An effi cient one-pot three-component synthesis and antimicrobial evaluation of tetra substituted thiophene derivatives

Pravinkumar N. Sable Swastika Ganguly Pravin D. Chaudhari

Citation:  Pravinkumar N. Sable, Swastika Ganguly, Pravin D. Chaudhari. An effi cient one-pot three-component synthesis and antimicrobial evaluation of tetra substituted thiophene derivatives[J]. Chinese Chemical Letters, 2014, 25(7): 1099-1103. doi: 10.1016/j.cclet.2014.03.044 shu

An effi cient one-pot three-component synthesis and antimicrobial evaluation of tetra substituted thiophene derivatives

    通讯作者: Pravinkumar N. Sable,
摘要: A convenient one-pot three-component method for the preparation of tetra-substituted thiophene derivatives has been developed. Reaction of acetyl acetone 1, phenyl isothiocynate 2 and 2-chloromethyl derivatives 3a-3c in the presence of potassium carbonate afforded the target compounds, namely ethyl 2-(4-acetyl-3-methyl-5-(phenylamino)thiophen-2-yl)-2-oxoacetate derivatives 4a-4e, ethyl 3-(4-acetyl-3-methyl-5-(phenylamino)thiophen-2-yl)-3-oxopropanoate derivatives 4f-4i, di((4-acetyl-3-methyl-5-phenylamino)thiophen-2-yl)ketone derivatives 4j-4n in reasonable overall yields. The synthesized compounds were screened for antimicrobial activity. The detailed synthesis, spectroscopic data and antimicrobial activities of synthesized compounds were reported.

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    1. [1] A. Dömling, W. Wang, K. Wang, Chemistry and biology of multicomponent reactions, Chem. Rev. 112 (2012) 3083-3135.[1] A. Dömling, W. Wang, K. Wang, Chemistry and biology of multicomponent reactions, Chem. Rev. 112 (2012) 3083-3135.

    2. [2] A. Dömling, Recent developments in isocyanide based multicomponent reactions in applied chemistry, Chem. Rev. 106 (2006) 17-89.[2] A. Dömling, Recent developments in isocyanide based multicomponent reactions in applied chemistry, Chem. Rev. 106 (2006) 17-89.

    3. [3] F.M. Moghaddam, H.Z. Boinee, An efficient and facile one-step synthesis of highly substituted thiophenes, Tetrahedron 60 (2004) 6085-6089.[3] F.M. Moghaddam, H.Z. Boinee, An efficient and facile one-step synthesis of highly substituted thiophenes, Tetrahedron 60 (2004) 6085-6089.

    4. [4] K.I. Molvi, M. Mansuri, V. Sudarsanam, et al., Synthesis, anti-inflammatory, analgesic and antioxidant activities of some tetrasubstituted thiophenes, J. Enzyme Inhib. Med. Chem. 23 (2008) 829-838.[4] K.I. Molvi, M. Mansuri, V. Sudarsanam, et al., Synthesis, anti-inflammatory, analgesic and antioxidant activities of some tetrasubstituted thiophenes, J. Enzyme Inhib. Med. Chem. 23 (2008) 829-838.

    5. [5] M.K. Parai, G. Panda, V. Chaturvedi, Y.K. Manju, S. Sinha, Thiophene containing triarylmethanesasantitubercularagents, Bioorg.Med.Chem.Lett.18(2008)289-292.[5] M.K. Parai, G. Panda, V. Chaturvedi, Y.K. Manju, S. Sinha, Thiophene containing triarylmethanesasantitubercularagents, Bioorg.Med.Chem.Lett.18(2008)289-292.

    6. [6] W. Wardakhan, O. Abdel-Salam, G. Elmegeed, Screening for antidepressant, sedative and analgesic activities of novel fused thiophene derivatives, Acta Pharm. 58 (2008) 1-14.[6] W. Wardakhan, O. Abdel-Salam, G. Elmegeed, Screening for antidepressant, sedative and analgesic activities of novel fused thiophene derivatives, Acta Pharm. 58 (2008) 1-14.

    7. [7] S. Sharma, F. Athar, M.R. Maurya, A. Azam, Copper(II) complexes with substituted thiosemicarbazones of thiophene-2-carboxaldehyde: synthesis, characterization and antiamoebic activity against E. histolytica, Eur. J. Med. Chem. 40 (2005) 1414-1419.[7] S. Sharma, F. Athar, M.R. Maurya, A. Azam, Copper(II) complexes with substituted thiosemicarbazones of thiophene-2-carboxaldehyde: synthesis, characterization and antiamoebic activity against E. histolytica, Eur. J. Med. Chem. 40 (2005) 1414-1419.

    8. [8] O.F. William, Principles of Medicinal Chemistry, 3rd ed., Lippincott Williams & Wilkins Publication, Philadelphia, 1989.[8] O.F. William, Principles of Medicinal Chemistry, 3rd ed., Lippincott Williams & Wilkins Publication, Philadelphia, 1989.

    9. [9] A.A. Sagardoy, M.J. Gil, R. Villar, et al., Benzo[b]thiophene-6-carboxamide 1,1-dioxides: inhibitors of human cancer cell growth at nanomolar concentrations, Bioorg. Med. Chem. 18 (2010) 5701-5707.[9] A.A. Sagardoy, M.J. Gil, R. Villar, et al., Benzo[b]thiophene-6-carboxamide 1,1-dioxides: inhibitors of human cancer cell growth at nanomolar concentrations, Bioorg. Med. Chem. 18 (2010) 5701-5707.

    10. [10] A.A. Fadda, E. Abdel-Latif, R.E. El-Mekawy, Synthesis and molluscicidal activity of some new thiophene, thiadiazole and pyrazole derivatives, Eur. J. Med. Chem. 44 (2009) 1250-1256.[10] A.A. Fadda, E. Abdel-Latif, R.E. El-Mekawy, Synthesis and molluscicidal activity of some new thiophene, thiadiazole and pyrazole derivatives, Eur. J. Med. Chem. 44 (2009) 1250-1256.

    11. [11] Indian Pharmacopoeia, Microbiological Assay of Antibiotics, vol. I, 2007, pp. 45-52.[11] Indian Pharmacopoeia, Microbiological Assay of Antibiotics, vol. I, 2007, pp. 45-52.

    12. [12] C.R. Kokare, Pharmaceutical Microbiology and Biotechnology, 3rd ed., Nirali Prakashan, Pune, 2006, pp. 21.1-21.12.[12] C.R. Kokare, Pharmaceutical Microbiology and Biotechnology, 3rd ed., Nirali Prakashan, Pune, 2006, pp. 21.1-21.12.

    13. [13] Ananthanarayan, Paniker, Textbook of Microbiology, 7th ed., Orient Longman, Chennai, 2005, pp. 628-630.[13] Ananthanarayan, Paniker, Textbook of Microbiology, 7th ed., Orient Longman, Chennai, 2005, pp. 628-630.

    14. [14] Y.J. Huang, A. Dömling, The Gewald multicomponent reaction, Mol. Divers. 15 (2011) 3-33.[14] Y.J. Huang, A. Dömling, The Gewald multicomponent reaction, Mol. Divers. 15 (2011) 3-33.

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  • 收稿日期:  2013-09-11
  • 网络出版日期:  2014-03-04
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