Summary.
The antimicrobial activity of six N-phenyl- and fourteen N-benzoylthiourea derivatives were evaluated from their Minimal Inhibitory Concentration (MIC) values using the microdilution procedure against ten microorganisms. Most of the compounds exhibited selective activity against fungi and Gram-positive bacteria, which were very effectively inhibited by some of the tested thioureas. Additionally, SAR considerations and four novel X-ray diffraction structures of N-benzoylthioureas are included.
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JA Heinemann RG Ankenbauer CF Amabile-Cuevas (2000) Drug Discov Today 5 195 Occurrence Handle10790263 Occurrence Handle10.1016/S1359-6446(00)01483-5 Occurrence Handle1:CAS:528:DC%2BD3cXislegsr4%3D
K Long M Boyce H Lin J Yuan D Ma (2005) Bioorg Med Chem Lett 15 3849 Occurrence Handle16002288 Occurrence Handle10.1016/j.bmcl.2005.05.120 Occurrence Handle1:CAS:528:DC%2BD2MXntVyntb8%3D
TK Venkatachalam S Qazi P Samuel FM Uckun (2003) Bioorg Med Chem Lett 13 485 Occurrence Handle12565956 Occurrence Handle10.1016/S0960-894X(02)00992-7 Occurrence Handle1:CAS:528:DC%2BD3sXptFamuw%3D%3D
C Sun H Huang M Feng X Shi X Zhang P Zhou (2006) Bioorg Med Chem Lett 16 162 Occurrence Handle16216505 Occurrence Handle10.1016/j.bmcl.2005.09.033 Occurrence Handle1:CAS:528:DC%2BD2MXht1Citr%2FN
GM Coppola RE Damon JB Eskesen DS France JR Paterniti SuffixJr (2005) Bioorg Med Chem Lett 15 809 Occurrence Handle15664862 Occurrence Handle10.1016/j.bmcl.2004.10.094 Occurrence Handle1:CAS:528:DC%2BD2MXnsVOjug%3D%3D
GG Muccioli J Wouters GKE Scriba W Poppitz JH Poupaert DM Lambert (2005) J Med Chem 48 7486 Occurrence Handle16279809 Occurrence Handle10.1021/jm0503906 Occurrence Handle1:CAS:528:DC%2BD2MXhtFalu7vO
T Phuong T Khac-Minh NTV Ha HTN Phuong (2004) Bioorg Med Chem Lett 14 653 Occurrence Handle14741262 Occurrence Handle10.1016/j.bmcl.2003.11.044
TJ Egan KR Koch PL Swan C Clarkson DAV Schalkwyk PJJ Smith (2004) J Med Chem 47 2926 Occurrence Handle15139771 Occurrence Handle10.1021/jm031132g Occurrence Handle1:CAS:528:DC%2BD2cXjsVSlsbo%3D
TK Venkatachalam EA Sudbeck C Mao FM Uckun (2000) Bioorg Med Chem Lett 10 2071 Occurrence Handle10999473 Occurrence Handle10.1016/S0960-894X(00)00398-X Occurrence Handle1:CAS:528:DC%2BD3cXmtF2htro%3D
TK Venkatachalam C Mao FM Uckun (2004) Bioorg Med Chem 12 4275 Occurrence Handle15246104 Occurrence Handle10.1016/j.bmc.2004.04.050 Occurrence Handle1:CAS:528:DC%2BD2cXls1Wnuro%3D
TK Venkatachalam C Mao FM Uckun (2004) Biochem Pharmacol 67 1933 Occurrence Handle15130770 Occurrence Handle10.1016/j.bcp.2004.01.019 Occurrence Handle1:CAS:528:DC%2BD2cXjvVCju70%3D
TK Venkatachalam FM Uckun (2004) Synth Commun 34 2451 Occurrence Handle10.1081/SCC-120039499 Occurrence Handle1:CAS:528:DC%2BD2cXlslCms7k%3D
S Cunha SM Oliveira MT Rodrigues SuffixJr RM Bastos J Ferrari CMA Oliveira L Kato HB Napolitano I Vencato C Lariucci (2005) J Mol Struct 752 32 Occurrence Handle10.1016/j.molstruc.2005.05.016 Occurrence Handle1:CAS:528:DC%2BD2MXhtVamsbfP
UA Baltabaev AG Makhsumov UB Zakirov ID Babaev K Shukurullaev (2002) Pharm Chem J 36 77 Occurrence Handle10.1023/A:1016007929976 Occurrence Handle1:CAS:528:DC%2BD38XkvFaqu70%3D
BP Yadava (1989) Curr Sci 58 1026 Occurrence Handle1:CAS:528:DyaK3cXhslSqsbs%3D
For representative papers on synthesis, see: (a) Kascheres A, Ueno M (1991) J Heterocyclic Chem 28: 2057; (b) Sarkis GY, Faisal ED (1985) J Heterocyclic Chem 22: 137; (c) Rasmussen CR, Villani FJ Jr, Weaner LE, Reynolds BE, Hood AR, Hecker LR, Nortey SO, Hanslin A, Costanzo MJ, Powell ET, Molinari AJ (1988) Synthesis 456; (d) Ciszewski L, Xu D, Repic O, Blacklock TJ (2004) Tetrahedron Lett 45: 8091; (e) Katritzky AR, Kirichenko N, Rogovoy BV, Kister J, Tao H (2004) Synthesis 1799; (f) Vásquez J, Bernès S, Reyes Y, Moya M, Sharma P, Alvarez C, Gutiérrez R (2004) Synthesis 1955; (g) Katritzky AR, Ledoux S, Witek RM, Nair SK (2004) J Org Chem 69: 2976; (h) Herr RJ, Kuhler JL, Meckler H, Opalka CJ (2000) Synthesis 1569; (i) Plutin AM, Márquez H, Ochoa E, Morales M, Sosa M, Morán L, Rodríguez Y, Suárez M, Martín N, Seoane C (2000) Tetrahedron 56: 1533; (j) Levallet C, Lerpiniere J, Ko SY (1997) Tetrahedron 53: 5291; (k) Brindley JC, Caldwell JM, Meakins GD, Plackett SJ, Price SJ (1987) J Chem Soc, Perkin Trans 1 5: 1153; (l) Shome SC, Mazumder M, Haldar PK, Das DK (1977) J Indian Chem Soc 54: 10947; (m) Hassan AA, El-Shaieb KM, Shaker RM (2005) Heteroatom Chem 16: 112–119; (n) Natarajan A, Guo Y, Arthanari H, Wagner G, Halperin JA, Chorev M (2005) J Org Chem 70: 16 6362
LJ Farrugia (1997) J Appl Cryst 30 565 Occurrence Handle10.1107/S0021889897003117 Occurrence Handle1:CAS:528:DyaK2sXnt1KgsLg%3D
W Zhou L Zhu Y Zhang Z Yu L Lu X Yang (2004) Vib Spectrosc 36 73 Occurrence Handle10.1016/j.vibspec.2004.03.002 Occurrence Handle1:CAS:528:DC%2BD2cXovVCrsrc%3D
LV Sudha DN Sathyanarayana (1984) Spectrochim Acta 40A 751 Occurrence Handle1:CAS:528:DyaL2cXlvFSktro%3D
JN Eloff (1998) Planta Med 64 711 Occurrence Handle9933989 Occurrence Handle10.1055/s-2006-957563 Occurrence Handle1:CAS:528:DyaK1MXktlOjtA%3D%3D
C Kusucu B Rapino L McDermott S Hadley (2004) J Clin Microbiol 42 1224 Occurrence Handle10.1128/JCM.42.3.1224-1227.2004
Enraf-Nonius (1993) CAD-4/PC 1.2 Enraf-Nonius, Delft, The Netherlands
GM Sheldrick (1997) SHELXS97 and SHELXL9 Program Crystal Structure Refinement University of Göttingen Germany
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Cunha, S., Macedo, F., Costa, G. et al. Antimicrobial Activity and Structural Study of Disubstituted Thiourea Derivatives. Monatsh. Chem. 138, 511–516 (2007). https://doi.org/10.1007/s00706-007-0600-y
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DOI: https://doi.org/10.1007/s00706-007-0600-y