Month: November 2022

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

Tian, Qiaopeng published the artcileCharacterization of a robust cold-adapted and thermostable laccase from Pycnoporus sp. SYBC-L10 with a strong ability for the degradation of tetracycline and oxytetracycline by laccase-mediated oxidation, Application In Synthesis of 30931-67-0, the publication is Journal of Hazardous Materials (2020), 121084, database is CAplus and MEDLINE.

A native laccase (Lac-Q) with robust cold-adapted and thermostable characteristics from the white-rot fungus Pycnoporus sp. SYBC-L10 was purified, characterized, and used in antibiotic treatments. Degradation experiments revealed that Lac-Q at 10.0 U mL^-1 coupled with 1.0 mmol L^-1 ABTS could degrade 100% of the tetracycline or oxytetracycline (50 mg L^-1) within 5 min with a static incubation at 0 °C (pH 6.0). The presence of the Mn²⁺ ion inhibited the removal rate of tetracycline and oxytetracycline by the Lac-Q-ABTS system, and the presence of Al³⁺, Cu²⁺, and Fe³⁺ accelerated the removal rate of tetracycline and oxytetracycline by the Lac-Q-ABTS system. Furthermore, seven transformation products of oxytetracycline (namely TP 445, TP 431, TP 413, TP 399, TP 381, TP 367, and TP 351) were identified during the Lac-Q-mediated oxidation process by using UPLC-MS/MS. A possible degradation pathway including deamination, demethylation, and dehydration was proposed. Furthermore, the growth inhibition of Bacillus altitudinis SYBC hb4 and E. coli by tetracycline antibiotics revealed that the antimicrobial activity was significantly reduced after treatment with the Lac-Q-ABTS system. Finally, seven transformation products of oxytetracycline (namely TP 445, TP 431, TP 413, TP 399, TP 381, TP 367, and TP 351) were identified during the Lac-Q-mediated oxidation process by using UPLC-MS/MS. A possible degradation pathway including deamination, demethylation, and dehydration was proposed. These results suggest that the Lac-Q-ABTS system shows a great potential for the treatment of antibiotic wastewater containing different metal ions at various temperatures

Journal of Hazardous Materials published new progress about 30931-67-0. 30931-67-0 belongs to thiazole, auxiliary class Salt,Hydrazine,Amine,Benzothiazole, name is Ammonium 2,2′-(hydrazine-1,2-diylidene)bis(3-ethyl-2,3-dihydrobenzo[d]thiazole-6-sulfonate), and the molecular formula is C11H11NO2, Application In Synthesis of 30931-67-0.

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

Etse, Koffi Senam published the artcileDevelopment of Thiochroman Dioxide Analogues of Benzothiadiazine Dioxides as New Positive Allosteric Modulators of α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic Acid (AMPA) Receptors, Quality Control of 1204572-55-3, the publication is ACS Chemical Neuroscience (2021), 12(14), 2679-2692, database is CAplus and MEDLINE.

On the basis of the activity of 1,2,4-benzothiadiazine 1,1-dioxides as pos. allosteric modulators of AMPA receptors, thiochroman 1,1-dioxides were designed applying the isosteric replacement concept. The new compounds expressed strong modulatory activity on AMPA receptors in vitro, although lower than their corresponding benzothiadiazine analogs. The pharmacokinetic profile of three thiochroman 1,1-dioxides (12a, 12b, 12e) was examined in vivo after oral administration, showing that these compounds freely cross the blood-brain barrier. Structural anal. was achieved using X-ray crystallog. after cocrystn. of the racemic compound 12b in complex with the ligand-binding domain of GluA2 (L504Y/N775S). Interestingly, both enantiomers of 12b were found to interact with the GluA2 dimer interface, almost identically to its benzothiadiazine analog, BPAM344 (4). The interactions of the two enantiomers ((R)-12b (I) and (S)-12b (II)) in the cocrystal were further analyzed (mapping Hirshfeld surfaces and 2D fingerprint) and compared to those of 4. Taken together, these data explain the lower affinity on AMPA receptors of thiochroman 1,1-dioxides compared to their corresponding 1,2,4-benzothiadiazine 1,1-dioxides.

ACS Chemical Neuroscience published new progress about 1204572-55-3. 1204572-55-3 belongs to thiazole, auxiliary class Neuronal Signaling,GluR, name is 4-Cyclopropyl-7-fluoro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide, and the molecular formula is C10H11FN2O2S, Quality Control of 1204572-55-3.

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

Hodgson, Herbert H. published the artcileSome derivatives of benz-1-thia-2,3-diazole, the nature of the thiadiazole ring, and a note on the thiolation of 2-chloro-5-nitroaniline, Application of Benzo[d][1,2,3]thiadiazol-5-amine, the publication is Journal of the Chemical Society (1948), 870-4, database is CAplus.

2,5-Cl(O₂N)C₆H₃NH₂ (I) results in about 45% yield on treatment of 20.25 g. 2,4-(O₂N)₂C₆H₃Cl in 40 cc. boiling AcOH with 57 g. SnCl₂ and distillation with steam; an equal quantity of 4,3-Cl(O₂N)C₆H₃NH₂ is nonvolatile with steam. I (17.5 g.) in 250 cc. boiling EtOH, treated gradually with 36 g. Na₂S.9H₂O and 12.6 g. NaHCO₃ in 100 cc. H₂O, the mixture heated 1 h. on the water bath, treated with 20 cc. 20% NaOH, added to 750 cc. ice and H₂O, and 7 g. NaNO₂ added to the filtrate, which was poured into a mixture of 25 cc. concentrated H₂SO₄ and 250 g. ice, gives 97% 5-nitrobenzothiadiazole (II), m. 143-5°, sublimes at 80-100°/atm. pressure, volatility with steam about 1 g./l.; II in Me₂CO, treated with a drop aqueous NaOH, gives a violet color which is discharged by acid and restored by alkali; on standing the color slowly changes to brown. I. (1.725 g.) in 6 cc. boiling EtOH, treated with 1.8 g. Na₂S.9H₂O and 0.36 g. S in 2 cc. H₂O, the mixture heated 1 h. on the steam bath, and treated as above, gives 1.3 g. impure II. The above alk. mixture, shaken with 20% aqueous NaOH and Me₂SO₄, gives 4,2-O₂N(H₂N)C₆H₃SMe, m. 105° (Ac derivative, pale lemon-yellow, m. 157°); (2-methylmercapto-5-nitro-2-phenylazo)-2-naphthol, scarlet, m. 236°. A solution of 4,2-O₂N(H₂N)C₆H₃SNa, shaken at room temperature with Ac₂O, gives 4-nitro-2-(acetamidomercapto)phenyl acetate, pale cream, m. 150°. I (1.725 g.) in 96 cc. hot EtOH, treated with 0.36 g. S and 1.8 g. Na₂S.9H₂O in 2 cc. H₂O and the mixture refluxed 5 h., gives [4,2-O₂N(H₂N)C₆H₃]₂S, m. 218°. Reduction of 0.45 g. II in 20 cc. hot aqueous NaOH with 2 g. Na₂S₂O₄ gives 0.15 g. 5-aminobenzothiadiazole (III), yellow, m. 95°; reduction of 0.02 g.-mol. II with 0.24 g.-mol. Fe powder in 1 cc. H₂SO₄, 30 cc. H₂O, and 100 cc. EtOH (refluxed 3 h.) gives 82% III; diazotization of the filtrate and coupling with 2-naphthol gave 17% benzothiadiazol-5-ylazo-2-naphthol, bright red, m. 209°; H₂SO₄ gives a reddish pink color, changing to pale pink on dilution with H₂O. III, through the diazo reaction, yields 5-bromobenzothiadiazole, m. 106°, and the 5-I derivative, m. 103° (solubility of the latter in H₂O at room temperature 0.3 g./l.). The yields of thiol and monosulfide from I and Na₂S, Na₂S₂, Na₂S_2.5, and NaSH are given; Na₂S₂O₃ does not react with I. A cyclic structure is preferred for the thiadiazole ring in contrast to the quinonoid resonance structure of the analogous diazoöxides.

Journal of the Chemical Society published new progress about 1753-29-3. 1753-29-3 belongs to thiazole, auxiliary class Other Aromatic Heterocyclic,Amine, name is Benzo[d][1,2,3]thiadiazol-5-amine, and the molecular formula is C6H5N3S, Application of Benzo[d][1,2,3]thiadiazol-5-amine.

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

Yamano, Tomoyoshi published the artcileAire-expressing ILC3-like cells in the lymph node display potent APC features, Computed Properties of 95-24-9, the publication is Journal of Experimental Medicine (2019), 216(5), 1027-1037, database is CAplus and MEDLINE.

The autoimmune regulator (Aire) serves an essential function for T cell tolerance by promoting the “promiscuous” expression of tissue antigens in thymic epithelial cells. Aire is also detected in rare cells in peripheral lymphoid organs, but the identity of these cells is poorly understood. Here, we report that Aire protein-expressing cells in lymph nodes exhibit typical group 3 innate lymphoid cell (ILC3) characteristics such as lymphoid morphol., absence of “classical” hematopoietic lineage markers, and dependence on RORγt. Aire+ cells are more frequent among lineage-neg. RORγt+ cells of peripheral lymph nodes as compared with mucosa-draining lymph nodes, display a unique Aire-dependent transcriptional signature, express high surface levels of MHCII and costimulatory mols., and efficiently present an endogenously expressed model antigen to CD4+ T cells. These findings define a novel type of ILC3-like cells with potent APC features, suggesting that these cells serve a function in the control of T cell responses.

Journal of Experimental Medicine published new progress about 95-24-9. 95-24-9 belongs to thiazole, auxiliary class Organic Pigment, name is 6-Chlorobenzothiazol-2-ylamine, and the molecular formula is C8H11BO2, Computed Properties of 95-24-9.

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

Pajnik, Jelena published the artcileZeolite/Chitosan/Gelatin Films: Preparation, Supercritical CO₂ Processing, Characterization, and Bioactivity, Category: thiazole, the publication is Macromolecular Materials and Engineering (2022), 307(8), 2200009, database is CAplus.

Chitosan/gelatin and chitosan/gelatin/zeolite films prepared by solvent casting method are impregnated with a mixture of thymol and carvacrol using a green solvent, supercritical carbon dioxide at 35 °C and 30 MPa, during 18 h. Proposed method enables preparation of biocompatible and biodegradable blends with strong antioxidant and antibacterial activity, whereby amounts of loaded thymol/carvacrol (TC) mixture are in the range from 3.3% to 6%. After initial burst release, both types of films exhibit gradual release of bioactive compounds, with around 72% and 96% of impregnated TC mixture released in water and phosphate buffered saline solution (pH 7.4) during tested period of 10 days, resp. Results of water vapor transmission rate (>76 g m^-2 day^-1) confirm that prepared composites are suitable for wound dressing application. Thermal anal. shows superior properties of prepared TC loaded films compared to control samples. In addition, mech. and structural properties, as well as solubility and swelling behavior of the obtained films are investigated in detail.

Macromolecular Materials and Engineering published new progress about 30931-67-0. 30931-67-0 belongs to thiazole, auxiliary class Salt,Hydrazine,Amine,Benzothiazole, name is Ammonium 2,2′-(hydrazine-1,2-diylidene)bis(3-ethyl-2,3-dihydrobenzo[d]thiazole-6-sulfonate), and the molecular formula is C18H24N6O6S4, Category: thiazole.

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

Song, Jung Min published the artcileA tetra(ethylene glycol) derivative of benzothiazole aniline ameliorates dendritic spine density and cognitive function in a mouse model of Alzheimer’s disease, Recommanded Product: 2-(4-Aminophenyl)-6-methylbenzothiazole, the publication is Experimental Neurology (2014), 105-113, database is CAplus and MEDLINE.

We recently reported that the tetra(ethylene glycol) derivative of benzothiazole aniline, BTA-EG₄, acts as an amyloid-binding small mol. that promotes dendritic spine d. and cognitive function in wild-type mice. This raised the possibility that BTA-EG₄ may benefit the functional decline seen in Alzheimer’s disease (AD). In the present study, we directly tested whether BTA-EG₄ improves dendritic spine d. and cognitive function in a well-established mouse model of AD carrying mutations in APP, PS1 and tau (APP_swe;PS1_M146V;tau_P301L, 3xTg AD mice). We found that daily injections of BTA-EG₄ for 2 wk improved dendritic spine d. and cognitive function of 3xTg AD mice in an age-dependent manner. Specifically, BTA-EG₄ promoted both dendritic spine d. and morphol. alterations in cortical layers II/III and in the hippocampus at 6-10 mo of age compared to vehicle-injected mice. However, at 13-16 mo of age, only cortical spine d. was improved without changes in spine morphol. The changes in dendritic spine d. correlated with Ras activity, such that 6-10 mo old BTA-EG₄ injected 3xTg AD mice had increased Ras activity in the cortex and hippocampus, while 13-16 mo old mice only trended toward an increase in Ras activity in the cortex. Finally, BTA-EG₄ injected 3xTg AD mice at 6-10 mo of age showed improved learning and memory; however, only minimal improvement was observed at 13-16 mo of age. This behavioral improvement corresponds to a decrease in soluble Aβ 40 levels. Taken together, these findings suggest that BTA-EG₄ may be beneficial in ameliorating the synaptic loss seen in early AD.

Experimental Neurology published new progress about 92-36-4. 92-36-4 belongs to thiazole, auxiliary class Organic Pigment, name is 2-(4-Aminophenyl)-6-methylbenzothiazole, and the molecular formula is C4H10Br2CoO2, Recommanded Product: 2-(4-Aminophenyl)-6-methylbenzothiazole.

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

Shetgar, Sanjay Shesha published the artcileDevelopment and validation of UPLC method for quantitative estimation of related impurities in tizanidine hydrochloride tablets, Quality Control of 30536-19-7, the publication is Journal of Applied Pharmaceutical Science (2021), 11(8), 043-053, database is CAplus.

Tizanidine hydrochloride is known to have several related impurities depending on the manufacturing process. There is no published ultra-performance liquid chromatog. (UPLC) method which can simultaneously quantify these impurities. The current work is to design, develop, and validate an UPLC method for simultaneous estimation of all known impurities. Forced degradation studies performed on tablet formulation did not show any purity flags. To achieve sensitive and optimal separation of all the six impurities from the main moiety of Tizanidine, gradient UPLC system with ethylene bridged hybrid C8 column, 230 nm UV detection provided an optimum separation The developed method was quick, with all six impurities eluting within 11 min. Low level of impurities could be quantified with limit of detection in the range 0.008%-0.028% and limit of quantitation in the range 0.037%-0.057%. Recoveries of all spiked impurities in Tizanidine hydrochloride were well within the range of 85%-115%. Thus, the developed UPLC method is sensitive, fast, and provides precise and accurate quantitation of all known impurities in Tizanidine hydrochloride tablets. The developed method is very useful for quant. estimation of impurities in Tizanidine hydrochloride tablets in routine quality control as well as stability monitoring programs. The method can easily be extended to quant. cleaning residue determination in pharmaceutical industry.

Journal of Applied Pharmaceutical Science published new progress about 30536-19-7. 30536-19-7 belongs to thiazole, auxiliary class Other Aromatic Heterocyclic,Chloride,Amine, name is 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine, and the molecular formula is C42H63O3P, Quality Control of 30536-19-7.

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

Singh, Manjula published the artcileVisible-light photoredox catalytic approach for the direct synthesis of 2-aminobenzothiazoles from anilines, Application of 6-Chlorobenzothiazol-2-ylamine, the publication is Tetrahedron Letters (2020), 61(13), 151700, database is CAplus.

A novel, highly efficient and convenient approach for the visible-light-promoted direct synthesis of 2-aminobenzothiazoles from anilines and ammonium thiocyanate is presented. The reaction involves addition/cyclization cascade of SCN radical and anilines under photoredox catalysis with Ru(bpy)3Cl₂. The salient features of the protocol include the utilization of atm. oxygen and visible light as clean, inexpensive and sustainable resources at room temperature

Tetrahedron Letters published new progress about 95-24-9. 95-24-9 belongs to thiazole, auxiliary class Organic Pigment, name is 6-Chlorobenzothiazol-2-ylamine, and the molecular formula is C8H14O2, Application of 6-Chlorobenzothiazol-2-ylamine.

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

Akhil published the artcileComparative evaluation of laccase mediated oxidized and unoxidized lignin of sugarcane bagasse for the synthesis of lignin-based formaldehyde resin, HPLC of Formula: 30931-67-0, the publication is Industrial Crops and Products (2020), 112385, database is CAplus.

Pretreatment using dilute acid is one of the strategies employed in a lignocellulosic biorefinery. The current study deals with the isolation, characterization, and oxidation of lignin from the enzymic residue of acid pre-treated sugarcane bagasse. The study also focused on evaluating the reactivity of Laccase mediated oxidized lignin with the non-oxidized one for the preparation of lignin-based formaldehyde (LF) resin. In the current study, 100% phenolic lignin was utilized for the synthesis of LF resin. Three different approaches (Alk. hydrolysis, mild acidolysis & organosolv) have been employed to evaluate the effect of isolation method on the physicochem. properties of lignin. The isolation method had a bearing on the properties of lignin and its reactivity towards formaldehyde for the synthesis of LF resin. Alkali and organosolv lignin were found as promising candidates for the preparation of LF resin. Oxidized lignin exhibited better reactivity than the non-oxidized one.

Industrial Crops and Products published new progress about 30931-67-0. 30931-67-0 belongs to thiazole, auxiliary class Salt,Hydrazine,Amine,Benzothiazole, name is Ammonium 2,2′-(hydrazine-1,2-diylidene)bis(3-ethyl-2,3-dihydrobenzo[d]thiazole-6-sulfonate), and the molecular formula is C18H24N6O6S4, HPLC of Formula: 30931-67-0.

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