Category: thiazole

Vicinal diaryl azole-based urea derivatives as potential cholesterol lowering agents acting through inhibition of SOAT enzymes was written by Pal, Palash;Gandhi, Hardik P.;Kanhed, Ashish M.;Patel, Nirali R.;Mankadia, Niraj N.;Baldha, Satish N.;Barmade, Mahesh A.;Murumkar, Prashant R.;Yadav, Mange Ram. And the article was included in European Journal of Medicinal Chemistry in 2017.HPLC of Formula: 6318-74-7 This article mentions the following:

A novel series of vicinal diaryl azole-urea derivatives were synthesized and evaluated for their potential to inhibit SOAT enzyme. Among the reported compounds, 1-butyl-3-(4-(2-methyl-4-(p-tolyl)thiazol-5-yl)phenyl)urea emerged as the most potent compound with an IC₅₀ value of 2.43 μM. In polaxamer-407 induced lipoprotein lipase inhibition model, 1-butyl-3-(4-(2-methyl-4-(p-tolyl)thiazol-5-yl)phenyl)urea reduced triglyceride turnover in vivo. 1-Butyl-3-(4-(2-methyl-4-(p-tolyl)thiazol-5-yl)phenyl)urea also showed dose-dependent prevention of serum total cholesterol and prevention of LDL-C elevation at a dose of 30 mg/kg. Furthermore, 1-butyl-3-(4-(2-methyl-4-(p-tolyl)thiazol-5-yl)phenyl)urea showed potential to stop falling levels of serum HDL-C dose-dependently and improved the atherogenic index. Effect of 1-butyl-3-(4-(2-methyl-4-(p-tolyl)thiazol-5-yl)phenyl)urea on body weight, plaque formation and development of atherogenic lesions were studied. Toxicol. study of 1-butyl-3-(4-(2-methyl-4-(p-tolyl)thiazol-5-yl)phenyl)urea indicated that at a dose of 2000 mg/kg, 1-butyl-3-(4-(2-methyl-4-(p-tolyl)thiazol-5-yl)phenyl)urea was devoid of any signs of toxicity or mortality. 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. 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.HPLC of Formula: 6318-74-7

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

Synthesis and antiplatelet activity of 2-amino-4,5-diphenylthiazole derivatives was written by Inoue, Hisataka;Ikesue, Koichi;Taniguchi, Yasuaki. And the article was included in Yakugaku Zasshi in 1995.Product Details of 6318-74-7 This article mentions the following:

A series of 4,5-diphenylthiazoles containing morpholinoalkyl amino groups at the 2 position was synthesized and their anti-platelet activities were evaluated. The inhibitory effects of the compounds in which Ph groups at the 4 position were substituted by methoxy groups were more potent than those of aspirin and ibuprofen on the collagen-induced rabbit platelet aggregation. These compounds were also shown to have potent efficacies on the arachidonic acid-induced platelet aggregation. These compounds did not affect the ADP-induced platelet aggregation similarly to non-steroidal anti-inflammatory agents. Moreover, their efficacies on the inhibition of prostaglandin synthesis were more potent than that of ibuprofen. Therefore, the authors thought that 2-(morpholinoalkyl)amino-4,5-diphenylthiazoles, in spite of their basic properties, inhibited the platelet aggregation based on cyclooxygenase. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Product Details of 6318-74-7).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). 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 6318-74-7

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

Lanthanide-catalyzed cyclocarbonylation and cyclothiocarbonylation: a facile synthesis of benzannulated 1,3-diheteroatom five- and six-membered heterocycles was written by Jing, Yu Feng;Liu, Rui Ting;Lin, Yang Hui;Zhou, Xi Geng. And the article was included in Science China: Chemistry in 2014.HPLC of Formula: 1843-21-6 This article mentions the following:

La[N(SiMe₃)₂]₃ proved to be an efficient catalytic system for the cyclocarbonylation of 1,2-disubstituted benzenes with isocyanates. Aryl/alkyl isocyanates were reacted with o-phenylenediamine, o-aminophenol, o-aminothiophenol, catechols and anilines ortho-substituted by CH₂NH₂ and CONH₂ to form the corresponding benzimidazolones, benzoxazolones, benzothiazolones, benzodioxolones, 3,4-dihydroquinazolin-2(1H)-one and quinazolinediones resp. This methodol. was also applicable for the preparation of the corresponding thio analogs starting from aryl/alkyl isothiocyanates or CS₂ in good to excellent yields. Based on the results of experiments performed using an o-aminobenzamido dianion lanthanide complex, a general mechanism involving the tandem reaction of two lanthanide-ligand bonds was proposed. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6HPLC of Formula: 1843-21-6).

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

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

Relative reactivity of groups bonded to positions 2 and 5 of the thiazole ring was written by Bosco, Marcella;Forlani, Luciano;Todesco, Paolo E.;Troisi, Luigi. And the article was included in Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999) in 1976.Computed Properties of C9H7NS This article mentions the following:

The substitution of halogen by MeO-, MeS- and PhS- ions and oxidation of phenylsulfinyl to phenylsulfonyl by PhC(O)OOH at positions 2 and 5 of the thiazole ring were studied quant. The ratio of the reactivities of the positions was moderate and the unusual nucleophilic halogen displacement for 5-halothiazoles together with the oxidation of the 5-sulfinyl groups indicated the slightly pos. character of C-5. 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. 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.Computed Properties of C9H7NS

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

Determination of acetazolamide in biological fluids by high-performance liquid chromatography was written by Gal, Joseph;Ellis, Philip P.;Rendi, Maris. And the article was included in Current Eye Research in 1981.Related Products of 69812-29-9 This article mentions the following:

A high-performance liquid chromatog. (HPLC) assay for acetazolamide (I) [59-66-5] is presented. A 100-μL sample is mixed with an aliquot of the internal standard solution and the mixture, buffered at pH 4.5, is extracted with Et acetate. The extract is evaporated to dryness and the residue is analyzed by HPLC, using a reverse-phase octadecylsilane column. The wavelength of the detection is 254 nm. The relative standard deviation in the within-day anal. of replicate 10-μg/mL acetazolamide samples in human blood plasma was 6.5%, whereas the between-day relative standard deviation was 7.1%. The procedure was developed for the 1-25 μg/mL acetazolamide concentration range. The internal standard used is similar in chem. structure to acetazolamide and can be readily prepared in one step from a com. available precursor. In addition to blood serum or plasma, the assay can also use aqueous and vitreous human samples. Theophylline and acetaminophen interfere in the assay. The technique was used to determine the concentration of acetazolamide in the blood serum of human volunteers after an oral dose of the drug, and in the aqueous and vitreous humors of rabbits after an i.v. dose of acetazolamide. In the experiment, the researchers used many compounds, for example, 2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9Related Products of 69812-29-9).

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). 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.Related Products of 69812-29-9

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

1,10-phenanthroline-catalyzed tandem reaction of 2-iodoanilines with isothiocyanates in water was written by Zhang, Wu;Yue, Yun;Yu, Dan;Song, Lei;Xu, Yang-Yang;Tian, Yu-Jie;Guo, Yu-Jun. And the article was included in Advanced Synthesis & Catalysis in 2012.Safety of N-Phenylbenzo[d]thiazol-2-amine This article mentions the following:

The 1,10-phenanthroline-catalyzed tandem reaction of 2-iodoanilines with isothiocyanates in water was carried out, which provides an environmentally benign, efficient and simple route for the preparation of 2-aminobenzothiazoles. The present tandem process shows broad substrate scope in the absence of transition metals and phase-transfer catalysts. © 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Safety of N-Phenylbenzo[d]thiazol-2-amine).

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

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

Direct Arylation of Simple Azoles Catalyzed by 1,10-Phenanthroline Containing Palladium Complexes: An Investigation of C4 Arylation of Azoles and the Synthesis of Triarylated Azoles by Sequential Arylation was written by Shibahara, Fumitoshi;Yamaguchi, Eiji;Murai, Toshiaki. And the article was included in Journal of Organic Chemistry in 2011.Application of 1826-13-7 This article mentions the following:

Direct triarylation and sequential triarylation reactions of simple azoles catalyzed by [Pd(phen)₂](PF₆)₂ are described. Simple azoles, such as N-methylimidazole, thiazole, and oxazole, were observed to undergo triarylation reactions even at their C4 positions when treated with aryl iodides in the presence of [Pd(phen)₂](PF₆)₂ as a catalyst and a stoichiometric amount of Cs₂CO₃ in DMA at 150 °C. Using excess amounts of azoles, selective C5 monoarylation was achieved by using the same catalytic system. Subsequent efforts demonstrated that C5 arylated azoles undergo exclusive C2 arylation using [Pd(phen)₂](PF₆)₂ as the catalyst with galvinoxyl as an additive. Finally, unprecedented C4 arylation reactions of 2,5-diarylazoles occur by using the new catalytic system to give the corresponding triarylated products in good to excellent yields. The results of mechanistic studies suggest that the C2 arylation process takes place by way of an electrophilic aromatic substitution (S_EAr) palladation pathway, while arylation reactions at the C4 position occur via a S_EAr palladation and/or radical mechanism. Finally, a concise, three-step synthesis of the Tie-2 Tyrosine Kinase Inhibitor has been executed starting with com. available N-methylimidazole by a route that employs the new sequential arylation process. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Application of 1826-13-7).

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. 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.Application of 1826-13-7

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

Conformational analysis and electronic structure of phenylthiazoles and their protonated forms was written by Galasso, V.;Trinajstic, N.. And the article was included in Tetrahedron in 1972.Application of 1826-13-7 This article mentions the following:

The most probable conformation of 2-, 4-, and 5-phenylthiazole and their protonated forms was investigated using the extended Hueckel MO approach and it was found to be non-planar, the angle of twist about the interring linkage increasing in the order: 4- < 2- < 5-. For the energetically most favorable geometry the charge distribution calculated using the CNDO/2 (complete neglect of differential overlap) method is found to be consistent with the observed dipole moment. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Application of 1826-13-7).

5-Phenylthiazole (cas: 1826-13-7) 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.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Application of 1826-13-7

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

Thin-layer chromatography of thiazole derivatives was written by Vernin, Gaston;Metzger, Jacques. And the article was included in Chimie Analytique (Paris) in 1964.Electric Literature of C9H7NS This article mentions the following:

A series of thiazoles having Cl, SMe, OH, NH₂, or SH in the 2-position and phenyl, p-tolyl, p-bromophenyl, p-chlorophenyl, p-methoxyphenyl, or p-nitrophenyl in the 4-position are separated by thin-layer chromatography on silica gel using heptane or benzene as the eluting solvent. Some 2, 4, 5-trisubstituted thiazoles were also tried. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Electric Literature of C9H7NS).

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

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

DDQ-promoted C-S bond formation: synthesis of 2-aminobenzothiazole derivatives under transition-metal-, ligand-, and base-free conditions was written by Wang, Rui;Yang, Wen-juan;Yue, Liang;Pan, Wei;Zeng, Hong-yao. And the article was included in Synlett in 2012.Recommanded Product: N-Phenylbenzo[d]thiazol-2-amine This article mentions the following:

A transition-metal-free method for the intramol. S-arylation of o-halobenzothioureas via DDQ-mediated leading to the 2-aminobenzothiazole derivatives, e.g., I (R = H, Me, MeO, F; R² = H, Me, MeO, Cl, Br), is reported. The reactions are performed at room temperature under ligand- and base-free conditions with good to excellent yields. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Recommanded Product: N-Phenylbenzo[d]thiazol-2-amine).

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

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