Research Article
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Year 2017, , 787 - 810, 31.07.2017
https://doi.org/10.18596/jotcsa.309261

Abstract

References

  • 1. Denny WA, Rewcastle GW, Baguley BC. Potential antitumor agents. 59. Structure-activity relationships for 2-phenylbenzimidazole-4-carboxamides, a new class of minimal DNA-intercalating agents which may not act via topoisomerase II. Journal of Medicinal Chemistry. 1990 Feb;33(2):814–9.
  • 2. Demirayak Ş, Abu Mohsen U, Çağri Karaburun A. Synthesis and anticancer and anti-HIV testing of some pyrazino[1,2-a]benzimidazole derivatives. European Journal of Medicinal Chemistry. 2002 Mar;37(3):255–60.
  • 3. Sharma P, Sharma R, Tyagi R. Inhibitors of Cyclin Dependent Kinases: Useful Targets for Cancer Treatment. Current Cancer Drug Targets. 2008 Feb 1;8(1):53–75.
  • 4. Carcanague D, Shue Y-K, Wuonola MA, Uria-Nickelsen M, Joubran C, Abedi JK, et al. Novel Structures Derived from 2-[[(2-Pyridyl)methyl]thio]-1 H -benzimidazole as Anti- Helicobacterpylori Agents, Part 2. Journal of Medicinal Chemistry. 2002 Sep;45(19):4300–9.
  • 5. Lindberg P, Nordberg P, Alminger T, Braendstroem A, Wallmark B. The mechanism of action of the antisecretory agent omeprazole. Journal of medicinal chemistry. 1986;29(8):1327–1329.
  • 6. Küçükbay H, Durmaz B. Antifungal activity of organic and organometallic derivatives of benzimidazole and benzothiazole. Arzneimittelforschung. 1997 May;47(5):667–70.
  • 7. Olender D, Żwawiak J, Lukianchuk V, Lesyk R, Kropacz A, Fojutowski A, et al. Synthesis of some N-substituted nitroimidazole derivatives as potential antioxidant and antifungal agents. European Journal of Medicinal Chemistry. 2009 Feb;44(2):645–52.
  • 8. Fekner T, Gallucci J, Chan MK. Ruffling-Induced Chirality: Synthesis, Metalation, and Optical Resolution of Highly Nonplanar, Cyclic, Benzimidazole-Based Ligands. Journal of the American Chemical Society. 2004 Jan;126(1):223–36.
  • 9. Küçükbay H, Cetinkaya E, Durmaz R. Synthesis and antimicrobial activity of substituted benzimidazole, benzothiazole and imidazole derivatives. Arzneimittelforschung. 1995 Dec;45(12):1331–4.
  • 10. Durmaz R, Köroğlu M, Küçükbay H, Temel I, Ozer MK, Refiq M, et al. Investigation of serum minimal inhibitory concentrations of some benzimidazole, imidazole and benzothiazole derivatives and their effects on liver and renal functions. Arzneimittelforschung. 1998 Dec;48(12):1179–84.
  • 11. Zarrinmayeh H, Nunes AM, Ornstein PL, Zimmerman DM, Arnold MB, Schober DA, et al. Synthesis and Evaluation of a Series of Novel 2-[(4-Chlorophenoxy)methyl]- benzimidazoles as Selective Neuropeptide Y Y1 Receptor Antagonists. Journal of Medicinal Chemistry. 1998 Jul;41(15):2709–19.
  • 12. Hadizadeh F, Hosseinzadeh H, Motamed-Shariaty V, Seifi M, Kazemi S. Synthesis and Antidepressant Activity of N-Substituted Imidazole-5-Carboxamides in Forced Swimming Test Model. Iranian Journal of Pharmaceutical Research. 2010;Volume 7(Number 1):29–33.
  • 13. Naik P, Murumkar P, Giridhar R, Yadav MR. Angiotensin II receptor type 1 (AT1) selective nonpeptidic antagonists—A perspective. Bioorganic & Medicinal Chemistry. 2010 Dec;18(24):8418–56.
  • 14. Kubo K, Inada Y, Kohara Y, Sugiura Y, Ojima M, Itoh K, et al. Nonpeptide angiotensin II receptor antagonists. Synthesis and biological activity of benzimidazoles. J Med Chem. 1993 Jun 11;36(12):1772–84.
  • 15. Hauel NH, Nar H, Priepke H, Ries U, Stassen J-M, Wienen W. Structure-Based Design of Novel Potent Nonpeptide Thrombin Inhibitors. Journal of Medicinal Chemistry. 2002 Apr;45(9):1757–66.
  • 16. Porcari AR, Devivar RV, Kucera LS, Drach JC, Townsend LB. Design, Synthesis, and Antiviral Evaluations of 1-(Substituted benzyl)-2-substituted-5,6-dichlorobenzimidazoles as Nonnucleoside Analogues of 2,5,6-Trichloro-1-(β- d -ribofuranosyl)benzimidazole. Journal of Medicinal Chemistry. 1998 Apr;41(8):1252–62.
  • 17. Roth T, Morningstar ML, Boyer PL, Hughes SH, Buckheit, RW, Michejda CJ. Synthesis and Biological Activity of Novel Nonnucleoside Inhibitors of HIV-1 Reverse Transcriptase. 2-Aryl-Substituted Benzimidazoles. Journal of Medicinal Chemistry. 1997 Dec;40(26):4199–207.
  • 18. Pandey J, Tiwari VK, Verma SS, Chaturvedi V, Bhatnagar S, Sinha S, et al. Synthesis and antitubercular screening of imidazole derivatives☆. European Journal of Medicinal Chemistry. 2009 Aug;44(8):3350–5.
  • 19. Singh J, Grover P, Pathak DP. Synthesis, anticonvulsant activity and comparative QSAR study of some novel 1, 2, 5-trisubstituted benzimidazole derivatives. Acta Pharmaceutica Sciencia. 2010;52:511–522.
  • 20. Kandile NG, Mohamed MI, Ismaeel HM. Antiproliferative effects of metal complexes of new isatin hydrazones against HCT116, MCF7 and HELA tumour cell lines. Journal of Enzyme Inhibition and Medicinal Chemistry. 2012 Jun;27(3):330–8.
  • 21. Alaghaz A-NMA, El-Sayed BA, El-Henawy AA, Ammar RAA. Synthesis, spectroscopic characterization, potentiometric studies, cytotoxic studies and molecular docking studies of DNA binding of transition metal complexes with 1,1-diaminopropane–Schiff base. Journal of Molecular Structure. 2013 Mar;1035:83–93.
  • 22. Jiang X-R, Wang P, Smith CL, Zhu BT. Synthesis of Novel Estrogen Receptor Antagonists Using Metal-Catalyzed Coupling Reactions and Characterization of Their Biological Activity. Journal of Medicinal Chemistry. 2013 Apr 11;56(7):2779–90.
  • 23. Wu H, Kong J, Yang Z, Wang X, Shi F, Zhang Y, et al. Copper(II) and manganese(II) picrate complexes with the V-shaped ligand 1,3-bis(1-methylbenzimidazol-2-yl)-2-thiapropane: preparation, structure, DNA-binding properties and antioxidant activities. Transition Metal Chemistry. 2014 Nov;39(8):951–60.
  • 24. Jayamani A, Sengottuvelan N, Chakkaravarthi G. Synthesis, structural, electrochemical, DNA interaction, antimicrobial and molecular docking studies on dimeric copper(II) complexes involving some potential bidentate ligands. Polyhedron. 2014 Oct;81:764–76.
  • 25. El-Gammal OA, Mostafa MM. Synthesis, characterization, molecular modeling and antioxidant activity of Girard′s T thiosemicarbazide and its complexes with some transition metal ions. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2014 Jun;127:530–42.
  • 26. Nakamoto K. Infrared and Raman Spectra of Inorganic and Coordination Compounds. In: Chalmers JM, Griffiths PR, editors. Handbook of Vibrational Spectroscopy [Internet]. Chichester, UK: John Wiley & Sons, Ltd; 2006 [cited 2017 Mar 13]. Available from: http://doi.wiley.com/10.1002/0470027320.s4104
  • 27. Rahaman F, Mruthyunjayaswamy BHM. Synthesis, spectral characterization and biological activity studies of transition metal complexes of Schiff base ligand containing indole moiety. Complex Metals. 2014 Dec 31;1(1):88–95.
  • 28. Ashraf A, Siddiqui WA, Akbar J, Mustafa G, Krautscheid H, Ullah N, et al. Metal complexes of benzimidazole derived sulfonamide: Synthesis, molecular structures and antimicrobial activity. Inorganica Chimica Acta. 2016 Mar;443:179–85.
  • 29. Krishnamurthy G. Synthesis and Characterization of Ruthenium(III) Chloride Complexes with Some 1,2-Disubstituted Benzimidazoles and their Catalytic Activity. Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry. 2011 Jul;41(6):590–7.
  • 30. Munde A, Jagdale A, Jadhav S, Chondhekar T. Synthesis, characterization and thermal study of some transition metal complexes of an asymmetrical tetradentate Schiff base ligand. Journal of the Serbian Chemical Society. 2010;75(3):349–59.
  • 31. Lever ABP. Inorganic electronic spectroscopy. 2nd ed. Amsterdam ; New York: Elsevier; 1984. 863 p. (Studies in physical and theoretical chemistry).
  • 32. Dar AM, Shamsuzzaman, Khan S. Spectroscopic, Viscositic, DNA Binding and Cytotoxic Studies of Newly Synthesized Steroidal Imidazolidines. Journal of Fluorescence. 2016 Mar;26(2):639–49.
  • 33. Bari SB, Adhikari S, Surana S. Tyrosine kinase receptor inhibitors: A new target for anticancer drug development. Journal of PharmaSciTech. 2012;1(2):36–45.
  • 34. Shen L, Chu D. Type II DNA topoisomerases as antibacterial targets. Current Pharmaceutical Design. 1996;2(2):195–208.
  • 35. Yapati H, Devineni SR, Chirumamilla S, Kalluru S. Synthesis, characterization and studies on antioxidant and molecular docking of metal complexes of 1-(benzo[d]thiazol-2-yl)thiourea. Journal of Chemical Sciences. 2016 Jan;128(1):43–51.
  • 36. Yadav G, Ganguly S. Structure activity relationship (SAR) study of benzimidazole scaffold for different biological activities: A mini-review. European Journal of Medicinal Chemistry. 2015 Jun;97:419–43.

Synthesis, Cytotoxicity and Molecular Docking Study of Complexes Containing Thiazole Moiety

Year 2017, , 787 - 810, 31.07.2017
https://doi.org/10.18596/jotcsa.309261

Abstract




The
ligand 5-methyl-2-phenyl-4-[(E)-1,3-thiazol-2-yldiazenyl]-2,4-dihydro-3H-pyrazol-3-one
(Dy) has been synthesized by diazo coupling reactions of 5-methyl-2-phenyl-
2,4-dihydro-3H-pyrazol-3-one with 2-aminothiazole and ferric hydrogen sulfate
(FHS), as a catalyst, under solvent-free conditions. A series of complexes of
the ligand with Co(II), Ni(II), Cu(II), and Zn(II) ions are synthesized and
structurally characterized by 1H NMR, FTIR, and UV–Visible spectral techniques.
The cytotoxic activity of the complexes and the uncoordinated ligand against
human breast cancer (MCF-7) and chronic myelogenous leukemia cell line (human
erythroleukemia) (K-562) cell lines exhibits good viability in the range of
50.16–55.16% at a concentration of >100-110 µg/mL as compared to the
inhibition in the untreated cells. Further, the metal complexes and ligand were
screened against antibacterial strains of S. typhi, S. aureus, and E. coli.
Both the cytotoxicity and antioxidant studies are correlated with computational
docking analysis and powder XRD studies reviles that all complexes are in
crystalline nature.




References

  • 1. Denny WA, Rewcastle GW, Baguley BC. Potential antitumor agents. 59. Structure-activity relationships for 2-phenylbenzimidazole-4-carboxamides, a new class of minimal DNA-intercalating agents which may not act via topoisomerase II. Journal of Medicinal Chemistry. 1990 Feb;33(2):814–9.
  • 2. Demirayak Ş, Abu Mohsen U, Çağri Karaburun A. Synthesis and anticancer and anti-HIV testing of some pyrazino[1,2-a]benzimidazole derivatives. European Journal of Medicinal Chemistry. 2002 Mar;37(3):255–60.
  • 3. Sharma P, Sharma R, Tyagi R. Inhibitors of Cyclin Dependent Kinases: Useful Targets for Cancer Treatment. Current Cancer Drug Targets. 2008 Feb 1;8(1):53–75.
  • 4. Carcanague D, Shue Y-K, Wuonola MA, Uria-Nickelsen M, Joubran C, Abedi JK, et al. Novel Structures Derived from 2-[[(2-Pyridyl)methyl]thio]-1 H -benzimidazole as Anti- Helicobacterpylori Agents, Part 2. Journal of Medicinal Chemistry. 2002 Sep;45(19):4300–9.
  • 5. Lindberg P, Nordberg P, Alminger T, Braendstroem A, Wallmark B. The mechanism of action of the antisecretory agent omeprazole. Journal of medicinal chemistry. 1986;29(8):1327–1329.
  • 6. Küçükbay H, Durmaz B. Antifungal activity of organic and organometallic derivatives of benzimidazole and benzothiazole. Arzneimittelforschung. 1997 May;47(5):667–70.
  • 7. Olender D, Żwawiak J, Lukianchuk V, Lesyk R, Kropacz A, Fojutowski A, et al. Synthesis of some N-substituted nitroimidazole derivatives as potential antioxidant and antifungal agents. European Journal of Medicinal Chemistry. 2009 Feb;44(2):645–52.
  • 8. Fekner T, Gallucci J, Chan MK. Ruffling-Induced Chirality: Synthesis, Metalation, and Optical Resolution of Highly Nonplanar, Cyclic, Benzimidazole-Based Ligands. Journal of the American Chemical Society. 2004 Jan;126(1):223–36.
  • 9. Küçükbay H, Cetinkaya E, Durmaz R. Synthesis and antimicrobial activity of substituted benzimidazole, benzothiazole and imidazole derivatives. Arzneimittelforschung. 1995 Dec;45(12):1331–4.
  • 10. Durmaz R, Köroğlu M, Küçükbay H, Temel I, Ozer MK, Refiq M, et al. Investigation of serum minimal inhibitory concentrations of some benzimidazole, imidazole and benzothiazole derivatives and their effects on liver and renal functions. Arzneimittelforschung. 1998 Dec;48(12):1179–84.
  • 11. Zarrinmayeh H, Nunes AM, Ornstein PL, Zimmerman DM, Arnold MB, Schober DA, et al. Synthesis and Evaluation of a Series of Novel 2-[(4-Chlorophenoxy)methyl]- benzimidazoles as Selective Neuropeptide Y Y1 Receptor Antagonists. Journal of Medicinal Chemistry. 1998 Jul;41(15):2709–19.
  • 12. Hadizadeh F, Hosseinzadeh H, Motamed-Shariaty V, Seifi M, Kazemi S. Synthesis and Antidepressant Activity of N-Substituted Imidazole-5-Carboxamides in Forced Swimming Test Model. Iranian Journal of Pharmaceutical Research. 2010;Volume 7(Number 1):29–33.
  • 13. Naik P, Murumkar P, Giridhar R, Yadav MR. Angiotensin II receptor type 1 (AT1) selective nonpeptidic antagonists—A perspective. Bioorganic & Medicinal Chemistry. 2010 Dec;18(24):8418–56.
  • 14. Kubo K, Inada Y, Kohara Y, Sugiura Y, Ojima M, Itoh K, et al. Nonpeptide angiotensin II receptor antagonists. Synthesis and biological activity of benzimidazoles. J Med Chem. 1993 Jun 11;36(12):1772–84.
  • 15. Hauel NH, Nar H, Priepke H, Ries U, Stassen J-M, Wienen W. Structure-Based Design of Novel Potent Nonpeptide Thrombin Inhibitors. Journal of Medicinal Chemistry. 2002 Apr;45(9):1757–66.
  • 16. Porcari AR, Devivar RV, Kucera LS, Drach JC, Townsend LB. Design, Synthesis, and Antiviral Evaluations of 1-(Substituted benzyl)-2-substituted-5,6-dichlorobenzimidazoles as Nonnucleoside Analogues of 2,5,6-Trichloro-1-(β- d -ribofuranosyl)benzimidazole. Journal of Medicinal Chemistry. 1998 Apr;41(8):1252–62.
  • 17. Roth T, Morningstar ML, Boyer PL, Hughes SH, Buckheit, RW, Michejda CJ. Synthesis and Biological Activity of Novel Nonnucleoside Inhibitors of HIV-1 Reverse Transcriptase. 2-Aryl-Substituted Benzimidazoles. Journal of Medicinal Chemistry. 1997 Dec;40(26):4199–207.
  • 18. Pandey J, Tiwari VK, Verma SS, Chaturvedi V, Bhatnagar S, Sinha S, et al. Synthesis and antitubercular screening of imidazole derivatives☆. European Journal of Medicinal Chemistry. 2009 Aug;44(8):3350–5.
  • 19. Singh J, Grover P, Pathak DP. Synthesis, anticonvulsant activity and comparative QSAR study of some novel 1, 2, 5-trisubstituted benzimidazole derivatives. Acta Pharmaceutica Sciencia. 2010;52:511–522.
  • 20. Kandile NG, Mohamed MI, Ismaeel HM. Antiproliferative effects of metal complexes of new isatin hydrazones against HCT116, MCF7 and HELA tumour cell lines. Journal of Enzyme Inhibition and Medicinal Chemistry. 2012 Jun;27(3):330–8.
  • 21. Alaghaz A-NMA, El-Sayed BA, El-Henawy AA, Ammar RAA. Synthesis, spectroscopic characterization, potentiometric studies, cytotoxic studies and molecular docking studies of DNA binding of transition metal complexes with 1,1-diaminopropane–Schiff base. Journal of Molecular Structure. 2013 Mar;1035:83–93.
  • 22. Jiang X-R, Wang P, Smith CL, Zhu BT. Synthesis of Novel Estrogen Receptor Antagonists Using Metal-Catalyzed Coupling Reactions and Characterization of Their Biological Activity. Journal of Medicinal Chemistry. 2013 Apr 11;56(7):2779–90.
  • 23. Wu H, Kong J, Yang Z, Wang X, Shi F, Zhang Y, et al. Copper(II) and manganese(II) picrate complexes with the V-shaped ligand 1,3-bis(1-methylbenzimidazol-2-yl)-2-thiapropane: preparation, structure, DNA-binding properties and antioxidant activities. Transition Metal Chemistry. 2014 Nov;39(8):951–60.
  • 24. Jayamani A, Sengottuvelan N, Chakkaravarthi G. Synthesis, structural, electrochemical, DNA interaction, antimicrobial and molecular docking studies on dimeric copper(II) complexes involving some potential bidentate ligands. Polyhedron. 2014 Oct;81:764–76.
  • 25. El-Gammal OA, Mostafa MM. Synthesis, characterization, molecular modeling and antioxidant activity of Girard′s T thiosemicarbazide and its complexes with some transition metal ions. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2014 Jun;127:530–42.
  • 26. Nakamoto K. Infrared and Raman Spectra of Inorganic and Coordination Compounds. In: Chalmers JM, Griffiths PR, editors. Handbook of Vibrational Spectroscopy [Internet]. Chichester, UK: John Wiley & Sons, Ltd; 2006 [cited 2017 Mar 13]. Available from: http://doi.wiley.com/10.1002/0470027320.s4104
  • 27. Rahaman F, Mruthyunjayaswamy BHM. Synthesis, spectral characterization and biological activity studies of transition metal complexes of Schiff base ligand containing indole moiety. Complex Metals. 2014 Dec 31;1(1):88–95.
  • 28. Ashraf A, Siddiqui WA, Akbar J, Mustafa G, Krautscheid H, Ullah N, et al. Metal complexes of benzimidazole derived sulfonamide: Synthesis, molecular structures and antimicrobial activity. Inorganica Chimica Acta. 2016 Mar;443:179–85.
  • 29. Krishnamurthy G. Synthesis and Characterization of Ruthenium(III) Chloride Complexes with Some 1,2-Disubstituted Benzimidazoles and their Catalytic Activity. Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry. 2011 Jul;41(6):590–7.
  • 30. Munde A, Jagdale A, Jadhav S, Chondhekar T. Synthesis, characterization and thermal study of some transition metal complexes of an asymmetrical tetradentate Schiff base ligand. Journal of the Serbian Chemical Society. 2010;75(3):349–59.
  • 31. Lever ABP. Inorganic electronic spectroscopy. 2nd ed. Amsterdam ; New York: Elsevier; 1984. 863 p. (Studies in physical and theoretical chemistry).
  • 32. Dar AM, Shamsuzzaman, Khan S. Spectroscopic, Viscositic, DNA Binding and Cytotoxic Studies of Newly Synthesized Steroidal Imidazolidines. Journal of Fluorescence. 2016 Mar;26(2):639–49.
  • 33. Bari SB, Adhikari S, Surana S. Tyrosine kinase receptor inhibitors: A new target for anticancer drug development. Journal of PharmaSciTech. 2012;1(2):36–45.
  • 34. Shen L, Chu D. Type II DNA topoisomerases as antibacterial targets. Current Pharmaceutical Design. 1996;2(2):195–208.
  • 35. Yapati H, Devineni SR, Chirumamilla S, Kalluru S. Synthesis, characterization and studies on antioxidant and molecular docking of metal complexes of 1-(benzo[d]thiazol-2-yl)thiourea. Journal of Chemical Sciences. 2016 Jan;128(1):43–51.
  • 36. Yadav G, Ganguly S. Structure activity relationship (SAR) study of benzimidazole scaffold for different biological activities: A mini-review. European Journal of Medicinal Chemistry. 2015 Jun;97:419–43.
There are 36 citations in total.

Details

Subjects Engineering, Chemical Engineering
Journal Section Articles
Authors

Mohammed Shafeeulla This is me

Ganganaik Krishnamurthy This is me

Halehatti S. Bhojynaik This is me

Manjuraj T

Publication Date July 31, 2017
Submission Date April 26, 2017
Acceptance Date July 20, 2017
Published in Issue Year 2017

Cite

Vancouver Shafeeulla M, Krishnamurthy G, Bhojynaik HS, T M. Synthesis, Cytotoxicity and Molecular Docking Study of Complexes Containing Thiazole Moiety. JOTCSA. 2017;4(3):787-810.