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Palladium acetate-catalysed one-pot green synthesis of bis α-aminophosphonates
A simple and effective green method has been developed for the synthesis of a series of novel bis α -aminophosphonate derivatives ( 4a–j) by the reaction of 1,4-diaminonaphthalene, various aryl/heteroaryl aldehydes and dialkyl phosphites under neat and microwave irradiation conditions using palladiu...
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| Published in: | Research on chemical intermediates 2019-03, Vol.45 (3), p.1401-1420 |
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| Main Authors: | , , , , , , , |
| Format: | Article |
| Language: | English |
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| container_end_page | 1420 |
| container_issue | 3 |
| container_start_page | 1401 |
| container_title | Research on chemical intermediates |
| container_volume | 45 |
| creator | Sadik, Shaik Mahammad Santhisudha, Sarva Mohan, Gundluru Reddy, Nadiveedhi Maheshwara Lakshmi, Poola Sree Rajasekhar, Allagadda Rao, Chippada Appa Reddy, Cirandur Suresh |
| description | A simple and effective green method has been developed for the synthesis of a series of novel bis
α
-aminophosphonate derivatives (
4a–j)
by the reaction of 1,4-diaminonaphthalene, various aryl/heteroaryl aldehydes and dialkyl phosphites under neat and microwave irradiation conditions using palladium acetate as catalyst. The products are characterized by elemental analysis, IR,
1
H,
13
C,
31
P-NMR and mass spectra and their antioxidant activities are evaluated by DPPH, NO and H
2
O
2
methods and molecular docking studies. The compounds
4d
and
4h
exhibited the highest radical scavenging activity in the DPPH method, while compounds
4a
,
4e
and
4f
showed good NO scavenging activity. The compound
4g
showed remarkably higher H
2
O
2
scavenging activity than even the standard ascorbic acid, and compound
4h
has stronger inhibiting activity on DNA gyrase enzyme. |
| doi_str_mv | 10.1007/s11164-018-3685-5 |
| format | article |
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α
-aminophosphonate derivatives (
4a–j)
by the reaction of 1,4-diaminonaphthalene, various aryl/heteroaryl aldehydes and dialkyl phosphites under neat and microwave irradiation conditions using palladium acetate as catalyst. The products are characterized by elemental analysis, IR,
1
H,
13
C,
31
P-NMR and mass spectra and their antioxidant activities are evaluated by DPPH, NO and H
2
O
2
methods and molecular docking studies. The compounds
4d
and
4h
exhibited the highest radical scavenging activity in the DPPH method, while compounds
4a
,
4e
and
4f
showed good NO scavenging activity. The compound
4g
showed remarkably higher H
2
O
2
scavenging activity than even the standard ascorbic acid, and compound
4h
has stronger inhibiting activity on DNA gyrase enzyme.</description><identifier>ISSN: 0922-6168</identifier><identifier>EISSN: 1568-5675</identifier><identifier>DOI: 10.1007/s11164-018-3685-5</identifier><language>eng</language><publisher>Dordrecht: Springer Netherlands</publisher><subject>Aldehydes ; Antioxidants ; Aromatic compounds ; Ascorbic acid ; Catalysis ; Chemical analysis ; Chemical synthesis ; Chemistry ; Chemistry and Materials Science ; Deoxyribonucleic acid ; DNA ; Hydrogen peroxide ; Infrared analysis ; Inorganic Chemistry ; Inorganic salts ; Mass spectra ; Molecular docking ; NMR ; Nuclear magnetic resonance ; Palladium ; Physical Chemistry ; Scavenging</subject><ispartof>Research on chemical intermediates, 2019-03, Vol.45 (3), p.1401-1420</ispartof><rights>Springer Nature B.V. 2018</rights><rights>Copyright Springer Nature B.V. 2019</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c2315-665913e96b3485d26c0f9a665dca748bd6b3ae62f6c8548cafbeb06bf902dde53</citedby><cites>FETCH-LOGICAL-c2315-665913e96b3485d26c0f9a665dca748bd6b3ae62f6c8548cafbeb06bf902dde53</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Sadik, Shaik Mahammad</creatorcontrib><creatorcontrib>Santhisudha, Sarva</creatorcontrib><creatorcontrib>Mohan, Gundluru</creatorcontrib><creatorcontrib>Reddy, Nadiveedhi Maheshwara</creatorcontrib><creatorcontrib>Lakshmi, Poola Sree</creatorcontrib><creatorcontrib>Rajasekhar, Allagadda</creatorcontrib><creatorcontrib>Rao, Chippada Appa</creatorcontrib><creatorcontrib>Reddy, Cirandur Suresh</creatorcontrib><title>Palladium acetate-catalysed one-pot green synthesis of bis α-aminophosphonates</title><title>Research on chemical intermediates</title><addtitle>Res Chem Intermed</addtitle><description>A simple and effective green method has been developed for the synthesis of a series of novel bis
α
-aminophosphonate derivatives (
4a–j)
by the reaction of 1,4-diaminonaphthalene, various aryl/heteroaryl aldehydes and dialkyl phosphites under neat and microwave irradiation conditions using palladium acetate as catalyst. The products are characterized by elemental analysis, IR,
1
H,
13
C,
31
P-NMR and mass spectra and their antioxidant activities are evaluated by DPPH, NO and H
2
O
2
methods and molecular docking studies. The compounds
4d
and
4h
exhibited the highest radical scavenging activity in the DPPH method, while compounds
4a
,
4e
and
4f
showed good NO scavenging activity. The compound
4g
showed remarkably higher H
2
O
2
scavenging activity than even the standard ascorbic acid, and compound
4h
has stronger inhibiting activity on DNA gyrase enzyme.</description><subject>Aldehydes</subject><subject>Antioxidants</subject><subject>Aromatic compounds</subject><subject>Ascorbic acid</subject><subject>Catalysis</subject><subject>Chemical analysis</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Deoxyribonucleic acid</subject><subject>DNA</subject><subject>Hydrogen peroxide</subject><subject>Infrared analysis</subject><subject>Inorganic Chemistry</subject><subject>Inorganic salts</subject><subject>Mass spectra</subject><subject>Molecular docking</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Palladium</subject><subject>Physical Chemistry</subject><subject>Scavenging</subject><issn>0922-6168</issn><issn>1568-5675</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp1kM1KAzEUhYMoWKsP4G7AdTQ_k0xmKUWtUKgLXYdMctNOmU7GZLroY_kiPpMpI7hycTlw7znnwofQLSX3lJDqIVFKZYkJVZhLJbA4QzMqpMJCVuIczUjNGJZUqkt0ldKOECqUIjO0fjNdZ1x72BfGwmhGwNaMpjsmcEXoAQ9hLDYRoC_SsR-3kNpUBF80Wb6_sNm3fRi2IeXpczhdowtvugQ3vzpHH89P74slXq1fXhePK2wZpwJLKWrKoZYNL5VwTFria5O3zpqqVI3LBwOSeWmVKJU1voGGyMbXhDkHgs_R3dQ7xPB5gDTqXTjEPr_UjCrOREU4yy46uWwMKUXweojt3sSjpkSfuOmJm87c9ImbPjWzKZOyt99A_Gv-P_QD6Wpxrw</recordid><startdate>20190315</startdate><enddate>20190315</enddate><creator>Sadik, Shaik Mahammad</creator><creator>Santhisudha, Sarva</creator><creator>Mohan, Gundluru</creator><creator>Reddy, Nadiveedhi Maheshwara</creator><creator>Lakshmi, Poola Sree</creator><creator>Rajasekhar, Allagadda</creator><creator>Rao, Chippada Appa</creator><creator>Reddy, Cirandur Suresh</creator><general>Springer Netherlands</general><general>Springer Nature B.V</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20190315</creationdate><title>Palladium acetate-catalysed one-pot green synthesis of bis α-aminophosphonates</title><author>Sadik, Shaik Mahammad ; Santhisudha, Sarva ; Mohan, Gundluru ; Reddy, Nadiveedhi Maheshwara ; Lakshmi, Poola Sree ; Rajasekhar, Allagadda ; Rao, Chippada Appa ; Reddy, Cirandur Suresh</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2315-665913e96b3485d26c0f9a665dca748bd6b3ae62f6c8548cafbeb06bf902dde53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Aldehydes</topic><topic>Antioxidants</topic><topic>Aromatic compounds</topic><topic>Ascorbic acid</topic><topic>Catalysis</topic><topic>Chemical analysis</topic><topic>Chemical synthesis</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Deoxyribonucleic acid</topic><topic>DNA</topic><topic>Hydrogen peroxide</topic><topic>Infrared analysis</topic><topic>Inorganic Chemistry</topic><topic>Inorganic salts</topic><topic>Mass spectra</topic><topic>Molecular docking</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Palladium</topic><topic>Physical Chemistry</topic><topic>Scavenging</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sadik, Shaik Mahammad</creatorcontrib><creatorcontrib>Santhisudha, Sarva</creatorcontrib><creatorcontrib>Mohan, Gundluru</creatorcontrib><creatorcontrib>Reddy, Nadiveedhi Maheshwara</creatorcontrib><creatorcontrib>Lakshmi, Poola Sree</creatorcontrib><creatorcontrib>Rajasekhar, Allagadda</creatorcontrib><creatorcontrib>Rao, Chippada Appa</creatorcontrib><creatorcontrib>Reddy, Cirandur Suresh</creatorcontrib><collection>CrossRef</collection><jtitle>Research on chemical intermediates</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sadik, Shaik Mahammad</au><au>Santhisudha, Sarva</au><au>Mohan, Gundluru</au><au>Reddy, Nadiveedhi Maheshwara</au><au>Lakshmi, Poola Sree</au><au>Rajasekhar, Allagadda</au><au>Rao, Chippada Appa</au><au>Reddy, Cirandur Suresh</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Palladium acetate-catalysed one-pot green synthesis of bis α-aminophosphonates</atitle><jtitle>Research on chemical intermediates</jtitle><stitle>Res Chem Intermed</stitle><date>2019-03-15</date><risdate>2019</risdate><volume>45</volume><issue>3</issue><spage>1401</spage><epage>1420</epage><pages>1401-1420</pages><issn>0922-6168</issn><eissn>1568-5675</eissn><abstract>A simple and effective green method has been developed for the synthesis of a series of novel bis
α
-aminophosphonate derivatives (
4a–j)
by the reaction of 1,4-diaminonaphthalene, various aryl/heteroaryl aldehydes and dialkyl phosphites under neat and microwave irradiation conditions using palladium acetate as catalyst. The products are characterized by elemental analysis, IR,
1
H,
13
C,
31
P-NMR and mass spectra and their antioxidant activities are evaluated by DPPH, NO and H
2
O
2
methods and molecular docking studies. The compounds
4d
and
4h
exhibited the highest radical scavenging activity in the DPPH method, while compounds
4a
,
4e
and
4f
showed good NO scavenging activity. The compound
4g
showed remarkably higher H
2
O
2
scavenging activity than even the standard ascorbic acid, and compound
4h
has stronger inhibiting activity on DNA gyrase enzyme.</abstract><cop>Dordrecht</cop><pub>Springer Netherlands</pub><doi>10.1007/s11164-018-3685-5</doi><tpages>20</tpages></addata></record> |
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| ispartof | Research on chemical intermediates, 2019-03, Vol.45 (3), p.1401-1420 |
| issn | 0922-6168 1568-5675 |
| language | eng |
| recordid | cdi_proquest_journals_2183257032 |
| source | Springer Link |
| subjects | Aldehydes Antioxidants Aromatic compounds Ascorbic acid Catalysis Chemical analysis Chemical synthesis Chemistry Chemistry and Materials Science Deoxyribonucleic acid DNA Hydrogen peroxide Infrared analysis Inorganic Chemistry Inorganic salts Mass spectra Molecular docking NMR Nuclear magnetic resonance Palladium Physical Chemistry Scavenging |
| title | Palladium acetate-catalysed one-pot green synthesis of bis α-aminophosphonates |
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