Category: thiazole

Convenient and Reliable Routes Towards 2-Aminothiazoles: Palladium-Catalyzed versus Copper-Catalyzed Aminations of Halothiazoles was written by Toulot, Stephanie;Heinrich, Timo;Leroux, Frederic R.. And the article was included in Advanced Synthesis & Catalysis in 2013.Application In Synthesis of N-Phenylbenzo[d]thiazol-2-amine This article mentions the following:

Two efficient methods for the amination of 2-halothiazoles are presented here. A first protocol requires a Pd/L system. Several 2-aminothiazoles, e.g., I, were synthesized under optimized conditions and isolated in good yields. The first palladium-catalyzed C-N coupling reactions between 2-halothiazoles and primary alkylamines are presented. In a second part, ligand-free copper-catalyzed aminations of 2-halothiazoles by alkylamines and aniline in a green solvent have been developed. The protocol is very effective for primary and secondary amines and perfectly tolerates the presence of another halide moiety on the 2-halothiazole. The reaction occurs under the assistance of microwave irradiation, which drastically decreases the reaction time. The reaction leads to the formation of 2-aminothiazoles, key mols. in pharmaceutical research. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Application In Synthesis of N-Phenylbenzo[d]thiazol-2-amine).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) belongs to thiazole derivatives. Thiazoles in peptides or their ability to bind proteins, DNA and RNA has led to many synthetic studies and new applications. 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 N-Phenylbenzo[d]thiazol-2-amine

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

2-Amino-4-arylthiazoles through One-Pot Transformation of Alkylarenes with NBS and Thioureas was written by Shibasaki, Kaho;Togo, Hideo. And the article was included in European Journal of Organic Chemistry in 2019.Category: thiazole This article mentions the following:

Treatment of alkylarenes with N-bromosuccinimide in a mixture of Et acetate and water at 60 °C, a mixture of acetonitrile and water at 80 °C, or a mixture of di-Et carbonate and water under irradiation with a tungsten lamp, followed by a reaction with thioureas or arenethioamides provided the corresponding 2-amino-4-arylthiazoles or 2,4-diarylthiazoles in good to moderate yields, resp., in one pot [e.g., ethylbenzene + thiourea → 2-amino-4-phenylthiazole (84%)]. The present reaction is an efficient one-pot transformation method of alkylarenes into 2-amino-4-arylthiazoles and 2,4-diarylthiazoles directly under mild and transition-metal-free conditions. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Category: thiazole).

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.Category: thiazole

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

Cross-coupling of sulfonic acid derivatives via aryl-radical transfer (ART) using TTMSS or photoredox was written by Nacsa, Eric D.;Lambert, Tristan H.. And the article was included in Organic Chemistry Frontiers in 2018.Electric Literature of C6H7ClN2O3S2 This article mentions the following:

The intramol. cross-coupling of sulfonic acid derivatives occurs in the presence of tris(trimethylsilyl)silane (TTMSS) at room temperature and in air to form biaryl compounds A photoredox-catalyzed procedure is also described. These protocols provide mild and convenient alternatives to standard tin-mediated reactions. Combined with the trivial preparation of the substrates from activated sulfonic acids and 2-halophenols or anilines, this work presents a useful means to employ sulfonic acid derivatives in cross-coupling transformations. A modified linker to realize high regioselectivity is also presented. Finally, a one-pot cross-coupling procedure is demonstrated. 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. 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.Electric Literature of C6H7ClN2O3S2

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

Synthesis of N-arylamines in dry media and their antibacterial activity was written by Ramana, M. M. V.;Sharma, Madhu R.. And the article was included in Journal of Chemical and Pharmaceutical Research in 2013.Reference of 1843-21-6 This article mentions the following:

A number of N-aryl amines were synthesized by N-arylation of primary/secondary amines with activated aryl halides in the presence of KF/Al₂O₃ (basic) dry media at room temperature The newly prepared Compounds were examined for their antibacterial activity against E. coli, S. typhi, B. subtilis, and S. aureus. Some of the compounds showed significant antibacterial activity. 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. Thiazole rings are planar and aromatic. Thiazoles are characterized by larger pi-electron delocalization than the corresponding oxazoles and have therefore greater aromaticity. 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.Reference of 1843-21-6

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

Ligand-controlled palladium catalysis enables switch between mono- and di-arylation of primary aromatic amines with 2-halobenzothiazoles was written by Zhu, Yan-Qiu;Zhang, Rui;Sang, Wei;Wang, Hua-Jing;Wu, Yuan;Yu, Bao-Yi;Zhang, Jun-Chao;Cheng, Hua;Chen, Cheng. And the article was included in Organic Chemistry Frontiers in 2020.Electric Literature of C13H10N2S This article mentions the following:

Herein, a wide range of mono- and di-arylated products were efficiently prepared from C-N coupling of 2-halobenzothiazoles and primary aromatic amines, and representative compounds I and II were further confirmed by X-ray crystallog. It was noteworthy that the di-arylated products, denoted as di(benzothiazolyl)amines, are new chem. entities which have not yet been reported. Moreover, the ligand-controlled protocol was extended to the synthesis of target mols. bearing a di-Ph ether or di-Ph amine scaffold. Several compounds exhibited good inhibitory activity against succinate-cytochrome c reductase (SCR), which revealed the practical application of this protocol. Notably, selective mono- and di-arylation could be switched simply by varying the ligand from Xantphos to a pyridine-functionalized N-heterocyclic carbene (NHC) ligand, and further investigations were carried out to elucidate the possible reason for this new finding. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Electric Literature of C13H10N2S).

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.Electric Literature of C13H10N2S

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

Synthesis of N-substituted-2-aminobenzothiazoles using nano copper oxide as a recyclable catalyst under ligand-free conditions, in reusable PEG-400 medium was written by Gaddam, Satish;Kasireddy, Harshavardhan Reddy;Konkala, Karnakar;Katla, Ramesh;Durga, Nageswar Yadavalli Venkata. And the article was included in Chinese Chemical Letters in 2014.COA of Formula: C13H10N2S This article mentions the following:

A simple and practical method for the synthesis of 2-arylaminobenzothiazoles via a cross-coupling reaction of 2-iodoanilines with isothiocyanates is envisaged using nano copper oxide as a recyclable catalyst and Cs₂CO₃ as a base in PEG-400, as a bio-degradable, reusable, inexpensive and non-toxic reaction medium, under ligand-free conditions. The present tandem process underlines environmental acceptability to access a wide range of N-substituted-2-aminobenzothiazoles in good to excellent yields. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6COA of Formula: C13H10N2S).

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. 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: C13H10N2S

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

Quantitative studies of hydroperoxide reduction by prostaglandin H synthase. Reducing substrate specificity and the relationship of peroxidase to cyclooxygenase activities was written by Markey, Christine M.;Alward, Abdo;Weller, Paul E.;Marnett, Lawrence J.. And the article was included in Journal of Biological Chemistry in 1987.HPLC of Formula: 6318-74-7 This article mentions the following:

The peroxidase activity of prostaglandin H (PGH) synthase catalyzes reduction of 5-phenyl-4-pentenyl hydroperoxide to 5-phenyl-4-pentenyl alc. with a turnover number of ∼8000 mol of 5-phenyl-4-pentenyl hydroperoxide/mol of enzyme/min. The kinetics and products of reaction establish PGH synthase as a classical heme peroxidase with catalytic efficiency similar to horseradish peroxidase. This suggests that the protein of PGH synthase evolved to facilitate peroxide heterolysis by the heme prosthetic group. Comparison of an extensive series of phenols, aromatic amines, β-carbonyls, naturally occurring compounds, and nonsteroidal anti-inflammatory drugs indicates that considerable differences exist in their ability to act as reducing substrates. No correlation is observed between the ability of compounds to support peroxidatic hydroperoxide reduction and to inhibit cyclooxygenase. In addition, the resolved enantiomers of MK-410 and etodolac exhibit dramatic enantiospecific differences in their ability to inhibit cyclooxygenase but are equally potent as peroxidase-reducing substrates. This suggests that there are significant differences in the orientation of compounds at cyclooxygenase inhibitory sites and the peroxidase oxidation site(s). Comparison of 5-phenyl-4-pentenyl hydroperoxide reduction by PGH synthase and horseradish peroxidase reveals considerable differences in reducing substrate specificity. Both the cyclooxygenase and peroxidase activities of PGH synthase inactivate in the presence of low micromolar amounts of hydroperoxides and arachidonic acid. PGH synthase was most sensitive to arachidonic acid, which exhibited a concentration for 50% inhibition (I₅₀) of 0.6 μM in the absence of all protective agents. Inactivation by hydroperoxides requires peroxidase turnover and can be prevented by reducing substrates. The I₅₀ values for inactivation by 15-hydroperoxy-5,8,11,13-eicosatetraenoic acid are 4.0 and 92 μM, resp., in the absence and presence of 500 μM phenol, a moderately good reducing substrate. The ability of compounds to protect against hydroperoxide-induced inactivation correlates directly with their ability to act as reducing substrates. Hydroquinone, an excellent reducing substrate, protected against hydroperoxide-induced inactivation when present in <3-fold molar excess over hydroperoxide. The presence of a highly efficient hydroperoxide-reducing activity appears absolutely essential for protection of the cyclooxygenase capacity of PGH synthase. The peroxidase activity is, therefore, a twin-edged sword, responsible for and protective against hydroperoxide-dependent inactivation of PGH synthase. As such, it may constitute an important target for pharmacol. modulation of eicosanoid biosynthesis. 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 structure-activity relationships of novel lincomycin derivatives. Part 1. Newly generated antibacterial activities against Gram-positive bacteria with erm gene by C-7 modification was written by Wakiyama, Yoshinari;Kumura, Ko;Umemura, Eijiro;Ueda, Kazutaka;Masaki, Satomi;Kumura, Megumi;Fushimi, Hideki;Ajito, Keiichi. And the article was included in Journal of Antibiotics in 2016.Formula: C7H4N2O2S2 This article mentions the following:

The authors synthesized 7(S)-7-deoxy-7-arylthiolincomycin derivatives possessing a heterocyclic ring at the C-7 position via sulfur atom by either Mitsunobu reaction of 2,3,4-tris-O-(trimethylsiliyl)lincomycin or S_N2 reaction of 7-O-methanesulfonyl-2,3,4-tri-O-trimethylsiliyllincomycin. As a result, 7(S)-7-deoxy-7-arylthiolincomycin derivatives 7(S)-7-(6-aminobenzo[d]thiazol-2-ylthio)-7-deoxylincomycin (16), 7(S)-7-(5-amino-1,3,4-thiadiazol-2-ylthio)-7-deoxylincomycin (21) and 7(S)-7-deoxy-7-(5-phenyl-1,3,4-thiadiazol-2-ylthio)lincomycin (27) exhibited antibacterial activities against respiratory infection-related Gram-pos. bacteria with erm gene, although clindamycin did not have any activities against those pathogens. Furthermore, 7(S)-configuration of lincomycin derivatives was found to be necessary for enhancing antibacterial activities from the comparison results of configurations of 16 (S-configuration) and 7(R)-7-(6-Aminobenzo[d]thiazol-2-ylthio)-7-deoxylincomycin (30) (R-configuration) at the 7-position. In the experiment, the researchers used many compounds, for example, 5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0Formula: C7H4N2O2S2).

5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0) 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. 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.Formula: C7H4N2O2S2

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

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