Synthesis, biological activity and modelling studies of two novel anti HIV PR inhibitors with a thiophene containing hydroxyethylamino core

Tetrahedron

Volumn 61, Issue 27, 2005, Pages 6580-6589

  Bonini, Carlo ^a   Chiummiento, Lucia ^a   De Bonis, Margherita ^a   Funicello, Maria ^a   Lupattelli, Paolo ^a   Suanno, Gerardina ^a   Berti, Federico ^b   Campaner, Pietro ^b  

^a UNIVERSITY OF BASILICATA   (Italy)

^b UNIVERSITY OF TRIESTE   (Italy)

Author keywords

Biological activity; HIV PR inhibitors; Hydroxyethylamino core; Thiophene

Indexed keywords

2 [2' HYDROXY 3' (3 HYDROXY 2 METHYLBENZOYLAMINO) 3' (THIOPHEN 2 YL)PROPYL]DECAHYDROISOQUINOLINE 3 CARBOXYLIC ACID TERT BUTYLAMIDE; ACRYLIC ACID DERIVATIVE; ALCOHOL; ASPARTIC PROTEINASE INHIBITOR; ESTER; N1 [3 (3 TERT BUTYLCARBAMOYLDECAHYDROISOQUINOLIN 2 YL) 2 HYDROXY 1 THIOPHEN 2 YLPROPYL] 2 [(QUINOLINE 2 CARBONYL)AMINO]SUCCINAMIDE; NELFINAVIR; SAQUINAVIR; SODIUM AZIDE; SULFITE; THIOPHENE ACRYLATE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; COMMERCIAL PHENOMENA; DIHYDROXYLATION; DRUG ACTIVITY; DRUG SCREENING; DRUG SYNTHESIS; DRUG UTILIZATION; MOLECULAR MODEL; PRECURSOR; PRIORITY JOURNAL; REDUCTION; RING OPENING;

EID: 20444471585     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.04.048     Document Type: Article

References (62)

1. A.K. Ghosh, G. Bilcer, and G. Schiltz Synthesis 15 2001 2203
2. A. Brik, and C.-H. Wong Org. Biomol. Chem. 1 2003 5
3. A. Wlodawer, and A. Gustchina Biochim. Biophys. Acta 1477 2000 16
4. A.G. Tomasselli, and R.L. Heinrikson Biochim. Biophys. Acta 1477 2000 189
5. R.E. Babine, and S.L. Bender Chem. Rev. 97 1997 1367
6. A.S. Ripka, K.A. Satyshur, R.S. Bohacek, and D.H. Rich Org. Lett. 3 2001 2309
7. A. Giannis, and T. Kolter Angew. Chem., Int. Ed. Engl. 32 1993 1244
8. J. Gante Angew. Chem., Int. Ed. Engl. 33 1994 1699
9. D. Leug, G. Abbenante, and G. Schiltz J. Med. Chem. 43 2000 305
10. C. Corral, J. Lissavetzky, I. Manzanares, V. Darias, M.A. Exposito-Orta, J.A.M. Conde, and C.C. Sanchez-Mateo Bioorg. Med. Chem. 7 1999 1349
11. A. Zhang, G. Zhou, S.-B. Rong, K.M. Johnson, M. Zang, and A.P. Kozikowski Bioorg. Med. Chem. Lett. 12 2002 993
12. F.M. Uckun, S. Pendergrass, D. Maher, D. Zhu, L. Tuel-Ahlgren, C. Mao, and T.K. Venkatachalam Bioorg. Med. Chem. Lett. 9 1999 3411
13. In this paper the authors described the effects on the substitution of the oxyalkyl and oxyaryl P1/P1′ groups with thioalkyl and thioaryl groups. A. Muhlman, B. Classon, A. Haliberg, and B. Samuelsson J. Med. Chem. 44 2001 3402
14. For reported syntheses of Nelfinavir see: (a) S.W. Kaldor, V.J. Kalish, J.F. Davies II, B.V. Shetty, J.E. Fritz, K. Appelt, J.A. Burgess, K.M. Campanale, N.Y. Chirgadze, D.K. Clawson, B.A. Dressman, S.D. Hatch, D.A. Khalil, M.B. Kosa, P.P. Lubbehusen, M.A. Muesing, A.K. Patick, S.H. Reich, K.S. Su, and J.H. Tatlock J. Med. Chem. 40 1997 3979
15. D.L. Rieger J. Org. Chem. 62 1997 8546
16. T. Inaba, A.G. Birchler, Y. Yamada, S. Sagawa, K. Yokota, K. Ando, and I. Uchida J. Org. Chem. 63 1998 7582
17. S.E. Zook, J.K. Busse, and B.C. Borer Tetrahedron Lett. 41 2000 7017
18. T. Inaba, Y. Yamada, H. Abe, S. Sagawa, and H. Cho J. Org. Chem. 65 2000 1623
19. K.F. Albizati, S. Babu, A. Birchler, J.K. Busse, M. Fugett, A. Grubbs, A. Haddach, M. Pagan, B. Potts, T. Remarchuk, D. Rieger, R. Rodriguez, J. Shanley, R. Szendroi, T. Tibbetts, K. Whitten, and B.V. Borer Tetrahedron Lett. 42 2001 6481
20. D. Ma, B. Zou, W. Zhu, and H. Xu Tetrahedron Lett. 43 2002 8511
21. M. Ikunaka, J. Matsumoto, Y. Fujima, and Y. Hirayama Org. Proc. Res. Dev. 6 2002 49
22. For reported syntheses of Saquinavir see: (a) W.J. Thompson, A.K. Ghosh, M.K. Holloway, H.Y. Lee, P.M. Munson, J.E. Schwering, J. Wai, P.L. Darke, J. Zugay, E.A. Emini, W.A. Schleif, J.R. Huff, and P.S. Anderson J. Am. Chem. Soc. 115 1993 801
23. K.E.B. Parkes, D.J. Bushnell, P.H. Crackett, S.J. Dunsdon, A.C. Freeman, M.P. Gunn, R.A. Hopkins, R.W. Lambert, J.A. Martin, J.H. Merrett, S. Redshaw, W.C. Spurden, and G.J. Thomas J. Org. Chem. 59 1994 3656
24. A. Fassler, G. Bold, H.-G. Capraro, R. Cozens, J. Mestan, B. Poncioni, J. Rosel, M. Tintelnot-Blomley, and M. Lang J. Med. Chem. 39 1996 3203
25. W. Gohring, S. Gokhale, H. Hilpert, F. Roessler, M. Schlageter, and P. Vogt Chimia 50 1996 532
26. A.K. Ghosh, K.A. Hussain, and S. Fidanze J. Org. Chem. 62 1997 6080
27. M.K. Tay, E. About-Joudet, N. Callignon, M.P. Teulade, and P. Savignac Synth. Commun. 18 1988 1349
28. A. Kosakara, T. Izumi, and T. Ogihara J. Heterocycl. Chem. 26 1989 597
29. R. Rossi, A. Carpita, M. Ciofalo, and V. Lippolis Tetrahedron 47 1991 8443
30. K. Guncheal, L. Don Gyu, and C. Sukbok Bull. Korean Chem. Soc. 22 2001 943
31. H.C. Kolb, M.S. VanNieuwenhze, and K.B. Sharpless Chem. Rev. 94 1994 2483
32. For preliminary communication of part of this work see: C. Bonini, L. Chiummiento, M. De Bonis, M. Funicello, and P. Lupattelli Tetrahedron Lett. 45 2004 2797
33. C. Bonini, M. D'Auria, and P. Fedeli Tetrahedron Lett. 43 2002 3813
34. H.S. Byun, L. He, and R. Bittman Tetrahedron 56 2000 7051
35. C. Xiong, W. Wang, C.J. Cai, and V.J. Hruby J. Org. Chem. 67 2002 1399
36. A. Solladié-Cavallo, P. Lupattelli, C. Bonini, and M. De Bonis Tetrahedron Lett. 44 2003 5075
37. S. Superchi, M. Contursi, and C. Rosini Tetrahedron 54 1998 11247
38. J.-N. Denis, A.E. Green, A.A. Serra, and M.-J. Luche J. Org. Chem. 51 1986 11247
39. Y. Hamada, M. Shibata, T. Sugiura, S. Kato, and T. Shioiri J. Org. Chem. 52 1987 1252
40. A.P. Kozikowski, K. Sato, A. Basu, and J.S. Lazo J. Am. Chem. Soc. 111 1989 6228
41. S. Saito, T. Ishikawa, A. Kuroda, K. Koga, and T. Moriwake Tetrahedron 48 1992 4067
42. F.D. Bellamy, M. Bondoux, and P. Dodey Tetrahedron Lett. 31 1990 7323
43. A. Pommier, J.M. Pons, and P.J. Kocienski J. Org. Chem. 60 1995 7334
44. The compound 16 was obtained with same yield (67%) starting from both compounds 15a and 15b (see Section 8).
45. M.D. Varney, K. Appelt, V. Kalish, M. Rami Reddy, J. Tatlock, C.L. Palmer, W.H. Romines, B.-W. Wu, and L. Musick J. Med. Chem. 37 1994 2274
46. A.D. Abell, and G.J. Foulds J. Chem. Soc., Perkin Trans 1 1997 2475
47. B.C.H. May, and A.D. Abell J. Chem. Soc., Perkin Trans 1 2002 172
48. A. Tossi, F. Benedetti, S. Norbedo, D. Skrbec, F. Berti, and D. Romeo Bioorg. Med. Chem. 11 2003 4719 4727
49. D. Skrbec, and D. Romeo Biochem. Biophys. Res. Commun. 297 2002 1350
50. A. Tossi, I. Bonin, N. Antcheva, S. Norbedo, F. Benedetti, S. Miertus, A.C. Nair, T. Maliar, F. Dal Bello, G. Palù, and D. Romeo Eur. J. Biochem. 267 2000 1715
51. S. Cha Biochem. Pharmacol. 24 1975 2177
52. P.O. Markgren, M. Hämäläinen, and U.H. Danielson Anal. Biochem. 279 2000 71
53. W.D. Cornell, P. Cieplak, C.I. Bayly, I.R. Gould, K.M. Merz Jr., D.M. Ferguson, D.C. Spellmeyer, T. Fox, J.W. Caldwell, and P.A. Kollman J. Am. Chem. Soc. 117 1995 5179
54. S. Geremia, and M. Calligaris J. Chem. Soc., Dalton Trans. 1997 1541
55. Gaussian 03, Revision A.1, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr., J. A.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; and Pople, J. A.; Gaussian, Pittsburgh PA, 2003.
56. M. Orozoco, C.A. Laughton, P. Herzyk, and S. Neidle J. Biomol. Struct. Dyn. 8 1990 359
57. R.S. Judson, and H. Rabitz Phys. Rev. Lett. 68 1992 1500
58. Z. Chen, Y. Yan, Y. Li, D.B. Olsen;, H.B. Schock, B.B. Galvin, B. Dorsey, and L.C. Kuo Acta Crystallogr. D 56 2000 38
59. S.W. Kaldor, V.J. Kalish, J.F. Davies II, B.V. Shetty, J.E. Fritz, K. Appelt, J.A. Burgess, K.M. Campanale, N.Y. Chirgadze, D.K. Clawson, B.A. Dressman, S.D. Hatch, D.A. Khalil, M.B. Kosa, P.P. Lubbehusen, M.A. Muesing, A.K. Patick, S.H. Reich, K.S. Su, and J.H. Tatlock J. Med Chem. 40 1997 3979
60. P. Carloni, U. Rothlisberger, and M. Parrinello Acc. Chem. Res. 35 2002 455
61. S. Piana, D. Sebastiani, P. Carloni, and M. Parrinello J. Am. Chem. Soc. 123 2001 8730
62. M. Levit, and S. Lifson J. Mol. Biol. 46 1969 269