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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 50, 2020 - Issue 6
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ARTICLES

N-Mannich bases of benzimidazole as a potent antitubercular and antiprotozoal agents: Their synthesis and computational studies

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Pages 858-878 | Received 09 Dec 2019, Published online: 14 Feb 2020

References

  • Enciso, E.; Sarmiento-Sánchez, J. I.; López-Moreno, H. S.; Ochoa-Terán, A.; Osuna-Martínez, U.; Beltrán-López, E. Synthesis of New Quinazolin-2, 4-Diones as anti-Leishmania mexicana Agents. Mol. Divers. 2016, 20, 821–828. DOI: 10.1007/s11030-016-9693-8.
  • Patel, N. B.; Patel, J. N.; Purohit, A. C.; Patel, V. M.; Rajani, D. P.; Moo-Puc, R.; Lopez-Cedillo, J. C.; Nogueda-Torres, B.; Rivera, G. In Vitro and in Vivo Assessment of Newer Quinoxaline–Oxadiazole Hybrids as Antimicrobial and Antiprotozoal Agents. Int. J. Antimicrob. Agents. 2017, 50, 413–418. DOI: 10.1016/j.ijantimicag.2017.04.016.
  • World Health Organization. Global tuberculosis report 2019. In Global tuberculosis report 2019, 2019.
  • Ahirrao, P. Recent Developments in Antitubercular Drugs. MRMC. 2008, 8, 1441–1451. DOI: 10.2174/138955708786786516.
  • Luckner, S. R.; Liu, N.; Am Ende, C. W.; Tonge, P. J.; Kisker, C. A Slow, Tight Binding Inhibitor of InhA, the Enoyl-Acyl Carrier Protein Reductase from Mycobacterium tuberculosis. J. Biol. Chem. 2010, 285, 14330–14337. DOI: 10.1074/jbc.M109.090373.
  • Patel, V. M.; Patel, N. B.; Chan-Bacab, M. J.; Rivera, G. Synthesis, Biological Evaluation and Molecular Dynamics Studies of 1, 2, 4-Triazole Clubbed Mannich Bases. Comput. Biol. Chem. 2018, 76, 264–274. DOI: 10.1016/j.compbiolchem.2018.07.020.
  • Khan, I.; Patel, N. B.; Patel, V. M. Synthesis, in Silico Molecular Docking and Pharmacokinetic Studies, in Vitro Antimycobacterial and Antimicrobial Studies of New Imidozolones Clubbed with Thiazolidinedione. CAD. 2018, 14, 269–283. DOI: 10.2174/1573409914666180516113552.
  • Spasov, A.; Yozhitsa, I.; Bugaeva, L.; Anisimova, V. Benzimidazole Derivatives: Spectrum of Pharmacological Activity and Toxicological Properties (a Review). Pharm. Chem. J. 1999, 33, 232–243. DOI: 10.1007/BF02510042.
  • Saha, P.; Ramana, T.; Purkait, N.; Ali, M. A.; Paul, R.; Punniyamurthy, T. Ligand-Free Copper-Catalyzed Synthesis of Substituted Benzimidazoles, 2-Aminobenzimidazoles, 2-Aminobenzothiazoles, and Benzoxazoles. J. Org. Chem. 2009, 74, 8719–8725. DOI: 10.1021/jo901813g.
  • Wang, H.; Wang, Y.; Peng, C.; Zhang, J.; Zhu, Q. A Direct Intramolecular C − H Amination Reaction Cocatalyzed by Copper (II) and Iron (III) as Part of an Efficient Route for the Synthesis of Pyrido [1, 2-a] Benzimidazoles from N-Aryl-2-Aminopyridines. J. Am. Chem. Soc. 2010, 132, 13217–13219. DOI: 10.1021/ja1067993.
  • Saify, Z. S.; Kamil, A.; Akhtar, S.; Taha, M.; Khan, A.; Khan, K. M.; Jahan, S.; Rahim, F.; Perveen, S.; Choudhary, M. I. 2-(2′-Pyridyl) Benzimidazole Derivatives and Their Urease Inhibitory Activity. Med. Chem. Res. 2014, 23, 4447–4454. DOI: 10.1007/s00044-014-1015-z.
  • Lu, J.; Yang, B.; Bai, Y. Microwave Irradiation Synthesis of 2-Substituted Benzimidazoles Using PPA as a Catalyst under Solvent-Free Conditions. Synth. Commun. 2002, 32, 3703–3709. DOI: 10.1081/SCC-120015381.
  • VanVliet, D. S.; Gillespie, P.; Scicinski, J. J. Rapid One-Pot Preparation of 2-Substituted Benzimidazoles from 2-Nitroanilines Using Microwave Conditions. Tetrahedron Lett. 2005, 46, 6741–6743. DOI: 10.1016/j.tetlet.2005.07.130.
  • Demirayak, S.; Kayagil, I.; Yurttas, L. Microwave Supported Synthesis of Some Novel 1, 3-Diarylpyrazino [1, 2-a] Benzimidazole Derivatives and Investigation of Their Anticancer Activities. Eur. J. Med. Chem. 2011, 46, 411–416. DOI: 10.1016/j.ejmech.2010.11.007.
  • Menteşe, E.; Bektaş, H.; Ülker, S.; Bekircan, O.; Kahveci, B. Microwave-Assisted Synthesis of New Benzimidazole Derivatives with Lipase Inhibition Activity. J. Enzyme Inhib. Med. Chem. 2014, 29, 64–68. DOI: 10.3109/14756366.2012.753880.
  • Shah, K.; Chhabra, S.; Shrivastava, S. K.; Mishra, P. Benzimidazole: A Promising Pharmacophore. Med. Chem. Res. 2013, 22, 5077–5104. DOI: 10.1007/s00044-013-0476-9.
  • Noolvi, M.; Agrawal, S.; Patel, H.; Badiger, A.; Gaba, M.; Zambre, A. Synthesis, Antimicrobial and Cytotoxic Activity of Novel Azetidine-2-One Derivatives of 1H-Benzimidazole. Arab. J. Chem. 2014, 7, 219–226. DOI: 10.1016/j.arabjc.2011.02.011.
  • Tonelli, M.; Simone, M.; Tasso, B.; Novelli, F.; Boido, V.; Sparatore, F.; Paglietti, G.; Pricl, S.; Giliberti, G.; Blois, S. Antiviral Activity of Benzimidazole Derivatives. II. Antiviral Activity of 2-Phenylbenzimidazole Derivatives. Bioorg. Med. Chem. 2010, 18, 2937–2953. DOI: 10.1016/j.bmc.2010.02.037.
  • Navarrete-Vázquez, G.; Cedillo, R.; Hernández-Campos, A.; Yépez, L.; Hernández-Luis, F.; Valdez, J.; Morales, R.; Cortés, R.; Hernández, M.; Castillo, R. Synthesis and Antiparasitic Activity of 2-(Trifluoromethyl) Benzimidazole Derivatives. Bioorg. Med. Chem. Lett. 2001, 11, 187–190. DOI: 10.1016/S0960-894X(00)00619-3.
  • El, A. R.; Aboul-Enein, H. Y. Benzimidazole Derivatives as Potential Anticancer Agents. Mini Rev. Med. Chem. 2013, 13, 399–407.
  • Iwahi, T.; Satoh, H.; Nakao, M.; Iwasaki, T.; Yamazaki, T.; Kubo, K.; Tamura, T.; Imada, A. Lansoprazole, a Novel Benzimidazole Proton Pump Inhibitor, and Its Related Compounds Have Selective Activity against Helicobacter pylori. Antimicrob. Agents Chemother. 1991, 35, 490–496. DOI: 10.1128/AAC.35.3.490.
  • Abdel‐Aziz, H. A.; Gamal‐Eldeen, A. M.; Hamdy, N. A.; Fakhr, I. M. Immunomodulatory and Anticancer Activities of Some Novel 2‐Substituted‐6‐Bromo‐3‐Methylthiazolo [3, 2‐a] Benzimidazole Derivatives. Arch. Pharm. Chem. Life. Sci. 2009, 342, 230–237. DOI: 10.1002/ardp.200800189.
  • Sircar, J. C.; Richards, M. L. Benzimidazole compounds for modulating IgE and inhibiting cellular proliferation. Google Patents: 2007.
  • Selvakumar, S.; Babu, I. S.; Chidambaranathan, N. In-Vivo Central Nervous System-Locomotor Activity of Some Synthesized 2-[(1-((Phenyl Amino) Methyl) Substituted 1-Benzoimidazol-2-yl) Alkyl] Isoindoline-1, 3-Diones. Biosci, Biotechnol. Res. Asia 2013, 10, 937–943. DOI: 10.13005/bbra/1222.
  • El-Masry, A.; Fahmy, H.; Ali Abdelwahed, S. Synthesis and Antimicrobial Activity of Some New Benzimidazole Derivatives. Molecules 2000, 5, 1429–1438. DOI: 10.3390/51201429.
  • Xu, Z.; Zhang, S.; Gao, C.; Fan, J.; Zhao, F.; Lv, Z.-S.; Feng, L.-S. Isatin Hybrids and Their anti-Tuberculosis Activity. Chin. Chem. Lett. 2017, 28, 159–167. DOI: 10.1016/j.cclet.2016.07.032.
  • Taher, A. T.; Khalil, N. A.; Ahmed, E. M. Synthesis of Novel Isatin-Thiazoline and Isatin-Benzimidazole Conjugates as anti-Breast Cancer Agents. Arch. Pharm. Res. 2011, 34, 1615–1621. DOI: 10.1007/s12272-011-1005-3.
  • Shinegare, M.; Mane, D.; Shinde, D.; Thore, S.; Bhawsar, S. Synthesis of Mannich Bases of Benzimidazole as Possible Antiviral Agents. Asian J. Chem. 1996, 8, 225.
  • Jesudason, E. P.; Sridhar, S.; Malar, E. P.; Shanmugapandiyan, P.; Inayathullah, M.; Arul, V.; Selvaraj, D.; Jayakumar, R. Synthesis, Pharmacological Screening, Quantum Chemical and in Vitro Permeability Studies of N-Mannich Bases of Benzimidazoles through Bovine Cornea. Eur. J. Med. Chem. 2009, 44, 2307–2312. DOI: 10.1016/j.ejmech.2008.03.043.
  • Kumar, S. V.; Subramanian, M. R.; Chinnaiyan, S. K. Synthesis, Characterisation and Evaluation of N-Mannich Bases of 2-Substituted Benzimidazole Derivatives. J. Young Pharm. 2013, 5, 154–159. DOI: 10.1016/j.jyp.2013.11.004.
  • A Datar, P.; A Limaye, S. Design and Synthesis of Mannich Bases as Benzimidazole Derivatives as Analgesic Agents. AIAAMC. 2015, 14, 35–46. DOI: 10.2174/1871523014666150312164625.
  • He, X.; Alian, A.; Stroud, R.; Ortiz de Montellano, P. R. Pyrrolidine Carboxamides as a Novel Class of Inhibitors of Enoyl Acyl Carrier Protein Reductase from Mycobacterium tuberculosis. J. Med. Chem. 2006, 49, 6308–6323. DOI: 10.1021/jm060715y.
  • Aparna, Y.; Sharada, L.; Subhashini, N.; Sreekanth, S. Synthesis, Characterization, Molecular Docking, and Antimicrobial Activity of New Arylidene-Substituted Imidazoles. Russ. J. Gen. Chem. 2019, 89, 1202–1208. DOI: 10.1134/S1070363219060161.
  • Lima, C. H. d S.; de Alencastro, R. B.; Kaiser, C. R.; de Souza, M. V. N.; Rodrigues, C. R.; Albuquerque, M. G. Aqueous Molecular Dynamics Simulations of the M. tuberculosis enoyl-ACP reductase-NADH System and Its Complex with a Substrate Mimic or Diphenyl Ethers Inhibitors. IJMS. 2015, 16, 23695–23722. DOI: 10.3390/ijms161023695.
  • Bijukumar, G.; Maloyesh, B.; Bhaskar, B. S.; Rajendra, A. Efficient Synthesis of Cinacalcet Hydrochloride. Synth. Commun. 2008, 38, 1512–1517. DOI: 10.1080/00397910801928541.

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