M.W=150-200归档 - Page 19 of 26 - Heterocyclic Building Blocks-Thiazole

Barilli, Alessio’s team published research in Journal of Medicinal Chemistry in 64 | CAS: 774230-95-4

Journal of Medicinal Chemistry published new progress about 774230-95-4. 774230-95-4 belongs to thiazole, auxiliary class Thiazole,Chloride,Aldehyde, name is 5-Chlorothiazole-2-ethanone, and the molecular formula is C5H4ClNOS, Application of 5-Chlorothiazole-2-ethanone.

Barilli, Alessio published the artcileFrom High-Throughput Screening to Target Validation: Benzo[d]isothiazoles as Potent and Selective Agonists of Human Transient Receptor Potential Cation Channel Subfamily M Member 5 Possessing In Vivo Gastrointestinal Prokinetic Activity in Rodents, Application of 5-Chlorothiazole-2-ethanone, the publication is Journal of Medicinal Chemistry (2021), 64(9), 5931-5955, database is CAplus and MEDLINE.

Transient receptor potential cation channel subfamily M member 5 (TRPM5) is a nonselective monovalent cation channel activated by intracellular Ca²⁺ increase. Within the gastrointestinal system, TRPM5 is expressed in the stoma, small intestine, and colon. In the search for a selective agonist of TRPM5 possessing in vivo gastrointestinal prokinetic activity, a high-throughput screening was performed and compound 1 was identified as a promising hit. Hit validation and hit to lead activities led to the discovery of a series of benzo[d]isothiazole derivatives Among these, compounds 61 and 64 showed nanomolar activity and excellent selectivity (>100-fold) vs. related cation channels. The in vivo drug metabolism and pharmacokinetic profile of compound 64 was found to be ideal for a compound acting locally at the intestinal level, with minimal absorption into systemic circulation. Compound 64 was tested in vivo in a mouse motility assay at 100 mg/kg, and demonstrated increased prokinetic activity.

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

Sever, Belgin’s team published research in Molecules in 25 | CAS: 95-24-9

Molecules 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 C22H12F6O6S2, Name: 6-Chlorobenzothiazol-2-ylamine.

Sever, Belgin published the artcileIn vitro and in silico evaluation of anticancer activity of new indole-based 1,3,4-oxadiazoles as EGFR and COX-2 inhibitors, Name: 6-Chlorobenzothiazol-2-ylamine, the publication is Molecules (2020), 25(21), 5190, database is CAplus and MEDLINE.

Epidermal growth factor receptor (EGFR) and cyclooxygenase-2 (COX-2) are crucial targetable enzymes in cancer management. Therefore, herein, new 2-[(5-((1H-indol-3-yl)methyl)-1,3,4-oxadiazol-2-yl)thio]-N-(thiazol/benzothiazol-2-yl)acetamides (2a-i) were designed and synthesized as EGFR and COX-2 inhibitors. The cytotoxic effects of compounds 2a-i on HCT116 human colorectal carcinoma, A549 human lung adenocarcinoma, and A375 human melanoma cell lines were determined using MTT assay. 2-[(5-((1H-Indol-3-yl)methyl)-1,3,4-oxadiazol-2-yl)thio]-N-(6-ethoxybenzothiazol-2-yl)acetamide (2e) exhibited the most significant anticancer activity against HCT116, A549, and A375 cell lines with IC₅₀ values of 6.43 ± 0.72μM, 9.62 ± 1.14μM, and 8.07 ± 1.36μM, resp., when compared with erlotinib (IC₅₀ = 17.86 ± 3.22μM, 19.41 ± 2.38μM, and 23.81 ± 4.17μM, resp.). Further mechanistic assays demonstrated that compound 2e enhanced apoptosis (28.35%) in HCT116 cells more significantly than erlotinib (7.42%) and caused notable EGFR inhibition with an IC₅₀ value of 2.80 ± 0.52μM when compared with erlotinib (IC₅₀ = 0.04 ± 0.01μM). However, compound 2e did not cause any significant COX-2 inhibition, indicating that this compound showed COX-independent anticancer activity. The mol. docking study of compound 2e emphasized that the benzothiazole ring of this compound occupied the allosteric pocket in the EGFR active site. In conclusion, compound 2e is a promising EGFR inhibitor that warrants further clin. investigations.

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

Chalopin, T.’s team published research in Organic & Biomolecular Chemistry in 14 | CAS: 885229-41-4

Organic & Biomolecular Chemistry published new progress about 885229-41-4. 885229-41-4 belongs to thiazole, auxiliary class Thiazole,Chloride,Ketone, name is 1-(2-Chlorothiazol-5-yl)ethanone, and the molecular formula is C5H4ClNOS, Computed Properties of 885229-41-4.

Chalopin, T. published the artcileSecond generation of thiazolylmannosides, FimH antagonists for E. coli-induced Crohn’s disease, Computed Properties of 885229-41-4, the publication is Organic & Biomolecular Chemistry (2016), 14(16), 3913-3925, database is CAplus and MEDLINE.

The anti-adhesive strategy, consisting of disrupting bacterial attachment to the host cells, is widely explored as an alternative to antibiotic therapies. Recently, thiazolylmannosides (TazMans) have been identified as strong anti-adhesives of E. coli strains implied in the gut inflammation of patients with Crohn’s disease. In this work, we developed a second generation of TazMans with improved chem. stability. The anomeric nitrogen was substituted by short linkers and the compounds were assessed against the bacterial adhesion FimH and the clin. isolated LF82 E. coli strain in four in vitro assays. The results obtained on the FimH adhesion alone and the whole bacteria enabled the identification of a candidate for further in vivo evaluations.

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

Singh, Anuradha’s team published research in Organic Letters in 15 | CAS: 329794-40-3

Organic 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 C13H18BClO3, Computed Properties of 329794-40-3.

Singh, Anuradha published the artcilePhotoredox-Mediated C-H Functionalization and Coupling of Tertiary Aliphatic Amines with 2-Chloroazoles, Computed Properties of 329794-40-3, the publication is Organic Letters (2013), 15(20), 5390-5393, database is CAplus and MEDLINE.

Herein, conditions for C-H functionalization of tertiary aliphatic amines and their subsequent coupling with a number of 2-chloroazole derivatives are reported. The reaction is facilitated by a catalytic amount of tris-fac-Ir(ppy)₃, with blue light irradiation and takes place under mild and convenient conditions. Most couplings take place with excellent regioselectivity. The reaction is tolerant of a number of functional groups and allows for rapid access to α-azole carbinamines e. g., I and II commonly found in post-translationally modified peptides.

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

Luo, Kai’s team published research in Journal of Organic Chemistry in 2016-06-03 | 20582-55-2

Journal of Organic Chemistry published new progress about Aromatic hydrocarbons Role: RCT (Reactant), RACT (Reactant or Reagent) (heteroarenes). 20582-55-2 belongs to class thiazole, and the molecular formula is C7H9NO2S, Synthetic Route of 20582-55-2.

Luo, Kai; Chen, Yao-Zhong; Chen, Li-Xian; Wu, Lei published the artcile< Autoxidative C(sp2)-P Formation: Direct Phosphorylation of Heteroarenes under Oxygen, Metal-Free, and Solvent-Free Conditions>, Synthetic Route of 20582-55-2, the main research area is phosphorylation heteroarene arylphosphine oxide; heteroaryl phosphine oxide preparation.

The authors reveal here a direct autoxidative phosphorylation of heteroarenes induced by O under metal-free and solvent-free conditions. This new methodol. provides an economical, operationally simple, and environmentally friendly approach toward (Het)C(sp2)-P formation with medium to excellent yields. Heteroarenes including thiazole and quinoxaline derivatives are applicable under standard conditions, which is testified via a radical mechanism.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Hagiya, Kazutake’s team published research in Synthesis in 2003-05-01 | 20582-55-2

Synthesis published new progress about Dialdehydes Role: SPN (Synthetic Preparation), PREP (Preparation). 20582-55-2 belongs to class thiazole, and the molecular formula is C7H9NO2S, Application In Synthesis of 20582-55-2.

Hagiya, Kazutake; Mitsui, Sunao; Taguchi, Hiroaki published the artcile< A facile and selective synthetic method for the preparation of aromatic dialdehydes from diesters via the amine-modified SMEAH reduction system>, Application In Synthesis of 20582-55-2, the main research area is facile synthetic preparation aromatic dialdehyde diester amine SMEAH reduction.

A new reduction system employing N-methylpiperazine-modified sodium bis(2-methoxyethoxy)aluminum hydride (NMP-SMEAH) for the conversion of aromatic diesters to dialdehydes is described. The method is plain and efficient, and can be carried out under mild and operationally simple conditions applicable for large scale productions.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Bittel, Amy M’s team published research in Scientific Reports in 2018-12-31 | 198904-53-9

Scientific Reports published new progress about Biological imaging. 198904-53-9 belongs to class thiazole, and the molecular formula is C10H7NOS, Safety of 4-(Thiazol-2-yl)benzaldehyde.

Bittel, Amy M.; Davis, Ashley M.; Wang, Lei; Nederlof, Michel A.; Escobedo, Jorge O.; Strongin, Robert M.; Gibbs, Summer L. published the artcile< Varied Length Stokes Shift BODIPY-Based Fluorophores for Multicolor Microscopy>, Safety of 4-(Thiazol-2-yl)benzaldehyde, the main research area is boron dipyrromethene aromatic aldehyde fluorophore stokes shift multicolor microscopy.

Multicolor microscopy tools necessary to localize and visualize the complexity of subcellular systems are limited by current fluorophore technol. While com. fluorophores cover spectral space from the UV to the near IR region and are optimized for conventional bandpass based fluorescence microscopy, they are not ideal for highly multiplexed fluorescence microscopy as they tend to have short Stokes shifts, restricting the number of fluorophores that can be detected in a single sample to four to five. Herein, we synthesized a library of 95 novel boron-dipyrromethene (BODIPY)-based fluorophores and screened their photophys., optical and spectral properties for their utility in multicolor microscopy. A subset of our BODIPY-based fluorophores yielded varied length Stokes shifts probes, which were used to create a five-color image using a single excitation with confocal laser scanning microscopy for the first time. Combining these novel fluorophores with conventional fluorophores could facilitate imaging in up to nine to ten colors using linear unmixing based microscopy approaches.

Scientific Reports published new progress about Biological imaging. 198904-53-9 belongs to class thiazole, and the molecular formula is C10H7NOS, Safety of 4-(Thiazol-2-yl)benzaldehyde.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Wang, Xinmou’s team published research in Organic Letters in 2020-12-04 | 20582-55-2

Organic Letters published new progress about Agrochemical fungicides. 20582-55-2 belongs to class thiazole, and the molecular formula is C7H9NO2S, COA of Formula: C7H9NO2S.

Wang, Xinmou; Chen, Yuming; Song, Hongjian; Liu, Yuxiu; Wang, Qingmin published the artcile< Construction of 2-(2-Arylphenyl)azoles via Cobalt-Catalyzed C-H/C-H Cross-Coupling Reactions and Evaluation of Their Antifungal Activity>, COA of Formula: C7H9NO2S, the main research area is biaryl azole cobalt catalyst agrochem fungicide; azole biphenyl amide cross coupling reaction.

Although compounds with a 2-(2-arylphenyl) benzoxazole motif are biol. important, there are only a few methods for synthesizing them. Herein, authors report an efficient method for synthesis of such compounds by means of cobalt-catalyzed C-H/C-H cross-coupling reactions. This method has a broad substrate scope and good tolerance for sensitive functional groups. In addition, authors demonstrate that introducing a heteroarene moiety to biphenyl compounds enhanced their antifungal activity.

Organic Letters published new progress about Agrochemical fungicides. 20582-55-2 belongs to class thiazole, and the molecular formula is C7H9NO2S, COA of Formula: C7H9NO2S.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Shergalis, Andrea’s team published research in Journal of Medicinal Chemistry in 2020-09-24 | 198904-53-9

Journal of Medicinal Chemistry published new progress about Antitumor agents. 198904-53-9 belongs to class thiazole, and the molecular formula is C10H7NOS, Synthetic Route of 198904-53-9.

Shergalis, Andrea; Xue, Ding; Gharbia, Fatma Z.; Driks, Hannah; Shrestha, Binita; Tanweer, Amina; Cromer, Kirin; Ljungman, Mats; Neamati, Nouri published the artcile< Characterization of Aminobenzylphenols as Protein Disulfide Isomerase Inhibitors in Glioblastoma Cell Lines>, Synthetic Route of 198904-53-9, the main research area is aminobenzylphenol structure screening preparation PDIA1 inhibitor glioblastoma.

Disulfide bond formation is a critical post-translational modification of newly synthesized polypeptides in the oxidizing environment of the endoplasmic reticulum and is mediated by protein disulfide isomerase (PDIA1). In this study, we report a series of α-aminobenzylphenol analogs as potent PDI inhibitors. The lead compound, AS15, is a covalent nanomolar inhibitor of PDI, and the combination of AS15 analogs with glutathione synthesis inhibitor buthionine sulfoximine (BSO) leads to synergistic cell growth inhibition. Using nascent RNA sequencing, we show that an AS15 analog triggers the unfolded protein response in glioblastoma cells. A BODIPY-labeled analog binds proteins including PDIA1, suggesting that the compounds are cell-permeable and reach the intended target. Taken together, these findings demonstrate an extensive biochem. characterization of a novel series of highly potent reactive small mols. that covalently bind to PDI.

Journal of Medicinal Chemistry published new progress about Antitumor agents. 198904-53-9 belongs to class thiazole, and the molecular formula is C10H7NOS, Synthetic Route of 198904-53-9.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Volgraf, Matthew’s team published research in Journal of Medicinal Chemistry in 2016-03-24 | 72054-60-5

Journal of Medicinal Chemistry published new progress about Crystal structure. 72054-60-5 belongs to class thiazole, and the molecular formula is C7H10N2O2S, Formula: C7H10N2O2S.

Volgraf, Matthew; Sellers, Benjamin D.; Jiang, Yu; Wu, Guosheng; Ly, Cuong Q.; Villemure, Elisia; Pastor, Richard M.; Yuen, Po-wai; Lu, Aijun; Luo, Xifeng; Liu, Mingcui; Zhang, Shun; Sun, Liang; Fu, Yuhong; Lupardus, Patrick J.; Wallweber, Heidi J. A.; Liederer, Bianca M.; Deshmukh, Gauri; Plise, Emile; Tay, Suzanne; Reynen, Paul; Herrington, James; Gustafson, Amy; Liu, Yichin; Dirksen, Akim; Dietz, Matthias G. A.; Liu, Yanzhou; Wang, Tzu-Ming; Hanson, Jesse E.; Hackos, David; Scearce-Levie, Kimberly; Schwarz, Jacob B. published the artcile< Discovery of GluN2A-Selective NMDA Receptor Positive Allosteric Modulators (PAMs): Tuning Deactivation Kinetics via Structure-Based Design>, Formula: C7H10N2O2S, the main research area is NMDA receptor allosteric modulator PAM deactivation structure design; crystal structure.

The N-methyl-D-aspartate receptor (NMDAR) is a Na+ and Ca2+ permeable ionotropic glutamate receptor that is activated by the coagonists glycine and glutamate. NMDARs are critical to synaptic signaling and plasticity, and their dysfunction has been implicated in a number of neurol. disorders, including schizophrenia, depression, and Alzheimer’s disease. Herein we describe the discovery of potent GluN2A-selective NMDAR pos. allosteric modulators (PAMs) starting from a high-throughput screening hit. Using structure-based design, we sought to increase potency at the GluN2A subtype, while improving selectivity against related α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptors (AMPARs). The structure-activity relationship of channel deactivation kinetics was studied using a combination of electrophysiol. and protein crystallog. Effective incorporation of these strategies resulted in the discovery of GNE-0723 (46), a highly potent and brain penetrant GluN2A-selective NMDAR PAM suitable for in vivo characterization.

Journal of Medicinal Chemistry published new progress about Crystal structure. 72054-60-5 belongs to class thiazole, and the molecular formula is C7H10N2O2S, Formula: C7H10N2O2S.

Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica