Constrained peptidomimetics: Building bicyclic analogs of pyrazoline derivatives

Tetrahedron

Volumn 59, Issue 43, 2003, Pages 8515-8523

  Liu, Bin ^a   Brandt, John D ^a   Moeller, Kevin D ^a  

^a WASHINGTON UNIVERSITY   (United States)

Author keywords

Bicyclic analogs; Proline surrogates; Pyrazoline

Indexed keywords

DIPEPTIDE; PROLINE; PYRAZOLINE DERIVATIVE;

AMINO TERMINAL SEQUENCE; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0141483290     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.09.027     Document Type: Article

References (31)

1. (a) Mish M., Guerra-Martinez F., Carreira E.M. J. Am. Chem. Soc. 119:1997;8379
2. (b) Guerra F.M., Mish M.R., Carreira E.M. Org. Lett. 2:2000;4265.
3. For the initial isolation of the acid see: (a) Morimoto K., Shimada N., Naganawa H., Takita T., Umezawa H. J. Antibiot. 34:1981;1615. For the synthesis of 2 and representative pyridazine acids see: (b) Attwood M.R., Hassall C.H., Kröhn A., Lawton G., Redshaw S. J. Chem. Soc., Perkin Trans. 1. 1986;1011 (c) Hughes P., Clardy J. J. Org. Chem. 54:1989;3260 (d) Schmidt U., Riedl B. Synthesis. 8:1993;809 (e) Nakamura Y., Ito A., Shin C. Bull. Chem. Soc. Jpn. 67:1994;2151 (f) Ciufolini M.A., Shimizu T., Swaminathan S., Xi N. Tetrahedron Lett. 38:1997;4947 (g) Xi N., Alemany L.B., Ciufolini M.A. J. Am. Chem. Soc. 120:1998;80 (h) Ciufolini M.A., Xi N. Chem. Soc. Rev. 27:1998;437 (i) Aspinall I.H., Cowley P.M., Mitchell G., Stoodley R.J. J. Chem. Soc., Chem. Commun. 15:1993;1179 (j) Aspinall I.H., Cowley P.M., Mitchell G., Raynor C.M., Stooley R.J. J. Chem. Soc., Perkin Trans. 1. 1999;2591.
4. For the initial isolation of the acid see: (a) Morimoto K., Shimada N., Naganawa H., Takita T., Umezawa H. J. Antibiot. 34:1981;1615. For the synthesis of 2 and representative pyridazine acids see: (b) Attwood M.R., Hassall C.H., Kröhn A., Lawton G., Redshaw S. J. Chem. Soc., Perkin Trans. 1. 1986;1011 (c) Hughes P., Clardy J. J. Org. Chem. 54:1989;3260 (d) Schmidt U., Riedl B. Synthesis. 8:1993;809 (e) Nakamura Y., Ito A., Shin C. Bull. Chem. Soc. Jpn. 67:1994;2151 (f) Ciufolini M.A., Shimizu T., Swaminathan S., Xi N. Tetrahedron Lett. 38:1997;4947 (g) Xi N., Alemany L.B., Ciufolini M.A. J. Am. Chem. Soc. 120:1998;80 (h) Ciufolini M.A., Xi N. Chem. Soc. Rev. 27:1998;437 (i) Aspinall I.H., Cowley P.M., Mitchell G., Stoodley R.J. J. Chem. Soc., Chem. Commun. 15:1993;1179 (j) Aspinall I.H., Cowley P.M., Mitchell G., Raynor C.M., Stooley R.J. J. Chem. Soc., Perkin Trans. 1. 1999;2591.
5. For the initial isolation of the acid see: (a) Morimoto K., Shimada N., Naganawa H., Takita T., Umezawa H. J. Antibiot. 34:1981;1615. For the synthesis of 2 and representative pyridazine acids see: (b) Attwood M.R., Hassall C.H., Kröhn A., Lawton G., Redshaw S. J. Chem. Soc., Perkin Trans. 1. 1986;1011 (c) Hughes P., Clardy J. J. Org. Chem. 54:1989;3260 (d) Schmidt U., Riedl B. Synthesis. 8:1993;809 (e) Nakamura Y., Ito A., Shin C. Bull. Chem. Soc. Jpn. 67:1994;2151 (f) Ciufolini M.A., Shimizu T., Swaminathan S., Xi N. Tetrahedron Lett. 38:1997;4947 (g) Xi N., Alemany L.B., Ciufolini M.A. J. Am. Chem. Soc. 120:1998;80 (h) Ciufolini M.A., Xi N. Chem. Soc. Rev. 27:1998;437 (i) Aspinall I.H., Cowley P.M., Mitchell G., Stoodley R.J. J. Chem. Soc., Chem. Commun. 15:1993;1179 (j) Aspinall I.H., Cowley P.M., Mitchell G., Raynor C.M., Stooley R.J. J. Chem. Soc., Perkin Trans. 1. 1999;2591.
6. For the initial isolation of the acid see: (a) Morimoto K., Shimada N., Naganawa H., Takita T., Umezawa H. J. Antibiot. 34:1981;1615. For the synthesis of 2 and representative pyridazine acids see: (b) Attwood M.R., Hassall C.H., Kröhn A., Lawton G., Redshaw S. J. Chem. Soc., Perkin Trans. 1. 1986;1011 (c) Hughes P., Clardy J. J. Org. Chem. 54:1989;3260 (d) Schmidt U., Riedl B. Synthesis. 8:1993;809 (e) Nakamura Y., Ito A., Shin C. Bull. Chem. Soc. Jpn. 67:1994;2151 (f) Ciufolini M.A., Shimizu T., Swaminathan S., Xi N. Tetrahedron Lett. 38:1997;4947 (g) Xi N., Alemany L.B., Ciufolini M.A. J. Am. Chem. Soc. 120:1998;80 (h) Ciufolini M.A., Xi N. Chem. Soc. Rev. 27:1998;437 (i) Aspinall I.H., Cowley P.M., Mitchell G., Stoodley R.J. J. Chem. Soc., Chem. Commun. 15:1993;1179 (j) Aspinall I.H., Cowley P.M., Mitchell G., Raynor C.M., Stooley R.J. J. Chem. Soc., Perkin Trans. 1. 1999;2591.
7. For the initial isolation of the acid see: (a) Morimoto K., Shimada N., Naganawa H., Takita T., Umezawa H. J. Antibiot. 34:1981;1615. For the synthesis of 2 and representative pyridazine acids see: (b) Attwood M.R., Hassall C.H., Kröhn A., Lawton G., Redshaw S. J. Chem. Soc., Perkin Trans. 1. 1986;1011 (c) Hughes P., Clardy J. J. Org. Chem. 54:1989;3260 (d) Schmidt U., Riedl B. Synthesis. 8:1993;809 (e) Nakamura Y., Ito A., Shin C. Bull. Chem. Soc. Jpn. 67:1994;2151 (f) Ciufolini M.A., Shimizu T., Swaminathan S., Xi N. Tetrahedron Lett. 38:1997;4947 (g) Xi N., Alemany L.B., Ciufolini M.A. J. Am. Chem. Soc. 120:1998;80 (h) Ciufolini M.A., Xi N. Chem. Soc. Rev. 27:1998;437 (i) Aspinall I.H., Cowley P.M., Mitchell G., Stoodley R.J. J. Chem. Soc., Chem. Commun. 15:1993;1179 (j) Aspinall I.H., Cowley P.M., Mitchell G., Raynor C.M., Stooley R.J. J. Chem. Soc., Perkin Trans. 1. 1999;2591.
8. For the initial isolation of the acid see: (a) Morimoto K., Shimada N., Naganawa H., Takita T., Umezawa H. J. Antibiot. 34:1981;1615. For the synthesis of 2 and representative pyridazine acids see: (b) Attwood M.R., Hassall C.H., Kröhn A., Lawton G., Redshaw S. J. Chem. Soc., Perkin Trans. 1. 1986;1011 (c) Hughes P., Clardy J. J. Org. Chem. 54:1989;3260 (d) Schmidt U., Riedl B. Synthesis. 8:1993;809 (e) Nakamura Y., Ito A., Shin C. Bull. Chem. Soc. Jpn. 67:1994;2151 (f) Ciufolini M.A., Shimizu T., Swaminathan S., Xi N. Tetrahedron Lett. 38:1997;4947 (g) Xi N., Alemany L.B., Ciufolini M.A. J. Am. Chem. Soc. 120:1998;80 (h) Ciufolini M.A., Xi N. Chem. Soc. Rev. 27:1998;437 (i) Aspinall I.H., Cowley P.M., Mitchell G., Stoodley R.J. J. Chem. Soc., Chem. Commun. 15:1993;1179 (j) Aspinall I.H., Cowley P.M., Mitchell G., Raynor C.M., Stooley R.J. J. Chem. Soc., Perkin Trans. 1. 1999;2591.
9. For the initial isolation of the acid see: (a) Morimoto K., Shimada N., Naganawa H., Takita T., Umezawa H. J. Antibiot. 34:1981;1615. For the synthesis of 2 and representative pyridazine acids see: (b) Attwood M.R., Hassall C.H., Kröhn A., Lawton G., Redshaw S. J. Chem. Soc., Perkin Trans. 1. 1986;1011 (c) Hughes P., Clardy J. J. Org. Chem. 54:1989;3260 (d) Schmidt U., Riedl B. Synthesis. 8:1993;809 (e) Nakamura Y., Ito A., Shin C. Bull. Chem. Soc. Jpn. 67:1994;2151 (f) Ciufolini M.A., Shimizu T., Swaminathan S., Xi N. Tetrahedron Lett. 38:1997;4947 (g) Xi N., Alemany L.B., Ciufolini M.A. J. Am. Chem. Soc. 120:1998;80 (h) Ciufolini M.A., Xi N. Chem. Soc. Rev. 27:1998;437 (i) Aspinall I.H., Cowley P.M., Mitchell G., Stoodley R.J. J. Chem. Soc., Chem. Commun. 15:1993;1179 (j) Aspinall I.H., Cowley P.M., Mitchell G., Raynor C.M., Stooley R.J. J. Chem. Soc., Perkin Trans. 1. 1999;2591.
10. For the initial isolation of the acid see: (a) Morimoto K., Shimada N., Naganawa H., Takita T., Umezawa H. J. Antibiot. 34:1981;1615. For the synthesis of 2 and representative pyridazine acids see: (b) Attwood M.R., Hassall C.H., Kröhn A., Lawton G., Redshaw S. J. Chem. Soc., Perkin Trans. 1. 1986;1011 (c) Hughes P., Clardy J. J. Org. Chem. 54:1989;3260 (d) Schmidt U., Riedl B. Synthesis. 8:1993;809 (e) Nakamura Y., Ito A., Shin C. Bull. Chem. Soc. Jpn. 67:1994;2151 (f) Ciufolini M.A., Shimizu T., Swaminathan S., Xi N. Tetrahedron Lett. 38:1997;4947 (g) Xi N., Alemany L.B., Ciufolini M.A. J. Am. Chem. Soc. 120:1998;80 (h) Ciufolini M.A., Xi N. Chem. Soc. Rev. 27:1998;437 (i) Aspinall I.H., Cowley P.M., Mitchell G., Stoodley R.J. J. Chem. Soc., Chem. Commun. 15:1993;1179 (j) Aspinall I.H., Cowley P.M., Mitchell G., Raynor C.M., Stooley R.J. J. Chem. Soc., Perkin Trans. 1. 1999;2591.
11. For the initial isolation of the acid see: (a) Morimoto K., Shimada N., Naganawa H., Takita T., Umezawa H. J. Antibiot. 34:1981;1615. For the synthesis of 2 and representative pyridazine acids see: (b) Attwood M.R., Hassall C.H., Kröhn A., Lawton G., Redshaw S. J. Chem. Soc., Perkin Trans. 1. 1986;1011 (c) Hughes P., Clardy J. J. Org. Chem. 54:1989;3260 (d) Schmidt U., Riedl B. Synthesis. 8:1993;809 (e) Nakamura Y., Ito A., Shin C. Bull. Chem. Soc. Jpn. 67:1994;2151 (f) Ciufolini M.A., Shimizu T., Swaminathan S., Xi N. Tetrahedron Lett. 38:1997;4947 (g) Xi N., Alemany L.B., Ciufolini M.A. J. Am. Chem. Soc. 120:1998;80 (h) Ciufolini M.A., Xi N. Chem. Soc. Rev. 27:1998;437 (i) Aspinall I.H., Cowley P.M., Mitchell G., Stoodley R.J. J. Chem. Soc., Chem. Commun. 15:1993;1179 (j) Aspinall I.H., Cowley P.M., Mitchell G., Raynor C.M., Stooley R.J. J. Chem. Soc., Perkin Trans. 1. 1999;2591.
12. For the initial isolation of the acid see: (a) Morimoto K., Shimada N., Naganawa H., Takita T., Umezawa H. J. Antibiot. 34:1981;1615. For the synthesis of 2 and representative pyridazine acids see: (b) Attwood M.R., Hassall C.H., Kröhn A., Lawton G., Redshaw S. J. Chem. Soc., Perkin Trans. 1. 1986;1011 (c) Hughes P., Clardy J. J. Org. Chem. 54:1989;3260 (d) Schmidt U., Riedl B. Synthesis. 8:1993;809 (e) Nakamura Y., Ito A., Shin C. Bull. Chem. Soc. Jpn. 67:1994;2151 (f) Ciufolini M.A., Shimizu T., Swaminathan S., Xi N. Tetrahedron Lett. 38:1997;4947 (g) Xi N., Alemany L.B., Ciufolini M.A. J. Am. Chem. Soc. 120:1998;80 (h) Ciufolini M.A., Xi N. Chem. Soc. Rev. 27:1998;437 (i) Aspinall I.H., Cowley P.M., Mitchell G., Stoodley R.J. J. Chem. Soc., Chem. Commun. 15:1993;1179 (j) Aspinall I.H., Cowley P.M., Mitchell G., Raynor C.M., Stooley R.J. J. Chem. Soc., Perkin Trans. 1. 1999;2591.
13. For a review concerning the use of lactam based peptidomimetics see: (a) Hanessian S., McNaughton-Smith G., Lombart H.-G., Lubell W.D. Tetrahedron. 53:1997;12789. For more recent references see: (b) Polyak F., Lubell W.D. J. Org. Chem. 63:1998;5937 (c) Curran T.P., Marcaurell L.A., O'Sullivan K.M. Org. Lett. 1:1999;1225 (d) Gosselin F., Lubell W.D. J. Org. Chem. 65:2000;2163 (e) Polyak F., Lubell W.D. J. Org. Chem. 66:2001;1171 (f) Feng Z., Lubell W.D. J. Org. Chem. 66:2001;1181.
14. For a review concerning the use of lactam based peptidomimetics see: (a) Hanessian S., McNaughton-Smith G., Lombart H.-G., Lubell W.D. Tetrahedron. 53:1997;12789. For more recent references see: (b) Polyak F., Lubell W.D. J. Org. Chem. 63:1998;5937 (c) Curran T.P., Marcaurell L.A., O'Sullivan K.M. Org. Lett. 1:1999;1225 (d) Gosselin F., Lubell W.D. J. Org. Chem. 65:2000;2163 (e) Polyak F., Lubell W.D. J. Org. Chem. 66:2001;1171 (f) Feng Z., Lubell W.D. J. Org. Chem. 66:2001;1181.
15. For a review concerning the use of lactam based peptidomimetics see: (a) Hanessian S., McNaughton-Smith G., Lombart H.-G., Lubell W.D. Tetrahedron. 53:1997;12789. For more recent references see: (b) Polyak F., Lubell W.D. J. Org. Chem. 63:1998;5937 (c) Curran T.P., Marcaurell L.A., O'Sullivan K.M. Org. Lett. 1:1999;1225 (d) Gosselin F., Lubell W.D. J. Org. Chem. 65:2000;2163 (e) Polyak F., Lubell W.D. J. Org. Chem. 66:2001;1171 (f) Feng Z., Lubell W.D. J. Org. Chem. 66:2001;1181.
16. For a review concerning the use of lactam based peptidomimetics see: (a) Hanessian S., McNaughton-Smith G., Lombart H.-G., Lubell W.D. Tetrahedron. 53:1997;12789. For more recent references see: (b) Polyak F., Lubell W.D. J. Org. Chem. 63:1998;5937 (c) Curran T.P., Marcaurell L.A., O'Sullivan K.M. Org. Lett. 1:1999;1225 (d) Gosselin F., Lubell W.D. J. Org. Chem. 65:2000;2163 (e) Polyak F., Lubell W.D. J. Org. Chem. 66:2001;1171 (f) Feng Z., Lubell W.D. J. Org. Chem. 66:2001;1181.
17. For a review concerning the use of lactam based peptidomimetics see: (a) Hanessian S., McNaughton-Smith G., Lombart H.-G., Lubell W.D. Tetrahedron. 53:1997;12789. For more recent references see: (b) Polyak F., Lubell W.D. J. Org. Chem. 63:1998;5937 (c) Curran T.P., Marcaurell L.A., O'Sullivan K.M. Org. Lett. 1:1999;1225 (d) Gosselin F., Lubell W.D. J. Org. Chem. 65:2000;2163 (e) Polyak F., Lubell W.D. J. Org. Chem. 66:2001;1171 (f) Feng Z., Lubell W.D. J. Org. Chem. 66:2001;1181.
18. For a review concerning the use of lactam based peptidomimetics see: (a) Hanessian S., McNaughton-Smith G., Lombart H.-G., Lubell W.D. Tetrahedron. 53:1997;12789. For more recent references see: (b) Polyak F., Lubell W.D. J. Org. Chem. 63:1998;5937 (c) Curran T.P., Marcaurell L.A., O'Sullivan K.M. Org. Lett. 1:1999;1225 (d) Gosselin F., Lubell W.D. J. Org. Chem. 65:2000;2163 (e) Polyak F., Lubell W.D. J. Org. Chem. 66:2001;1171 (f) Feng Z., Lubell W.D. J. Org. Chem. 66:2001;1181.
19. For modeling studies leading to predicted 'active conformation' for TRH binding to its endocrine receptor TRH-R see: (a) Marshall G.R., Gorin F.A., Moore M.L. Clarke F.H. Annual Reports in Medicinal Chemistry. Vol. 13:1978;227 Academic, New York. and references therein (b) Font, J., 'Computer-Assisted Drug Design.', Ph.D. Thesis, Washington University in St. Louis, 1986.
20. For modeling studies leading to predicted 'active conformation' for TRH binding to its endocrine receptor TRH-R see: (a) Marshall G.R., Gorin F.A., Moore M.L. Clarke F.H. Annual Reports in Medicinal Chemistry. Vol. 13:1978;227 Academic, New York. and references therein (b) Font, J., 'Computer-Assisted Drug Design.', Ph.D. Thesis, Washington University in St. Louis, 1986.
21. For partially constrained analogs of TRH see: (a) Rutledge L.D., Perlman J.H., Gershengorn M.C., Marshall G.R., Moeller K.D. J. Med. Chem. 39:1996;1571-1574 (b) Laakkonen L., Li W., Perlman J.H., Guarnieri F., Osman R., Moeller K.D., Gershengorn M.C. Mol. Pharmacol. 49:1996;1092-1096 (c) Li W., Moeller K.D. J. Am. Chem. Soc. 118:1996;10106. For fully constrained analogs see: (d) 'Thyrotropin Releasing Hormone Analogs: A Building Block Approach to the Construction of Tetracyclic Peptidomimetics' Chu W., Perlman J.H., Gershengorn M.C., Moeller K.D. Bioorg. Med. Chem. Lett. 8:1998;3093.
22. For partially constrained analogs of TRH see: (a) Rutledge L.D., Perlman J.H., Gershengorn M.C., Marshall G.R., Moeller K.D. J. Med. Chem. 39:1996;1571-1574 (b) Laakkonen L., Li W., Perlman J.H., Guarnieri F., Osman R., Moeller K.D., Gershengorn M.C. Mol. Pharmacol. 49:1996;1092-1096 (c) Li W., Moeller K.D. J. Am. Chem. Soc. 118:1996;10106. For fully constrained analogs see: (d) 'Thyrotropin Releasing Hormone Analogs: A Building Block Approach to the Construction of Tetracyclic Peptidomimetics' Chu W., Perlman J.H., Gershengorn M.C., Moeller K.D. Bioorg. Med. Chem. Lett. 8:1998;3093.
23. For partially constrained analogs of TRH see: (a) Rutledge L.D., Perlman J.H., Gershengorn M.C., Marshall G.R., Moeller K.D. J. Med. Chem. 39:1996;1571-1574 (b) Laakkonen L., Li W., Perlman J.H., Guarnieri F., Osman R., Moeller K.D., Gershengorn M.C. Mol. Pharmacol. 49:1996;1092-1096 (c) Li W., Moeller K.D. J. Am. Chem. Soc. 118:1996;10106. For fully constrained analogs see: (d) 'Thyrotropin Releasing Hormone Analogs: A Building Block Approach to the Construction of Tetracyclic Peptidomimetics' Chu W., Perlman J.H., Gershengorn M.C., Moeller K.D. Bioorg. Med. Chem. Lett. 8:1998;3093.
24. For partially constrained analogs of TRH see: (a) Rutledge L.D., Perlman J.H., Gershengorn M.C., Marshall G.R., Moeller K.D. J. Med. Chem. 39:1996;1571-1574 (b) Laakkonen L., Li W., Perlman J.H., Guarnieri F., Osman R., Moeller K.D., Gershengorn M.C. Mol. Pharmacol. 49:1996;1092-1096 (c) Li W., Moeller K.D. J. Am. Chem. Soc. 118:1996;10106. For fully constrained analogs see: (d) 'Thyrotropin Releasing Hormone Analogs: A Building Block Approach to the Construction of Tetracyclic Peptidomimetics' Chu W., Perlman J.H., Gershengorn M.C., Moeller K.D. Bioorg. Med. Chem. Lett. 8:1998;3093.
25. Beal L.M., Liu B., Chu W., Moeller K.D. Tetrahedron. 56:2000;10113.
26. To find the lowest energy ground state conformation of the molecule, a conformation distribution search was run at the molecular mechanics level. The most favorable structures were then submitted to an equilibrium geometry calculation at the AM1 semi-empirical level. To find the energy level for the transition state, a transition geometry calculation was run at the AM1 level. This resulted in a structure with one imaginary vibration above 100 Hz. This vibration was animated in order to show the nitrogen vibrating up and down in a manner consistent with the motion leading to inversion. At this point, a single point energy calculation at the 3-21G* ab initio level was run for both the lowest energy conformation and the transition state structure. The energy difference for the two conformations was taken as the barrier for the inversion.
27. For TRH analogs constrained with a seven-membered ring lactam see Ref. 6.
28. Hehre W.J., Shusterman A.J., Huang W.W. A Laboratory Book of Computational Organic Chemistry. 1985;Wavefunction. pp 85.
29. For the synthesis of analogs having six and seven-membered ring lactams fused to the pyridazine acid ring see Ref. 2b. For a review concerning the pharmacology of analogs having a seven-membered ring lactam fused to the pyridazine acid (such a the angiotensin converting enzyme inhibitor cilazapril) see: Belz G.G., Breithaupt K., Erb K. J. Cardiovasc. Pharmacol. 24:(suppl. 2):1994;14.
30. Kazmaier U., Krebs A. Angew. Chem. Int. Ed. Eng. 34:1995;2012.
31. Chu W., Moeller K.D. Tetrahedron Lett. 40:1999;7939.