Synthesis and antimicrobial activity of novel 2-thiazolylimino-5-arylidene-4-thiazolidinones

Vicini, Paola; Geronikaki, Athina; Anastasia, Kitka; Incerti, Matteo; Zani, Franca

doi:10.1016/j.bmc.2006.01.043

Cited by 288 publications

(166 citation statements)

References 24 publications

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“…The Z configuration was postulated due to the deshielded methine proton signals by adjacent carbonyl group for both 4a-4d ( 7.83-8.18) and 7a-7d ( 7.90-8.02) in the 1 H NMR spectra. These higher chemical shifts were in coordination with the Z configuration in comparison with the E configuration which expected to have lower chemical shifts [39,40]. All the newly synthesized compounds were characterized by physical analytical and spectral data and found to be in agreement with predicted values.…”

Section: Chemistrysupporting

confidence: 61%

Synthesis and Evaluation of New 2-Iminothiazolidin-4-one and Thiazolidin-2,4-dione Derivatives as Antimicrobial and Anti-inflammatory Agents

Bayoumi¹,

Abdel-Rhman²,

Shaker³

2014

CHEM

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Abstract:A new series of 2-iminothiazolidin-4-ones and thiazolidin-2,4-diones were designed and synthesized. The target compounds were evaluated for antimicrobial and anti-inflammatory activities, aiming to find a candidate carrying dual activities. The antibacterial activity was determined by cup-diffusion technique and NCCLS broth dilution method. The MICs were determined using 96-well microtitre plates, while the anti-inflammatory activity was determined using carrageenan-induced rat paw edema model. The results revealed that target compounds showed no antifungal activity towards tested Fungi, whereas the antibacterial activity was mainly on Gram-positive bacteria. The anti-inflammatory activity was observed in compounds belonging to the thiazolidin-2,4-dione series. The structures of the newly synthesized compounds were confirmed by physical and spectral data.

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Section: Chemistrysupporting

confidence: 61%

Synthesis and Evaluation of New 2-Iminothiazolidin-4-one and Thiazolidin-2,4-dione Derivatives as Antimicrobial and Anti-inflammatory Agents

Bayoumi¹,

Abdel-Rhman²,

Shaker³

2014

CHEM

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“…Recently, different protocols have been developed allowing the synthesis of imino thiazolidin-4-one skeletons. [19][20][21] In this connection, herein we report the synthesis of some new 2-iminothiazolidin-4-ones and their biological screening. Ten 2-aroylimino-3-aryl-thiazolidin-4-ones (2a-j) were synthesized and tested for their in vitro antimicrobial properties against Gram positive and Gram negative bacteria.…”

Section: Mycobacterium Tuberculosismentioning

confidence: 96%

Synthesis and antibacterial activity of some novel 2-Aroylimino-3-aryl-thiazolidin-4-ones

Saeed¹,

Abbas²,

Flörke³

2007

J. Braz. Chem. Soc.

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Este trabalho relata uma síntese eficiente e regio-seletiva de algumas 2-aroylimino-3-arylthiazolidin-4-ones (2a-j) envolvendo a ciclização de 1-aroyl-3-aryl tio-uréias em meio básico com cloreto de cloroacetila em dioxana. As estruturas foram confirmadas por dados espectroscópicos, análises elementares e, em um caso (2j), por dados de difração de raios X tipo cristal único. Os compostos foram testados in vitro quanto à sua atividade antimicrobiana em relação a bactérias Gram positivas e Gram negativas. Os resultados revelaram uma atividade promissora desses compostos em relação aos microorganismos testados, comparando-se e, em alguns casos, até superando a atividade das drogas existentes.An efficient, regioselective synthesis of some 2-aroylimino-3-aryl-thiazolidin-4-ones (2a-j) involving base-catalyzed cyclization of 1-aroyl-3-aryl thioureas with chloroacetyl chloride in dioxane is reported. The structures were confirmed by spectroscopic data, elemental analyses and in one case (2j) by single crystal X-ray diffraction data. Compounds (2a-j) were assayed in vitro for their antimicrobial activity against Gram positive and Gram negative bacteria and were found to exhibit promising activity towards the tested microorganisms, comparable to and in some cases better than those of the standard drugs.

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“…Thiazolidinone moiety is an important structure element in medicinal chemistry [2][3][4][5][6] and substituted thiazolidinones show a broad spectrum of biological activities [7][8][9][10][11] [16].Therefore, facile preparation of various 5-arylidene thiazolidinones is highly desirable. In continuation of our ongoing interests in the development of benign methods targeted at the synthesis of biologically important heterocycles [17][18][19], we used base supported ionic liquid-like phase (SILLP) [20] as an efficientand recyclablesolid phasecatalystinthe synthesis of thetitle compound.…”

Section: Discussionmentioning

confidence: 99%

“…In particular, 5-arylidene-4-thiazolidinones have been synthesized and employed as new agents with SHP-2 inhibitory action [12],aspotential antifungal and antibacterial drugs [13],asPTP1Band LMW-PTP inhibitors [14],a nti-inflammatory agent [15] and antimicrobial drugs [16].Therefore, facile preparation of various 5-arylidene thiazolidinones is highly desirable. In continuation of our ongoing interests in the development of benign methods targeted at the synthesis of biologically important heterocycles [17][18][19], we used base supported ionic liquid-like phase (SILLP) [20] as an efficientand recyclablesolid phasecatalystinthe synthesis of thetitle compound.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of (2Z,5Z)-3-allyl-5-(4-(methylthio)benzylidene)- 2-(p-tolylimino)thiazolidin-4-one, C21H20N2OS2

Mamaghani¹,

Joshari²,

Tabatabaeian³

et al. 2011

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialTo as olution of 3-allyl-2-(p-tolylimino)thiazolidin-4-one (3 mmol) and base supported ionic liquid-like phase (SILLP) (0.5 g) in ethanol (20 mL), 4-methylthiobenzaldehyde (3 mmol) was added and the mixture was heated at reflux for 3h.S ILLP was separated by filtration. Then the solution was concentrated in vacuum and kept at -15 ºC over 2h.The residue was filtered off and recrystallized from methanol to give 3-allyl-5-(4-(methylthio)benzylidene)-2-(p-tolylimino)thiazolidin-4-one as ayellow solid in 87 %yield (m.p. =138-140°C). Elemental analysisfound: C, 66.13 %; H, 5.35 %; N, 7.47 %; calculated for C 21 H 20 N 2 OS 2 :C,66.28 %; H, 5.30 %; N, 7.36 %. Melting points were measured on aElectrothermal 9100 instrument and are uncorrected. Elemental analyses were made by aC arlo-Erba EA1110CNNO-S analyzer. Experimental detailsAll hydrogen atomswere refined in isotropic approximation in a riding model with U iso (H) =1 .2 U eq (C). The structure was checked with PLATON [1] and no solvent accesible void was found. The residual densities are 0.32 eÅ -3 (highest peak at 1.24 Åfrom C13) and -0.21 eÅ -3 (deepest hole at 0.61 Åfrom H12). DiscussionThiazolidinone moiety is an important structure element in medicinal chemistry [2][3][4][5][6] and substituted thiazolidinones show a broad spectrum of biological activities [7][8][9][10][11] [16].Therefore, facile preparation of various 5-arylidene thiazolidinones is highly desirable. In continuation of our ongoing interests in the development of benign methods targeted at the synthesis of biologically important heterocycles [17][18][19], we used base supported ionic liquid-like phase (SILLP) [20] as an efficientand recyclablesolid phasecatalystinthe synthesis of thetitle compound. The X-ray diffractometric analysis of the title product was carried out on the single crystal prepared in peteroleum ether/EtOAc(4:1). The packing in the title crystal structure can be described as asuccessionofparallel layers.The conjugationbetween C=Oand the amiden itrogeni se vident from thev alue of theb ondl ength d(Nl-C10) =1.362(5)Å.The thiazole ring is planar as indicated by torsion angles ÐC9-C10-N1-C14 =-3.4(5)°, ÐN1-C10-C9-S2 =0.4(4)°, ÐC10-C9-S2-C14 =1.8(3)°and ÐN1-C14-S2-C9 =-36(3)°. In addition, the torsion angles ÐS2-C14-N2-C15 =0 .8(6)°, ÐO1-C10-N1-C11 =1 .2(6)°, ÐN2-C14-N1-C11 =1.8(6)°, ÐC5-C8-C9-S2 =-1.0(7)°and ÐN1-C10-C9-S2 =0 .4(4)°revealed that the thiazole ring is coplanar with O1, N2,C 5, C8,C 11 and C15.T he distances.362(5) Åagree with the literature reports [21][22][23][24][25]. The bond length d(C14-N2) =1.259(5) Åand the angles ÐN2-C14-S2 =128.2(3)°and ÐN2-C14-N1 =121.8(4)°con-firm the imine nature of the N2-C14 bond. The distance d(C8-C9)=1.331(5) Åand the angles ÐC8-C9-S2 =129.7(3)°a nd ÐC8-C9-C10 =120.5(3)°are consistant with double bond features of C8-C9.This analysis also unambiguously confirmed the Z configuration at the chiral axis and this is quite evident from the spatial orientation of arylg roups attached to C14-N2 and C8-C9 double bonds.

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Synthesis and antimicrobial activity of novel 2-thiazolylimino-5-arylidene-4-thiazolidinones

Cited by 288 publications

References 24 publications

Synthesis and Evaluation of New 2-Iminothiazolidin-4-one and Thiazolidin-2,4-dione Derivatives as Antimicrobial and Anti-inflammatory Agents

Synthesis and Evaluation of New 2-Iminothiazolidin-4-one and Thiazolidin-2,4-dione Derivatives as Antimicrobial and Anti-inflammatory Agents

Synthesis and antibacterial activity of some novel 2-Aroylimino-3-aryl-thiazolidin-4-ones

Crystal structure of (2Z,5Z)-3-allyl-5-(4-(methylthio)benzylidene)- 2-(p-tolylimino)thiazolidin-4-one, C21H20N2OS2

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