Category: thiazole

Environment-friendly and efficient synthesis of 2-aminobenzo-oxazoles and 2-aminobenzothiazoles catalyzed by Vitreoscilla hemoglobin incorporating a cobalt porphyrin cofactor was written by Xu, Yaning;Li, Fengxi;Zhao, Nan;Su, Jiali;Wang, Chunyu;Wang, Ciduo;Li, Zhengqiang;Wang, Lei. And the article was included in Green Chemistry in 2021.Category: thiazole This article mentions the following:

In this study, an environment-friendly and efficient artificial Vitreoscilla Hb (VHb) for the synthesis of 2-aminobenzoxazoles and 2-aminobenzothiazoles has been reported. Authors demonstrate an expression-based porphyrin substitution strategy to produce VHb containing cobalt porphyrin instead of native hemin, which can catalyze the oxidative cyclization of corresponding 2-aminobenzoxazoles and 2-aminobenthiazoles with up to 97% yield and 4850 catalytic turnovers in water under aerobic conditions. Hence, authors provide a green and mild method for the synthesis of 2-aminobenzoxazoles and 2-aminobenzothiazoles. In addition, authors indicate the value of porphyrin ligand substitution as a strategy to tune and enhance the catalytic properties of hemoproteins in non-natural reactions. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Category: thiazole).

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.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Category: thiazole

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

Pyridyl and thiazolyl bisamide CSF-1R inhibitors for the treatment of cancer was written by Scott, David A.;Aquila, Brian M.;Bebernitz, Geraldine A.;Cook, Donald J.;Dakin, Les A.;Deegan, Tracy L.;Hattersley, Maureen M.;Ioannidis, Stephanos;Lyne, Paul D.;Omer, Charles A.;Ye, Minwei;Zheng, XiaoLan. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2008.Electric Literature of C4H6N2S This article mentions the following:

The bisamide class of kinase inhibitors was identified as being active against CSF-1R. The synthesis and SAR of pyridyl and thiazolyl bisamides are reported, along with the pharmacokinetic properties and in vivo activity of selected examples. In the experiment, the researchers used many compounds, for example, 2-Methylthiazol-5-amine (cas: 89281-44-7Electric Literature of C4H6N2S).

2-Methylthiazol-5-amine (cas: 89281-44-7) 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 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.Electric Literature of C4H6N2S

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

2-Amino-4-methyl-5-thiazolesulfonamide and some derivatives was written by Backer, H. J.;de Jonge, J.. And the article was included in Recueil des Travaux Chimiques des Pays-Bas et de la Belgique in 1943.Application of 69812-29-9 This article mentions the following:

ClSO₃H (300 g.) was added to 50 g. of 2-acetamido-4-methylthiazole below 10° with agitation; the mixture was heated for 3 h. at 50°, for 3 h. at 60°, and then poured into a mixture of ice and water. Extraction with 1.5 l. of Et₂O left 14 g. of insoluble 2-acetamido-4-methyl-5-thiazolesulfonic acid (XVI), soluble in H₂O but only slightly soluble in 25% H₂SO₄. The ether solution when washed with water, dried, and distilled yielded 27 g. of 2-acetamido-4-methyl-5-thiazolesulfonyl chloride (XVII), crystals from C₆H₆, m. 159-60°. The Na salt of XVI with ClSO₃H gave XVII. Dry NH₃ passed into 6 g. of XVII in 35 cc. of C₅H₅N gave 4.1 g. of 2-acetamido-4-methyl-5-thiazolesulfonamide, crystals from AcOH, m. 230-1° after drying at 100°, 1 g. of which, heated for 0.25 h. with 6 cc. of 25% HCl, gave 0.5 g. of 2-amino-4-Me 5-thiazolesulfonamide, crystals from H₂O, m. 175-6°. Heating 2.5 g. of XVII with 5 cc. of C₆H₆NH₂ for 0.25 h. at 60° gave 2.7 g. of 2-acetamido-4-methyl-5-thiazolesulfonanilide, crystals from dilute EtOH, m. 198-9°, 2.5 g. of which heated with 20 cc. of 3 N HCl gave 0.9 g. of 2-amino-4-methyl-5-thiazolesulfonanilide (XVIII), crystals from H₂O, m. 135-6°. Heating 5.1 g. of XVII with 1.9 g. of 2-aminopyridine in 30 cc. of C₅H₅N on a water bath for 2 h. gave 3.9 g. 2-(2-acetamido-4-methyl-5-thiazolylsulfonamido)pyridine, crystals from EtOH, m. 229-30° after drying at 105°, 1 g. of which heated with 6 cc. of 3 N HCl for 0.5 h. gave 2-(2-amino-4-methyl-5-thiazolylsulfonamido)pyridine, crystals from H₂O, m. 208-9° (crystals from EtOH contained 1 mol. of EtOH). Heating 7.65 g. of XVII with 3.42 g. of I in 45 cc. of C₅H₅N for 2 h. on a water bath gave 3.4 g. of 2-(2-acetamido-4-methyl-5-thiazolylsulfonamido)-4-methylthiazole, crystals from H₂O, m. 235-6.5°, 1.2 g. of which boiled with 12 cc. of 3 N HCl for 0.5 h. gave 2-(2-amino-4-methyl-5-thiazolylsulfonamido)-4-methylthiazole, crystals from dilute EtOH, decompose near 241°. The compounds were not active against pneumococcal infections in mice. XVIII was very toxic. In the experiment, the researchers used many compounds, for example, 2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9Application of 69812-29-9).

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 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.Application of 69812-29-9

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

Transition-metal-free O-, S-, and N-Arylation of alcohols, thiols, amides, amines, and related heterocycles was written by Cano, Rafael;Ramon, Diego J.;Yus, Miguel. And the article was included in Journal of Organic Chemistry in 2011.Name: N-Phenylbenzo[d]thiazol-2-amine This article mentions the following:

A new protocol for the Ullmann-type arylation process of different aromatic heterocycles without any transition-metal catalyst, implying the use of a combination of an excess of potassium hydroxide and DMSO, is described. The reaction can be performed between a broad range of starting nucleophiles including phenol, alcs., amines, nitrogen-containing five-membered systems such as pyrazoles, imidazoles, and indoles, and amides with haloarenes, iodide and bromide derivatives giving the best results, the possible pathway involving the in situ generation of the corresponding benzyne intermediate. When the reaction was performed with 2-iodoaniline and either carboxamides or isothiocyanato derivatives, the corresponding benzoazole derivatives were obtained. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Name: 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. 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.Name: N-Phenylbenzo[d]thiazol-2-amine

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

Palladium-Catalyzed Decarboxylative Cross-Coupling Reaction Between Heteroaromatic Carboxylic Acids and Aryl Halides was written by Bilodeau, Francois;Brochu, Marie-Christine;Guimond, Nicolas;Thesen, Kris H.;Forgione, Pat. And the article was included in Journal of Organic Chemistry in 2010.Safety of 5-Phenylthiazole This article mentions the following:

A full overview of the decarboxylative cross-coupling reaction between heteroaromatic carboxylic acids and aryl halides is described. This transformation employs palladium catalysts with short reaction times providing facile synthesis of aryl-substituted heteroaromatics E.g., in presence of bis(tri-tert-butylphosphine)palladium, reaction of 1-methyl-2-pyrrolecarboxylic acid and PhBr gave 88% 1-methyl-2-phenylpyrrole. The effect of each reaction parameter including solvent, base, and additive employed as well as the full substrate scope of this transformation are reported. Mechanistic evidence is also disclosed that sheds light on possible reaction pathways. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Safety of 5-Phenylthiazole).

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. 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 5-Phenylthiazole

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

Anti-infective and herbicidal activity of N-substituted 2-aminobenzothiazoles was written by Fajkusova, Dagmar;Pesko, Matus;Keltosova, Stanislava;Guo, Jiahui;Oktabec, Zbynek;Vejsova, Marcela;Kollar, Peter;Coffey, Aidan;Csollei, Jozef;Kralova, Katarina;Jampilek, Josef. And the article was included in Bioorganic & Medicinal Chemistry in 2012.Synthetic Route of C13H10N2S This article mentions the following:

In this study, a series of N-substituted 2-aminobenzothiazoles was prepared according to a recently developed method. Twelve compounds were tested for their activity related to the inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. Primary in vitro screening of the discussed compounds was also performed against fungal, bacterial and mycobacterial species. The biol. activities of some compounds were comparable or higher than the standards phenoxymethylpenicillin or pyrazinamide. The most effective compounds demonstrated insignificant toxicity against the human monocytic leukemia THP-1 cell line. For all compounds, the structure-activity relationships are discussed. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Synthetic Route of C13H10N2S).

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 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.Synthetic Route of C13H10N2S

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

Cobalt-Catalyzed Arylation of Azole Heteroarenes via Direct C-H Bond Functionalization was written by Sezen, Bengue;Sames, Dalibor. And the article was included in Organic Letters in 2003.Reference of 1826-13-7 This article mentions the following:

We herein report a new cobalt-catalyzed method for arylation of azole heteroarenes, including thiazole, oxazole, imidazole, benzothiazole, benzoxazole, and benzimidazole. The direct arylation of thiazole and oxazole was achieved both with iodo- and bromoarenes as the aryl donors in the presence of cobalt catalyst [Co(OAc)₂/IMes] and cesium carbonate, while imidazole required the use of zinc oxide as the base. A complete reversal of arylation from C-5 to C-2 was accomplished using the bimetallic Co/Cu/IMes system. A direct comparison of the new cobalt method and the previously developed palladium protocol revealed significant differences, in terms of both chem. yield and selectivity. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Reference of 1826-13-7).

5-Phenylthiazole (cas: 1826-13-7) 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. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Reference of 1826-13-7

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

Photoinduced Copper-Catalyzed C-H Arylation at Room Temperature was written by Yang, Fanzhi;Koeller, Julian;Ackermann, Lutz. And the article was included in Angewandte Chemie, International Edition in 2016.Electric Literature of C9H7NS This article mentions the following:

Room-temperature azole C-H arylations were accomplished with inexpensive copper(I) compounds by photoinduced catalysis. The expedient copper catalysis set the stage for site-selective C-H arylations of non-aromatic oxazolines under mild reaction conditions, and provides step-economical access to the alkaloid natural products balsoxin and texamine. 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. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. 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.Electric Literature of C9H7NS

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

An efficient synthesis of 2-aminobenzoxazoles and 2-aminobenzothiazoles from 2-aminophenols or 2-aminothiophenols and isoselenocyanates was written by Xie, Yuanyuan;Zhang, Fan;Chen, Xiaodong;Li, Jianjun. And the article was included in Heterocycles in 2010.Category: thiazole This article mentions the following:

An expeditious method to access 2-aminobenzoxazoles and 2-aminobenzothiazoles from various substituted 2-aminophenols and 2-aminothiophenol, resp., with isoselenocyanates in a one pot procedure is reported. Elemental Se precipitates nearly quant. in the reaction without any deselenizing agent and it can be reused. A possible mechanism for the formation of the target products is proposed. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Category: thiazole).

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 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.Category: thiazole

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

Design, synthesis and biological evaluation of novel diphenylthiazole-based cyclooxygenase inhibitors as potential anticancer agents was written by Abdelazeem, Ahmed H.;Gouda, Ahmed M.;Omar, Hany A.;Tolba, Mai F.. And the article was included in Bioorganic Chemistry in 2014.Application In Synthesis of 4,5-Diphenylthiazol-2-amine This article mentions the following:

Non-steroidal anti-inflammatory drugs (NSAIDs) are among the most widely used medications as analgesics and antipyretics. Currently, there is a growing interest in their antitumor activity and their ability to reduce the risk and mortality of several cancers. While several studies revealed the ability of NSAIDs to induce apoptosis and inhibit angiogenesis in cancer cells, their exact anticancer mechanism is not fully understood. However, both cyclooxygenase (COX)-dependent and -independent pathways were reported to have a role. In an attempt to develop new anticancer agents, a series of diphenylthiazole substituted thiazolidinone derivatives was synthesized and evaluated for their anticancer activity against a panel of cancer cell lines. Addnl., the inhibitory activity of the synthesized derivatives against COX enzymes was investigated as a potential mechanism for the anticancer activity. Cytotoxicity assay results showed that compounds 15b and 16b were the most potent anticancer agents with half maximal inhibitory concentrations (IC₅₀) between 8.88 and 19.25 μM against five different human cancer cell lines. Interestingly, COX inhibition assay results were in agreement with that of the cytotoxicity assays where the most potent anticancer compounds showed good COX-2 inhibition comparable to that of celecoxib. Further support to our results were gained by the docking studies which suggested the ability of compound 15b to bind into COX-2 enzyme with low energy scores. Collectively, these results demonstrated the promising activity of the newly designed compounds as leads for subsequent development into potential anticancer agents. 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 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. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Application In Synthesis of 4,5-Diphenylthiazol-2-amine

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