Category: thiazole

Taniguchi, Sayuri published the artcileInhibition of Heparin-induced Tau Filament Formation by Phenothiazines, Polyphenols, and Porphyrins, HPLC of Formula: 92-36-4, the publication is Journal of Biological Chemistry (2005), 280(9), 7614-7623, database is CAplus and MEDLINE.

Tau protein is the major component of the intraneuronal filamentous inclusions that constitute defining neuropathol. characteristics of Alzheimer’s disease and other tauopathies. The discovery of tau gene mutations in familial forms of frontotemporal dementia has established that dysfunction of the tau protein is sufficient to cause neurodegeneration and dementia. Here we have tested 42 compounds belonging to nine different chem. classes for their ability to inhibit heparin-induced assembly of tau into filaments in vitro. Several phenothiazines (methylene blue, azure A, azure B, and quinacrine mustard), polyphenols (myricetin, epicatechin 5-gallate, gossypetin, and 2,3,4,2′,4′-pentahydroxybenzophenone), and the porphyrin ferric deuteroporphyrin IX inhibited tau filament formation with IC₅₀ values in the low micromolar range as assessed by thioflavin S fluorescence, electron microscopy, and Sarkosyl insolubility Disassembly of tau filaments was observed in the presence of the porphyrin phthalocyanine. Compounds that inhibited tau filament assembly were also found to inhibit the formation of Aβ fibrils. Biochem. anal. revealed the formation of soluble oligomeric tau in the presence of the inhibitory compounds, suggesting that this may be the mechanism by which tau filament formation is inhibited. The compounds investigated did not affect the ability of tau to interact with microtubules. Identification of small mol. inhibitors of heparin-induced assembly of tau will form a starting point for the development of mechanism-based therapies for the tauopathies.

Journal of Biological 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 C14H10N2O, HPLC of Formula: 92-36-4.

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

Bort, Guillaume published the artcileStraightforward synthesis of PET tracer precursors used for the early diagnosis of Alzheimers disease through Suzuki-Miyaura cross-coupling reactions, SDS of cas: 92-36-4, the publication is Tetrahedron (2013), 69(35), 7345-7353, database is CAplus.

In positron emission tomog. [¹¹C]PIB, Pittsburgh Compound-B, is currently the most widely used radiopharmaceutical for the early diagnosis of Alzheimer’s disease. Synthetic routes for the preparation of the precursor of [¹¹C]PIB are reported in the literature. These strategies require multiple steps and the use of protecting groups. This paper describes a simple 1-step synthesis of the precursor of [¹¹C]PIB through a Suzuki-Miyaura coupling reaction using thermal conditions or microwave activation. These methods were successfully applied to the synthesis of various 2-arylbenzothiazole and 2-pyridinylbenzothiazole compounds including [¹⁸F] precursor derivatives of PIB containing a nitro function.

Tetrahedron 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, SDS of cas: 92-36-4.

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

Yamamoto, Yuzuru published the artcilePyridine derivatives containing sulfur. XXXI. Synthesis of pyridothiazoles and pyridoxazoles, Application In Synthesis of 31784-71-1, the publication is Yakugaku Zasshi (1951), 169-72, database is CAplus.

cf. C.A. 46, 112h. The following correction is made: 2-Amino-5-bromo- or 2-amino-5-iodopyridine and KCNS or Cu(CNS)₂ do not form a pyridothiazole ring as reported (cf. C.A. 46, 111c, 112ad). To 2-chloro-5-aminopyridine (I) (3 g.) and 9.1 g. KCNS in 47 mL. 95% AcOH at -5 to -10° is added 1.26 g. Br dropwise, the mixture filtered, and 3 volumes H₂O is added to the filtrate, which is again filtered and neutralized with Na₂CO₃ to give crude 2-amino-5-chloropyrido[3,2-d]thiazole (H) (C.A. numbering). Crude II recrystallized from MeOH gives 1.7 g. II, decompose 243-4°. 2-Hydroxy-5-aminopyridine and KCNS and Br in a similar way give the 5-HO analog (III) of II, m. 248-9°; acetate, needles, m. 286°. By using the 2-alkoxy analogs of I the following 5-alkoxy analogs of II are prepared similarly: MeO, needles or plates, m. 191-1.5°; EtO, needles or plates, m. 201-3°; iso-PrO, light yellow plates, m. 191-3°; BuO, plates, m. 139°; and iso-AmO, light orange needles, m. 126.5°. 2,5-Diaminopyridine and KCNS in 95% AcOH similarly give 2,5-diaminopyrido[3,2-d]-thiazole, m. 214-15°. 2,6-Diaminopyridine (3 g.) and 11 g. Cu(CNS)₂ in AcOH after removal of the AcOH, solution of the residue in hot water, and precipitation with Na₂CO₃ give 0.8 g. 2,5-diaminopyrido[2,3-d]thiazole, yellow prisms, m. 137°. Treating 2 g. 2-amino-3-nitro-5-bromopyridine (IV) with 2.8 g. PCl₅ 4 h. at 120-40°, decomposing the excess PCl₅ with ice water, filtering, and recrystallizing from MeOH give 1.4 g. 2-chloro-3-nitro-5-bromopyridine, yellow needles, m. 67-8°. Heating 1.5 g. IV in 6.5 mL. 85% HCl, adding 6.5 g. SnCl₂ at 100° during a period of 3 h., drying in vacuo, making alk. with NaOH, and taking up with ether gives 0.5 g. 2-hydroxy-3-amino-5-bromopyridine (V), m. 182-4°. Boiling 0.5 g. V in 3 mL. Ac₂O 40 min., filtering off the excess Ac₂O, cooling, making alk. with Na₂CO₃, and taking up with AcOEt gives 0.3 g. 6-bromo-2-methyloxazolo[5,4-b]-pyridine, needles, m. 223-5°.

Yakugaku Zasshi 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 C28H29NO4, Application In Synthesis of 31784-71-1.

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

Noman, Efaq published the artcileDecolourisation of dyes in greywater by mycoremediation and mycosorption process of fungi from peatland; primary study, Application In Synthesis of 30931-67-0, the publication is Materials Today: Proceedings (2020), 31(Part_1), 23-30, database is CAplus.

The current study investigated the potential of fungi from peatland for decolorizing dyes in the artificial greywater as a function of oxidative enzymes which included laccase (Lac), manganese peroxidase (MnP), lignin peroxidase (LiP). The fungal isolates were obtained from the peatland on potato dextrose agar (PDA) and purified using single spore technique. Remazol Brilliant Blue R (RBBR), Methylene blue (MB) and Congo red (CR) were used as models for detecting the applicability of the fungal enzyme to decolorizing the dyes. The screening of fungal isolates for the decolorisation of RBBR, MB and CR were investigated using plate assay and liquid-phase assays. The results revealed the fungal isolates varied in their ability to produce oxidative enzymes dependent on the production medium. However, the decolorisation of RBBR in the PD broth medium ranged from 17.96 to 44.89% after 7 days, while ranged from 55.98 to 99.99% in artificial greywater after 15 days of the incubation period. The fungal isolates exhibited also differences in the production of oxidative enzyme. The maximum production of Lac in artificial greywater was recorded by Cochliobolus sp. Number 403 while the highest production of MnP and LiP was noted by Trichoderma sp. Number 102, and Aspergillus sp. Number 506, resp. However, Aspergillus sp. Number 605 was used for further studies, because the fungus exhibited ability to produce Lac, MnP and LiP enzymes simultaneously. It can be concluded that the fungal isolates obtained from the peatland has a potential to decolorize the dyes in the artificial greywater.

Materials Today: Proceedings 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

Lin, Xuanfu published the artcileSynthesis and fungicidal activities of 2-benzylthio(sulfonyl)-5-methyl-7-substituted benzyloxy-1,2,4-triazolo[1,5-a] pyrimidine derivatives, Formula: C4H3Cl2NS, the publication is Youji Huaxue (2013), 33(2), 353-358, database is CAplus.

Using 2-benzylthio-5-methyl-7-hydroxyl-1,2,4-triazolo[1,5-a]pyrimidine as starting material, twelve novel 2-benzylthio-5-methyl-7-substituted benzyloxy-1,2,4-triazolo[1,5-a]pyrimidine derivatives and their sulfonyl analogs were synthesized through sequential reactions of etherification and oxidation, resp. Their structures were characterized by ¹H NMR, IR, MS and elemental anal. The preliminary bioassay indicated that some compounds exhibited certain fungicidal activities, for example, the inhibition rates of compounds 5c, 5k and 5l (50 μg/mL) against Botrytis cinerea were 61%, 69% and 85%, resp.

Youji Huaxue published new progress about 50398-77-1. 50398-77-1 belongs to thiazole, auxiliary class Thiazoles, name is 5-Chloro-2-(chloromethyl)-1,3-thiazole, and the molecular formula is C4H3Cl2NS, Formula: C4H3Cl2NS.

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

Xiang, Jiawei published the artcileSynthesis and biological evaluation of innovative thiourea derivatives as PHGDH inhibitors, Application of 4-(Naphthalen-1-yl)thiazol-2-amine, the publication is Chemical Papers (2020), 74(11), 3873-3886, database is CAplus.

Abstract: In order to discover novel compounds with inhibitory activity against 3-phosphoglycerate dehydrogenase (PHGDH), a series of thiourea derivatives were designed and synthesized based on the structural modification of compound 5d. Compound 5d emerged from the visual database of ChemDiv of 200,000 small mols. by docking score ranking. Inhibition experiments on PHGDH activity of newly synthesized compounds were performed in vitro. Compounds with more than 30% inhibitory rate at 25μM on PHGDH were screened for IC₅₀ measurement. Anti-proliferative activity of 4a, 5a, 6e, 6n against A2780, MDA-MB-468, MDA-MB-231 and HEK293T in vitro was evaluated. The results showed that the compound 4a displayed the best inhibitory activity on PHGDH among the newly synthesized compounds, and the compounds 4a, 5a, 6n had a better proliferation inhibition effect on human A2780 cell line than NCT-503 reported previously. In addition, 2D interaction diagrams revealed potential action modes of active compounds with PHGDH.

Chemical Papers 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 C40H35N7O8, Application of 4-(Naphthalen-1-yl)thiazol-2-amine.

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

Gao, Kai published the artcileNanoscale, automated, high throughput synthesis and screening for the accelerated discovery of protein modifiers, Recommanded Product: 6-Chlorobenzothiazol-2-ylamine, the publication is RSC Medicinal Chemistry (2021), 12(5), 809-818, database is CAplus and MEDLINE.

Hit finding in early drug discovery is often based on high throughput screening (HTS) of existing and historical compound libraries, which can limit chem. diversity, is time-consuming, very costly, and environmentally not sustainable. On-the-fly compound synthesis and in situ screening in a highly miniaturized and automated format has the potential to greatly reduce the medicinal chem. environmental footprint. Here, acoustic dispensing technol. has been used to synthesize a library in a 1536 well format based on the Groebke-Blackburn-Bienayme’ reaction (GBB-3CR) on a nanomole scale. The unpurified library was screened by differential scanning fluorimetry (DSF) and cross-validated using microscale thermophoresis (MST) against the oncogenic protein-protein interaction menin-MLL. Several GBB reaction products were found as μM menin binder, and the structural basis of the interactions with menin was elucidated by co-crystal structure anal. Miniaturization and automation of the organic synthesis and screening process can lead to an acceleration in the early drug discovery process, which is an alternative to classical HTS and a step towards the paradigm of continuous manufacturing

RSC Medicinal Chemistry 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, Recommanded Product: 6-Chlorobenzothiazol-2-ylamine.

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

Nath, Rajarshi published the artcileSynthesis and anticonvulsant evaluation of indoline derivatives of functionalized aryloxadiazole amine and benzothiazole acetamide, Quality Control of 95-24-9, the publication is Journal of Molecular Structure (2021), 129742, database is CAplus.

A series of I [R = H, 6-Cl, 5-O₂N, etc.] and II [R¹ = H, 4-MeO, 2-O₂N, 4-O₂N; R² = H, 5-Cl, 5-Br] were designed, synthesized and fulfilled structural requirement of pharmacophore and evaluated for anticonvulsant activities using maximal electroshock test (MES), s.c. pentylenetetrazole (scPTZ) seizures and neurotoxicity by motor impairment model in mice. The most active compound I [R = 6-Cl] showed significant anticonvulsant activity against both MES and scPTZ screens and emerged as most effective anticonvulsant compound with median dose of 35.7 mg/kg (MES ED₅₀), 88.15 mg/kg (scPTZ ED₅₀) and toxic dose (TD₅₀) was found to be > 500mg/kg. In-silico studies including mol. docking study were carried out to establish the mol. interaction of potent compound I [R = 6-Cl] in both Na⁺ channel and GABA_A receptors. The prediction of pharmacokinetic parameters and distance mapping of compounds were performed to establish the drug likeness property.

Journal of Molecular Structure 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

Dai, Wen published the artcileHighly Chemoselective and Enantioselective Catalytic Oxidation of Heteroaromatic Sulfides via High-Valent Manganese(IV)-Oxo Cation Radical Oxidizing Intermediates, HPLC of Formula: 5053-24-7, the publication is ACS Catalysis (2017), 7(7), 4890-4895, database is CAplus.

A manganese complex with a porphyrin-like ligand that catalyzes the highly chemoselective and enantioselective oxidation of heteroaromatic sulfides, including imidazole, benzimidazole, indole, pyridine, pyrimidine, pyrazine, sym-triazine, thiophene, thiazole, benzothiazole, and benzoxazole, with hydrogen peroxide is described, furnishing the corresponding sulfoxides in good to excellent yields and enantioselectivities (up to 90% yield and up to >99% ee) within a short reaction time (0.5 h). The practical utility of the method has been demonstrated in the gram-scale synthesis of chiral sulfoxide. Mechanistic studies, performed with ¹⁸O-labeled water (H₂¹⁸O), hydrogen peroxide (H₂¹⁸O₂), and cumyl hydroperoxide, reveal that a highvalent manganese-oxo species is generated as the oxygen atom delivering agent via carboxylic acid assisted heterolysis of O-O bonds. D. functional theory (DFT) calculations were also carried out to give further insight into the mechanism of manganese-catalyzed sulfoxidation On the basis of the theor. study, the coupled high-valent manganese(IV)-oxo cation radical species, which bears obvious similarities with that of reactive intermediates in the catalytic oxygenation reactions based on the cytochrome P 450 and metalloporphyrin models, has been proposed as the reactive oxidant in the non-heme manganese catalyst system.

ACS Catalysis 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, HPLC of Formula: 5053-24-7.

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

Behera, G. B. published the artcileQuaternization at an Sp² nitrogen. II. An analysis on the substituent effect and on the nature of the transition state, Safety of 4-(Naphthalen-1-yl)thiazol-2-amine, the publication is Bulletin of the Chemical Society of Japan (1979), 52(2), 604-7, database is CAplus.

The kinetics of N-phenacylation of a number of substituted thiazoles with substituted phenacyl bromides were investigated in PhNO₂ and in a number of other dipolar aprotic solvents. The rate constants of 2-amino-4-phenylthiazoles and 2-aminobenzothiazoles were calculated with suitably developed equations. The deviation of the observed values from the calculated results was ascribed to the steric effect. A 7-membered H-bonded transition state was proposed on the basis of the results obtained from the substituent and medium effects.

Bulletin of the Chemical Society of Japan 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, Safety of 4-(Naphthalen-1-yl)thiazol-2-amine.

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