Thiochromene candidates: design, synthesis, antimicrobial potential and in silico docking study
New sets of thiochromenes hybridized with five-membered rings as pyrazole and oxazole and/or six-membered ring as pyrimidine and thiopyrimidine were constructed. The novel constructed compounds were evaluated for their antimicrobial potential against B. subtilis and S. aureus as examples of gram-pos...
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| Veröffentlicht in: | Journal of the Iranian Chemical Society 2022-04, Vol.19 (4), p.1413-1423 |
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| creator | Bakr, Rania B. Azab, Islam H. El Elkanzi, Nadia A. A. |
| description | New sets of thiochromenes hybridized with five-membered rings as pyrazole and oxazole and/or six-membered ring as pyrimidine and thiopyrimidine were constructed. The novel constructed compounds were evaluated for their antimicrobial potential against
B. subtilis
and
S. aureus
as examples of gram-positive-bacteria,
E. coli
and
P. aeruginosa
as examples of gram-negative bacteria in addition to
A. flavus
and
C. albicans
as fungal strains. The results recorded promising antimicrobial potential with inhibition zone diameter range from 8 to 25 mm against the tested bacteria. Regarding antifungal activity, all the screened compounds revealed antifungal effect against
A. flavus
except thiochromene derivative
4
with zone of inhibition ranged from 9 to 16 mm. Moreover, all compounds recorded moderate to high antifungal potential towards
C. albicans
(ZI range = 8–19 mm) except thioxopyrazolothiochromene derivative
6
which did not exhibit any effect. To suggest mode of action of these candidates as antimicrobials, in silico docking study was carried out inside dihydropteroate synthase enzyme. Compound
8c
recorded the best binding energy score (−5.47 kcal/mol) forming good fitting within DHPS active site. |
| doi_str_mv | 10.1007/s13738-021-02391-w |
| format | Article |
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B. subtilis
and
S. aureus
as examples of gram-positive-bacteria,
E. coli
and
P. aeruginosa
as examples of gram-negative bacteria in addition to
A. flavus
and
C. albicans
as fungal strains. The results recorded promising antimicrobial potential with inhibition zone diameter range from 8 to 25 mm against the tested bacteria. Regarding antifungal activity, all the screened compounds revealed antifungal effect against
A. flavus
except thiochromene derivative
4
with zone of inhibition ranged from 9 to 16 mm. Moreover, all compounds recorded moderate to high antifungal potential towards
C. albicans
(ZI range = 8–19 mm) except thioxopyrazolothiochromene derivative
6
which did not exhibit any effect. To suggest mode of action of these candidates as antimicrobials, in silico docking study was carried out inside dihydropteroate synthase enzyme. Compound
8c
recorded the best binding energy score (−5.47 kcal/mol) forming good fitting within DHPS active site.</description><identifier>ISSN: 1735-207X</identifier><identifier>EISSN: 1735-2428</identifier><identifier>DOI: 10.1007/s13738-021-02391-w</identifier><language>eng</language><publisher>Berlin/Heidelberg: Springer Berlin Heidelberg</publisher><subject>Analytical Chemistry ; Antiinfectives and antibacterials ; Bacteria ; Biochemistry ; Chemical synthesis ; Chemistry ; Chemistry and Materials Science ; Docking ; E coli ; Fungicides ; Inorganic Chemistry ; Organic Chemistry ; Original Paper ; Oxazole ; Physical Chemistry ; Pyrazole</subject><ispartof>Journal of the Iranian Chemical Society, 2022-04, Vol.19 (4), p.1413-1423</ispartof><rights>Iranian Chemical Society 2021</rights><rights>Iranian Chemical Society 2021.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c319t-2de0a0edae8ca9bf1a5b419ce4003b6c5beccaab8c8a1a142f91cc79bdf2d9a83</citedby><cites>FETCH-LOGICAL-c319t-2de0a0edae8ca9bf1a5b419ce4003b6c5beccaab8c8a1a142f91cc79bdf2d9a83</cites><orcidid>0000-0002-1687-1834 ; 0000-0001-6564-1712</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/s13738-021-02391-w$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s13738-021-02391-w$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>315,782,786,27933,27934,41497,42566,51328</link.rule.ids></links><search><creatorcontrib>Bakr, Rania B.</creatorcontrib><creatorcontrib>Azab, Islam H. El</creatorcontrib><creatorcontrib>Elkanzi, Nadia A. A.</creatorcontrib><title>Thiochromene candidates: design, synthesis, antimicrobial potential and in silico docking study</title><title>Journal of the Iranian Chemical Society</title><addtitle>J IRAN CHEM SOC</addtitle><description>New sets of thiochromenes hybridized with five-membered rings as pyrazole and oxazole and/or six-membered ring as pyrimidine and thiopyrimidine were constructed. The novel constructed compounds were evaluated for their antimicrobial potential against
B. subtilis
and
S. aureus
as examples of gram-positive-bacteria,
E. coli
and
P. aeruginosa
as examples of gram-negative bacteria in addition to
A. flavus
and
C. albicans
as fungal strains. The results recorded promising antimicrobial potential with inhibition zone diameter range from 8 to 25 mm against the tested bacteria. Regarding antifungal activity, all the screened compounds revealed antifungal effect against
A. flavus
except thiochromene derivative
4
with zone of inhibition ranged from 9 to 16 mm. Moreover, all compounds recorded moderate to high antifungal potential towards
C. albicans
(ZI range = 8–19 mm) except thioxopyrazolothiochromene derivative
6
which did not exhibit any effect. To suggest mode of action of these candidates as antimicrobials, in silico docking study was carried out inside dihydropteroate synthase enzyme. Compound
8c
recorded the best binding energy score (−5.47 kcal/mol) forming good fitting within DHPS active site.</description><subject>Analytical Chemistry</subject><subject>Antiinfectives and antibacterials</subject><subject>Bacteria</subject><subject>Biochemistry</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Docking</subject><subject>E coli</subject><subject>Fungicides</subject><subject>Inorganic Chemistry</subject><subject>Organic Chemistry</subject><subject>Original Paper</subject><subject>Oxazole</subject><subject>Physical Chemistry</subject><subject>Pyrazole</subject><issn>1735-207X</issn><issn>1735-2428</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNp9kE1LAzEQhoMoWKt_wFPAa1fzsbvZeJPiFxS8VPAWZpNsm9omNdlS-u-NruLNwzAvw_vOMA9Cl5RcU0LETaJc8KYgjObikhb7IzSiglcFK1lz_KuJeDtFZymtCKkEqcoRUvOlC3oZw8Z6izV44wz0Nt1iY5Nb-AlOB98vs04TDL53G6djaB2s8Tb0Ng-yyinsPE5u7XTAJuh35xc49TtzOEcnHayTvfjpY_T6cD-fPhWzl8fn6d2s0JzKvmDGEiDWgG00yLajULUlldqWhPC21lVrtQZoG90ABVqyTlKthWxNx4yEho_R1bB3G8PHzqZercIu-nxSsZrLSoia1tnFBlf-IaVoO7WNbgPxoChRXyDVAFJlkOobpNrnEB9CKZv9wsa_1f-kPgHCgHnh</recordid><startdate>20220401</startdate><enddate>20220401</enddate><creator>Bakr, Rania B.</creator><creator>Azab, Islam H. El</creator><creator>Elkanzi, Nadia A. A.</creator><general>Springer Berlin Heidelberg</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-1687-1834</orcidid><orcidid>https://orcid.org/0000-0001-6564-1712</orcidid></search><sort><creationdate>20220401</creationdate><title>Thiochromene candidates: design, synthesis, antimicrobial potential and in silico docking study</title><author>Bakr, Rania B. ; Azab, Islam H. El ; Elkanzi, Nadia A. A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c319t-2de0a0edae8ca9bf1a5b419ce4003b6c5beccaab8c8a1a142f91cc79bdf2d9a83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Analytical Chemistry</topic><topic>Antiinfectives and antibacterials</topic><topic>Bacteria</topic><topic>Biochemistry</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Docking</topic><topic>E coli</topic><topic>Fungicides</topic><topic>Inorganic Chemistry</topic><topic>Organic Chemistry</topic><topic>Original Paper</topic><topic>Oxazole</topic><topic>Physical Chemistry</topic><topic>Pyrazole</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bakr, Rania B.</creatorcontrib><creatorcontrib>Azab, Islam H. El</creatorcontrib><creatorcontrib>Elkanzi, Nadia A. A.</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>Bakr, Rania B.</au><au>Azab, Islam H. El</au><au>Elkanzi, Nadia A. A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Thiochromene candidates: design, synthesis, antimicrobial potential and in silico docking study</atitle><jtitle>Journal of the Iranian Chemical Society</jtitle><stitle>J IRAN CHEM SOC</stitle><date>2022-04-01</date><risdate>2022</risdate><volume>19</volume><issue>4</issue><spage>1413</spage><epage>1423</epage><pages>1413-1423</pages><issn>1735-207X</issn><eissn>1735-2428</eissn><abstract>New sets of thiochromenes hybridized with five-membered rings as pyrazole and oxazole and/or six-membered ring as pyrimidine and thiopyrimidine were constructed. The novel constructed compounds were evaluated for their antimicrobial potential against
B. subtilis
and
S. aureus
as examples of gram-positive-bacteria,
E. coli
and
P. aeruginosa
as examples of gram-negative bacteria in addition to
A. flavus
and
C. albicans
as fungal strains. The results recorded promising antimicrobial potential with inhibition zone diameter range from 8 to 25 mm against the tested bacteria. Regarding antifungal activity, all the screened compounds revealed antifungal effect against
A. flavus
except thiochromene derivative
4
with zone of inhibition ranged from 9 to 16 mm. Moreover, all compounds recorded moderate to high antifungal potential towards
C. albicans
(ZI range = 8–19 mm) except thioxopyrazolothiochromene derivative
6
which did not exhibit any effect. To suggest mode of action of these candidates as antimicrobials, in silico docking study was carried out inside dihydropteroate synthase enzyme. Compound
8c
recorded the best binding energy score (−5.47 kcal/mol) forming good fitting within DHPS active site.</abstract><cop>Berlin/Heidelberg</cop><pub>Springer Berlin Heidelberg</pub><doi>10.1007/s13738-021-02391-w</doi><tpages>11</tpages><orcidid>https://orcid.org/0000-0002-1687-1834</orcidid><orcidid>https://orcid.org/0000-0001-6564-1712</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1735-207X |
| ispartof | Journal of the Iranian Chemical Society, 2022-04, Vol.19 (4), p.1413-1423 |
| issn | 1735-207X 1735-2428 |
| language | eng |
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| source | SpringerNature Journals |
| subjects | Analytical Chemistry Antiinfectives and antibacterials Bacteria Biochemistry Chemical synthesis Chemistry Chemistry and Materials Science Docking E coli Fungicides Inorganic Chemistry Organic Chemistry Original Paper Oxazole Physical Chemistry Pyrazole |
| title | Thiochromene candidates: design, synthesis, antimicrobial potential and in silico docking study |
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