Synthesis of new 3-(2-mercapto-4-oxo-4H-quinazolin-3-yl)-benzenesulfonamides with strong inhibition properties against the tumor associated carbonic anhydrases IX and XII
We report a series of novel metanilamide-based derivatives 3a–q bearing the 2-mercapto-4-oxo-4H-quinazolin-3-yl moiety as tail. All compounds were synthesized by means of straightforward condensation procedures and were investigated in vitro for their inhibition potency against the human (h) carboni...
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| Format: | Article |
| Language: | English English English |
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Elsevier Ltd
2017
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| Online Access: | http://irep.iium.edu.my/57250/ http://irep.iium.edu.my/57250/ http://irep.iium.edu.my/57250/ http://irep.iium.edu.my/57250/3/57250_Synthesis%20of%20new%203-%282-mercapto_WOS.pdf http://irep.iium.edu.my/57250/19/57250_Synthesis%20of%20new%203-%282-mercapto-4-oxo-4H-quinazolin-3-yl%29.pdf http://irep.iium.edu.my/57250/25/57250_Synthesis%20of%20new%203-%282-mercapto-4-oxo-4H-quinazolin-3-yl%29-benzenesulfonamides_SCOPUS.pdf |
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iium-572502018-06-21T00:37:56Z http://irep.iium.edu.my/57250/ Synthesis of new 3-(2-mercapto-4-oxo-4H-quinazolin-3-yl)-benzenesulfonamides with strong inhibition properties against the tumor associated carbonic anhydrases IX and XII Bozdag, Murat Alafeefy, Ahmed Mahmoud Altamimi, Abdul Malik Carta, Fabrizio Supuran,, Claudiu T. Vullo, Daniela QD Chemistry We report a series of novel metanilamide-based derivatives 3a–q bearing the 2-mercapto-4-oxo-4H-quinazolin-3-yl moiety as tail. All compounds were synthesized by means of straightforward condensation procedures and were investigated in vitro for their inhibition potency against the human (h) carbonic anhydrase (CA; EC 4.2.1.1.1) isoforms I, II, IX and XII. Among all compounds tested the 6-iodo 3g and the 7-fluoro 3i derivatives were the most potent inhibitors against the tumor associated CA IX and XII isoform (KIs 1.5 and 2.7 nM respectively for the hCA IX and KIs 0.57 and 1.9 nM respectively for the hCA XII). The kinetic data reported here strongly support compounds of this type for their future development as radiotracers in tumor pathologies which are strictly dependent on the enzymatic activity of the hCA IX and XII isoforms. Elsevier Ltd 2017-05-15 Article PeerReviewed application/pdf en http://irep.iium.edu.my/57250/3/57250_Synthesis%20of%20new%203-%282-mercapto_WOS.pdf application/pdf en http://irep.iium.edu.my/57250/19/57250_Synthesis%20of%20new%203-%282-mercapto-4-oxo-4H-quinazolin-3-yl%29.pdf application/pdf en http://irep.iium.edu.my/57250/25/57250_Synthesis%20of%20new%203-%282-mercapto-4-oxo-4H-quinazolin-3-yl%29-benzenesulfonamides_SCOPUS.pdf Bozdag, Murat and Alafeefy, Ahmed Mahmoud and Altamimi, Abdul Malik and Carta, Fabrizio and Supuran,, Claudiu T. and Vullo, Daniela (2017) Synthesis of new 3-(2-mercapto-4-oxo-4H-quinazolin-3-yl)-benzenesulfonamides with strong inhibition properties against the tumor associated carbonic anhydrases IX and XII. Bioorganic & Medicinal Chemistry, 25 (10). pp. 2782-2788. ISSN 0968-0896 E-ISSN 1464-3391 http://www.sciencedirect.com/science/article/pii/S0968089617304443 10.1016/j.bmc.2017.03.054 |
| repository_type |
Digital Repository |
| institution_category |
Local University |
| institution |
International Islamic University Malaysia |
| building |
IIUM Repository |
| collection |
Online Access |
| language |
English English English |
| topic |
QD Chemistry |
| spellingShingle |
QD Chemistry Bozdag, Murat Alafeefy, Ahmed Mahmoud Altamimi, Abdul Malik Carta, Fabrizio Supuran,, Claudiu T. Vullo, Daniela Synthesis of new 3-(2-mercapto-4-oxo-4H-quinazolin-3-yl)-benzenesulfonamides with strong inhibition properties against the tumor associated carbonic anhydrases IX and XII |
| description |
We report a series of novel metanilamide-based derivatives 3a–q bearing the 2-mercapto-4-oxo-4H-quinazolin-3-yl moiety as tail. All compounds were synthesized by means of straightforward condensation procedures and were investigated in vitro for their inhibition potency against the human (h) carbonic anhydrase (CA; EC 4.2.1.1.1) isoforms I, II, IX and XII. Among all compounds tested the 6-iodo 3g and the 7-fluoro 3i derivatives were the most potent inhibitors against the tumor associated CA IX and XII isoform (KIs 1.5 and 2.7 nM respectively for the hCA IX and KIs 0.57 and 1.9 nM respectively for the hCA XII).
The kinetic data reported here strongly support compounds of this type for their future development as radiotracers in tumor pathologies which are strictly dependent on the enzymatic activity of the hCA IX and XII isoforms. |
| format |
Article |
| author |
Bozdag, Murat Alafeefy, Ahmed Mahmoud Altamimi, Abdul Malik Carta, Fabrizio Supuran,, Claudiu T. Vullo, Daniela |
| author_facet |
Bozdag, Murat Alafeefy, Ahmed Mahmoud Altamimi, Abdul Malik Carta, Fabrizio Supuran,, Claudiu T. Vullo, Daniela |
| author_sort |
Bozdag, Murat |
| title |
Synthesis of new 3-(2-mercapto-4-oxo-4H-quinazolin-3-yl)-benzenesulfonamides with strong inhibition properties against the tumor associated carbonic anhydrases IX and XII |
| title_short |
Synthesis of new 3-(2-mercapto-4-oxo-4H-quinazolin-3-yl)-benzenesulfonamides with strong inhibition properties against the tumor associated carbonic anhydrases IX and XII |
| title_full |
Synthesis of new 3-(2-mercapto-4-oxo-4H-quinazolin-3-yl)-benzenesulfonamides with strong inhibition properties against the tumor associated carbonic anhydrases IX and XII |
| title_fullStr |
Synthesis of new 3-(2-mercapto-4-oxo-4H-quinazolin-3-yl)-benzenesulfonamides with strong inhibition properties against the tumor associated carbonic anhydrases IX and XII |
| title_full_unstemmed |
Synthesis of new 3-(2-mercapto-4-oxo-4H-quinazolin-3-yl)-benzenesulfonamides with strong inhibition properties against the tumor associated carbonic anhydrases IX and XII |
| title_sort |
synthesis of new 3-(2-mercapto-4-oxo-4h-quinazolin-3-yl)-benzenesulfonamides with strong inhibition properties against the tumor associated carbonic anhydrases ix and xii |
| publisher |
Elsevier Ltd |
| publishDate |
2017 |
| url |
http://irep.iium.edu.my/57250/ http://irep.iium.edu.my/57250/ http://irep.iium.edu.my/57250/ http://irep.iium.edu.my/57250/3/57250_Synthesis%20of%20new%203-%282-mercapto_WOS.pdf http://irep.iium.edu.my/57250/19/57250_Synthesis%20of%20new%203-%282-mercapto-4-oxo-4H-quinazolin-3-yl%29.pdf http://irep.iium.edu.my/57250/25/57250_Synthesis%20of%20new%203-%282-mercapto-4-oxo-4H-quinazolin-3-yl%29-benzenesulfonamides_SCOPUS.pdf |
| first_indexed |
2023-09-18T21:20:54Z |
| last_indexed |
2023-09-18T21:20:54Z |
| _version_ |
1777411874160115712 |