Synthesis and structure-activity relationships of 2- pyrazinylcarboxamidobenzoates and β-ionylideneacetamidobenzoates with retinoidal activity

Journal of Medicinal Chemistry

Volumn 41, Issue 16, 1998, Pages 3062-3077

  Jones, Paul ^a   Villeneuve, Gérald B ^a   Fei, Chengpei ^a   DeMarte, Josie ^a   Haggarty, Allison J ^a   Nwe, Khin Than ^a   Martin, Deborah A ^a   Lebuis, Anne Marie ^a   Finkelstein, Joshua M ^a   Gour Salin, Barbara J ^a   Chan, Tak Hang ^a   Leyland Jones, Brian R ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRAZINYLCARBOXAMIDOBENZOIC ACID; 4 [2 (5,6,7,8 TERAHYDRO 5,5,8,8 TETRAMETHYLQUINOXALYL)CARBOXAMIDO]BENZOIC ACID; 4 [3 METHYL 5 (2',6',6' TRIMETHYL 1' CYCLOHEXEN 1' YL) PENTADIENAMIDO]BENZOIC ACID; BENZOIC ACID DERIVATIVE; BETA IONYLIDENEACETAMIDOBENZOIC ACID; RETINOIC ACID RECEPTOR; RETINOID; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CELL DIFFERENTIATION; CELL STRAIN HL 60; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

ANIMALS; BENZOATES; CELL DIFFERENTIATION; CRYSTALLOGRAPHY, X-RAY; CYCLOHEXANES; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MICE; MODELS, MOLECULAR; MOLECULAR CONFORMATION; QUINOXALINES; RETINOIDS; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 15144358849     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9801354     Document Type: Article

References (69)

1. Sporn, M. B., Roberts, A. B., Goodman, D. S., Eds. The Retinoids: Biology, Chemistry, and Medicine, 2nd ed.; Raven Press, Ltd.: New York, 1994.
2. Beere, H. M.; Hickman, J. A. Differentiation: A Suitable Strategy for Cancer Chemotherapy? Anti-Cancer Drug Des. 1993, 8, 299-322.
3. Orfanos, C. E.; Ehlert, R.; Gollnick, H. The Retinoids. A Review of Their Clinical Pharmacology and Therapeutic Use. Drugs 1987, 34, 459-503.
4. Smith, M. A.; Parkinson, D. R.; Cheeson, B. D.; Friedman, M. A. Retinoids in Cancer Therapy. J. Clin. Oncol 1992, 10, 839-864.
5. Vokes, E. E.; Weichselbaum, R. R.; Lippman, S. M.; Hong, W. K. Head and Neck Cancer. N. Engl. J. Med 1993, 328, 184-194.
6. Huang, M.; Ye, Y.; Chen, S.; Chai, J.; Lu, J.; Zhoa, L.; Gu, L.; Wang, Z. Use of all-trans-Retinoic Acid in the Treatment of Acute Promyelocytic Leukemia. Blood 1988, 72, 567-572.
7. Castaigne, S.; Chomienne, C.; Daniel, M. T.; Ballerni, P.; Berger, R.; Fenaux, P.; Dogos, L. All-trans Retinoic Acid as a Differentiation Therapy for Acute Promyelocytic Leukemia. I. Clinical Results. Blood 1990, 76, 1704-1709.
8. Warrell, R. P., Jr.; Frankel, S. R.; Miller, W. H., Jr.; Scheinberg, D. A.; Itri, L. M.; Hittelman, W. N.; Vyas, R.; Andreeff, M.; Tafuri, A.; Jakubowski, A.; Gabrilove, J.; Gordon, M. S.; Dmitrovsky, E. Differentiation Therapy of Acute Promyelocytic Leukemia with Tretinoin (all-trans-Retinoic Acid). N. Engl. J. Med. 1991, 324, 1385-1393.
9. Stone, R. M.; Mayer, R. J. The Unique Aspects of Acute Promyelocytic Leukemia. J. Clin. Oncol 1992, 8, 1913-1921.
10. Gilchrest, B. A. Retinoids and the Skin. Nutrition Rev 1994, 52, 299-310.
11. Huber, M. H.; Hong, W. K. Biology and Chemoprevention of Head and Neck Cancer. Curr. Prob. Cancer 1994, 18, 81-140.
12. Verschoore, M.; Bouclier, M.; Czernielewski, J.; Hensby, C. Topical Retinoids. Their Uses in Dermatology. Dermatol. Clin. 1993, 11, 107-115.
13. Lippman, S. M.; Kavanagh, J. J.; Peredes-Espinosa, M.; Deigadillo-Madrueno, F.; Pafredes-Casillas, P.; Hong, W. K.; Holdener, E.; Krakoff, I. H. 13-cis-Retinoic Acid plus Interferon-α-2a: Highly Active Systemic Therapy for Squamous Cell Carcinoma of the Cervix. J. Natl. Cancer Inst 1992, 84, 241-245.
14. Lippman, S. M.; Kavanagh, J. J.; Paredes-Espinosa, M.; Deigadillo-Madrueno, F.; Pafredes-Casillas, P.; Hong, W. K.; Massimini, G.; Holdener, E.; Krakoffet, I. H. 13-cis-Retinoic Acid plus Interferon-α-2a in Locally Advanced Squamous Cell Carcinoma of the Cervix. J. Natl. Cancer Inst 1993, 85, 499-500.
15. Stunnenberg, H. G. Mechanisms of Transactivation by Retinoic Acid Receptors. BioEssays 1993, 15, 309-315.
16. Pemrick, S. M.; Lucas, D. A.; Grippo, J. F. The Retinoid Receptors. Leukemia 1994, 8, 1797-1806.
17. Leid, M.; Kastner, P.; Chambon, P. Multiplicity Generates Diversity in the Retinoic Acid Signaling Pathways. Trends Biochem. Sci 1992, 17, 427-433.
18. Fanjul, A.; Dawson, M. I.; Hobbs, P. D.; Jong, L.; Cameron, J. F.; Harlev, E.; Graupner, G.; Lu, X.-P.; Pfahl, M. A New Class of Retinoids with Selective Inhibition of AP-1 Inhibits Proliferation. Nature 1994, 372, 107-111.
19. Nagpal, S.; Athanikar, J.; Chandraratna, R. A. S. Separation of Transactivation and API Antagonism Functions of Retinoic Acid Receptor α. J. Biol. Chem 1995, 270, 923-927.
20. Charpentier, B.; Bernardon, J.-M.; Eustache, J.; Millois, G.; Martin, B.; Michel, S.; Shroot, B. Synthesis, Structure-Activity Relationships, and Biological Activities of Ligands Binding to Retinoic Acid Receptor Subtypes. J. Med. Chem 1995, 38, 4993-5006.
21. Dawson, M. I.; Jong, L.; Hobbs, P. D.; Cameron, J. F.; Chao, W., Pfahl, M.; Lee, M.-O.; Shroot, B.; Pfahl, M. Conformational Effects on Retinoid Receptor Selectivity. 2. Effects of Retinoid Bridging Group on Retinoid X Receptor Activity and Selectivity. J. Med. Chem 1995, 38, 3368-3383.
22. Boehm, M. F.; Zhang, L.; Zhi, L.; McClung, M. R.; Berger, E.; Wagoner, M.; Mars, D. E.; Suto, C. U.; Davies, P. J. A.; Heyman, R. A.; Nadzan, A. M. Design and Synthesis of Potent Retinoid X Receptor Selective Ligands that Induce Apoptosis in Leukemia Cells. J. Med. Chem 1995, 38, 3146-3155.
23. Koch, S. S. C.; Dardashti, L. J.; Hebert, J. J.; White, S. K.; Croston, G. E.; Flatten, K. S.; Heyman, R. A.; Nadzan, A. M. Identification of the First Retinoid X Receptor Homodimer Antagonist. J. Med. Chem 1996, 39, 3229-3234.
24. Beard, R. L.; Colon, D. F.; Song, T. K; Davies, P. J. A.; Kochhar, D. M.; Chandraratna, R. A. S. Synthesis and Structure-Activity Relationships of Retinoid X Receptor Selective Diaryl Sulfide Analogues of Retinoic Acid. J. Med. Chem 1996, 39, 3556-3563.
25. Yu, K.-L.; Spinazze, P.; Ostrowski, J.; Currier, S. J.; Pack, E. J.; Hammer, L.; Roalsvig, T.; Honeyman, J. A.; Tortolani, D. R.; Reczek, P. R.; Mansuri, M. M.; Starrett, J. E., Jr. Retinoic Acid Receptor β,γ-Selective Ligands: Synthesis and Biological Activity of 6-Substituted 2-Naphthoic Acid Retinoids. J. Med. Chem. 1996, 39, 2411-2421.
26. Muccio, D. D.; Brouillette, W. J.; Alam, M.; Vaezi, M. F.; Sani, B. P.; Vanepally, P.; Reddy, L.; Li, E.; Norris, A. W.; Simpson-Herren, L.; Hill, D. L. Conformationally Defined 6-s-trans-Retinoic Acid Analogues. 3. Structure-Activity Relationships for Nuclear Receptor Binding, Transcriptional Activity, and Cancer Chemopreventive Activity. J. Med. Chem 1996, 39, 3625-3635.
27. Dawson, M. I.; Hobbs, P. D.; Chan, R. L.; Chao, W.; Fung, V. Aromatic Retinoic Acid Analogues. Synthesis and Pharmacological Activity. J. Med. Chem 1981, 24, 583-592.
28. Dawson, M. I.; Chao, W. R.; Hobbs, P. D.; Delair, T. In Chemistry and Biology of Synthetic Retinoids; Dawson, M. I., Okamurn, W. H., Eds.; CRC Press: Baca Raton, FL, 1990; pp 385-466.
29. Loeliger, P.; Bollag, W.; Mayer, H. Arotinoid, a new class of highly active retinoids. Eur. J. Med. Chem 1980, 15, 9-15.
30. Strickland, S.; Breitman, T. R.; Frickel, F.; Nurrenbach, A.; Hadicke, E.; Sporn, M. B. Structure-Activity Relationships of a New Series of Retinoidal Benzoic Acid Derivatives as Measured by Induction of Differentiation of Murine F9 Teratocarcinoma Cells and Human HL-60 Promyelocytic Leukemia Cells. Cancer Res 1983, 43, 5268-5272.
31. Shudo, K.; Kagechika, H. Structural Evolution of Retinoids. Adv. Drug Res 1993, 24, 81-119.
32. Kagechika, H.; Himi, T.; Kawachi, E.; Hashimoto, Y.; Shudo, K. Retinobenzoic Acids. 4. Conformation of Aromatic Amides with Retinoidal Activity. Importance of trans-Amide Structure for the Activity. J. Med. Chem 1989, 32, 2292-2296.
33. Shimasaki, H.; Kagechika, H.; Fukasawa, H.; Kawachi, E.; Shudo, K. Retinoidal Dienamides and Related Aromatic Amides. Replacement of the 9-Ene Structure of Retinoic Acid with a trans-or cis-Amide Group. Chem. Pharm. Bull 1995, 43, 100-107.
34. Kagechika, H.; Kawachi, E.; Hashimoto, Y.; Shudo, K. Differentiation Inducers of Human Promyelocytic Leukemia Cells HL-60 Phenylcarbamoylbenzoic Acids and Polyene Amides. Chem. Pharm. Bull 1986, 34, 2275-2278.
35. Kagechika, H.; Kawachi, E.; Hashimoto, Y.; Himi, T.; Shudo, K. Retinobenzoic Acids. 1. Structure-Activity Relationships of Aromatic Amides with Retinoidal Activity. J. Med. Chem 1988, 31, 2182-2192.
36. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; John Wiley & Sons: New York, 1994; pp 620-623. Priority rules are applied for selecting the atoms which would serve to measure the value of the single (s-trans or s-cis) bond dihedral angle. Therefore C1, C2, C′, and O′ are used for compound 7, and C1, C2, N, and C′ are used for compound 8.
37. Dawson, M. I.; Hobbs, P. D.; Derdzinski, K.; Chao, W. R.; Frenking, G.; Loews, G. H.; Jetten, A. M.; Napoli, J. L.; Williams, J. B.; Sani, B. P.; Wille, J. J.; Smith, L. J. Effect of Structural Modifications in the C7-C11 Region of the Retinoid Skeleton on Biological Activity in a Series of Aromatic Retinoids. J. Med. Chem 1989, 32, 1504-1507.
38. Kagechika, H.; Himi, T.; Namikawa, K.; Kawachi, E.; Hashimoto, Y.; Shudo, K. Retinobenzoic Acids. 3. Structure-Activity Relationships of Retinoidal Azobenzene-4-carboxylic Acids and Stilbene-4-carboxylic Acids. J. Med. Chem 1989, 32, 1098-1108.
39. Cookson, R. C.; Smith, S. A. Synthesis of 2-hydroxy-3-methylcyclopent-2-eneone from methyl acrylate. J. Chem. Soc., Perkin Trans. I 1979, 2447-2448.
40. Strating, J.; Reiffers, S.; Wynberg, H. An Improved Method for the Preparation of Non-Enolisable vic Diketones. Synthesis 1971, 209-211.
41. Castro, B.; Evin, G.; Selve, C.; Seyer, R. Peptide Coupling Reagents; VIII. A High Yield Preparation of Phenyl Esters of Amino Acids using Benzotriazolyloxytris[dimethylamino]phosphonium Hexafluorophosphate (BOP reagent). Synthesis 1977, 413-415.
42. Gassman, P. G.; Schenk, W. A General Procedure for the Base-Promoted Hydrolysis of Hindered Esters at Ambiant Temperatures. J. Org. Chem 1977, 42, 918-920.
43. Sieber, P. Der 2-trimethylsilyläthyl-Rest als Selectiv abspaltbare Carboxy-Schutzgrupp. Helv. Chim. Acta 1977, 60, 2711-2716.
44. Lee, J. B. Preparation of Acyl Halides under Very Mild Conditions. J. Am. Chem. Soc 1966, 88, 3440-3441.
45. Magid, R. M.; Fruchey, O. S.; Johnson, W. L.; Allen, T. G. Hexachloroacetone/Triphenylphosphine: A Mild Reagent for the Regioselective and Stereospecific Production of Allylic Chlorides from the Alcohols. J. Org. Chem 1979, 44, 359-363.
46. Villeneuve, G. B.; Chan, T. H. A Rapid, Mild and Acid-Free Procedure for the Preparation of Acyl Chlorides Including Formyl Chloride. Tetrahedron lett 1997, 38, 6489-6492.
47. Andrewes, A. G.; Liaaen-Jensen, S. Animal Caroteneoids 8: Synthesis of β,γ-Carotene and γ,γ-Carotene. Acta Chim. Scand. 1973, 27, 1401-1409.
48. Shioiri, T.; Ninomiya, K.; Yamada, S.I. Diphenylphosphoryl Azide. A New Convenient Reagent for a Modified Curtius Reaction and for the Peptide Synthesis J. Am. Chem. Soc 1972, 94, 6203-6205.
49. Belleau, B.; Malek, G. A New Convenient Reagent for Peptide Syntheses. J. Am. Chem. Soc 1968, 90, 1651-1652.
50. Cabré, J.; Palomo, A. L.; New Experimental Strategies in Amide Synthesis using N-N-Bis[2-oxo-3-oxazolidinyl]phosphorodiamidic Chloride Synthesis 1984, 413-417.
51. Olah, G. A.; Nojma, M.; Kerekes, I. Synthetic Methods and Reactions; IV. Fluorination of Carboxylic Acids with Cyanuric Fluoride. Synthesis 1973, 487-488.
52. Panetta, C. A.; Casanova, T. G. Trichloroacetylation of Dipeptides by Hexachloroacetone in Dimethyl Sulfoxide under Neutral Conditions. J. Org. Chem 1970, 35, 2423-2425.
53. Collins, S. J.; Gallo, R. C.; Gallagher, R. E. Continuous Growth and Differentiation of Human Myeloid Leukaemic Cells in Suspension Culture. Nature (London) 1977, 270, 347-349.
54. Koeffler, H. P. Induction of Differentiation of Human Acute Myelogenous Leukemia Cells: Therapeutic Implications. Blood 1983, 62, 709-721.
55. Bodner, A. J.; Ting, R. C.; Gallo, R. C. Induction of Differentiation of Human Promyelocytic Leukemia Cells (HL-60) by Nucleosides and Methotrexate. J. Natl. Cancer Inst 1981, 67, 1025.
56. Collins, S. J.; Ruscetti, F. W.; Gallagher, R. E.; Gallo, R. C. Normal Functional Characteristics of Cultered Human Promyelocytic Leukemia Cells (HL-60) after Induction of Differentiation by Dimethyl sulfoxide. J. Exp. Med 1979, 149, 969-974.
57. McBurney, M. W.; Jones-Villeneuve, E. M. V.; Edwards, M. K. S.; Anderson, P. J. Control of muscle and neuronal differentiation in a cultured embryonal carcinoma cell line. Nature 1982, 299, 165-167.
58. Jones-Villeneuve, E. M. V.; McBurney, M. W.; Rogers, B. J.; Kalnins, V. I. Retinoic Acid Induces Embryonal Carcinoma Cells to Differentiate into Neurons and Glial Cells. J. Cell Biol 1982, 94, 253-262.
59. Jones-Villeneuve, E. M. V.; Rudnicki, M. A.; Harris, J. F.; McBurney, M. W. Retinoic Acid-Induced Neural Differentiation of Embryonal Carcinoma Cells. Mol. Cell Biol 1983, 3, 2271-2279.
60. Doré, B. T.; Vskokovic, M. R.; Momparler, R. L. Increased Sensitivity to a Vitamin D3 Analogue in HL-60 Myeloid Leukemic and Resistant to all-trans Retinoic Acid. Leukemia 1994, 8, 2179-2182.
61. Pratt, M. A. C.; Kralova, J.; McBurney, M. W. A Dominant Negative Mutation of the a Retinoic Acid Receptor Gene in a Retinoic Acid-Responsive Embryonal Carcinoma Cell. Mol. Cell Biol 1990, 10, 6445-6453.
62. Kessler, H. Conformation and Biological Activity of Cyclic Peptides. Angew. Chem., Int. Ed. Engl 1982, 21, 512-523.
63. Jeener, J.; Meier, B. H.; Bachmann, P.; Ernst, R. R. Investigation of exchange processes by two dimensional NMR spectroscopy. J. Chem. Phys 1979, 71, 4546-4553.
64. States, D. J.; Haberkorn, R. A.; Ruben, D. J. A Two-Dimensional Nuclear Overhauser Experiment with Pure Absorption Phase in Four Quadrants. J. Magn. Reson 1982, 48, 286-292.
65. Positive NOEs were also observed between H4 and H5 and tne methyls of the cyclohexenyl moiety. This observation is consistent with the large deviation from a perfect s-cis conformation for the bond between C1′ and C5 (the corresponding dihedral angle is -56° for the model presented in Figure 3). The negative NOEs obtained for interactions within the conjugated side chain argue in favor of a relatively rigid conformation in this region and a greater degree of mobility of the cyclohexenyl moiety (possibly owing to the existence of two energetically equivalent half-chair conformations).
66. SAINT, Release 4.05; Siemens Energy and Automation Inc., Madison, WI 53719; 1996.
67. Sheldrick, G. M. SADABS (Siemens Area Detector Absorption Corrections); University of Gottingen, Germany, 1996.
68. Sheldrick, G. M. SHELX-86. Program for the Solution of Crystal Structure; University of Gottingen, Germany.
69. Sheldrick, G. M. SHELX-93. Program for Structure Analysis; University of Gottingen, Germany.