Category: thiazole

Nuhn, P. published the artcileGlycosides of heterocycles. XXX. Glucosides of imidazole-, oxazole-, and thiazole-2-thiones, Synthetic Route of 5053-24-7, the publication is Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft (1968), 301(3), 186-200, database is CAplus and MEDLINE.

(cf. CA 68:39990b; 40021t. The reaction of tetra-O-acetyl-α-D-glucopyranosyl bromide (I) with thiazole-2-thiones carried out by the Sabalitschka method (CA 23:3239), i.e. under SN2 conditions, gave exclusively 1-thio-D-glucosides. Similar results were obtained with oxazole-2-thiones and imidazole-2-thiones. Under SN1 conditions the formation of 1-thio-D-glucosides was favored only when the heterocyclic ring bore bulky substituents at position 4, otherwise the formation of glycosytamines was preferred. 2-Thmzolethione (II) (0.01 mole) and 0.56 g. KOH in 5 ml. H2O was mixed with 4.1 g. I in 15 ml. Me2CO, agitated until the mixture turned neutral and worked-up to give 65% 2-(tetra-O-acetyl-β-D- glucopyranosylthio)thiazole (IIIa) (Q = tetra-O-acetyl-β-D-glucopyranosyl throughout this abstract), m. 119-22° (MeOH), [α]22D -10.7° (c 5, CHCl3). IIIb, m. 107-8° (50% MeOH), [α]22D -11.7° (c5, CHCl3), and IIIc, m. 151-3° (MeOH), [α]22D -31.7° (c5, CHCl3), were similarly prepared Deacetylation with MeONa afforded the free glucosides: 2-(β-D-glucopyranosylthio)-4-methylthiazole (IIId) (G = β-D-glucopyranosyl throughout this abstract), m. 152-5°, [α]22D -66.8° (c 2, H2O), and IIIe, m. 87-90° (H2O), [α]22D -62.9° (c 2, H2O). Using the same procedure as for IIIa, 4-methyloxazole-2-thione (IV) afforded 4-methyl-2-(tetra-O-acetyl-β-D-glucopyranosylthio)oxazole (Va), m. 105-10°, [α]22D -17° (c 5, CHCl3). Vb, m. 160-3° (MeOH), [α]22D -22° (c 5, CHCl3), and Vc, m. 117-19° (MeOH), [α]22D -13.9° (c 5, CHCl3), were prepared similarly. Tetra-o-acetylglucosides, deacetylated as previously, yielded the free glucosides: Vd, m. 125-8°, [α]22D -49.5° (c 2, H2O); Ve, m. 137-40°,α]22D -63.2° (c 2, H2O); and Vf, m. 85-90°, [α]25D -54.5° (c 1.5, Me2CO). 1-Methylimidazole-2-thione (VI) reacted with I under the Sabalitschka method gave 55% of 1-methyl-2-(tetra-O-acetyi-1-β-D-glucopyranosylthio)imidazole (VII), m. 99-102° (70% EtOH), [α]22D 0° (CHCl3). II (0.01 mole) dissolved in 10 ml. H2O containing 0.56 g. KOH and the solution treated slowly with a solution of 2.72 g. HgCl2 and 2 g. NaCl in 40 ml. H2O yielded bis(2-thiazolythio)mercury (VIII), m. 182-90° (decomposition). VIII (0.005 mole) was dissolved in 30 ml. HCONMe2, the solution mixed with 30 ml. C6H6, the latter distilled and the remaining dry solution treated with 4.1 g. I, kept 14 hrs. at 50°, diluted with 200 ml. H2O, extracted 5 times with CHCl3, the combined extracts washed with 30% KI followed by 5% Na2CO2, dried and evaporated, gave 50% 3-(tetra-O-acetyl-1-β-D-glucopyranosyl)thiazole-2-thione (IXa), m. 179-82° (MeOH), [α]22D 68.3° (c 5, CHCl3). IXa deacetylated as previously, afforded IXb, m. 173-83°, [α]22D 35° (c 2, H2O). Similarly, bis(1-methylimidazol-2-ylthio)mercury, m. 220-5° (decomposition), produced 25% 1-methyl-3-(tetra-O-acetyl-β-D-glucopyranosyl)imidazole-2-thione (X), m. 148-9° (MeOh), α]23D 36° (c 5, CHCl3). VI (0.02 mole), refluxed with 6 ml. (Me3Si)2NH for 8 hrs. gave 1-methyl-3-trimethylsilylimidazole-2-thione, b9 142-3°. This, heated for 2 hrs. with I at 120-30° in vacuo, diluted with 100 ml. CHCl3 and the solution washed with 5% Na2CO3 yielded 30% X. Similarly, 2-trimethylsilylthiothiazole, b. 143-5°, afforded IIIa, while 2-trimethylsilylthio-4-phenyloxazole, b9 147-51°, gave 72% Vb. 1-Thio-D-glucosides heated in toluene with HgBr2 were converted in high yield into glycosylamines. Thus, IIIa (2.5 millimoles) was refluxed 5 hrs. with 0.9 g. HgBr2 in 50 ml. of dry toluene, the solution washed with 30% KI followed by 5% Na2CO3, dried and evaporated to give 95% IXa. Likewise, VII produced 73% X, Va gave 20% 3-(tetra-O-acetyl-β-D-glucopyranosyl)-4-methyloxazole-2-thione (XIa), m. 163-6° (MeOH), [α]22D 73.8° (c 5, CHCl3), while Vc yielded 55% XIb, m. 143-5° (MeOH), [α]22D -47.4° (c 5, CHCl3). Deacetylation of XIb afforded XIc, m. 200-5°, [α]20D -3.5° (c2, HCONMe2). Transglycosylation of IIIb resulted in 25% IXc, m. 192-4°, [α]22D 66° (c 5, CHCl3). In the case of 4-Ph derivatives, no conversion into glycosylamines was observed. Instead, partial anomerization occurred: Vb yielded 5% of 2-(tetra-O-acetyl-α-D-glucopyranosylthio)-4-phenylthiazole, m. 102-6° (MeOH), [α]22D 156° (c 5, CHCl3), while IIIc gave 30% 2-(tetra-O-acetyl-α-D-glucopyranosylthio)-4-phenyloxazole, m. 138-40° (MeOH), [α]22D 228° (c 5, CHCl8), which on deacetylation afforded the free glucoside, an amorphous solid, [α]22D 226° (c 2, H2O). AcCH2OH (3 g.) dissolved in 40 ml. EtOH, treated with 5.8 g. KCNS and 3 ml. concentrated HCl and refluxed 24 hrs. gave 65% 4-methyloxazole-2-thione (XII), m. 149-52° (MeOH). II (2 g.), 5 g. Ag2O, and 15 g. MeI refluxed 8 hrs. gave 80% 2-methylthiothiazole, b26 59-62°. Similarly, XII yielded 2-(methylthio)-4-methyloxazole, b8 44-5°.

Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft 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

Xu, Wenqing published the artcileRedox Properties of Pyrogenic Dissolved Organic Matter (pyDOM) from Biomass-Derived Chars, Category: thiazole, the publication is Environmental Science & Technology (2021), 55(16), 11434-11444, database is CAplus and MEDLINE.

Chars are ubiquitous in the environment and release significant amounts of redox-active pyrogenic dissolved organic matter (pyDOM). Yet, the redox properties of pyDOM remain poorly characterized. This work provides a systematic assessment of the quantity and redox properties of pyDOM released at circumneutral pH from a total of 14 chars pyrolyzed from wood and grass feedstocks from 200 to 700°C. The amount of released pyDOM decreased with increasing pyrolysis temperature of chars, reflecting the increasing degree of condensation and decreasing char polarity. Using flow-injection anal. coupled to electrochem. detection, we demonstrated that electron-donating capacities (EDC_pyDOM; up to 6.5 mmol_e-·g_C^-1) were higher than electron-accepting capacities (EAC_pyDOM; up to 1.2 mmol_e-·g_C^-1) for all pyDOM specimens. The optical properties and low metal contents of the pyDOM implicate phenols and quinones as the major redox-active moieties. Oxidation of a selected pyDOM by the oxidative enzyme laccase resulted in a 1.57 mmol_e-·g_C^-1 decrease in EDC_pyDOM and a 0.25 mmol_e-·g_C^-1 increase in EAC_pyDOM, demonstrating a largely irreversible oxidation of presumably phenolic moieties. Non-mediated electrochem. reduction of the same pyDOM resulted in a 0.17 mmol_e-·g_C^-1 increase in EDC_pyDOM and a 0.24 mmol_e-·g_C^-1 decrease in EAC_pyDOM, consistent with the largely reversible reduction of quinone moieties. Our results imply that pyDOM is an important dissolved redox-active phase in the environment and requires consideration in assessing and modeling biogeochem. redox processes and pollutant redox transformations, particularly in char-rich environments.

Environmental Science & Technology 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 C9H12O, Category: thiazole.

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

Wang, Lu published the artcileFacile syntheses of 3-trifluoromethylthio substituted thioflavones and benzothiophenes via the radical cyclization, Synthetic Route of 95-24-9, the publication is Chinese Chemical Letters (2021), 32(1), 389-392, database is CAplus.

The 3-CF₃S substituted thioflavones I (R¹ = C₆H₅, 4-ClC₆H₄, 2-thienyl, etc.; R² = Br) and benzothiophenes II (R³ = C₆H₅, 4-FC₆H₄, 2-thienyl, etc.; R⁴ = 6-Me, 6-Cl, 4,6-(Cl)2, etc.) were achieved via the reactions of AgSCF₃ with methylthiolated alkynones 2-(SMe)-5-BrC₆H₃C(O)CCR¹ and alkynylthioanisoles, R⁵CCR³ (R⁵ = 4-chloro-2-(methylsulfanyl)phenyl, 5-methyl-2-(methylsulfanyl)phenyl, 2,4-difluoro-6-(methylsulfanyl)phenyl, etc.) resp., promoted by persulfate. This protocol possesses good functional group tolerance and high yields. Mechanistic studies suggested that a classic two-step radical process involves addition of CF₃S radical to triple bond and cyclization with SMe moiety.

Chinese Chemical 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 C16H14O6, Synthetic Route of 95-24-9.

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

Du, Hongying published the artcileClassification structure-activity relationship (CSAR) studies for prediction of genotoxicity of thiophene derivatives, Recommanded Product: 2-(4-Aminophenyl)-6-methylbenzothiazole, the publication is Toxicology Letters (2008), 177(1), 10-19, database is CAplus and MEDLINE.

The grid search support vector machine (GS-SVM) was used to build a classification structure-activity relationship (CSAR) model and to predict the genotoxicity property of 140 thiophene derivatives with the information derived from the compounds’ mol. structures. The seven descriptors selected by linear discriminant anal. (LDA) were used as the inputs to develop the GS-SVM model. Using the Grid Search method, a satisfactory model with a good predictive capability was obtained. The quality of the models was evaluated by the number of right classified compounds The total accuracy of the LDA model was 81.4% and 85.2% for the training set and test set, resp., and to the GS-SVM model was 92.9% and 92.6%, resp. It was proved that the GS-SVM method was a very useful modeling approach with good classification ability for the genotoxicity of the thiophene derivatives This work also provides a new idea and an alternative method to investigate the genotoxicity of the similar structures with thiophene derivatives, and can be extended to other toxicity studies.

Toxicology Letters 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 C14H12N2S, Recommanded Product: 2-(4-Aminophenyl)-6-methylbenzothiazole.

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

Zhao, Mengxin published the artcileA highly selective and sensitive colorimetric assay for specific recognition element-free detection of uranyl ion, Application In Synthesis of 30931-67-0, the publication is Sensors and Actuators, B: Chemical, database is CAplus.

Current strategies for visual detection of uranyl ion (UO²⁺2) often require DNAzymes and organophosphorus receptors as well as various nanomaterials that may affect the selectivity, sensitivity, and accuracy in a complicated environment. Here, we circumvent these drawbacks by introducing a formic acid (FA)-assisted photolysis of UO²⁺2 initiated chromogenic reaction for specific recognition element-free colorimetric detection of UO²⁺2. The colorless 2, 2â€?azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt (ABTS) is oxidized by the superoxide anion from the photolysis of UO²⁺2 to generate green ABTS radical, which enables the determination of UO²⁺2 at a concentration of 0.5 μM with the naked eye. The present colorimetric assay is able to determine concentrations of UO²⁺2 from 0.1 to 100 μM, with a limit of detection as low as 0.01 μM. Impressively, the specific recognition element-free colorimetric assay possesses excellent selectivity over common inoganic ions with even 50-fold higher concentration than UO²⁺2. In addition to good sensitivity and selectivity, this colorimetric assay is also capable of determining UO²⁺2 in natural water samples with satisfactory recoveries.

Sensors and Actuators, B: Chemical 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 C3H12Cl2N2, Application In Synthesis of 30931-67-0.

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

Qi, Mei-Ling published the artcileValidated liquid chromatography method for assay of tizanidine in drug substance and formulated products, Quality Control of 30536-19-7, the publication is Analytica Chimica Acta (2003), 478(2), 171-177, database is CAplus.

A new isocratic stability indicating HPLC method for determination of tizanidine in drug substance and formulated products is described. Chromatog. separation of tizanidine from the related substances and degraded products was achieved with a Hypersil CN column (150 mm×5.0 mm, 5 μm) using a mobile phase comprising a mixture of an ion-pairing solution of heptanesulfonic acid sodium salt (HAS), methanol and acetonitrile (50:57:18 (volume/volume)) within 10 min. The flow-rate was 1.0 mL/min and detection was made at 227 nm. The method has good selectivity towards tizanidine, related substances and degraded products. Limits of quantitation for tizanidine and its synthetic intermediates were determined, ranging from 0.051 to 0.54 μg/mL. The linearity range was found to be 2-20 μg/mL (r=0.9998, n=5). Mean recovery for tizanidine from the tablets was from 99.5 to 99.8%. Precision of the method was 1.0% (n=9). The method can be used for routine anal. and the quality control of tizanidine drug substance and its formulated products.

Analytica Chimica Acta 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 C6H4ClN3S, Quality Control of 30536-19-7.

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

Kuhnert-Brandstaetter, Maria published the artcileThermal analytical and infrared spectroscopic investigations on polymorphic organic compounds. V., Computed Properties of 92-36-4, the publication is Mikrochimica Acta (1989), 3(1-2), 125-36, database is CAplus.

All the polymorphic compounds described are enantiotropic, so that in four cases, order-disorder or rotational transformation can be deduced on the basis of the relationships between enthalpy of transformation and enthalpy of fusion. The following compounds are of this type: (±)-1-azabicyclo[2.2.2]octan-3-ol (4 modifications), 5-norbornene-2,3-dicarboxylic anhydride (3 modifications), (1R)-(-)-camphorquinone (3 modifications) and 2-bromoethylamine-HBr (3 modifications). For tris(acetylacetonato)aluminum(III) (3 modifications) and 2-(4-aminophenyl)-6-methylbenzothiazole (5 modifications), another type of transformation must be assumed.

Mikrochimica Acta 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 C14H12N2S, Computed Properties of 92-36-4.

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

Chen, Chao published the artcileSynthesis and biological evaluation of thiazole derivatives as novel USP7 inhibitors, HPLC of Formula: 774230-95-4, the publication is Bioorganic & Medicinal Chemistry Letters (2017), 27(4), 845-849, database is CAplus and MEDLINE.

Herpesvirus-associated Ubiquitin-Specific Protease (HAUSP, also called USP7) interacts with and stabilizes Mdm2, and represents one of the first examples that deubiquitinases oncogenic proteins. USP7 has been regarded as a potential drug target for cancer therapy. Inhibitors of USP7 have been recently shown to suppress tumor cell growth in vitro and in vivo. Based on leading USP7 inhibitors P5091 and P22077, we designed and synthesized a series of thiazole derivatives The results of in vitro assays showed that the thiazole compounds, e.g., I, exhibited low micromolar inhibition activity against both USP7 enzyme and cancer cell lines. The compounds induced cell death in a p53-dependent and p53-independent manner. Taken together, this study may provide thiazole compounds as a new class of USP7 inhibitors.

Bioorganic & Medicinal Chemistry Letters published new progress about 774230-95-4. 774230-95-4 belongs to thiazole, auxiliary class Thiazole,Chloride,Aldehyde, name is 5-Chlorothiazole-2-ethanone, and the molecular formula is C5H4ClNOS, HPLC of Formula: 774230-95-4.

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

Lee, Nathanael J. published the artcileHexa (ethylene glycol) derivative of benzothiazole aniline promotes dendritic spine formation through the RasGRF1-Ras dependent pathway, Recommanded Product: 2-(4-Aminophenyl)-6-methylbenzothiazole, the publication is Biochimica et Biophysica Acta, Molecular Basis of Disease (2016), 1862(2), 284-295, database is CAplus and MEDLINE.

The authors’ recent study demonstrated that an amyloid-β binding mol., BTA-EG4, increases dendritic spine number via Ras-mediated signaling. To potentially optimize the potency of the BTA compounds, the authors synthesized and evaluated an amyloid-β binding analog of BTA-EG4 with increased solubility in aqueous solution, BTA-EG6. The authors initially examined the effects of BTA-EG6 on dendritic spine formation and found that BTA-EG6-treated primary hippocampal neurons had significantly increased dendritic spine number compared to control treatment. In addition, BTA-EG6 significantly increased the surface level of AMPA receptors. Upon investigation into the mol. mechanism by which BTA-EG6 promotes dendritic spine formation, the authors found that BTA-EG6 may exert its effects on spinogenesis via RasGRF1-ERK signaling, with potential involvement of other spinogenesis-related proteins such as Cdc42 and CDK5. Taken together, the authors’ data suggest that BTA-EG6 boosts spine and synapse number, which may have a beneficial effect of enhancing neuronal and synaptic function in the normal healthy brain.

Biochimica et Biophysica Acta, Molecular Basis of Disease 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 C14H12N2S, Recommanded Product: 2-(4-Aminophenyl)-6-methylbenzothiazole.

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

Thepchuay, Yanisa published the artcilePaper-based colorimetric biosensor of blood alcohol with in-situ headspace separation of ethanol from whole blood, Synthetic Route of 30931-67-0, the publication is Analytica Chimica Acta (2020), 115-121, database is CAplus and MEDLINE.

This work presents a novel development that exploits the concept of in-situ gas-separation together with a specific enzymic colorimetric detection to produce a portable biosensor called “Blood Alc. Micro-pad” for direct quantitation of ethanol in whole blood. The thin square device (25 mm × 25 mm × 1.8 mm) comprises two layers of patterned filter paper held together with a double-sided mounting tape with an 8-mm circular hole (the headspace). In operation, the reagent is deposited on one layer and covered with sticky tape. Then 8μL of a blood sample is dispensed onto the opposite layer and covered with sticky tape. Diffusion of ethanol across the 1.6 mm narrow headspace permits selective detection of ethanol by the enzymic reagents deposited on the opposite layer. This reagent zone contains alc. oxidase, horseradish peroxidase and 2′-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt, as the chromogenic reagent. The color intensity, measured from the recorded digital image, resulting from the enzymic assay of ethanol, correlates with the concentration of blood alc. The results obtained with spiked mice and sheep blood samples, using an external calibration in the range of 1-120 mg dL^-1ethanol, gave recoveries of 93.2-104.4% (n = 12). The “Blood Alc. Micro-pad” gave good precision with %RSD <1 (50 mg dL^-1 ethanol, n = 10) and limit of quantification (10SD of intercept/slope) of 11.56 mg dL^-1. The method was successfully validated against a headspace gas chromatog.-mass spectrometric method. It has good potential for development as a simple and convenient blood alc. sensor for on-site testing.

Analytica Chimica Acta 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 C11H15NOS, Synthetic Route of 30931-67-0.

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