and
22
with p53-MDM2 protein receptor.
Construction of a novel series of substituted azoles, azines, azepines and pyrans clubbed with a morpholinothiazolidinone hybrid with anticancer properties, was achieved. |
| doi_str_mv | 10.1039/d3ra02777e |
| format | article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1039_D3RA02777E</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2828773917</sourcerecordid><originalsourceid>FETCH-LOGICAL-c429t-cf4596384b963c1b3033258009c3e7230f432471c06d06d448a20a9300b9baa73</originalsourceid><addsrcrecordid>eNpdkl1r1jAUx4sobszdeK8EvJGxat6evngjY84XGAhDr0uanq6ZadIlabHPN963MO2zPU5DyDnk_Piff8JJkpcEvyOYle8b5gSmeZ7Dk-SQYp6lFGfl00f5QXLs_Q2OK9sQmpHnyQHLGc9Kzg6TuyuQs9RqK4KyBtkW9dYNndXKWNk521sza9WAgTR0SmxjoYklA2j0ylwjM0oNduiUBv8BtULGBPnZhA688qdIzsEG-1tJBJPQ49rlFInBDsHuANAaLRYACdPE7hrkqIVDjZW_lg4-jI0Cv1gTyNgJNPLgHm6iIYh6W2XWAENMVqFhdsKgJpJTbDqBf5E8a4X2cHwfj5Kfny9-nH9NL79_-XZ-dplKTsuQypZvyowVvI6nJDXDjNFNgXEpGeSU4ZYzynMicdbEzXkhKBYlw7guayFydpR83OkOY91DI8EEJ3Q1ONULN1dWqOrfilFddW2nimBaEIwXhbf3Cs7ejuBD1Su__JMwYEdf0YIWec5KsqBv_kNv7OhMfN9KZbzguIjUyY6SznrvoN27Ibhapqj6xK7O1im6iPDrx_736MPMRODVDnBe7qt_x5D9AZ-W0xY</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2828648408</pqid></control><display><type>article</type><title>Recyclization of morpholinochromonylidene-thiazolidinone using nucleophiles: facile synthesis, cytotoxic evaluation, apoptosis, cell cycle and molecular docking studies of a novel series of azole, azine, azepine and pyran derivatives</title><source>Open Access: PubMed Central</source><creator>Ali, Tarik E ; Assiri, Mohammed A ; Alqahtani, Maha N ; Shati, Ali. A ; Alfaifi, Mohammad. Y ; Elbehairi, Serag. E. I</creator><creatorcontrib>Ali, Tarik E ; Assiri, Mohammed A ; Alqahtani, Maha N ; Shati, Ali. A ; Alfaifi, Mohammad. Y ; Elbehairi, Serag. E. I</creatorcontrib><description>A convenient synthetic approach for construction of a novel series of substituted azoles, azines, azepines and pyrans clubbed with a morpholinothiazolidinone hybrid was achieved. The methodology depended on ring-opening and ring-closure (RORC) of chromone ring in 2-(morpholinoimino)-5-[(4-oxo-4
H
-chromen-3-yl)methylene]-3-phenylthiazolidin-4-one (
3
) through its reaction with a series of nitrogen and carbon nucleophiles under mild reaction conditions. The cytotoxic effects of all products were evaluated against three cancerous cell lines (MCF-7, HepG-2 and SKOV-3) by the standard SRB method. Fortunately, the products
7
,
11
,
12
,
15
,
19
,
22
,
26
and
28
were found to be the most active against all cancer cell lines, comparable to doxorubicin. Apoptosis was determined using flow cytometry along with cell cycle analysis and supported by molecular docking. The products
7
,
11
,
12
,
15
,
19
,
22
,
26
and
28
induced a significant early-and late-apoptotic effect against all tumor cells. In addition, these products preferred to arrest all cancer cells in the G1 and G2 phases. Finally, molecular docking was attempted to investigate the binding mode of products
12
and
22
with p53-MDM2 protein receptor.
Construction of a novel series of substituted azoles, azines, azepines and pyrans clubbed with a morpholinothiazolidinone hybrid with anticancer properties, was achieved.</description><identifier>ISSN: 2046-2069</identifier><identifier>EISSN: 2046-2069</identifier><identifier>DOI: 10.1039/d3ra02777e</identifier><identifier>PMID: 37346943</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Apoptosis ; Azines ; Cancer ; Cell cycle ; Chemistry ; Cytotoxicity ; Doxorubicin ; Flow cytometry ; Heterocyclic compounds ; Molecular docking ; Nucleophiles ; Ring opening</subject><ispartof>RSC advances, 2023-06, Vol.13 (27), p.18658-18675</ispartof><rights>This journal is © The Royal Society of Chemistry.</rights><rights>Copyright Royal Society of Chemistry 2023</rights><rights>This journal is © The Royal Society of Chemistry 2023 The Royal Society of Chemistry</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c429t-cf4596384b963c1b3033258009c3e7230f432471c06d06d448a20a9300b9baa73</citedby><cites>FETCH-LOGICAL-c429t-cf4596384b963c1b3033258009c3e7230f432471c06d06d448a20a9300b9baa73</cites><orcidid>0000-0002-7992-3478</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC10281007/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC10281007/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,27924,27925,53791,53793</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/37346943$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ali, Tarik E</creatorcontrib><creatorcontrib>Assiri, Mohammed A</creatorcontrib><creatorcontrib>Alqahtani, Maha N</creatorcontrib><creatorcontrib>Shati, Ali. A</creatorcontrib><creatorcontrib>Alfaifi, Mohammad. Y</creatorcontrib><creatorcontrib>Elbehairi, Serag. E. I</creatorcontrib><title>Recyclization of morpholinochromonylidene-thiazolidinone using nucleophiles: facile synthesis, cytotoxic evaluation, apoptosis, cell cycle and molecular docking studies of a novel series of azole, azine, azepine and pyran derivatives</title><title>RSC advances</title><addtitle>RSC Adv</addtitle><description>A convenient synthetic approach for construction of a novel series of substituted azoles, azines, azepines and pyrans clubbed with a morpholinothiazolidinone hybrid was achieved. The methodology depended on ring-opening and ring-closure (RORC) of chromone ring in 2-(morpholinoimino)-5-[(4-oxo-4
H
-chromen-3-yl)methylene]-3-phenylthiazolidin-4-one (
3
) through its reaction with a series of nitrogen and carbon nucleophiles under mild reaction conditions. The cytotoxic effects of all products were evaluated against three cancerous cell lines (MCF-7, HepG-2 and SKOV-3) by the standard SRB method. Fortunately, the products
7
,
11
,
12
,
15
,
19
,
22
,
26
and
28
were found to be the most active against all cancer cell lines, comparable to doxorubicin. Apoptosis was determined using flow cytometry along with cell cycle analysis and supported by molecular docking. The products
7
,
11
,
12
,
15
,
19
,
22
,
26
and
28
induced a significant early-and late-apoptotic effect against all tumor cells. In addition, these products preferred to arrest all cancer cells in the G1 and G2 phases. Finally, molecular docking was attempted to investigate the binding mode of products
12
and
22
with p53-MDM2 protein receptor.
Construction of a novel series of substituted azoles, azines, azepines and pyrans clubbed with a morpholinothiazolidinone hybrid with anticancer properties, was achieved.</description><subject>Apoptosis</subject><subject>Azines</subject><subject>Cancer</subject><subject>Cell cycle</subject><subject>Chemistry</subject><subject>Cytotoxicity</subject><subject>Doxorubicin</subject><subject>Flow cytometry</subject><subject>Heterocyclic compounds</subject><subject>Molecular docking</subject><subject>Nucleophiles</subject><subject>Ring opening</subject><issn>2046-2069</issn><issn>2046-2069</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNpdkl1r1jAUx4sobszdeK8EvJGxat6evngjY84XGAhDr0uanq6ZadIlabHPN963MO2zPU5DyDnk_Piff8JJkpcEvyOYle8b5gSmeZ7Dk-SQYp6lFGfl00f5QXLs_Q2OK9sQmpHnyQHLGc9Kzg6TuyuQs9RqK4KyBtkW9dYNndXKWNk521sza9WAgTR0SmxjoYklA2j0ylwjM0oNduiUBv8BtULGBPnZhA688qdIzsEG-1tJBJPQ49rlFInBDsHuANAaLRYACdPE7hrkqIVDjZW_lg4-jI0Cv1gTyNgJNPLgHm6iIYh6W2XWAENMVqFhdsKgJpJTbDqBf5E8a4X2cHwfj5Kfny9-nH9NL79_-XZ-dplKTsuQypZvyowVvI6nJDXDjNFNgXEpGeSU4ZYzynMicdbEzXkhKBYlw7guayFydpR83OkOY91DI8EEJ3Q1ONULN1dWqOrfilFddW2nimBaEIwXhbf3Cs7ejuBD1Su__JMwYEdf0YIWec5KsqBv_kNv7OhMfN9KZbzguIjUyY6SznrvoN27Ibhapqj6xK7O1im6iPDrx_736MPMRODVDnBe7qt_x5D9AZ-W0xY</recordid><startdate>20230615</startdate><enddate>20230615</enddate><creator>Ali, Tarik E</creator><creator>Assiri, Mohammed A</creator><creator>Alqahtani, Maha N</creator><creator>Shati, Ali. A</creator><creator>Alfaifi, Mohammad. Y</creator><creator>Elbehairi, Serag. E. I</creator><general>Royal Society of Chemistry</general><general>The Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-7992-3478</orcidid></search><sort><creationdate>20230615</creationdate><title>Recyclization of morpholinochromonylidene-thiazolidinone using nucleophiles: facile synthesis, cytotoxic evaluation, apoptosis, cell cycle and molecular docking studies of a novel series of azole, azine, azepine and pyran derivatives</title><author>Ali, Tarik E ; Assiri, Mohammed A ; Alqahtani, Maha N ; Shati, Ali. A ; Alfaifi, Mohammad. Y ; Elbehairi, Serag. E. I</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c429t-cf4596384b963c1b3033258009c3e7230f432471c06d06d448a20a9300b9baa73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Apoptosis</topic><topic>Azines</topic><topic>Cancer</topic><topic>Cell cycle</topic><topic>Chemistry</topic><topic>Cytotoxicity</topic><topic>Doxorubicin</topic><topic>Flow cytometry</topic><topic>Heterocyclic compounds</topic><topic>Molecular docking</topic><topic>Nucleophiles</topic><topic>Ring opening</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ali, Tarik E</creatorcontrib><creatorcontrib>Assiri, Mohammed A</creatorcontrib><creatorcontrib>Alqahtani, Maha N</creatorcontrib><creatorcontrib>Shati, Ali. A</creatorcontrib><creatorcontrib>Alfaifi, Mohammad. Y</creatorcontrib><creatorcontrib>Elbehairi, Serag. E. I</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>RSC advances</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ali, Tarik E</au><au>Assiri, Mohammed A</au><au>Alqahtani, Maha N</au><au>Shati, Ali. A</au><au>Alfaifi, Mohammad. Y</au><au>Elbehairi, Serag. E. I</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Recyclization of morpholinochromonylidene-thiazolidinone using nucleophiles: facile synthesis, cytotoxic evaluation, apoptosis, cell cycle and molecular docking studies of a novel series of azole, azine, azepine and pyran derivatives</atitle><jtitle>RSC advances</jtitle><addtitle>RSC Adv</addtitle><date>2023-06-15</date><risdate>2023</risdate><volume>13</volume><issue>27</issue><spage>18658</spage><epage>18675</epage><pages>18658-18675</pages><issn>2046-2069</issn><eissn>2046-2069</eissn><abstract>A convenient synthetic approach for construction of a novel series of substituted azoles, azines, azepines and pyrans clubbed with a morpholinothiazolidinone hybrid was achieved. The methodology depended on ring-opening and ring-closure (RORC) of chromone ring in 2-(morpholinoimino)-5-[(4-oxo-4
H
-chromen-3-yl)methylene]-3-phenylthiazolidin-4-one (
3
) through its reaction with a series of nitrogen and carbon nucleophiles under mild reaction conditions. The cytotoxic effects of all products were evaluated against three cancerous cell lines (MCF-7, HepG-2 and SKOV-3) by the standard SRB method. Fortunately, the products
7
,
11
,
12
,
15
,
19
,
22
,
26
and
28
were found to be the most active against all cancer cell lines, comparable to doxorubicin. Apoptosis was determined using flow cytometry along with cell cycle analysis and supported by molecular docking. The products
7
,
11
,
12
,
15
,
19
,
22
,
26
and
28
induced a significant early-and late-apoptotic effect against all tumor cells. In addition, these products preferred to arrest all cancer cells in the G1 and G2 phases. Finally, molecular docking was attempted to investigate the binding mode of products
12
and
22
with p53-MDM2 protein receptor.
Construction of a novel series of substituted azoles, azines, azepines and pyrans clubbed with a morpholinothiazolidinone hybrid with anticancer properties, was achieved.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>37346943</pmid><doi>10.1039/d3ra02777e</doi><tpages>18</tpages><orcidid>https://orcid.org/0000-0002-7992-3478</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2046-2069 |
| ispartof | RSC advances, 2023-06, Vol.13 (27), p.18658-18675 |
| issn | 2046-2069 2046-2069 |
| language | eng |
| recordid | cdi_crossref_primary_10_1039_D3RA02777E |
| source | Open Access: PubMed Central |
| subjects | Apoptosis Azines Cancer Cell cycle Chemistry Cytotoxicity Doxorubicin Flow cytometry Heterocyclic compounds Molecular docking Nucleophiles Ring opening |
| title | Recyclization of morpholinochromonylidene-thiazolidinone using nucleophiles: facile synthesis, cytotoxic evaluation, apoptosis, cell cycle and molecular docking studies of a novel series of azole, azine, azepine and pyran derivatives |
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