Current Science

Open Access Open Access  Restricted Access Subscription Access

Exploring Effective Factors on Energy Data of Some Benzofuran Derivatives


Affiliations
1 Department of Chemistry, University of Zabol, P.O. Box 98615-538, Zabol, Iran, Islamic Republic of
2 Department of Chemistry, Karaj Branch, Islamic Azad University of Karaj, Karaj, Iran, Islamic Republic of
 

Benzofuran derivatives have many useful applications. Computational quantum chemistry method was used to study the relationship between energy data and molecular properties of the 5,6-dihydroxy-2-methyl-1-benzofuran-3-carboxylate derivatives (molecules 3a–3f). Results indicate that there is a good relationship between intramolecular hydrogen bond lengths and energy data of these molecules. Also, X-ray of molecule 3e was used to compare experimental and computational geometrical parameters. Chemical hardness, chemical potential and electronegativity values were calculated to recognize relation between energy data and reactivity of these molecules. Atomic net charges and molecular electrostatic potential values were employed for better insight regarding energy data of the molecules. Electronic charge densities were calculated using atoms in molecules method. The correlation coefficients between experimental and computational 13C NMR chemical shifts were examined. Total spin– spin coupling constant and its components were evaluated to understand the contribution of these properties in energy data of the molecules. The relation between energy data of the molecules and aromaticity of the rings was also determined.

Keywords

Benzofuran, Computational Quantum Chemistry, Energy Data, Molecular Properties.
User
Notifications
Font Size

  • Lee, S. K., Cui, B., Mehta, R. R., Kinghorn, A. D. and Pezzuto, J. M., Cytostatic mechanism and antitumor potential of novel 1Hcyclopenta[ b]benzofuran lignans isolated from Aglaia elliptica. Chem. Biol. Interact., 1998, 115, 215–228.

  • Janprasert, J., Satasook, C., Sukumalanand, P., Champagne, D. E., Isman, M. B. and Wiriyachitra, P., Rocaglamide, a natural benzofuran insecticide from Aglaia odorata. Phytochemistry, 1992, 32, 67–69.

  • Sundaram, R., Ganesan, R. and Murugesan, G., In vitro antiplasmodial activity of spiro benzofuran compound from mangrove plant of southern India. Asian Pac. J. Trop. Med., 2012, 5, 358–361.

  • Jiang, X., Liu, W., Zhang, W., Jiang, F., Gao, Z. and Zhuang, H., Synthesis and antimicrobial evaluation of new benzofuran derivatives. Eur. J. Med. Chem., 2011, 46, 3526–3530.

  • Shankerrao, S., Bodke, Y. D. and Santoshkumar, S., Synthesis and antimicrobial activity of some imidazothiazole derivatives of Benzofuran. Arab. J. Chem., doi:org/10.1016/j.arabjc.2012.10.018.

  • Kirilmis, C., Ahmedzade, M., Servi, S., Koca, M., Kizirgil, A. and Kazaz, C., Synthesis and antimicrobial activity of some novel derivatives of benzofuran: Part 2. The synthesis and antimicrobial activity of some novel 1-(1-benzofuran-2-yl)-2-mesitylethanone derivatives. Eur. J. Med. Chem., 2008, 43, 300–308.

  • Malpani, Y. et al., Efficient synthesis of 3H,3'H-spiro[benzofuran-2,1'-isobenzofuran]-3,3'-dione as novel skeletons specifically for influenza virus type B inhibition. Eur. J. Med. Chem., 2013, 62, 534–544.

  • Rangaswamy, J., Kumar, H. V., Harini, S. T. and Naik, N., Synthesis of benzofuran based 1,3,5-substituted pyrazole derivatives: as a new class of potent antioxidants and antimicrobials-A novel accost to amend biocompatibility. Bioorg. Med. Chem. Lett., 2012, 22, 4773–4777.

  • Rangaswamy, J., Kumar, H. V., Harini, S. T. and Naik, N., Functionalized 3-(benzofuran-2-yl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole scaffolds: a new class of antimicrobials and antioxidants. Arab. J. Chem., doi:org/10.1016/j.arabjc.2013.10.012.

  • Galal, S. A., Abd El-All, A. S., Abdallah, M. M. and El-Diwani, H. I., Synthesis of potent antitumor and antiviral benzofuran derivatives. Bioorg. Med. Chem. Lett., 2009, 19, 2420–2428.

  • Ono, M., Kung, M. P., Hou, C. and Kung, H. F., Benzofuran derivatives as Aβ-aggregate-specific imaging agents for Alzheimer’s disease. Nucl. Med. Biol., 2002, 29, 633–642.

  • Dawood, K. M., Abdel-Gawad, H., Rageb, E. A., Ellithey, M. and Mohamed, H. A., Synthesis, anticonvulsant and anti-inflammatory evaluation of some new benzotriazole and benzofuran-based heterocycles. Bioorg. Med. Chem., 2006, 14, 3672–3680.

  • Radadiya, A. and Shah, A., Bioactive benzofuran derivatives: an insight on lead developments, radioligands and advances of the last decade. Eur. J. Med. Chem., 2015, 97, 356–376.

  • Hiremathad, A., Patil, M. R., Chand, C. K. R. K., Santos, M. A. and Keri, R. S., Benzofuran: an emerging scaffold for antimicrobial agents. RSC Adv., 2015, 5, 96809–96828.

  • Nevagi, R. J., Dighe, S. N. and Dighe, S. N., Biological and medicinal significance of benzofuran. Eur. J. Med. Chem., 2015, 97, 561–581.

  • Masataka, F., Nobuo, M., Tsutomu, H. and Tomihiro, N., Antioxidant activities of vitamin E derivative having benzofuran skeleton. Nippon Kagakkai Koen Yokoshu, 2002, 81, 1381.

  • Rizzo, S., Rivière, C., Piazzi, L., Bisi, A., Gobbi, S. and Bartolini, M., Benzofuran-based hybrid compounds for the inhibition of cholinesterase activity, beta amyloid aggregation, and abeta neurotoxicity. J. Med. Chem., 2008, 51, 2883–2886.

  • Shamsuzzaman, H. K., Bioactive benzofuran derivatives: a review. Eur. J. Med. Chem., 2015, 97, 483–504.

  • Pan, F. and Wiese, G. A., The synthesis and antifungal studies of some benzofuran compounds. J. Am. Pharm. Assoc., 1960, 49, 259–264.

  • Habermann, J., Ley, S. V. and Smits, R., Three-step synthesis of an array of substituted benzofurans using polymer-supported reagents. J. Chem. Soc., Perkin Trans., 1999, 1, 2421–2423.

  • Galal, S. A., Abd El-All, A. S., Abdallah, M. M. and El-Diwani, H. I., Synthesis of potent antitumor and antiviral benzofuran derivatives. Bioorg. Med. Chem. Lett., 2009, 19, 2420–2428.

  • Takahashi, M., Nakano, K. and Nozaki, K., Synthesis and properties of benzophospholo[3,2-b]benzofuran derivatives. J. Org. Chem., 2015, 80, 3790–3797.

  • Fakhari, A. R., Nematollahi, D., Shamsipur, M., Makarem, S., Hosseini Davarani, S. S., Alizadeh, A. and Khavasi, H. R., Electrochemical synthesis of 5,6-dihydroxy-2-methyl-1-benzofuran3-carboxylate derivatives. Tetrahedron, 2007, 63, 3894–3898.

  • Santana, L. et al., AM1 theoretical study, synthesis and biological evaluation of some benzofuran analogues of anti-inflammatory arylalkanoic acids. Eur. J. Pharm. Sci., 1999, 7, 161–166.

  • Islam, M. M. et al., Synthesis, structural properties, electrophilic substitution reactions and DFT computational studies of calix[3] benzofurans. RSC Adv., 2016, 6, 50808–50817.

  • Ramos, F., Flores, H., Rojas, A., Hernandez-Perez, J. M., Camarillo, E. A. and Amador, M. P., Experimental and computational thermochemical study of benzofuran, benzothiophene and indole derivatives. J. Chem. Thermodyn., 2016, 97, 297–306.

  • Swamy, P. M. G., Prasad, Y. R., Ashvini, H. M., Giles, D., Shashidhar, B. V. and Agasimundin, Y. S., Synthesis, anticancer and molecular docking studies of benzofuran derivatives. Med. Chem. Res., 2015, 24, 3437–3452.

  • Moorthy, N. S. H. N., Sousa, S. F., Ramos, M. J. and Fernandes, P. A., Structural feature study of benzofuran derivatives as farnesyltransferase inhibitors. J. Enzyme Inhibit. Med. Chem., 2011, 26, 777–791.

  • Frisch, M. et al., Gaussian 09, Revision A. 1. Gaussian, Inc., Wallingford CT, USA, 2009.

  • Breneman, C. M. and Wiberg, K. B., Determining atom-centered monopoles from molecular electrostatic potentials – the need for high sampling density in formamide conformational analysis. J. Comput. Chem., 1990, 11, 361–373.

  • Bader, R. F. W., Atoms in Molecules: A Quantum Theory, Oxford University Press, Oxford, UK, 1990.


Abstract Views: 381

PDF Views: 119




  • Exploring Effective Factors on Energy Data of Some Benzofuran Derivatives

Abstract Views: 381  |  PDF Views: 119

Authors

Pouya Karimi
Department of Chemistry, University of Zabol, P.O. Box 98615-538, Zabol, Iran, Islamic Republic of
Somayeh Makarem
Department of Chemistry, Karaj Branch, Islamic Azad University of Karaj, Karaj, Iran, Islamic Republic of
Hamid Ahmar
Department of Chemistry, University of Zabol, P.O. Box 98615-538, Zabol, Iran, Islamic Republic of

Abstract


Benzofuran derivatives have many useful applications. Computational quantum chemistry method was used to study the relationship between energy data and molecular properties of the 5,6-dihydroxy-2-methyl-1-benzofuran-3-carboxylate derivatives (molecules 3a–3f). Results indicate that there is a good relationship between intramolecular hydrogen bond lengths and energy data of these molecules. Also, X-ray of molecule 3e was used to compare experimental and computational geometrical parameters. Chemical hardness, chemical potential and electronegativity values were calculated to recognize relation between energy data and reactivity of these molecules. Atomic net charges and molecular electrostatic potential values were employed for better insight regarding energy data of the molecules. Electronic charge densities were calculated using atoms in molecules method. The correlation coefficients between experimental and computational 13C NMR chemical shifts were examined. Total spin– spin coupling constant and its components were evaluated to understand the contribution of these properties in energy data of the molecules. The relation between energy data of the molecules and aromaticity of the rings was also determined.

Keywords


Benzofuran, Computational Quantum Chemistry, Energy Data, Molecular Properties.

References





DOI: https://doi.org/10.18520/cs%2Fv114%2Fi10%2F2092-2098