Kaolin-catalysed one-pot synthesis of thiophene containing aminonaphthols under solvent-free condition and their in vitro anticancer and antioxidant activity
An efficient and eco-friendly synthetic protocol via a one-pot three-component reaction to yield thiophene containing aminonaphthols (Betti bases) is reported. Kaolin was used as a heterogeneous catalyst and a series of Betti bases were synthesized under solvent-free condition. The synthesized deriv...
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| Veröffentlicht in: | Research on chemical intermediates 2021-10, Vol.47 (10), p.4067-4082 |
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| container_title | Research on chemical intermediates |
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| creator | Yellapurkar, Ishita Shaikh, Sarfaraz Pavale, Ganesh Bhabal, Sonal Ramana, M. M. V. |
| description | An efficient and eco-friendly synthetic protocol via a one-pot three-component reaction to yield thiophene containing aminonaphthols (Betti bases) is reported. Kaolin was used as a heterogeneous catalyst and a series of Betti bases were synthesized under solvent-free condition. The synthesized derivatives were characterized by various techniques, viz. FTIR,
1
H-NMR,
13
C-NMR, mass spectrometry and elemental analysis. The synthesized compounds were screened for in vitro anticancer and antioxidant activities. Compounds
4d
,
4i
,
4j
exhibited excellent anticancer activity (GI
50
|
| doi_str_mv | 10.1007/s11164-021-04516-5 |
| format | Article |
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1
H-NMR,
13
C-NMR, mass spectrometry and elemental analysis. The synthesized compounds were screened for in vitro anticancer and antioxidant activities. Compounds
4d
,
4i
,
4j
exhibited excellent anticancer activity (GI
50
< 10 µg/ml) against all four cell lines which was comparable with the standard drug doxorubicin. Compound
4d
was found to be the most potent antioxidant against DPPH radical and H
2
O
2
. The reusability studies demonstrated the retention in catalytic activity for up to six cycles. The current synthetic methodology offers several advantages such as excellent yields, mild reaction conditions, short reaction span, ease of work-up, broad substrate scope and reusability.
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1
H-NMR,
13
C-NMR, mass spectrometry and elemental analysis. The synthesized compounds were screened for in vitro anticancer and antioxidant activities. Compounds
4d
,
4i
,
4j
exhibited excellent anticancer activity (GI
50
< 10 µg/ml) against all four cell lines which was comparable with the standard drug doxorubicin. Compound
4d
was found to be the most potent antioxidant against DPPH radical and H
2
O
2
. The reusability studies demonstrated the retention in catalytic activity for up to six cycles. The current synthetic methodology offers several advantages such as excellent yields, mild reaction conditions, short reaction span, ease of work-up, broad substrate scope and reusability.
Graphic abstract</description><subject>Anticancer properties</subject><subject>Antioxidants</subject><subject>Cancer</subject><subject>Catalysis</subject><subject>Catalytic activity</subject><subject>Chemical analysis</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Doxorubicin</subject><subject>Hydrogen peroxide</subject><subject>Inorganic Chemistry</subject><subject>Kaolin</subject><subject>Mass spectrometry</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Physical Chemistry</subject><subject>Solvents</subject><subject>Substrates</subject><issn>0922-6168</issn><issn>1568-5675</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNp9kcFuGyEURVHVSnXd_kBWSF2TwoyB8TKymrRqpGzSNXrDQIZo_JgAjuKPyb8GeyJ1VzZXPM69T-gSciH4peBc_8hCCLVhvBGMb6RQTH4gKyFVx6TS8iNZ8W3TMCVU95l8yfmRcyG7jq_I6x-IU0BmocB0zG6gER2bY6H5iGV0OWQaPS1jiPPo0FEbsUDAgA8U9gEjwjyWMU6ZHnBwieY4PTsszCd3hodQQkQKONQQFxINSJ9DSbGOSrCAtppOr6drfAlDVQq2hAodv5JPHqbsvr3rmvy9_nm_-8Vu725-765umW3FtjDhhVadbreN7a3q61et1pZvFEDfcd9o3-re-0G0WncOeKs0wFZJBb11EjbtmnxfcucUnw4uF_MYDwnrStNIrc5HV6pZKJtizsl5M6ewh3Q0gptTDWapwdQazLkGI6upXUy5wvjg0r_o_7jeAI8Rj6c</recordid><startdate>20211001</startdate><enddate>20211001</enddate><creator>Yellapurkar, Ishita</creator><creator>Shaikh, Sarfaraz</creator><creator>Pavale, Ganesh</creator><creator>Bhabal, Sonal</creator><creator>Ramana, M. M. V.</creator><general>Springer Netherlands</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-2220-8019</orcidid></search><sort><creationdate>20211001</creationdate><title>Kaolin-catalysed one-pot synthesis of thiophene containing aminonaphthols under solvent-free condition and their in vitro anticancer and antioxidant activity</title><author>Yellapurkar, Ishita ; Shaikh, Sarfaraz ; Pavale, Ganesh ; Bhabal, Sonal ; Ramana, M. M. V.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c319t-1f17687392cbc6b922c77c046aab80f27f37bffd13778ea0367aa9656abce5a43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Anticancer properties</topic><topic>Antioxidants</topic><topic>Cancer</topic><topic>Catalysis</topic><topic>Catalytic activity</topic><topic>Chemical analysis</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Doxorubicin</topic><topic>Hydrogen peroxide</topic><topic>Inorganic Chemistry</topic><topic>Kaolin</topic><topic>Mass spectrometry</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Physical Chemistry</topic><topic>Solvents</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yellapurkar, Ishita</creatorcontrib><creatorcontrib>Shaikh, Sarfaraz</creatorcontrib><creatorcontrib>Pavale, Ganesh</creatorcontrib><creatorcontrib>Bhabal, Sonal</creatorcontrib><creatorcontrib>Ramana, M. M. V.</creatorcontrib><collection>CrossRef</collection><jtitle>Research on chemical intermediates</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yellapurkar, Ishita</au><au>Shaikh, Sarfaraz</au><au>Pavale, Ganesh</au><au>Bhabal, Sonal</au><au>Ramana, M. M. V.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Kaolin-catalysed one-pot synthesis of thiophene containing aminonaphthols under solvent-free condition and their in vitro anticancer and antioxidant activity</atitle><jtitle>Research on chemical intermediates</jtitle><stitle>Res Chem Intermed</stitle><date>2021-10-01</date><risdate>2021</risdate><volume>47</volume><issue>10</issue><spage>4067</spage><epage>4082</epage><pages>4067-4082</pages><issn>0922-6168</issn><eissn>1568-5675</eissn><abstract>An efficient and eco-friendly synthetic protocol via a one-pot three-component reaction to yield thiophene containing aminonaphthols (Betti bases) is reported. Kaolin was used as a heterogeneous catalyst and a series of Betti bases were synthesized under solvent-free condition. The synthesized derivatives were characterized by various techniques, viz. FTIR,
1
H-NMR,
13
C-NMR, mass spectrometry and elemental analysis. The synthesized compounds were screened for in vitro anticancer and antioxidant activities. Compounds
4d
,
4i
,
4j
exhibited excellent anticancer activity (GI
50
< 10 µg/ml) against all four cell lines which was comparable with the standard drug doxorubicin. Compound
4d
was found to be the most potent antioxidant against DPPH radical and H
2
O
2
. The reusability studies demonstrated the retention in catalytic activity for up to six cycles. The current synthetic methodology offers several advantages such as excellent yields, mild reaction conditions, short reaction span, ease of work-up, broad substrate scope and reusability.
Graphic abstract</abstract><cop>Dordrecht</cop><pub>Springer Netherlands</pub><doi>10.1007/s11164-021-04516-5</doi><tpages>16</tpages><orcidid>https://orcid.org/0000-0002-2220-8019</orcidid></addata></record> |
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| issn | 0922-6168 1568-5675 |
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| subjects | Anticancer properties Antioxidants Cancer Catalysis Catalytic activity Chemical analysis Chemical synthesis Chemistry Chemistry and Materials Science Doxorubicin Hydrogen peroxide Inorganic Chemistry Kaolin Mass spectrometry NMR Nuclear magnetic resonance Physical Chemistry Solvents Substrates |
| title | Kaolin-catalysed one-pot synthesis of thiophene containing aminonaphthols under solvent-free condition and their in vitro anticancer and antioxidant activity |
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