Pharmacophoric 2-hydroxyalkyl benzenesulfonamide: A single-step synthesis from benzenesulfonamide via hemiaminal

ortho-Acylation attempt of benzenesulfonamide afforded the corresponding hemiaminal as major product. The in situ reduction of the reaction mixture, reported herein, directly provided 2-hydroxyalkyl benzenesulfonamide, an important pharmacophoric element for designing drug-like scaffolds. Its applic...

Full description

Saved in:
Bibliographic Details
Published in:European journal of medicinal chemistry 2007-04, Vol.42 (4), p.456-462
Main Authors: Singh, Sunil K., Shivaramakrishna, S., Saibaba, V., Rao, K. Srinivas, Ganesh, K. Ravi, Vasudev, R., Kumar, P. Praveen, Babu, J. Moses, Vyas, K., Rao, Y. Koteswar, Iqbal, J.
Format: Article
Language:English
Subjects:
2-Hydroxyalkyl benzenesulfonamide
Aldehydes - chemistry
Alkanes - chemistry
Benzenesulfonamides
Benzisothiazoles
Carbonic Anhydrase Inhibitors - chemistry
Chemistry
Chemistry, Pharmaceutical
Drug Design
Exact sciences and technology
gamma-Aminobutyric Acid
Hemiaminal–carbonyl mixture
Models, Molecular
Molecular Structure
Noncondensed benzenic compounds
Organic chemistry
Oxidation-Reduction
Preparations and properties
Sulfonamides - chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:ortho-Acylation attempt of benzenesulfonamide afforded the corresponding hemiaminal as major product. The in situ reduction of the reaction mixture, reported herein, directly provided 2-hydroxyalkyl benzenesulfonamide, an important pharmacophoric element for designing drug-like scaffolds. Its application is demonstrated through designing a novel series of 1,5-diarylpyrazoles for cyclooxygenase-2 (COX-2) inhibition. [Display omitted] The hemiaminals obtained as a major product during ortho-acylation attempt of benzenesulfonamide were in situ reduced to pharmacophoric 2-hydroxyalkyl benzenesulfonamide intermediates and used in designing drug-like scaffolds.
ISSN:0223-5234
1768-3254
DOI:10.1016/j.ejmech.2006.09.021