Geometrically and conformationally restrained cinnamoyl compounds as inhibitors of HIV-1 integrase: Synthesis, biological evaluation, and molecular modeling

Journal of Medicinal Chemistry

Volumn 41, Issue 21, 1998, Pages 3948-3960

  Artico, Marino ^a   Santo, Roberte Di ^a   Costi, Roberta ^a   Novellino, Ettore ^b   Greco, Giovanni ^c   Massa, Silvio ^d   Tramontano, Enzo ^e   Marongiu, Maria E ^e   De Montis, Antonella ^e   Colla, Paolo La ^e  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITY OF SALERNO   (Italy)

^c UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^d UNIVERSITY OF SIENA   (Italy)

^e UNIVERSITY OF CAGLIARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CURCUMIN; FLAVONE DERIVATIVE; INTEGRASE INHIBITOR; QUERCETIN; RNA DIRECTED DNA POLYMERASE;

ARTICLE; CURCUMA LONGA; DRUG CONFORMATION; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; ENZYME ASSAY; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; MOLECULAR MODEL; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

ANTI-HIV AGENTS; ANTINEOPLASTIC AGENTS; CELL DIVISION; CINNAMATES; CRYSTALLOGRAPHY, X-RAY; HIV INTEGRASE INHIBITORS; HIV-1; HUMANS; MODELS, MOLECULAR; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED; VIRUS REPLICATION;

EID: 15144355755     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9707232     Document Type: Article

References (50)

1. Artico, M. Nonnucleoside anti-HIV-1 Reverse Tranacriptase Inhibitors (NNRTIs): A Chemical Survey from Lead Compounds to Selected Drugs for Clinical Trials. Farmaco 1996, 51, 305- 331
2. Appell, K.; Clare, M.; Pettit, S. C.; Michael, S. F.; Swanstrom, R.; Moore, M. C.; Dreyer, G. B.; Erickson, J. W. Therapeutic Approaches to HIV. Perspect. Drug Discovery Des. 1993, 1, 23- 128.
3. De Clercq, E. Toward Improved anti-HIV Chemotherapy: Therapeutic Strategies for Intervention with HIV Infections. J. Med. Chem. 1995, 38, 2491-2617.
4. La Femina, R. L.; Schneider, C. L.; Robbins, H. L.; Callahan, P. L.; LeGrow, K.; Roth, E.; Schleif, W. A.; Emini, E. A. Requirement of Active Human Immunodeficiency Virus Type 1 Integrase Enzyme for Productive Infection of Human T-Lymphoid Cells. J. Virol. 1992, 66, 7414-7419.
5. Sakai, H.; Kawamura, M.; Sakuragi, J.; Sakuragi, S.; Shibata, R.; Ishimoto, A.; Ono, N.; Ueda, S.; Adachi, A. Integration is Essential for Efficient Gene Expression of Human Immunodeficiency Virus type 1. J. Virol. 1993, 67, 1169-1174.
6. Brown, P. O.; Bowerman, B.; Varmus, H. F.; Bishop, J. M. Retroviral Integration: Structure of the Initial Covalent Product and its Precursor, and a Role for the Viral Integrase Protein. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 2525-2529.
7. Bushman, F. D.; Fujiwara, T.; Craigie, R. Retroviral DNA Integration Directed by HIV Integration Protein in Vitro. Science 1990, 249, 1555-1558.
8. Fesen, M. K.; Pommier, Y.; Leteurtre, F.; Hiroguchi, S.; Young, J.; Kohn, K. W. Inhibition of HIV-1 Integrase by Flavones, Caffeic Acid Phenethyl Ester (CAPE) and Related Compounds. Biochem. Pharmacol. 1994, 48, 595-608.
9. Burke, T. R., Jr.; Fesen, M. R.; Mazumder, A.; Wang, Y.; Carothers, A. M.; Grunberger, D.; Driscoll, J.; Khon, K.; Pommier, Y. Hydroxylated Aromatic Inhibitors of HIV-1 Integrase, J. Med. Chem. 1995, 35, 4171-4178.
10. LaFemina, R. L.; Graham, P. L.; LeGrow, K.; Hastings, J. C.; Wolfe, A.; Young, S. D.; Emini, E. A.; Hazuda, D. J. Inhibition of Human Immunodeficiency Virus Integrase by Bis-Catechols. Antimicrob, Agents Chemother. 1995, 39, 320-324.
11. Mazumder, A.; Raghavan, K.; Weistein, J.; Kohn, K. W.; Pommier, Y. Inhibition of Human Immunodeficiency Virus Type-1 Integrase by Curcumin. Biochem. Pharmacol. 1995, 49, 1165- 1170.
12. Mazumder, A.; Gazit, A.; Levitzki, A.; Nicklaus, M.; Yung, J.; Kohlhagen, G.; Pommier, Y. Effects of Tyrphostins, Protein Kinase Inhibitors, on Human Immunodeficiency Virus Type 1 Integrase. Biochemistry 1995, 34, 15111-15122.
13. Eich, E.; Pertz, H.; Kaloga, M.; Schultz, J.; Fesen, M. R.; Mazumder, A.; Pommier, Y. (-)-Arctigenin as a Lead Structure for Inhibitors of Human Immunodeficiency Virus Type-1 Integrase. J. Med. Chem. 1996, 39, 86-95.
14. Robinson, W. E., Jr.; Reinecke, M. G.; Abdel-Malek, S.; Jia, Q.; Chow, S. A. Inhibitors of HIV-1 Replication that Inhibit HIV Integrase. Proc. Nad. Acad. Sci. U.S.A. 1996, 93, 6326-6331.
15. Li, C. J.; Zhang, L. J.; Dezube, B. J.; Crumpacker, C. S.; Pardee, A. B. Three Inhibitors of Type 1 Human Immunodeficiency Virus Long Terminal Repeat-Directed Gene Expression and Virus Replication. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 1839-1842.
16. Dyda, F.; Hickman, A. B.; Jenkins, T. M.; Engelman, A.; Craigie, R.; Davies, D. R. Crystal Structure of the Catalytic Domain of HIV-1 Integrase: Similarity to Other Polynucleotidyl Transferases. Science 1994, 266, 1981-1986.
17. Bernstein, F. C.; Koetzle, T. F.; Williams, G. J. B.; Meyer, E. F., Jr.; Brice, M. D.; Rodgers, J. R.; Kennard, O.; Shimanouchi, T.; Tasumi, T. The Protein Data Bank: A Computer Based Archival File for Macromolecular Structures. J. Mol. Biol. 1977, 112, 535-542.
18. Babu, K. V. D.; Rajasekharan, K. N. Simplified Condition for Synthesis of Curcumin I and Other Curcuminoids. OPPI Briefs 1994, 26, 674-677.
19. Severi, F.; Costantino, L.; Benvenuti, S.; Vampa, G.; Mucci, A. Synthesis and Description of Chalcone-like Compounds, Inhibitors of Aldose Reductase. Med. Chem. Res. 1996, 6, 128-136.
20. Oosawa, T.; Ochi, H. Jpn. Kokai Tokkyo Koho JP 07,206,763 [95,206,753]; Chem. Abstr. 1996, 124, 8511s.
21. Zhao, H.; Neamati, N.; Mazumder, A.; Sunder, S.; Pommier, Y.; Burke, T. R., Jr. Arylamide Inhibitors of HIV-1 Integrase. J. Med. Chem. 1997, 40, 1186-1194.
22. Cushman, M.; Sherman, P. Inhibition of HIV-1 Integration Protein by Aurintricarboxylic Acid Monomers, Monomer Analogues and Polymer Fractions. Biochem. Biophys. Res. Commun. 1992, 185, 85-90.
23. Engelman, A.; Mizouchi, K.; Craigle, R. HIV-1 DNA Integration Mechanism of Viral DNA Cleavage and DNA Strand Transfer. Cell 1991, 67, 1211-1221.
24. Ono, K.; Nakane, H.; Fukushima, M.; Chermann, J.-C.; Barré- Sinoussi, F. Differential Inhibitory Effects of Various Flavonoids on the Activities of Reverse Transcriptase and Cellular DNA and RNA Polymerases. Eur. J. Biochem. 1990, 190, 469-476.
25. Chu, S. C.; Hsiech, Y. S.; Lin, J. Y. Inhibitory Effects of Flavonoids on Moloney Murine Leukemia Virus Reverse Transcriptase Activity. J. Nat. Prod. 1992, 55, 179-183.
26. SYBYL Molecular Modeling System (version 6.2), Tripos Assoc., St. Louis, MO.
27. Zhao, H.; Neamati, N.; Hong, H.; Mazumder, A.; Wang, S.; Sunder, S.; Milne, G. W. A.; Pommier, Y.; Burke, T. R., Jr. Coumarin-Based Inhibitors of HIV-1 Integrase. J. Med. Chem. 1997, 40, 242-249,
28. Rossi, M.; Rickles, L. F.; Halpin, W. A. The Crystal and Molecular Structure of Quercetin: a Biologically Active and Naturally Occurring Flavonoid. Bioorg. Chem. 1986, 14, 55- 69.
29. Sui, Z.; Salto, R.; Li, J.; Craik, C.; Ortiz de Montellano, P. R. Inhibition of the HIV-1 and HIV-2 Proteases by Curcumin and Curcumin Boron Complexes. Bioorg. Med. Chem. 1993, 1, 415- 422.
30. Clark, M.; Cramer, R. D., III; Van Opdenbosch, N. Validation of the General Purpose Tripos 5.2 Force Field. J. Comput Chem. 1989, 10, 982-1012.
31. Mazumder, A.; Neamati, N.; Sunder, S.; Schulz, J.; Pertz, H.; Eich, E.; Pommier, Y. Curcumin analogues with altered potencies against HIV-1 integrase as probes for biochemical mechanisms of drug action. J. Med. Chem. 1997, 40, 3057-3063.
32. Burckhalter, J. H.; Dixon, W. D.; Black, M.; Westland, R. D.; Werbel, L. M.; DeWald, H. A.; Dice, J. R.; Rodney, G.; Kaump, D. H. 2-(2-Pyridyl)-1,2-diaryl Alkanols as Hypocholesteremic Agents. J. Med. Chem. 1967, 10, 565-575.
33. Samdahl, B. Diveratrylidene and Divanillydene Compounds of Cyclohexanone, Comprising Several New Indicators. J. Pharm. Chim. 1928, 7, 162-173.
34. Gasteiger, J.; Marsili, M. Iterative Partial Equalization of Orbital Electronegativity. Tetrahedron 1980, 36, 3219-3228.
35. Purcel, V. P.; Singer, J. A. A Brief Review and Table of Semiepirical Parameters Used in the Hückel Molecular Orbital Method. J. Chem. Eng. Data 1967, 12, 235-246.
36. Head, J.; Zerner, M. C. A Broyden-Fletcher-Goldfarb-Shanno Optimization Procedure for Molecular Geometries. Chem. Phys. Lett. 1985, 122, 264-274.
37. Pauwels, R.; Balzarini, J.; Baba, M.; Snoeck, R.; Schols, D.; Herdewijn, P.; Desmyster, J.; De Clercq, E. Rapid and Automated Tetrazolium-Based Assay for the Detection of anti-HIV Compounds. J. Virol. Methods 1988, 20, 309-321.
38. Tomassini, J.; Davies, M. E.; Amstrong, M. E.; Hastings, J.; Hazuda, D.; Lewis, J.; McClemens, W.; Wolfe, A.; Selnick, H.; Baldwin, J.; Bourgeois, M.; Ponticello, G.; Radilowski, E.; Smith, G.; Tebben, A. Inhibition of the cap-dependent endonuclease of influenza virus by 4-substituted-2,4-dioxobutanoic acid compounds. Antimicrob. Agents Chemother. 1994, 38, 2827-2837.
39. Lee, K. H.; Imakura, Y.; Haurna, M.; Beers, S. A.; Thurston, L. S.; Dai, H. J.; Chen, C. H. Antitumor Agent 107. New Cytotoxic 4-Alkylamino Analogues of 4′-Demethyl-epipodophyllotoxin as Inhibitors of Human DNA Topoisomerase II. J. Nat Prod. 1989, 52, 606-613.
40. Samdahl, B. Some New Indicators, Derivatives of Cyclohexanone. J. Pharm. Chim. 1930, 11, 8-19.
41. Samdhal, B.; Hansen, B. Condensation of Cyclopentanone with Phenol Aldehydes. J. Pharm. Chim. 1928, 7, 162-173.
42. Ionescu, M. V. New Reaction for Aromatic Aldehydes. Bull. Soc. Chim. 1930, 47, 210-214.
43. Haworth, R. D.; Lamberton, A. H. Some Derivatives of Catechol and Pyrogallol. II. J. Chem. Soc. 1946, 1003-1005.
44. Glaser, E.; Tramer, E. Condensation Product of Vanillin and Salicylaldehyde with Acetone and the Mechanism of this Condensation. J. Prakt. Chem. 1927, 116, 331-346.
45. McGookin, A.; Sinclair, D. J. Isomerism of the Styryl Alkyl Ketones. IV. 4-Hydroxy- and some Derivatives of 2-Hydroxystyryl Alkyl Ketones. J. Chem. Soc. 1928, 1170-1177.
46. Klinke, P.; Gibian, H. Chalcones. Chem. Ber. 1961, 94, 26-38.
47. Dziedzic, S. Z.; Hudson, B. J. F. Polyhydroxy Chalcones and Flavanones as Antioxidants for Edible Oils. Food Chem. 1983, 12, 205-212.
48. Geissman, T. A.; Clinton, R. O. Flavanones and Related Compounds. I. The Preparation of Polyhydroxychalcones and Flavanones. J. Am. Chem. Soc. 1946, 68, 697-700.
49. Jentzsch, K.; Spiegel, P.; Kamitz, R. Qualitative and Quantitative Studies of Curcuma Dyes in Different Zingiberaceae Drugs. 2. Quantitative studies. Sci. Pharm. 1970, 38, 50-58.
50. Pabon, H. J. J. A Synthesis of Curcumin and Related Compounds. Recl. Trav. Chim. Pays Bas 1964, 83, 379-386.