Day: February 22, 2023

Subtype determination of presynaptic α₂-autoreceptors in the rabbit pulmonary artery and human saphenous vein was written by Molderings, G. J.;Gothert, M.. And the article was included in Naunyn-Schmiedeberg’s Archives of Pharmacology in 1995.Category: thiazole This article mentions the following:

The pharmacol. properties of the presynaptic α₂-autoreceptors mediating inhibition of noradrenaline release were investigated in human saphenous vein and rabbit pulmonary artery. Segments of these blood vessels were incubated with [³H]noradrenaline and subsequently superfused with physiol. salt solution containing uptake₁ and uptake₂ blockers. The potencies of α₂-adrenoceptor antagonists in facilitating (pEC₄₀) the elec. (2Hz) evoked tritium overflow were determined The order of potency and potency ratios of α₂-adrenoceptor antagonists in facilitating (pEC₄₀) the elec. (2Hz) evoked tritium overflow were determined The order of potency and potency rations of α₂-adrenoceptor antagonists obtained in the experiments were compared with the corresponding order of affinity and affinity rations from radioligand binding studies in tissues and cells expressing only 1 of the α₂-adrenoceptor subtypes. In the rabbit pulmonary artery, oxymetazoline was a highly potent agonist at presynaptic α₂-adrenoceptors, as reflected by its ability to inhibit at low concentrations the elec. evoked tritium overflow. However, in the human saphenous vein oxymetazoline behaved as a partial agonist, which, interaction experiments with the α₂-adrenoceptor agonist B-HT 920 (2-amino-6-allyl-5-6,7,8-tetrahydro-4H-thiazolo-[4,5-d]-azephine), exhibited high potency in antagonizing the inhibitory effect of the latter drug on tritium overflow. Prazosin given alone at concentrations ≤1 μM did not affect tritium overflow. The data obtained with oxymetazoline and prazosin make it very improbable that the α₂-autoreceptors on the sympathetic nerves in both tissues are of the α_2B– or α_2C– subtype. In both blood vessels, rauwolscine given alone was highly potent in facilitating the elec. evoked overflow. In agreement with this, rauwolscine exhibited high potency in antagonizing the inhibitory effect of oxymetazoline on tritium overflow in the rabbit pulmonary artery and of B-HT 920 in the human saphenous vein. The ratio phentolamine/rauwolscine calculated from their potencies in increasing the elec. evoked tritium overflow was also used to discriminate between the various a₂-adrenoceptor subtypes. Comparisons of this potency ratio with the corresponding affinity ratios for α₂-adrenergic binding sites on HT 29 cells, human platelets, bovine pineal gland, rat submaxillary gland, and cell lines transfected with the human α₂ genes indicates that in the rabbit pulmonary artery and human saphenous vein the pharmacol. characteristics of the autoreceptors conform best to those of α_2A-adrenoceptors. Finally, in both blood vessels the potencies of the antagonists BDF 6143 (4-chloro-2-(2-imidazolin-2-ylamino)-isoindoline), rauwolscine, corynanthine, phentolamine, idazoxan, SKF 104078 (6-chloro-9-[(3-methyl-2-butenyl) oxyl]-3-methyl-1-1H-2,3,4,5-tetrahydro-3-benzazepine), and/or tolazoline in facilitating evoked noradrenaline, and/or tolazoline in facilitating evoked noradrenaline release was determined The potencies of these drugs which can discriminate between α_2A– and α_2D-adrenoceptors (but not between these and α_2B/_2C-adrenoceptors) were correlated significantly with their affinities for α_2A, but not α_2D, sites in radioligand binding studies. Apparently, the sympathetic nerves of the human saphenous vein and rabbit pulmonary artery are endowed with α₂-autoreceptors of the α_2A subtype. In the experiment, the researchers used many compounds, for example, 6-Allyl-5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepin-2-amine dihydrochloride (cas: 36085-73-1Category: thiazole).

6-Allyl-5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepin-2-amine dihydrochloride (cas: 36085-73-1) 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.Category: thiazole

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

Charge Transport Across Dynamic Covalent Chemical Bridges was written by Miao, Zelin;Quainoo, Timothy;Czyszczon-Burton, Thomas M.;Rotthowe, Nils;Parr, Joseph M.;Liu, Zhen-Fei;Inkpen, Michael S.. And the article was included in Nano Letters in 2022.Formula: C7H9NS This article mentions the following:

Relationships between chem. structure and conductivity in ordered polymers (OPs) are difficult to probe using bulk samples. We propose that conductance measurements of appropriate mol.-scale models can reveal trends in electronic coupling(s) between repeat units that may help inform OP design. Here, we apply the scanning tunneling microscope-based break-junction (STM-BJ) method to study transport through single-mols. comprising OP-relevant imine, imidazole, diazaborole, and boronate ester dynamic covalent chem. bridges. Notably, solution-stable boron-based compounds dissociate in situ unless measured under a rigorously inert glovebox atm. We find that junction conductance neg. correlates with the electronegativity difference between bridge atoms, and corroborative first-principles calculations further reveal a different nodal structure in the transmission eigenchannels of boronate ester junctions. This work reaffirms expectations that highly polarized bridge motifs represent poor choices for the construction of OPs with high through-bond conductivity and underscores the utility of glovebox STM-BJ instrumentation for studies of air-sensitive materials. In the experiment, the researchers used many compounds, for example, 4-(Methylthio)aniline (cas: 104-96-1Formula: C7H9NS).

4-(Methylthio)aniline (cas: 104-96-1) 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.Formula: C7H9NS

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

Determination of 2-[bis-(N-acetylsulfanilyl)]aminothiazole in the commercial product was written by Bellen, Z.;Mroczkowska, Z.. And the article was included in Chemia Analityczna (Warsaw, Poland) in 1956.Product Details of 127-76-4 This article mentions the following:

The method consists of ammonolysis of the product by heating with concentrated NH₃ and EtOH and by double evaporation of EtOH and NH₃. Acetyl sulfathiazole is determined by potentiometric titration in H₂OMe₂CO mixture (4:1) with standard NaOH solution The determination of impurities in the sample is analogous. The results are tabulated and given in graphs. The method gave good results for pure as well as for com. samples. In the experiment, the researchers used many compounds, for example, N-(4-(N-(Thiazol-2-yl)sulfamoyl)phenyl)acetamide (cas: 127-76-4Product Details of 127-76-4).

N-(4-(N-(Thiazol-2-yl)sulfamoyl)phenyl)acetamide (cas: 127-76-4) 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 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.Product Details of 127-76-4

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

Evaluating aryl esters as bench-stable C(1)-ammonium enolate precursors in catalytic, enantioselective Michael addition-lactonizations was written by Young, Claire M.;Taylor, James E.;Smith, Andrew D.. And the article was included in Organic & Biomolecular Chemistry in 2019.Reference of 16595-80-5 This article mentions the following:

An evaluation of a range of aryl, alkyl and vinyl esters as prospective C(1)-ammonium enolate precursors in enantioselective Michael addition-lactonization processes with (E)-trifluoromethylenones using isothiourea catalysis was reported. Electron deficient aryl esters were required for reactivity, with 2,4,6-trichlorophenyl esters providing optimal product yields. Catalyst screening showed that tetramisole was the most effective isothiourea catalyst, giving the desired dihydropyranone products I [Ar = Ph, 4-MeC₆H₄, 4-F₃CC₆H₄; Ar¹ = Ph] in excellent yield and stereoselectivity (up to 90 : 10 dr and 98 : 2 er). The scope and limitations of this process were evaluated, with a range of keto ester products II [Ar¹ = Ph, 2-furyl, 4-MeC₆H₄, 3-MeOC₆H₄, 4-BrC₆H₄] being generated after ring-opening with MeOH to give stereodefined dihydropyranones with excellent stereocontrol (10 examples, typically ∼90 : 10 dr and >95 : 5 er). In the experiment, the researchers used many compounds, for example, (S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole hydrochloride (cas: 16595-80-5Reference of 16595-80-5).

(S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole hydrochloride (cas: 16595-80-5) 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. 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.Reference of 16595-80-5

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