Synthesis and Antimicrobial Activity of Thiohydantoins
Letters in Drug Design & Discovery, 2020, Vol. 17, No. 1 101
[14]
Karali, N.; Gürsoy, A.; Terzioglu, N.; Ozkirimli, S.; Ozer, H.;
Ekinci, A.C. Synthesis and preliminary CNS depressant activity
evaluation of new 3-[(3-substituted-5-methyl-4-thiazolidinon-2-
ACKNOWLEDGEMENTS
The authors thank Spectroscopy Laboratory (SPEC/
UEL/FINEP) for the NMR spectra.
ylidene)hydrazono]-1H-2-
indolinones
and
3-[(2-thioxo-3-
substituted-4,5-imidazolidinedion-1-yl) imino]-1H-2-indolinones.
Arch. Pharm. (Weinheim), 1998, 331(7-8), 254-258.
4184(199807)331:7/8<254::AID-ARDP254>3.0.CO;2-R] [PMID:
9747182]
S.; Salhi, L.; Belkebir, A.; Ait-Yahia, O.; Boudjlida, A.; Bouguer-
ra-Aouichat, S.; Nedjar-Kolli, B. Antioxidant and anti tumoral ac-
tivities of hydrazylpyrrolidine 2,5 dione substituted and 2-thioxo
imidazolidine 4-one. Int. J. Pharm. Chem. Biol. Sci., 2014, 4(3),
447-452.
Buchynskyy, A.; Gillespie, J.R.; Herbst, Z.M.; Ranade, R.M.;
Buckner, F.S.; Gelb, M.H. 1-Benzyl-3-aryl-2-thiohydantoin deriva-
tives as new anti-Trypanosoma brucei agents: SAR and in vivo Ef-
ficacy. ACS Med. Chem. Lett., 2017, 8(8), 886-891.
SUPPLEMENTARY MATERIAL
Supplementary material is available on the publisher’s
web site along with the published article.
[15]
[16]
REFERENCES
[1]
[2]
[3]
Wenzel, R.P.; Edmond, M.B. The impact of hospital-acquired
bloodstream infections. Emerg. Infect. Dis., 2001, 7(2), 174-177.
[http://dx.doi.org/10.3201/eid0702.010203] [PMID: 11294700]
Health
care-associated
infections
Fact
Sheet.,
pdf [Accessed Oct 18, 2017];
[http://dx.doi.org/10.1021/acsmedchemlett.7b00230]
28835807]
[PMID:
Klevens, R.M.; Edwards, J.R.; Richards, C.L., Jr; Horan, T.C.;
Gaynes, R.P.; Pollock, D.A.; Cardo, D.M. Estimating health care-
associated infections and deaths in U.S. hospitals, 2002. Public
Health Rep., 2007, 122(2), 160-166.
[17]
[18]
Tompkins, J.E. 5,5-Diaryl-2-thiohydantoins and 5,5-diaryl-N3-
substituted-2-thiohydantoins as potential hypolipidemic agents. J.
Med. Chem., 1986, 29(5), 855-859.
[http://dx.doi.org/10.1021/jm00155a042] [PMID: 2939244]
al-Obaid, A.M.; el-Subbagh, H.I.; Khodair, A.I.; Elmazar, M.M.A.
5-substituted-2-thiohydantoin analogs as a novel class of antitumor
agents. Anticancer Drugs, 1996, 7(8), 873-880.
[http://dx.doi.org/10.1097/00001813-199611000-00009] [PMID:
8991192]
Marx, J.V.; Richert, D.A.; Westerfeld, W.W. Peripheral inhibition
of thyroxine by thiohydantoins derived from amino acids. J. Med.
Chem., 1970, 13(6), 1179-1181.
[http://dx.doi.org/10.1177/003335490712200205]
17357358]
[PMID:
[4]
[5]
[6]
Ventola, C.L. The antibiotic resistance crisis: Part 1: Causes and
threats. P&T, 2015, 40(4), 277-283.
[PMID: 25859123]
Allen, H.K.; Trachsel, J.; Looft, T.; Casey, T.A. Finding alterna-
tives to antibiotics. Ann. N.Y. Acad. Sci., 2014, 1323, 91-100.
[http://dx.doi.org/10.1111/nyas.12468] [PMID: 24953233]
Poyraz, S.; Belveren, S.; Ülger, M.; Sahin, E.; Döndas, H.A. Syn-
thesis, characterization, crystal structure and anti-tuberculosis ac-
[19]
[20]
[21]
[http://dx.doi.org/10.1021/jm00300a036] [PMID: 5479861]
Marton, J.; Enisz, J.; Hosztafi, S.; Timar, T. Preparation and fungi-
cidal activity of 5-substituted hydantoins and their 2-thio analogs.
J. Agric. Food Chem., 1993, 41, 148-152.
tivity
of
some
novel
polysubstituted
aminocarbothi-
ol/thiohydantoin-pyrrolidine derivatives. Monatsh. Chem., 2017,
148(12), 2173-2182.
[http://dx.doi.org/10.1021/jf00025a031]
[http://dx.doi.org/10.1007/s00706-017-2039-0]
LeTiran, A.; Stables, J.P.; Kohn, H. Functionalized amino acid
anticonvulsants: Synthesis and pharmacological evaluation of con-
formationally restricted analogues. Bioorg. Med. Chem., 2001,
9(10), 2693-2708.
[7]
[8]
Abubshait, S.A. Synthesis, antimicrobial and anticancer activities
of some 2-thiohydantoin derivatives. Indian J. Chem., 2017, 56B,
641-648.
Souza, S.P.; Masteloto, H.G.; Silva, D.S.; Azambuja, J.H.; Bra-
ganhol, E.; Ribeiro, J.S.; Lund, R.G.; Cunico, W. Antimicrobial
and citoxicity activities of 2-(aryl)-3-(benzo[d][1,3]dioxol-5-
yl)thiazolidin-4-ones. Lett. Drug Des. Discov., 2017, 14, 1042-
1047.
[http://dx.doi.org/10.1016/S0968-0896(01)00204-8]
11557357]
[PMID:
[22]
[23]
Cheymol, J.; Chabrier, P.; Gay, Y. Antithyroid action and molecu-
lar structure. I. A study of thiohydantoins and their methyl esters.
Arch. Int. Pharmacodyn. Ther., 1951, 87(3), 321-333.
[PMID: 14895194]
[http://dx.doi.org/10.2174/1570180814666170106143418]
Thanusu, J.; Kanagarajan, V.; Gopalakrishnan, M. Synthesis, spec-
tral analysis and in vitro microbiological evaluation of 3-(3-alkyl-
2,6-diarylpiperin-4-ylidene)-2-thioxoimidazolidin-4-ones as a new
class of antibacterial and antifungal agents. Bioorg. Med. Chem.
Lett., 2010, 20(2), 713-717.
[9]
Cunha, S.; Macedo, F.C., Jr; Costa, G.A.N.; Rodrigues, M.T., Jr;
Verde, R.B.V.; Neta, L.C.S.; Vencato, I.; Lariucci, C.; Sá, F.P. An-
timicrobial activity and structural study of disubstituted thiourea
derivatives. Monatsh. Chem., 2007, 138, 511-516.
[http://dx.doi.org/10.1007/s00706-007-0600-y]
[http://dx.doi.org/10.1016/j.bmcl.2009.11.074] [PMID: 20004098]
Wu, F.; Jiang, H.; Zheng, B.; Kogiso, M.; Yao, Y.; Zhou, C.; Li,
X.N.; Song, Y. Inhibition of cancer-associated mutant isocitrate
dehydrogenases by 2-thiohydantoin compounds. J. Med. Chem.,
2015, 58(17), 6899-6908.
[24]
[25]
El Hady, H.A. Synthesis and antimicrobial activity of some new
thiohydantoin and thiazole derivatives. Pharma Chem., 2012, 4(6),
2202-2207.
[10]
[11]
Kachhadia, V.V.; Patel, M.R.; Joshi, H.S. Heterocyclic systems
containing S/N regioselective nucleophilic competition: Facile syn-
thesis, antitubercular and antimicrobial activivty of thiohydantoins
and iminothiazolidinones containing the benzo [b]thiophene moie-
ty. J. Serb. Chem. Soc., 2005, 70(2), 153-161.
[http://dx.doi.org/10.1021/acs.jmedchem.5b00684]
26280302]
[PMID:
Raj, R.; Mehra, V.; Gut, J.; Rosenthal, P.J.; Wicht, K.J.; Egan, T.J.;
Hopper, M.; Wrischnik, L.A.; Land, K.M.; Kumar, V. Discovery of
highly selective 7-chloroquinoline-thiohydantoins with potent an-
timalarial activity. Eur. J. Med. Chem., 2014, 84, 425-432.
[http://dx.doi.org/10.1016/j.ejmech.2014.07.048]
25038484]
[http://dx.doi.org/10.2298/JSC0502153K]
[26]
[27]
[28]
Mohamed, N.A.; Abd El-Ghany, N.A. Preparation and antimicro-
bial activity of some carboxymethyl chitosan acyl thiourea deriva-
tives. Int. J. Biol. Macromol., 2012, 50(5), 1280-1285.
[PMID:
[http://dx.doi.org/10.1016/j.ijbiomac.2012.03.011]
22469914]
[PMID:
[12]
[13]
Suzen, S.; Buyukbingol, E. Evaluation of anti-HIV activity of 5-(2-
phenyl-3′-indolal)-2-thiohydantoin. Farmaco, 1998, 53(7), 525-
527.
Diţu, L.M.; Mihăescu, G.; Chifiriuc, C.; Bleotu, C.; Morusciag, L.;
Niţulescu, G.M.; Missir, A. In vitro assessment of the antimicrobial
activity of new N-acyl-thiourea derivatives. Roum. Arch. Microbi-
ol. Immunol., 2010, 69(1), 41-47.
[http://dx.doi.org/10.1016/S0014-827X(98)00053-6]
9836465]
[PMID:
Porwal, S.; Chauhan, S.S.; Chauhan, P.M.S.; Shakya, N.; Verma,
A.; Gupta, S. Discovery of novel antileishmanial agents in an at-
tempt to synthesize pentamidine-aplysinopsin hybrid molecule. J.
Med. Chem., 2009, 52(19), 5793-5802.
[PMID: 21053783]
Cromwell, L.D.; Stark, G.R. Determination of the carboxyl termini
of proteins with ammonium thiocyanate and acetic anhydride, with
direct identification of the thiohydantoins. Biochemistry, 1969,
8(12), 4735-4740.
[http://dx.doi.org/10.1021/jm900564x] [PMID: 19743860]
[http://dx.doi.org/10.1021/bi00840a012] [PMID: 4904040]