Heterocyclic Building Blocks-Thiazole

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

Kumar, Nag S. published the artcileDesign and synthesis of an all-in-one 3-(1,1-difluoroprop-2-ynyl)-3H-diazirin-3-yl functional group for photo-affinity labeling, Product Details of C4H5NS2, the publication is Bioorganic & Medicinal Chemistry (2009), 17(15), 5388-5395, database is CAplus and MEDLINE.

A novel radioisotope-free photo-affinity probe containing the 3-(1,1-difluoroprop-2-ynyl)-3H-diazirin-3-yl functional group was designed and synthesized. This very compact functionality is envisaged to allow photochem.-induced coupling of a compound to its target followed by click reaction coupling with an azido-biotin reagent in order to facilitate purification of the labeled target. In a proof-of-concept study we have shown that 3-(1,1-difluoroprop-2-ynyl)-3H-diazirin-3-yl functional group could be photolyzed to efficiently furnish its methanol adduct and that the generated highly unstable carbene does not react with the neighboring acetylene moiety. A subsequent click reaction with biotin N-(2-azidoethyl) amide proceeded smoothly to give a triazole regioselectively. This chem. probe should thus be of unique value for facilitating identification of the mol. structure of the target of a bioactive compound

Bioorganic & Medicinal Chemistry 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, Product Details of C4H5NS2.

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

Zheng, Ming-Qiang published the artcileSynthesis of 2-(4-aminophenyl)benzothiazole derivatives and determination of their activity as PET tracers for human brain β-amyloid peptides, Computed Properties of 92-36-4, the publication is Youji Huaxue (2007), 27(11), 1369-1373, database is CAplus.

A series of novel 2-(4-aminophenyl)-6-substituted benzothiazole derivatives were prepared and evaluated as potential β-amyloid PET (positron emission tomog.) tracers. Were prepared from proper 2-amino-6-substituted benzothiazole derivatives through basic hydrolysis, intermol. cycloaddition and N/O-alkylation reactions. Their structures were confirmed by IR, ¹H NMR, EI/ESI-MS, HRMS spectra and elemental anal. The sequence of binding affinity of some compounds with human brain homogenate was analyzed.

Youji Huaxue 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 C7H4ClIO2, Computed Properties of 92-36-4.

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

Ma, Youchuan published the artcileEffect of ultrasound on mass transfer kinetics and phenolic compounds of apple cubes during osmotic dehydration, COA of Formula: C18H24N6O6S4, the publication is LWT–Food Science and Technology (2021), 112186, database is CAplus.

This study investigated the impacts of ultrasound-assisted osmotic dehydration (UOD) with different frequency (40 kHz, 80 kHz, 40 + 80 kHz) and intensity (25 W/L, 50 W/L, 75 W/L) on the kinetics of mass transfer, phenolic losses and the antioxidant properties of apple cubes (8 mm). The mass transfer efficiency of solid gain (SG) was greater under dual-frequency (β = 0.413) than 40 kHz (β = 0.707) and 80 kHz (β = 0.793) under the same intensity. Moreover, the mass transfer efficiency of SG under 75 W/L 40 kHz UOD was higher than that of 25 W/L and 50 W/L UOD based on β values. Notably, the loss of phenolic content under 75 W/L UOD (18.9%) was substantially higher than that of the 25 W/L UOD treatment (1.2-1.8%). A UOD treatment of 50 W/L and 40 + 80 kHz is recommended to optimize mass transfer efficiency and phenolic retention of dehydrated apple cubes.

LWT–Food Science and 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 C18H24N6O6S4, COA of Formula: C18H24N6O6S4.

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

Cai, Mingzhong published the artcileRecyclable copper-catalyzed cyclization of o-haloanilides and metal sulfides: An efficient and practical access to substituted benzothiazoles, Name: 2-(4-Aminophenyl)-6-methylbenzothiazole, the publication is Molecular Catalysis (2022), 112115, database is CAplus.

An efficient heterogeneous copper-catalyzed cyclization of o-haloanilides and metal sulfides has been achieved via the C-S coupling in DMF at 80 or 140° in the existence of an MCM-41-bound NHC-Cu(I) catalyst and then intramol. condensation, delivering a wide range of substituted benzothiazoles in mostly good to high yields. This new MCM-41-NHC-CuI complex can facilely be obtained by a two-step procedure starting from easily accessible and inexpensive reagents and reused more than seven times without any significant loss of its catalytic efficiency. The present protocol has been successfully applied to the gram-scale synthesis of two antitumor agents 5F203 and PMX 610.

Molecular Catalysis 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, Name: 2-(4-Aminophenyl)-6-methylbenzothiazole.

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

Liu, Jian published the artcileAmphipathic Side Chain of a Conjugated Polymer Optimizes Dopant Location toward Efficient N-Type Organic Thermoelectrics, Category: thiazole, the publication is Advanced Materials (Weinheim, Germany) (2021), 33(4), 2006694, database is CAplus and MEDLINE.

There is no mol. strategy for selectively increasing the Seebeck coefficient without reducing the elec. conductivity for organic thermoelecs. Here, it is reported that the use of amphipathic side chains in an n-type donor-acceptor copolymer can selectively increase the Seebeck coefficient and thus increase the power factor by a factor of ≈5. The amphipathic side chain contains an alkyl chain segment as a spacer between the polymer backbone and an ethylene glycol type chain segment. The use of this alkyl spacer does not only reduce the energetic disorder in the conjugated polymer film but can also properly control the dopant sites away from the backbone, which minimizes the adverse influence of counterions. As confirmed by kinetic Monte Carlo simulations with the host-dopant distance as the only variable, a reduced Coulombic interaction resulting from a larger host-dopant distance contributes to a higher Seebeck coefficient for a given elec. conductivity Finally, an optimized power factor of 18 μW m^-1 K^-2 is achieved in the doped polymer film. This work provides a facile mol. strategy for selectively improving the Seebeck coefficient and opens up a new route for optimizing the dopant location toward realizing better n-type polymeric thermoelecs.

Advanced Materials (Weinheim, Germany) published new progress about 2215018-37-2. 2215018-37-2 belongs to thiazole, auxiliary class Thiazoles, name is 4,4′-Bis(octyloxy)-2,2′-bis(trimethylstannyl)-5,5′-bithiazole, and the molecular formula is C28H52N2O2S2Sn2, Category: thiazole.

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

Praveen, Aletti S. published the artcileSynthesis, characterization and antimicrobial studies of a few novel thiazole derivatives, Quality Control of 64987-16-2, the publication is Medicinal Chemistry Research (2014), 23(1), 259-268, database is CAplus.

A series of novel N-[4-(substituted)-1,3-thiazol-2-yl]-2-(substituted)acetamides and Me 2-(2-(2-(substituted)acetamido)thiazol-4-yl)acetates were synthesized. All compounds were screened for their in vitro antibacterial activity against S. aureus, E. coli, P. aeruginosa, and K. pneumonia by disk diffusion and for antifungal activity against P. marneffei, T. mentagrophytes, A. flavus, and A. fumigatus by serial plate dilution Some of the compounds exhibited growth inhibition against all the tested bacterial strains, with MIC of 12.5-6.25 μg/mL. Among the compounds tested for antifungal activity, several of them showed a wide range of activity against all the tested strains. Most of the newly synthesized compounds were effective against fungal strains rather than bacterial strains. However, some of the compounds showed selective sensitivity against some of the bacterial strains, whereas they were unable to sustain the growth of other strains.

Medicinal Chemistry Research published new progress about 64987-16-2. 64987-16-2 belongs to thiazole, auxiliary class Thiazole,Amine,Ester, name is Methyl 2-(2-aminothiazol-4-yl)acetate, and the molecular formula is C6H8N2O2S, Quality Control of 64987-16-2.

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

Wu, Feng published the artcileSynthesis and evaluation of novel 2,4-diaminopyrimidines bearing a sulfoxide moiety as anaplastic lymphoma kinase (ALK) inhibition agents, Product Details of C7H5ClN2S, the publication is Bioorganic & Medicinal Chemistry Letters (2021), 128253, database is CAplus and MEDLINE.

Herein, 16 new 2,4-diaminopyrimidines I (R¹ = H, F, Cl; R² = EtS, EtSO, i-PrSO; R³ = Me₂NCH₂CH₂NMe, 4-methylpiperazin-1-yl, 4-methyl-1,4-diazepan-1-yl, 4-dimethylaminopiperidin-1-yl, etc.; R⁴ = H, H₂N, EtCONH) bearing a sulfide or sulfoxide moiety were synthesized and evaluated for anaplastic lymphoma kinase (ALK) inhibitory activity. The optimal compound I [R¹ = F; R² = EtSO; R³ = 4-methylpiperazin-1-yl; R⁴ = EtCONH; (II)] exhibited excellent antiproliferative activity against non-small cell lung cancer NCI-H2228 cells, which was better than that of Brigatinib and similar to Ceritinib. Mechanism study revealed that the compound II decreased the mitochondrial membrane potential and arrested NCI-H2228 cells in the G0/G1 phase, finally resulting in cellular apoptosis. It is interesting that the compound II could effectively inhibit the migration of NCI-H2228 cells and may be a promising leading compound for chemotherapy of metastatic cancer.

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 C11H8N2O2, Product Details of C7H5ClN2S.

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

Jeon, Yoon T. published the artcileIdentification of 1-{2-[4-chloro-1′-(2,2-dimethylpropyl)-7-hydroxy-1,2-dihydrospiro[indole-3,4′-piperidine]-1-yl]phenyl}-3-{5-chloro-[1,3]thiazolo[5,4-b]pyridin-2-yl}urea, a potent, efficacious and orally bioavailable P2Y₁ antagonist as an antiplatelet agent, Synthetic Route of 31784-71-1, the publication is Bioorganic & Medicinal Chemistry Letters (2014), 24(5), 1294-1298, database is CAplus and MEDLINE.

Spiropiperidine indoline-substituted diaryl ureas had been identified as antagonists of the P2Y₁ receptor. Enhancements in potency were realized through the introduction of a 7-hydroxyl substitution on the spiropiperidinylindoline chemotype. SAR studies were conducted to improve PK and potency, resulting in the identification of compound 3e, a potent, orally bioavailable P2Y₁ antagonist with a suitable PK profile in preclin. species. Compound 3e demonstrated a robust antithrombotic effect in vivo and improved bleeding risk profile compared to the P2Y₁₂ antagonist clopidogrel in rat efficacy/bleeding models.

Bioorganic & Medicinal Chemistry Letters 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, Synthetic Route of 31784-71-1.

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

Liu, Shuo published the artcileProgrammable and Reversible Regulation of Catalytic Hemin@MOFs Activities with DNA Structures, Computed Properties of 30931-67-0, the publication is Chemical Research in Chinese Universities (2020), 36(2), 301-306, database is CAplus.

Abstract: Metal-organic frameworks(MOFs)-based nanozyme plays an important role in biosensing, therapy and catalysis. In this study, the effects of single-stranded DNA(ssDNA) with programmable sequences and its complementary DNA(TDNA) on the intrinsic peroxidase-like activity of hemin loaded MOFs(UiO-66-₂), denoted as hemin@UiO-66-NH₂, were investigated. The hemin@UiO-66-₂ exhibited improved catalytic activity compared with free hemin. However, the catalytic activity is inhibited in the presence of ssDNA, as ssDNA can be adsorbed by MOFs and therefore protected the active sites from contact with substrates. Upon the addition of the T_DNA, double-stranded DNA(dsDNA) was formed and detached from the MOFs, resulting in the recovery of catalytic activity. Sequentially adding ssDNA or its complementary DNA strands can achieve the reversible regulation of the catalytic activity of MOFs nanozymes. Moreover, the DNA hybridization-based regulation was further applied to a cascaded catalytic system composed of the nanozyme, hemin@UiO-66-NH₂, and glucose oxidase. These nanozyme based programmable and reversibly regulated catalytic systems may have potential applications in future smart biosensing and catalysis systems.

Chemical Research in Chinese Universities 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