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AAPS PharmSciTech. 2000 September; 1(3): 1–4.
Published online 2000 August 25. doi:  10.1208/pt0103_tn1
PMCID: PMC2750343

Competitive inhibitory effect of external nucleophile concentration on intramolecular O- to N-acylation in O-acetylsalicylamide

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Selected References

These references are in PubMed. This may not be the complete list of references from this article.
1. Babhair SA, Hussain AA. O-Acetylsalicylamides as possible prodrugs for salicylamide. I. Kinetics and mechanisms of their degradation and reaction with enzymes and sodium bisulfite. Int J Pharm. 1983;13:273–286. doi: 10.1016/0378-5173(83)90076-5. [Cross Ref]
2. Tawfiq FA, Dittert LW, Hussain AA, Crooks PA. Kinetics of decomposition of O-acyl derivatives of salicylamide and related compounds. Int J Pharm. 1990;64:43–55. doi: 10.1016/0378-5173(90)90177-6. [Cross Ref]
3. Tawfiq FA, Dittert LW, Hussain AA, Crooks PA. Rearrangement of O-acetylsalicylamides via O to N transacylation: rate enhancement by an adjacent carboxylic acid group. J Pharm Sci. 1990;79:651–651. doi: 10.1002/jps.2600790724. [PubMed] [Cross Ref]
4. Munson JW, Hussain AA, Bilous R. Precautionary note for use of bisulfite in pharmaceutical formulations. J Pharm Sci. 1977;66:1775–1776. doi: 10.1002/jps.2600661234. [PubMed] [Cross Ref]
5. Menger FM, Ladika M. Fast hydrolysis of an aliphatic amide at neutral pH and ambient temperature. A peptidase model. J Amer Chem Soc. 1988;110:6794–6796. doi: 10.1021/ja00228a031. [Cross Ref]
6. Bernhard SA, Berger A, Carter JH, Katchalski E, Sela M, Shalitin Y. Co-operative effects of functional groups in peptides. I. Aspartyl-serine derivatives. J Amer Chem Soc. 1962;84:2421–2434. doi: 10.1021/ja00871a030. [Cross Ref]

Articles from AAPS PharmSciTech are provided here courtesy of American Association of Pharmaceutical Scientists