Heterocyclic Building Blocks-Thiazole

Henglein, A. published the artcileDependence of the intensity of fluorescence on the quencher concentration in micellar systems, COA of Formula: C14H12N2S, the publication is Berichte der Bunsen-Gesellschaft (1978), 82(10), 1107-12, database is CAplus.

The quenching of the fluorescence of 2-(4-aminophenyl)-3-methylbenzothiazol solubilized in micelles of sodium dodecylsulfate by duroquinone was investigated. The decay constant k₀ in the absence of quencher is 6.9 × 10⁸ s^-1. At constant concentrations of the fluorescing and the quenching compounds the fluorescence intensity decreases with decreasing surfactant concentration This effect is explained by the changes in the distribution of the emitting and quenching mols. among the micelles. A relationship is given which takes into account the statistical distribution of solubilized mols. The 1st order rate constant is k_m = m·k₁ for quenching in a micelle carrying m mols. of the quencher, k₁, the rate constant for quenching in a micelle containing 1 mol. of the quencher, was 3.5 × 10⁸ s^-1. The ion pair formation in micelles containing 2-(4-aminophenyl)-3-methylbenzothiazol and duroquinone, the biphotonic ionization of 2-(4-aminophenyl)-3-methylbenzothiazol in anionic micelles and in MeOH solution, and the formation of the triplet state of this compound in toluene and in acid aqueous solutions were studied by laser flash photolysis.

Berichte der Bunsen-Gesellschaft 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, COA of Formula: C14H12N2S.

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

Barni, Ermanno published the artcileMonoazo dyes for polyamide derived from 4-alkylamido-2-hydroxybenzoic acids, Quality Control of 92-36-4, the publication is Dyes and Pigments (1984), 5(1), 15-36, database is CAplus.

Data on a series of 65 azo disperse dyes I (R = C₁-C₁₅ alkyl; A mono- or disubstituted or unsubstituted) are reported. The dyes are suitable for application to polyamide fibers and produce yellow to red-orange shades. Many correlations between the nature of substituents and the phys., spectroscopic or tinctorial properties of the dyes were established. Correlations between structure and color of dyed fabrics were also found.

Dyes and Pigments 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, Quality Control of 92-36-4.

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

Wang, Xueqing published the artcileSynthesis and Evaluation of Benzothiazole-Based Analogues as Novel, Potent, and Selective Fatty Acid Amide Hydrolase Inhibitors, Quality Control of 92-36-4, the publication is Journal of Medicinal Chemistry (2009), 52(1), 170-180, database is CAplus and MEDLINE.

High-throughput screening (HTS) identified benzothiazole analog (I) as a potent fatty acid amide hydrolase (FAAH) inhibitor. Structure-activity relationship (SAR) studies indicated that the sulfonyl group, the piperidine ring and benzothiazole were the key components to their activity, with II being the most potent analog in this series. Time-dependent preincubation study of compound I was consistent with it being a reversible inhibitor. Activity-based protein-profiling (ABPP) evaluation of I in rat tissues revealed that it had exceptional selectivity and no off-target activity with respect to other serine hydrolases. Mol. shape overlay of I with a known FAAH inhibitor indicated that these compounds might act as transition-state analogs, forming putative hydrogen bonds with catalytic residues and mimicking the charge distribution of the tetrahedral transition state. The modeling study also indicated that hydrophobic interactions of the benzothiazole ring with the enzyme contributed to its extraordinary potency. These compounds may provide useful tools for the study of FAAH and the endocannabinoid system.

Journal of Medicinal Chemistry 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 C4H6O3, Quality Control of 92-36-4.

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

Lesnichaya, M. V. published the artcileSynthesis of selenium-containing galactomannan-stabilized nanocomposites with particle size-sensitive antiradical activity, Safety of Ammonium 2,2′-(hydrazine-1,2-diylidene)bis(3-ethyl-2,3-dihydrobenzo[d]thiazole-6-sulfonate), the publication is Russian Chemical Bulletin (2020), 69(10), 1979-1986, database is CAplus.

Water-soluble hybrid nanocomposites were synthesized for the first time with the use of industrial crystalline selenium (gray powder selenium) activated in a hydrazine hydrate-alkali base-recovery system. The obtained nanocomposites consist of the selenium nanoparticles 13.0-24.0 nm in size stabilized by biocompatible natural polysaccharide galactomannan. The structures of the nanocomposites were characterized by a complex of physicochem. methods (X-ray diffraction anal., transmission electron microscopy, and IR spectroscopy). The pronounced antioxidant activity of the prepared nanocomposites against free radicals of 2,2-diphenyl-1-picrylhydrazyl and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt was found, and its value correlates with the particle size of selenium.

Russian Chemical Bulletin 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, Safety of Ammonium 2,2′-(hydrazine-1,2-diylidene)bis(3-ethyl-2,3-dihydrobenzo[d]thiazole-6-sulfonate).

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

Marquez, Augusto published the artcileNanoporous silk films with capillary action and size-exclusion capacity for sensitive glucose determination in whole blood, Recommanded Product: Ammonium 2,2′-(hydrazine-1,2-diylidene)bis(3-ethyl-2,3-dihydrobenzo[d]thiazole-6-sulfonate), the publication is Lab on a Chip (2021), 21(3), 608-615, database is CAplus and MEDLINE.

In optical biosensing, silk fibroin (SF) appears as a promising alternative where other materials, such as paper, find limitations. Besides its excellent optical properties and unmet capacity to stabilize biomacromols., SF in test strips exhibits addnl. functions, i.e. capillary pumping activity of 1.5 mm s^-1, capacity to filter blood cells thanks to its small, but tuneable, porosity and enhanced biosensing sensitivity. The bulk functionalization of SF with the enzymes glucose oxidase and peroxidase and the mediator ABTS produces colorless and transparent SF films that respond to blood glucose increasing 2.5 times the sensitivity of conventional ABTS-based assays. This enhanced sensitivity results from the formation of SF-ABTS complexes, where SF becomes part of the bioassay. Addnl., SF films triple the durability of most stable cellulose-based sensors. Although demonstrated for glucose, SF microfluidic test strips may incorporate other optical bioassays, e.g. immunoassays, with the aim of transferring them from central laboratories to the place of patient’s care.

Lab on a Chip 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, Recommanded Product: Ammonium 2,2′-(hydrazine-1,2-diylidene)bis(3-ethyl-2,3-dihydrobenzo[d]thiazole-6-sulfonate).

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

Stoffel, Fernanda published the artcileProduction of edible mycoprotein using agroindustrial wastes: Influence on nutritional, chemical and biological properties, COA of Formula: C18H24N6O6S4, the publication is Innovative Food Science & Emerging Technologies (2019), 102227, database is CAplus.

The production of Agaricus blazei, Auricularia fuscosuccinea and Pleurotus albidus mycoproteins in brewer-spent grain and grape bagasse by solid-state cultivation was studied, including an investigation of their nutritional value and biol. activity. The production of P. albidus mycoprotein in brewer-spent grain resulted in the highest values of protein (22.6 g.100 g^-1), total amino acids (78.54 mg.g^-1), ergosterol (0.39 ± 0.01 mg.g^-1) and mycelial biomass (125.60 ± 3.30 mg.g^-1). The A. fuscosuccinea mycoprotein in brewer-spent grain resulted in the highest value of total phenolics (3.80 mg EAG/g) and higher antioxidant activity. Using grape bagasse, the P. albidus mycoprotein increased 23.9% proteins, reduced 15.5% and 77% total fats and phenolics, resp. Anti-hyperglycemic activity, assessed by α-glycosidase inhibition in vitro, was observed in the P. albidus and A. blazei mycoproteins produced in brewer-spent grain (inhibition of α-glycosidase >98%). Mycoproteins produced in brewer-spent grain and grape bagasse could be a strategy to increase the nutritional value and biol. activity of these agroindustrial residues.

Innovative Food Science & Emerging Technologies 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 C12H14BNO2, COA of Formula: C18H24N6O6S4.

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

Ueda, Kanichi published the artcilePyridine derivatives containing sulfur. L. Mechanism of cleavage of thiazole ring of 2-aminothiazolo[5,4-b]pyridines by means of aqueous alkali, Application In Synthesis of 31784-71-1, the publication is Pharmaceutical Bulletin (1956), 396-401, database is CAplus and MEDLINE.

cf. C.A. 51, 2741i. Determination of the structures of the previously reported (C.A. 48, 5187h) “Substances I (I), II (II), and III (III),” prepared from 6-Cl (IV) and 6-EtO (V) derivatives of 3-amino-2-mercaptopyridine should help clarify the mechanism of the cleavage of the thiazole ring of the title compounds Comparisons of the infrared and ultraviolet absorption spectra of I with those of the 3-amino (VI) and 3-acetamido (VII) derivatives of 6,2-Cl(MeS)C₅H₂N (VIII) led to the conclusion that I was 6,2,3-Cl(MeS)(H₂NCONH)C₅H₂N. This conclusion was supported by heating 0.6 g. I 6 hrs. on a H₂O bath with 40 cc. Ac₂O and evaporating in vacuo to give 0.08 g. 3-AcNHCONH derivative of VIII, m. 209°, and 0.3 g. VII, m. 166° (from the mother liquor chromatographed in CHCl₃ over Al₂O₃). Support also came from the synthesis of I:1.2 g. IV in 170 cc. AcOH treated slowly with 2.5 g. KNCO in 20 cc. H₂O at 40°, stirred 3 hrs., diluted with much H₂O, and kept overnight yielded 0.82 g. 6,2,3-Cl(HS)(H₂NCONH)C₅H₂N (IX), m. 185-90° (effervescence); this gave I, m. 286-95°, methylated with MeI in alk. solution Also, 0.8 g. VI similarly treated with KNCO yielded 0.8 g. I. Likewise treated with KNCO, 2-MeS (X) and 2-EtS derivatives of 3,6-H₂N(EtO)C₅H₃N gave II, m. 200-36°, and III, m. 160-1°, resp.; their ultraviolet spectra confirmed their structures as 6,2,3-EtO(MeS)(H₂NCONH)C₅H₂N and 6,2,3-EtO(EtS)(H₂NCONH)C₅H₂N, resp. The mechanism of cleavage of the thiazole ring in the 5-Cl (XI) and 5-EtO (XII) derivatives of the title compound was studied. XI (0.7 g.) was refluxed 1 hr. in an oil bath at 120-30° with 6 cc. 10% NaOH while NH₃ evolved, the solution neutralized with AcOH, the resulting precipitate methylated with Me₂SO₄, the ether extract of the product evaporated, and the residue fractionally crystallized to give 0.21 g. VI, m. 56° (from petr. ether-ether), and 0.22 g. I, m. 290° (from MeOH). However, refluxing 7 hrs. instead of 1 hr. gave only VI. IX (0.7 g.) similarly hydrolyzed for 1 hr. and methylated yielded 0.15 g. VI and 0.12 g. I, but after 6 hrs. hydrolysis it gave only VI. XII (1 g.) refluxed 6.5 hrs. with 10 cc. 20% NaOH in the presence of 0.2 g. As₂O₃ while NH₃ evolved, the mixture cooled, filtered, and the filtrate neutralized with AcOH yielded 0.7 g. V, m. 150-70° (characterized by methylation to X and acetylation to 3,6,2-AcNH(EtO)(MeS)C₅H₂N, m. 124°), and after standing overnight, 0.1 g. 6,2,3-EtO(HS)(H₂NCONH)C₅H₂N, m. 195-8° (decomposition)(characterized by methylation with Me₂SO₄ to II). Longer hydrolysis (10 hrs.) of XII gave only V. Confirmation of the production of V from XII was obtained by condensing it (0.5 g.) in 1 cc. H₂O and 5 cc. EtOH containing 0.2 g. NaOH with 0.6 g. BzCH₂Br to yield, after standing overnight at room temperature, the expected 6-ethoxy-2-phenylpyrido[2,3-b]1,4-thiazine(0.42 g.), m. 125° (C.A. 50, 10101g). These results of hydrolysis of IX, XI, and XII led to the conclusion that amino-thiazolopyridines were converted to mercaptopyridines through mercaptopyridylureas as intermediates, which were somewhat resistant to the hydrolysis.

Pharmaceutical Bulletin 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 C11H10ClNO, Application In Synthesis of 31784-71-1.

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

Sekar, N. published the artcileThiazole – containing monoazo direct dyes, Formula: C14H12N2S, the publication is Colourage (2005), 52(3), 95-98, database is CAplus.

A review. Chem. of monoazo direct dyes based on dehydrothio-p-toluidine and its higher analogs and the others containing thiazolyl residue is discussed in the light of structures documented in color index.

Colourage 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 C8H5F3O2S, Formula: C14H12N2S.

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

Riesz, E. published the artcileSome new benzothiazole derivatives and comparison dyeing with such compounds, Safety of 2-(4-Aminophenyl)-6-methylbenzothiazole, the publication is Textilveredlung (1991), 26(12), 403-5, database is CAplus.

The yellow dye primuline, prepared by heating p-toluidine with S, was separated into 3 bases, having the structure I (x = 0, 1, or 2), which were then converted into the corresponding Na sulfonate salts and used to dye viscose and cotton fabrics. For the I (x = 0) Na sulfonate, the fibers remained practically undyed, displaying only a light yellow tinge; with the sulfonates of I (x = 2) and I (x = 3) yellow and deep yellow dyeings were produced, resp. To evaluate the shade-deepening and affinity effects of the benzothiazole (II) groups, the 3 Na sulfonates were diazotized and coupled with β-naphthol on the fibers. Most of the dye was taken up by the fibers because of an increase in affinity, but a certain contribution by the shade-deepening effect of the II groups could not be excluded. Reaction of the 3 sulfonates with p-dimethylaminobenzaldehyde produced dyes containing a weaker chromophore, i.e., azomethine, than the azo group. These compounds dyed cellulosic fibers widely different shades of yellow and orange and, as free bases, gave basic dyes which dyed fibers from an HOAc solution without pretreatment. Conversion of the amino groups of the 3 bases into SH groups yielded the 1st purely synthetic S dyes for dyeing cellulosic fibers yellow shades.

Textilveredlung 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, Safety of 2-(4-Aminophenyl)-6-methylbenzothiazole.

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

Okamiya, Jiro published the artcile2-Amino-4(or 5)-arylthiazoles. II. Ultraviolet absorption spectra of α-naphthyl, biphenyl, and hydroxyaryl substituted compounds, Application In Synthesis of 56503-96-9, the publication is Nippon Kagaku Zasshi (1959), 903-6, database is CAplus.

cf. CA 55, 4486c. Ultraviolet absorption spectra of 2-amino-4(α-naphthyl)thiazole, m. 162°, 2-amino-4-(α-naphthyl)-5-methylthiazole, m. 195°, 2-amino-5-(α-naphthyl)thiazole, m. 129°, 2-amino-4-methyl-5-(α-naphthyl)thiazole, m. 163°, 2-amino-4-(α-naphthyl)-5-phenylthiazole, m. 223°, 2-amino-4-phenyl-5-(α-naphthyl)thiazole, m. 248°, 2-amino-4,5-bis(α-naphthyl)thiazole, m. 260° (decomposition), 2-amino-4-biphenylylthiazole, 2-amino-4-biphenylyl-5-phenylthiazole, m. 201°, 2-amino-4-(p-hydroxyphenyl)thiazole, m. 212°, 2-amino-4-(p-hydroxyphenyl)-5-methylthiazole-HCl, HCl, 208-10°, 2-amino-4-(o-hydroxyphenyl)thiazole, 2-amino-4-(o-hydroxyphenyl)-5-methylthiazole, m. 120°, 2-amino-4-(p-hydroxyphenyl)-5-phenylthiazole, m. 284°, 2-amino-4-(o-hydroxyphenyl)-5-phenylthiazole, m. 171°, and 2-amino-4-(2-hydroxy-1-naphthyl)thiazole, m. 198°, were reported. The naphthyl group, due to its steric hindrance, exerted less effect on spectra, but was bathochromic at 5 position when compared with that at 4 position. The o-hydroxyphenyl group gave a red shift to the maximum at shorter wave length in spite of its expected steric effects. This must be attributed to the existence of chelation. Intermediate ketones of above thiazoles were prepared α-Bromonaphthalene (27.6 g.) was converted to Grignard reagent, 1.33 g. CdCl₂ added, the solvent replaced by C₆H₆, and 8.3 g. AcCl added to give 11 g. α-acetonaphthone. Similarly, α-propionaphthone, α-naphthyl benzyl ketone, ω-(α-naphthyl)acetophenone and ω-(α-naphthyl)acetonaphthone were prepared in 55, 60, 59 and 36% yields, resp. Naphthalene (100 g.), 250 cc. CS₂, and 130 g. AlCl₃ treated with ethylene oxide from 70 cc. ClCH₂CH₂OH gave 29 g. α-naphthylethanol which was oxidized with CrO₃ in AcOH to α-naphthylacetaldehyde. EtOMgCH(CO₂Et)₂ prepared from 9 g. CH₂(CO₂Et)₂, 1.3 g. Mg, and 7 cc. EtOH was treated with α-naphthylacetyl chloride prepared from 9.5 g. α-naphthylacetic acid and SOCl₂, and the product hydrolyzed to give 5 g. α-naphthylacetone.

Nippon Kagaku Zasshi published new progress about 56503-96-9. 56503-96-9 belongs to thiazole, auxiliary class Thiazole,Amine,Naphthalene, name is 4-(Naphthalen-1-yl)thiazol-2-amine, and the molecular formula is C13H10N2S, Application In Synthesis of 56503-96-9.

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