Category: thiazole

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

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

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

Du, Zhi published the artcileSelf-triggered click reaction in an Alzheimer’s disease model: in situ bifunctional drug synthesis catalyzed by neurotoxic copper accumulated in amyloid-beta plaques, Category: thiazole, the publication is Chemical Science (2019), 10(44), 10343-10350, database is CAplus and MEDLINE.

Cu is one of the essential elements for life. Its dyshomeostasis has been demonstrated to be closely related to neurodegenerative disorders, such as Alzheimer’s disease (AD), which is characterized by amyloid-beta (Abeta) aggregation and Cu accumulation. It is a great challenge as to how to take advantage of neurotoxic Cu to fight disease and make it helpful. Herein, we report that the accumulated Cu in Abeta plaques can effectively catalyze an azide-alkyne bioorthogonal cycloaddition reaction for fluorophore activation and drug synthesis in living cells, a transgenic AD model of Caenorhabditis elegans CL2006, and brain slices of triple transgenic AD mice. More importantly, the in situ synthesized bifunctional drug 6 can disassemble Abeta-Cu aggregates by extracting Cu and photo-oxygenating Abeta synergistically, suppressing Abeta-mediated paralysis and diminishing the locomotion defects of the AD model CL2006 strain. Our results demonstrate that taking the accumulated Cu ions in the Abeta plaque for an in situ click reaction can achieve both a self-triggered and self-regulated drug synthesis for AD therapy. To the best of our knowledge, a click reaction catalyzed by local Cu in a physiol. environment has not been reported. This work may open up a new avenue for in situ multifunctional drug synthesis by using endogenous neurotoxic metal ions for the treatment of neurodegenerative diseases.

Chemical Science 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, Category: thiazole.

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

Wang, Junren published the artcileEosin Y as a high-efficient photooxidase mimic for colorimetric detection of sodium azide, Category: thiazole, the publication is Analytical and Bioanalytical Chemistry (2020), 412(27), 7595-7602, database is CAplus and MEDLINE.

Abstract: The reported fluorescent dye-based artificial light-responsive oxidase mimics are suffering from their low catalytic efficiency. To overcome the limitation, we report the photooxidase-mimicking activity of Eosin Y which can catalyze the oxidation of various chromogenic substrates such as 3,3′,5,5′-tetramethylbenzydine (TMB), 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt (ABTS), 3,3′-diaminobenzidine (DAB), and o-phenylenediamine (OPD) by dissolved oxygen. The photooxidase-like activity of Eosin Y is highly efficient for TMB substrate, and its catalytic efficiency is higher than that of the reported fluorescein (130 fold) and 9-mesityl-10-methylacridinium ion (7.7-fold) mimetic photooxidase. Moreover, the photosensitized Eosin Y-TMB chromogenic system is utilized for colorimetric detection of highly toxic and explosive sodium azide (NaN₃) in a linear range from 5 to 500 μM with a limit of detection of 3.5 μM. The resulting colorimetric assay is selective and applied to determine NaN₃ in real lake water samples.

Analytical and Bioanalytical Chemistry 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 C40H35N7O8, Category: thiazole.

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

Jiang, Chen Hao published the artcileBioinformatics-based screening of key genes for transformation of liver cirrhosis to hepatocellular carcinoma, Computed Properties of 95-24-9, the publication is Journal of Translational Medicine (2020), 18(1), 40, database is CAplus and MEDLINE.

Abstract: Background: The aims of the present study were to identify key genes related to the transformation of cirrhosis into HCC, and explore the associated mol. mechanisms. Methods: GSE89377, GSE17548, GSE63898 and GSE54236 mRNA microarray datasets from Gene Expression Omnibus (GEO) were analyzed to obtain differentially expressed genes (DEGs) between HCC and liver cirrhosis tissues, and network anal. of protein-protein interactions (PPIs) was carried out. String and Cytoscape were used to analyze modules and identify hub genes, Kaplan-Meier Plotter and Oncomine databases were used to explore relationships between hub genes and disease occurrence, development and prognosis of HCC, and the mol. mechanism of the main hub gene was probed using Kyoto Encyclopedia of Genes and Genomes(KEGG) pathway anal. Results: In total, 58 DEGs were obtained, of which 12 and 46 were up- and down-regulated, resp. Three hub genes (CDKN3, CYP2C9 and LCAT) were identified and associated prognostic information was obtained. CDKN3 may be correlated with the occurrence, invasion, and recurrence of HCC. Genes closely related to changes in the CDKN3 hub gene were screened, and Kyoto Encyclopedia of Genes and Genomes (KEGGs) pathway anal. identified numerous cell cycle-related genes. Conclusion: CDKN3 may affect the transformation of liver cirrhosis into HCC, and represents a new candidate mol. marker of the occurrence and progression of HCC.

Journal of Translational 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 C7H5ClN2S, Computed Properties of 95-24-9.

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

Jamal Gilani, Sadaf published the artcileNovel benzothiazole hydrazine carboxamide hybrid scaffolds as potential in vitro GABA AT enzyme inhibitors: Synthesis, molecular docking and antiepileptic evaluation, Computed Properties of 95-24-9, the publication is Bioorganic & Medicinal Chemistry Letters (2019), 29(14), 1825-1830, database is CAplus and MEDLINE.

In the present study, a series of newer benzothiazole derivatives containing thiazolidin-4-one and azetidin-2-one, were synthesized by the cyclization of benzothiazolyl arylidene hydrazine carboxamide derivatives with thioglycolic acid and chloroacetyl chloride, resp. Results of in vivo anticonvulsant screening revealed that compounds I (R = 2,4-Cl₂, 4-NO₂) and II (R = 4-NO₂) have promising anticonvulsant activities without any neurotoxicity. Selected compounds were also evaluated for their in vitro GABA AT inhibition. The results indicated that compound I (R = 2,4-Cl₂, IC₅₀ 15.26 μM) exhibited excellent activity as compared to the standard drug vigabatrin (IC₅₀ 39.72 μM) suggesting the potential of these benzothiazole analogs as new anticonvulsant agents.

Bioorganic & Medicinal Chemistry 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 C7H5ClN2S, Computed Properties of 95-24-9.

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

Koperniku, Ana published the artcileThe Reaction of N -Trimethylsilyl-Substituted Heteroarylamines with Esters and Thioesters: An Efficient Protocol To Access Diheteroarylamides, Quality Control of 95-24-9, the publication is Synthesis (2019), 51(8), 1779-1790, database is CAplus.

The S-benzyl thioester and Me ester derivatives of a representative 4-pyridinone-based carboxylic acid were sufficiently activated to react efficiently in amide coupling reactions with the amide anion generated in situfrom the N-trimethylsilyl derivative of different weakly nucleophilic heteroarylamines. In acetonitrile as solvent, the precipitated diheteroarylamide products were isolated in pure form by vacuum filtration. This simple amide bond forming protocol can be readily adapted to the parallel synthesis of compound libraries.

Synthesis 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, Quality Control of 95-24-9.

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

Yanachkov, Ivan published the artcileSelf-neutralizing oligonucleotides with enhanced cellular uptake, Product Details of C5H7N3S3, the publication is Organic & Biomolecular Chemistry (2017), 15(6), 1363-1380, database is CAplus and MEDLINE.

There is tremendous potential for oligonucleotide (ON) therapeutics, but low cellular penetration due to their polyanionic nature is a major obstacle. We addressed this problem by developing a new approach for ON charge neutralization in which multiple branched charge-neutralizing sleeves (BCNSs) are attached to the internucleoside phosphates of ON by phosphotriester bonds. The BCNSs are terminated with pos. charged amino groups, and are optimized to form ion pairs with the neighboring phosphate groups. The new modified ONs can be prepared by standard automated phosphoramidite chem. in good yield and purity. They possess good solubility and hybridization properties, are not involved in non-standard intramol. aggregation, have low cytotoxicity, adequate chem. stability, improved serum stability, and above all, display significantly enhanced cellular uptake. Thus, the new ON derivatives exhibit properties that make them promising candidates for the development of novel therapeutics or research tools for modulation of the expression of target genes.

Organic & Biomolecular Chemistry published new progress about 1192027-04-5. 1192027-04-5 belongs to thiazole, auxiliary class Other Aliphatic Heterocyclic,Amine, name is N,N-Dimethyl-N’-(3-thioxo-3H-1,2,4-dithiazol-5-yl)formimidamide, and the molecular formula is C8H5IO, Product Details of C5H7N3S3.

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

Szponder, Tomasz published the artcileEffects of topical treatment of foot rot in sheep using ozonated olive ointment, Safety of Ammonium 2,2′-(hydrazine-1,2-diylidene)bis(3-ethyl-2,3-dihydrobenzo[d]thiazole-6-sulfonate), the publication is Journal of Veterinary Research (2021), 65(3), 369-374, database is CAplus and MEDLINE.

Foot rot in small ruminants is highly contagious, causes severe lameness, and impairs fertility and wool and meat production It is usually treated with parenteral antibiotics, with attendant antibiotic resistance risk, and with bactericidal footbaths, potentially harmful to humans and the environment. An alternative treatment in sheep is proposed based on repeated topical ozonated ointment application. Its effectiveness and safety were evaluated by estimation of acute-phase response, biochem. indicators of organic damage, and antioxidant/oxidant balance (AOB). The study was conducted on ten sheep with Egerton scale 2-3 lesions. Ozone application was repeated every day for seven days. Blood was drawn first (T0) after foot cleaning and before ozonation, then (T1) seven days after the first ozone application, and finally (T2) four days after the last application. High clin. effectiveness was observed, with total recovery by 28 days from the start of treatment. A significant increase in antiradical activity was noted on the basis of a 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) assay from 1.16 ± 0.04 μmolTe/mL at T0 to 1.23 ± 0.03 μmolTe/mL at T1, with a slight decrease in oxidative stress. Calculated on the basis of antiradical capacity, AOB was higher at T1 (130 ± 19%) and decreased to 110 ± 16% at T2. Calculated on the basis of reducing power, it was 169 ± 22% at T1 and 131 ± 17% at T2. These results indicated that the AOB is efficient enough to prevent oxidative organ injury and the applied doses of ozone are safe for animals.

Journal of Veterinary Research 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 C6H9N3O2S, 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