Heterocyclic Building Blocks-Thiazole

Ni, Qijian published the artcileOrganocatalytic asymmetric [4+2] cyclization of 2-benzothiazolimines with azlactones: access to chiral benzothiazolopyrimidine derivatives, Computed Properties of 95-24-9, the publication is Chemical Communications (Cambridge, United Kingdom) (2020), 56(21), 3155-3158, database is CAplus and MEDLINE.

An organocatalytic asym. domino Mannich/cyclization reaction between 2-benzothiazolimines I (R = H, 6-OMe, 5-Br, etc.; R¹ = Ph, 4-MeC₆H₄, 2-thienyl, etc.) with azlactones II (R² = Me, Bn, 4-FC₆H₄CH₂, etc.; R³ = Ph, 4-MeC₆H₄, 1-naphthyl, etc.) has been successfully developed. With the bifunctional squaramide catalyst, this formal [4+2] cyclization occurs with good to high yields and excellent stereoselectivities (up to 99% ee, >20 : 1 dr), providing an efficient and mild access to chiral benzothiazolopyrimidines III (R = H, 6-OMe, 5-Br, etc.; R¹ = Ph, 4-MeC₆H₄, 2-thienyl, etc.; R² = Me, Bn, 4-FC₆H₄CH₂, etc.; R³ = Ph, 4-MeC₆H₄, 1-naphthyl, etc.) bearing adjacent tertiary and quaternary stereogenic centers.

Chemical Communications (Cambridge, United Kingdom) 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 C7H5ClN2S, Computed Properties of 95-24-9.

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

Deng, Qihuan published the artcileExtraction optimization of polysaccharides from Gougunao tea and assessment of the antioxidant and hypoglycemic activities of its fractions in vitro, Application In Synthesis of 30931-67-0, the publication is Bioactive Carbohydrates and Dietary Fibre (2021), 100287, database is CAplus.

The extraction optimization, characterization, antioxidant activities and hypoglycemic in vitro of polysaccharides from Gougunao tea (GTP) were investigated in this study. The extraction conditions were optimized as extraction time of 3.2 h, solid-liquid ratio of 1:30 (g/mL) and extraction temperature of 95 °C, reaching a maximum yield of 10.78 0.21%. Three new fractions (GTP40, GTP60 and GTP80) were separated from GTP by gradient concentrations of ethanol. Their weight-average mol. weight, number-average mol. weight and polydispersity index were determined to be 48286-195451 Da, 33946-118948 Da, 1.422-1.643 by the high-performance gel permeation chromatog. (HPGPC). Chem. anal. revealed that they were all composed of arabinose, galactose, ribose, glucose, rhamnose, manose, xylose, glucuronic acid, and galacturonic acid with different molar ratios, as well as a small amount of proteins. What′s remarkable is that the antioxidant and hypoglycemic activities in vitro of them were all in the order of GTP40>GTP60>GTP80 in a concentration-dependent manner. The half inhibition concentrations (IC₅₀) of GTP40 for 2,2-Diphenyl-1-picrylhydrazyl radical, 2,2â€?Azino-bis (3-ethylbenzothiazoline- 6-sulfonic acid) radical, hydroxyl radical were 0.066 mg/mL, 0.255 mg/mL and 3.610 mg/mL, and for a-amylase and a-glucosidase were 1.271 mg/mL and 0.013 mg/mL, resp. It will provide a theor. basis for the further utilization of polysaccharides from Gougunao tea.

Bioactive Carbohydrates and Dietary Fibre 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, Application In Synthesis of 30931-67-0.

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

Qiao, Jennifer X. published the artcile4-Benzothiazole-7-hydroxyindolinyl Diaryl Ureas Are Potent P2Y₁ Antagonists with Favorable Pharmacokinetics: Low Clearance and Small Volume of Distribution, Safety of 5-Chlorothiazolo[5,4-b]pyridin-2-amine, the publication is ChemMedChem (2014), 9(10), 2327-2343, database is CAplus and MEDLINE.

Current antithrombotic discovery efforts target compounds that are highly efficacious in thrombus reduction with less bleeding liability than the standard of care. Preclin. data suggest that P2Y₁ antagonists may have lower bleeding liabilities than P2Y₁₂ antagonists while providing similar antithrombotic efficacy. This article describes the continuous SAR efforts in a series of 7-hydroxyindolinyl diaryl ureas. When dosed orally, 4-trifluoromethyl-7-hydroxy-3,3-dimethylindolinyl analog I was highly efficacious in a model of arterial thrombosis in rats with limited bleeding. The chem. labile CF₃ group in I was then transformed to various groups via a novel one-step synthesis, yielding a series of potent P2Y₁ antagonists. Among them, the 4-benzothiazole-substituted indolines had desirable PK properties in rats, specifically, low clearance and small volume of distribution. In addition, compound II had high i.v. exposure and modest bioavailability, giving it the best overall profile.

ChemMedChem published new progress about 31784-71-1. 31784-71-1 belongs to thiazole, auxiliary class Other Aromatic Heterocyclic,Chloride,Amine, name is 5-Chlorothiazolo[5,4-b]pyridin-2-amine, and the molecular formula is C6H4ClN3S, Safety of 5-Chlorothiazolo[5,4-b]pyridin-2-amine.

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

Chen, Haiqiang published the artcileA novel antioxidant peptide purified from defatted round scad (Decapterus maruadsi) protein hydrolysate extends lifespan in Caenorhabditis elegans, Computed Properties of 30931-67-0, the publication is Journal of Functional Foods (2020), 103907, database is CAplus.

The residue rich in protein (up to 88.78%) obtained from round scad (Decapterus maruadsi) after oil extraction, was hydrolyzed by Alcalase to produce antioxidative peptides. The hydrolyzate was separated by ultrafiltration, Sephadex G-15 and RP-HPLC, and the active fractions were screened by 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2′-azino-bis (3-ethylbenzothiazoline- 6 sulfonic acid) diammonium salt (ABTS), reducing power and oxygen radical absorbance capacity (ORAC). The obtained peptide with the highest antioxidative activity was then analyzed by HPLC and LC-MS/MS and its anti-aging effect was examined using Caenorhabditis elegans (C. elegans) model. The peptide (Ile-Leu-Gly-Ala-Thr-Ile-Asp-Asn-Ser-Lys, 1153.4 Da), identified by LC-MS/MS showed the highest antioxidant activity. C. elegans fed with the selected peptide had longer lifespan, higher survival rate, superoxide dismutase (SOD) and catalase (CAT) activities than the control group (P<0.05), demonstrating the promising anti-aging effects of the antioxidant peptide from defatted round scad.

Journal of Functional Foods 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, Computed Properties 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

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

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

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

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

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