Design, synthesis and biological evaluation of new substituted benzofuran-based derivatives via C−H bond activation

Behjat Pouramiri, Mahboobeh Zahedifar, Adileh Ayati, Farah Pouramiri, Mahdiyeh Ahmadi

Abstract


A series of biologically active disubstituted benzofuran derivatives (3a–d) have been designed and synthesized via C-H bond activation reaction. The chemical structures of all final compounds were confirmed by spectroscopic methods. In vitro anti acetylcholinesterase (AChE) activities of these novel compounds were evaluated and showed low to moderate results. Among them, compounds 3d moderately inhibited AChE activities with 68.12 % values.


Keywords


Carbon-carbon coupling, benzofuran, acetylcholinesterase, Alzhei¬mer’s disease

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References


N. C. Berchtold, C. W. Cotman, Neurobiol. Aging. 19 (1998) 173 (https://doi.org/10.1016/S0197-4580(98)00052-9)

W. Thies, L. Bleiler, Alzheimer’s Dement. 9 (2012) 208 (https://doi.org/10.1016/j.jalz.2012.02.001)

H. Feorstl, A. Kurz, Eur Arch Psychiatry Clin Neurosci. 249 (1999) 288 (https://doi.org/10.1007/s004060050101)

C. G. Ballard, N. H. Greig, A. L. Guillozet-Bongaarts, A. Enz, S. Darvesh, Curr. Alz. Res. 2 (2005) 307 (https://doi.org/10.2174/1567205054367838)

A. Mack, A. Robitzki, Prog. Neurobiol. 60 (2000) 607 (https://doi.org/10.1016/S0301-0082(99)00047-7)

L. L. Shen, G. X. Liu, Y. Tang, Acta Pharmacol Sin. 28 (2007) 2053 (https://doi.org/10.1111/j.1745-7254.2007.00664.x)

F. Baharloo, M. H. Moslemin, H. Nadri, A. Asadipour, M. Mahdavi, S. Emami, L. Firouzpour, R. Mohebat,A. Shafiee, A. Foroumadi, Eur. J. Med. Chem. 93 (2015) 196 (https://doi.org/10.1016/j.ejmech.2015.02.009)

J. H. Byun, H. Y. Kim, Y. S. Kim, I. M. Jung, D. J. Kim, W. K. Lee, K. H. Yoo, Bioorg. Med. Chem. Lett. 18 (2008) 5591 (https://doi.org/10.1016/j.bmcl.2008.08.111)

H. Khanam, Shamsuzzaman. Eur. J. Med. Chem. 97 (2015) 483 (https://doi.org/10.1016/j.ejmech.2014.11.039)

W. C. Wan, W. Chen, L. X. Liu, Y. Li, L. J. Yang, X. Y. Deng, H. Bin Zhang, X. D. Yang, Med. Chem. Res. 23 (2014) 1599 (https://doi.org/10.1007/s00044-013-0760-8)

B. F. Abdel-Wahab, H. A. Abdel-Aziz, E. M. Ahmed, Euro. J. Med. Chem. 44 (2009) 2632 (https://doi.org/10.1016/j.ejmech.2008.09.029)

C. K. Ryu, A. L. Song, J. Y. Lee, J. A. Hong, J. H. Yoon, A. Kim, Bioorg. Med. Chem. Lett. 20 (2010) 6777 (https://doi.org/10.1016/j.bmcl.2010.08.129)

P. Yadav, P. Singh, A. K. Tewari, Bioorg. Med. Chem. Lett. 24 (2014) 2251 (https://doi.org/10.1016/j.bmcl.2014.03.087)

Y. Chen, S. Chen, X. Lu, H. Cheng, Y. Oua, H. Cheng, G. C. Zhou, Bioorg. Med. Chem. Lett. , 19 (2009) 1851 (https://doi.org/10.1016/j.bmcl.2009.02.082)

J. P. Corbet, G. Mignani, Chem. Rev. 106 (2006) 2651 (https://doi.org/10.1021/cr0505268)

C. C. C. Johansson Seechurn, M. O. Kitching, T. J. Colacot, V. Snieckus, Angew. Chem. , Int. Ed. 51 (2012) 5062 (https://doi.org/10.1002/anie.201107017)

(a) C. Fischmeister, H. Doucet, Green. Chem. 13 (2011) 741 (https://doi.org/10.1039/C0GC00885K (b) T. W. Lyons, M. S. Sanford, Chem. Rev. 110 (2010) 1147 (https://doi.org/10.1021/cr900184e)

S. L. Tang, R. L. Smith, M. Poliakoff, Green Chem. 7 (2005) 761 (https://doi.org/10.1039/B513020B)

X. Chen, K. M. Engle, D. H. Wang, J. Q. Yu, Angew. Chem. , Int. Ed. 48 (2009) 5094 (b) M. Zhou, R. H. Crabtree, Chem. Soc. Rev. 40 (2011) 1875 (https://doi.org/10.1039/C0CS00099J)

A. Suzuki, Pure. Appl. Chem. 57 (1985) 1749 (https://doi.org/10.1351/pac198557121749)

K. Sonogashira, J. Organometal. Chem. 653 (2002) 46 (https://doi.org/10.1016/S0022-328X(02)01158-0)

R. F. Heck, Org. React. 27 (1982) 345 (https://doi.org/10.1002/0471264180.or027.02)

Y. Nakao, T. Hiyama, Chem. Soc. Rev. 40 (2011) 4893 (https://doi.org/10.1039/C1CS15122C)

E. Negishi, Acc. Chem. Res. 15 (1982) 340 (https://doi.org/10.1021/ar00083a001)

E. Erdik, Tetrahedron, 48 (1992) 9577 (https://doi.org/10.1016/S0040-4020(01)81181-9)

A. Ordentlich, D. Barak, C. Kronman, N. Ariel, Y. Segall, B. Velan, A. Shafferman, J. Biol. Chem. , 273 (1998) 19509 (https://www.jbc.org/content/273/31/19509.long)

F. J. Carvajal, N. C. Inestrosa, Front Mol. Neurosci. 4 (2011) 199 (https://doi.org/10.3389/fnmol.2011.00019)

M. Rosini, E. Simoni, A. Minarini, C. Melchiorre, Neurochem. Res. 39 (2014) 1914 (https://doi.org/10.1007/s11064-014-1250-1)

M. Yoosefian, N. Etminan, A. Juan, E. Mirhaji, RSC Advances 10 (2020) 2650 (https://doi.org/10.1039/C9RA09243A)

G. M. Morris, R. Huey, W. Lindstrom, M. F. Sanner, R. K. Belew, D. S. Goodsell, A. J. Olson, J. Comput. Chem. 30 (2009) 2785 (https://doi.org/10.1002/jcc.21256)

M. Yoosefian, N. Etminan, Amino Acids 50 (2018) 653-661 (https://doi.org/10.1007/s00726-018-2552-4)

B. Pouramiri, M. Mahdavi, S. Moghimi, L. Firoozpour, H. Nadri, A. A. Moradi, E. Tavakolinejad-Kermani, A. Asadipour, A. Foroumadi, Lett. Drug. Des. Discov. 13 (2016) 897-902.

B. Pouramiri, S. Moghimi, M. Mahdavi, H. Nadri, A. Moradi, E. Tavakolinejad‐Kermani, L. Firoozpour, A. Asadipour, A. Foroumadi, Chem. Biol. Drug. Des. 89 (2017) 783 (https://doi.org/10.1111/cbdd.12902)

B. Pouramiri, E. T. Kermani, M. Khaleghi, J. Iran. Chem. Soc. 14 (2017) 2331 (https://doi.org/10.1007/s13738-017-1169-y)

B. Pouramiri, M. Shirvani, E. T. Kermani, J. Serb. Chem. Soc. 82 (2017) 483 (https://doi.org/10.2298/JSC160803034P)

H. Nadri, H. Pirali-Hamedani, M. Shekarchi, M. Abdollahi, V. Sheibani, M. Amanlou, A. Shafiee, A. Foroumadi, Bioorg. Med. Chem. 18 (2010) 6360 (https://doi.org/10.1016/j.bmc.2010.07.012).




DOI: https://doi.org/10.2298/JSC191231039P

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