Category: thiazole

Dithiocarbamate promoted practical synthesis of N-Aryl-2-aminobenzazoles: Synthesis of novel Aurora-A kinase inhibitor was written by Katari, Naresh Kumar;Venkatanarayana, M.;Srinivas, Kummari. And the article was included in Journal of Chemical Sciences (Bangalore, India) in 2015.Recommanded Product: 1843-21-6 This article mentions the following:

Various N-aryl-2-aminobenzoxazoles and N-aryl-2-aminobenzothiazoles were synthesized from o-aminophenol and o-aminothiophenol, resp., mediated by dithiocarbamate in one step. The salient features of this method included mild reaction condition, high yield and large scale synthesis. Application of this methodol. was demonstrated by synthesizing potent Aurora kinase-A inhibitors. 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. 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. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Recommanded Product: 1843-21-6

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

Dipicolinic Acid Derivatives as Inhibitors of New Delhi Metallo-β-lactamase-1 was written by Chen, Allie Y.;Thomas, Pei W.;Stewart, Alesha C.;Bergstrom, Alexander;Cheng, Zishuo;Miller, Callie;Bethel, Christopher R.;Marshall, Steven H.;Credille, Cy V.;Riley, Christopher L.;Page, Richard C.;Bonomo, Robert A.;Crowder, Michael W.;Tierney, David L.;Fast, Walter;Cohen, Seth M.. And the article was included in Journal of Medicinal Chemistry in 2017.Category: thiazole This article mentions the following:

The efficacy of β-lactam antibiotics is threatened by the emergence and global spread of metallo-β-lactamase (MBL) mediated resistance, specifically New Delhi metallo-β-lactamase-1 (NDM-1). By utilization of fragment-based drug discovery (FBDD), a new class of inhibitors for NDM-1 and two related β-lactamases, IMP-1 and VIM-2, was identified. On the basis of 2,6-dipicolinic acid (DPA), several libraries were synthesized for structure-activity relationship (SAR) anal. Inhibitor I (IC₅₀ = 80 nM) was identified to be highly selective for MBLs when compared to other Zn(II) metalloenzymes. While DPA displayed a propensity to chelate metal ions from NDM-1, I formed a stable NDM-1:Zn(II):inhibitor ternary complex, as demonstrated by ¹H NMR, ESR (EPR) spectroscopy, equilibrium dialysis, intrinsic tryptophan fluorescence emission, and UV-vis spectroscopy. When coadministered with I (at concentrations nontoxic to mammalian cells), the min. inhibitory concentrations (MICs) of imipenem against clin. isolates of Escherichia coli and Klebsiella pneumoniae harboring NDM-1 were reduced to susceptible levels. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Category: thiazole).

Thiazol-2-ylmethanamine (cas: 55661-33-1) 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.Category: thiazole

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

Synthesis of 2-aminobenzothiazole via FeCl₃-catalyzed tandem reaction of 2-iodoaniline with isothiocyanate in water was written by Ding, Qiuping;Cao, Banpeng;Liu, Xianjin;Zong, Zhenzhen;Peng, Yi-Yuan. And the article was included in Green Chemistry in 2010.Recommanded Product: N-Phenylbenzo[d]thiazol-2-amine This article mentions the following:

An FeCl₃-catalyzed tandem reaction of 2-iodoanilines with isothiocyanates in water is described, which provides an environmentally benign, efficient, and practical route for the generation of 2-aminobenzothiazoles, e.g. I. This present tandem process shows broad substrate scope in the presence of octadecyltrimethylammonium chloride as a phase-transfer catalyst. In addition, the reaction media can be recovered and recycled without loss of efficiency. 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. 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. 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.Recommanded Product: N-Phenylbenzo[d]thiazol-2-amine

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

Synthesis of 4-substituted imino-4H-benzo[d][1,3] thiazin-2-amines via palladium-catalysed isocyanide insertion in 2-bromophenylthioureas was written by Pandey, Garima;Bhowmik, Subhendu;Batra, Sanjay. And the article was included in RSC Advances in 2014.SDS of cas: 1843-21-6 This article mentions the following:

The palladium-catalyzed isocyanide insertion in 2-bromophenylthioureas resulted in the formation of 4-substituted imino-4H-benzo[d][1,3]thiazin-2-amines, e.g., I, via C-S cross coupling reaction of the intermediate imidoylpalladium species. The investigations into the substrate scope revealed that reactions of cyclohexyl isocyanide were successful with aromatic as well as aliphatic thioureas, whereas reactions of all other isocyanides (except Et 2-isocyanoacetate) were successful with aromatic thioureas only. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6SDS of cas: 1843-21-6).

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). 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.SDS of cas: 1843-21-6

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

The efficient palladium-catalyzed selective synthesis of benzenesulfonic acids was written by Jagadeesh, Rajenahally V.;Sandhya, Y. Sree;Karthikeyan, P.;Reddy, S. Sudhakar;Reddy, P. Pradeep Kumar;Kumar, M. Viniod;Charan, K. T. Prabhu;Narender, R.;Bhagat, P. R.. And the article was included in Synthetic Communications in 2011.Formula: C8H5NO2S This article mentions the following:

Palladium-catalyzed synthetic methodol. was developed for the synthesis of 2-aminobenzenesulfonic acids from benzothiazoles in good to excellent yields using chloramine-B in alk. (pH 12) acetonitrile-water (1:1) at 80 °C. In the experiment, the researchers used many compounds, for example, Benzothiazole-5-carboxylic acid (cas: 68867-17-4Formula: C8H5NO2S).

Benzothiazole-5-carboxylic acid (cas: 68867-17-4) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1).Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Formula: C8H5NO2S

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

Decreased sulfotransferase gene expression in DPT-induced polycystic kidney was written by Tanaka, Yoshihiko. And the article was included in Osaka-shi Igakkai Zasshi in 2001.Safety of 4,5-Diphenylthiazol-2-amine This article mentions the following:

Polycystic kidney is induced by feeding 1% 2-amino-4,5-diphenylthiazole (DPT) to rats. The alteration of gene expressions on the fourth day in this model was investigated with differential display method (DD). Among the bands which showed different intensities on DD, the decreased expression was confirmed by Northern blot anal. Using this PCR product as a probe, mouse kidney cDNA library was screened. Cloned cDNA of 1482 bp contained open reading frame encoding 296 amino acids, which was 94.3% identical to rat SULT1C2 sulfotransferase and was thought to be an isoform of SULT1C2. Mouse SULT1C2 mRNA was abundant in kidneys and stomachs of normal mice. The expression of SULT1C2 mRNA was decreased the day after DPT feeding and was still low after 2 wk. Although the physiol. substrate and function of SULT1C2 have yet to be elucidated, it may be involved with the sulfation of proteoglycans composing the tubular basement membranes. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Safety of 4,5-Diphenylthiazol-2-amine).

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

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

Suzuki cross-coupling reaction of aryl and heterocyclic bromides and aromatic polybromides on a Pd(II)-hydrotalcite catalyst was written by Mora, Manuel;Jimenez-Sanchidrian, Cesar;Ruiz, Jose Rafael. And the article was included in Applied Organometallic Chemistry in 2008.Formula: C9H7NS This article mentions the following:

The Suzuki cross-coupling reaction of various bromine-containing substrates and phenylboronic acid in toluene at 90 °C on a Pd(AcO)₂Py₂ catalyst supported on an Mg-Al hydrotalcite, using K₂CO₃ as the base, was studied. The conversion and selectivity results obtained for many of the substrates were excellent and similar to those provided by more active or even homogeneous catalysts. The reactions of aryl polybromides and phenylboronic acid gave the corresponding polyaromatic compounds in variable yields depending on the particular substrate. Arylation occurred in a consecutive manner by substitution of the different Br atoms. ICP-MS measurements of the palladium content of the catalyst performed prior to and after the reaction revealed that part of the metal is incorporated into the bulk solution; therefore, the catalytic process is not purely heterogeneous. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Formula: C9H7NS).

5-Phenylthiazole (cas: 1826-13-7) 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.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Formula: C9H7NS

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

CP6679, a new injectable cephalosporin. Part 1: Synthesis and structure-activity relationships was written by Tsushima, M.;Iwamatsu, K.;Umemura, E.;Kudo, T.;Sato, Y.;Shiokawa, S.;Takizawa, H.;Kano, Y.;Kobayashi, K.;Ida, T.;Tamura, A.;Atsumi, K.. And the article was included in Bioorganic & Medicinal Chemistry in 2000.Recommanded Product: 55661-33-1 This article mentions the following:

A series of cephalosporins bearing a 5,5-fused ring system, an (imidazo[5,1-b]thiazolium-6-yl)methyl group, at the C-3 position were synthesized and evaluated for in vitro antibacterial activities. CP6679 (I) and its analogs showed potent antibacterial activities against Gram-pos. and Gram-neg. bacteria, including Pseudomonas aeruginosa. They were also highly active against methicillin-resistant Staphylococcus aureus (MRSA). I showed more potent antibacterial activity than ceftazidime (CAZ) or cefpirome (CPR) against Pseudomonas aeruginosa and MRSA. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Recommanded Product: 55661-33-1).

Thiazol-2-ylmethanamine (cas: 55661-33-1) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). 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.Recommanded Product: 55661-33-1

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

Proline-Based Allosteric Inhibitors of Zika and Dengue Virus NS2B/NS3 Proteases was written by Millies, Benedikt;von Hammerstein, Franziska;Gellert, Andrea;Hammerschmidt, Stefan;Barthels, Fabian;Goeppel, Ulrike;Immerheiser, Melissa;Elgner, Fabian;Jung, Nathalie;Basic, Michael;Kersten, Christian;Kiefer, Werner;Bodem, Jochen;Hildt, Eberhard;Windbergs, Maike;Hellmich, Ute A.;Schirmeister, Tanja. And the article was included in Journal of Medicinal Chemistry in 2019.Related Products of 6294-52-6 This article mentions the following:

The NS2B/NS3 serine proteases of the Zika and Dengue flaviviruses are attractive targets for the development of antiviral drugs. We report the synthesis and evaluation of a new, proline-based compound class that displays allosteric inhibition of both proteases. The structural features relevant for protease binding and inhibition were determined to establish them as new lead compounds for flaviviral inhibitors. Based on our structure-activity relationship studies, the mols. were further optimized, leading to inhibitors with submicromolar IC₅₀ values and improved lipophilic ligand efficiency. The allosteric binding site in the proteases was probed using mutagenesis and covalent modification of the obtained cysteine mutants with maleimides, followed by computational elucidation of the possible binding modes. In infected cells, antiviral activity against Dengue virus serotype 2 using prodrugs of the inhibitors was observed In summary, a novel inhibitor scaffold targeting an allosteric site shared between flaviviral NS2B/NS3 proteases is presented whose efficacy is demonstrated in vitro and in cellulo. In the experiment, the researchers used many compounds, for example, 5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6Related Products of 6294-52-6).

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

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

Design, synthesis and biological evaluation of 2-amino-N-(2-aminophenyl)thiazole-5-carboxamide derivatives as novel Bcr-Abl and histone deacetylase dual inhibitors was written by Chen, Xin;Zhao, Shuang;Wu, Yichao;Chen, Yadong;Lu, Tao;Zhu, Yong. And the article was included in RSC Advances in 2016.Recommanded Product: 55661-33-1 This article mentions the following:

In recent studies, combinations of histone deacetylase (HDAC) inhibitors with kinase inhibitor showed additive and synergistic effects. Herein we present a novel design approach for cancer drug development by combination of breakpoint cluster Abl (Bcr-Abl) and HDAC inhibitory activity, two independent pharmacol. activities, in one mol. The designed compounds were synthesized and tested, showing inhibitory activity against Bcr-Abl and HDAC1. The representative dual Bcr-Abl/HDAC inhibitors, compounds 6a and 6m, showed potent antiproliferative activities against human leukemia cell line K562 and prostate cancer cell line DU145 in cellular assays. This work may lay the foundation for developing dual Bcr-Abl/HDAC inhibitors as potential anticancer therapeutics. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Recommanded Product: 55661-33-1).

Thiazol-2-ylmethanamine (cas: 55661-33-1) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. 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.Recommanded Product: 55661-33-1

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