Day: February 22, 2023

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 尾 plaques (K_i 鈮?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 渭PET 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-3尾 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-3尾 inhibitor (GSKi)-even for feeble cells derived from coronary artery disease patients. GSKi treatment enhanced EPC adhesion via up-regulated expression of the 伪-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脳, 14脳, and 13脳 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-螖²-thiazoline-4-carboxylic acids are smoothly dehydrogenated by phenantraquinone to the corresponding thiazole derivatives Me 2-benzamidomethyl-螖²-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

One-Pot Reductive Methylation of Nitro- and Amino-Substituted (Hetero)Aromatics with DMSO/HCOOH: Concise Synthesis of Fluorescent Dimethylamino-Functionalized Bibenzothiazole Ligands with Tunable Emission Color upon Complexation was written by Osusky, Patrik;Smolicek, Maros;Nociarova, Jela;Rakovsky, Erik;Hrobarik, Peter. And the article was included in Journal of Organic Chemistry in 2022.Formula: C7H4N2O2S This article mentions the following:

One-pot reductive N,N-dimethylation of suitable nitro- and amino-substituted (hetero)arenes e.g., 6-nitrobenzothiazole can be achieved using a DMSO/HCOOH/Et₃N system acting as a low-cost but efficient reducing and methylating agent. The transformation of heteroaryl-amines can be accelerated by using DMSO/oxalyl chloride or chloromethyl sulfide as the source of active CH₃SCH₂⁺ species, while the exclusion of HCOOH in the initial stage of the reaction allows avoiding N-formamides as resting intermediates. The developed procedures are applicable in multigram-scale synthesis, and because of the lower electrophilicity of CH₃SCH₂⁺, they also work in pathol. cases, where common methylating agents provide N,N-dimethylated products e.g., I in no yield or inferior yields due to concomitant side reactions. The method is particularly useful in one-pot reductive transformation of 2-H-nitrobenzazoles to corresponding N,N-dimethylamino-substituted heteroarenes. These, upon Cu(II)-catalyzed oxidative homocoupling, afford 2,2′-bibenzazoles II (Z = S, NMe; R¹ = H, Me; R² = H, N(Me)₂; R³ = H, N(Me)₂) substituted with dimethylamino groups as charge-transfer N,N ligands with intensive absorption/emission in the visible region. The fluorescence of NMe₂-functionalized bibenzothiazoles II remains intensive even upon complexation with ZnCl₂, while emission maxima are bathochromically shifted from the green/yellow to orange/red spectral region, making these small-mol. fluorophores, exhibiting large emission quantum yields and Stokes shifts, an attractive platform for the construction of various functional dyes and light-harvesting materials with tunable emission color upon complexation. In the experiment, the researchers used many compounds, for example, 6-Nitrobenzothiazole (cas: 2942-06-5Formula: C7H4N2O2S).

6-Nitrobenzothiazole (cas: 2942-06-5) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. 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.Formula: C7H4N2O2S

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

Microwave-assisted synthesis of 2-amino-4-substituted phenyl-thiazole was written by Rahatgaonkar, Anjali;Rathod, A.. And the article was included in Asian Journal of Chemistry in 2006.SDS of cas: 57634-55-6 This article mentions the following:

The reaction time needed to synthesize substituted 2-amino-4-phenyl-thiazole was substantially reduced from hours to minutes by microwave irradiation Microwave assisted techniques have many advantages, i.e., very rapid reactions, low energy consumption and safe operation, high yield and less time. In the experiment, the researchers used many compounds, for example, 4-(2-Amino-4-thiazolyl)phenol (cas: 57634-55-6SDS of cas: 57634-55-6).

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. 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.SDS of cas: 57634-55-6

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

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