Month: February 2023

Electron-Deficient Polycyclic π-System Fused with Multiple B←N Coordinate Bonds was written by Cao, Yirui;Zhu, Congzhi;Barlog, Maciej;Barker, Kayla P.;Ji, Xiaozhou;Kalin, Alexander J.;Al-Hashimi, Mohammed;Fang, Lei. And the article was included in Journal of Organic Chemistry in 2021.Product Details of 121359-48-6 This article mentions the following:

An extensive polycyclic π-system with 23 fused rings is designed and synthesized via a highly efficient borylation reaction, in which four B-N covalent bonds and four B ← N coordinate bonds are formed in one pot. B ← N coordinate bonds not only lock the backbone into a near-coplanar conformation, but also decrease the LUMO energy level to around -3.82 eV, demonstrating the dual utility of this strategy for the synthesis of extensive rigid polycyclic mols. and the development of n-type conjugated materials for organic electronics and organic photovoltaics. 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. 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. 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.Product Details of 121359-48-6

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

Activation of Free Fatty Acid Receptor 4 Affects Intestinal Inflammation and Improves Colon Permeability in Mice was written by Salaga, Maciej;Bartoszek, Adrian;Binienda, Agata;Krajewska, Julia B.;Fabisiak, Adam;Mosinska, Paula;Dziedziczak, Katarzyna;Niewinna, Karolina;Talar, Marcin;Tarasiuk, Aleksandra;Kordek, Radzislaw;Fichna, Jakub. And the article was included in Nutrients in 2021.Safety of 2-(4-Chlorophenyl)-3-methyl-N-(thiazol-2-yl)butanamide This article mentions the following:

Diet is considered an important trigger in inflammatory bowel diseases (IBD), as feeding habits can affect intestinal permeability and clearance of bacterial antigens, consequently influencing the immune system. Free fatty acid receptors (FFARs), expressed on the intestinal epithelial cells, belong to the family of luminal-facing receptors that are responsive to nutrients. The objective of this study was to characterize the anti-inflammatory activity and the effect on intestinal barrier function of synthetic FFAR agonists in mouse models of colitis. Therapeutic activity of GW9508 (FFAR1 agonist), 4-CMTB (FFAR2 agonist), AR420626 (FFAR3 agonist), and GSK137647 (FFAR4 agonist) was investigated in two models of semi-chronic colitis: induced by trinitrobenzenesulfonic acid (TNBS), mimicking Crohn’s disease, as well as induced by dextran sulfate sodium (DSS), which recapitulates ulcerative colitis in humans. Moreover, we assessed the influence of FFARs agonists on epithelial ion transport and measured the ion flow stimulated by forskolin and veratridine. Administration of FFAR4 agonist GSK137647 attenuated both TNBS-induced and DSS-induced colitis in mice, as indicated by macroscopic parameters and myeloperoxidase activity. The action of FFAR4 agonist GSK137647 was significantly blocked by pretreatment with selective FFAR4 antagonist AH7614. Moreover, FFAR1 and FFAR4 agonists reversed the increase in the colon permeability caused by inflammation. FFAR4 restored the tight junction genes expression in mouse colon. This is the first evaluation of the anti-inflammatory activity of selective FFAR agonists, showing that pharmacol. intervention targeting FFAR4, which is a sensor of medium and long chain fatty acids, attenuates intestinal inflammation. In the experiment, the researchers used many compounds, for example, 2-(4-Chlorophenyl)-3-methyl-N-(thiazol-2-yl)butanamide (cas: 300851-67-6Safety of 2-(4-Chlorophenyl)-3-methyl-N-(thiazol-2-yl)butanamide).

2-(4-Chlorophenyl)-3-methyl-N-(thiazol-2-yl)butanamide (cas: 300851-67-6) 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. There are numerous natural products that possess a thiazole ring with broad pharmacological activities. Thiamine, also known as vitamin B1, possesses a thiazole ring linked with 2-methylpyrimidine-4-amine as hydrochloride salt.Safety of 2-(4-Chlorophenyl)-3-methyl-N-(thiazol-2-yl)butanamide

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

Heteroarylation of Sulfenate Ions In Situ Generated from β-Sulfinyl Esters under Transition-Metal-Free Conditions was written by Pilathottathil, Fathima;Unnikrishnan, Sreelakshmi;Kaliyamoorthy, Alagiri. And the article was included in Journal of Organic Chemistry in 2022.Quality Control of 2-Chlorobenzothiazole This article mentions the following:

Heteroaryl sulfoxides are an integral part of several bioactive mols. and pharmaceuticals. A transition-metal-free route for the direct sulfinylation of 2-halobenzothiazoles and 2-halobenzimidazoles using β-sulfinyl esters as the source of the sulfenate ion in the presence of a Bronsted base such as LiOtBu, and the corresponding heteroaryl sulfoxides were isolated in yields of 30 to 94% have been described. Moreover, a plausible concerted nucleophilic aromatic substitution (cS_NAr) pathway for the direct incorporation of sulfinyl functionality into the 2-haloheteroarenes has been hypothesized. In the experiment, the researchers used many compounds, for example, 2-Chlorobenzothiazole (cas: 615-20-3Quality Control of 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. 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.Quality Control of 2-Chlorobenzothiazole

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

Micellar electrokinetic chromatography method development for determination of impurities in Ritonavir was written by Carvalho, Alexandre Zatkovskis;El-Attug, Mohamed Nouri;Zayed, Sahar Ebrahem;Van Hove, Els;Van Duppen, Joost;Hoogmartens, Jos;Van Schepdael, Ann. And the article was included in Journal of Pharmaceutical and Biomedical Analysis in 2010.HPLC of Formula: 154212-61-0 This article mentions the following:

Ritonavir is a synthetic peptidomimetic human immunodeficiency virus (HIV) protease inhibitor employed in the treatment of AIDS since 1996. Synthetic precursors are potential impurities in the final product. In the present work a micellar electrokinetic chromatog. (MEKC) method for the separation of Ritonavir from three available synthetic precursors was developed. The optimized separation is performed in a background electrolyte composed of sodium tetraborate (pH 9.6; 15 mM) containing sodium dodecylsulfate (30 mM) and acetonitrile (18%, volume/volume). Mass spectrometry was used to confirm the identity of the tested substances. Good repeatability was observed for migration time (RSD about 0.4%) and peak area (RSD about 0.8%). The limits of detection (LOD) obtained allow the determination of two of the impurities at levels as low as 0.005% m/m, and one at a level of 0.3% m/m. In the experiment, the researchers used many compounds, for example, N-[2-Isopropylthiazol-4-ylmethyl(methyl)carbamoyl]-L-valine (cas: 154212-61-0HPLC of Formula: 154212-61-0).

N-[2-Isopropylthiazol-4-ylmethyl(methyl)carbamoyl]-L-valine (cas: 154212-61-0) 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. 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.HPLC of Formula: 154212-61-0

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

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