Day: November 29, 2022

Schlitzer, Martin published the artcileSynthesis of potential aldose reductase inhibitors based on minimal pharmacophore requirements, Synthetic Route of 92-36-4, the publication is Journal of Pharmacy and Pharmacology (2001), 53(6), 831-839, database is CAplus and MEDLINE.

A series of 17 compounds was synthesized based on the premise that the minimal pharmacophore for aldose reductase inhibition requires the presence of both an aryl group and a polar group connected by a linking structure. Three groups of compounds were synthesized, the first possessing a 4-(6-methyl-2-benzothiazolyl)aniline or 2-aminobenzothiazole group as the aryl group, the second possessing a 2-naphthyl as the aryl group and the third possessing either a 2-phenyl-4-thiazolyl or 5-(2-nitrophenyl)-2-furanyl as the aryl group. In all three of these groups the carboxylate or its Me ester are linked to the aryl group through various lengths of methylene carbons and amide or cinnamide groups. Optimal activity was observed when the carboxyl group was separated from the aryl group by a linking structure of five atoms in length. Both a double bond and an amide moiety are well tolerated in the linking structure.

Journal of Pharmacy and Pharmacology 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, Synthetic Route of 92-36-4.

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

Bilodeau, Mark T. published the artcileThe discovery of N-(1,3-thiazol-2-yl)pyridin-2-amines as potent inhibitors of KDR kinase, Recommanded Product: 2-Chloro-5-phenylthiazole, the publication is Bioorganic & Medicinal Chemistry Letters (2004), 14(11), 2941-2945, database is CAplus and MEDLINE.

An azo-dye lead was modified to a N-(1,3-thiazol-2-yl)pyridin-2-amine series of KDR kinase inhibitors through the use of rapid analog libraries. The two lead compounds were N-butyl-N,3-dimethyl-4-[(5-nitro-2-thiazolyl)azo]benzenamine and N-(5-phenyl-2-thiazolyl)benzamide. This class has been found to be potent, selective, and of low mol. weight Mol. modeling has postulated an interesting conformational preference and binding mode for these compounds in the active site of the enzyme. A binding mode was proposed for the lead compound N-(5-phenyl-2-thiazolyl)-2-pyridinamine (I) in the KDR kinase active site.

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, Recommanded Product: 2-Chloro-5-phenylthiazole.

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

Ben Hassine, Amna published the artcileUntargeted phytochemical profile, antioxidant capacity and enzyme inhibitory activity of cultivated and wild lupin seeds from Tunisia, Application In Synthesis of 30931-67-0, the publication is Molecules (2021), 26(11), 3452, database is CAplus and MEDLINE.

Lupin seeds can represent a valuable source of phenolics and other antioxidant compounds In this work, a comprehensive anal. of the phytochem. profile was performed on seeds from three Lupinus species, including one cultivar (Lupinus albus) and two wild accessions (Lupinus cossentinii and Lupinus luteus), collected from the northern region of Tunisia. Untargeted metabolomic profiling allowed to identify 249 compounds, with a great abundance of phenolics and alkaloids. In this regard, the species L. cossentinii showed the highest phenolic content, being 6.54 mg/g DW, followed by L. luteus (1.60 mg/g DW) and L. albus (1.14 mg/g DW). The in vitro antioxidant capacity measured by the ABTS assay on seed extracts ranged from 4.67 to 17.58 mg trolox equivalent (TE)/g, recording the highest values for L. albus and the lowest for L. luteus. The DPPH radical scavenging activity ranged from 0.39 to 3.50 mg TE/g. FRAP values varied between 4.11 and 5.75 mg TE/g. CUPRAC values for lupin seeds ranged from 7.20 to 8.95 mg TE/g, recording the highest for L. cossentinii. The results of phosphomolybdenum assay and metal chelation showed similarity between the three species of Lupinus. The acetylcholinesterase (AChE) inhibition activity was detected in each methanolic extract analyzed with similar results. Regarding the butyrylcholinesterase (BChE) enzyme, it was weakly inhibited by the Lupinus extracts; in particular, the highest activity values were recorded for L. albus (1.74 mg GALAE/g). Overall, our results showed that L. cossentinii was the most abundant source of polyphenols, consisting mainly in tyrosol equivalent (5.82 mg/g DW). Finally, significant correlations were outlined between the phenolic compounds and the in vitro biol. activity measured, particularly when considering flavones, phenolic acids and lower-mol.-weight phenolics.

Molecules 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

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

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

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

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

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

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

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