Tag: M.W=100-150

Girard, M. L. published the artcileStructural and reactional possibilities of thiazolidine derivatives. I. Addition, substitution, and hydrolysis, Related Products of thiazole, the publication is Bulletin de la Societe Chimique de France (1968), 3461-8, database is CAplus.

The reactivities of 2-imino-4-thiazolidinone (pseudothiohydantoin) (Ia), 2-4-thiazolidinedione (Ib), and 2-thio-2,4-thiazolidinedione (rhodanine) (Ic) were studied and some of their derivatives prepared by original or improved techniques and studied by thin layer chromatog., uv, ir, and polarography for structural determinations The hydrolytic ring cleavage was also investigated. E.g., addition reactions in the 2-position were attempted. A saturated solution of Ic in absolute EtOH was treated with saturated KOH in absolute EtOH to the exact equivalence point observed with a potentiometer to precipitate 90% K salt (II) of Ic. The K salt of the 2-thiohydantoin was obtained similarly (80%) in 8:2 EtOH-HCONMe2. II stirred in dilute EtOH during 2 hrs. with Me2SO4 gave yellow 2-(methylthio)-2-thiazolin-4-one, m. 170°. Stirring II in 90% EtOH with an equimol. amount of benzyl chloride at room temperature for 24 hrs. gave 2-(benzylthio)-2-thiazolin-4-one, yellowish brown, m. 65°. 2-(Acetylthio)-2-thiazolin-4-one (III), m. 250° (decomposition) was obtained by reaction of II in aqueous solution with an equimol. amount of ClCH2CO2H. Stirring ClCH2CO2K in dilute EtOH with an equimol. amount of II 1 hr. also gave III. Ic was converted into Ib by refluxing with 20% HNO3. 3-Substituted rhodanines (IIIa) were prepared via the dithiocarbamate by an improved method. ClCH2CO2K was added to a mixture of 24% aqueous NH3, CS2, and a primary amine, EtOH added, and the mixture acidified and refluxed to precipitate the following IIIa (3-substituent, m.p., and starting amine given): phenyl, 194°, aniline; benzyl, 85°, benzylamine; p-nitrophenyl, 144°, p-nitroaniline. 3-Methylrhodanine, 3-aminorhodanine and N-rhodanineacetic acid were prepared according to published methods. The following 5-substituted derivatives of Ib, Ic, and 3-phenyl-4-thiazolidinone (IV) were obtained by condensation with aldehydes (5-substituent, parent, m.p., and reactants given): benzylidene, Ic, 202°, Ic and BzH; benzylidene, 3 phenylrhodanine, 186°, BzH and 3 phenylrhodanine; p-nitrobenzylidene, Ic, 270°, p-nitrobenzaldehyde and Ic; p-methoxybenzylidene, Ic, 245°, Ic and anisaldehyde; cinnamylidene, Ic, 216°, Ic and cinnamaldehyde; cyclohexylidene, Ic, 173°, Ic and cyclohexanone; butylidene Ic, -, Ic and butyraldehyde; heptylidene, Ic, -, Ic and heptanal; benzylidene, 2,4-thiazolidinedione, 243°, BzH and Ib; benzylidene, 2 imino-4-thiazolidinone, 230° (decomposition), Ia and BzH; benzylidene, IV, 205°, BzH and IV. Electrochem. study of the hydrolytic cleavage of the rhodanine derivatives suggested the following preparation of α-mercaptocinnamic acid (VI): V (1 mole) dissolved in 200 ml. 2M Me4NOH solution, was kept 48 hrs. at room temperature and acidified with HCl to precipitate 80% yellow VI, m. 124° (ethanol).

Bulletin de la Societe Chimique de France published new progress about 5053-24-7. 5053-24-7 belongs to thiazole, auxiliary class Thiazole,sulfides, name is 2-(Methylthio)thiazole, and the molecular formula is C4H5NS2, Related Products of thiazole.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Shook, Brian C. published the artcileMicrowave-assisted Sonogashira-type cross couplings of various heterocyclic methyl thioethers, COA of Formula: C4H5NS2, the publication is Tetrahedron Letters (2009), 50(9), 1013-1015, database is CAplus.

A novel, microwave-assisted, Pd-catalyzed Sonogashira-type coupling of terminal alkynes with a variety of heteroaryl Me thioethers is reported. The developed protocol allows for further utility and diversification of a number of chem. and biol. interesting scaffolds.

Tetrahedron Letters published new progress about 5053-24-7. 5053-24-7 belongs to thiazole, auxiliary class Thiazole,sulfides, name is 2-(Methylthio)thiazole, and the molecular formula is C5H9IO2, COA of Formula: C4H5NS2.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Ouimet, Nathalie published the artcileSubstituted heterocyclic analogs as selective COX-2 inhibitors in the flosulide class, SDS of cas: 5053-24-7, the publication is Bioorganic & Medicinal Chemistry Letters (1999), 9(2), 151-156, database is CAplus and MEDLINE.

Substituted heterocyclic analogs in the flosulide class were investigated as potential selective cyclooxygenase-2 inhibitors. 6-(4-Ethyl-2-thiazolylthio)-5-methanesulfonamido-3H-isobenzofuran-1-one was the optimal compound in the series with superior in vitro and in vivo anti-inflammatory activities.

Bioorganic & Medicinal Chemistry Letters published new progress about 5053-24-7. 5053-24-7 belongs to thiazole, auxiliary class Thiazole,sulfides, name is 2-(Methylthio)thiazole, and the molecular formula is C4H5NS2, SDS of cas: 5053-24-7.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Bouscasse, L. published the artcileComparison of experimental results obtained for Δ4-thiazoline-2-thiones and their 2-methylthiothiazole isomers with the values calculated by the PPP [Pariser-Parr-Pople] method, Related Products of thiazole, the publication is Bulletin de la Societe Chimique de France (1972), 1055-62, database is CAplus.

The 5-Me groups of 2-(methylthio)thiazole (I) increases the rate of quaternization by MeI, while the behavior of the Me group in II is just the opposite. The rate of formation of thiazolium iodides (III) from the 4-thiazoline-2-thiones (IV) is increased by the introduction of a 4-Me or 5-Me group. The positions of the uv absorption bands are in agreement with calculated electronic transition energies for I-IV.

Bulletin de la Societe Chimique de France published new progress about 5053-24-7. 5053-24-7 belongs to thiazole, auxiliary class Thiazole,sulfides, name is 2-(Methylthio)thiazole, and the molecular formula is C4H5NS2, Related Products of thiazole.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Bastianelli, Pierre published the artcileSynthesis in the 2-alkylthiothiazole series, Recommanded Product: 2-(Methylthio)thiazole, the publication is Bulletin de la Societe Chimique de France (1967), 1948-51, database is CAplus.

4-Thiazoline-2-thione (I) is prepared II are prepared from I, and N.M.R. data for the II are obtained. Thus, NH3 is introduced into a solution of CS2 in iso-PrOAc to give H2NCS2NH4; a solution of 143 g. H2NCS2NH4 in 250 ml. water is treated with 87.5 g. ClCH2CHO in water or EtOH to give 55% I, m. 80° (water). A mixture of 10 g. I, 25 g. MeI, and 200 ml. MeNO2 is refluxed 30 min. to give 90% 2-methylthiothiazole, b2 68°. Similarly prepared are the following II (R, b.p./mm., and % yield given): Et, 70°/2, 90; Pr, 54°/1, 80; iso-Pr, 66°/5, 80; tert-Bu, -, 53; PhCH2, 162°/2, 68. N.M.R., ir, and Rf (thin-layer chromatog.) data for the prepared II are given. According to the N.M.R. data, the protons of the side chains are deshielded by the thiazole ring.

Bulletin de la Societe Chimique de France published new progress about 5053-24-7. 5053-24-7 belongs to thiazole, auxiliary class Thiazole,sulfides, name is 2-(Methylthio)thiazole, and the molecular formula is C4H5NS2, Recommanded Product: 2-(Methylthio)thiazole.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Verkruijsse, H. D. published the artcileCarbophilic versus thiophilic attack in the reaction of metalated aromates and heteroaromates with carbon disulfide, Related Products of thiazole, the publication is Journal of Organometallic Chemistry (1987), 332(1-2), 95-8, database is CAplus.

CuBr catalyzed the formation of RCSSLi (R = Ph, 2-MeOC₆H₄, 2-FC₆H₄, 4-FC₆H₄, 2-thienyl, 3-thienyl, 2-furyl, N-methylpyrryl, N-methylimidazolyl, 2-thiazolyl, 2-methylthio-2-thiazolyl) in the reaction of aryl- or heteroaryllithium reagents with CS₂. Subsequent addition of MeI gave RCSSMe in 64-90% yields. Appreciable amounts of RSMe and tars were obtained when the reaction with CS₂ was carried out in the absence of CuBr especially in the case of more basic organoalkali compounds

Journal of Organometallic Chemistry published new progress about 5053-24-7. 5053-24-7 belongs to thiazole, auxiliary class Thiazole,sulfides, name is 2-(Methylthio)thiazole, and the molecular formula is C9H22OSi, Related Products of thiazole.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Kumar, Nag S. published the artcileSynthesis of a tritium-labeled photo-affinity probe based on an atypical leukotriene biosynthesis inhibitor, Synthetic Route of 5053-24-7, the publication is Journal of Labelled Compounds and Radiopharmaceuticals (2011), 54(1), 43-50, database is CAplus.

A radiolabeled photo-affinity probe containing a diazirine group was designed and synthesized based on an atypical leukotriene (LT) biosynthesis inhibitor to determine whether this type of inhibitor (such as 5) interacts with a novel protein, critical for LT biosynthesis. One of the key transformations was to introduce a tritium label in the thiazole ring. This was eventually achieved by treating the iodinated compound with tritium, Pt/C (sulfided) and triethylamine in anhydrous aprotic solvent, to give the tritiated compound I with a specific activity of 303 GBq/mmol. The affinity probe will be used to identify the proteins and protein complexes with which this type of mols. interacts with in inflammatory cells. Copyright © 2010 John Wiley & Sons, Ltd.

Journal of Labelled Compounds and Radiopharmaceuticals published new progress about 5053-24-7. 5053-24-7 belongs to thiazole, auxiliary class Thiazole,sulfides, name is 2-(Methylthio)thiazole, and the molecular formula is C4H5NS2, Synthetic Route of 5053-24-7.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Crawley, Graham C. published the artcileChiral Dioxolane Inhibitors of Leukotriene Biosynthesis: Structure-Activity Relationships and Syntheses Using Asymmetric Dihydroxylation, Recommanded Product: 2-(Methylthio)thiazole, the publication is Journal of Medicinal Chemistry (1995), 38(20), 3951-6, database is CAplus and MEDLINE.

1,3-Dioxolanes have been described as chiral inhibitors of 5-lipoxygenase (5LO). In the present work, this series has been developed further to provide agents which showed comparable or superior potency in vivo to ZD2138, a methoxytetrahydropyran inhibitor of 5LO, which is currently undergoing clin. evaluation. An asym. synthesis was developed of these dioxolanes based on asym. dihydroxylation. (S)-N-Methyl-4′-[[4-(2,2,4-trimethyl-1,3-dioxolan-4-yl)thien-2-yl]thio]acetanilide [(S)-I] inhibited leukotriene B₄ (LTB₄) synthesis in A23187-stimulated human whole blood in vitro with IC₅₀ 0.039 μM, 25-fold more potent than (R)-I. In vivo, (S)-I inhibited LTB₄ synthesis by 70% in zymosan-inflamed air pouch exudate in rat 10 h after an oral dose of 1.5 mg/kg. Structure-activity relationship considerations suggested that the dioxolane and methoxytetrahydropyran series are related, a conclusion which can be supported by mol. modeling.

Journal of Medicinal Chemistry published new progress about 5053-24-7. 5053-24-7 belongs to thiazole, auxiliary class Thiazole,sulfides, name is 2-(Methylthio)thiazole, and the molecular formula is C4H5NS2, Recommanded Product: 2-(Methylthio)thiazole.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Filatre-Furcate, Agathe published the artcileGold dithiolene complexes: easy access to 2-alkylthio-thiazoledithiolate complexes, Quality Control of 5053-24-7, the publication is Dalton Transactions (2015), 44(35), 15683-15689, database is CAplus and MEDLINE.

In the presence of MeI or EtI, N-tert-butyl-1,3-thiazoline-2-thione derivatives undergo a transformation to 2-alkylthio-thiazoledithiolate pro-ligands with elimination of the tert-Bu substituent. The corresponding Au^III dithiolene complexes [Au(RS-tzdt)₂]^– (R = Me, Et) oxidize readily to the neutral radical species, such as the semi-conducting [Au(EtS-tzdt)₂]^•, which organizes into dimers in the solid state.

Dalton Transactions published new progress about 5053-24-7. 5053-24-7 belongs to thiazole, auxiliary class Thiazole,sulfides, name is 2-(Methylthio)thiazole, and the molecular formula is C4H5NS2, Quality Control of 5053-24-7.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica