Month: October 2022

Nitsche, Christoph; Schreier, Verena N.; Behnam, Mira A. M.; Kumar, Anil; Bartenschlager, Ralf; Klein, Christian D. published the artcile< Thiazolidinone-Peptide Hybrids as Dengue Virus Protease Inhibitors with Antiviral Activity in Cell Culture>, Application of C10H9NOS2, the main research area is thiazolidindione rhodanine peptide preparation antiviral dengue virus protease inhibitor.

The protease of dengue virus is a promising target for antiviral drug discovery. We here report a new generation of peptide-hybrid inhibitors of dengue protease that incorporate N-substituted 5-arylidenethiazolidinone heterocycles (rhodanines and thiazolidinediones) as N-terminal capping groups of the peptide moiety. The compounds were extensively characterized with respect to inhibition of various proteases, inhibition mechanisms, membrane permeability, antiviral activity, and cytotoxicity in cell culture. A sulfur/oxygen exchange in position 2 of the capping heterocycle (thiazolidinedione-capped vs rhodanine-capped peptide hybrids) has a significant effect on these properties and activities. The most promising in vitro affinities were observed for thiazolidinedione-based peptide hybrids containing hydrophobic groups with Ki values between 1.5 and 1.8 μM and competitive inhibition mechanisms. Rhodanine-capped peptide hybrids with hydrophobic substituents have, in correlation with their membrane permeability, a more pronounced antiviral activity in cell culture than the thiazolidinediones.

Journal of Medicinal Chemistry published new progress about Antiviral agents. 10574-69-3 belongs to class thiazole, and the molecular formula is C10H9NOS2, Application of C10H9NOS2.

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

Geary, Gemma C.; Nortcliffe, Andrew; Pearce, Christopher A.; Hamza, Daniel; Jones, Geraint; Moody, Christopher J. published the artcile< Densely functionalised spirocyclic oxetane-piperidine scaffolds for drug discovery>, Recommanded Product: Thiazole-5-carboxyaldehyde, the main research area is spirocyclic oxetane piperidine scaffold preparation rearrangement gold catalyst.

A spirocyclic, sp3-atom rich oxetane-containing scaffold was synthesized in just two steps via a gold catalyzed propargylic alc. rearrangement. The key gold cyclization can be undertaken on a 40 g scale allowing the preparation of 419 lead-like compounds based on the scaffold for the European Lead Factory.

Bioorganic & Medicinal Chemistry published new progress about Oxetanes Role: SPN (Synthetic Preparation), PREP (Preparation) (spirocyclic). 1003-32-3 belongs to class thiazole, and the molecular formula is C4H3NOS, Recommanded Product: Thiazole-5-carboxyaldehyde.

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

Luo, Jinqiu; Yang, Jinfeng; Li, Guangjie; Yang, Sheng; Zhou, Yibo; Li, Jun-Bin; Huang, Ge; Hu, Yibo; Zou, Shuangfa; Zeng, Qinghai; Yang, Ronghua published the artcile< Noncovalently Caged Firefly Luciferins Enable Amplifiable Bioluminescence Sensing of Hyaluronidase-1 Activity in Vivo>, Product Details of C11H8N2O3S2, the main research area is noncovalently caged firefly luciferins bioluminescence sensor hyaluronidase 1; bioluminescence; enzymatic assay; hyaluronidase; in vivo bioimaging; nanosensor; signal amplification.

Hyaluronidase 1 (Hyal-1) is an important enzyme involved in intracellular hyaluronic acid (HA) catabolism for performing various physiol. functions, and its aberrant level is closely associated with many malignant diseases. Bioluminescence imaging is advantageous for monitoring Hyal-1 activity in vivo, but it remains challenging to design an available probe for differentiating Hyal-1 from other isoforms by a traditional strategy that covalently masks the firefly luciferase substrate. Herein, we, for the first time, present a noncovalently caging approach to construct a Hyal-1-specific bioluminogenic nanosensor by entrapping D-luciferin (D-Luc) inside the cholesterylamine-modified HA (CHA) nanoassembly to inhibit the bioluminescence production When encountered with intracellular Hyal-1, CHA could be fully dissembled to liberate multiple copies of the loaded D-Luc, thereby emitting light by the luciferase-catalyzed bioluminescence reaction. Because of its cascade signal amplification feature, D-Luc@CHA displayed a remarkable “”turn-on”” response (248-fold) to 5μg/mL Hyal-1 with a detection limit of 0.07 ng/mL. Importantly, bioluminescence imaging results validated that D-Luc@CHA could be competent for dynamically visualizing endogenous Hyal-1 changes in living cells and animals and possessed the capability of discriminating between normal and cancer cells, thus offering a promising toolbox to evaluate Hyal-1 roles in biol. processes as well as to diagnose Hyal-1-related diseases.

ACS Sensors published new progress about Bioluminescent imaging. 2591-17-5 belongs to class thiazole, and the molecular formula is C11H8N2O3S2, Product Details of C11H8N2O3S2.

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

Kerdesky, Francis A. J.; Seif, Louis S. published the artcile< Catalytic hydrogenation of halothiazoles>, Related Products of 1003-32-3, the main research area is halothiazole hydrogenation dechlorination palladium catalyst.

The hydrogenation of halothiazoles I (R = R1 = H, R2 = Br; R = R1 = Br, R2 = H; R = R2 = Br, Cl, R1 = CHO, CH2OH) to I (R = R2 = H, R1 = H, CHO, CH2OH) is described. The best results were obtained utilizing 10% palladium on carbon as catalyst at four atmospheres of pressure with the bromide derivatives

Synthetic Communications published new progress about Dechlorination. 1003-32-3 belongs to class thiazole, and the molecular formula is C4H3NOS, Related Products of 1003-32-3.

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

Jaffett, Victor A.; Nerurkar, Alok; Cao, Xufeng; Guzei, Ilia A.; Golden, Jennifer E. published the artcile< Telescoped synthesis of C3-functionalized (E)-arylamidines using Ugi-Mumm and regiospecific quinazolinone rearrangements>, Application In Synthesis of 1003-32-3, the main research area is arylamidine stereoselective preparation; azidobenzoic acid isocyanide aldehyde bismethylaminoethane Ugi Mumm regiospecific rearrangement.

An efficient four-step, six-transformation protocol was developed to afford bioactive N-alkyl- or N-arylamide (E)-arylamidines I (R1 = Cy, 4-OMeC6H4, i-Pr, etc.; R2 = i-Pr, i-Bu, H, etc.; R3 = H, 5-CH3, 5-F, etc.) featuring strategic amidine C3 modifications which were inaccessible or low yielding by previous methods. This synthetic approach, exemplified with 24 amidines and requiring only a single purification, highlights a multicomponent Ugi-Mumm rearrangement to afford highly diversified quinazolinones which undergo regiospecific rearrangement to afford new amidines. The method extensively broadens the structural scope of this new class of trisubstituted amidines and demonstrates the tolerance of regional C3 amidine steric bulk, visualized with X-ray crystallog. anal.

Organic & Biomolecular Chemistry published new progress about Aldehydes Role: RCT (Reactant), RACT (Reactant or Reagent). 1003-32-3 belongs to class thiazole, and the molecular formula is C4H3NOS, Application In Synthesis of 1003-32-3.

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

Hansen, Ida K. O.; Loevdahl, Tomas; Simonovic, Danijela; Hansen, Kine O.; Andersen, Aaron J. C.; Devold, Hege; Richard, C. Eline S. M.; Andersen, Jeanette H.; Strom, Morten B.; Haug, Tor published the artcile< Antimicrobial activity of small synthetic peptides based on the marine peptide turgencin a: prediction of antimicrobial peptide sequences in a natural peptide and strategy for optimization of potency>, Recommanded Product: (S)-2-(6-Hydroxybenzo[d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid, the main research area is turgencin antimicrobial peptide Escherichia Staphylococcus; Arctic; Synoicum turgens; antimicrobial; ascidian; peptide; synthetic.

Turgencin A, a potent antimicrobial peptide isolated from the Arctic sea squirt Synoicum turgens, consists of 36 amino acid residues and three disulfide bridges, making it challenging to synthesize. The aim of the present study was to develop a truncated peptide with an antimicrobial drug lead potential based on turgencin A. The experiments consisted of: (1) sequence anal. and prediction of antimicrobial potential of truncated 10-mer sequences; (2) synthesis and antimicrobial screening of a lead peptide devoid of the cysteine residues; (3) optimization of in vitro antimicrobial activity of the lead peptide using an amino acid replacement strategy; and (4) screening the synthesized peptides for cytotoxic activities. In silico anal. of turgencin A using various prediction software indicated an internal, cationic 10-mer sequence to be putatively antimicrobial. The synthesized truncated lead peptide displayed weak antimicrobial activity. However, by following a systematic amino acid replacement strategy, a modified peptide was developed that retained the potency of the original peptide. The optimized peptide StAMP-9 displayed bactericidal activity, with minimal inhibitory concentrations of 7.8 μg/mL against Staphylococcus aureus and 3.9 μg/mL against Escherichia coli, and no cytotoxic effects against mammalian cells. Preliminary experiments indicate the bacterial membranes as immediate and primary targets.

International Journal of Molecular Sciences published new progress about Anti-inflammatory agents. 2591-17-5 belongs to class thiazole, and the molecular formula is C11H8N2O3S2, Recommanded Product: (S)-2-(6-Hydroxybenzo[d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid.

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

Zhu, Ziqi; Xiao, Jieshuai; Li, Mingjie; Shi, Zhuangzhi published the artcile< Nickel-Catalyzed Intermolecular Asymmetric Addition of Aryl Iodides across Aldehydes>, Recommanded Product: Thiazole-5-carboxyaldehyde, the main research area is diarylmethanol preparation enantioselective; aryl iodide asym addition aldehyde nickel catalyst; Asymmetric Addition; Chiral Alcohols; Enantioselectivity; Nickel Catalysis.

Enantioenriched alcs. comprise much of the framework of organic mols. Here, the authors first report that chiral nickel complexes can catalyze the intermol. enantioselective addition of aryl iodides across aldehydes to provide diverse optically active secondary alcs. using zinc metal as the reducing agent. This method shows a broad substrate scope under mild reaction conditions and precludes the traditional strategy through the pre-generation of organometallic reagents. Mechanistic studies indicate that an in situ formed arylnickel, instead of an arylzinc, adds efficiently to the aldehydes, forming a new C-C bond and a chiral nickel alkoxide that may be turned over by zinc powder.

Angewandte Chemie, International Edition published new progress about Addition reaction catalysts, stereoselective (intermol.). 1003-32-3 belongs to class thiazole, and the molecular formula is C4H3NOS, Recommanded Product: Thiazole-5-carboxyaldehyde.

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

Lu, Cui-Fen; Zhang, Shou-Bo; Li, Yan; Yang, Gui-Chun; Chen, Zu-Xing published the artcile< Stereoselective synthesis of (R)-10-methyltridecan-2-one, the sex pheromone of the southern corn rootworm, using (4S)-benzylthiazolidinethione as a chiral auxiliary>, Application In Synthesis of 171877-39-7, the main research area is methyltridecanone stereoselective synthesis Michael addition benzylthiazolidinethione chiral auxiliary.

The stereoselective synthesis of (R)-10-methyltridecan-2-one, the sex pheromone of the southern corn rootworm, was carried out in 20.7% overall yield based on (4S)-benzylthiazolidine-2-thione (five steps). In the crucial step, the stereogenic center was generated by an asym. Michael addition using enantiomerically pure (4S)-benzylthiazolidine-2-thione as a chiral auxiliary.

Tetrahedron: Asymmetry published new progress about Michael reaction, stereoselective. 171877-39-7 belongs to class thiazole, and the molecular formula is C10H11NS2, Application In Synthesis of 171877-39-7.

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

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>, Synthetic Route of 3034-56-8, 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. 3034-56-8 belongs to class thiazole, and the molecular formula is C3HBrClNS, Synthetic Route of 3034-56-8.

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

Aryanasab, F.; Shokri, A.; Saidi, M. R. published the artcile< A simple approach to the synthesis of 3-substituted rhodanines and thiazolidine-2,4-diones>, Quality Control of 10574-69-3, the main research area is rhodanine thiazolidinedione preparation green chem; amine primary carbon disulfide bromoacetate methyl three component reaction.

A synthesis of 3-substituted rhodanine and thiazolidine-2,4-dione derivatives I [X = S, O; R = CH2:CHCH2, CH3CH(CH3)CH2, 3,4-Cl2C6H3, etc.] starting from primary amines RNH2, carbon disulfide, and Me 2-bromoacetate, were described. The reaction proceeds successfully both in water and under solvent-free conditions, but 2-thioxothiazolidin-4-one (rhodanine) derivatives I (X = S) were obtained under solvent-free conditions, and thiazolidine-2,4-dions I (X = O) were formed when water was used as the solvent.

Scientia Iranica, Transaction C: Chemistry, Chemical Engineering published new progress about Green chemistry. 10574-69-3 belongs to class thiazole, and the molecular formula is C10H9NOS2, Quality Control of 10574-69-3.

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