4-Thiazolidinone – A biologically active scaffold

Verma, Amit; Saraf, Shailendra K.

doi:10.1016/j.ejmech.2007.07.017

Cited by 409 publications

(211 citation statements)

References 59 publications

Supporting

Mentioning

205

Contrasting

Unclassified

Order By: Relevance

“…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%

“…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]. 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.…”

Section: Discussionmentioning

confidence: 99%

See 1 more Smart Citation

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

View full text Add to dashboard Cite

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.

show abstract

Section: Discussionmentioning

confidence: 99%

“…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]. 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.…”

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

View full text Add to dashboard Cite

show abstract

“…1,3-Thiazolidin-4-ones are a class of compounds that have shown potential as antibacterials (Aridoss et al, 2009;Gopalakrishnan et al, 2009;Jain et al, 2012;Poyraz et al, 2013;Sayyed et al, 2006;Verma and Saraf, 2008;Vicini et al, 2006;Vicini et al, 2008). Thiazolidin-4-ones have been found as inhibitors of the bacterial enzyme MurB; a key enzyme responsible for the synthesis of peptidoglycan (Andres et al, 2000).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antibacterial activity of novel 2-(arylimino)thiazolidin-4-one and 2-(benzylidenehydrazono)-3-arylthiazolidin-4-one derivatives

El‐Hossary¹,

Nissan²,

Edkins³

et al. 2016

J App Pharm Sci

View full text Add to dashboard Cite

The ongoing spread of multidrug-resistant bacteria demands an intensive search for new antibacterial agents. In the present study, a series of new 1,3-thiazolidin-4-ones has been synthesized and investigated for its in vitro antibacterial activity. The most potent antibacterial compound 4c was found to be active, at low micromolar range, against Staphylococcus aureus, Staphylococcus epidermidis, Enterococcus faecalis and the pneumonic plague causative agent Yersinia pestis with minimum inhibitory concentrations of 5 µM, 2.5 µM, 2.5 µM and 5 µM, respectively. Compound 4c showed the ability to kill E. faecalis JH212 strain with a minimum bactericidal concentration of 5 µM. Furthermore, compounds 9b and 10a inhibited the biofilm formation in S. epidermidis, where they showed 70% to 80% inhibition at a concentration of 40 µM.

show abstract

“…The antibacterial activity of thiazolidinones is due to its inhibitory activity of enzyme MurB which is a precursor during the biosynthesis of peptidoglycan [3]. It was reported that the thiazolidinone scaffold mimicked the diphosphate and different groups present around the ring generates the specificity [4,5]. Certain thiazolidinones were recently reported to be the inhibitors of mycobacterial rhamnose synthetic enzymes [6].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of Novel Heterocycles Containing Thiazolidinone and 1,3,4-Oxadiazole Moieties

Kumar¹

2016

Ann Clin Anal Med

View full text Add to dashboard Cite

4-Thiazolidinone – A biologically active scaffold

Cited by 409 publications

References 59 publications

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

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

Synthesis and antibacterial activity of novel 2-(arylimino)thiazolidin-4-one and 2-(benzylidenehydrazono)-3-arylthiazolidin-4-one derivatives

Synthesis and Antimicrobial Activity of Novel Heterocycles Containing Thiazolidinone and 1,3,4-Oxadiazole Moieties

Contact Info

Product

Resources

About