Rhodanine-3-acetic acid

Orchard et al. [27] have s)mthesized rhodanine-3-acetic acid derivatives XVI, XVn, and XVIII inhibit Candida albicans PMTl with inhibition concentration 50% (IC50) values 0.17,0.2, and 0.35 pM, respectively. These compounds could serve as useful tools for studjdng the effects of protein O-mannosylation and its relevance in the search for novel antifungal agents. 

Miao J, Zheng C, Sun L, Song M, Xu L, Piao H. Synthesis and potential antibacterial activity of new rhodanine-3-acetic acid derivatives. Med. Chem. Res. 2013, 22, 4125-4132. 

Orchard MG, Neuss JC, Galley CM, Carr A, Porter DW, Smith P, Scopes DI, Haydon D, Vousden K, Stubberfield CR, Young K, Page M. Rhodanine-3-acetic acid derivatives as inhibitors of fungal protein mannosyl transferase 1 (PMTl). Bioorg. Med. Chem. Lett. 2004,14, 3975-3978. 

S.G. Alegaon, K.R. Alagawadi, P.V. Sonkusare, SA4. Chaudhary, D.H. Dadwe, A.S. Shah, Novel imidazo[2,l-b][l,3,4]thiadiazole carrying rhodanine-3-acetic acid as potential antitubercular agents, Bioorg. Med. Chem. Lett. 22 (2012) 1917-1921. 

Rhodanine (2-mercaptothiazolidin-4-one) 5.18. Crystd from glacial acetic acid or water. 

C5H5N03S2 rhodanine-N-acetic acid 5718-83-2 25.00 1.4921 2 4581 C5H604 trans-1 -propene-1,2-dicarboxylic acid 498-24-8 20.00 1.4660 1... 

Crystallise rhodanine from glacial acetic acid or water. It is used to estimate Ag and gallic acid [Thies Fischer Microchimica Acta 809 1973]. [Beilstein 27 H 242, 27 I 309, 27 II 288, 27 IIEIV 3188.]... 

Treatment of rhodanines with an excess of zinc dust in acetic acid leads to the reduction of the thioxo group yielding 4-thiazolidinones <94TL697i>. 

A mixture of furfural, 2,4-thiazolidione, fused Na-acetate, and glacial acetic acid refluxed 45 min. — 5-(2-furfurylidene)-2,4-thiazolidione (Y 95%) kept with 15%-NaOH at 40° for 8 hrs. -> 2-furylthiopyruvic acid (Y 91.8%).—This method can be applied to larger batches than the Grftnacher synthesis via rhodanine (cf. Synth. Meth. 3, 662), since hydrolysis occurs at rather low temp. (F. e. s. D. Libermann, J. Him-bert, and L. Hengl, Bl. 1948, 1120.)... 

Aminothiazole reacts with both ferrocenecarboxaldehyde and ferrocenecarboxylic acid chlorideto give the expected imine and amide, respectively. Ferrocenecarboxylic acid chloride also reacts with phenothiazine to give both N- and C-acetylation. Ferrocene-carboxaldehyde and rhodanine gave 134, while reaction of the thiosemicarbazone of ferrocenecarboxaldehyde with chloroacetic acid in acetic acid gave 135. ... 

ONO-2235 (9) is the predominant E,E geometric isomer resulting from condensation of a-methylcinnamaldehyde with rhodanine-N-acetic acid and not the E,Z isomer as incorrectly shown in reference 83. This agent is a potent inhibitor of REAR and given orally for two weeks markedly reduced sorbitol levels in rat sciatic nerve and improved MNCV and has completed three months clinical evaluation in neuropathy patients. ... 

Reagents and Equipment. In a 3.0-mL conical vial containing a boiling stone and equipped with an air condenser, weigh out and place 30 mg (0.23 mmol) of rhodanine and 52 mg (0.63 mmol) of anhydrous sodium acetate. Now, in the hood, add 1.0 mL of glacial acetic acid dispensed from a graduated pipet. To this mixture, measure and add 58 mg (0.41 mmol) of o-chlorobenzaldehyde ( ). 

To 90 ml of a suitable concentration of mercury in neutral or acetic acid solution add 5 0 ml of N nitric acid from a pipette, mix thoroughly, add 3 0 ml of /)-dimethylaminobenzylidine-rhodanine reagent (0 04 g shaken with 200 ml of ethanol, left overnight and filtered), adjust the volume to 100 ml and mix. Compare with standards prepared by adding suitable known amounts of standard mercuric nitrate solution (0-5 g mercury in 5 ml of concentrated nitric acid, dilute, boil to remove nitrous fumes and dilute to 250 ml make further dilutions so that 1 ml 0 0001 g Hg) to similar amounts of nitric acid and reagents as used in the test solution. Develop the colour in both test solution and standards simultaneously, allow to stand for five minutes and compare. 

The condensation with rhodanine in boiling acetic acid gives (133) in high yield. The corresponding thiazolinium salts, having their 2-position activated towards nucleophiles, react identically under much milder conditions. In acetic anhydride, the reaction proceeds differently, producing, by way of the isolable intermediates (134) and (135), the acetylated condensed product (136). ... 

Heating the first-obtained product in a strong acid leads to the hydrolysis of the ester. The resulting (3-ketoacid loses carbon dioxide under reaction conditions the acetal hydrolyses also reveal the free aldehyde (106-6). Aldol condensation of this last intermediate in the presence of a base with readily available rhodanine (106-7) links the two fragments. The double bond in the first-formed product is then reduced catalytically to afford darglitazone (106-8) [117]. 

This reaction has been applied to a great number of carbonyl compounds, e.g., cyclopentanone,27 1,3-cyclohexanedione,36 5,5-dimethyl-l,3-cyclohexanedione,S5 1-acenaphthenone,24,25 1,3-indane-dione,35 1,3-phenalanedione,85 86 sodium salts of 3-aryl-3-oxo-propanals,39 2,3-dihydrobenzo[6]thiophen-3-one,40 sodium benzoyl-acetate,41 benzoylacetonitrile,29 30,88 ethyl cyanoacetate,30 35 cyano-acetanilide,30 barbituric acid,35 rhodanine,35 jV-phenylrhodanine,37 and iV-methylenebenzothiazoline.37... 

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