Synthesis and structural elucidation of 1,2-naphthoquinone derivatives, Schiff base complexes and ternary complexes with 8-hydroxyquinoline: comparative studies of their antimicrobial, anti-inflammatory and anti-diabetic activities
Herein, a new derivative of 1,2-naphthoquinone with semicarbazide and its Schiff base complexes and ternary complexes have been synthesized with some transition metals such as Ni(II), Co(II) and Zn(II) by using the conventional reflux method and 8-hydroxyquinoline (8-HQ) as a secondary ligand for te...
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| Veröffentlicht in: | Transition metal chemistry (Weinheim) 2023-12, Vol.48 (6), p.389-400 |
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| creator | Seema Sharma, Shobhana Yadav, Poonam Kumari, Suman Ranka, Mamta |
| description | Herein, a new derivative of 1,2-naphthoquinone with semicarbazide and its Schiff base complexes and ternary complexes have been synthesized with some transition metals such as Ni(II), Co(II) and Zn(II) by using the conventional reflux method and 8-hydroxyquinoline (8-HQ) as a secondary ligand for ternary complexes. All the compounds were characterized using elemental analysis, molar conductance, melting point, Powder XRD, magnetic moment measurement and various spectral techniques such as FTIR,
13
C NMR,
1
H NMR, and Mass Spectra. The specific peak of the enolic proton in
1
H NMR spectra of the tridentate ligand (L) explained the amido-iminol tautomerism in semicarbazone. In addition, powder XRD analysis and TGA confirmed the crystalline nature and the thermal study of metal chelates, respectively
.
In vitro
,
all the compounds were screened for antimicrobial (against bacterial strains:
S. aureus
and
E. coli
; Fungal strain:
A. niger
), anti-diabetic and anti-inflammatory activity with their obtained IC
50
values and compared with Acarbose and Aspirin standard drugs. Bioactivities of azomethine containing free ligand (L), their Schiff base complexes and ternary metal chelates were compared to each other. Free Schiff base (L) was found most potent for all selective bioactivities compared to their all-metal complexes, except Ni (II) Schiff base complex showed excellent activity against
C. albicans. |
| doi_str_mv | 10.1007/s11243-023-00551-w |
| format | Article |
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13
C NMR,
1
H NMR, and Mass Spectra. The specific peak of the enolic proton in
1
H NMR spectra of the tridentate ligand (L) explained the amido-iminol tautomerism in semicarbazone. In addition, powder XRD analysis and TGA confirmed the crystalline nature and the thermal study of metal chelates, respectively
.
In vitro
,
all the compounds were screened for antimicrobial (against bacterial strains:
S. aureus
and
E. coli
; Fungal strain:
A. niger
), anti-diabetic and anti-inflammatory activity with their obtained IC
50
values and compared with Acarbose and Aspirin standard drugs. Bioactivities of azomethine containing free ligand (L), their Schiff base complexes and ternary metal chelates were compared to each other. Free Schiff base (L) was found most potent for all selective bioactivities compared to their all-metal complexes, except Ni (II) Schiff base complex showed excellent activity against
C. albicans.</description><identifier>ISSN: 0340-4285</identifier><identifier>EISSN: 1572-901X</identifier><identifier>DOI: 10.1007/s11243-023-00551-w</identifier><language>eng</language><publisher>Cham: Springer International Publishing</publisher><subject>Antidiabetics ; Aspirin ; Biological activity ; Catalysis ; Chelates ; Chemical analysis ; Chemistry ; Chemistry and Materials Science ; Comparative studies ; Coordination compounds ; Diabetes ; E coli ; Hydroxyquinoline ; Imines ; Inorganic Chemistry ; Ligands ; Magnetic moments ; Mass spectra ; Melting points ; NMR ; Nuclear magnetic resonance ; Organometallic Chemistry ; Physical Chemistry ; Protons ; Spectral methods ; Transition metals</subject><ispartof>Transition metal chemistry (Weinheim), 2023-12, Vol.48 (6), p.389-400</ispartof><rights>The Author(s), under exclusive licence to Springer Nature Switzerland AG 2023. Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c319t-97c992537081c8eb12a11a056f09776729c86ade5fddeeee817a49dac8c2a92d3</citedby><cites>FETCH-LOGICAL-c319t-97c992537081c8eb12a11a056f09776729c86ade5fddeeee817a49dac8c2a92d3</cites><orcidid>0000-0001-6678-6104 ; 0000-0002-9975-718X ; 0000-0003-4884-1784 ; 0000-0001-8866-4781 ; 0000-0002-1064-8033</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/s11243-023-00551-w$$EPDF$$P50$$Gspringer$$H</linktopdf><linktohtml>$$Uhttps://link.springer.com/10.1007/s11243-023-00551-w$$EHTML$$P50$$Gspringer$$H</linktohtml><link.rule.ids>314,776,780,27901,27902,41464,42533,51294</link.rule.ids></links><search><creatorcontrib>Seema</creatorcontrib><creatorcontrib>Sharma, Shobhana</creatorcontrib><creatorcontrib>Yadav, Poonam</creatorcontrib><creatorcontrib>Kumari, Suman</creatorcontrib><creatorcontrib>Ranka, Mamta</creatorcontrib><title>Synthesis and structural elucidation of 1,2-naphthoquinone derivatives, Schiff base complexes and ternary complexes with 8-hydroxyquinoline: comparative studies of their antimicrobial, anti-inflammatory and anti-diabetic activities</title><title>Transition metal chemistry (Weinheim)</title><addtitle>Transit Met Chem</addtitle><description>Herein, a new derivative of 1,2-naphthoquinone with semicarbazide and its Schiff base complexes and ternary complexes have been synthesized with some transition metals such as Ni(II), Co(II) and Zn(II) by using the conventional reflux method and 8-hydroxyquinoline (8-HQ) as a secondary ligand for ternary complexes. All the compounds were characterized using elemental analysis, molar conductance, melting point, Powder XRD, magnetic moment measurement and various spectral techniques such as FTIR,
13
C NMR,
1
H NMR, and Mass Spectra. The specific peak of the enolic proton in
1
H NMR spectra of the tridentate ligand (L) explained the amido-iminol tautomerism in semicarbazone. In addition, powder XRD analysis and TGA confirmed the crystalline nature and the thermal study of metal chelates, respectively
.
In vitro
,
all the compounds were screened for antimicrobial (against bacterial strains:
S. aureus
and
E. coli
; Fungal strain:
A. niger
), anti-diabetic and anti-inflammatory activity with their obtained IC
50
values and compared with Acarbose and Aspirin standard drugs. Bioactivities of azomethine containing free ligand (L), their Schiff base complexes and ternary metal chelates were compared to each other. Free Schiff base (L) was found most potent for all selective bioactivities compared to their all-metal complexes, except Ni (II) Schiff base complex showed excellent activity against
C. albicans.</description><subject>Antidiabetics</subject><subject>Aspirin</subject><subject>Biological activity</subject><subject>Catalysis</subject><subject>Chelates</subject><subject>Chemical analysis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Comparative studies</subject><subject>Coordination compounds</subject><subject>Diabetes</subject><subject>E coli</subject><subject>Hydroxyquinoline</subject><subject>Imines</subject><subject>Inorganic Chemistry</subject><subject>Ligands</subject><subject>Magnetic moments</subject><subject>Mass spectra</subject><subject>Melting points</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Organometallic Chemistry</subject><subject>Physical Chemistry</subject><subject>Protons</subject><subject>Spectral methods</subject><subject>Transition metals</subject><issn>0340-4285</issn><issn>1572-901X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNp9kctq3DAUhkVpoNO0L9CVoNtRK8n2yOquhN4g0EUS6E6ckeRawZankpzJPHFeoyd2oFlVIIQO__nO5SfkneAfBOfqYxZC1hXjEi9vGsGOL8hGNEoyzcWvl2TDq5qzWrbNK_I651uOKqnqDXm4OsXS-xwyhehoLmm2ZU4wUD_MNjgoYYp06qjYShbh0Jd--jOHOEVPnU_hDgV3Pm_ple1D19E9ZE_tNB4Gf-9XZvEpQjo9ix5D6WnL-pNL0_1pwQ0h-k-LBNKCxFZmF1CMtbHBkJBVwhhsmvYBhu3yZSF2A4wjlAkLPBZboi7A3pdgKVhEhYKYN-SsgyH7t0_vObn5-uX64ju7_Pntx8XnS2YroQvTymotm0rxVtjW74UEIYA3u45rpXZKatvuwPmmc87jaYWCWjuwrZWgpavOyfuVe0i4J5-LuZ1mnH_IRratqNCbnUCVXFU4Tc7Jd-aQwohLMoKbR0PNaqhBQ81iqDliUrUmZRTH3z79Q_8n6y8N2awm</recordid><startdate>20231201</startdate><enddate>20231201</enddate><creator>Seema</creator><creator>Sharma, Shobhana</creator><creator>Yadav, Poonam</creator><creator>Kumari, Suman</creator><creator>Ranka, Mamta</creator><general>Springer International Publishing</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><orcidid>https://orcid.org/0000-0001-6678-6104</orcidid><orcidid>https://orcid.org/0000-0002-9975-718X</orcidid><orcidid>https://orcid.org/0000-0003-4884-1784</orcidid><orcidid>https://orcid.org/0000-0001-8866-4781</orcidid><orcidid>https://orcid.org/0000-0002-1064-8033</orcidid></search><sort><creationdate>20231201</creationdate><title>Synthesis and structural elucidation of 1,2-naphthoquinone derivatives, Schiff base complexes and ternary complexes with 8-hydroxyquinoline: comparative studies of their antimicrobial, anti-inflammatory and anti-diabetic activities</title><author>Seema ; Sharma, Shobhana ; Yadav, Poonam ; Kumari, Suman ; Ranka, Mamta</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c319t-97c992537081c8eb12a11a056f09776729c86ade5fddeeee817a49dac8c2a92d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Antidiabetics</topic><topic>Aspirin</topic><topic>Biological activity</topic><topic>Catalysis</topic><topic>Chelates</topic><topic>Chemical analysis</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Comparative studies</topic><topic>Coordination compounds</topic><topic>Diabetes</topic><topic>E coli</topic><topic>Hydroxyquinoline</topic><topic>Imines</topic><topic>Inorganic Chemistry</topic><topic>Ligands</topic><topic>Magnetic moments</topic><topic>Mass spectra</topic><topic>Melting points</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Organometallic Chemistry</topic><topic>Physical Chemistry</topic><topic>Protons</topic><topic>Spectral methods</topic><topic>Transition metals</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Seema</creatorcontrib><creatorcontrib>Sharma, Shobhana</creatorcontrib><creatorcontrib>Yadav, Poonam</creatorcontrib><creatorcontrib>Kumari, Suman</creatorcontrib><creatorcontrib>Ranka, Mamta</creatorcontrib><collection>CrossRef</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Transition metal chemistry (Weinheim)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Seema</au><au>Sharma, Shobhana</au><au>Yadav, Poonam</au><au>Kumari, Suman</au><au>Ranka, Mamta</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and structural elucidation of 1,2-naphthoquinone derivatives, Schiff base complexes and ternary complexes with 8-hydroxyquinoline: comparative studies of their antimicrobial, anti-inflammatory and anti-diabetic activities</atitle><jtitle>Transition metal chemistry (Weinheim)</jtitle><stitle>Transit Met Chem</stitle><date>2023-12-01</date><risdate>2023</risdate><volume>48</volume><issue>6</issue><spage>389</spage><epage>400</epage><pages>389-400</pages><issn>0340-4285</issn><eissn>1572-901X</eissn><abstract>Herein, a new derivative of 1,2-naphthoquinone with semicarbazide and its Schiff base complexes and ternary complexes have been synthesized with some transition metals such as Ni(II), Co(II) and Zn(II) by using the conventional reflux method and 8-hydroxyquinoline (8-HQ) as a secondary ligand for ternary complexes. All the compounds were characterized using elemental analysis, molar conductance, melting point, Powder XRD, magnetic moment measurement and various spectral techniques such as FTIR,
13
C NMR,
1
H NMR, and Mass Spectra. The specific peak of the enolic proton in
1
H NMR spectra of the tridentate ligand (L) explained the amido-iminol tautomerism in semicarbazone. In addition, powder XRD analysis and TGA confirmed the crystalline nature and the thermal study of metal chelates, respectively
.
In vitro
,
all the compounds were screened for antimicrobial (against bacterial strains:
S. aureus
and
E. coli
; Fungal strain:
A. niger
), anti-diabetic and anti-inflammatory activity with their obtained IC
50
values and compared with Acarbose and Aspirin standard drugs. Bioactivities of azomethine containing free ligand (L), their Schiff base complexes and ternary metal chelates were compared to each other. Free Schiff base (L) was found most potent for all selective bioactivities compared to their all-metal complexes, except Ni (II) Schiff base complex showed excellent activity against
C. albicans.</abstract><cop>Cham</cop><pub>Springer International Publishing</pub><doi>10.1007/s11243-023-00551-w</doi><tpages>12</tpages><orcidid>https://orcid.org/0000-0001-6678-6104</orcidid><orcidid>https://orcid.org/0000-0002-9975-718X</orcidid><orcidid>https://orcid.org/0000-0003-4884-1784</orcidid><orcidid>https://orcid.org/0000-0001-8866-4781</orcidid><orcidid>https://orcid.org/0000-0002-1064-8033</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0340-4285 |
| ispartof | Transition metal chemistry (Weinheim), 2023-12, Vol.48 (6), p.389-400 |
| issn | 0340-4285 1572-901X |
| language | eng |
| recordid | cdi_proquest_journals_2881355161 |
| source | Springer Nature - Complete Springer Journals |
| subjects | Antidiabetics Aspirin Biological activity Catalysis Chelates Chemical analysis Chemistry Chemistry and Materials Science Comparative studies Coordination compounds Diabetes E coli Hydroxyquinoline Imines Inorganic Chemistry Ligands Magnetic moments Mass spectra Melting points NMR Nuclear magnetic resonance Organometallic Chemistry Physical Chemistry Protons Spectral methods Transition metals |
| title | Synthesis and structural elucidation of 1,2-naphthoquinone derivatives, Schiff base complexes and ternary complexes with 8-hydroxyquinoline: comparative studies of their antimicrobial, anti-inflammatory and anti-diabetic activities |
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