Synthesis and Characterization of Macrocyclic Chiral Troger's Base Phenhomazine Candidates as Anticancer Agent
1,4,7,10-Tetraoxa[10](2,8)trogerophane 5 was synthesized from its corresponding precursors. Heating of 2 with p-nitrophenoxide afforded bis(p-nitrophenyl)ether 3, which was treated with hydrazine hydrate to give bis(p-aminophenyl)ether 4. Treatment of 4 with paraformaldehyde and triflouroacetic anhy...
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| Veröffentlicht in: | Frontiers in chemistry 2021-01, Vol.8, p.633065-633065, Article 633065 |
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| creator | Ibrahim, Alhussein A. Ali, Korany A. Hafez, Naglaa A. Abdel Elsayed, Mohamed A. Mohamed, Khalid M. H. Hosni, Hanaa M. Amr, Abd El-Galil E. Elsayed, Elsayed A. |
| description | 1,4,7,10-Tetraoxa[10](2,8)trogerophane 5 was synthesized from its corresponding precursors. Heating of 2 with p-nitrophenoxide afforded bis(p-nitrophenyl)ether 3, which was treated with hydrazine hydrate to give bis(p-aminophenyl)ether 4. Treatment of 4 with paraformaldehyde and triflouroacetic anhydride gave trogerophane 5. Reaction of 5 with trifluroacetic anhydride afforded phenhomazine derivative 6, which was treated with potassium carbonate to afford tetrahydrophenhomazine 7. Finally, reaction of 7 with phenacylchloride, bromoacetic acid, or ethyl bromoacetate in the presence of triethyl amine under reflux, afforded the corresponding macrocyclic compounds 8, 9 and 10, respectively. The synthesized trogerophane,precursors and its newly synthesized phenhomazines derivatives were screened for anticancer activity. Results revealed that 1,4,7,10-tetraoxa[10](2,8)trogerophane had a promising selectivity towards colon cancer cell line with an IC50 of 92.7 mu g/ml. |
| doi_str_mv | 10.3389/fchem.2020.633065 |
| format | Article |
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Abdel ; Elsayed, Mohamed A. ; Mohamed, Khalid M. H. ; Hosni, Hanaa M. ; Amr, Abd El-Galil E. ; Elsayed, Elsayed A.</creator><creatorcontrib>Ibrahim, Alhussein A. ; Ali, Korany A. ; Hafez, Naglaa A. Abdel ; Elsayed, Mohamed A. ; Mohamed, Khalid M. H. ; Hosni, Hanaa M. ; Amr, Abd El-Galil E. ; Elsayed, Elsayed A.</creatorcontrib><description>1,4,7,10-Tetraoxa[10](2,8)trogerophane 5 was synthesized from its corresponding precursors. Heating of 2 with p-nitrophenoxide afforded bis(p-nitrophenyl)ether 3, which was treated with hydrazine hydrate to give bis(p-aminophenyl)ether 4. Treatment of 4 with paraformaldehyde and triflouroacetic anhydride gave trogerophane 5. Reaction of 5 with trifluroacetic anhydride afforded phenhomazine derivative 6, which was treated with potassium carbonate to afford tetrahydrophenhomazine 7. Finally, reaction of 7 with phenacylchloride, bromoacetic acid, or ethyl bromoacetate in the presence of triethyl amine under reflux, afforded the corresponding macrocyclic compounds 8, 9 and 10, respectively. The synthesized trogerophane,precursors and its newly synthesized phenhomazines derivatives were screened for anticancer activity. Results revealed that 1,4,7,10-tetraoxa[10](2,8)trogerophane had a promising selectivity towards colon cancer cell line with an IC50 of 92.7 mu g/ml.</description><identifier>ISSN: 2296-2646</identifier><identifier>EISSN: 2296-2646</identifier><identifier>DOI: 10.3389/fchem.2020.633065</identifier><identifier>PMID: 33748073</identifier><language>eng</language><publisher>LAUSANNE: Frontiers Media Sa</publisher><subject>anticancer activity ; Chemistry ; Chemistry, Multidisciplinary ; chiral macrocyclic ; phenhomazines ; Physical Sciences ; Science & Technology ; trögerophane ; tröger’s base</subject><ispartof>Frontiers in chemistry, 2021-01, Vol.8, p.633065-633065, Article 633065</ispartof><rights>Copyright © 2021 Ibrahim, Ali, Hafez, Elsayed, Mohamed, Hosni, Amr and Elsayed.</rights><rights>Copyright © 2021 Ibrahim, Ali, Hafez, Elsayed, Mohamed, Hosni, Amr and Elsayed. 2021 Ibrahim, Ali, Hafez, Elsayed, Mohamed, Hosni, Amr and Elsayed</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>true</woscitedreferencessubscribed><woscitedreferencescount>1</woscitedreferencescount><woscitedreferencesoriginalsourcerecordid>wos000616816400001</woscitedreferencesoriginalsourcerecordid><citedby>FETCH-LOGICAL-c465t-9010d8892e474a14db2f669f80461d8880b7b9ddf3b894f98a43e7e049e21eb43</citedby><cites>FETCH-LOGICAL-c465t-9010d8892e474a14db2f669f80461d8880b7b9ddf3b894f98a43e7e049e21eb43</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC7976657/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC7976657/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,315,728,781,785,865,886,2103,2115,27929,27930,39263,53796,53798</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33748073$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ibrahim, Alhussein A.</creatorcontrib><creatorcontrib>Ali, Korany A.</creatorcontrib><creatorcontrib>Hafez, Naglaa A. Abdel</creatorcontrib><creatorcontrib>Elsayed, Mohamed A.</creatorcontrib><creatorcontrib>Mohamed, Khalid M. H.</creatorcontrib><creatorcontrib>Hosni, Hanaa M.</creatorcontrib><creatorcontrib>Amr, Abd El-Galil E.</creatorcontrib><creatorcontrib>Elsayed, Elsayed A.</creatorcontrib><title>Synthesis and Characterization of Macrocyclic Chiral Troger's Base Phenhomazine Candidates as Anticancer Agent</title><title>Frontiers in chemistry</title><addtitle>FRONT CHEM</addtitle><addtitle>Front Chem</addtitle><description>1,4,7,10-Tetraoxa[10](2,8)trogerophane 5 was synthesized from its corresponding precursors. Heating of 2 with p-nitrophenoxide afforded bis(p-nitrophenyl)ether 3, which was treated with hydrazine hydrate to give bis(p-aminophenyl)ether 4. Treatment of 4 with paraformaldehyde and triflouroacetic anhydride gave trogerophane 5. Reaction of 5 with trifluroacetic anhydride afforded phenhomazine derivative 6, which was treated with potassium carbonate to afford tetrahydrophenhomazine 7. Finally, reaction of 7 with phenacylchloride, bromoacetic acid, or ethyl bromoacetate in the presence of triethyl amine under reflux, afforded the corresponding macrocyclic compounds 8, 9 and 10, respectively. The synthesized trogerophane,precursors and its newly synthesized phenhomazines derivatives were screened for anticancer activity. Results revealed that 1,4,7,10-tetraoxa[10](2,8)trogerophane had a promising selectivity towards colon cancer cell line with an IC50 of 92.7 mu g/ml.</description><subject>anticancer activity</subject><subject>Chemistry</subject><subject>Chemistry, Multidisciplinary</subject><subject>chiral macrocyclic</subject><subject>phenhomazines</subject><subject>Physical Sciences</subject><subject>Science & Technology</subject><subject>trögerophane</subject><subject>tröger’s base</subject><issn>2296-2646</issn><issn>2296-2646</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>HGBXW</sourceid><sourceid>DOA</sourceid><recordid>eNqNkk1vEzEQhlcIRKvSH8AF7Q0klDD-iD8uSGFFS6UikChny-udzbra2MXegNJfj5OUqL3hiz_m9WPPvFNVrwnMGVP6Q-8GXM8pUJgLxkAsnlWnlGoxo4KL54_WJ9V5zrcAQChhnMLL6oQxyRVIdlqFH9swDZh9rm3o6mawyboJk7-3k4-hjn391boU3daN3pW4T3asb1JcYXqb6082Y_19wDDEtb33AeumYHxnJyzAXC_D5J0NDlO9XGGYXlUvejtmPH-Yz6qfF59vmi-z62-XV83yeua4WEwzDQQ6pTRFLrklvGtpL4TuFXBBSkBBK1vddT1rlea9VpYzlAhcIyXYcnZWXR24XbS35i75tU1bE603-4OYVsam8rURjQCGRPeSlsGlgHYhgaJroeydZV1hfTyw7jbtGjtX0ig1eAJ9Ggl-MKv420gthVjIAnj3AEjx1wbzZNY-OxxHGzBusqELYCU7pnZScpCWkuecsD8-Q8DsbDd7283OdnOwvdx58_h_xxv_TC6C9wfBH2xjn53HYshRVhpDEKGI4LDrkaJW_69u_LTvkyZuwsT-At3oyrc</recordid><startdate>20210128</startdate><enddate>20210128</enddate><creator>Ibrahim, Alhussein A.</creator><creator>Ali, Korany A.</creator><creator>Hafez, Naglaa A. Abdel</creator><creator>Elsayed, Mohamed A.</creator><creator>Mohamed, Khalid M. H.</creator><creator>Hosni, Hanaa M.</creator><creator>Amr, Abd El-Galil E.</creator><creator>Elsayed, Elsayed A.</creator><general>Frontiers Media Sa</general><general>Frontiers Media S.A</general><scope>BLEPL</scope><scope>DTL</scope><scope>HGBXW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>5PM</scope><scope>DOA</scope></search><sort><creationdate>20210128</creationdate><title>Synthesis and Characterization of Macrocyclic Chiral Troger's Base Phenhomazine Candidates as Anticancer Agent</title><author>Ibrahim, Alhussein A. ; Ali, Korany A. ; Hafez, Naglaa A. Abdel ; Elsayed, Mohamed A. ; Mohamed, Khalid M. H. ; Hosni, Hanaa M. ; Amr, Abd El-Galil E. ; Elsayed, Elsayed A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c465t-9010d8892e474a14db2f669f80461d8880b7b9ddf3b894f98a43e7e049e21eb43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>anticancer activity</topic><topic>Chemistry</topic><topic>Chemistry, Multidisciplinary</topic><topic>chiral macrocyclic</topic><topic>phenhomazines</topic><topic>Physical Sciences</topic><topic>Science & Technology</topic><topic>trögerophane</topic><topic>tröger’s base</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ibrahim, Alhussein A.</creatorcontrib><creatorcontrib>Ali, Korany A.</creatorcontrib><creatorcontrib>Hafez, Naglaa A. Abdel</creatorcontrib><creatorcontrib>Elsayed, Mohamed A.</creatorcontrib><creatorcontrib>Mohamed, Khalid M. H.</creatorcontrib><creatorcontrib>Hosni, Hanaa M.</creatorcontrib><creatorcontrib>Amr, Abd El-Galil E.</creatorcontrib><creatorcontrib>Elsayed, Elsayed A.</creatorcontrib><collection>Web of Science Core Collection</collection><collection>Science Citation Index Expanded</collection><collection>Web of Science - Science Citation Index Expanded - 2021</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><collection>DOAJ Directory of Open Access Journals</collection><jtitle>Frontiers in chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ibrahim, Alhussein A.</au><au>Ali, Korany A.</au><au>Hafez, Naglaa A. Abdel</au><au>Elsayed, Mohamed A.</au><au>Mohamed, Khalid M. H.</au><au>Hosni, Hanaa M.</au><au>Amr, Abd El-Galil E.</au><au>Elsayed, Elsayed A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Characterization of Macrocyclic Chiral Troger's Base Phenhomazine Candidates as Anticancer Agent</atitle><jtitle>Frontiers in chemistry</jtitle><stitle>FRONT CHEM</stitle><addtitle>Front Chem</addtitle><date>2021-01-28</date><risdate>2021</risdate><volume>8</volume><spage>633065</spage><epage>633065</epage><pages>633065-633065</pages><artnum>633065</artnum><issn>2296-2646</issn><eissn>2296-2646</eissn><abstract>1,4,7,10-Tetraoxa[10](2,8)trogerophane 5 was synthesized from its corresponding precursors. Heating of 2 with p-nitrophenoxide afforded bis(p-nitrophenyl)ether 3, which was treated with hydrazine hydrate to give bis(p-aminophenyl)ether 4. Treatment of 4 with paraformaldehyde and triflouroacetic anhydride gave trogerophane 5. Reaction of 5 with trifluroacetic anhydride afforded phenhomazine derivative 6, which was treated with potassium carbonate to afford tetrahydrophenhomazine 7. Finally, reaction of 7 with phenacylchloride, bromoacetic acid, or ethyl bromoacetate in the presence of triethyl amine under reflux, afforded the corresponding macrocyclic compounds 8, 9 and 10, respectively. The synthesized trogerophane,precursors and its newly synthesized phenhomazines derivatives were screened for anticancer activity. Results revealed that 1,4,7,10-tetraoxa[10](2,8)trogerophane had a promising selectivity towards colon cancer cell line with an IC50 of 92.7 mu g/ml.</abstract><cop>LAUSANNE</cop><pub>Frontiers Media Sa</pub><pmid>33748073</pmid><doi>10.3389/fchem.2020.633065</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | anticancer activity Chemistry Chemistry, Multidisciplinary chiral macrocyclic phenhomazines Physical Sciences Science & Technology trögerophane tröger’s base |
| title | Synthesis and Characterization of Macrocyclic Chiral Troger's Base Phenhomazine Candidates as Anticancer Agent |
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