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Synthesis, Spectroscopic Characterization, Crystal structure, Antimicrobial and In Vitro Hemolytic Studies of Some Novel Substituted Thiourea Derivatives

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Abstract

A series of N,N′-disubstituted thioureas, [R–CONHCSNH–R′] where (R = thiophenyl, furonyl, phenyl and R′ = 4-sulphonamido phenyl, pyrimidine-2yl, thiazole-2yl, 3-nitro phenyl, 2-nitro-4-chloro phenyl, 2-chloro-4-nitro phenyl, 2-methoxy-4-nitro phenyl, and 6-phenyl-1,3,5-triazinyl were synthesized, characterized and screened for their antimicrobial activities. The structures of synthesized compounds were established by elemental analysis and spectroscopic techniques (FT-IR, 1H NMR, and 13C NMR). Single crystal study on compounds 1a and 1c have been done. The compound 1a crystallizes in monoclinic space group Cc, with a = 15.2974(5) Å, b = 11.7766(4) Å, c = 8.1059(3) Å, α = 90°, β = 106.31(3)°, γ = 90° and Z = 4 molecules per unit cell, where as compound 1c crystallizes in orthorhombic space group Pbca, with a = 7.6307(6) Å, b = 11.3895(9) Å, c = 24.121(2) Å, α = β = γ = 90° and Z = 8 molecules per unit cell. All the compounds were tested for their inhibitory activities against four human pathogen bacteria and three fungal strains. The screening data revealed that five compounds showed moderate to good activity whereas one of the compound 1k displayed excellent activity. In vitro hemolytic activity of the compounds has shown them to be nontoxic in nature.

Graphical Abstract

Eleven disubstituted thiourea compounds have been synthesized and characterized by elemental analysis, spectroscopic techniques (FT-IR, 1H NMR, and 13C NMR) and single crystal study on two of compounds has been done to understand the proper structural features of the compounds. All the compounds have been screened for their antimicrobial activity; out of them two have shown promising activity against the bacteria and fungi used.

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Acknowledgments

The authors sincerely thanks to Prof. Ray J. Butcher, Department of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, for X-ray data collection. The author Durga Prasad Singh is grateful to BHU for providing UGC-research fellowships. Mr. Mayank Gangwar and Mr. Dharmendra Kumar is thankful to CSIR-New Delhi for providing senior research fellowship.

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Authors and Affiliations

  1. Department of Chemistry, MMV, BHU, Varanasi, 221005, India

    Durga Prasad Singh & Seema Pratap

  2. Department of Microbiology, IMS, BHU, Varanasi, 221005, India

    Mayank Gangwar, Dharmendra Kumar & Gopal Nath

  3. Department of Pharmacology, IMS, BHU, Varanasi, 221005, India

    Mayank Gangwar

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  1. Durga Prasad Singh
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Correspondence to Seema Pratap.

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Singh, D.P., Gangwar, M., Kumar, D. et al. Synthesis, Spectroscopic Characterization, Crystal structure, Antimicrobial and In Vitro Hemolytic Studies of Some Novel Substituted Thiourea Derivatives. J Chem Crystallogr 43, 610–621 (2013). https://doi.org/10.1007/s10870-013-0468-0

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