AgNO3 mediated C-N bond forming reaction: synthesis of 3-substituted benzothiazines as potential COX inhibitors

Rambabu, D., Murthy, P. V. N. S., Prasad, K. R. S., Kandale, Ajit, Deora, Girdhar Singh, Rao, M. V. Basaveswara and Pal, Manojit (2012) AgNO3 mediated C-N bond forming reaction: synthesis of 3-substituted benzothiazines as potential COX inhibitors. Tetrahedron Letters, 53 48: 6577-6583. doi:10.1016/j.tetlet.2012.09.102


Author Rambabu, D.
Murthy, P. V. N. S.
Prasad, K. R. S.
Kandale, Ajit
Deora, Girdhar Singh
Rao, M. V. Basaveswara
Pal, Manojit
Title AgNO3 mediated C-N bond forming reaction: synthesis of 3-substituted benzothiazines as potential COX inhibitors
Journal name Tetrahedron Letters   Check publisher's open access policy
ISSN 0040-4039
1873-3581
Publication date 2012-11
Sub-type Article (original research)
DOI 10.1016/j.tetlet.2012.09.102
Open Access Status
Volume 53
Issue 48
Start page 6577
End page 6583
Total pages 7
Place of publication Oxford United Kingdom
Publisher Pergamon Press
Language eng
Formatted abstract
AgNO3 facilitated the intramolecular ring closure of o-(1-alkynyl)benzenesulfonamides via a regioselective C–N bond forming reaction leading to the formation of 3-substituted benzothiazine derivatives. A number of compounds were prepared in good yields by using this inexpensive and safe methodology. All the compounds synthesized were evaluated for their cyclooxygenase (COX) inhibiting properties in vitro. A number of compounds that do not contain an enolic hydroxyl group showed selectivities toward COX-2 over COX-1 inhibition. This was further supported by the predictive binding mode of two compounds with COX-1 and -2 proteins through molecular docking studies.
Keyword Benzothiazine
Benzenesulfonamides
AgNO3
Cox
Docking
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Non-UQ

Document type: Journal Article
Sub-type: Article (original research)
Collection: School of Pharmacy Publications
 
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