Research Article
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Synthesis and Characterization of Some New 4-Methyl-5-Imidazole Carbaldehyde Derivatives

Year 2019, , 373 - 382, 20.10.2019
https://doi.org/10.18596/jotcsa.530757

Abstract

Imidazole is a common and important heterocyclic
fragment of many biologically important molecules. 5-imidazole-carbaldehydes
containing mono- (N-1) methyl (or aryl) analogs are commonly used as building
blocks in medical chemistry. In this study, starting from
4-methyl-1H-imidazole-5-carbaldehyde, the N-1 atom of the imidazole ring is
derived with different alkyl groups. In addition, both N atoms of the starting
imidazole-carbaldehyde were methylated to give
5-carbaldehyde-1,3,4-trimethyl-3-imidazolium salt. The salt which possess quite
reactive carbaldehyde group could be used as a precursor for synthesis of other
imidazolium derivatives. Furthermore, 4-methyl-5-imidazole carbaldehyde was
converted into the benzoxazole, benzothiazole and benzoimidazole by a two-step
reaction over the aldehyde group. These new compounds could display some
biological activities.

Supporting Institution

Bülent Ecevit University and Düzce University

Project Number

Bülent Ecevit University Grant no: BAP 2014-72118496-06) and Düzce University Grant No.: 2012.05.03.097

References

  • 1. Butler K, Howes HL, Lynch JE and Pirie DK. Nitroimidazole Derivatives. Relationship between Structure and Antitrichomonal Activity. J. Med. Chem. 1967;10(5):891–7.
  • 2. a) Giraldi PN, Mariotti V, Namini G, Tosolini GP, Dradi E, Logemann W, de Carnevi I, Monti G. Arzneimittelforsch. 1970; 20,52 b) Heeres J, Mostmans JH and Maes R, German Patent, 1975;2:429,755.
  • 3. Rufer C, Kessler HJ, Schroeder E. Chemotherapeutic nitroheterocycles 6. Substituted 5- aminomethyl-3-(5-nitro-2-imidazolylmethyleneamino)-2-oxazolidinones. J. Med. Chem. 1971; 14(2):94–6.
  • 4. Arton., Netherlands Patent, 1965, 6413814; Chem. Abstr., 1965, 63, 18097b
  • 5. Godefroi EF, Van Cutsem J, Van Der Eycken CAM, Janssen PAJ. Med. Chem. 1967;10:1160.
  • 6. Godefroi EF, Heeres J, Van Cutsem J, Janssen PAJ. Preparation and antimycotic properties of derivatives of 1-phenethylimidazole. J. Med. Chem. 1969;12 (5):784–91.
  • 7. Durant GJ, Emmett JC, Ganellin CR, Miles PD, Parsons ME, Prain HD, White GR. Cyanoguanidine-thiourea equivalence in the development of the histamine H2-receptor antagonist, cimetidine. J. Med. Chem. 1977;20 (7):901–6.
  • 8. Walter LA. German Patent. 1969;1: 905, 353; Chem. Abstr., 1970; 72, 317904.
  • 9. Almansa C, Alfón J, de Arriba AF , Cavalcanti FL, Escamilla I, Gómez LA, Miralles A, Soliva R, Bartrolí J, Carceller E, Merlos M, García-Rafanell J. Synthesis and Structure−Activity Relationship of a New Series of COX-2 Selective Inhibitors: 1,5-Diarylimidazoles, J. Med. Chem. 2003;46 (16):3463–75.
  • 10. Liu H, Kerdesky FA, Black LA, Fitzgerald M, Henry R, Ebenshade TA, Hancock AA, Bennani YL. An efficient multigram synthesis of the potent histamine H3 antagonist GT-2331 and the reassessment of the absolute configuration. J. Org. Chem. 2004;69(1):192-4.
  • 11. Nallan L, Bauer KD,  Bendale P, Rivas K, Yokoyama K, Hornéy CP, Pendyala PR, Floyd D, Lombardo LJ, Williams DK, Hamilton A, Sebti S, Windsor WT, Weber PC, Buckner FS, Chakrabarti D, Gelb MH, Voorhis WCV. Protein Farnesyltransferase Inhibitors Exhibit Potent Antimalarial Activity. J. Med. Chem. 2005;48(11):3704-13.
  • 12. Berezin M, Achilefu S. Novel synthon for incorporating 1,3-dimethyl-imidazolium group into molecular architecture. Tetrahedron Letters. 2007;48(7):1195–9.
  • 13. Davis Jr JH, Forrester KJ, Merrigan T. Novel organic ionic liquids (OILs) incorporating cations derived from the antifungal drug miconazole. Tetrahedron Letters. 1998;39(49):8955-8.
  • 14. Hu B, Malamas M, Ellingboe J, Largis E, Han S, Mulvey R, Tillett J. New oxadiazolidinedione derivatives as potent and selective human β3 agonists. Bioorganic & Medicinal Chemistry Letters. 2001;11(8): 981-4.
  • 15. Demberelnyamba D, Kim K-S, Choi S, Park S-Y, Lee H, Kim C-J, Yoo I-D. Synthesis and antimicrobial properties of imidazolium and pyrrolidinonium salts. Bioorganic & Medicinal Chemistry. 2004;12(5):853–7.
  • 16. Ourth DD. Antiviral activity against human immunodeficiency virus-1 in vitro by myristoylated-peptide from Heliothis virescens. Biochemical and Biophysical Research Communications. 2004;320(1):190–6.
  • 17. Orhan E, Garci A, Tina R, Saudani M, Dyson PJ, Therrien B. Cytotoxic double arene ruthenium metalla-cycles that overcome cisplatin resistance. Journal of Organometallic Chemistry, 2016;803: 39-44.
  • 18. Orhan E, Garci A, Riedel T, Dyson PJ, Therrien B. Cytotoxicity of arene ruthenium metalla-rectangles incorporating bispyridyl diimide linkers. Journal of Organometallic Chemistry, 2016; 815-816: 53-8.
  • 19. Zabielska-Matejuk J. Antifungal properties of new quaternary ammonium compounds in relation to their surface activity. Wood Sci Technol. 2005;39(3):235–43.
  • 20. Reiter LA. Synthesis of 4(5)-acyl-, 1-substituted 5-acyl- and 1-substituted 4-acyl-1H-imidazoles from 4-aminoisoxazoles. J. Org. Chem. 1987;52(13):2714–26.
  • 21. Koch P, Ansideri F. 2-​Alkylsulfanyl-​4(5)​-​aryl-​5(4)​-​heteroarylimidazoles: An Overview on synthetic Strategies and Biological Activity. Arch. Pharm. Chem. Life Sci. 2017;350(12): e1700258.
  • 22. Beyer C, Wagenknecht H-A. Synthesis of Spiropyrans As Building Blocks for Molecular Switches and Dyads. J. Org. Chem. 2010;75(8):2752–5.
  • 23. Küçükbay H, Durmaz R, Orhan E, Günal S. Synthesis, antibacterial and antifungal activities of electron-rich olefins derived benzimidazole compounds. Il Farmaco. 2003;58(6):431-7.
  • 24. Akkurt M, Öztürk S, Küçükbay H, Orhan E, Büyükgüngör O. 1-Ethyl-3-(2-phenylethyl) benzimidazole-2-selone. Acta Crystallographica Section E: Structure Reports Online. 2004;60(7):o1263-o1265.
  • 25. Akkurt M, Yıldırım SO, Orhan E, Küçükbay H, Büyükgüngör O. 1-Methoxyethyl-5- nitrobenzimidazole. Acta Crystallographica Section E: Structure Reports Online. 2005;61(9):o2804-5.
  • 26. Yıldırım SO, Akkurt M, Küçükbay H, Orhan E, Büyükgüngör O. 6-Nitro-1-(2-phenylethyl)1H-benzimidazole. Acta Crystallographica Section E: Structure Reports Online. 2005;61(7):o2038-9.
  • 27. Küçükbay H, Günal S, Orhan E, Durmaz R. Synthesis and Antimicrobial Activities of Some Transition Metal Benzimidazole Complexes. Asian Journal of Chemistry. 2010;22(9):7376.
  • 28. Abdel-Magid AF, Carson KG, Harris BD, Maryanoff CA, Shah RD. Reductive Amination of Aldehydes and Ketones with Sodium Triacetoxyborohydride. Studies on Direct and Indirect Reductive Amination Procedures. J. Org. Chem. 1996;61(11):3849–62.
  • 29. Gwaltney SL, O’Connor SJ, Nelson LTJ, Sullivan GM, Imade H, Wang W, Hasvold L, Li Q, Cohen J, Gu W-Z, Tahir SK, Bauch J, Marsh K, Ng S-C, Frost DJ, Zhang H, Muchmore S, Jakob CG, Stoll V, Hutchins C, Rosenberg SH, Hing. Aryl tetrahydropyridine inhibitors of farnesyltransferase: bioavailable analogues with improved cellular potency. Bioorganic & Medicinal Chemistry Letters. 2003;13:1363– 6.
  • 30. Pınar Ş, Akkurt M, Küçükbay H, Orhan E, Büyükgüngör O. Bis[1-(but-2-enyl)-5-nitro-1H- benzimidazole-kN3]dichlorocobalt(II), Acta Crystallographica Section E: Structure Reports Online. 2006;62(7):m1663-5.
  • 31. Akkurt M, Karaca S, Küçükbay H, Orhan E, Büyükgüngör O. 1-Benzyl-3-(2- phenethyl)benzimidazolium bromide monohydrate, Acta Crystallographica Section E: Structure Reports Online. 2005;61(8):o2452-4.
  • 32. Akkurt M, Karaca S, Küçükbay H, Orhan E, Büyükgüngör O. Dichlorobis[1-(2- ethoxyethyl)-1H-benzimidazole-kN3]nickel(II), Acta Crystallographica Section E: Structure Online. 2004;61(1):m41-3.
  • 33. Hubball W, Pyman FL. Glyoxaline-​4(5)​-​formaldehyde. Journal of the Chemical Society, 1928; 21-32. 
  • 34. Reiter LA. Synthesis of 4(5)-Acyl-, 1-Substituted 5-Acyl-, and 1-Substituted 4-Acyl-1H- imidazoles from 4-Aminoisoxazoles. J. Org. Chem., 1987; 52(13): 2714-26.
  • 35. Gilbert JG, Addison AW, Palaniandavar M and Butcher RJ. Synthesis of Some Benzimidazole-, Benzothiazole- and Pyridine Derived Chelating Agents. Journal of Heterocyclic Chemistry, 2002;39(2):399-404.
Year 2019, , 373 - 382, 20.10.2019
https://doi.org/10.18596/jotcsa.530757

Abstract

Project Number

Bülent Ecevit University Grant no: BAP 2014-72118496-06) and Düzce University Grant No.: 2012.05.03.097

References

  • 1. Butler K, Howes HL, Lynch JE and Pirie DK. Nitroimidazole Derivatives. Relationship between Structure and Antitrichomonal Activity. J. Med. Chem. 1967;10(5):891–7.
  • 2. a) Giraldi PN, Mariotti V, Namini G, Tosolini GP, Dradi E, Logemann W, de Carnevi I, Monti G. Arzneimittelforsch. 1970; 20,52 b) Heeres J, Mostmans JH and Maes R, German Patent, 1975;2:429,755.
  • 3. Rufer C, Kessler HJ, Schroeder E. Chemotherapeutic nitroheterocycles 6. Substituted 5- aminomethyl-3-(5-nitro-2-imidazolylmethyleneamino)-2-oxazolidinones. J. Med. Chem. 1971; 14(2):94–6.
  • 4. Arton., Netherlands Patent, 1965, 6413814; Chem. Abstr., 1965, 63, 18097b
  • 5. Godefroi EF, Van Cutsem J, Van Der Eycken CAM, Janssen PAJ. Med. Chem. 1967;10:1160.
  • 6. Godefroi EF, Heeres J, Van Cutsem J, Janssen PAJ. Preparation and antimycotic properties of derivatives of 1-phenethylimidazole. J. Med. Chem. 1969;12 (5):784–91.
  • 7. Durant GJ, Emmett JC, Ganellin CR, Miles PD, Parsons ME, Prain HD, White GR. Cyanoguanidine-thiourea equivalence in the development of the histamine H2-receptor antagonist, cimetidine. J. Med. Chem. 1977;20 (7):901–6.
  • 8. Walter LA. German Patent. 1969;1: 905, 353; Chem. Abstr., 1970; 72, 317904.
  • 9. Almansa C, Alfón J, de Arriba AF , Cavalcanti FL, Escamilla I, Gómez LA, Miralles A, Soliva R, Bartrolí J, Carceller E, Merlos M, García-Rafanell J. Synthesis and Structure−Activity Relationship of a New Series of COX-2 Selective Inhibitors: 1,5-Diarylimidazoles, J. Med. Chem. 2003;46 (16):3463–75.
  • 10. Liu H, Kerdesky FA, Black LA, Fitzgerald M, Henry R, Ebenshade TA, Hancock AA, Bennani YL. An efficient multigram synthesis of the potent histamine H3 antagonist GT-2331 and the reassessment of the absolute configuration. J. Org. Chem. 2004;69(1):192-4.
  • 11. Nallan L, Bauer KD,  Bendale P, Rivas K, Yokoyama K, Hornéy CP, Pendyala PR, Floyd D, Lombardo LJ, Williams DK, Hamilton A, Sebti S, Windsor WT, Weber PC, Buckner FS, Chakrabarti D, Gelb MH, Voorhis WCV. Protein Farnesyltransferase Inhibitors Exhibit Potent Antimalarial Activity. J. Med. Chem. 2005;48(11):3704-13.
  • 12. Berezin M, Achilefu S. Novel synthon for incorporating 1,3-dimethyl-imidazolium group into molecular architecture. Tetrahedron Letters. 2007;48(7):1195–9.
  • 13. Davis Jr JH, Forrester KJ, Merrigan T. Novel organic ionic liquids (OILs) incorporating cations derived from the antifungal drug miconazole. Tetrahedron Letters. 1998;39(49):8955-8.
  • 14. Hu B, Malamas M, Ellingboe J, Largis E, Han S, Mulvey R, Tillett J. New oxadiazolidinedione derivatives as potent and selective human β3 agonists. Bioorganic & Medicinal Chemistry Letters. 2001;11(8): 981-4.
  • 15. Demberelnyamba D, Kim K-S, Choi S, Park S-Y, Lee H, Kim C-J, Yoo I-D. Synthesis and antimicrobial properties of imidazolium and pyrrolidinonium salts. Bioorganic & Medicinal Chemistry. 2004;12(5):853–7.
  • 16. Ourth DD. Antiviral activity against human immunodeficiency virus-1 in vitro by myristoylated-peptide from Heliothis virescens. Biochemical and Biophysical Research Communications. 2004;320(1):190–6.
  • 17. Orhan E, Garci A, Tina R, Saudani M, Dyson PJ, Therrien B. Cytotoxic double arene ruthenium metalla-cycles that overcome cisplatin resistance. Journal of Organometallic Chemistry, 2016;803: 39-44.
  • 18. Orhan E, Garci A, Riedel T, Dyson PJ, Therrien B. Cytotoxicity of arene ruthenium metalla-rectangles incorporating bispyridyl diimide linkers. Journal of Organometallic Chemistry, 2016; 815-816: 53-8.
  • 19. Zabielska-Matejuk J. Antifungal properties of new quaternary ammonium compounds in relation to their surface activity. Wood Sci Technol. 2005;39(3):235–43.
  • 20. Reiter LA. Synthesis of 4(5)-acyl-, 1-substituted 5-acyl- and 1-substituted 4-acyl-1H-imidazoles from 4-aminoisoxazoles. J. Org. Chem. 1987;52(13):2714–26.
  • 21. Koch P, Ansideri F. 2-​Alkylsulfanyl-​4(5)​-​aryl-​5(4)​-​heteroarylimidazoles: An Overview on synthetic Strategies and Biological Activity. Arch. Pharm. Chem. Life Sci. 2017;350(12): e1700258.
  • 22. Beyer C, Wagenknecht H-A. Synthesis of Spiropyrans As Building Blocks for Molecular Switches and Dyads. J. Org. Chem. 2010;75(8):2752–5.
  • 23. Küçükbay H, Durmaz R, Orhan E, Günal S. Synthesis, antibacterial and antifungal activities of electron-rich olefins derived benzimidazole compounds. Il Farmaco. 2003;58(6):431-7.
  • 24. Akkurt M, Öztürk S, Küçükbay H, Orhan E, Büyükgüngör O. 1-Ethyl-3-(2-phenylethyl) benzimidazole-2-selone. Acta Crystallographica Section E: Structure Reports Online. 2004;60(7):o1263-o1265.
  • 25. Akkurt M, Yıldırım SO, Orhan E, Küçükbay H, Büyükgüngör O. 1-Methoxyethyl-5- nitrobenzimidazole. Acta Crystallographica Section E: Structure Reports Online. 2005;61(9):o2804-5.
  • 26. Yıldırım SO, Akkurt M, Küçükbay H, Orhan E, Büyükgüngör O. 6-Nitro-1-(2-phenylethyl)1H-benzimidazole. Acta Crystallographica Section E: Structure Reports Online. 2005;61(7):o2038-9.
  • 27. Küçükbay H, Günal S, Orhan E, Durmaz R. Synthesis and Antimicrobial Activities of Some Transition Metal Benzimidazole Complexes. Asian Journal of Chemistry. 2010;22(9):7376.
  • 28. Abdel-Magid AF, Carson KG, Harris BD, Maryanoff CA, Shah RD. Reductive Amination of Aldehydes and Ketones with Sodium Triacetoxyborohydride. Studies on Direct and Indirect Reductive Amination Procedures. J. Org. Chem. 1996;61(11):3849–62.
  • 29. Gwaltney SL, O’Connor SJ, Nelson LTJ, Sullivan GM, Imade H, Wang W, Hasvold L, Li Q, Cohen J, Gu W-Z, Tahir SK, Bauch J, Marsh K, Ng S-C, Frost DJ, Zhang H, Muchmore S, Jakob CG, Stoll V, Hutchins C, Rosenberg SH, Hing. Aryl tetrahydropyridine inhibitors of farnesyltransferase: bioavailable analogues with improved cellular potency. Bioorganic & Medicinal Chemistry Letters. 2003;13:1363– 6.
  • 30. Pınar Ş, Akkurt M, Küçükbay H, Orhan E, Büyükgüngör O. Bis[1-(but-2-enyl)-5-nitro-1H- benzimidazole-kN3]dichlorocobalt(II), Acta Crystallographica Section E: Structure Reports Online. 2006;62(7):m1663-5.
  • 31. Akkurt M, Karaca S, Küçükbay H, Orhan E, Büyükgüngör O. 1-Benzyl-3-(2- phenethyl)benzimidazolium bromide monohydrate, Acta Crystallographica Section E: Structure Reports Online. 2005;61(8):o2452-4.
  • 32. Akkurt M, Karaca S, Küçükbay H, Orhan E, Büyükgüngör O. Dichlorobis[1-(2- ethoxyethyl)-1H-benzimidazole-kN3]nickel(II), Acta Crystallographica Section E: Structure Online. 2004;61(1):m41-3.
  • 33. Hubball W, Pyman FL. Glyoxaline-​4(5)​-​formaldehyde. Journal of the Chemical Society, 1928; 21-32. 
  • 34. Reiter LA. Synthesis of 4(5)-Acyl-, 1-Substituted 5-Acyl-, and 1-Substituted 4-Acyl-1H- imidazoles from 4-Aminoisoxazoles. J. Org. Chem., 1987; 52(13): 2714-26.
  • 35. Gilbert JG, Addison AW, Palaniandavar M and Butcher RJ. Synthesis of Some Benzimidazole-, Benzothiazole- and Pyridine Derived Chelating Agents. Journal of Heterocyclic Chemistry, 2002;39(2):399-404.
There are 35 citations in total.

Details

Primary Language English
Subjects Chemical Engineering
Journal Section Articles
Authors

Ersin Orhan 0000-0002-5461-1005

Mahmut Köse 0000-0003-2689-6661

Demet Alkan

Leyla Öztürk This is me 0000-0002-0485-9926

Project Number Bülent Ecevit University Grant no: BAP 2014-72118496-06) and Düzce University Grant No.: 2012.05.03.097
Publication Date October 20, 2019
Submission Date February 22, 2019
Acceptance Date September 8, 2019
Published in Issue Year 2019

Cite

Vancouver Orhan E, Köse M, Alkan D, Öztürk L. Synthesis and Characterization of Some New 4-Methyl-5-Imidazole Carbaldehyde Derivatives. JOTCSA. 2019;6(3):373-82.