34560-01-5

Upstream product

• 141-84-4 2-thioxo-4-thiazolidinone 
• 1122-91-4 4-bromo-benzaldehyde 
• 5877-51-0 N-(4-bromobenzylidene)aniline 
• 108-86-1 bromobenzene 
• 98026-85-8 5-chloromethylene-2-thioxo-thiazolidin-4-one 

Downstream Products

• 1187463-25-7 (Z)-2'-[(5-amino-3-methyl-1-phenylpyrazol-4-yl)imino]-5'-(4-bromobenzylidene)thiazolidin-4-one 
• 5765-89-9 1-mercapto-2-(p-bromophenyl)cinnamic acid 
• 32723-31-2 5-(4-bromo-benzylidene)-thiazolidine-2,4-dithione 
• 28996-12-5 5-(4-bromo-benzylidene)-2-methylsulfanyl-thiazol-4-one 
• 28996-50-1 5-(4-bromo-benzylidene)-3-methyl-2-thioxo-thiazolidin-4-one 

Relevant academic research and scientific papers

Facile synthesis of 5-arylidene rhodanine derivatives using Na2SO3 as an eco-friendly catalyst. Access to 2-mercapto-3-aryl-acrylic acids and a benzoxaborole derivative

A simple, efficient and environment-friendly procedure for the synthesis of 5-arylidene rhodanines derivatives via a Knoevenagel type reaction was developed using rhodanine, a variety of differently substituted aldehydes and Na2SO3 a

Introducing broadened antibacterial activity to rhodanine derivatives targeting enoyl-acyl carrier protein reductase

Broadened antibacterial activity was introduced to rhodanine derivatives targeting Mycobacterial tuberculosis enoyl-acyl carrier protein reductase (Mtb InhA) by recruiting feature of xacins to bring DNA Gyrase B inhibitory capability. This is significant for preventing further bacterial injections in the tuberculosis treatment. The most potent compound Cy14 suggested comparable bioactivity (IC50=3.18μM for Mtb InhA; IC50=10nM for DNA Gyrase B) with positive controls. Structure–activity relationship discussion and molecular docking model revealed the significance of rhodanine moiety and derived methoxyl on meta-position, pointing out orientations for future modification.

[Et3NH][HSO4] catalyzed efficient synthesis of 5-arylidene-rhodanine conjugates and their antitubercular activity

Abstract: We have described a highly efficient, safer protocol for the synthesis of 5-arylidene-rhodanine conjugates catalyzed by Bronsted acidic ionic liquid [Et3NH][HSO4] in excellent yields. The protocol offers cost-effective, environmentally benign, solvent-free conditions and recycle–reuse of the catalyst. The synthesized 5-arylidene-rhodanine conjugates were characterized on the basis of 1H NMR, 13C NMR and HRMS spectral data. A series of 5-arylidene-rhodanine derivatives 3a–h, 4a–h were synthesized and evaluated for their in vitro antitubercular activity against dormant Mycobacterium tuberculosis H37Ra and M. bovis BCG strains. Moreover, compounds 3a, 3b, 3e, 3f, 3g, 3h and 4f exhibited good antitubercular activity and were also evaluated for anti-proliferative activity against MCF-7, A549 and HCT116 cell lines using modified MTT assay and found to be noncytotoxic. Compounds 3a–h and 4f were further screened for their antibacterial activity against four bacteria strains to assess their selectivity towards M. tuberculosis. Furthermore, in silico ADME prediction of all the tested compounds followed the criteria for orally active drug and, therefore, these compounds may have a good potential for eventual development as oral agents. Graphical Abstract: [Figure not available: see fulltext.]

5-Aryl-2-(naphtha-1-yl)sulfonamido-thiazol-4(5: H)-ones as clathrin inhibitors

The development of a (Z)-5-((6,8-dichloro-4-oxo-4H-chromen-3-yl)methylene)-2-thioxothiazolidin-4-one (2), rhodanine-based lead that led to the Pitstop 2 family of clathrin inhibitors is described herein. Head group substitution and bioisosteric replacemen

The chelating behaviour of 3-(4-X-phenyl)-2-sulfanylpropenoic acids with the PbII ion - Relevance of the lone electron pair in the supramolecular structures of the 2:1 complexes

The interaction of 3-(4-X-phenyl)-2-sulfanylpropenoic acids [H 2(X-pspa); X = -F, -Cl, -Br, -I, -OCH3, -OCF3, -OH] with lead(II) acetate in an alcoholic medium was explored in the search for new chelating agents for the Pb2+ ion. The direct reactions afforded [Pb(X-pspa)] complexes in yields of 67 (X = -Br) to 95 % (X = -OCH 3). When the PbII/H2(X-pspa) reaction was performed in the presence of diisopropylamine (Q), the derivatives [HQ] 2[Pb(X-pspa)2] (X = Cl, Br) were obtained. All of the complexes were characterized by spectrometric (FAB-MS and ESI-MS) and spectroscopic (IR, 1H and 13C NMR spectroscopy) methods and these showed the permanence of the O,S coordination of the ligands to the metal ion in dimethyl sulfoxide (DMSO) solution. H2(Cl-pspa), [HQ]2[Pb(Cl-pspa)2] and [HQ]2[Pb(Br-pspa) 2] were also fully characterized in the solid state by X-ray diffraction. The importance of the stereochemically active lone electron pair of the PbII ion in the supramolecular arrangement of [HQ] 2[Pb(X-pspa)2] (X = Cl, Br) is discussed. The characteristics of complexes formed by 3-(4-X-phenyl)-2-sulfanylpropenoic acids with lead(II) cations have been explored both in the solid state and in solution. The importance of the stereochemically active lone electron pair of the PbII ion in the supramolecular arrangement of [HQ] 2[Pb(X-pspa)2] (X = Cl, Br; Q = diisopropylamine) is discussed. Copyright

Urea/thiourea catalyzed, solvent-free synthesis of 5-arylidenethiazolidine- 2,4-diones and 5-arylidene-2-thioxothiazolidin-4-ones

An efficient and organo-catalyzed method has been developed for the synthesis of 5-arylidenethiazolidine-2,4-diones and 5-arylidene-2- thioxothiazolidin-4-ones via Knoevenagel condensation of arylaldehydes 1 and 2,4-thiazolidinedione 2a/2-thioxothiazolidin-4-one 2b under mild conditions. Urea-adduct 4 and azomethine 5 also afford arylidene-products 3 by reacting with 2a-b via addition-elimination reaction. This protocol has the features of use of inexpensive, ecofriendly readily available, effective catalyst system viz. urea/thiourea, avoidance of volatile solvents, excellent yield and simple work-up procedure.

The Rhodadyns, a new class of small molecule inhibitors of dynamin gtpase activity

Six focused rhodanine-based libraries, 60 compounds in total, were synthesized and evaluated as potential dynamin I GTPase inhibitors. Twenty-six were more potent than the lead compound with 13 returning IC50 values ≤10 μM, making the Rhodadyn

A solvent-free protocol for the green synthesis of arylalkylidene rhodanines in a task-specific ionic liquid

2-Hydroxyethylammonium formate acts as a task-specific ionic liquid (TSIL) for the Knoevenagel condensation of carbonyl compounds with rhodanine to afford arylalkylidene rhodanines under solvent-free conditions and in good-to-excellent yields. Additionally, compared with those in organic solvents, the yields obtained in the presence of our ionic liquid (IL) were significantly increased. The detailed mechanism of the catalytic effect of TSIL is also reported for the first time.

Selective small molecule inhibitors of the potential breast cancer marker, human arylamine N-acetyltransferase 1, and its murine homologue, mouse arylamine N-acetyltransferase 2

The identification, synthesis and evaluation of a series of rhodanine and thiazolidin-2,4-dione derivatives as selective inhibitors of human arylamine N-acetyltransferase 1 and mouse arylamine N-acetyltransferase 2 is described. The most potent inhibitors

Green synthesis of 5-benzylidene rhodanine derivatives catalyzed by 1-butyl-3-methyl imidazolium hydroxide in water

A basic functionalized ionic liquid, 1-butyl-3-methyl imidazolium hydroxide ([bmim][OH]), catalyzed the Knoevenagel condensation of rhodanine with aromatic aldehydes. It proceeded smoothly in water to afford the 5-benzylidene rhodamine derivatives in high yields at room temperature. This new method offers several advantages, such as excellent yields, short reaction times, and simple procedure. The catalyst can be reused at least 5 times without significant loss of activity.