Month: February 2023

Site-Selective Pd-Catalyzed C(sp³)-H Arylation of Heteroaromatic Ketones was written by Kudashev, Anton;Baudoin, Olivier. And the article was included in Chemistry – A European Journal in 2021.COA of Formula: C3H2BrNS This article mentions the following:

A ligand-controlled site-selective C(sp³)-H arylation of heteroaromatic ketones had been developed using Pd catalysis to gave ArC(O)CHR¹CH₂R² [Ar = thiazol-2-yl, 2-pyridyl, 2-quinolyl, etc.; R¹ = Ph, 4-MeC₆H₄, 2-naphthyl, etc.; R² = H, Me, ph, etc.]. The reaction occurred selectively at the α- or β-position of the ketone side-chain. The switch from α- or β-arylation was realized by addition of a pyridone ligand. The α-arylation process showed broad scope and high site- and chemoselectivity, whereas the β-arylation was more limited. Mechanistic investigations suggested that α-arylation occurs through C-H activation/oxidative addition/reductive elimination whereas β-arylation involves desaturation and aryl insertion. In the experiment, the researchers used many compounds, for example, 2-Bromothiazole (cas: 3034-53-5COA of Formula: C3H2BrNS).

2-Bromothiazole (cas: 3034-53-5) belongs to thiazole derivatives. The thiazole ring has been identified as a central feature of numerous natural products, perhaps the most famous example of which is epothilone.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.COA of Formula: C3H2BrNS

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

Synthesis and biological evaluation of (R)-3,3,3-trifluoro-2-hydroxy-2-methylpropionamides as pyruvate dehydrogenase kinase 1 (PDK1) inhibitors to reduce the growth of cancer cells was written by Zhang, Shao-Lin;Zhang, Wen;Yang, Zheng;Hu, Xiaohui;Tam, Kin Yip. And the article was included in European Journal of Pharmaceutical Sciences in 2017.Application of 2103-99-3 This article mentions the following:

Most cancer cells exhibit a high rate of glycolysis and reduced capacity in mitochondrial oxidative phosphorylation. The expression of pyruvate dehydrogenase kinases (PDKs) was found to be increased in many cancer cells. Inhibition of PDKs increases the oxidative phosphorylation of glucose, which may disrupt the balance between the demand and supply of oxygen in cancer cell, thus leading to cell death. Several reports suggested that compounds containing (R)-3,3,3-trifluoro-2-hydroxy-2-methylpropionamide group could inhibit PDKs in pyruvate dehydrogenase primary enzymic assay. However, none of them were capable of reducing the growth of cancer cells. Herein, we report the synthesis and biol. evaluation of some novel PDK1 inhibitors containing the (R)-3,3,3-trifluoro-2-hydroxy-2-methylpropionamide warhead. Excitingly, these novel PDK1 inhibitors exhibited good potency to reduce the growth of cancer cells. We have demonstrated that these compounds could phys. associate with PDK1 and activate pyruvate dehydrogenase in low micromolar levels. In the experiment, the researchers used many compounds, for example, 4-(4-Chlorophenyl)thiazol-2-amine (cas: 2103-99-3Application of 2103-99-3).

4-(4-Chlorophenyl)thiazol-2-amine (cas: 2103-99-3) belongs to thiazole derivatives. Thiazole rings are planar and aromatic. Thiazoles are characterized by larger pi-electron delocalization than the corresponding oxazoles and have therefore greater aromaticity.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Application of 2103-99-3

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

Synthesis and biological study of 2-amino-4-aryl-5-chloropyrimidine analogues as inhibitors of VEGFR-2 and cyclin dependent kinase 1 (CDK1) was written by Huang, Shenlin;Li, Ronghua;Connolly, Peter J.;Emanuel, Stuart;Fuentes-Pesquera, Angel;Adams, Mary;Gruninger, Robert H.;Seraj, Jabed;Middleton, Steven A.;Davis, Jeremy M.;Moffat, David F. C.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2007.Safety of 2,4-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole This article mentions the following:

The series of 2-amino-4-aryl-5-chloropyrimidines, e.g., I, was discovered to be potent for both VEGFR-2 and CDK1. Described here are the chem. for analog synthesis, SAR study, and its kinase selectivity profiling. The full rat PK data and in vivo efficacy study are also included. In the experiment, the researchers used many compounds, for example, 2,4-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole (cas: 859833-13-9Safety of 2,4-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole).

2,4-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole (cas: 859833-13-9) 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.Safety of 2,4-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole

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

n-Channel Organic Semiconductors Derived from Air-Stable Four-Coordinate Boron Complexes of Substituted Thienylthiazoles was written by Hecht, Reinhard;Kade, Juliane;Schmidt, David;Nowak-Krol, Agnieszka. And the article was included in Chemistry – A European Journal in 2017.Product Details of 121359-48-6 This article mentions the following:

Three acceptor-π-bridge-acceptor (A-π-A) mols. derived from 2-(3-boryl-2-thienyl)thiazole have been synthesized and thoroughly characterized. Incorporation of a B-N unit into thienylthiazole and attachment of suitable acceptor moieties allowed to obtain ambient-stable A-π-A mols. with low-lying LUMO levels. Their potential for applications in organic electronics was tested in vacuum-deposited organic thin film transistors (OTFT). The OTFT device based on boryl-thienylthiazole and 1,1-dicyanomethylene-3-indanone (DCIND) acceptor moieties showed an electron mobility of ≈1.4×10^-2 cm² V^-1 s^-1 in air, which is the highest electron mobility reported to date for organoboron small mols. Conversely, the device employing the malononitrile (MAL) derivative as an active layer did not show any charge transport behavior. As suggested by single crystal X-ray anal. of indandione (IND) and MAL derivatives, the enhanced mobility of IND (and DCIND) in comparison to the MAL mol. can be attributed to the effective two-dimensional π-stacking in the solid state imparted by the acceptor moieties with an extended π-surface. In the experiment, the researchers used many compounds, for example, 2-(Tributylstannyl)thiazole (cas: 121359-48-6Product Details of 121359-48-6).

2-(Tributylstannyl)thiazole (cas: 121359-48-6) belongs to thiazole derivatives. Thiazole rings are planar and aromatic. Thiazoles are characterized by larger pi-electron delocalization than the corresponding oxazoles and have therefore greater aromaticity. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Product Details of 121359-48-6

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

Effects of certain purified Chinese herbal medicinal compound polysaccharide on cellular immunity and humoral immunity in chicken was written by Shang, Yun-xia;Zhu, Xiao-qing;Gu, Xin-li;Li, Xiao-zhen;Qiao, Hai-bo;Jia, Shu-hong;Zhang, Dong-sheng. And the article was included in Zhongguo Xumu Shouyi in 2015.Safety of (S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole hydrochloride This article mentions the following:

In order to select the best dose of certain purified Chinese herbal medicinal compound polysaccharide (cCHMPS), which had been proven to significantly affect the immunity of mice, three hundred one-day-old male Liangfeng Green-feet Ma chickens were randomly divided into six groups, namely control group, levamisole hydrochloride (LM) group, Astragalus polysaccharide (APS) group, high, medium and low-dose purified cCHMPS group, and with 50 chickens for each group. Eight-day-old chickens were vaccined with physiol. saline, LM, APS, high, medium and low-dose purified cCHMPS, once a day for 7 consecutive days. On days 8, 14, 21, 28, 35 and 42 after the first vaccination, 5 chickens’ blood for each group were sampled for determination of T, B lymphocyte proliferation activities and NDV antibody levels. The results showed that APS and purified cCHMPS at different doses could significantly or extremely significantly promote the proliferation of peripheral T, B lymphocytes (P<0.05; P<0.01), increase the concentrations of NDV antibody, enhance cellular immunity and humoral immunity, and the medium-dose purified cCHMPS was the best. In the experiment, the researchers used many compounds, for example, (S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole hydrochloride (cas: 16595-80-5Safety 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. Thiazole rings are planar and aromatic. Thiazoles are characterized by larger pi-electron delocalization than the corresponding oxazoles and have therefore greater aromaticity. 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.Safety of (S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole hydrochloride

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

Determination of the main metabolite (desethyl KBT-3022) of a new antiplatelet agent, KBT-3022, in plasma by gas chromatography was written by Nakada, Yuichiro;Shimada, Hitoshi;Awata, Norio. And the article was included in Yakugaku Zasshi in 1992.Application In Synthesis of Ethyl 2-(2-(4,5-bis(4-methoxyphenyl)thiazol-2-yl)-1H-pyrrol-1-yl)acetate This article mentions the following:

A highly sensitive, accurate and reproducible gas chromatog. method for the determination of a main metabolite, 2-[4,5-bis(4-methoxyphenyl)thiazol-2-yl] pyrrolyl acetic acid (desethyl KBT-3022) of a new antiplatelet agent, Et 2-[4,5-bis(4-methoxyphenyl)thiazol-2-yl]pyrrol-1-yl acetate (KBT-3022), in human or dog plasma has been developed. Desethyl KBT-3022 in plasma was extracted with a mixture of n-hexane and dichloromethane (1:1) and was derivatized with pentafluorobenzyl bromide. The obtained pentafluorobenzyl derivative of desethyl KBT-3022 in plasma was separated by HPLC. After the separation, the pentafluorobenzyl derivative of desethyl KBT-3022 was detected by gas chromatog. Gas chromatog. was performed with an Ultra 1 column (12 m × 0.22 mm i.d., film thickness 0.33 μm), using an electron capture detector. 2-[2-{4,5-Bis(4-methoxyphenyl)thiazol-2-yl}pyrrol-1-yl]propionic acid was used as internal standard The detection limit of desethyl KBT-3022 in plasma was 0.2 ng/mL. The coefficients of variation were <5.3%. This method was applied to th determination of the plasma concentration of desethyl KBT-3022 after oral administration of KBT-3022 to dogs. In the experiment, the researchers used many compounds, for example, Ethyl 2-(2-(4,5-bis(4-methoxyphenyl)thiazol-2-yl)-1H-pyrrol-1-yl)acetate (cas: 101001-34-7Application In Synthesis of Ethyl 2-(2-(4,5-bis(4-methoxyphenyl)thiazol-2-yl)-1H-pyrrol-1-yl)acetate).

Ethyl 2-(2-(4,5-bis(4-methoxyphenyl)thiazol-2-yl)-1H-pyrrol-1-yl)acetate (cas: 101001-34-7) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). 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.Application In Synthesis of Ethyl 2-(2-(4,5-bis(4-methoxyphenyl)thiazol-2-yl)-1H-pyrrol-1-yl)acetate

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

Synthesis and Evaluation of Three ¹⁸F-Labeled Aminophenylbenzothiazoles as Amyloid Imaging Agents was written by Serdons, Kim;Van Laere, Koen;Janssen, Peter;Kung, Hank F.;Bormans, Guy;Verbruggen, Alfons. And the article was included in Journal of Medicinal Chemistry in 2009.Synthetic Route of C7H4N2O2S This article mentions the following:

Three ¹⁸F-labeled fluorophenylbenzothiazoleamines I (R = H₂N, MeNH, Me₂N; R¹ = ¹⁸F) are prepared which display high in vitro binding affinity for human amyloid β plaques (K_i ≤ 10 nM). I (R¹ = ¹⁸F) are prepared by aromatic nucleophilic substitution of I [R = BocNH, BocN(Me), Me₂N; R¹ = O₂N; Boc = tert-butoxycarbonyl] with ¹⁸F-fluoride, followed by deprotection of the Boc group if required; preparation by other methods, for example cyclocondensation of diaminobenzenethiols with benzoic acids, is unsuccessful. Determination of the octanol/water partition coefficient, biodistribution studies in mice, and in vivo μPET studies in rats and a rhesus monkey show that initial brain uptake is high and brain washout is fast in normal animals. Radiometabolites are quantified in plasma and brain of mice and in monkey plasma using HPLC. Of the tested compounds, I (R = H₂N; R¹ = ¹⁸F) shows the most favorable brain kinetics in mice, rats, and a monkey; its polar plasma radiometabolites do not cross the blood-brain barrier. Preliminary results strongly suggest that I (R = H₂N; R¹ = ¹⁸F) is a promising candidate as a PET brain amyloid imaging agent. In the experiment, the researchers used many compounds, for example, 6-Nitrobenzothiazole (cas: 2942-06-5Synthetic Route of C7H4N2O2S).

6-Nitrobenzothiazole (cas: 2942-06-5) 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. Thiazole is a versatile building block for the construction and lead generation of new drug discoveries. Numerous diazole-based compounds are in clinical use as anticancer, antileukemic, antiinflammatory, antiviral, antifungal, antirheumatic, immunomodulator, and antiparasitic agents.Synthetic Route of C7H4N2O2S

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

Delayed re-endothelialization with rapamycin-coated stents is rescued by the addition of a glycogen synthase kinase-3β inhibitor was written by Ma, Xiaoli;Hibbert, Benjamin;Dhaliwal, Bharbhoor;Seibert, Tara;Chen, Yong-Xiang;Zhao, Xiaoling;O’Brien, Edward R.. And the article was included in Cardiovascular Research in 2010.COA of Formula: C12H12N4O4S This article mentions the following:

Aims: Drug-eluting stents (DESs) reduce neointima area and in-stent restenosis but delay re-endothelialization. Recently, we demonstrated that pharmacol. expansion and functional enhancement of endothelial progenitor cells (EPCs) can be achieved by treatment with a glycogen synthase kinase-3β inhibitor (GSKi)-even for feeble cells derived from coronary artery disease patients. GSKi treatment enhanced EPC adhesion via up-regulated expression of the α-4 integrin, ameliorated re-endothelialization, and reduced neointima formation in denuded murine arteries. Hence, we hypothesized that GSKi-coated stents (GSs) will enhance EPC adhesion and attenuate delayed vascular healing associated with rapamycin, a key DES agent. Methods and results: In vitro human EPCs adhered to GS with affinities that were 2×, 14×, and 13× greater than vehicle (VSs)-, rapamycin (RSs)-, and rapamycin plus GSKi (RGSs)-coated stents, resp. Stents were inserted in rabbit carotid arteries, and at 14 days, neointima area was 45 and 49% lower in GSs compared with bare metal stents (BMSs) and VSs. Moreover, RSs had a 47% larger neointima area than GSs, but RGSs reduced neointima area to a level comparable to GSs. Seven days after stenting, GSs displayed re-endothelialization that was 40, 33, and 42% greater than BMSs, VSs, and RSs, resp. Moreover, RGSs had 41% more re-endothelialization than RSs. At 14 days, the 7-day re-endothelialization patterns persisted. Conclusion: GSKi efficiently ameliorates the vascular response to stent implantation and has an important redeeming effect on the deleterious endothelial effects of rapamycin-coated stents. In the experiment, the researchers used many compounds, for example, 1-(4-Methoxybenzyl)-3-(5-nitrothiazol-2-yl)urea (cas: 487021-52-3COA of Formula: C12H12N4O4S).

1-(4-Methoxybenzyl)-3-(5-nitrothiazol-2-yl)urea (cas: 487021-52-3) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. Thiazole is a versatile building block for the construction and lead generation of new drug discoveries. Numerous diazole-based compounds are in clinical use as anticancer, antileukemic, antiinflammatory, antiviral, antifungal, antirheumatic, immunomodulator, and antiparasitic agents.COA of Formula: C12H12N4O4S

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

Peptides. XXI. Dehydrogenation of some thiazolines derived from cysteine was written by Barton, Moira A.;Kenner, G. W.;Sheppard, R. C.. And the article was included in Journal of the Chemical Society [Section] C: Organic in 1966.Name: Methyl 2-methyl-4,5-dihydrothiazole-4-carboxylate This article mentions the following:

Esters of 2-alkyl-Δ²-thiazoline-4-carboxylic acids are smoothly dehydrogenated by phenantraquinone to the corresponding thiazole derivatives Me 2-benzamidomethyl-Δ²-thiazoline-4-carboxylate is dehydrogenated only slowly by phenenthraquinone but rapidly by MnO₂. The possible application of these reactions to the detection of thiazoline rings in peptides is discussed. In the experiment, the researchers used many compounds, for example, Methyl 2-methyl-4,5-dihydrothiazole-4-carboxylate (cas: 6436-58-4Name: Methyl 2-methyl-4,5-dihydrothiazole-4-carboxylate).

Methyl 2-methyl-4,5-dihydrothiazole-4-carboxylate (cas: 6436-58-4) belongs to thiazole derivatives. The thiazole ring has been identified as a central feature of numerous natural products, perhaps the most famous example of which is epothilone. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Name: Methyl 2-methyl-4,5-dihydrothiazole-4-carboxylate

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