Category: thiazole

Prangkio, Panchika published the artcileSelf-assembled, cation-selective ion channels from an oligo(ethylene glycol) derivative of benzothiazole aniline, Name: 2-(4-Aminophenyl)-6-methylbenzothiazole, the publication is Biochimica et Biophysica Acta, Biomembranes (2011), 1808(12), 2877-2885, database is CAplus and MEDLINE.

This paper describes the spontaneous formation of well-defined pores in planar lipid bilayers from the self-assembly of a small synthetic mol. that contains a benzothiazole aniline (BTA) group attached to a tetra-ethylene glycol (EG₄) moiety. Macroscopic and single-channel current recordings suggest that these pores are formed by the assembly of four BTA-EG₄ monomers with an open pore diameter that appears similar to the one of gramicidin pores (∼0.4 nm). The single-channel conductance of these pores is modulated by the pH of the electrolyte and has a min. at pH ∼3. Self-assembled pores from BTA-EG₄ are selective for monovalent cations and have long open channel lifetimes on the order of seconds. BTA-EG₄ monomers in these pores appear to be arranged sym. across both leaflets of the bilayer, and spectroscopy studies suggest that the fluorescent BTA group is localized inside the lipid bilayers. In terms of biol. activity, BTA-EG₄ mols. inhibited growth of gram-pos. Bacillus subtilis bacteria (IC₅₀ ∼50 μM) and human neuroblastoma SH-SY5Y cells (IC₅₀ ∼60 μM), while they were not toxic to gram-neg. Escherichia coli bacteria at a concentration up to 500 μM. Based on these properties, this drug-like, synthetic, pore-forming mol. with a mol. weight below 500 g mol^-1 might be appealing as a starting material for development of antibiotics or membrane-permeating moieties for drug delivery. From a biophys. point of view, long-lived, well-defined ion-selective pores from BTA-EG₄ mols. offer an example of a self-assembled synthetic supramol. with biol. function.

Biochimica et Biophysica Acta, Biomembranes 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

Tikhonova, Tatyana A. published the artcileDevelopment of 1,3-thiazole analogues of imidazopyridines as potent positive allosteric modulators of GABA_A receptors, Recommanded Product: 6-Chlorobenzothiazol-2-ylamine, the publication is Bioorganic Chemistry (2020), 103334, database is CAplus and MEDLINE.

Structure-activity relationship studies were conducted in the search for 1,3-thiazole isosteric analogs of imidazopyridine drugs (Zolpidem, Alpidem). Three series of novel γ-aminobutyric acid receptor (GABA_AR) ligands belonging to imidazo[2,1-b]thiazoles I [R¹ = OMe, NMe₂, OEt; R² = p-chlorophenyl], [R¹ = OMe, R² = p-nitrophenyl] and [R¹ = OEt, R² = o,p-dichlorophenyl], imidazo[2,1-b][1,3,4]thiadiazoles II [R³ = OEt, NMe₂, NPr₂; R⁴ = p-chlorophenyl; R⁵ = Et, iso-Pr, MOM] and benzo[d]imidazo[2,1-b]thiazoles III [R⁶ = NH₂, OEt, NMe₂, NEt₂, NPr₂; R⁷ = Ph, p-fluorophenyl o,p-dimethoxyphenyl, etc.; R⁸ = H, Cl, OMe] were synthesized and characterized as active agents against GABA_AR benzodiazepine-binding site. In each of these series, potent compounds were discovered using a radioligand competition binding assay. The functional properties of highest-affinity compounds III [R⁶ = NH₂, R⁷ = p-chlorophenyl, R⁸ = H] and [R⁶ = NMe₂, R⁷ = o-chlorophenyl, R⁸ = H] as GABA_AR pos. allosteric modulators (PAMs) were determined by electrophysiol. measurements. In-vivo studies on zebrafish demonstrated their potential for the further development of anxiolytics. Using the OECD “Fish, Acute Toxicity Test” active compounds were found safe and non-toxic. Structural bases for activity of benzo[d]imidazo[2,1-b]thiazoles were proposed using mol. docking studies. The isosteric replacement of the pyridine nuclei by 1,3-thiazole, 1,3,4-thiadiazole, or 1,3-benzothiazole in the ring-fused imidazole class of GABA_AR PAMs was showed to be promising for the development of novel hypnotics, anxiolytics, anticonvulsants and sedatives drug-candidates.

Bioorganic 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 C6H4BF4KO, Recommanded Product: 6-Chlorobenzothiazol-2-ylamine.

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

Sambaiah, T. published the artcileSynthesis of N-[2H-[1,2,4]thiadiazolo[3′,2′:2,3]thiazolo[5,4-b]pyridin-2-ylidene]aroylamines, Recommanded Product: 5-Chlorothiazolo[5,4-b]pyridin-2-amine, the publication is Synthetic Communications (1990), 20(3), 355-64, database is CAplus.

The reaction of aminothiazolopyridines I (R = MeO, Cl) with R¹C₆H₄CONCS (R¹ = H, 3-Me, 4-Me, 4-MeO, 2-Cl, 4-Cl) in acetone gave (thiazolopyridinyl)thioureas II. Cyclization of II in the presence of PCl₅ in POCl₃ gave thiadiazolothiazolopyridinylidene)aroylamines III.

Synthetic Communications 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, Recommanded Product: 5-Chlorothiazolo[5,4-b]pyridin-2-amine.

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

Reddy, Velma Ganga published the artcilePyrazolo-benzothiazole hybrids: synthesis, anticancer properties and evaluation of antiangiogenic activity using in vitro VEGFR-2 kinase and in vivo transgenic zebrafish model, Formula: C7H5ClN2S, the publication is European Journal of Medicinal Chemistry (2019), 111609pp., database is CAplus and MEDLINE.

A series of new pyrazolo-benzothiazole hybrids I [R¹ = H, MeO, F, Cl; R² = H, Me, MeO, F, Cl] was synthesized and screened for their anticancer activity against several cancer cell lines [colon (HT-29), prostate (PC-3), lung (A549), glioblastoma (U87MG)] and normal human embryonic kidney cell line (Hek-293T). Compounds I [R¹ = H, R² = F, Cl; R¹ = F, R² = F, Cl; R¹ = Cl, R² = F, Cl; R¹ = MeO, R² = F, Cl] displayed significant anticancer activity against all tested cancer cell lines and compound I [R¹ = F, R² = Cl] showed most potent activity among the series with IC₅₀ values in the range 3.17-6.77 μM, even better than reference drug axitinib (4.88-21.7 μM). Compound I [R¹ = F, R² = Cl] also showed the strongest growth inhibition in 3D multicellular spheroids of PC-3 and U87MG cells. The mechanism of cellular toxicity in PC-3 cells was found to be cell cycle arrest and apoptosis induction through depolarisation of mitochondrial membrane potential, increased ROS production and subsequent DNA damage. Further, compound I [R¹ = F, R² = Cl] displayed significant in vitro (VEGFR-2 inhibition) and in vivo [transgenic zebrafish Tg(flila:EGFP) model] antiangiogenic properties. Overall, these results provided strong evidence that compound I [R¹ = F, R² = Cl] could be considered for a lead candidate in anticancer and antiangiogenic drug discovery.

European Journal of 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, Formula: C7H5ClN2S.

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

Rao, V. Rajeswar published the artcileSynthesis of some new types of 3-coumarinyl-substituted pyrazolopyrimidines and imidazothiazoles, Application of Methyl 2-(2-aminothiazol-4-yl)acetate, the publication is Chemistry of Heterocyclic Compounds (New York, NY, United States) (2008), 44(3), 360-365, database is CAplus.

The treatment of 3-[3-(dimethylamino)-1-oxo-2-propenyl]chromen-2-ones with 3-amino-4-cyanopyrazole gave 7-(2-oxo-2H-chromen-3-yl)pyrazolo[1,5-a]pyrimidine-3-carbonitriles. The reaction of 3-(2-bromoacetyl)coumarins with 2-amino-4-(methoxycarbonylmethyl)thiazole and 2-amino-4-methylthiazole gives Me 2-(6-(2-oxo-2H-chromen-3-yl)imidazo[2,1-b]thiazol-3-yl)acetate and 3-(2-methylimidazo[2,1-b]thiazol-6-yl)-2H-chromen-2-ones, resp.

Chemistry of Heterocyclic Compounds (New York, NY, United States) 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, Application of Methyl 2-(2-aminothiazol-4-yl)acetate.

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

van Deurzen, M. P. J. published the artcileChloroperoxidase catalyzed oxidations in t-butyl alcohol/water mixtures, Formula: C4H5NS2, the publication is Journal of Molecular Catalysis A: Chemical (1997), 117(1-3), 329-337, database is CAplus.

A symposium. Chloroperoxidase catalyzed oxidations of sulfides and indoles were performed in tert-Bu alc./water mixtures at ambient temperature tert-Bu alc./water (50:50, volume/volume) proved to be a good solvent system for performing synthetic oxidations catalyzed by chloroperoxidase. The sulfoxidation of alkyl aryl sulfides and related compounds catalyzed by chloroperoxidase in tert-Bu alc./water mixtures (50:50, volume/volume) was compared to the sulfoxidation in water. In both solvent systems, complete enantioselectivity to the R-sulfoxide (ee = 99) was observed with hydrogen peroxide as oxidant when the size of the alkyl moiety was smaller than Pr. The uncatalyzed, racemic sulfoxidation did not proceed under these conditions. This is in contrast to literature data on sulfoxidation in water, where enantioselectivities were lower due to this uncatalyzed reaction. Reactions in water generally proceed faster than reactions in the cosolvent system except for substrates which dissolve poorly in water or for solid substrates for which diffusion becomes an important limiting factor in water. The lower activity in tert-Bu alc./water for sulfoxidation and for indole oxidation is mainly due to an increase of the K_m value (thermodynamically controlled). Also a decrease of k_cat (catalytic turnover frequency) is observed, probably caused by a change in structure of the enzyme.

Journal of Molecular Catalysis A: Chemical 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 C19H17N2NaO4S, Formula: C4H5NS2.

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

Huang, Xinzhou published the artcileDesign of a novel photoelectrochemical enzymatic biofuel cell with high power output under visible light, Application In Synthesis of 30931-67-0, the publication is Chemical Engineering Journal (Amsterdam, Netherlands) (2022), 431(Part_2), 134037, database is CAplus.

Photoelectrochem. enzymic biofuel cell (PEBFC) shows the obvious advantages in the renewable energy conversion field. However, because of the low utilization efficiency of solar energy and the unendurable power output, PEBFC cannot satisfy the demand of practical applications. Herein, a novel PEBFC prototype is designed. Taking a TiO₂ nanorod arrays (NRAs) decorated graphene-cadmium sulfide quantum dots (GR-CdS QDs) hybrid at fluorine-doped tin oxide (FTO) glass electrode as the photoanode, it can catalyze the oxidation of ascorbic acid (AA) effectively, with the oxidation current being as high as -137.8μA cm^-2, and the anodic open circuit potential (EOCPa) reaching approx. -0.52 V; using a laccase-bound three-dimensional graphene-single walled carbon nanotubes (3D GR-SWCNTs-laccase) hybrid electrode as the biocathode, along with 2,2′-azinobis (3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt (ABTS), the biocathode can catalyze the reduction of oxygen remarkably, and the cathodic open circuit potential (EOCPc) is as high as 0.54 V. Under optimal conditions, such PEBFC can obtain sufficient high open circuit voltage (Voc) of 1.05 V and maximum power output d. (Pmax) of 227.5μW cm^-2, resp. Two PEBFCs connected in series can light a red light-emitting diode (LED) successfully.

Chemical Engineering Journal (Amsterdam, Netherlands) 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

Zhang, Xiaowei published the artcileStability, structure, and antioxidant activity of astaxanthin crystal from Haematococcus pluvialis, Formula: C18H24N6O6S4, the publication is Journal of the American Oil Chemists’ Society (2022), 99(5), 367-377, database is CAplus.

Crystallized anthaxanthin was prepared through the cleaning crystallization method and the stabilities during thermal, lighting, and pH treatment, and antioxidant activities in vitro were evaluated. The structural characterizations of astaxanthin crystal were verified by ¹H, ¹³C NMR, and XRD anal. The stability data showed that the astaxanthin crystal was more sensitive to heat, light, and pH compared to oleoresin. The sucrose had no outstanding influence on the astaxanthin crystal, while the stability of astaxanthin oleoresin slightly increased with the increase of sugar concentration The XRD and NMR spectra elucidated that the astaxanthin crystal was all trans structure. The astaxanthin crystal showed the dominant 1,1′-diphenyl-2-picrylhydrazyl (IC₅₀ 18.65 μmol L^-1), 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt ⁺(21.1 μmol L^-1), •OH (IC₅₀ 49.46 μmol L^-1) and ferric reducing antioxidant power (IC₅₀ 81.60 μmol L^-1) activities. The investigated results would be helpful for improving the development of astaxanthin crystal in food products.

Journal of the American Oil Chemists’ Society 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 C20H40O2, Formula: C18H24N6O6S4.

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

Jean, Mickael published the artcileSynthesis and evaluation of amides surrogates of dopamine D3 receptor ligands, Application In Synthesis of 329794-40-3, the publication is Bioorganic & Medicinal Chemistry Letters (2010), 20(18), 5376-5379, database is CAplus and MEDLINE.

Isosteric replacement of the amide function and modulation of the arylpiperazine moiety of known dopamine D3 receptor ligands led to potent and selective compounds Enhanced bioavailability and preferential brain distribution make (piperazinyl)butanamine derivative I a good candidate for pharmacol. and clin. evaluation.

Bioorganic & Medicinal Chemistry Letters published new progress about 329794-40-3. 329794-40-3 belongs to thiazole, auxiliary class Thiazole,Chloride,Benzene, name is 2-Chloro-5-phenylthiazole, and the molecular formula is C9H6ClNS, Application In Synthesis of 329794-40-3.

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

Ali-Torres, Jorge published the artcileInsights on the Binding of Thioflavin Derivative Markers to Amyloid-Like Fibril Models from Quantum Chemical Calculations, Application In Synthesis of 92-36-4, the publication is Journal of Physical Chemistry B (2013), 117(22), 6674-6680, database is CAplus and MEDLINE.

Thioflavin-T (ThT) is one of the most widely used dyes for staining and identifying amyloid fibrils, which share a common parallel in register β-sheet structure. Unfortunately, ThT is a charged mol., which limits its ability to cross the blood brain barrier and its use as an efficient dye for in vivo detection of amyloid fibrils. For this reason, several uncharged ThT derivatives have been designed and their binding properties to Aβ fibrils studied by fluorescence assays. However, there are still many unknowns on the binding mechanism and the role of noncovalent interactions on the affinity of these ligands toward β-sheet structures. The present contribution analyzes the binding of ThT (1) and neutral ThT derivatives (2-7) to a β-sheet model by means of quantum chem. B3LYP-D calculations and including solvent effects with the continuum CPCM method. Results show that, in all cases, ligand binding is mainly driven by dispersion interactions. In addition, ligands with -NH groups display hydrogen bond interactions with CO groups of the peptide strand, increasing the intrinsic affinity toward the β-sheet surface. Solvent effects notably reduce the affinity of charged ThT, as compared to neutral systems, due to its larger solvation energy. As a result, neutral derivatives display significantly higher affinities than ThT in solution, in agreement with exptl. observations. Anal. of the hydrogen bonding network of the β-sheet structure indicates that stacking interactions upon ligand binding induce a shortening of interstrand hydrogen bonding, suggesting a strengthening of the β-sheet.

Journal of Physical Chemistry B 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, Application In Synthesis of 92-36-4.

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