Iodine-mediated one-pot intramolecular decarboxylation domino reaction for accessing functionalised 2-(1,3,4-oxadiazol-2-yl)anilines with carbonic anhydrase inhibitory action
A practical and transition metal-free one-pot domino synthesis of diversified (1,3,4-oxadiazol-2-yl)anilines has been developed employing isatins and hydrazides as the starting materials, in the presence of molecular iodine. The prominent feature of this domino process involves consecutive condensat...
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| Format: | Article |
| Language: | English |
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Taylor & Francis Group
2018-01-01
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| Series: | Journal of Enzyme Inhibition and Medicinal Chemistry |
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| Online Access: | http://dx.doi.org/10.1080/14756366.2018.1443447 |
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| author | Srinivas Angapelly P. V. Sri Ramya Rohini Sodhi Andrea Angeli Krishnan Rangan Narayana Nagesh Claudiu T. Supuran Mohammed Arifuddin |
| author_facet | Srinivas Angapelly P. V. Sri Ramya Rohini Sodhi Andrea Angeli Krishnan Rangan Narayana Nagesh Claudiu T. Supuran Mohammed Arifuddin |
| author_sort | Srinivas Angapelly |
| collection | DOAJ |
| description | A practical and transition metal-free one-pot domino synthesis of diversified (1,3,4-oxadiazol-2-yl)anilines has been developed employing isatins and hydrazides as the starting materials, in the presence of molecular iodine. The prominent feature of this domino process involves consecutive condensation, hydrolytic ring cleavage, and an intramolecular decarboxylation, in a one-pot process that leads to the oxidative formation of a C–O bond. Fluorescence properties of some of the representative molecules obtained in this way were studied. The synthesised 2-(1,3,4-oxadiazolo-2-yl)aniline-benzene sulphonamides (8a–o) were screened for their carbonic anhydrase (CA, EC 4.2.1.1) inhibitory activity. Most of the compounds exhibited low micromolar to nanomolar activity against human (h) isoforms hCA I, hCA II, hCA IV, and XII, with some compounds displaying selective CA inhibitory activity towards hCA II with KIs of 6.4–17.6 nM. |
| first_indexed | 2024-12-20T06:43:55Z |
| format | Article |
| id | doaj.art-187d1c54c3ce4f148a9f77de01eb6bb5 |
| institution | Directory Open Access Journal |
| issn | 1475-6366 1475-6374 |
| language | English |
| last_indexed | 2024-12-20T06:43:55Z |
| publishDate | 2018-01-01 |
| publisher | Taylor & Francis Group |
| record_format | Article |
| series | Journal of Enzyme Inhibition and Medicinal Chemistry |
| spelling | doaj.art-187d1c54c3ce4f148a9f77de01eb6bb52022-12-21T19:49:47ZengTaylor & Francis GroupJournal of Enzyme Inhibition and Medicinal Chemistry1475-63661475-63742018-01-0133161562810.1080/14756366.2018.14434471443447Iodine-mediated one-pot intramolecular decarboxylation domino reaction for accessing functionalised 2-(1,3,4-oxadiazol-2-yl)anilines with carbonic anhydrase inhibitory actionSrinivas Angapelly0P. V. Sri Ramya1Rohini Sodhi2Andrea Angeli3Krishnan Rangan4Narayana Nagesh5Claudiu T. Supuran6Mohammed Arifuddin7National Institute of Pharmaceutical Education and Research (NIPER) – HyderabadNational Institute of Pharmaceutical Education and Research (NIPER) – HyderabadNational Institute of Pharmaceutical Education and Research (NIPER) – HyderabadSezione di Scienze Farmaceutiche e Nutraceutiche, University of FlorenceBirla Institute of Technology & Science, PilaniCenter for Cellular and Molecular Biology (CCMB)Sezione di Scienze Farmaceutiche e Nutraceutiche, University of FlorenceNational Institute of Pharmaceutical Education and Research (NIPER) – HyderabadA practical and transition metal-free one-pot domino synthesis of diversified (1,3,4-oxadiazol-2-yl)anilines has been developed employing isatins and hydrazides as the starting materials, in the presence of molecular iodine. The prominent feature of this domino process involves consecutive condensation, hydrolytic ring cleavage, and an intramolecular decarboxylation, in a one-pot process that leads to the oxidative formation of a C–O bond. Fluorescence properties of some of the representative molecules obtained in this way were studied. The synthesised 2-(1,3,4-oxadiazolo-2-yl)aniline-benzene sulphonamides (8a–o) were screened for their carbonic anhydrase (CA, EC 4.2.1.1) inhibitory activity. Most of the compounds exhibited low micromolar to nanomolar activity against human (h) isoforms hCA I, hCA II, hCA IV, and XII, with some compounds displaying selective CA inhibitory activity towards hCA II with KIs of 6.4–17.6 nM.http://dx.doi.org/10.1080/14756366.2018.1443447Domino synthesis1,3,4-oxadiazolecarbonic anhydrasesulphonamideiodine |
| spellingShingle | Srinivas Angapelly P. V. Sri Ramya Rohini Sodhi Andrea Angeli Krishnan Rangan Narayana Nagesh Claudiu T. Supuran Mohammed Arifuddin Iodine-mediated one-pot intramolecular decarboxylation domino reaction for accessing functionalised 2-(1,3,4-oxadiazol-2-yl)anilines with carbonic anhydrase inhibitory action Journal of Enzyme Inhibition and Medicinal Chemistry Domino synthesis 1,3,4-oxadiazole carbonic anhydrase sulphonamide iodine |
| title | Iodine-mediated one-pot intramolecular decarboxylation domino reaction for accessing functionalised 2-(1,3,4-oxadiazol-2-yl)anilines with carbonic anhydrase inhibitory action |
| title_full | Iodine-mediated one-pot intramolecular decarboxylation domino reaction for accessing functionalised 2-(1,3,4-oxadiazol-2-yl)anilines with carbonic anhydrase inhibitory action |
| title_fullStr | Iodine-mediated one-pot intramolecular decarboxylation domino reaction for accessing functionalised 2-(1,3,4-oxadiazol-2-yl)anilines with carbonic anhydrase inhibitory action |
| title_full_unstemmed | Iodine-mediated one-pot intramolecular decarboxylation domino reaction for accessing functionalised 2-(1,3,4-oxadiazol-2-yl)anilines with carbonic anhydrase inhibitory action |
| title_short | Iodine-mediated one-pot intramolecular decarboxylation domino reaction for accessing functionalised 2-(1,3,4-oxadiazol-2-yl)anilines with carbonic anhydrase inhibitory action |
| title_sort | iodine mediated one pot intramolecular decarboxylation domino reaction for accessing functionalised 2 1 3 4 oxadiazol 2 yl anilines with carbonic anhydrase inhibitory action |
| topic | Domino synthesis 1,3,4-oxadiazole carbonic anhydrase sulphonamide iodine |
| url | http://dx.doi.org/10.1080/14756366.2018.1443447 |
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