Combinatorial chemistry of hydantoins

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 17, 1998, Pages 2375-2380

  Boeijen, Astrid ^a   Kruijtzer, John A W ^a   Liskamp, Rob M J ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

HYDANTOIN;

AMINATION; AMINO ACID SEQUENCE; ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

DATABASES; DRUG DESIGN; HYDANTOINS; INDICATORS AND REAGENTS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0032497353     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00429-6     Document Type: Article

References (20)

1. 1. See e.g.: Gordon, D. W.; Steele, J. Bioorg. Med. Chem. Lett. 1995, 5, 47; Szardenings, A. K.; Burkoth, T. S.; Lu, H. H.; Tien, D. W.; Campbell, D. A. Tetrahedron 1997, 53, 6573; Scott, B. O.; Siegmund, A. C.; Marlowe, C. K.; Pei, Y.; Spear, K. L. Molecular Diversity 1995, 1, 125.
2. 1. See e.g.: Gordon, D. W.; Steele, J. Bioorg. Med. Chem. Lett. 1995, 5, 47; Szardenings, A. K.; Burkoth, T. S.; Lu, H. H.; Tien, D. W.; Campbell, D. A. Tetrahedron 1997, 53, 6573; Scott, B. O.; Siegmund, A. C.; Marlowe, C. K.; Pei, Y.; Spear, K. L. Molecular Diversity 1995, 1, 125.
3. 1. See e.g.: Gordon, D. W.; Steele, J. Bioorg. Med. Chem. Lett. 1995, 5, 47; Szardenings, A. K.; Burkoth, T. S.; Lu, H. H.; Tien, D. W.; Campbell, D. A. Tetrahedron 1997, 53, 6573; Scott, B. O.; Siegmund, A. C.; Marlowe, C. K.; Pei, Y.; Spear, K. L. Molecular Diversity 1995, 1, 125.
4. 2. (a) DeWitt, S. H.; Kiely, J. S.; Stankovic, C. J.; Schroeder, M. C.; Reynolds Cody, D. M.; Pavia, M. R. Proc. Natl. Acad Sci. 1993, 90, 6909;
5. (b) Dressmann, B. A.; Spangle, L. A.; Kaldor, S. W. Tetrahedron Lett. 1996, 37, 937;
6. (c) Kim, S. W.; Ahn, S. Y.; Koh, J. S.; Lee, J. H.; Ro, S.; Cho, H. Y. Tetrahedron Lett. 1997, 38, 4603;
7. (d) Matthews, J.; Rivero, R. A. J. Org. Chem. 1997, 62, 6090;
8. (e) Sim, M. M.; Ganesan, A. J. Org. Chem. 1997, 62, 3230;
9. (f) Xiao, X.; Ngu, K.; Chao, C.; Patel, D. V. J. Org. Chem. 1997, 62, 6968.
10. 3. Kruijtzer, J. A. W.; Liskamp, R. M. J. Tetrahedron Lett. 1995, 36, 6969; Kruijtzer, J. A. W. Thesis, Utrecht University 1996; Kruijtzer, J. A. W.; Hofmeyer, L. J. F.; Heerma, W.; Versluis C.; Liskamp, R. M. J. Chem. Eur. J. accepted for publication.
11. 3. Kruijtzer, J. A. W.; Liskamp, R. M. J. Tetrahedron Lett. 1995, 36, 6969; Kruijtzer, J. A. W. Thesis, Utrecht University 1996; Kruijtzer, J. A. W.; Hofmeyer, L. J. F.; Heerma, W.; Versluis C.; Liskamp, R. M. J. Chem. Eur. J. accepted for publication.
12. 3. Kruijtzer, J. A. W.; Liskamp, R. M. J. Tetrahedron Lett. 1995, 36, 6969; Kruijtzer, J. A. W. Thesis, Utrecht University 1996; Kruijtzer, J. A. W.; Hofmeyer, L. J. F.; Heerma, W.; Versluis C.; Liskamp, R. M. J. Chem. Eur. J. accepted for publication.
13. 4. Reichwein, J. F.; Liskamp, R. M. J. Tetrahedron Lett. 1998, 39, 1243.
14. 5. To our knowledge all reported methods (see ref 2) involve at least heating in the presence of base.
15. 6. Boeijen, A.; Liskamp, R. M. J. manuscript in preparation.
16. 7. A protected amino acid or peptoid (N-substituted glycine) monomer was esterified to a polyethylene-glycol grafted polystyrene resin (Tentagel® S-OH, 0.30 mmol/g) in a mixed anhydride coupling method employing 2,6-dichlorobenzoyl chloride as was described by Sieber: Sieber, P. Tetrahedron Lett. 1987, 28, 6147.
17. 8. General procedure for the preparation of a hydantoin: resin bound amino acid 4 or peptoid monomer 7 (500 mg, 0.27 mmol/g) was washed with NMP (3 × 5 mL) and subsequently treated with a solution of 20% piperidine in NMP. Agitation was effected by nitrogen bubbling. After 20 min the solvent was removed by filtration and the resin was washed with NMP (5 × 5 mL). A solution of an isocyanate (0.81 mmol, 6 equivs.) and DIEA (23 μL, 0.14 mmol, 1 equiv) in NMP (2.5 mL) was added. After 3 h, the solvent was removed by filtration. Cyclization/cleavage was effected by addition of a mixture of 10% TEA/MeOH (10 mL) and shaking for 3 h, followed by washing of the resin with MeOH (3 × 5 mL) and DCM (3 × 5 mL). Evaporation of the filtrate and purification by rapid column chromatography (silica, eluent EtOAc) afforded the desired product.
18. 3) δ 19.6, 44.0, 46.6, 48.8, 128.1, 129.0, 135.5, 169.7 ppm.
19. 10. MULTIBLOCK is distributed by: CSPS, P.O. Box 68212, Tuscon, AZ 85737, USA and SciTech, Nad Sarkou 75, 160 00 Praha 6, Czech Republic
20. 11. Possibly the increased flexibility of the glycine derivatives is counterproductive for formation of the hydantoin ring.