Day: December 30, 2022

Photochemical rearrangements in heterocyclic series. III. Arythiazoles and arylisothiazoles isomers. Experimental results and theoretical study was written by Vernin, G.;Riou, C.;Dou, H. J. M.;Bouscasse, L.;Metzger, J.;Loridan, G.. And the article was included in Bulletin de la Societe Chimique de France in 1973.COA of Formula: C9H7NS This article mentions the following:

In the presence of I2 the photoisomerization of 3 phenylthiazoles and 3 phenylisothiazoles was selective. Five possible mechanisms from published data were examined; those best fitting the results were a valence isomerization mechanism with or without preliminary opening of weaker bonds in the 1st excited state and a mechanism involving torsion of bonds adjacent to S. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7COA of Formula: C9H7NS).

5-Phenylthiazole (cas: 1826-13-7) 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.COA of Formula: C9H7NS

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

Selective inhibition of cytosolic epoxide hydrolase activity in vitro by compounds that inhibit catalase was written by Guenthner, Thomas M.;Hjelle, J. Thomas;Whalen, Robert. And the article was included in Journal of Biochemical Toxicology in 1989.Application In Synthesis of 4,5-Diphenylthiazol-2-amine This article mentions the following:

The ability of inhibitors of catalase to affect cytosolic and microsomal epoxide hydrolase measured as enzymic trans-stilbene oxide hydrolysis and styrene oxide hydrolysis, resp., was investigated. Catalase and cytosolic epoxide hydrolase are inhibited by hydroxylated metabolites of 2-amino-4,5-diphenylthiazole (DPT). The metabolite hydroxylated on the 4-phenyl ring (4OH-DPT) and the metabolite hydroxylted on both Ph rings (4,5-DIOH-DPT) are potent inhibitors of both enzymes; the metabolite hydroxylated on the 5-Ph ring (5OH-DPT) is less potent. Unmetabolized DPT has no effect on either enzyme. 4OH-DPT inhibits, but 5OH-DPT enhances, microsomal epoxide hydrolase. 4,5-DIOH-DPT and DPT have no effect on this enzyme. Other compounds that inhibit both catalase and cytosolic epoxide hydrolase, but do not inhibit microsomal epoxide hydrolase, are nordihydroguaiaretic acid and 2-aminothiazole. Microsomal epoxide hydrolase is enhanced by 2-aminothiazole and levamisole. Thus, these inhibitors of catalase are selective epoxide hydrolase inhibitors in that they inhibit cytosolic epoxide hydrolase activity, but have either no effect on, or increase the activity of, microsomal epoxide hydrolase. Conversely, the selective cytosolic epoxide hydrolase inhibitors 4-phenylchalcone oxide and 4′-phenylchalcone oxide do not inhibit catalase, nor does trichloropropene oxide, a selective microsomal epoxide hydrolase inhibitor. 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. 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.Application In Synthesis of 4,5-Diphenylthiazol-2-amine

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

Synthesis of novel 4,5-diphenylthiazole derivatives as potential acyl-CoA : cholesterol O-acyltransferase inhibitors was written by Romeo, G.;Salerno, L.;Milla, P.;Siracusa, M.;Cattel, L.;Russo, Filippo. And the article was included in Pharmazie in 1999.Recommanded Product: 4,5-Diphenylthiazol-2-amine This article mentions the following:

Several N-(4,5-diphenylthiazol-2-yl)-N’-aryl- or -alkyl-(thio)ureas and N-(4,5-diphenylthiazol-2-yl)alkanamides were prepared as potential acyl-CoA : cholesterol O-acyltransferase (ACAT) inhibitors. Synthesis was accomplished by reaction of 2-amino-4,5-diphenylthiazole with suitable isocyanates, isothiocyanates, or acyl chlorides. Some analogs without a 5-Ph substituent or both the Ph groups in 4- and 5-position of the thiazole ring were also prepared Moreover, some bio-isosteres of the title compounds in which the thiazole ring was replaced by an imidazole were synthesized starting from 2-amino-4,5-diphenyl-1H-imidazole. The ability of synthesized compounds to inhibit ACAT was evaluated in vitro by measuring the formation of cholesteryl[¹⁴C]oleate from cholesterol and [1-¹⁴C]oleoyl-CoA in rat liver microsomes. Among the tested compounds, only some thiazole ureas were able to inhibit ACAT in a reasonable degree. N-(4,5-diphenylthiazol-2-yl)-N’-[2,6-bis(2-methylethyl)phenyl]urea and N-(4,5-diphenylthiazol-2-yl)-N’-butylurea were the most active compounds in the series showing IC₅₀ values in the low micromolar range. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Recommanded Product: 4,5-Diphenylthiazol-2-amine).

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

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

Palladium-Catalyzed Tandem Ester Dance/Decarbonylative Coupling Reactions was written by Kubo, Masayuki;Inayama, Naomi;Ota, Eisuke;Yamaguchi, Junichiro. And the article was included in Organic Letters in 2022.Computed Properties of C9H7NS This article mentions the following:

“Dance reaction” on the aromatic ring is a powerful method in organic chem. to translocate functional groups on arene scaffolds. Notably, dance reactions of halides and pseudohalides offer a unique platform for the divergent synthesis of substituted (hetero)aromatic compounds when combined with transition-metal-catalyzed coupling reactions. Herein, a tandem reaction of ester dance and decarbonylative coupling enabled by palladium catalysis is reported. In this reaction, 1,2-translocation of the ester moiety on the aromatic ring is followed by decarbonylative coupling with nucleophiles to enable the installation of a variety of nucleophiles at the position adjacent to the ester in the starting material. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Computed Properties of C9H7NS).

5-Phenylthiazole (cas: 1826-13-7) 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.Computed Properties of C9H7NS

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

Straightforward synthesis of 2-anilinobenzoxazoles and -benzothiazoles via mechanochemical ball-milling-promoted one-pot reactions was written by Zhang, Ze;Wang, Fang-Jian;Wu, Hao-Hao;Tan, Ya-Jun. And the article was included in Chemistry Letters in 2015.Related Products of 1843-21-6 This article mentions the following:

Under mechanochem. ball-milling and solvent-free conditions, a series of 2-anilinobenzoxazoles and 2-anilinobenzothiazoles were synthesized directly from the one-pot reaction of anilines, CS₂, and 2-aminophenol and -thiophenol. This protocol exhibited the free or cheap use of a cyclodesulfurization reagent, no separation of in-situ generated isothiocyanate, short reaction time and simple work-up procedure. 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. 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. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Related Products of 1843-21-6

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

Quinazolone derivatives was written by Dash, B.;Mahapatra, Prasanta K.;Mahapatra, Prasanna K.. And the article was included in Journal of the Institution of Chemists (India) in 1983.HPLC of Formula: 6318-74-7 This article mentions the following:

Thiazolylquinazolones I [R = Me, Ph; R¹ = thienyl, (un)substituted Ph; R² = H, Ph, 2-Cl₆H₄, 4-ClC₆H₄] were prepared by aminolysis of benzoxazinones II with thiazolylamines III. Arylidenequinazolones I [R = R³C₆H₄CH:CH; R¹ = (un)substituted Ph; R² = H, Ph, 2-ClC₆H₄, 4-ClC₆H₄; R³ = 2-Cl, 4-Cl] were prepared by condensing I (R = Me) with R³C₆H₄CHO. At 500 ppm I inhibited Helminthosporium sativum by 50-70%, in vitro. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7HPLC of Formula: 6318-74-7).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.HPLC of Formula: 6318-74-7

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

Reengineered tricyclic anti-cancer agents was written by Kastrinsky, David B.;Sangodkar, Jaya;Zaware, Nilesh;McClinch, Kimberly;Farrington, Caroline C.;Giannini, Heather M.;Izadmehr, Sudeh;Dhawan, Neil S.;Narla, Goutham;Ohlmeyer, Michael. And the article was included in Bioorganic & Medicinal Chemistry in 2015.Electric Literature of C6H7ClN2O3S2 This article mentions the following:

The phenothiazine and dibenzazepine tricyclics are potent neurotropic drugs with a documented but underutilized anti-cancer side effect. Reengineering these agents (TFP, CPZ, CIP) by replacing the basic amine with a neutral polar functional group (e.g., RTC-1, RTC-2) abrogated their CNS effects as demonstrated by in vitro pharmacol. assays and in vivo behavioral models. Further optimization generated several phenothiazines and dibenzazepines with improved anti-cancer potency, exemplified by RTC-5. This new lead demonstrated efficacy against a xenograft model of an EGFR driven cancer without the neurotropic effects exhibited by the parent mols. Its effects were attributed to concomitant neg. regulation of PI3K-AKT and RAS-ERK signaling. In the experiment, the researchers used many compounds, for example, 2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9Electric Literature of C6H7ClN2O3S2).

2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9) 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. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Electric Literature of C6H7ClN2O3S2

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

Design, synthesis, structure-activity relationship, and in vivo activity of azabicyclic aryl amides as α7 nicotinic acetylcholine receptor agonists was written by Walker, Daniel P.;Wishka, Donn G.;Piotrowski, David W.;Jia, Shaojuan;Reitz, Steven C.;Yates, Karen M.;Myers, Jason K.;Vetman, Tatiana N.;Margolis, Brandon J.;Jacobsen, E. Jon;Acker, Brad A.;Groppi, Vincent E.;Wolfe, Mark L.;Thornburgh, Bruce A.;Tinholt, Paula M.;Cortes-Burgos, Luz A.;Walters, Rodney R.;Hester, Matthew R.;Seest, Eric P.;Dolak, Lester A.;Han, Fusen;Olson, Barbara A.;Fitzgerald, Laura;Staton, Brian A.;Raub, Thomas J.;Hajos, Mihaly;Hoffmann, William E.;Li, Kai S.;Higdon, Nicole R.;Wall, Theron M.;Hurst, Raymond S.;Wong, Erik H. F.;Rogers, Bruce N.. And the article was included in Bioorganic & Medicinal Chemistry in 2006.Safety of Benzothiazole-5-carboxylic acid This article mentions the following:

A novel set of azabicyclic aryl amides have been identified as potent and selective agonists of the α7 nAChR. A two-pronged approach was taken to improve the potential hERG liability of previously disclosed α7 nAChR agonist, PNU-282,987, while maintaining the compound’s other desirable pharmacol. properties. The first approach involved further exploration of the aryl carboxylic acid fragment of PNU-282,987, while the second approach focused on modification of the azabicyclic amine portion of PNU-282,987. The best compounds from each series are characterized by rapid brain penetration, good oral bioavailability in rat, and demonstrate in vivo efficacy in a rat P50 auditory sensory gating assay. At least one analog from each series shows an improved hERG safety profile over PNU-282,987. In the experiment, the researchers used many compounds, for example, Benzothiazole-5-carboxylic acid (cas: 68867-17-4Safety of Benzothiazole-5-carboxylic acid).

Benzothiazole-5-carboxylic acid (cas: 68867-17-4) 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.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Safety of Benzothiazole-5-carboxylic acid

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

A copper-mediated cross-coupling approach for the synthesis of 3-heteroaryl quinolone and related analogues was written by Shin, Sanghye;Kim, Yechan;Kim, Kiho;Hong, Sungwoo. And the article was included in Organic & Biomolecular Chemistry in 2014.Related Products of 1826-13-7 This article mentions the following:

An efficient and practical method for the direct cross-coupling between quinolones and a range of azoles was developed via copper-mediated C-H functionalization. This synthetic strategy provides a convenient access to a variety of C3-heteroaryl quinolones, quinolinone, nalidixic acid, uracil, pyridone, and chromone derivatives, which are prominent structural motifs in many biol. active compounds E.g., in presence of CuI and LiOCMe₃ in 1,4-dioxane under N₂ at 110 °C, coupling of 1-benzyl-3-iodo-4-quinolone with benzothiazole gave 80% 3-heteroaryl quinolone derivative (I). In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Related Products of 1826-13-7).

5-Phenylthiazole (cas: 1826-13-7) 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.Related Products of 1826-13-7

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

Discovery of N-(4-aryl-5-aryloxy-thiazol-2-yl)-amides as potent RORγt inverse agonists was written by Wang, Yonghui;Yang, Ting;Liu, Qian;Ma, Yingli;Yang, Liuqing;Zhou, Ling;Xiang, Zhijun;Cheng, Ziqiang;Lu, Sijie;Orband-Miller, Lisa A.;Zhang, Wei;Wu, Qianqian;Zhang, Kathleen;Li, Yi;Xiang, Jia-Ning;Elliott, John D.;Leung, Stewart;Ren, Feng;Lin, Xichen. And the article was included in Bioorganic & Medicinal Chemistry in 2015.Formula: C15H12N2S This article mentions the following:

A novel series of N-(4-aryl-5-aryloxy-thiazol-2-yl)-amides as RORγt inverse agonists was discovered. Binding mode anal. of a RORγt partial agonist (2c) revealed by co-crystal structure in RORγt LBD suggests that the inverse agonists do not directly interfere with the interaction between H12 and the RORγt LBD. Detailed SAR exploration led to identification of potent RORγt inverse agonists such as 3m with a pIC₅₀ of 8.0. Selected compounds in the series showed reasonable activity in Th17 cell differentiation assay as well as low intrinsic clearance in mouse liver microsomes. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Formula: C15H12N2S).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) 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. 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: C15H12N2S

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