Tag: 200-300

Characterization of AhR agonist compounds in roadside snow was written by Muusse, Martine;Langford, Katherine;Tollefsen, Knut Erik;Cornelissen, Gerard;Haglund, Peter;Hylland, Ketil;Thomas, Kevin V.. And the article was included in Analytical and Bioanalytical Chemistry in 2012.Related Products of 1843-21-6 This article mentions the following:

Aryl hydrocarbon receptor (AhR) agonistic contaminants were identified in roadside snow samples. Snow was collected in Oslo, Norway, and compared to a background sample collected from a mountain area. The water and particulate fractions were analyzed for AhR agonists using a dioxin-responsive, chem. activated luciferase expression (CALUX) cell assay and by gas chromatog. coupled to high-resolution time-of-flight mass spectrometry with targeted anal. for polycyclic aromatic hydrocarbons (PAHs) and broad-spectrum non-target anal. The AhR agonist levels in the dissolved fractions in the roadside samples were between 15 and 387 pg/L CALUX toxic equivalent (TEQ_CALUX). An elevated AhR activity of 221 pg TEQ_CALUX per L was detected in the mountain sample. In the particle-bound fractions, the TEQ_CALUX was between 1350 and 7390 pg/L. One possible explanation for the elevated levels in the dissolved fraction of the mountain sample could be the presence of black carbon in the roadside samples, potentially adsorbing dioxin-like compounds and rendering them unavailable for AhR interaction. No polychlorinated dibenzodioxins and dibenzofurans or polychlorinated biphenyls were detected in the samples; the occurrence of PAHs, however, explained up to 9 % of the AhR agonist activity in the samples, while comprehensive two-dimensional gas chromatog. coupled to mass spectrometry GCxGC-ToF-Ms identified PAH derivatives such as polycyclic aromatic ketones and alkylated, nitrogen sulfur and oxygen PAHs in the particle fractions. The (large) discrepancy between the total and explained activity highlights the fact that there are other as yet unidentified AhR agonists present in the environment. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Related Products of 1843-21-6).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. 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.Related Products of 1843-21-6

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

Solid-phase preparation of a library based on a phenylalanine scaffold was written by Colombo, Aina;Fernandez, Joan-Carles;de la Figuera, Natalia;Fernandez-Forner, Dolors;Forns, Pilar;Albericio, Fernando. And the article was included in QSAR & Combinatorial Science in 2005.Quality Control of 2-Acetamido-4-methylthiazole-5-sulfonyl chloride This article mentions the following:

A convenient strategy (preliminary study, preprodn. and production) for the solid-phase preparation of a library using 4-iodophenylalanine as a scaffold is described. The aromatic ring was first modified via the Suzuki reaction and the amino position was subsequently derivatized into amides, sulfonamides, amines, carbamates and ureas. The scope and limitations of all of the reactions carried out in parallel are discussed. The solid-phase synthesis of a library of 315 individual compounds was attempted by using seven boronic acids and nine representative compounds from each of the following classes: carboxylic acids, sulfonyl chlorides, aldehydes, alcs. and isocyanates. Owing to the failure of the amine derivatization, 297 compounds were ultimately obtained. In the experiment, the researchers used many compounds, for example, 2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9Quality Control of 2-Acetamido-4-methylthiazole-5-sulfonyl chloride).

2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9) 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.Quality Control of 2-Acetamido-4-methylthiazole-5-sulfonyl chloride

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

Inhibition of catalase and epoxide hydrolase by the renal cystogen 2-amino-4,5-diphenylthiazole and its metabolites was written by Hjelle, J. Thomas;Guenthner, Thomas M.;Bell, Kevin;Whalen, Robert;Flouret, George;Carone, Frank A.. And the article was included in Toxicology in 1990.Application In Synthesis of 4,5-Diphenylthiazol-2-amine This article mentions the following:

Subchronic feeding of 2-amino-4,5-diphenyl-1,3-thiazole (DPT) to rats results in the development of renal cysts and has been used as a model system to study polycystic kidney disease. Because previous studies revealed changes in renal enzymes following DPT administration, a possible direct effect of DPT and its phenolic metabolites on catalase and a related enzyme, epoxide hydrolase, was examined Experiments with three in vitro systems (suspensions of rabbit renal tubules, rat kidney homogenates, and com. obtained bovine liver catalase) revealed direct inhibition of catalase activity by the diphenolic metabolite 2-amino-4,5-bis(4′-hydroxyphenyl)-1,3-thiazole (di-OH-DPT), the known renal cystogen nordihydroquaiaretic acid (NDGA), 2-amino-4-(4′-hydroxyphenyl)-5-phenyl-1,3-thiazole (4OH-DPT), and the known catalase inhibitor 2-amino-1,2,4-triazole; DPT did not inhibit catalase activity. Following oral administration to rats of the DPT congeners, 4OH-DPT caused the greatest decrease in both renal catalase and cytosolic epoxide hydrolase (cEH) activities and the shortest time to onset of cystic lesions. In vitro, mouse liver cEH activity was substantially inhibited by 4OH-DPT and diOH-DPT, and NDGA, but not by 2-amino-4-phenyl-5-(4′-hydroxyphenyl)-1,3-thiazole (5OH-DPT) or DPT itself. Microsomal epoxide hydrolase (mEH) activity was inhibited by 4OH-DPT, unaffected by DPT or diOH-DPT, and stimulated 2-fold by 5OH-DPT. Finally, mEH activity was substantially higher in samples of normal human kidney than in samples of kidney derived from a patient with autosomal recessive polycystic kidney disease; no differences were observed in cEH activity in these samples. Although the role of altered catalase and epoxide hydrolase activities in cystogenesis is unknown, DPT-induced cyst formation is associated with loss of these enzyme activities in kidney tissue. This is the first report of an in vivo diminution of cytosolic epoxide hydrolase activity by xenobiotics. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Application In Synthesis of 4,5-Diphenylthiazol-2-amine).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) 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.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Application In Synthesis of 4,5-Diphenylthiazol-2-amine

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

One pot synthesis using supported reagents system KSCN/SiO₂-RNH₃OAc/Al₂O₃: synthesis of 2-aminothiazoles and N-allylthioureas was written by Aoyama, Tadashi;Murata, Sumiko;Arai, Izumi;Araki, Natsumi;Takido, Toshio;Suzuki, Yoshitada;Kodomari, Mitsuo. And the article was included in Tetrahedron in 2006.Quality Control of 4,5-Diphenylthiazol-2-amine This article mentions the following:

A simple and efficient method has been developed for the synthesis of 2-aminothiazoles and N-allylthioureas from com. available materials in one pot by using a supported reagents system, KSCN/SiO₂-RNH₃OAc/Al₂O₃, in which α-halo ketones react first with KSCN/SiO₂ and the product, α-thiocyanatoketone, reacts with RNH₃OAc/Al₂O₃ to give the final products, 2-aminothiazoles, in good yield. Allyl bromides react with KSCN/SiO₂ and the products, allyl isothiocyanates, react with RNH₃OAc/Al₂O₃ to give N-allylthioureas. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Quality Control of 4,5-Diphenylthiazol-2-amine).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) belongs to thiazole derivatives. Thiazole is a five-membered, unsaturated, planar, π-excessive heteroaromatic containing one sulfur atom and one pyridine-type nitrogen atom at position 3 of the cyclic ring system. 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.Quality Control of 4,5-Diphenylthiazol-2-amine

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

Structure of phenyl isothiocyanate and methyl isothiocyanate sulfides was written by Paranjpe, M. G.. And the article was included in Indian Journal of Chemistry in 1968.Computed Properties of C13H10N2S This article mentions the following:

“Phenyl isothiocyanate sulfides” (I) or “methyl isothiocyanate sulfide” (II) gave the tabulated RNHCSNHR1 (III) when treated with R1NH2 in “sulfide”-amine ratios 1:>2. Reaction of I or II with R1NH2 in ratios 1:<1 90-120 min. gave, resp., R1NHCSNPhCSNHPh (IV) or R1NHCSNMeCSNHMe (V) as well as III. Refluxing CHCl3 was used with I; with II the reaction temperature was 100°, but no solvent was used (reactant “sulfide”, R1, R, m.p. of IV or V, and m.p. of III given): I, PhCH2, Ph, 129°, 148; I, cyclohexyl, Ph, 135°, 149°; I, Bu, Ph, 145°, 68°; I, sec-Bu, -, 140°, -; II, PhCH2, PhCH2, 109°, 149° [also obtained was III (R = Me), m. 78°]; II, cyclohexyl, cyclohexyl, 138°, 179°. [TABLE OMITTED] On warming IV (R1 = PhCH2) (VI) with Na plumbite solution desulfurization was observed. Boiling VI with aqueous MeNH2 afforded III (R = Ph, R1 = Me) and III (R = Ph, R1 = PhCH2). VI (1 g.), 0.8 ml. PhCH2Cl, and 20 ml. EtOH, refluxed 5 hrs. gave the 3-benzyl analog, m. 154° (EtOH), which with alc. NH4OH decomposed into III (R = Ph, R1 = PhCH2). VI (2 g.) in 40 ml. dry CHCl3, treated with Br in CHCl3 until color persisted, yielded a hydrobromide, m. 228°, which on basification yielded the free base, 2-phenylaminobenzothiazole, m.p. and mixed m.p. 158°. Thus the identity of VI was determined A mixture of 8 g. 1,3-dimethylthiourea, 8 ml. PhCH2Cl, and 50 ml. EtOH was refluxed 90 min., cooled, basified (NH4OH), and extracted with C6H6. The dried extract was kept overnight with 8 ml. CS2 and treated with 12 g. Br in 40 ml. C6H6 to give a hydrobromide, m. 236°, which on NH4OH basification gave 3.8 g. 4-methyl-5-methylimino-1,2,4-dithiazolidine-3-thione (II), m. 86° (identical with an authentic sample), which on warming with EtOH yielded the isomer (VII), m.p. and mixed m.p. 120° (Freund, 1904, 1895). Ir spectra of I and II are reported. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Computed Properties of C13H10N2S).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) belongs to thiazole derivatives. Thiazole is a five-membered, unsaturated, planar, π-excessive heteroaromatic containing one sulfur atom and one pyridine-type nitrogen atom at position 3 of the cyclic ring system. 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.Computed Properties of C13H10N2S

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

An approach to the synthesis of 4-phenyl-5-(arylimino)-Δ²-1,2,3,4-thiatriazolines was written by L’Abbe, Gerrit;Franek, Walter;Toppet, Suzanne;Delbeke, Pieter. And the article was included in Journal of Heterocyclic Chemistry in 1990.Reference of 1843-21-6 This article mentions the following:

4-Phenyl-5-arylimino-Δ²-1,2,3,4-thiatriazolines I (R = Ph, 4-MeC₆H₅) are presumably formed by reacting 5-arylaminothiatriazoles II with benzene at 50°, but decompose in situ to benzothiazole derivatives III. The reaction mechanism is discussed. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Reference of 1843-21-6).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) 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. 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.Reference of 1843-21-6

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

Sequencing Groebke-Blackburn-Bienayme and Aza-Michael Addition Reactions: A Modular Strategy for Accessing a Diverse Collection of Constrained Benzoxazepine and Imidazopyrazine Systems was written by Srinivasulu, Vunnam;Al-Marzooq, Farah;Hamad, Mohamad;Khanfar, Monther A.;Ramanathan, Mani;Soares, Nelson C.;Al-Tel, Taleb H.. And the article was included in Synthesis in 2021.Application In Synthesis of 4,5-Diphenylthiazol-2-amine This article mentions the following:

A divergent strategy that permitted the access to diversely functionalized benzoxazepinium scaffolds fused to various heterocycles was reported. The described strategy featured a one-pot combination of the Groebke-Blackburn-Bienaym reaction and an aza-Michael addition Me (E)-4-(2-formylphenoxy)but-2-enoates were utilized as central elements in this cascade. These building blocks were reacted with a variety of functionalized amino-azines and tert-Bu isocyanide under ytterbium triflate [Yb(OTf)₃] catalysis. The cascade represented a rapid, modular and atom-economic process that leaded to the construction of a diverse collection of constrained benzoxazepinium systems from a wide substrate scope. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Application In Synthesis of 4,5-Diphenylthiazol-2-amine).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) 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. 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 4,5-Diphenylthiazol-2-amine

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

2-Amino-4(or 5)-arylthiazoles. I. Ultraviolet absorption spectra of alkyl- or phenyl-substituted compounds was written by Okamiya, Jiro. And the article was included in Nippon Kagaku Zasshi in 1959.SDS of cas: 6318-74-7 This article mentions the following:

Ultraviolet absorption spectra were reported for 2-aminothiazole, 2-amino-4-methylthiazole, 2-amino-5-methylthiazole, 2-amino-4-ethyl-5-methylthiazole, 2-amino-4,5-tetramethylenethiazole, 2-amino-4,5-benzothiazole, 2-amino-4-phenylthiazole, 2-amino-5-phenyl-5-methylthiazole, 2-amino-4-(p-tolyl)thiazole, 2-amino-4-(o-tolyl)thiazole, 2-amino-4-(o-tolyl)-5-methylthiazole, m. 124°, 2-amino-4-mesitylthiazole, m. 169°, 2-amino-4-mesityl-5-methylthiazole, m. 123-4°, 2-amino-5-phenylthiazole, 2-amino-4-methyl-5-phenylthiazole, m. 171°, 2-amino-4,5-diphenylthiazole, 2-amino-4-(p-tolyl)-5-phenylthiazole, m. 179°, 2-amino-4-phenyl-5-(p-tolyl)thiazole, m. 176°, 2-amino-4,5-bis(p-tolyl)thiazole, m. 167°, 2-amino-4,5-dihydronaphtho[1,2]thiazole, 4,4′-bis(2-amino-4-thiazolyl)bibenzyl, m. 230-45° (decomposition), 2,2′-diamino-4,4′-diphenyl-5,5′-bithiazolyl (I), 1,2-bis(2-amino-4-phenyl-5-thiazolyl)ethane, m. 238°, 1,5-bis(2-amino-4-phenyl-5-thiazolyl)pentane (II), m. 165°, and 1,6-bis(2-amino-4-phenyl-5-thiazolyl)hexane. Spectra of alkyl derivative were almost the same. Spectra of 4-phenyl compounds had maximum at longer wave lengths than those of 4-phenyl-5-alkyl compounds, indicating the presence of steric hindrance. II had twice the intensity of other thiazoles, while I was weaker because of steric effects. The 5-phenyl compounds had maximum at longer wave lengths than the 4-phenyl compounds 4,5-Diaryl compounds seemed to have a fair amount of resonance (from the spectra), in spite of the expected steric hindrance. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7SDS of cas: 6318-74-7).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) belongs to thiazole derivatives. Thiazole is a five-membered, unsaturated, planar, π-excessive heteroaromatic containing one sulfur atom and one pyridine-type nitrogen atom at position 3 of the cyclic ring system. 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.SDS of cas: 6318-74-7

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

Similarities between catalase and cytosolic epoxide hydrolase was written by Guenthner, Thomas M.;Qato, Mazen;Whalen, Robert;Glomb, Sallie. And the article was included in Drug Metabolism Reviews in 1989.Synthetic Route of C15H12N2S This article mentions the following:

Cytosolic epoxide hydrolase, measured as trans-stilbene oxide hydrolase activity, was isolated and purified from human and guinea pig liver cytosol. Antiserum to the guinea pig liver preparation reacted strongly with bovine liver catalase. This lack of selectivity of the antiserum was due to catalase contamination of the epoxide hydrolase preparation It was also determined that several com. catalase preparations are contaminated with cytosolic epoxide hydrolase. The human epoxide hydrolase preparation used here contained no detectable catalase contamination, yet antiserum to this protein also cross-reacted slightly with catalase, indicating some intrinsic similarity between the 2 enzymes. It is concluded that catalase and cytosolic epoxide hydrolase contain some similar immunogenic epitopes, and it is surmised that similarities between the subunits of these 2 enzymes may lead to their partial copurifn. Functional similarities between the 2 enzymes are also demonstrated, as several compounds that inhibit catalase also inhibit cytosolic epoxide hydrolase activity in the same concentration range and rank order. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Synthetic Route of C15H12N2S).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) belongs to thiazole derivatives. Thiazole is a five-membered, unsaturated, planar, π-excessive heteroaromatic containing one sulfur atom and one pyridine-type nitrogen atom at position 3 of the cyclic ring system. 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.Synthetic Route of C15H12N2S

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

4,6-Substituted-1H-indazoles as potent IDO1/TDO dual inhibitors was written by Yang, Lingling;Chen, Yang;He, Junlin;Njoya, Emmanuel Mfotie;Chen, Jianjun;Liu, Siyan;Xie, Congqiang;Huang, Wenze;Wang, Fei;Wang, Zhouyu;Li, Yuzhi;Qian, Shan. And the article was included in Bioorganic & Medicinal Chemistry in 2019.Electric Literature of C10H14N2O4S This article mentions the following:

Indoleamine 2,3-dioxygenase 1 (IDO1) and tryptophan 2,3-dioxygenase (TDO) are constitutively overexpressed in many types of cancer cells and exert important immunosuppressive functions. In this article, a series of 4,6-substituted-1H-indazole derivatives were synthesized and evaluated the inhibitory activities against IDO1 and TDO, as well as their structure-activity relationships (SARs). Among these, compound 35(I) displayed the most IDO1 inhibitory potency with an IC₅₀ value of 0.74 μM in an enzymic assay and 1.37 μM in HeLa cells. Quant. anal. of the Western blot results indicated that I significantly decreased the INFγ-induced IDO1 expression in a concentration-dependent manner. In addition, I showed promising TDO inhibition with an IC₅₀ value of 2.93 μM in the enzymic assay and 7.54 μM in A172 cells. Moreover, I exhibited in vivo antitumor activity in the CT26 xenograft model. These findings suggest that I is a potent IDO1/TDO dual inhibitor, and has the potential to be developed for IDO1/TDO-related cancer treatment. In the experiment, the researchers used many compounds, for example, Methyl 2-Boc-aminothiazole-4-carboxylate (cas: 850429-62-8Electric Literature of C10H14N2O4S).

Methyl 2-Boc-aminothiazole-4-carboxylate (cas: 850429-62-8) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). 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.Electric Literature of C10H14N2O4S

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