Study of biscarbamates derived from 2-aminobenzylamines as models for alcohol prodrugs

Tetrahedron

Volumn 55, Issue 15, 1999, Pages 4699-4708

  Papot, Sébastien ^a   Bachmann, Christian ^a   Combaud, Damien ^a   Gesson, Jean Pierre ^a  

^a UNIVERSITÉ DE POITIERS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; BENZYLAMINE DERIVATIVE; CARBAMIC ACID DERIVATIVE; PRODRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CHEMOTHERAPY; CHEMICAL MODIFICATION; CHEMICAL REACTION; CYCLIZATION; CYTOTOXICITY; DRUG SELECTIVITY; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; REACTION TIME;

EID: 0033537963     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00139-8     Document Type: Article

References (33)

1. a) Bagshawe, K.D. Drug Dev. Res. 1995, 34, 220-230.
2. b) Niculescu-Duvaz, I.; Springer, C. J. Curr. Med. Chem. 1995, 2, 687-706.
3. c) Melton, R.G.; Sherwood, R.F. J. Natl. Cancer Inst. 1996, 21, 153-165.
4. For a review see: Sperker, B.; Backman, J.T.; Kroemer, H.K. Clin. Pharmacokinet. 1997, 33, 18-31. Monneret, C.; Florent, J.-C.; Gesson, J.-P.; Jacquesy, J.-C.; Tillequin, F.; Koch, M. ACS Symp. Ser. 1995, 574, 78-99. Bosslet, K.; Straub, R.; Blumrich, M.; Czech, J.; Gerken, M.; Sperker, B.; Kroemer, H.K.; Gesson, J.-P.; Koch, M.; Monneret, C. Cancer Res. 1998, 58, 1195-1201 and references cited therein.
5. For a review see: Sperker, B.; Backman, J.T.; Kroemer, H.K. Clin. Pharmacokinet. 1997, 33, 18-31. Monneret, C.; Florent, J.-C.; Gesson, J.-P.; Jacquesy, J.-C.; Tillequin, F.; Koch, M. ACS Symp. Ser. 1995, 574, 78-99. Bosslet, K.; Straub, R.; Blumrich, M.; Czech, J.; Gerken, M.; Sperker, B.; Kroemer, H.K.; Gesson, J.-P.; Koch, M.; Monneret, C. Cancer Res. 1998, 58, 1195-1201 and references cited therein.
6. For a review see: Sperker, B.; Backman, J.T.; Kroemer, H.K. Clin. Pharmacokinet. 1997, 33, 18-31. Monneret, C.; Florent, J.-C.; Gesson, J.-P.; Jacquesy, J.-C.; Tillequin, F.; Koch, M. ACS Symp. Ser. 1995, 574, 78-99. Bosslet, K.; Straub, R.; Blumrich, M.; Czech, J.; Gerken, M.; Sperker, B.; Kroemer, H.K.; Gesson, J.-P.; Koch, M.; Monneret, C. Cancer Res. 1998, 58, 1195-1201 and references cited therein.
7. Houba; P.J.; Leenders, R.G.G.; Boven, E.; Scheeren, J.W.; Pinedo, H.M.; Haisma, H.J. Biochem. Pharmacol. 1996, 52, 455-463.
8. Schmidt, F.; Florent, J.-C.; Monneret, C.; Straub, R.; Czech, J.; Gerken, M.; Bosslet, K. Bioorg. Med. Chem. Lett. 1997, 7, 1071-1076.
9. Hutchins, J.E.C.; Fife, T.H. J. Am. Chem. Soc. 1973, 95, 2282-2286.
10. Vigroux, A.; Bergon, M. Bioorg. Med. Chem. Lett. 1995, 5, 427-430.
11. Vigroux, A.; Bergon, M.; Zedde, C. J. Med. Chem. 1995, 38, 3983-3994.
12. Leenders, R.G.G.; Gerrits, K.A.A.; RuiJtenbeek, R.; Scheeren, H.W.; Haisma, H.J.; Boven, E. Tetrahedron Lett. 1995, 36, 1701-1704.
13. Amsberry, K.I.; Borchardt, R.T. J. Org. Chem. 1990, 55, 5867-5877 and references cited therein.
14. Carpino, L.A.; Triolo, S.A.; Berglund, R.A. J. Org. Chem. 1989, 54, 3303-3310.
15. Sammes, P.G.; Weller, D.J. Synthesis, 1995, 1205-1222.
16. Alvernhe, G.; Laurent, A. Tetrahedron Lett. 1973, 1057-1060.
17. Coyne, W.E.; Cusic, J.W. J. Med. Chem. 1968, 11, 1208-1213.
18. These were chosen as representative secondary and primary alcohols.
19. Compound 13 has previously been obtained from urea and 2-(2-amino-phenyl)-2-methyl-propanol. See: Bernardi, L.; Bonsignori, A.; Coda, S.; Suchowsky, G.K. Ger. Offen. 1,958,515 1970; Chem. Abstr. 1970, 73, 77279n.
20. Compound 13 has previously been obtained from urea and 2-(2-amino-phenyl)-2-methyl-propanol. See: Bernardi, L.; Bonsignori, A.; Coda, S.; Suchowsky, G.K. Ger. Offen. 1,958,515 1970; Chem. Abstr. 1970, 73, 77279n.
21. Reaction with the corresponding chloroformate was not selective.
22. Slower debenzylation was observed with ethyl acetate as solvent (2 h). Under these conditions only 14 was isolated from the reaction mixture.
23. Cyclisation was followed by HPLC : reverse phase column : Zorbax, 5 μ ODS, 25 × 4.6 mm); eluent : 1/1 acetonitrile/0.02 M phosphate buffer (pH 4.5 or 7), UV detection at 486 nm. Retention time: 12: 14.7 min; 14 : 5.2 min.
24. The Gaussian 94 program was used. Gaussian 94 (Revision B.2), Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. .Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A., Gaussian, Inc., Pittsburgh, PA, 1995.
25. Williams, I. H.; Spangler, D.; Maggiora, G. M.; Schowen, R. L., J. Am. Chem. Soc. 1985, 107, 7717-7723.
26. (a) Becke's three parameters hybrid method using the LYP correlation functional as implemented in Gaussian 94.
27. (b) Becke, A. D., J. Chem. Phys. 1993, 98, 5648-5652.
28. (c) Lee, C.; Yang, W.; Parr, R. G., Phys. Rev. B 1988, 37, 785-789.
29. The same conformational bias has been observed and calculated for acetanilide and N-methylacetanilide. See: Saito, S.; Toriumi, Y.; Tomioka, N.; Itai, A. J. Org. Chem. 1995, 60, 4715-4720 ; Mannea, V.P.; Wilson, K.J.; Cable, J.R. J. Am. Chem. Soc. 1997, 119, 2033-2039.
30. The same conformational bias has been observed and calculated for acetanilide and N-methylacetanilide. See: Saito, S.; Toriumi, Y.; Tomioka, N.; Itai, A. J. Org. Chem. 1995, 60, 4715-4720 ; Mannea, V.P.; Wilson, K.J.; Cable, J.R. J. Am. Chem. Soc. 1997, 119, 2033-2039.
31. In an additive RHF/3-21G calculation, we have estimated the destabilization resulting from a rotation of 90° around the C(1)-N bond (i.e. rotating the carbamate group with respect to the benzenic ring) in 15. A destabilization of ≈ 9kcal/mol has resulted.
32. Florent, J.-C.; Dong, X.; Gaudel, G.; Mitaku, S.; Monneret, C.; Gesson, J.-P.; Jacquesy, J.-C.; Mondon, M.; Renoux, B.; Andrianomenjanahary, S.; Michel, S.; Koch, M. Tillequin, F.; Gerken, M.; Czech, J.; Straub, R.; Bosslet, K. J. Med. Chem. 1998, 41, 3572-3581.
33. Papot, S., Combaud, D.; Gesson, J.-P. Bioorg. Med. Chem. Lett. 1998, 8, 2545-2548.