3747-06-6

Basic information

• Product Name: N-[(3-ethyl-4-oxo-2-thioxo-5-thiazolidinylidene)methyl]-N-phenylacetamide
• Synonyms: N-[(3-ethyl-4-oxo-2-thioxo-5-thiazolidinylidene)methyl]-N-phenylacetamide;N-[(3-Ethyl-4-oxo-2-thioxothiazolidin-5-ylidene)methyl]-N-phenylacetamide;Acetamide, N-((3-ethyl-4-oxo-2-thioxo-5-thiazolidinylidene)methyl)-N-phenyl-;Einecs 223-143-2
• CAS NO: 3747-06-6
• Molecular Formula: C₁₄H₁₄N₂O₂S₂
• Molecular Weight: 306.40316
• EINECS: 223-143-2
• Mol File: 3747-06-6.mol

Chemical Properties

• Melting Point: 123-125 °C (polymorph)(Solv: methanol (67-56-1))
• Boiling Point: 420.1°Cat760mmHg
• Flash Point: 207.9°C
• Appearance: /
• Density: 1.38g/cm³
• Vapor Pressure: 2.89E-07mmHg at 25°C
• Refractive Index: 1.686
• PKA: -0.56±0.20(Predicted)
• CAS DataBase Reference: N-[(3-ethyl-4-oxo-2-thioxo-5-thiazolidinylidene)methyl]-N-phenylacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[(3-ethyl-4-oxo-2-thioxo-5-thiazolidinylidene)methyl]-N-phenylacetamide(3747-06-6)
• EPA Substance Registry System: N-[(3-ethyl-4-oxo-2-thioxo-5-thiazolidinylidene)methyl]-N-phenylacetamide(3747-06-6)

Safety Data

• Hazardous Substances Data: 3747-06-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H14N2O2S2/c1-3-15-13(18)12(20-14(15)19)9-16(10(2)17)11-7-5-4-6-8-11/h4-9H,3H2,1-2H3/b12-9+

Upstream product

• 864131-95-3 N,N'-diphenylformamidine 
• 7648-01-3 3-ethylrhodanin 
• 118050-10-5 5-anilinomethylidene-3-etylrhodanine 
• 108-24-7 acetic anhydride 
• 6780-49-0 Ethyl N-phenylformimidate 
• 39542-83-1 3-ethyl-5-((phenylamino)methylene)-2-thioxothiazolidin-4-one 

Downstream Products

• 3747-14-6 3-ethyl-5-[2-(4-phenyl-4H-benzo[f]quinolin-3-ylidene)-ethylidene]-2-thioxo-thiazolidin-4-one 
• 3747-16-8 3-ethyl-2-thioxo-5-[2-(4-p-tolyl-4H-benzo[f]quinolin-3-ylidene)-ethylidene]-thiazolidin-4-one 
• 3747-18-0 3-ethyl-5-{2-[4-(4-methoxy-phenyl)-4H-benzo[f]quinolin-3-ylidene]-ethylidene}-2-thioxo-thiazolidin-4-one 
• 3747-13-5 3-ethyl-5-[2-(1-phenyl-1H-quinolin-2-ylidene)-ethylidene]-2-thioxo-thiazolidin-4-one 
• 21425-55-8 3-ethyl-5-[2-(1-phenyl-1H-quinolin-4-ylidene)-ethylidene]-2-thioxo-thiazolidin-4-one 
• 3747-15-7 3-ethyl-5-[2-(6-methyl-1-p-tolyl-1H-quinolin-2-ylidene)-ethylidene]-2-thioxo-thiazolidin-4-one 
• 21443-01-6 3-ethyl-5-[2-(6-methyl-1-p-tolyl-1H-quinolin-4-ylidene)-ethylidene]-2-thioxo-thiazolidin-4-one 
• 21425-43-4 3-ethyl-5-{2-[6-methoxy-1-(4-methoxy-phenyl)-1H-quinolin-2-ylidene]-ethylidene}-2-thioxo-thiazolidin-4-one 
• 21425-52-5 3-ethyl-5-{2-[6-hydroxy-1-(4-hydroxy-phenyl)-1H-quinolin-4-ylidene]-ethylidene}-2-thioxo-thiazolidin-4-one 
• 4597-30-2 3-ethyl-2-[2-(3-ethyl-4-oxo-2-thioxo-thiazolidin-5-ylidene)-ethylidene]-1-phenyl-2,3-dihydro-1H-benzoimidazole-5-carbaldehyde 
• 4597-31-3 3-{3-ethyl-2-[2-(3-ethyl-4-oxo-2-thioxo-thiazolidin-5-ylidene)-ethylidene]-1-phenyl-2,3-dihydro-1H-benzoimidazol-5-yl}-acrylic acid 
• 36636-28-9 3-ethyl-5-{2-[5-(3-hydroxy-3-phenyl-triaz-1-enyl)-3-methyl-benzothiazol-2-ylidene]-ethylidene}-2-thioxo-thiazolidin-4-one 
• 56133-17-6 5-[2-(5-benzothiazol-2-yl-3-ethyl-1-phenyl-1,3-dihydro-benzoimidazol-2-ylidene)-ethylidene]-3-ethyl-2-thioxo-thiazolidin-4-one 
• 38801-01-3 3-ethyl-5-{2-[5-(3-hydroxy-3-phenyl-triaz-1-enyl)-3-methyl-1-phenyl-1,3-dihydro-benzoimidazol-2-ylidene]-ethylidene}-2-thioxo-thiazolidin-4-one 

Relevant articles and documents

Synthesis of three classes of rhodacyanine dyes and evaluation of their in vitro and in vivo antimalarial activity

Selected members of three classes of rhodacyanine dyes, [0, 0]-, [1, 0]-, and [0, 0, 0]-rhodacyanines, were synthesized and their in vitro antimalarial activities against Plasmodium falciparum K1 (chloroquine-resistant strain) as well as their in vivo activities against P. berghei in mice were determined. The novel [0, 0, 0]-rhodacynines, 3e and 3h, possessing a benzothiazole moiety, were shown to have highly promising antimalarial activities in vivo. Moreover, the [0, 0, 0]-rhodacyanines were found to be orally bioavailable.

Solvent-dependent ratiometric fluorescent merocyanine dyes: Spectral properties, interaction with BSA as well as biological applications

A series of merocyanine dyes with excellent spectral properties were synthesized through changing the heterocyclic base structure for protein labeling and imaging in biological science, such as living cells and living mice. Dyes 7c-7h showed solvent-dependent changes on emission wavelength and fluorescence intensity in water and hydrophobic solvents, which were further analyzed by theoretical calculations and absorption spectra. The interaction of dye 7d with bovine serum albumin (BSA) showed an obvious ratiometric fluorescence response to solvent/protein environment, with the potential to report protein conformational changes. Investigation of the cytotoxicity and bioimaging capability displayed that dyes 7b-7h showed low cytotoxicity, and could stain living cell cytoplasm and be used for imaging in living mice with bright fluorescence at the application dose, which was suggested as fluorescent reagents for imaging in biological science.

Structure-activity of novel rhodacyanine dyes as antitumor agents

We have previously reported that rhodacyanine dyes, such as 1 and 2, exhibited a potent inhibitory effect on the growth of several tumor cells and that 4-oxothiazolidine (rhodanine) was an essential moiety for antitumor activity. On the basis of our foregoing work, two types of rhodacyanine dyes, which categorized into class I and II depending on the methine length, were synthesized and evaluated as a novel antitumor agent. Attention was particularly focused on the structure-activity study of two heteroaromatic rings. In class I, where the A rings were conjugated to rhodanine via two methine groups, compounds 1, 20, 23, and 24 were found to be efficacious in tumor-bearing nude mice model study, but they did not have the chemical properties (stability, solubility) suitable for clinical use. In contrast, in class II, where the A rings were directly conjugated to rhodanine, compounds 13 and 25, which possessed a benzothiazole moiety for the A ring, exhibited the favorable biological and chemical properties. Therefore, we decided to have a benzothiazole moiety as the A ring and introduce various heterocyclic groups for the B ring. As a result, the pyridinium ring was selected as the optimal moiety for the B ring (compound 13). Further, the variation of counteranion had a profound effect on solubility in water without influence on antitumor activity. Chloride anion was selected as the favorable anion with respect to synthetic method as well as solubility in water. Our study finally led us to the identification of compound 3 (MKT 077, 1-ethyl-2-[[3- ethyl-5-(methylbenzothiazolin-2-ylidene)-4-oxothiazolidin-2- ylidene]pyridinium chloride) as the candidate for clinical trials and is currently subjected to further investigation as a potent antitumor agent in phase I clinical trial for the treatment of solid tumors.

Synthesis and evaluation of novel rhodacyanine dyes that exhibit antitumor activity

Rhodacyanine dyes and several analogous delocalized lipophilic cations (DLCs) were synthesized and evaluated as novel antitumor agents Rhodacyanine dye consists of two heteroaromatic rings such as thiazoles at both termini of the conjugate systems and 4-oxothiazolidine (rhodanine) in the middle of it. Compounds with such a unique double-conjugate structure were found to inhibit the growth of several tumor cell lines, such as colon carcinoma CX-1, and to exhibit relatively low toxicity against normal kidney cell line CV-1 (e.g., IC50(CX-1) = 50 nM, IC50(CV-1) = 17.3 μM; selectivity index = 346 for compound 5). These compounds were also found to be efficacious in the tumor- bearing nude mice model (e.g., against human melanoma LOX; T/C (%) = 168 for compound 5). Structural modifications on rhodacyanine, including deletion of a heteroaromatic ring involved in the merocyanine conjugate system and replacement of rhodanine with a structurally related moiety such as 4- oxoimidazolidine or 4-oxo-1,3-dithiolane, resulted in a loss of the selectivity and/or the activity. Our current structure-activity studies imply that the double-conjugate system with a rhodanine moiety is essential for the selective activity of rhodacyanine dyes, and we find this class of compounds as unique antitumor agent candidates.

A 2-methylthio-3,5-diaryl-1,3,4-thiadiazolium cation; its reactions, and further exploration of the chemistry of 2-alkyl-3,5-diaryl-1,3,4-thiadiazolium cations

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