Day: February 22, 2023

Synthesis and in silico analysis of some new N-phosphorylated 1,2,4-triazole derivatives as potential mycocidal agents was written by Gumber, Khushbu;Sidhu, Anjali;Sharma, Vineet K.. And the article was included in Indian Journal of Heterocyclic Chemistry in 2017.Safety of 6-Fluorobenzo[d]thiazole-2(3H)-thione This article mentions the following:

Ten new biheterocyclic compounds were synthesized by two-step reaction protocol via formation of intermediate Ph phosphorodichloridate, followed by addition of triazole and the addnl. heterocyclic substituent to obtain the final product. The in vitro mycocidal potential of novel synthesized N-phosphorylated 1,2,4-triazole derivatives were examined on phytopathogens, namely, Blumeria graminis tritici, Puccinia striiformis, Puccinia triticina, and Ustilago tritici. Structure elucidation of the compounds was made on the basis of elemental anal., Fourier transform IR, ¹H NMR, and ³¹P NMR spectral data. Most of the compounds with addnl. thiazole/benzothiazole moieties inflicted appreciable potential, comparable to standards and in silico anal. rationale the in vitro antifungal potential of the test compounds In the experiment, the researchers used many compounds, for example, 6-Fluorobenzo[d]thiazole-2(3H)-thione (cas: 80087-71-4Safety of 6-Fluorobenzo[d]thiazole-2(3H)-thione).

6-Fluorobenzo[d]thiazole-2(3H)-thione (cas: 80087-71-4) 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.Safety of 6-Fluorobenzo[d]thiazole-2(3H)-thione

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

Hexahydrophthalimide-benzothiazole hybrids as a new class of protoporphyrinogen oxidase inhibitors: synthesis, structure-activity relationship, and DFT calculations was written by Wu, Qiong-You;Jiang, Li-Li;Yang, Sheng-Gang;Zuo, Yang;Wang, Zhi-Fang;Xi, Zhen;Yang, Guang-Fu. And the article was included in New Journal of Chemistry in 2014.Name: 6-Fluorobenzo[d]thiazole-2(3H)-thione This article mentions the following:

Protoporphyrinogen oxidase (PPO, EC 1.3.3.4) has attracted continuous interest during the last few decades not only because of its unique biochem. characteristics but also because of its biomedical significance. As a continuation of our research work on the development of new PPO inhibitors, N-(benzothiazol-5-yl)-hexahydro-2H-isoindole-1,3-dithione (1a-j) and N-(benzothiazol-5-yl)-octahydro-3-thioxoisoindol-1-one derivatives (2a-i) were designed and synthesized. These newly prepared compounds were characterized by elemental analyses, ¹H NMR and ESI-MS spectroscopy. The in vitro assay indicated that these compounds displayed good inhibition activity against human PPO (hPPO) with K_i values ranging from 0.38 渭M to 6.83 渭M. Notably, most of the monothionated products (1a-j) displayed a higher or comparable PPO-inhibition activity compared with the com. control sulfentrazone. The comparison of the dihedral angles of the representative compound with that of acifluorfen (ACF) complexed with hPPO clearly indicated that the dihedral angle between the thionyl amide or carbonyl amide ring and the benzothiazole ring was closely related to the variation of the PPO inhibition activity of different types of inhibitors. In the experiment, the researchers used many compounds, for example, 6-Fluorobenzo[d]thiazole-2(3H)-thione (cas: 80087-71-4Name: 6-Fluorobenzo[d]thiazole-2(3H)-thione).

6-Fluorobenzo[d]thiazole-2(3H)-thione (cas: 80087-71-4) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). 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.Name: 6-Fluorobenzo[d]thiazole-2(3H)-thione

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

Preparation of Novel Chiral Stationary Phases Based on the Chiral Porous Organic Cage by Thiol-ene Click Chemistry for Enantioseparation in HPLC was written by Wang, Ying;Chen, Ji-Kai;Xiong, Ling-Xiao;Wang, Bang-Jin;Xie, Sheng-Ming;Zhang, Jun-Hui;Yuan, Li-Ming. And the article was included in Analytical Chemistry (Washington, DC, United States) in 2022.COA of Formula: C11H12N2S This article mentions the following:

Porous organic cages (POCs) are an emerging class of porous materials that have aroused considerable research interest because of their unique characteristics, including good solubility and a well-defined intrinsic cavity. However, there have so far been no reports of chiral POCs as chiral stationary phases (CSPs) for enantioseparation by high-performance liquid chromatog. (HPLC). Herein, we report the first immobilization of a chiral POC, NC1-R, on thiol-functionalized silica using a mild thiol-ene click reaction to prepare novel CSPs for HPLC. Two CSPs (CSP-1 and CSP-2) with different spacers have been prepared CSP-1, with a cationic imidazolium spacer, exhibited excellent enantioselectivity for the resolution of various racemates. Twenty-three and 12 racemic compounds or chiral drugs were well enantiosepd. on the CSP-1-packed column under normal-phase and reversed-phase conditions, resp., including alcs., diols, esters, ethers, ketones, epoxides, organic acids, and amines. In contrast, chiral resolution using CSP-2 (without a cationic imidazolium spacer)-packed column B was inferior to that of column A, demonstrating the important role of the cationic imidazolium spacer for chiral separation The chiral separation capability of column A was also compared with that of two most popular com. chiral columns, Chiralpak AD-H and Chiralcel OD-H, which exhibits good chiral recognition complementarity with the two com. chiral columns. In addition, five positional isomers dinitrobenzene, nitroaniline, chloroaniline, bromoaniline, and iodoaniline were also well separated on column A. The effects of temperature, mobile phase composition, and injected analyte mass for separation on column A were investigated. Column A also showed good stability and reproducibility after repeated injections. This work demonstrates that chiral POCs are promising chiral materials for HPLC enantioseparation In the experiment, the researchers used many compounds, for example, (S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole (cas: 14769-73-4COA of Formula: C11H12N2S).

(S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole (cas: 14769-73-4) 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. 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.COA of Formula: C11H12N2S

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

The preparation of thiazole-4- and -5-carboxylates, and an infrared study of their rotational isomers was written by Barton, Anne;Breukelman, Stephen P.;Kaye, Perry T.;Meakins, G. Denis;Morgan, David J.. And the article was included in Journal of the Chemical Society, Perkin Transactions 1 in 1982.Electric Literature of C8H10ClNO2S This article mentions the following:

A general procedure is reported for the preparation of thiazole-4- and -5-carboxylates containing alkyl and halo substituents. Treatment of Me₂CHCHO and Cl₂CHCO₂Me with NaOMe in Et₂O at 0掳, followed by addition of (H₂N)₂CS and 4 h reflux in MeOH gave the aminothiazole I. The thiazole II was prepared by treatment of EtO₂CCHBrCOCMe₃ with (H₂N)₂CS in refluxing EtOH for 1 h, followed by deamination with NaNO₂-H₃PO₂. Both series of esters show IR carbonyl doublets caused by rotational isomerism; the more intense absorptions of the 4-carboxylates are at lower wave number, whereas those of the 5-carboxylates are the higher wave number component. In both series, the stronger bands arise from the thermochem. more stable forms. For the 4-carboxylates, these forms are the carbonyl O,S–syn-s-trans-rotamers. In the experiment, the researchers used many compounds, for example, Methyl 2-chloro-5-isopropylthiazole-4-carboxylate (cas: 81569-27-9Electric Literature of C8H10ClNO2S).

Methyl 2-chloro-5-isopropylthiazole-4-carboxylate (cas: 81569-27-9) 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 未 7.27 and 8.77 ppm (C2 and C4), indicating diamagnetic ring current. 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.Electric Literature of C8H10ClNO2S

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

Electron-Deficient Polycyclic 蟺-System Fused with Multiple B鈫怤 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 蟺-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 鈫?N coordinate bonds are formed in one pot. B 鈫?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 尾-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 尾-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 伪₂-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 伪₂-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 伪₂-adrenoceptor antagonists in facilitating (pEC₄₀) the elec. (2Hz) evoked tritium overflow were determined The order of potency and potency ratios of 伪₂-adrenoceptor antagonists in facilitating (pEC₄₀) the elec. (2Hz) evoked tritium overflow were determined The order of potency and potency rations of 伪₂-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 伪₂-adrenoceptor subtypes. In the rabbit pulmonary artery, oxymetazoline was a highly potent agonist at presynaptic 伪₂-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 伪₂-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 鈮? 渭M did not affect tritium overflow. The data obtained with oxymetazoline and prazosin make it very improbable that the 伪₂-autoreceptors on the sympathetic nerves in both tissues are of the 伪_2B– or 伪_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 伪₂-adrenergic binding sites on HT 29 cells, human platelets, bovine pineal gland, rat submaxillary gland, and cell lines transfected with the human 伪₂ genes indicates that in the rabbit pulmonary artery and human saphenous vein the pharmacol. characteristics of the autoreceptors conform best to those of 伪_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 伪_2A– and 伪_2D-adrenoceptors (but not between these and 伪_2B/_2C-adrenoceptors) were correlated significantly with their affinities for 伪_2A, but not 伪_2D, sites in radioligand binding studies. Apparently, the sympathetic nerves of the human saphenous vein and rabbit pulmonary artery are endowed with 伪₂-autoreceptors of the 伪_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 掳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 掳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