Tag: 200-300

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

Discovery of potent, selective small molecule inhibitors of α-subtype of type III phosphatidylinositol-4-kinase (PI4KIIIα) was written by Raubo, Piotr;Andrews, David M.;McKelvie, Jennifer C.;Robb, Graeme R.;Smith, James M.;Swarbrick, Martin E.;Waring, Michael J.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2015.COA of Formula: C7H3BrClNS This article mentions the following:

The discovery and optimization of novel, potent and selective small mol. inhibitors of the α-isoform of type III phosphatidylinositol-4-kinase (PI4Kα) are described. Lead compounds show cellular activity consistent with their PI4Kα potency inhibiting the accumulation of IP1 after PDGF stimulation and reducing cellular PIP, PIP2 and PIP3 levels. Hence, these compounds are useful in vitro tools to delineate the complex biol. pathways involved in signaling through PI4Kα. In the experiment, the researchers used many compounds, for example, 6-Bromo-2-chlorobenzothiazole (cas: 80945-86-4COA of Formula: C7H3BrClNS).

6-Bromo-2-chlorobenzothiazole (cas: 80945-86-4) 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. 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.COA of Formula: C7H3BrClNS

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

Imine-amine isomerization in a series of benzothiazoles was written by Saprykina, V. A.;Ambartsumova, R. F.. And the article was included in Doklady Akademii Nauk UzSSR in 1987.Category: thiazole This article mentions the following:

Thermolysis of iminobenzothiazole (I; R = Me) at 110° gave predominantly isomerized aminobenzothiazole (II; 45%) and bis(benzothiazolylamino) derivative (III; 47%). Thermolysis of I (R = H) afforded tetrahydropyrimidinobenzothiazole IV in 41% yield. 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. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Category: thiazole

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

Facile, efficient synthesis of polysubstituted thiazoles via α-nitroepoxides and thioureas was written by Zhao, Donghong;Guo, Shanshan;Guo, Xiao;Zhang, Guolin;Yu, Yongping. And the article was included in Tetrahedron in 2016.Name: 4,5-Diphenylthiazol-2-amine This article mentions the following:

An efficient synthesis of 2,4,5-trisubstituted thiazoles via the reaction of α-nitroepoxides and thioureas under mild conditions was developed. This reaction proceeded well at room temperature, to afford products in excellent yields for a wide range of substrate and a possible mechanism was proposed. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Name: 4,5-Diphenylthiazol-2-amine).

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

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