Category: thiazole

Novel synthesis of 2-thiazolines was written by Fernandez, Xavier;Fellous, Roland;Dunach, Elisabet. And the article was included in Tetrahedron Letters in 2000.Synthetic Route of C4H7NS This article mentions the following:

The synthesis of a series of 2-thiazolines was carried out under mild conditions from the corresponding thiazolidines, by a Ru-catalyzed/TBHP oxidation reaction conditions. The reaction was chemoselective towards the amine-imine oxidation and was also regioselective, affording the unsaturation at the 2-position of the heterocycle, even with thiazolidine substrates bearing ester groups at the 4-position. In the experiment, the researchers used many compounds, for example, 2-Methyl-4,5-dihydrothiazole (cas: 2346-00-1Synthetic Route of C4H7NS).

2-Methyl-4,5-dihydrothiazole (cas: 2346-00-1) belongs to thiazole derivatives. Thiazoles frequently appear in peptide studies. Thiazoles can also be used as protected formyl groups, which can be released in later stages of complex natural product synthesis. Thiazole sulfonation occurs only under forcing conditions: the action of oleum at 250 °C for 3 hours in the presence of mercury(II) sulfate leads to 65% formation of 5-thiazole sulfonic acid.Synthetic Route of C4H7NS

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

Unsymmetrical nickel (PCN) pincer complexes with a benzothiazole side-arm: Synthesis, characterization and electrochemical properties was written by Luconi, Lapo;Tuci, Giulia;Gafurov, Zufar N.;Mercuri, Giorgio;Kagilev, Alexey A.;Pettinari, Claudio;Morozov, Vladimir I.;Yakhvarov, Dmitry G.;Rossin, Andrea;Giambastiani, Giuliano. And the article was included in Inorganica Chimica Acta in 2021.Name: 2-Chlorobenzothiazole This article mentions the following:

The newly prepared unsym. PCN-pincer ligand with a benzothiazole side-arm 2-(3-((di-tert-butylphosphino)methyl)phenoxy)benzothiazole [BzTz(H)PCN] has been cyclometalated with anhydrous NiBr₂ to get the corresponding Ni^II square planar bromo complex [(BzTzPCN)NiBr] (1) after HBr elimination and C-H activation on the pincer central Ph ring. Starting from 1, reaction with AgF in toluene or with AgBF₄ in THF led to bromide abstraction and formation of the fluoro complex [(BzTzPCN)NiF] (2) and the ionic aqua species [(BzTzPCN)Ni(H₂O)][BF₄] (3), resp. All species have been characterized in solution (multinuclear ¹H, ¹³C{¹H}, ³¹P{¹H} and ¹¹B NMR spectroscopy) and in the solid state (single-crystal X-ray diffraction anal.). Finally, comparative electrochem. measurements (CV and in situ EPR-spectroelectrochem.) carried out on the halide complexes 1 and 2 revealed that the anodic oxidation process leads to the formation of stable Ni^III species bearing a coordinated bromide ligand in case of 1 and a fluoride-free complex in case of 2. In the experiment, the researchers used many compounds, for example, 2-Chlorobenzothiazole (cas: 615-20-3Name: 2-Chlorobenzothiazole).

2-Chlorobenzothiazole (cas: 615-20-3) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. The pyridine-type nitrogen in the thiazole ring deactivates the ring for electrophilic substitution reactions, which is further reduced in acid due to protonation of the thiazole ring.Name: 2-Chlorobenzothiazole

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

Detection and Prevention of Aggregation-based False Positives in STD-NMR-based Fragment Screening was written by Vom, Amelia;Headey, Stephen;Wang, Geqing;Capuano, Ben;Yuriev, Elizabeth;Scanlon, Martin J.;Simpson, Jamie S.. And the article was included in Australian Journal of Chemistry in 2013.Recommanded Product: 4-(2-Amino-4-thiazolyl)phenol This article mentions the following:

Aggregation of small organic compounds is a problem encountered in a variety of assay screening formats where it often results in detection of false positives. A saturation transfer difference-NMR-detected screen of a com. available fragment library, followed by biochem. assay, identified several inhibitors of the enzyme ketopantoate reductase. These inhibitors were subsequently revealed to be aggregation-based false positives. Modification of the fragment screen by addition of detergent in the saturation transfer difference-NMR experiments allowed an assay format to be developed that resulted in the identification of genuine hit mols. suitable for further development. In the experiment, the researchers used many compounds, for example, 4-(2-Amino-4-thiazolyl)phenol (cas: 57634-55-6Recommanded Product: 4-(2-Amino-4-thiazolyl)phenol).

4-(2-Amino-4-thiazolyl)phenol (cas: 57634-55-6) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Recommanded Product: 4-(2-Amino-4-thiazolyl)phenol

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

2-Substituted-thio-N-(4-substituted-thiazol/1H-imidazol-2-yl)acetamides as BACE1 inhibitors: Synthesis, biological evaluation and docking studies was written by Yan, Gang;Hao, Lina;Niu, Yan;Huang, Wenjie;Wang, Wei;Xu, Fengrong;Liang, Lei;Wang, Chao;Jin, Hongwei;Xu, Ping. And the article was included in European Journal of Medicinal Chemistry in 2017.SDS of cas: 105512-81-0 This article mentions the following:

In this work, a series of 2-substituted-thio-N-(4-substituted-thiazol/1H-imidazol-2-yl)acetamide derivatives, I (R¹ = Ph, 4-MeC₆H₄, 2-O₂NC₆H₄, etc.; R₂ = 2-MeOC₆H₄,3-MeOC₆H₄, 4-MeOC₆H₄, 3-EtOC₆H₄), II (R³ = Ph, 3,5-Cl₂-4-NH₂Ph; R⁴ = 3-MeOPh, 3-EtOPh), were developed as β-secretase (BACE-1) inhibitors. Supported by docking study, a small library of derivatives were designed, synthesized and biol. evaluated in vitro. In addition, the selected compounds were tested with affinity (K_D) towards BACE-1, blood brain barrier (BBB) permeability and cytotoxicity. The studies revealed that the most potent analog II (R³ = Ph; R⁴ = 3-EtOC₆H₄) (IC₅₀ = 4.6 μM) with high predicted BBB permeability and low cellular cytotoxicity, could serve as a good lead structure for further optimization. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(3-bromophenyl)thiazole (cas: 105512-81-0SDS of cas: 105512-81-0).

2-Amino-4-(3-bromophenyl)thiazole (cas: 105512-81-0) belongs to thiazole derivatives. Thiazoles in peptides or their ability to bind proteins, DNA and RNA has led to many synthetic studies and new applications. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.SDS of cas: 105512-81-0

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

Validated preclinical mouse model for therapeutic testing against multidrug-resistant Pseudomonas aeruginosa strains was written by Warawa, Jonathan M.;Duan, Xiaoxian;Anderson, Charles D.;Sotsky, Julie B.;Cramer, Daniel E.;Pfeffer, Tia L.;Guo, Haixun;Adcock, Scott;Lepak, Alexander J.;Andes, David R.;Slone, Stacey A.;Stromberg, Arnold J.;Gabbard, Jon D.;Severson, William E.;Lawrenz, Matthew B.. And the article was included in Microbiology Spectrum in 2022.Recommanded Product: 78110-38-0 This article mentions the following:

The rise in infections caused by antibiotic-resistant bacteria is outpacing the development of new antibiotics. The ESKAPE pathogens (Enterococcus faecium, Staphylococcus aureus, Klebsiella pneumoniae, Acinetobacter baumannii, Pseudomonas aeruginosa, and Enterobacter species) are a group of clin. important bacteria that have developed resistance to multiple antibiotics and are commonly referred to as multidrug resistant (MDR). The medical and research communities have recognized that, without new antimicrobials, infections by MDR bacteria will soon become a leading cause of morbidity and death. Therefore, there is an ever-growing need to expedite the development of novel antimicrobials to combat these infections. Toward this end, we set out to refine an existing mouse model of pulmonary Pseudomonas aeruginosa infection to generate a robust preclin. tool that can be used to rapidly and accurately predict novel antimicrobial efficacy. This refinement was achieved by characterizing the virulence of a panel of genetically diverse MDR P. aeruginosa strains in this model, by both 50% LD (LD₅₀) anal. and natural history studies. Further, we defined two antibiotic regimens (aztreonam and amikacin) that can be used as comparators during the future evaluation of novel antimicrobials, and we confirmed that the model can effectively differentiate between successful and unsuccessful treatments, as predicted by in vitro inhibitory data. This validated model represents an important tool in our arsenal to develop new therapies to combat MDR P. aeruginosa strains, with the ability to provide rapid preclin. evaluation of novel antimicrobials and support data from clin. studies during the investigational drug development process. IMPORTANCE The prevalence of antibiotic resistance among bacterial pathogens is a growing problem that necessitates the development of new antibiotics. Preclin. animal models are important tools to facilitate and speed the development of novel antimicrobials. Successful outcomes in animal models not only justify progression of new drugs into human clin. trials but also can support FDA decisions if clin. trial sizes are small due to a small population of infections with specific drug-resistant strains. However, in both cases the preclin. animal model needs to be well characterized and provide robust and reproducible data. Toward this goal, we have refined an existing mouse model to better predict the efficacy of novel antibiotics. This improved model provides an important tool to better predict the clin. success of new antibiotics. In the experiment, the researchers used many compounds, for example, 2-((((Z)-1-(2-Aminothiazol-4-yl)-2-(((2S,3S)-2-methyl-4-oxo-1-sulfoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid (cas: 78110-38-0Recommanded Product: 78110-38-0).

2-((((Z)-1-(2-Aminothiazol-4-yl)-2-(((2S,3S)-2-methyl-4-oxo-1-sulfoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid (cas: 78110-38-0) belongs to thiazole derivatives. Thiazole is a five-membered, unsaturated, planar, π-excessive heteroaromatic containing one sulfur atom and one pyridine-type nitrogen atom at position 3 of the cyclic ring system. The nitrogen in thiazole is sp2 hybridized and the lone pair of electrons localized on the nitrogen is less reactive due to increased aromatic character and decreased basicity. It is protonated and alkylated/acylated at nitrogen forming hydrochloride and quaternary thiazolium salt.Recommanded Product: 78110-38-0

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

Stereodivergent, Diels-Alder-initiated organocascades employing α,β-unsaturated acylammonium salts: scope, mechanism, and application was written by Abbasov, Mikail E.;Hudson, Brandi M.;Tantillo, Dean J.;Romo, Daniel. And the article was included in Chemical Science in 2017.Quality Control of (S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole hydrochloride This article mentions the following:

Chiral α,β-unsaturated acylammonium salts are novel dienophiles enabling enantioselective Diels-Alder-lactonization (DAL) organocascades leading to cis- and trans-fused, bicyclic γ- and δ-lactones from readily prepared dienes, commodity acid chlorides, and a chiral isothiourea organocatalyst under mild conditions. The authors describe extensions of stereodivergent DAL organocascades to other racemic dienes bearing pendant secondary and tertiary alcs., and application to a formal synthesis of (+)-dihydrocompactin is described. A combined exptl. and computational study of unsaturated acylammonium salt formation and the entire DAL organocascade pathway provide a rationalization of the effect of Bronsted base additives and enabled a controllable, diastereodivergent DAL process leading to a full complement of possible stereoisomeric products. Evaluation of free energy and enthalpy barriers in conjunction with exptl. observed temperature effects revealed that the DAL is a rare case of an entropy-controlled diastereoselective process. NMR anal. of diene alc.-Bronsted base interactions and computational studies provide a plausible explanation of observed stabilization of exo transition-state structures through H-bonding effects. In the experiment, the researchers used many compounds, for example, (S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole hydrochloride (cas: 16595-80-5Quality Control of (S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole hydrochloride).

(S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole hydrochloride (cas: 16595-80-5) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. The pyridine-type nitrogen in the thiazole ring deactivates the ring for electrophilic substitution reactions, which is further reduced in acid due to protonation of the thiazole ring.Quality Control of (S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole hydrochloride

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

Direct C-H Bond Activation of Benzoxazole and Benzothiazole with Aryl Bromides Catalyzed by Palladium(II)-N-heterocyclic Carbene Complexes was written by Kaloglu, Murat;Kaloglur, Nazan;Oezdemir, Ismail. And the article was included in Chinese Journal of Chemistry in 2018.Computed Properties of C14H11NS This article mentions the following:

Herein, a series of novel palladium(II)-NHC complexes (NHC=N-heterocyclic carbene) were synthesized. The structures of all novel complexes were characterized by ¹H NMR, ¹³C NMR, FT-IR spectroscopy and elemental anal. techniques. These palladium(II)-NHC complexes were tested as efficient catalysts in the direct C-H bond activation of benzoxazole and benzothiazole with aryl bromides in the presence of 1 mol% catalyst loading at 150 °C for 4 h. Under the given conditions, various aryl bromides were successfully applied as the arylating reagents to achieve the 2-arylbenzoxazoles and 2-arylbenzothiazoles in acceptable to high yields. In the experiment, the researchers used many compounds, for example, 2-(4-Methylphenyl)benzothiazole (cas: 16112-21-3Computed Properties of C14H11NS).

2-(4-Methylphenyl)benzothiazole (cas: 16112-21-3) belongs to thiazole derivatives. The higher aromaticity of thiazole is due to delocalization of a lone pair of sulfur electrons across the ring, which is evidenced by chemical shifts of ring hydrogen at δ 7.27 and 8.77 ppm (C2 and C4), indicating diamagnetic ring current. Electrophilic attack at nitrogen depends on the presence of electron density at nitrogen as well as the position and nature of substituent linked to the thiazole ring.Computed Properties of C14H11NS

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

Synthesis of N-Substituted Methyl 4H-Thieno[3,2-b]pyrrole-5-carboxylates was written by Torosyan, S. A.;Gimalova, F. A.;Zagitov, V. V.;Erastov, A. S.;Miftakhov, M. S.. And the article was included in Russian Journal of Organic Chemistry in 2018.Formula: C8H7NO2S This article mentions the following:

The alkylation of Me 4H-thieno[3,2-b]pyrrole-5-carboxylate with Me iodide and allyl, propargyl and benzyl bromides in the presence of sodium hydride in THF afforded the corresponding N-substituted derivatives I (R = Me, CH₂=CHCH₂, CH≡CCH₂, Bn). Some reactions of the alkylation products were studied. In the experiment, the researchers used many compounds, for example, Methyl 4H-thieno[3,2-b]pyrrole-5-carboxylate (cas: 82782-85-2Formula: C8H7NO2S).

Methyl 4H-thieno[3,2-b]pyrrole-5-carboxylate (cas: 82782-85-2) belongs to thiazole derivatives. Thiazole is a five-membered, unsaturated, planar, π-excessive heteroaromatic containing one sulfur atom and one pyridine-type nitrogen atom at position 3 of the cyclic ring system. The pyridine-type nitrogen in the thiazole ring deactivates the ring for electrophilic substitution reactions, which is further reduced in acid due to protonation of the thiazole ring.Formula: C8H7NO2S

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

Genomic landscape of drug response reveals mediators of anthelmintic resistance was written by Doyle, Stephen R.;Laing, Roz;Bartley, David;Morrison, Alison;Holroyd, Nancy;Maitland, Kirsty;Antonopoulos, Alistair;Chaudhry, Umer;Flis, Ilona;Howell, Sue;McIntyre, Jennifer;Gilleard, John S.;Tait, Andy;Mable, Barbara;Kaplan, Ray;Sargison, Neil;Britton, Collette;Berriman, Matthew;Devaney, Eileen;Cotton, James A.. And the article was included in Cell Reports in 2022.Recommanded Product: (S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole This article mentions the following:

Like other pathogens, parasitic helminths can rapidly evolve resistance to drug treatment. Understanding the genetic basis of anthelmintic drug resistance in parasitic nematodes is key to tracking its spread and improving the efficacy and sustainability of parasite control. Here, we use an in vivo genetic cross between drug-susceptible and multi-drug-resistant strains of Haemonchus contortus in a natural host-parasite system to simultaneously map resistance loci for the three major classes of anthelmintics. This approach identifies new alleles for resistance to benzimidazoles and levamisole and implicates the transcription factor cky-1 in ivermectin resistance. This gene is within a locus under selection in ivermectin-resistant populations worldwide; expression analyses and functional validation using knockdown experiments support that cky-1 is associated with ivermectin survival. Our work demonstrates the feasibility of high-resolution forward genetics in a parasitic nematode and identifies variants for the development of mol. diagnostics to combat drug resistance in the field. In the experiment, the researchers used many compounds, for example, (S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole (cas: 14769-73-4Recommanded Product: (S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole).

(S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole (cas: 14769-73-4) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). The pyridine-type nitrogen in the thiazole ring deactivates the ring for electrophilic substitution reactions, which is further reduced in acid due to protonation of the thiazole ring.Recommanded Product: (S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole

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

Lack of Detection of the Analgesic Properties of PF-05089771, a Selective Na_v1.7 Inhibitor, Using a Battery of Pain Models in Healthy Subjects was written by Siebenga, Pieter;van Amerongen, Guido;Hay, Justin L.;McDonnell, Aoibhinn;Gorman, Donal;Butt, Richard;Groeneveld, Geert Jan. And the article was included in Clinical and Translational Science in 2020.Computed Properties of C18H12Cl2FN5O3S2 This article mentions the following:

The aim was to demonstrate analgesic properties of a potent selective Na_v1.7 sodium channel blocker, PF-05089771, alone and concomitantly with pregabalin in healthy subjects using a battery of human evoked pain models. This was a double-blind, double-dummy, randomized, placebo-controlled, five-period cross-over study with PF-05089771 alone and PF-05089771 concomitantly with pregabalin as treatment arms with pregabalin, ibuprofen, and placebo as control arms (NCT02349607). A battery of human evoked pain models was used to investigate analgesic properties of PF-05089771. Twenty-five subjects were enrolled in the study of which 23 subjects completed all five periods. PF-05089771 alone did not differ from placebo on the primary pain end points. The same holds when comparing PF-05089771 concomitantly with pregabalin and pregabalin alone. Pregabalin showed significant effects relative to placebo on thermal pain on the normal skin and UVB skin (least squares means with 90% confidence interval: 0.63 (0.32-0.93) and 0.53 (0.11-0.96)), pressure stimulation (1.10 (1.04-1.18)), and cold pressor (1.22 (1.14-1.32)). Ibuprofen demonstrated significant effects on thermal pain UVB skin (1.26 (0.82-1.70)) and pressure stimulation assessment (1.08 (1.01-1.15)), consistent with historical results. This study did not demonstrate analgesic properties of PF-05089771 alone or concomitantly with pregabalin in a battery of pain models. In the experiment, the researchers used many compounds, for example, 4-(2-(3-Amino-1H-pyrazol-4-yl)-4-chlorophenoxy)-5-chloro-2-fluoro-N-(thiazol-4-yl)benzenesulfonamide (cas: 1235403-62-9Computed Properties of C18H12Cl2FN5O3S2).

4-(2-(3-Amino-1H-pyrazol-4-yl)-4-chlorophenoxy)-5-chloro-2-fluoro-N-(thiazol-4-yl)benzenesulfonamide (cas: 1235403-62-9) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1).Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Computed Properties of C18H12Cl2FN5O3S2

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