Synthesis and anticancer activity of γ-(triazolyl ethylidene)butenolides and polyfunctional pyrrolinones

European Journal of Medicinal Chemistry

Volumn 82, Issue , 2014, Pages 106-119

  Devender, N ^a   Ramakrishna, K K G ^a   Hamidullah, ^a   Shukla, Sanjeev K ^a,b   Konwar, Rituraj ^a,b   Tripathi, Rama P ^a,b  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

^b ACADEMY OF SCIENTIFIC AND INNOVATIVE RESEARCH ACSIR   (India)

Author keywords

1,2,3 Triazole; 5 Hydroxy pyrrolinone; Anticancer activity; Ethylidenepyrrolinone; Ethylidenebutenolide

Indexed keywords

3,4 BIS(BENZYLOXY) 1 OCTYL 5 (2 (4 (PYRIDIN 2 YL) 1H PYRROL 2(5H) ONE; 3,4 BIS(BENZYLOXY) 1 PROPYL 5 (2 (4 (PYRIDIN 2 YL) 1H 1,2,3 TRIAZOL 1 YL)ETHYLIDENE) 1H PYRROL 2(5H) ONE; 3,4 BIS(BENZYLOXY) 1 PROPYL 5 (2 (4 PROPYL 1H 1,2,3 TRIAZOL 1 YL)ETHYLIDENE) 1H PYRROL 2(5H) ONE; 3,4 BIS(BENZYLOXY) 5 (2 (4 (4 TERT BUTYLPHENYL) 1H 1,2,3 TRIAZOL 1 YL)ETHYL) 5 HYDROXY 1H PYRROL 2(5H) ONE; 3,4 BIS(BENZYLOXY) 5 (2 (4 CYCLOHEXENYL 1H 1,2,3 TRIAZOL 1YL)ETHYL) 5 HYDROXY 1H PYRROL 2(5H) ONE; 3,4 BIS(BENZYLOXY) 5 HYDROXY 5 (2 (4 P TOLYL 1H 1,2,3 TRIAZOL 1 YL)ETHYL) 1H PYRROL 2(5H) ONE; 3,4 BIS(BENZYLOXY) 5 HYDROXY 5 (2 (4 PHENYL 1H 1,2,3 TRIAZOL 1 YL)ETHYL) 1H PYRROL 2 (5H) ONE; 5 HYDROXY 3,4 DIMETHOXY 5 (2 (4 P TOLYL 1H 1,2,3 TRIAZOL 1 YL)ETHYL) 1H PYRROL 2(5H) ONE; 5 HYDROXY 3,4 DIMETHOXY 5 (2 (4 PHENYL 1H 1,2,3 TRIAZOL 1 YL)ETHYL) 1H PYRROL 2(5H) ONE; ANTINEOPLASTIC AGENT; ASCORBIC ACID; BUTENOLIDE; GAMMA (TRIAZOLYL ETHYLIDENE) BUTENOLIDE; REACTIVE OXYGEN METABOLITE; SYNAPTOPHYSIN; TOLUENESULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG; 2 PYRROLIDONE DERIVATIVE; GAMMA BUTYROLACTONE; TRIAZOLE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; ARTICLE; BREAST CANCER; CANCER INHIBITION; CARBON NUCLEAR MAGNETIC RESONANCE; CELL PROLIFERATION; CHEMICAL REACTION; CONTROLLED STUDY; CYTOTOXICITY; DRUG POTENCY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; MCF 7 CELL LINE; MOLECULE; PROTEIN PROTEIN INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; ANALOGS AND DERIVATIVES; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; DRUG SCREENING; HCT116 CELL LINE; HEK293 CELL LINE; METABOLISM; SYNTHESIS; TUMOR CELL LINE;

4-BUTYROLACTONE; ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL LINE, TUMOR; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; HCT116 CELLS; HEK293 CELLS; HUMANS; MCF-7 CELLS; MOLECULAR STRUCTURE; PYRROLIDINONES; REACTIVE OXYGEN SPECIES; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZOLES;

EID: 84901914002     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.05.042     Document Type: Article

References (53)

1. T.J. Hsieh, F.R. Chang, Y.C. Chia, C.Y. Chen, H.C. Lin, H.F. Chiu, and Y.C. Wu The alkaloids of artabotrys uncinatus J. Nat. Prod. 64 2001 1157 1161
2. D. Kuhnt, T. Anke, H. Besl, M. Bross, R. Herrmann, U. Mocek, B. Steffan, and W. Steglich Antibiotics from basidiomycetes XXXVII. New inhibitors of cholesterol biosynthesis from cultures of Xerula melanotricha dorfelt J. Antibiot. 43 1990 1413 1420 (Pubitemid 20378499)
3. Y.S. Rao Chemistry of butenolides Chem. Rev. 64 1964 353 388
4. Y.S. Rao Recent advances in the chemistry of unsaturated lactones Chem. Rev. 76 1976 625 694
5. T.K.M. Shing, V.W.F. Tai, and H.C. Tsui Gonibutenolides A and B: serendipitous syntheses, relative and absolute configuration J. Chem. Soc. Chem. Commun. 11 1994 1293 1294 (Pubitemid 24175634)
6. T.K.M. Shing, H.C. Tsui, and Z.H. Zhou Enantiospecific syntheses of (+) goniofufurone, (+)-7-epi-goniofufurone, (+)-goniobutenolide A, (-)-goniobutenolide B, (+)-goniopypyrone, (+)-altholactone, (+)-goniotriol, and (+)-7-acetylgoniotriol J. Org. Chem. 60 1995 3121 3130
7. S. Ma, Z. Shi, and Z. Yu Synthesis of β-halobutenolides and their Pd(0) catalyzed cross coupling reactions with terminal alkynes and organo zinc reagents. A general route to β-substituted butenolides and formal synthesis of cis-whisky lactone Tetrahedron 55 1999 12137 12148 (Pubitemid 29453683)
8. E.I. Negishi, and M. Kotora Regio and stereo selective synthesis of γ-alkylidenebutenolides and related compounds Tetrahedron 53 1997 6707 6738 (Pubitemid 27208395)
9. R. Bruckner The synthesis of γ-alkylidenebutenolides Curr. Org. Chem. 5 2001 679 718
10. F. Bellina, C. Anselmi, and R. Rossi Total synthesis of rubrolide M and some of its unnatural congeners Tetrahedron Lett. 43 2002 2023 2027 (Pubitemid 34188514)
11. M. Szlosek, and B. Figadere Highly enantioselective aldol reaction with 2-trimethylsilyloxyfuran: the first catalytic asymmetric autoinductive aldol reaction Angew. Chem. Int. Ed. 39 2000 1799 1801 (Pubitemid 30365763)
12. F. Velazquez, and H.F. Olivo Synthesis of bicyclic γ- ylidenetetronates Org. Lett. 4 2002 3175 3178
13. S. Piper, and N. Risch γ-Regioselectivity of (furan-2-yloxy)- trimethylsilane towards iminium salts: synthesis of γ-arylidenebutenolides Arkivoc i 2003 86 92 (Pubitemid 40525428)
14. S.C. Bang, Y. Kim, M.Y. Yun, and B.Z. Ahn 5-arylidene-2(5H)-furanone derivatives: synthesis and structure-activity relationship for cytotoxicity Arch. Pharmacal Res. 27 2004 485 494 (Pubitemid 43080171)
15. D.C. Harrowven, J.D. Wilden, M.J. Tyte, M.B. Hursthouse, and S.J. Coles A new approach to the pseudopterosins using an arene alkylation with a γ-methylene-γ-butyrolactone Tetrahedron Lett. 42 2001 1193 1195 (Pubitemid 32149876)
16. M. Bella, G. Piancatelli, A. Squarcia, and C. Trolli Direct vinylogous aldol addition of γ-butyrolactones and γ-butyrolactams Tetrahedron Lett. 41 2000 3669 3672 (Pubitemid 30322042)
17. M. Bella, G. Piancatelli, and A. Squarcia Efficient preparation of 3-substituted-furan-2(5H)-ones and their direct vinylogous aldol addition Tetrahedron 57 2001 4429 4436 (Pubitemid 32441638)
18. F. Bellina, C. Anselmi, F. Martina, and R. Rossi Mucochloric acid: a useful synthon for the selective synthesis of 4-aryl-3-chloro-2(5H)-furanones, (Z)-4-aryl-5-[1-(aryl)methylidene]-3-chloro-2(5H)-furanones and 3,4-diaryl-2(5H)-furanones Eur. J. Org. Chem. 12 2003 2290 2302
19. M. Ito, T. Iwata, and K. Tsukida Retinoids and related Compounds.VII. Synthesis of retinoidal 4-ylidenebutenolides and their homologues Chem. Pharm. Bull. 32 1984 1709 1716 (Pubitemid 14111354)
20. X.C. Li, D. Ferreira, M.R. Jacob, Q. Zhang, S.I. Khan, H.N. EISohly, D.G. Nagle, T.J. Smillie, I.A. Khan, L.A. Walker, and A.M. Clark Antifungal cyclopentenediones from Piper coruscans J. Am. Chem. Soc. 126 2004 6872 6873 (Pubitemid 38855378)
21. A. Sorg, K. Siegel, and R. Bruckner A novel access to γ-alkylidenebutenolides: sequential stille couplings of dibromomethylene butenolides Synlett 2 2004 321 325 (Pubitemid 38241225)
22. A. Sorg, and R. Bruckner Total synthesis of xerulinic acid Angew. Chem. Int. Ed. 43 2004 4523 4526 (Pubitemid 39257398)
23. C. Coperet, T. Sugihara, G. Wu, I. Shimoyama, and E.I. Negishi Acylpalladation of internal alkynes and palladium-catalyzed carbonylation of (Z)-β-iodoenones and related derivatives producing γ-lactones and γ-lactams J. Am. Chem. Soc. 117 1995 3422 3431
24. S. Rousset, J. Thibonnet, M. Abarbri, A. Duchene, and J.L. Parrain Halolactonisation of (2Z,4E)-dienoic acids. A novel approach to γ-alkylidene butenolides Synlett 2 2000 260 262 (Pubitemid 30106384)
25. 3 Tetrahedron Lett. 43 2002 5673 5676 (Pubitemid 34786538)
26. S. Rousset, M. Abarbri, J. Thibonnet, J.L. Parrain, and A. Duchene Regio and stereo selective preparation ofγ-alkylidenebutenolides or α-pyrones using a stille reaction and palladium-catalysed oxacyclisation sequence Tetrahedron Lett. 44 2003 7633 7636 (Pubitemid 37130234)
27. S.S. Bisht, N. Dwivedi, and R.P. Tripathi L-ascorbic acid in organic synthesis: a facile synthesis of 4-(butenolide-5-methylidenyl)-1,4- dihydropyridines Tetrahedron Lett. 48 2007 1187 1189 (Pubitemid 46097044)
28. M.A. Khan, and H. Adams Simple and efficient stereoselective synthesis of (Z)-and (E)-alkylidine 2,3-dimethoxybutenolides from L-ascorbic acid and D-isoascorbic acid Synthesis 6 1995 687 692
29. A. Furstner Chemistry and biology of roseophilin and the prodigiosin alkaloids: a survey of the last 2500 years Angew. Chem. Int. Ed. 42 2003 3582 3603 (Pubitemid 37010641)
30. M.A. Khan, and H. Adams The formation of lactams from L-ascorbic acid Carbohydr. Res. 322 1999 279 283 (Pubitemid 30035457)
31. B.K. Singh, S.S. Bisht, and R.P. Tripathi An efficient synthesis of tetramic acid derivatives with extended conjugation from L-ascorbic acid Beilstein J. Org. Chem. 2 2006 24
32. Z. Feng, F. Chu, Z. Guo, and P. Sun Synthesis and anti-inflammatory activity of the major metabolites of imrecoxib Bioorg. Med. Chem. Lett. 19 2009 2270 2272
33. V.L. Gein, V.V. Yushkov, T.A. Splina, L.F. Gein, K.V. Yatsenko, and S.G. Shevtsova Anti-inflammatory and analgesic activity of 5-aryl-4-acyl-1-heteryl-3- hydroxy-3-pyrrolin-2-ones Pharm. Chem. J. 42 2008 255 257
34. V.L. Gein, N.N. Kasimova, A.L. Moiseev, M.A. Sheptukha, B.Ya. Syropyatov, N.G. Ismailova, E.V. Voronina, and O.I. Ivanenko Pharm. Chem. J. 41 2007 476 479
35. M.D. Parenti, S. Pacchioni, A.M. Ferrari, and G. Rastelli Three-dimensional quantitative structure-activity relationship analysis of a set of Plasmodium falciparum dihydrofolate reductase inhibitors using a pharmacophore generation approach J. Med. Chem. 47 2004 4258 4267 (Pubitemid 39045431)
36. B.L. Mylari, T.A. Beyer, and T.W. Siegel A highly specific aldose reductase inhibitor, ethyl 1-benzyl-3-hydroxy-2(5H)-oxopyrrole-4-carboxylate and its congeners J. Med. Chem. 34 1991 1011 1018
37. E.K. Lee, W.T. Regenold, and P. Shapiro Inhibition of aldose reductase enhances HeLa cell sensitivity to chemotherapeutic drugs and involves activation of extracellular signal-regulated kinases Anticancer Drugs 13 2002 859 868
38. T.R.K. Reddy, C. Li, X. Guo, H.K. Myrvang, P.M. Fischer, and L.V. Dekker Design, synthesis and structure-activity relationship exploration of 1-substituted 4-aroyl-3-hydroxy-5-phenyl-1H-pyrrol-2(5H)-one analogues as inhibitors of the annexin A2-S100A10 protein interaction J. Med. Chem. 54 2011 2080 2094
39. H. Miyazakai, T. Ogiku, H. Sai, Y. Moritani, A. Ohtani, and H. Ohmizu Synthesis and evaluation of pyrrolin-2-one compounds, a series of plasminogen activator inhibitor-1 inhibitors Chem. Pharm. Bull. 57 2009 979 985
40. R. Dayam, L.Q. Al-Mawasawi, and N. Neamati Substituted 2-pyrrolinone inhibitors of HIV-1 integrase Bioorg. Med. Chem. Lett. 17 2007 6155 6159 (Pubitemid 47552842)
41. H.R. Bokesch, R.S. Gardella, D.C. Rabe, D.P. Bottaro, W.M. Linehan, J.B. McMahon, and T.C. McKee A new hypoxia inducible factor-2 inhibitory pyrrolinone alkaloid from roots and stems of piper sarmentosum Chem. Pharm. Bull. 59 2011 1178 1179
42. G. Lang, A.L.J. Cole, J.W. Blunt, and M.H.G. Munro An unusual oxalylated tetramic acid from the New Zealand basidiomycete Chamonixia pachydermis J. Nat. Prod. 69 2006 151 153 (Pubitemid 43241776)
43. Y.L. Yang, C.P. Lu, M.Y. Chen, K.Y. Chen, Y.C. Wu, and S.H. Wu Cytotoxic polyketides containing tetramic acid moieties isolated from the fungus Myceliophthora thermophila: elucidation of the relationship between cytotoxicity and stereo configuration Chem. Eur. J. 13 2007 6985 6991
44. C.C. Cosner, J.T. Markiewicz, P. Bourbon, C.J. Mariani, O. Wiest, M. Rujoi, A.I. Rosenbaum, A.Y. Huang, F.R. Maxfield, and P. Helquist Investigation of N-aryl-3-alkylidenepyrrolinones as potential Niemann-pick type C disease therapeutics J. Med. Chem. 52 2009 6494 6498
45. I.E. Valverde, A. Bauman, C.A. Kluba, S. Vomstein, M.A. Walter, and T.L. Mindt 1,2,3-Triazoles as amide bond mimics: triazole scan yields protease-resistant peptidomimetics for tumor targeting Angew. Chem. Int. Ed. 52 2013 8957 8960
46. Md.Z. Sultan, K. Park, S.Y. Lee, J.K. Park, T. Varughese, and S.S. Moon Novel oxidized derivatives of antifungal pyrrolnitrin from the bacterium Burkholderia cepacia K87 J. Antibiot. 61 2008 420 425
47. J.A.V. Blodgett, D.C. Oh, S. Cao, C.R. Currie, R. Kolter, and J. Clardy Common biosynthetic origins for polycyclic tetramate macrolactams from phylogenetically diverse bacteria PNAS 107 2010 11692 11697
48. J.K. Crandall, L.C. Crawley, and J.B. Komin Reaction of N-isopropylallenimine with organic azides J. Org. Chem. 40 1975 2045 2047
49. Qi Chen, M.G. Espey, M.C. Krishna, J.B. Mitchell, C.P. Corpe, G.R. Buettner, E. Shacter, and M. Levine Pharmacologic ascorbic acid concentrations selectively kill cancer cells: action as a prodrug to deliver hydrogen peroxide to tissues Proc. Natl. Acad. Sci. U. S. A. 102 2005 13604 13609 (Pubitemid 41420895)
50. M.P. Gamcsik, M.S. Kasibhatla, D.J. Adams, J.L. Flowers, O.M. Colvin, G. Manikumar, M. Wani, M.E. Wall, G. Kohlhagen, and Y. Pommier Dual role of glutathione in modulating camptothecin activity: depletion potentiates activity, but conjugation enhances the stability of the topoisomerase I-DNA complex Mol. Cancer Ther. 1 2001 11 20
51. S. Ohno, Y. Ohno, N. Suzuki, G. Soma, and M. Inoue High-dose vitamin C therapy (ascorbic acid) therapy in the treatment of patients with advanced cancer Anticancer Res. 29 2009 809 815
52. Qi Chen, M.G. Espey, A.Y. Sun, J.H. Lee, M.C. Krishna, E. Shacter, P.L. Choyke, C. Pooput, K.L. Kirk, G.R. Buettner, and M. Levine Ascorbate in pharmacologic concentrations selectively generates ascorbate radical and hydrogen peroxide in extracellular fluid in vivo Proc. Natl. Acad. Sci. U. S. A. 104 2007 8749 8754 (Pubitemid 47175383)
53. Z. Xia, M. Dickens, J. Raingeaud, R.J. Davis, and M.E. Greenberg Opposing effects of ERK and JNK-p38 MAP kinases on apoptosis Science 270 1995 1326 1331