Design of β-lactams with mechanism based nonantibacterial activities

Current Medicinal Chemistry

Volumn 10, Issue 17, 2003, Pages 1741-1757

  Veinberg, Grigory ^a   Vorona, Maxim ^a   Shestakova, Irina ^a   Kanepe, Iveta ^a   Lukevics, Edmunds ^a  

^a LATVIAN INSTITUTE OF ORGANIC SYNTHESIS   (Latvia)

Author keywords

[No Author keywords available]

Indexed keywords

3 ACETOXYMETHYL 2 (2 CARBOXY 1 PYRROLIDINYLCARBONYL) 7ALPHA METHOXY 8 OXO 5 THIA 1 AZABICYCLO[4.2.0]OCT 2 ENE 5,5 DIOXIDE; 3 DECYLDIMETHYLSILYL N [2 (4 METHYLPHENYL) 1 PHENYLETHYL]PROPIONAMIDE; 6 AMINOPENICILLANIC ACID; 7 (DIBROMOMETHYLENE)CEPHALOSPORANIC ACID; 7 AMINOCEPHALOSPORANIC ACID; ACETYLSALICYLIC ACID DERIVATIVE; ACYLTRANSFERASE; ANTIINFLAMMATORY AGENT; AZETIDINONE DERIVATIVE; BETA LACTAM ANTIBIOTIC; BETA LACTAM DERIVATIVE; CALPASTATIN; CEPHALOSPORIN DERIVATIVE; CEPHAM DERIVATIVE; CEPHEM DERIVATIVE; CHOLESTEROL ACYLTRANSFERASE INHIBITOR; CYSTEINE PROTEINASE; ELASTASE; ELASTASE INHIBITOR; GW 311616A; LACTAM DERIVATIVE; N [1 (1,3 BENZODIOXOL 5 YL)BUTYL] 3,3 DIETHYL 2 [4 [(4 METHYL 1 PIPERAZINYL)CARBONYL]PHENOXY] 4 OXO 1 AZETIDINECARBOXAMIDE; PENAM DERIVATIVE; PENICILLIN DERIVATIVE; PENICILLIN G DERIVATIVE; PHOSPHOLIPASE A2; PROTEINASE INHIBITOR; SERINE PROTEINASE; THROMBIN INHIBITOR; UNCLASSIFIED DRUG; UNINDEXED DRUG;

CANCER; CARDIOVASCULAR DISEASE; CHIRALITY; COMPLEX FORMATION; DRUG BINDING; DRUG BIOAVAILABILITY; DRUG DESIGN; DRUG MECHANISM; DRUG STRUCTURE; DRUG TARGETING; ENZYME ACTIVE SITE; ENZYME ACTIVITY; HUMAN; IN VITRO STUDY; IN VIVO STUDY; INFLAMMATORY DISEASE; MOLECULAR MODEL; MOLECULAR STABILITY; NONHUMAN; PATHOPHYSIOLOGY; REGULATORY MECHANISM; RESPIRATORY TRACT DISEASE; REVIEW; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

ACYLTRANSFERASES; ANTIFUNGAL AGENTS; ANTINEOPLASTIC AGENTS; ANTIVIRAL AGENTS; BETA-LACTAMS; CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; DRUG INTERACTIONS; ENZYME INHIBITORS; HUMANS; PANCREATIC ELASTASE; PHOSPHOLIPASES A; PROSTATE-SPECIFIC ANTIGEN; PROTEASE INHIBITORS; THROMBIN;

EID: 0042423395     PISSN: 09298673     EISSN: None     Source Type: Journal    
DOI: 10.2174/0929867033457089     Document Type: Review

References (72)

1. Doherty, J.B., Ashe, B.M., Argenbright, L.W., Barker, P.L., Bonney, R.J., Chandler, G.O., Dahlgren, M.E., Dorn, Jr C.P., Finke, P.E., Firestone, R.A., Fletcher, D., Hagmann, W.K., Mumford, R., O'Grady, L., Maycock, A.L., Pisano, J.M., Shah, S.K., Thompson, K.R., Zimmerman, M. Nature, 1986, 322, 192-194.
2. Doherty, J.B., Ashe, B.M., Barker, P.L., Blacklock, T.J., Butcher, J.W., Chandler, G.O., Dahlgren, M.E., Davies, P., Dorn, Jr C.P., Finke, P.E., Firestone, R.A., Hagmann, W.K, Halgren, T., Knight, W.B., Maycock, A.L, Navia, M.A, O'Grady, L., Pisano, J.M., Shah, S.K., Thompson, K.R., Weston, H, Zimmerman, M. J. Med Chem., 1990, 33, 2513-2521.
3. Finke, P.E., Ashe, B.M., Knight, W.B., Maycock, A.L., Navia, M.A., Shah, S.K, Thompson, K.R., Underwood, D.J., Weston, H., Zimmerman, M., Doherty, J.B. J. Med. Chem., 1990, 33, 2522-2528.
4. Shah, S.K., Brause, K.A., Chandler, G.O., Finke, P.E., Ashe, B.M., Weston, H., Knight, W.B., Maycock, A.L., Doherty, J.B. J. Med. Chem., 1990, 33, 2529-2535.
5. Navia, M.A., Springer, J.P., Lin, T.-Y., Williams, H.R., Firestone, R.A., Pisano, J.M., Doherty, J.B., Finke, P.E., Hoogsteen, K. Nature, 1987, 327, 79-82.
6. Finke, P.E., Shah, S.K, Ashe, B.M., Ball, R.G., Blacklock, J.T., Bonney, R.J., Brause, KA., Chandler, G.O., Cotton, M., Davies, P., Dellea, P.S., Dorn, Jr C.P., Fletcher, D.S., O'Grady, L., Hagmann, W.K., Hand, K.M., Knight, W.B., Maycock, A.L., Mumford, R.A., Osinga, D.G., Sohar, P., Thompson, K.R., Weston, H., Doherty, J.B. J. Med. Chem., 1992, 35, 3731-3744.
7. Bandoli, G., Dolmella, A., Gatto, S., de Angelis, F. Eur. J. Med. Chem., 1997, 32, 219-230.
8. Alpegiani, M., Baici, A., Bissolino, P., Carminati, P., Cassinelli, G., Del Nero, S., Franceschi, G., Orezzi, P, Perrone, E, Rizzo, V, Sacchi, N. Eur. J. Med. Chem., 1992, 27, 875-890.
9. Alpegiani, M., Bissolino, P., Corigli, R., Del Nero, S, Perrone, E., Rizzo, V., Sacchi, N., Cassinelli, G., Franceschi, G. J. Med. Chem., 1994, 37, 4003-40019.
10. Alpegiani, M., Bissolino, P., Corigli, R., Rizzo, V., Perrone, E. Bioorg. Med. Chem. Letters, 1995, 5, 687-690.
11. Balsmo, A., Cercignani, G., Centili, D., Lapucci, A., Macchia, M., Orlandini, E., Rapposelli, S., Rosello, A. Eur. J. Med. Chem., 2001, 36, 185-193.
12. Maiti, S.N., Czajkowski, D.P., Reddy, N.A.V., Spevak, P., Kaleta, J., Micetich, R.G. Bioorg. Med. Chem. Letters, 1996, 6, 823-826.
13. Reddy, A.V.N., Fiakpui, C.Y., Czajkowski, D.P., Spevak, P., Kaleta, J., Micetich, R.G., Maiti, S.N. Khim. Geterotsikl. Soedin., 1998, 1517-1523.
14. Reddy, A.V.N., Fiakpui, C.Y., Czajkowski, D. P., Kaleta, J., Micetich, R.G., Maiti, S.N. Khim. Geterotsikl. Soedin., 1998, 1510-1516.
15. Veinberg, G., Shestakova, I., Petrulanis, L., Grigan, N., Musel, D., Zeile, D., Kanepe, I., Domrachova, I., Kalvinsh, I., Strakovs, A., Lukevics, E. Bioorg. Med. Chem. Letters, 1997, 7, 843-846.
16. Veinberg, G., Vorona, M., Grigan, N., Kanepe, I, Shestakova, I., Strakov, A., Lukevics, E. Chem. Heterocycl. Comp. (Engl. Ed.), 2000, 36, 744-750.
17. Buynak, J.D., Rao, A.S., Ford, G.P., Carver, C., Adam, G., Geng, B., Bachmann, B., Shobassy, S., Lackey, S. J. Med. Chem., 1997, 40, 3423-3433.
18. Thompson, K.R., Finke, P.E., Shah, S.K., Ashe, B.M., Dahlgren, M.E., Maycock, A.L., Doherty, J.B. Bioorg. Med. Chem. Lett., 1993, 3, 2283-2288.
19. Thompson, K.R., Finke, P.E., Shah, S.K., Ashe, B.M., Dahlgren, M.E., Dellea, P.S., Fletcher, D.S., Hand, K.M., Maycock, A.L., Doherty, J.B. Bioorg. Med. Chem. Lett., 1993, 3, 2289-2294.
20. Boschetti, C.E., Mascaretti, O.A., Cricco, J.A., Roveri, O.A. Bioorg. Med. Chem., 1995, 3, 95-100.
21. Boschetti, C.E., Mata, E.G., Mascaretti, O.A. Bioorg. Med. Chem. Lett., 1995, 5, 2033-2036.
22. Finke, P.E., Dahlgren, M.E., Weston, H., Maycock, A.L., Doherty, J.B. Bioorg. Med. Chem. Lett., 1993, 3, 2277-2282.
23. Faraci, W.S., Bakker, A.V., Spencer, R.W., Williams, R.A., Jasys, V.J., Kellogg, M.S., Volkmann, R.A. Bioorg. Med. Chem. Lett., 1993, 3, 2271-2276.
24. Firestone, R.A., Barker, P.L., Pisano, J.M., Ashe, B.M., Dahlgren, M.E. Tetrahedron, 1990, 46, 2255-2262.
25. Shah, S.K., Dorn, C.P., Finke, P.E., Hale, J.J., Hagmann, W.K., Brause, K.A., Chandler, G.O., Kissinger, A.L., Ashe, B.M., Weston, H., Knight, W.B., Maycock, A.L., Dellea, P.S., Fletcher, D.S., Hand, K.M., Mumford, R.A., Underwood, D.J., Doherty, J.B. J. Med. Chem., 1992, 35, 3745-3754.
26. Doherty, J. B., Shah, S.K., Finke, P. E., Dorn, C.P., Hagmann, W.K., Hale, J.J., Kissinger, A.L., Thompson, K.R., Brause, K., Chandler, G.O., Knight, W.B., Maycock, A.L., Ashe, B.M., Weston, H., Gale, P., Mumford, R. A., Andersen, O.F., Williams, H. R., Nolan, T.E., Frankenfield, D.L., Underwood, D., Vyas, K.P., Kari, P.H., Dahlgren, M.E., Mao, J., Fletcher, D.S., Dellea, P.S., Hand, K.M., Osinga, D.G., Peterson, L.B., Williams, D.T., Metzger, J.M., Bonney, R.J., Humes, J.L., Pacholok, S.P., Hanlon, W.A., Opas, E., Stolk, J., Davies, P. Proc. Natl. Acad. Sci. USA, 1993, 93, 8727-8731.
27. Knight, W.B., Green, B.G., Chabin, R.M., Gale, P., Maycock, A.L., Weston, H., Kuo, D.W., Westler, W.M., Dorn, C.P., Finke, P.E., Hagmann, W.K., Hale, J.J., Liesch J., MacCoss, M., Navia, M.A., Shah, S.K., Underwood, D., Doherty, J.B. Biochemistry, 1992, 31, 8160-8170.
28. Taylor, P., Anderson, V., Dowden, J., Flitsch, S.L., Turner, N.J., Loughran, K., Walkinshaw, M.D. J. Biol. Chem., 1999, 274, 24901-24905.
29. Maillard, J.-L., Favreau, C., Reboud-Ravaux, M., Kobaiter, R., Joyeau, R., Wakselman, M. Eur. J. Cell Biol., 1990, 52, 213-218.
30. Vergely, I., Boggetto, N., Okochi, V., Golpayegani, S., Reboud-Ravaux, M., Kobaiter, R., Joyeau, R., Wakselman, M. Eur. J. Med. Chem., 1995, 30, 199-208.
31. Wilmouth, R.C., Kassmally, S., Westwood, N.J., Sheppard, R.J., Calridge, T.D.W., Aplin, R.T., Wright, P.A., Pritchard, G.J., Schofield, C.J. Biochemistry, 1999, 38, 7989-7998.
32. Westwood, N.J., Calridge, T.D.W., Edwards, P.N., Schofield, C.J. Bioorg. Med. Chem. Letters, 1997, 4, 2973-2978.
33. Macdonald, S.J.F., Belton, D.J., Buckley, D.M., Spooner, J.E., Anson, M.S., Harrison, L.A., Mills, K., Upton, R.J., Dowle, M.D., Smith, R.A., Molloy, C.R., Risley, C. J. Med. Chem., 1998, 41, 3919-3922.
34. Macdonald, S.J.F., Dowle, M.D., Harrison, L.A., Shah, P., Johnson, M.R., Inglis, G.G.A., Clarke, G.D.E., Smith, R.A., Humphreys, D., Molloy, C.R., Amour, A., Dixon, M., Murkitt, G., Godward, R.E., Padfield, T., Skarzynski, T., Singh, O.M.P., Kumar, K.A., Fleetwood, G., Hodson, S.T., Hardy, G.W., Finch, H. Bioorg. Med. Chem. Lett., 2001, 11, 895-898.
35. Baxter, N.J., Laws, A.P., Rigoreau, L.J.M., Page, M.J. J. Am. Chem. Soc., 2000, 122, 3375-3385
36. Beardsell, M., Hinchliffe, P.S., Wood, J.M., Wilmouth, R.C., Schofield, C.J., Page, M.I. Chem. Commun., 2001, 497-498.
37. Han, W.T., Trehan, A.K., Wright, J.J.K., Federici, M.E., Seiler, S.M., Meanwell, N.A. Bioorg. Med. Chem., 1995, 3, 1123-1143.
38. Aldington, R.M., Baldwin, J.E., Chen, B., Cooper, S.L., McCoull, W., Pritchard, G.J. Bioorg. Med. Chem. Lett., 1997, 7, 1689-1694.
39. Annunziata, R., Benaglia, M., Cinquini, M., Cozzi, F., Puglisi, A. Bioorg. Med. Chem., 2002, 10, 1813-1818.
40. Borthwick, A., D., Weingarten, G., Haley, T., M., Tomaszewski, M., Wang, W., Hu, Z., Bedard, J., Jin, H., Yuen, L., Mansour, T.S. Bioorg. Med. Chem. Lett., 1998, 8, 365-370.
41. Deziel, R., Malenfant, B. Bioorg. Med. Chem. Lett., 1998, 8, 1437-1442.
42. Yoakim, C., Ogilvie, W.W., Cameron, D.R., Chabot, C., Guse, I., Hache, B., Naud, J., O'Meara, J.A., Plante, R., Deziel, R. J. Med. Chem., 1998, 41, 2882-2291.
43. Ogilvie, W.W., Yoakim, C., Do, F., Hache, B., Lagace, L., Naud, J., O'Meara, J.A., Deziel, R. Bioorg. Med. Chem., 1999, 7, 1521-1531.
44. Bonneau, P.R., Hasani, F., Plouffe, C., Malenfant, E., LaPlane, S.R., Guse, I., Ogilvie, W.W., Plante, R., Dvidson, W.C., Hopkins, J.L., Morelock, M.M., Cordingley, M.G., Deziel, R. J. Am. Chem. Soc., 1999, 121, 2965-2973.
45. Singh, R., Zhou, N.E., Guo, D., Micetich, R.G. PCT Int. Appl. WO 98/32766.
46. Singh, R., Zhou, N.E., Guo, D., Micetich, R.G. US Pat. 5959123, 1999.
47. Singh, R., Zhou, N.E., Guo, D., Micetich, R.G. US 5916887, 1999.
48. Gallagher, G., Gleason, J.G., Kingsbury, W.D., Pendrak I. PCT Int. Appl. WO 98/37084.
49. Tew, D.G., Boyd, H.F., Ashman, S., Theobald, C., Leach, C.A. Biochemistry, 1998, 37, 10087-10093.
50. Hickey, D., M.B., Dhanak, D., Ife, R.J., Leach, C.A., Tew, D.G. PCT Int. Appl. WO 97.21675.
51. Leach, C.A., Hickey, D.M.B., Ife, R.J., Dhanak, D., Theobald, C. PCT Int. Appl. WO 97/41098.
52. Winkler, J.D., Sung, C.-M., Chabot-Flecher, M., Griswold, D.E., Marshall, L.A., Chilton, F.H., Bondinell, W., Mayer, R.J. Mol. Pharmacol., 1998, 53, 322-328.
53. Burnett, D.A., Caplen, M.A., Davis, Jr. H.R., Burrier, R.E., Clader, J.W. J. Med. Chem., 1994, 37, 1733-1736.
54. Vaccaro, W.D., Sher, R., Davis, H.R. Jr. Bioorg. Med. Chem., 1998, 6, 1429-1437.
55. Vaccaro, W.D., Davis, H.R. Jr. Bioorg. Med. Chem. Lett., 1998, 8, 313-318.
56. Vaccaro, W.D., Sher, R., Davis, H.R. Jr. Bioorg. Med. Chem. Lett., 1998, 8, 319-322.
57. Rosenblum, S.B., Huynh, T., Afonso, A., Davis, Jr. H.R., Yumibe, N., Clader, J.W., Burnett, D.A. J. Med. Chem., 1998, 41, 973-980.
58. Burnett, D.A., Caplen, M., A., Domalski, M.S., Browne, M.E., Davis, Jr. H.R., Clader, J.W. Bioorg. Med. Chem. Lett., 2002, 12, 311-314.
59. Seiki, N., Den, K., Marunaka, T., Miyake, Y., Minumi, Y, Kajitani, A., Ishida, N. JP 61212587, 1986.
60. Peter, H., Zaehner H. DE 3427651, 1985.
61. Otani, T., Oie, S., Matsumoto, H., Tempest, M., Micetich, R.G., Singh, R., Yamashita, T. PCT Int. Appl. WO 94/01109, 1994.
62. Alpegiani, M., Bissolino, P., Perrone, E. Pesenti, E. PCT Int. Appl. WO 95/02603, 1995.
63. Liotta, L.A., Roo, C.N. Tumor Invasation and Methastasis. New Concepts in Neoplasma as Applied to Diagnostic Pathology. Williams and Wilkins, Baltimore, 1986.
64. Veinberg, G., Bokaldere, R., Dikovskaya, K., Vorona, M., Musel, D., Shestakova, I., Kanepe, I., Domrachova, I., Kalvinsh, I., Lukevics, E. LR Pat. 12403, 1998.
65. Veinberg, G.A., Shestakova, I., Grigan, N., Musel, D., Kanepe, I., Domrachova, I., Grigoryeva, V., Zharkova, O., Turovskis, I, Kalvinsh, I., Strakovs, A., Lukevics, E. Eur. J. Med. Chem., 1998, 33, 755-762.
66. Veinberg, G., Vorona, M., Shestakova, I., Kanepe, I., Zharkova, O., Mezapuke, R., Turovskis, I., Kalvinsh, I., Lukevics, E. Bioorg. Med. Chem., 2000, 8, 1033-1040.
67. Veinberg, G., Bokaldere, R., Dikovskaya, K., Vorona, M., Shestakova, I., Kanepe, I., Domrachova, I., Kalvinsh, I., Lukevics, E. LR Pat. 12373, 1998.
68. Brown, D., Evans, J.R. Chem. Commun., 1979, 282-283.
69. Konosu, T., Oida, S. Chem. Pharm. Bull., 1991, 39, 2212-2215.
70. Wanning, M., Zahner, H., Krone, B., Zeeck, A. Tetrahedron Lett., 1981, 22, 2539-2540.
71. Pruess, D.L., Kellet, M. J. Antibiotics, 1983, 36, 208-212.
72. King, H.D., Langharig, J., Sanglier, J. J. Antibiotics, 1986, 39, 510-515.