Novel two step synthesis of bis/Mono 1-aryl-1H-tetrazole-5-carboxylic acid

References

• Hajduk, P. J.; Bures, M.; Praestgaard, J.; Fesik, S. W. Privileged Molecules for Protein Binding Identified from NMR-Based Screening. J. Med. Chem. 2000, 43, 3443–3447. DOI: 10.1021/jm000164q.
   PubMed Web of Science ®Google Scholar
• Bekhit, A. A.; El-Sayed, O. A.; Aboulmagd, E.; Park, J. Y. Tetrazolo[1,5-a]Quinoline as a Potential Promising New Scaffold for the Synthesis of Novel anti-Inflammatory and Antibacterial Agents. Eur. J. Med. Chem. 2004, 39, 249–255. DOI: 10.1016/j.ejmech.2003.12.005.
   PubMed Web of Science ®Google Scholar
• Murali Krishna, S.; Padmalatha, Y.; Ravindranath, L. K. Tetrazoles as a Core Unit Biological Evaluation Agent. Int. J. Med. Pharm. Res. 2015, 3, 1004–1010.
   Google Scholar
• Sidwell, R. W.; Huffman, J. H.; Khare, G. P.; Allen, L. B.; Witkowski, J. T.; Robins, R. K. Broad-Spectrum anti-Viral Activity of Virazole: 1-beta-D-Ribofuranosyl-1,2,4-Triazole-3-Carboxamide. Science 1972, 177, 705–706. DOI: 10.1126/science.177.4050.705.
   PubMed Web of Science ®Google Scholar
• Mohite, P. B.; Bhaskar, V. H. Potential Pharmacological Activities of Tetrazoles in the New Millennium. Int. J. Pharmtech. Res. 2011, 3, 1557–1566.
   Google Scholar
• Hutchinson, D. W.; Naylor, M. The Antiviral Activity of Tetrazole Phosphonic Acids and Their Analogues. Nucl. Acids Res. 1985, 13, 8519–8530. DOI: 10.1093/nar/13.23.8519.
   PubMed Web of Science ®Google Scholar
• Maxwell, J. R.; Wasdahl, D. A.; Wolfson, A. C.; Stenberg, V. I. Synthesis of 5-Aryl-2H- Tetrazoles, 5-Aryl-2H-Tetrazole-2-Acetic Acids, and [(4-Phenyl-5-Aryl-4H-1,2,4-Triazol-3- yl)Thio]Acetic Acids as Possible Superoxide Scavengers and Antiinflammatory Agents. J. Med. Chem. 1984, 27, 1565–1570. DOI: 10.1021/jm00378a007.
   PubMed Web of Science ®Google Scholar
• Bhaskar, V. H.; Mohite, P. B. Design, Synthesis, Characterization and Biological Evaluation of Some Novel 1,5-Disubstituted Tetrazole as Potential anti-Inflammator Agents. J.Optoelectron. Biomed. Mater. 2010, 2, 231–237.
   Google Scholar
• Rajasekaran, A.; Thampi, P. P. Synthesis and Analgesic Evaluation of Some 5-[beta-(10-phenothiazinyl)ethyl]-1-(acyl)-1,2,3,4-tetrazoles. Eur. J. Med. Chem. 2004, 39, 273–279. DOI: 10.1016/j.ejmech.2003.11.016.
   PubMed Web of Science ®Google Scholar
• Maria Dorathi Anu, M.; Jayanthi, M.; Damodar Kumar, S.; Raja, S.; Thirunavukkarasu, S. V. Synthesis, Characterization, Antibacterial & anti- Inflammatory Effects of Substituted Tetrazole Derivatives Based on Different Types of Carbazone and Benzaldehyde. Int. J. Chemtech. Res. 2013, 5, 1982–1990.
   Google Scholar
• Hayao, S.; Havera, H. J.; Strycker, W. G.; Leipzig, T. J.; Rodriguez, R. New Antihypertensive Aminoalkyltetrazoles. J. Med. Chem. 1967, 10, 400–402. DOI: 10.1021/jm00315a025.
   PubMed Web of Science ®Google Scholar
• Abe, T.; Goto, T.; Hattori, Y.; Ito, S.; Kido, K.; Kurahashi, Y.; Maurer, F.; Otsu, Y.; Sawada, H.; Shibuya, K.; et.al. 1-Phenyl-5-Anilinotetrazoles Derivatives, Their Preparation and Their Use as Microbiocides, Insecticides and/or Herbicides. U.S. Patent 5,981,438. 1998.
   Google Scholar
• Le Bourdonnec, B.; Cauvin, C.; Meulon, E.; Yous, S.; Goossens, J. F.; Durant, F.; Houssin, R.; Henichart, J. P. Comparison of 3D Structures and at(1) Binding Properities of Pyrazolidine- 3,5-Diones and Tetrahydropyridazine-3,6-Diones with Parent Antihypertensive Drug Irbesartan. J. Med. Chem. 2002, 45, 4794–4798. DOI: 10.1021/jm010457z.
   PubMed Web of Science ®Google Scholar
• Ostrovskii, V. A.; Trifonov, R. E.; Popova, E. A. Medicinal Chemistry of Tetrazoles. Russ. Chem. Bull. 2012, 61, 768–780. DOI: 10.1007/s11172-012-0108-4.
   Web of Science ®Google Scholar
• Hansch, C.; Kurup, A.; Garg, R.; Gao, H. Chem-Bioinformatics and QSAR: A Review of QSAR Lacking Positive Hydrophobic Terms. Chem. Rev. 2001, 101, 619–672. DOI: 10.1021/cr0000067.
   PubMed Web of Science ®Google Scholar
• Mathvink, R. J.; Samuel Tolman, J.; Chitty, D.; Candelore, R. M.; Cascieri, M. A.; Colwell, L. F. Jr.; Deng, L.; Feeney, W. P.; Forrest, M. J.; Hom, G. J.; et al. Potent Selective 3-Pyridylethanolamine β3 Adrenergic Receptor Agonists Possessing a Thiazolebenzenesulfonamide Pharmacophore. Bioorganic Med. Chem. Lett. 2000, 10, 1971–1973. DOI: 10.1016/S0960-894X(00)00390-5.
   PubMed Web of Science ®Google Scholar
• Chung, J. Y. L.; Ho, G. J.; Chartrain, M.; Roberge, C.; Zhao, D. L.; Leazer, J.; Farr, R.; Robbins, M.; Emerson, K.; Mathre, D. J.; et al. The Chemistry of Hydroxylamines, Oximes and Hydroxamic Acids. Tetrahedron Lett. 1999, 40, 6739. DOI: 10.1016/S0040-4039(99)01353-2.
   Google Scholar
• Nathaniel, R.; Mineva, T.; Nikolova, R.; Bojilova, A. Density Functional Study of the Interaction of 3-(ω-Bromoacetyl) Coumarin with Phosphites. Int. J. Quantum Chem. 2006, 106, 1357–1366. DOI: 10.1002/qua.20893.
   Web of Science ®Google Scholar
• Jursic, B. S.; Zdravkovski, Z. Theoretical Study of Benzofusedthieno [3,2-b] Furans in the Reaction with Electrophiles. Int. J. Quantum Chem. 1995, 54, 161. DOI: 10.1002/qua.560540304.
   Google Scholar
• Bohórquez, H. J.; Boyd, R. J.; Matta, C. F. Molecular Model with Quantum Mechanical Bonding Information. J. Phys. Chem. A. 2011, 115, 12991. DOI: 10.1021/jp204100z.
   PubMed Web of Science ®Google Scholar
• Bader, R. F. W. In Atoms in Molecules: A Quantum Theory; Clarendon Press: Oxford, UK, 1990.
   Google Scholar
• Grabowski, S. J. What Is the Covalency of Hydrogen Bonding. Chem. Rev. 2011, 111, 2597–2625. DOI: 10.1021/cr800346f.
   PubMed Web of Science ®Google Scholar
• Bader, R. F. W. A Quantum Theory of Molecular Structure and Its Application. Chem. Rev. 1991, 91, 893–928. DOI: 10.1021/cr00005a013.
   Web of Science ®Google Scholar
• Bader, R. F. W. The Quantum Mechanical Basis of Conceptual Chemistry. Monatshefte Für Chemie 2005, 136, 819–854. DOI: 10.1007/s00706-005-0307-x.
   Web of Science ®Google Scholar
• Bader, R. F. W. Atoms in Molecules. Acc. Chem. Res. 1985, 18, 9–15. DOI: 10.1021/ar00109a003.
   Web of Science ®Google Scholar
• Bader, R. F. W. Atoms in Molecules: A Quantum Theory; Oxford University press: Oxford, UK, 1990.
   Google Scholar
• Grabowski, S. J.; Sokalski, W. A.; Leszczynski, J. Nature of X-H+5-−5H-Y Dihydrogen Bonds and X-H-σ Interactions. J. Phys. Chem. A. 2004, 108, 5823–5830. DOI: 10.1021/jp049874o.
   Web of Science ®Google Scholar
• Popelier, P. L. A. Charactreization of a Dihydrogen Bond on the Basis of the Electron Density. J. Phys. Chem. A. 1998, 102, 1873–1878. DOI: 10.1021/jp9805048.
   Web of Science ®Google Scholar
• Arputharaj, D. S.; Hathwar, V. R.; Row, T. N. G.; Kumaradhas, P. Topological Electron Density Analysis and Electrostatic Properties of Aspirin; An Experimental and Theoretical Study. Cryst. Growth Des. 2012, 12, 4357–4366. DOI: 10.1021/cg300269n.
   Web of Science ®Google Scholar
• Parthasarathi, R.; Subramanian, V.; Sathyamurthy, N. Hydrogen Bonding without Borders: An Atoms-In-Molecules Perspective. J. Phys. Chem. A. 2006, 110, 3349–3351. DOI: 10.1021/jp060571z.
   PubMed Web of Science ®Google Scholar
• Pearson, R. G. Absolute Electronegativity and Absolute Hardness of Lewis Acid and Bases. J. Am. Chem. Soc. 1985, 107, 6801–6806. DOI: 10.1021/ja00310a009.
   Web of Science ®Google Scholar
• Parr, R. G.; Pearson, R. G. Absolute Hardness: Companion Parameters to Absolute Electronegativity. J. Am. Chem. Soc. 1983, 105, 7512–7516. DOI: 10.1021/ja00364a005.
   Web of Science ®Google Scholar
• Pearson, R. G. Chemical Hardness and Density Functional Theory. J. Chem. Sci. 2005, 117, 369–377. DOI: 10.1007/BF02708340.
   Web of Science ®Google Scholar
• Filarowski, A.; Majerz, I. Aim Analysis of Intramolecular Hydrogen Bonding in O-hydroxy aryl Schiff bases. J. Phys. Chem. A. 2008, 112, 3119–3126. DOI: 10.1021/jp076253x.
   PubMed Web of Science ®Google Scholar
• Shanmugam, G.; Bhakiaraj, D.; Elavarasan, S.; Elavarasan, T.; Gopalakrishnan, M. Benign by Design Synthesis of Novel 1H-Tetrazoles: Spectral Characterization and Antibacterial Activities. Chem. Sci. Trans. 2013, 2, 1304–1311.
   Google Scholar
• Myznikov, L. V.; Hrabalek, A.; Koldobskii, G. I. Drugs in Tetrazole Series. Chem. Heterocycl. Compd. 2007, 43, 1–9. DOI: 10.1007/s10593-007-0001-5.
   Google Scholar