Category: thiazole

Visible-Light-Driven Synthesis of 4-Alkyl/Aryl-2-Aminothiazoles Promoted by In Situ Generated Copper Photocatalyst was written by Lei, Wen-Long;Wang, Tao;Feng, Kai-Wen;Wu, Li-Zhu;Liu, Qiang. And the article was included in ACS Catalysis in 2017.Electric Literature of C15H12N2S This article mentions the following:

Aryl- and alkyl-substituted 2-aminothiazoles were prepared chemoselectively by photochem. cyclocondensation of vinyl azides with ammonium thiocyanate in the presence of Cu(OAc)₂ under blue (visible) light LED irradiation at ambient temperature The mechanism of the cyclocondensation was studied; bis(thiocyanato)copper(I) anion generated in situ acted as both a catalyst for photochem. generation of azirines from vinyl azides and for ring opening of the azirines with thiocyanate. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Electric Literature of C15H12N2S).

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

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

Synthesis of 2-Aminobenzothiazoles via Copper(I)-Catalyzed Cross-Coupling with Part-Per-Million Catalyst Loadings was written by Sun, Ya-Lei;Zhang, Yuan;Cui, Xiao-Hui;Wang, Wei. And the article was included in Advanced Synthesis & Catalysis in 2011.Product Details of 1843-21-6 This article mentions the following:

An efficient protocol has been developed for the preparation of 2-aminobenzothiazoles via a copper(I)-catalyzed tandem reaction of 2-iodoanilines with isothiocyanates at very low catalyst loadings [typically 50 ppm of copper(I) iodide (CuI)]. A variety of 2-iodoanilines could be cross-coupled with isothiocyanates, affording 2-aminobenzothiazoles in moderate to good yields (49-93%) under the given conditions. The turnover number (TON) of this reaction reaches 67,000 and the reaction could be scaled up, at least, to the gram-scale. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Product Details of 1843-21-6).

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. 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.Product Details of 1843-21-6

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

Iron-catalyzed one-pot synthesis of 2-aminobenzothiazoles from 2-aminobenzenethiols and isothiocyanates under ligand-free conditions in water was written by Wang, Wenying;Zhong, Wenying;Zhou, Runxia;Yu, Jinsheng;Dai, Juan;Ding, Qiuping;Peng, Yiyuan. And the article was included in Heterocycles in 2010.Recommanded Product: 1843-21-6 This article mentions the following:

A practical and efficient method for the synthesis of 2-aminobenzothiazoles was developed via an Fe-catalyzed 1-pot tandem reaction. Various 2-aminobenzothiazoles were conveniently synthesized in moderate to excellent yields. The reaction was conducted under ligand-free conditions in water. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Recommanded Product: 1843-21-6).

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.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Recommanded Product: 1843-21-6

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

The formation of 1,3-benzothiazole derivatives from 2,2′-diaminodiphenyl disulfide. Sulfocyanation of 2,2′-diaminodiphenyl sulfide and its reaction with N-aryl isothiocyanates was written by Vinkler, E.;Klivenyi, F.. And the article was included in Acta Chimica Academiae Scientiarum Hungaricae in 1977.COA of Formula: C13H10N2S This article mentions the following:

Reaction of (2-H₂NC₆H₄S)₂ (I) with HSCN gave a mixture containing 80% II (R = H) and 20% III. Treatment of I with RNCS (R = Ph, p-ClC₆H₄, Me, p-BrC₆H₄) gave only II. O-H₂NC₆H₄SH and o-HSC₆HNC(:NH)H were intermediates in the reaction of I and HSCN to form II. 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. 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.COA of Formula: C13H10N2S

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

Associating effect of the hydrogen atom. XI. Hydrogen bonds involving the sulfur atom. The S-H-N bond was written by Hopkins, Gordon;Hunter, Louis. And the article was included in Journal of the Chemical Society in 1942.COA of Formula: C13H10N2S This article mentions the following:

By an examination of the mol. condition of 35 organic S compounds, it is shown that thioamides possessing the group NHCS are associated by virtue of intermol. S-H-N bonds. The results clearly show that, provided 1 or both of the H atoms of the CSNH₂ group remain unsubstituted (RCSNH₂ or RCSNHR’), the compounds exhibit a marked degree of association but that replacement of both H atoms by alkyl or aryl groups (RCSNR’R”) results in loss of associated character. Whether the replacement of the 2nd H atom is effected in MeCSNMePh or in MeC(SMe):NPh, the resulting check in association is the same in both cases. The following were prepared by the action of P₂S₅ on the corresponding amide, by heating them alone or, in better yield, in boiling dry xylene: thioaceto-m-toluide, buff, m. 64°; thiopropiono-p-toluide, fine yellow plates, m. 52-3°; N-ethylthioacetanilide, very pale yellow, m. 49°; N-benzylthioacetanilide, cream, m. 82-3°; N-benzylthiobenzanilide, bright lemon-yellow, m. 119-20°; o-nitrothioacetanilide (I), orange, m. 109°; m-isomer, S-yellow, m. 98°; p-isomer, S-yellow, m. 175°; Me thioacetylanthranilate (II), pale yellow, m. 110-11°; Et p-thioacetamidobenzoate, pale yellow, m. 98°; p-thioacetamidoazobenzene, light red-brown, m. 143-4°; 2-thioacetamido-5,4′-dimethylazobenzene (III), dark brown, m. 137-9°. Although MeCSNHPh shows a high degree of association, I-III are all substantially unimol.; it is evident that intramol. coördination of the anilido-H atom renders it no longer available for intermol. coördination of the type postulated for MeCSNHPh. On the other hand, isomers (or close analogs) of these compounds having m- or p-substituents [p-MeCSNHC₆H₄NO₂(CO₂Et, N₂Ph)], in which the donor groups are too far removed to involve the anilido-H atom in chelate ring formation, prove to be as highly associated as MeCSNHPh. 2-Thiolbenzothiazole is highly associated, whereas the 1-Me derivative is substantially unimol.; 2-methylbenzothiazole is completely unassocd. and may be regarded as the cyclic analog of MeC(SMe):NPh; 2-phenylaminobenzothiazole is strongly associated, probably because of amidine association The previous idea that tautomeric character predisposes a H atom to H-bond formation receives support from a comparison of thiodiphenylamine and thioacridone; the latter shows high association in PhNO₂, whereas the S-Me and S-Bz derivatives are unassocd. in C₁₀H₈. It is probable that bivalent S when a member of a cyclic system does not form H bonds. HCSNMe₂ is highly associated in C₆H₆, although it cannot contain S-H-N bonds. In general, the mol. weights were determined in C₁₀H₈ by the cryoscopic method. 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. The thiazole ring is notable as a component of the vitamin thiamine (B1). 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.COA of Formula: C13H10N2S

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

SAR of novel benzothiazoles targeting an allosteric pocket of DENV and ZIKV NS2B/NS3 proteases was written by Maus, Hannah;Barthels, Fabian;Hammerschmidt, Stefan Josef;Kopp, Katja;Millies, Benedikt;Gellert, Andrea;Ruggieri, Alessia;Schirmeister, Tanja. And the article was included in Bioorganic & Medicinal Chemistry in 2021.Electric Literature of C9H10N2O2S This article mentions the following:

In recent years, dengue virus (DENV) and Zika virus (ZIKV), both mosquito-borne members of the Flaviviridae family, have emerged as intercontinental health issues since their vectors have spread from their tropical origins to temperate climate zones due to climate change and increasing globalization. DENV and ZIKV are pos.-sense, single-stranded RNA viruses, whose genomes consist of three structural (capsid, membrane precursor, envelope) and seven non-structural (NS) proteins, all of which are initially expressed as a single precursor polyprotein. For virus maturation, the polyprotein processing is accomplished by host proteases and the viral NS2B/NS3 protease complex, whose inhibitors have been shown to be effective antiviral agents with loss of viral pathogenicity. In this work, we elucidate new structure-activity relationships of benzo[d]thiazole-based allosteric NS2B/NS3 inhibitors. We developed a new series of Y-shaped inhibitors, which, with its larger hydrophobic contact surface, should bind to previously unaddressed regions of the allosteric NS2B/NS3 binding pocket. By scaffold-hopping, we varied the benzo[d]thiazole core and identified benzofuran as a new lead scaffold shifting the selectivity of initially ZIKV-targeting inhibitors to higher activities towards the DENV protease. In addition, we were able to increase the ligand efficiency from 0.27 to 0.41 by subsequent inhibitor truncation and identified N-(5,6-dihydroxybenzo[d]thiazol-2-yl)-4-iodobenzamide as a novel sub-micromolar NS2B/NS3 inhibitor. Utilizing cell-based assays, we could prove the antiviral activity in cellulo. Overall, we report new series of sub-micromolar allosteric DENV and ZIKV inhibitors with good efficacy profile in terms of cytotoxicity and protease inhibition selectivity. In the experiment, the researchers used many compounds, for example, 5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6Electric Literature of C9H10N2O2S).

5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6) 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. 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.Electric Literature of C9H10N2O2S

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

Molecular modelling design, synthesis and cytotoxic evaluation of certain substituted 2-(3,4,5-triacetoxybenzoylamino)benzo[d]thiazole and 2-(galloylamino)benzo[d]thiazole derivatives having potential topoisomerase-I inhibitory activity was written by Ismail, Mohamed A. H.;Tratrat, Christophe;Haroun, Michelyne G.. And the article was included in Journal of Enzyme Inhibition and Medicinal Chemistry in 2013.Name: 5,6-Dimethoxybenzo[d]thiazol-2-amine This article mentions the following:

New 2-(3,4,5-triacetoxybenzoylamino)benzothiazoles (4a∼5f) and 2-(galloylamino)benzothiazoles (6a∼7f), were designed as topoisomerase-I inhibitors. Compare/fit studies between these mols. and the generated topoisomerase-I inhibitors hypothesis revealed that 4a∼5f have higher fitting values than (6a∼7f). Also, docking of 4a∼7f with the topoisomerase-I enzyme prioritized the higher activity of (4a∼5f) than (6a∼7f). These mols. were synthesized and biol. evaluated for their in vitro cytotoxic activity against Hela and MCF7 human cancer cell lines in comparison to Camptothecin (topo-I inhibitor) and doxorubicin (topo-II inhibitors) as reference drugs. Such screening revealed that compounds 4d, 4e, 4h, 5b, 5c and 5e have comparable higher cytotoxic activity in both cultures than these reference drugs. The highest active mol. was 5f that gave 1.5 folds higher cytotoxic activity against Hela cell cultures and 1.9 folds higher activity against MCF7 cell lines than doxorubicin and 1.6 folds and 2.2 folds higher activity towards the two resp. cultures than Camptothecin. In the experiment, the researchers used many compounds, for example, 5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6Name: 5,6-Dimethoxybenzo[d]thiazol-2-amine).

5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6) 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.Name: 5,6-Dimethoxybenzo[d]thiazol-2-amine

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

Preparation of aminothiazole hydrochlorides was written by Kopp, Marianne. And the article was included in Bulletin de la Societe Chimique de France in 1950.Synthetic Route of C15H12N2S This article mentions the following:

2-Amino-4,5-disubstituted thiazoles are prepared from α-chloro ketones and CS(NH₂)₂. CS(NH₂)₂ (1 mole) and the appropriate α-chloro ketone (1 mole) in boiling EtOH (1 l., several hrs.) afford after treatment with alkali the following 2-amino-4,5-disubstituted thiazoles: 2-amino-4,5-diphenyl (hydrochloride, m. 180-3°; picrate, m. 194-5°); 2-amino-4,5-tetramethylene, m. 92-3° (hydrochloride, m. 223-5°); 2-amino-4-phenyl-5-methyl, m. 118°, (hydrochloride, m. 191°); 2-amino-4-phenyl-5-ethyl, m. 93° (hydrochloride, m. 167°); 2-amino-5-phenyl-4-methyl, m. 164-6° (hydrochloride, m. 191°; picrate, m. 235°); and 2-amino-4-methyl-5-benzylthiazole, m. 107° (hydrochloride, m. 175°). 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. 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.Synthetic Route of C15H12N2S

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

Using ‘biased-privileged’ scaffolds to identify lysine methyltransferase inhibitors was written by Kashyap, Sudhir;Sandler, Joel;Peters, Ulf;Martinez, Eduardo J.;Kapoor, Tarun M.. And the article was included in Bioorganic & Medicinal Chemistry in 2014.SDS of cas: 69812-29-9 This article mentions the following:

Methylation of histones by lysine methyltransferases (KMTases) plays important roles in regulating chromatin function. It is also now clear that improper KMTases activity is linked to human diseases, such as cancer. The authors report an approach that employs drug-like ‘privileged’ scaffolds biased with motifs present in S-adenosyl methionine, the cofactor used by KMTases, to efficiently generate inhibitors for Set7, a biochem. well-characterized KMTase. Setin-1, the most potent inhibitor of Set7 the authors have developed also inhibits the KMTase G9a. Together these data suggest that these inhibitors should provide good starting points to generate useful probes for KMTase biol. and guide the design of KMTase inhibitors with drug-like properties. In the experiment, the researchers used many compounds, for example, 2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9SDS of cas: 69812-29-9).

2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9) 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. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.SDS of cas: 69812-29-9

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

Encoded Library Technology as a Source of Hits for the Discovery and Lead Optimization of a Potent and Selective Class of Bactericidal Direct Inhibitors of Mycobacterium tuberculosis InhA was written by Encinas, Lourdes;O’Keefe, Heather;Neu, Margarete;Remuinan, Modesto J.;Patel, Amish M.;Guardia, Ana;Davie, Christopher P.;Perez-Macias, Natalia;Yang, Hongfang;Convery, Maire A.;Messer, Jeff A.;Perez-Herran, Esther;Centrella, Paolo A.;Alvarez-Gomez, Daniel;Clark, Matthew A.;Huss, Sophie;O’Donovan, Gary K.;Ortega-Muro, Fatima;McDowell, William;Castaneda, Pablo;Arico-Muendel, Christopher C.;Pajk, Stane;Rullas, Joaquin;Angulo-Barturen, Inigo;Alvarez-Ruiz, Emilio;Mendoza-Losana, Alfonso;Ballell Pages, Lluis;Castro-Pichel, Julia;Evindar, Ghotas. And the article was included in Journal of Medicinal Chemistry in 2014.Application In Synthesis of Thiazol-2-ylmethanamine This article mentions the following:

Tuberculosis (TB) is one of the world’s oldest and deadliest diseases, killing a person every 20 s. InhA, the enoyl-ACP reductase from Mycobacterium tuberculosis, is the target of the frontline antitubercular drug isoniazid (INH). Compounds that directly target InhA and do not require activation by mycobacterial catalase peroxidase KatG are promising candidates for treating infections caused by INH resistant strains. The application of the encoded library technol. (ELT) to the discovery of direct InhA inhibitors yielded compound I endowed with good enzymic potency but with low antitubercular potency. This work reports the hit identification, the selected strategy for potency optimization, the structure-activity relationships of a hundred analogs synthesized, and the results of the in vivo efficacy studies performed with the lead compound II. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Application In Synthesis of Thiazol-2-ylmethanamine).

Thiazol-2-ylmethanamine (cas: 55661-33-1) 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. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Application In Synthesis of Thiazol-2-ylmethanamine

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