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Bioorganic and Medicinal Chemistry

Volumn 9, Issue 3, 2001, Pages 621-628

Ring-deactivated hydroxymethylpyrroles as inhibitors of α-chymotrypsin

(2) Abell, Andrew D a Nabbs, Brent K a

a UNIVERSITY OF CANTERBURY (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

CHYMOTRYPSIN; ENZYME INHIBITOR; HYDROXYMETHYLPYRROLE DERIVATIVE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; DRUG SCREENING; DRUG SYNTHESIS; ENZYME INHIBITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ACTIVITY RELATION;

ANIMALS; CATTLE; CHYMOTRYPSIN; KINETICS; PYRROLES; SERINE PROTEINASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0035102461 PISSN: 09680896 EISSN: None Source Type: Journal
DOI: 10.1016/S0968-0896(00)00274-1 Document Type: Article

Times cited : (16)

References (16)

1
- 0005849551
- (a) Abell, A. D.; Nabbs, B. K.; Battersby, A. R. J. Am. Chem. Soc. 1998, 120, 1741. (b) Abell, A. D.; Nabbs, B. K.; Battersby, A. R. J. Org. Chem. 1998, 63, 8163. (c) Abell, A. D.; Nabbs, B. K. Org. Lett. 1999, 1, 1403. (d) Abell, A. D.; Litten, J. C. Tetrahedron Lett. 1992, 3005.

2
- 0005892735
- (1998) J. Chem. Soc., Chem. Commun. , vol.919
- Abell, A.D.¹ Litten, J.C.² Nabbs, B.K.³

3
- 0005817738
- Jones, A. R., Bean, G. P., Eds.; The Chemistry of Pyrroles Academic: London, 1977, pp 356-357. Katritzky, A. R., Rees, C. W., Eds.; Comprehensive Heterocyclic Chemistry; Pergamon: Oxford, 1984, Vol. 4.

4
- 0005890797
- Wallace, D. M.; Leung, S. H.; Smith, K. M. J. Org. Chem. 1993, 58, 7245. Tietze, L. F.; Kettschau, G.; Heitmann, K. Synthesis 1996, 851.

5
- 0005818376
- Battersby, A. R.; Fookes, C. J. R.; Gustafson-Potter, K. E.; McDonald, E.; Matcham, G. W. T. J. Chem. Soc., Perkin Trans 1 1982, 2427. Battersby, A. R., Leeper, F. J. Chem. Rev. 1990, 90, 1261. Scott, A. I. In Advances in Detailed Reaction Mechanisms: Mechanisms of Biological Importance; Coxon, J. M. Ed.; JAI: Connecticut, 1992; pp 189-212.

6
- 0005871007
- Silverman, R. B. In Mechanism-Based Enzyme Inactivation: Chemistry and Enzymology; CRC, Florida, 1988; Vols 1 and 2. Abell, A. D. In Detailed Reaction Mechanisms: Mechanisms of Biological Importance; Coxon, J., Ed.; JAI: London, 1992; Vol. 2, pp 243-260. Rando, R. R. Science 1974, 185, 320.

7
- 0005863409
- 1 amino acid defines the point of cleavage of the substrate peptide where, by definition, hydrolysis occurs on the carboxyl side of this residue (for a definition of this nomenclature see: Schechter, I.; Berger, A. Biochem. Biophys. Res. Commun. 1967, 27, 157).

8
- 0005824169
- The choice of protecting group (N-phthaloyl) and the amino acid (leucine) were dictated by ease of synthesis (unpublished results).

9
- 0005777921
- We have previously shown that an N-sulfonyl group is superior to an N-acyl group at deactivating a hydroxymethylpyrrole (see ref 1a). As a consequence these compounds tend to be more stable and are in many cases crystalline solids.

10
- 0005871008
- The use of the acid fluoride, rather than the acid chloride, gave a much better yield of the desired product. Acid fluorides have also been reported to minimise epimerisation at the amino acid stereogenic centre in reactions of this type (see ref 14).

11
- 0005777922
- Fersht, A. Enzyme Structure and Mechanism, 2nd ed.; W. H. Freeman: New York, 1985; pp 17-22.

12
- 0000070737
- (1993) Aust. J. Chem. , vol.46 , pp. 1473
- Abell, A.D.¹ Litten, J.C.²

13
- 0000426222
- (1994) J. Org. Chem. , vol.59 , pp. 5230
- Schloemer, G.C.¹ Greenhouse, R.² Muchowski, J.M.³

14
- 0005890799
- (1992) Tetrahedron , vol.33 , pp. 3005
- Savrda, J.¹ Chertanova, L.² Wakselman, M.³

15
- 85078318932
- (1986) Synthesis , pp. 620
- Hinz, W.¹ Jones, R.A.² Anderson, T.³

16
- 0005856322
- (1979) Khim. Geterotsikl. Soedin , vol.7 , pp. 916
- Eraksina, V.N.¹ Ivanova, T.M.² Babushkina, T.A.³ Vasil'ev, A.M.⁴ Suvorov, N.N.⁵

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