Synthesis, characterization, computational studies and DPPH scavenging activity of some triazatetracyclic derivatives
Some dihydrobenzo[4,5]imidazo[1,2-c]quinazolines have been synthesized from aldehydes and ketones, using the ketones as both reagents and solvents and tetrahydrofuran (THF) as the solvent for the aldehydes, to yield the triazatetracyclics. The compounds have been characterized with spectroscopy and...
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| Veröffentlicht in: | Journal of the Iranian Chemical Society 2021, Vol.18 (8), p.1979-1995 |
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| container_end_page | 1995 |
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| container_issue | 8 |
| container_start_page | 1979 |
| container_title | Journal of the Iranian Chemical Society |
| container_volume | 18 |
| creator | Odame, F. Hosten, Eric C. Betz, R. Krause, J. Frost, Carminita L. Lobb, K. Tshentu, Zenixole R. |
| description | Some dihydrobenzo[4,5]imidazo[1,2-c]quinazolines have been synthesized from aldehydes and ketones, using the ketones as both reagents and solvents and tetrahydrofuran (THF) as the solvent for the aldehydes, to yield the triazatetracyclics. The compounds have been characterized with spectroscopy and microanalysis. The crystal structures of 9,9-dimethyl-8,10,17-triazatetracyclo[8.7.0
2,7
.0
11,16
]heptadeca-1(17),2,4,6,11(16),12,14-heptaene (
I
), 9-butyl-9-methyl-8,10,17-triazatetracyclo[8.7.0.0
2
,
7
.0
11,16
]heptadeca-(17),2,4,6,11(16),12,14-heptaene (
III
) and 9-phenyl-8,10,17-triazatetracyclo[8.7.0 0
2 7
.0
11,16
]heptadeca-1(17),2,4,6,11(16),12,14-heptaene (
VIII
) have been discussed. The computed NMR, IR, molecular electrostatic potential and frontier molecular orbitals of compounds
I
,
III
and
VIII
have been discussed. The M06 functional gave most of its values closest to the experimental values for the bond lengths and bond angles of compounds
I
and
III
. For compound
VIII
, none of the functionals gave values for bond lengths and bond angles that were consistent with the experimental values, but M06 gave values closest to experimental values. The 1,1-diphenyl-2-picrylhydrazyl
(
DPPH) scavenging activity of the triazatetracyclics showed that compound
I
exhibits significant DPPH scavenging activity with an IC
50
of 56.18 µM compared to 2.37 µM for ascorbic acid. |
| doi_str_mv | 10.1007/s13738-021-02158-3 |
| format | Article |
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2,7
.0
11,16
]heptadeca-1(17),2,4,6,11(16),12,14-heptaene (
I
), 9-butyl-9-methyl-8,10,17-triazatetracyclo[8.7.0.0
2
,
7
.0
11,16
]heptadeca-(17),2,4,6,11(16),12,14-heptaene (
III
) and 9-phenyl-8,10,17-triazatetracyclo[8.7.0 0
2 7
.0
11,16
]heptadeca-1(17),2,4,6,11(16),12,14-heptaene (
VIII
) have been discussed. The computed NMR, IR, molecular electrostatic potential and frontier molecular orbitals of compounds
I
,
III
and
VIII
have been discussed. The M06 functional gave most of its values closest to the experimental values for the bond lengths and bond angles of compounds
I
and
III
. For compound
VIII
, none of the functionals gave values for bond lengths and bond angles that were consistent with the experimental values, but M06 gave values closest to experimental values. The 1,1-diphenyl-2-picrylhydrazyl
(
DPPH) scavenging activity of the triazatetracyclics showed that compound
I
exhibits significant DPPH scavenging activity with an IC
50
of 56.18 µM compared to 2.37 µM for ascorbic acid.</description><identifier>ISSN: 1735-207X</identifier><identifier>EISSN: 1735-2428</identifier><identifier>DOI: 10.1007/s13738-021-02158-3</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer Berlin Heidelberg</publisher><subject>Aldehydes ; Analytical Chemistry ; Ascorbic acid ; Biochemistry ; Chemical synthesis ; Chemistry ; Chemistry and Materials Science ; Crystal structure ; Inorganic Chemistry ; Ketones ; Molecular orbitals ; NMR ; Nuclear magnetic resonance ; Organic Chemistry ; Original Paper ; Physical Chemistry ; Reagents ; Scavenging ; Solvents ; Tetrahydrofuran</subject><ispartof>Journal of the Iranian Chemical Society, 2021, Vol.18 (8), p.1979-1995</ispartof><rights>Iranian Chemical Society 2021</rights><rights>Iranian Chemical Society 2021.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c319t-7a5c830683d9492533849934b4b39bdda1414c6092d598198832d7f9c4e01d4d3</citedby><cites>FETCH-LOGICAL-c319t-7a5c830683d9492533849934b4b39bdda1414c6092d598198832d7f9c4e01d4d3</cites><orcidid>0000-0001-7651-8816</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://link.springer.com/content/pdf/10.1007/s13738-021-02158-3$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s13738-021-02158-3$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,780,784,27923,27924,41487,42556,51318</link.rule.ids></links><search><creatorcontrib>Odame, F.</creatorcontrib><creatorcontrib>Hosten, Eric C.</creatorcontrib><creatorcontrib>Betz, R.</creatorcontrib><creatorcontrib>Krause, J.</creatorcontrib><creatorcontrib>Frost, Carminita L.</creatorcontrib><creatorcontrib>Lobb, K.</creatorcontrib><creatorcontrib>Tshentu, Zenixole R.</creatorcontrib><title>Synthesis, characterization, computational studies and DPPH scavenging activity of some triazatetracyclic derivatives</title><title>Journal of the Iranian Chemical Society</title><addtitle>J IRAN CHEM SOC</addtitle><description>Some dihydrobenzo[4,5]imidazo[1,2-c]quinazolines have been synthesized from aldehydes and ketones, using the ketones as both reagents and solvents and tetrahydrofuran (THF) as the solvent for the aldehydes, to yield the triazatetracyclics. The compounds have been characterized with spectroscopy and microanalysis. The crystal structures of 9,9-dimethyl-8,10,17-triazatetracyclo[8.7.0
2,7
.0
11,16
]heptadeca-1(17),2,4,6,11(16),12,14-heptaene (
I
), 9-butyl-9-methyl-8,10,17-triazatetracyclo[8.7.0.0
2
,
7
.0
11,16
]heptadeca-(17),2,4,6,11(16),12,14-heptaene (
III
) and 9-phenyl-8,10,17-triazatetracyclo[8.7.0 0
2 7
.0
11,16
]heptadeca-1(17),2,4,6,11(16),12,14-heptaene (
VIII
) have been discussed. The computed NMR, IR, molecular electrostatic potential and frontier molecular orbitals of compounds
I
,
III
and
VIII
have been discussed. The M06 functional gave most of its values closest to the experimental values for the bond lengths and bond angles of compounds
I
and
III
. For compound
VIII
, none of the functionals gave values for bond lengths and bond angles that were consistent with the experimental values, but M06 gave values closest to experimental values. The 1,1-diphenyl-2-picrylhydrazyl
(
DPPH) scavenging activity of the triazatetracyclics showed that compound
I
exhibits significant DPPH scavenging activity with an IC
50
of 56.18 µM compared to 2.37 µM for ascorbic acid.</description><subject>Aldehydes</subject><subject>Analytical Chemistry</subject><subject>Ascorbic acid</subject><subject>Biochemistry</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Crystal structure</subject><subject>Inorganic Chemistry</subject><subject>Ketones</subject><subject>Molecular orbitals</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Organic Chemistry</subject><subject>Original Paper</subject><subject>Physical Chemistry</subject><subject>Reagents</subject><subject>Scavenging</subject><subject>Solvents</subject><subject>Tetrahydrofuran</subject><issn>1735-207X</issn><issn>1735-2428</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNp9kEtLAzEUhQdRsFb_gKuAW0fzbJKl1EeFggUV3IU0ybQp7UxNMgPjrzdtFXcuLvfBOR_cUxSXCN4gCPltRIQTUUKMdsVESY6KAeKElZhicfw7Q_5xWpzFuIKQccjooGhf-zotXfTxGpilDtokF_yXTr6p86XZbNu0X_QaxNRa7yLQtQX3s9kERKM7Vy98vQDZ5zufetBUIDYbB1LwOmNcysjerL0BNoO7zOpcPC9OKr2O7uKnD4v3x4e38aScvjw9j--mpSFIppJrZgSBI0GspBIzQgSVktA5nRM5t1YjiqgZQYktkwJJIQi2vJKGOogstWRYXB2429B8ti4mtWrakH-JCjMqRpRiLrMKH1QmNDEGV6lt8BsdeoWg2sWrDvGqHK3ax6tINpGDKWZxvXDhD_2P6xt3vH76</recordid><startdate>2021</startdate><enddate>2021</enddate><creator>Odame, F.</creator><creator>Hosten, Eric C.</creator><creator>Betz, R.</creator><creator>Krause, J.</creator><creator>Frost, Carminita L.</creator><creator>Lobb, K.</creator><creator>Tshentu, Zenixole R.</creator><general>Springer Berlin Heidelberg</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0001-7651-8816</orcidid></search><sort><creationdate>2021</creationdate><title>Synthesis, characterization, computational studies and DPPH scavenging activity of some triazatetracyclic derivatives</title><author>Odame, F. ; Hosten, Eric C. ; Betz, R. ; Krause, J. ; Frost, Carminita L. ; Lobb, K. ; Tshentu, Zenixole R.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c319t-7a5c830683d9492533849934b4b39bdda1414c6092d598198832d7f9c4e01d4d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Aldehydes</topic><topic>Analytical Chemistry</topic><topic>Ascorbic acid</topic><topic>Biochemistry</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Crystal structure</topic><topic>Inorganic Chemistry</topic><topic>Ketones</topic><topic>Molecular orbitals</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Organic Chemistry</topic><topic>Original Paper</topic><topic>Physical Chemistry</topic><topic>Reagents</topic><topic>Scavenging</topic><topic>Solvents</topic><topic>Tetrahydrofuran</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Odame, F.</creatorcontrib><creatorcontrib>Hosten, Eric C.</creatorcontrib><creatorcontrib>Betz, R.</creatorcontrib><creatorcontrib>Krause, J.</creatorcontrib><creatorcontrib>Frost, Carminita L.</creatorcontrib><creatorcontrib>Lobb, K.</creatorcontrib><creatorcontrib>Tshentu, Zenixole R.</creatorcontrib><collection>CrossRef</collection><jtitle>Journal of the Iranian Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Odame, F.</au><au>Hosten, Eric C.</au><au>Betz, R.</au><au>Krause, J.</au><au>Frost, Carminita L.</au><au>Lobb, K.</au><au>Tshentu, Zenixole R.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, characterization, computational studies and DPPH scavenging activity of some triazatetracyclic derivatives</atitle><jtitle>Journal of the Iranian Chemical Society</jtitle><stitle>J IRAN CHEM SOC</stitle><date>2021</date><risdate>2021</risdate><volume>18</volume><issue>8</issue><spage>1979</spage><epage>1995</epage><pages>1979-1995</pages><issn>1735-207X</issn><eissn>1735-2428</eissn><abstract>Some dihydrobenzo[4,5]imidazo[1,2-c]quinazolines have been synthesized from aldehydes and ketones, using the ketones as both reagents and solvents and tetrahydrofuran (THF) as the solvent for the aldehydes, to yield the triazatetracyclics. The compounds have been characterized with spectroscopy and microanalysis. The crystal structures of 9,9-dimethyl-8,10,17-triazatetracyclo[8.7.0
2,7
.0
11,16
]heptadeca-1(17),2,4,6,11(16),12,14-heptaene (
I
), 9-butyl-9-methyl-8,10,17-triazatetracyclo[8.7.0.0
2
,
7
.0
11,16
]heptadeca-(17),2,4,6,11(16),12,14-heptaene (
III
) and 9-phenyl-8,10,17-triazatetracyclo[8.7.0 0
2 7
.0
11,16
]heptadeca-1(17),2,4,6,11(16),12,14-heptaene (
VIII
) have been discussed. The computed NMR, IR, molecular electrostatic potential and frontier molecular orbitals of compounds
I
,
III
and
VIII
have been discussed. The M06 functional gave most of its values closest to the experimental values for the bond lengths and bond angles of compounds
I
and
III
. For compound
VIII
, none of the functionals gave values for bond lengths and bond angles that were consistent with the experimental values, but M06 gave values closest to experimental values. The 1,1-diphenyl-2-picrylhydrazyl
(
DPPH) scavenging activity of the triazatetracyclics showed that compound
I
exhibits significant DPPH scavenging activity with an IC
50
of 56.18 µM compared to 2.37 µM for ascorbic acid.</abstract><cop>Berlin/Heidelberg</cop><pub>Springer Berlin Heidelberg</pub><doi>10.1007/s13738-021-02158-3</doi><tpages>17</tpages><orcidid>https://orcid.org/0000-0001-7651-8816</orcidid></addata></record> |
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| language | eng |
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| source | SpringerLink Journals - AutoHoldings |
| subjects | Aldehydes Analytical Chemistry Ascorbic acid Biochemistry Chemical synthesis Chemistry Chemistry and Materials Science Crystal structure Inorganic Chemistry Ketones Molecular orbitals NMR Nuclear magnetic resonance Organic Chemistry Original Paper Physical Chemistry Reagents Scavenging Solvents Tetrahydrofuran |
| title | Synthesis, characterization, computational studies and DPPH scavenging activity of some triazatetracyclic derivatives |
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