Month: January 2023

Ligand free copper-catalyzed N-arylation of heteroarylamines was written by Wang, Deping;Kuang, Daizhi;Zhang, Fuxing;Liu, Yang;Ning, Shunhua. And the article was included in Tetrahedron Letters in 2014.Recommanded Product: 1843-21-6 This article mentions the following:

An efficient protocol for the ligand-free Cu-catalyzed N-arylation of heteroarylamines was developed. With the use of 1% CuI, a wide range of aryl iodides and bromides coupled with heteroarylamines affording the corresponding products in high yields. Furthermore, this protocol was particularly suitable for reactions of hindered aryl iodides with 2-aminopyridines. 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. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Recommanded Product: 1843-21-6

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

Sequencing [4+1]-Cycloaddition and Aza-Michael Addition Reactions: A Diastereoselective Cascade for the Rapid Access of Pyrido[2′,1′:2,3]/Thiazolo[2′,3′:2,3]imidazo[1,5-a]quinolone Scaffolds as Potential Antibacterial and Anticancer Motifs was written by Srinivasulu, Vunnam;Khanfar, Monther;Omar, Hany A.;ElAwady, Raafat;Sieburth, Scott McN;Sebastian, Anusha;Zaher, Dana M.;Al-Marzooq, Farah;Hersi, Fatema;Al-Tel, Taleb H.. And the article was included in Journal of Organic Chemistry in 2019.Category: thiazole This article mentions the following:

The design and synthesis of a quality compound library containing a small number of skeletally diverse scaffolds, whose members rapidly deliver new chem. probes active against multiple phenotypes, is paramount in drug discovery. In this context, an efficient one-pot strategy for the synthesis of a mini library of sp3 enriched hexahydropyrido[2′,1′:2,3]imidazo[1,5-a]quinolinium and hexahydrothiazolo[2′,3′:2,3] imidazo[1,5-a]quinolinium architectures, is described. This new one-pot method features a combination of Sc(OTf)3-catalyzed [4+1]-cycloaddition with aza-Michael addition reactions.The cascade results in a rapid and diastereoselective formation of these scaffolds via desymmetrization of the oxidative-dearomatization products of phenols. Phenotypic screening of the mini library against multidrug resistant bacteria and a panel of cancer cell lines identified potential antibacterial and anticancer lead drug candidates.Further investigation of the anticancer leads, indicated their activity as tubulin-polymerization inhibitors, representing a promising approach for cancer therapy. 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. The thiazole ring has been identified as a central feature of numerous natural products, perhaps the most famous example of which is epothilone. 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.Category: thiazole

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

Use of a Pharmacophore Model To Discover a New Class of Influenza Endonuclease Inhibitors was written by Parkes, Kevin E. B.;Ermert, Philipp;Faessler, Juerg;Ives, Jane;Martin, Joseph A.;Merrett, John H.;Obrecht, Daniel;Williams, Glyn;Klumpp, Klaus. And the article was included in Journal of Medicinal Chemistry in 2003.Application In Synthesis of 2-Acetamido-4-methylthiazole-5-sulfonyl chloride This article mentions the following:

Data from both our own and literature studies of the biochem. and inhibition of influenza virus endonuclease was combined with data on the mechanism of action and the likely active site mechanism to propose a pharmacophore. The pharmacophore was used to design a novel structural class of inhibitors, some of which were found to have activities similar to that of known influenza endonuclease inhibitors and were also antiviral in cell culture. In the experiment, the researchers used many compounds, for example, 2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9Application In Synthesis of 2-Acetamido-4-methylthiazole-5-sulfonyl chloride).

2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9) 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. 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.Application In Synthesis of 2-Acetamido-4-methylthiazole-5-sulfonyl chloride

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

Ruthenium Catalyzed Intramolecular C-S Coupling Reactions: Synthetic Scope and Mechanistic Insight was written by Sharma, Shivani;Pathare, Ramdas S.;Maurya, Antim K.;Gopal, Kandasamy;Roy, Tapta Kanchan;Sawant, Devesh M.;Pardasani, Ram T.. And the article was included in Organic Letters in 2016.Reference of 1843-21-6 This article mentions the following:

A ruthenium-catalyzed intramol. C-S coupling reaction of N-arylthioureas for the synthesis of 2-aminobenzothiazoles has been developed. Kinetic, isotope labeling, and computational studies reveal the involvement of an electrophilic ruthenation pathway instead of a direct C-H activation. Stereoelectronic effect of meta-substituents on the N-arylthiourea dictates the final regioselective outcome of the reaction. 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. 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 1843-21-6

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

Identification of ortho-amino benzamides and nicotinamides as MCHr1 antagonists was written by Vasudevan, Anil;LaMarche, Matthew J.;Blackburn, Christopher;Che, Jennifer Lee;Luchaco-Cullis, Courtney A.;Lai, Sujen;Marsilje, Thomas H.;Patane, Michael A.;Souers, Andrew J.;Wodka, Derek;Geddes, Bradley;Chen, Sumiao;Brodjian, Seven;Falls, Doug H.;Dayton, Brian D.;Bush, Eugene;Brune, Michael;Shapiro, Robin D.;Marsh, Kennan C.;Hernandez, Lisa E.;Sham, Hing L.;Collins, Christine A.;Kym, Philip R.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2005.Recommanded Product: 55661-33-1 This article mentions the following:

Several potent and efficacious MCHr1 antagonists containing an ortho-amino benzamide or nicotinamide chemotype have been identified, exemplified by compounds (I) and (II). 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. 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. 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

Mechanochemical solid-state synthesis of 2-aminothiazoles, quinoxalines and benzoylbenzofurans from ketones by one-pot sequential acid- and base-mediated reactions was written by Nagarajaiah, Honnappa;Mishra, Abhaya Kumar;Moorthy, Jarugu Narasimha. And the article was included in Organic & Biomolecular Chemistry in 2016.Application In Synthesis of 4,5-Diphenylthiazol-2-amine This article mentions the following:

Mechanochem. solid-state synthesis of 2-aminothiazoles, 2-hydrazinylthiazoles, quinoxalines and benzoylbenzofurans via one-pot sequential α-chlorination of ketones followed by base-mediated condensations with thiourea/thiosemicarbazides, o-phenylenediamine and salicylaldehyde resp. under ball-milling conditions was described. Chlorination of ketones proceeded with atom-economical trichloroisocyanuric acid reagent in the presence of p-TSA under ball-milling conditions to give α-chloroketones which was then further used without isolation. The viability of one-pot sequential acid- and base-mediated reactions in the solid state under ball-milling conditions was thus demonstrated. 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. 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.Application In Synthesis of 4,5-Diphenylthiazol-2-amine

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

Rapid Access to a Broad Range of 6′-Substituted Firefly Luciferin Analogues Reveals Surprising Emitters and Inhibitors was written by Sharma, Deepak K.;Adams, Spencer T.;Liebmann, Kate L.;Miller, Stephen C.. And the article was included in Organic Letters in 2017.Recommanded Product: 80945-86-4 This article mentions the following:

Light-emitting firefly luciferin analogs contain electron-donating groups in the 6′-position, but the scope of known 6′-substitution remains narrow. A two-step route to a broad range of 6′-substituted luciferin analogs was developed to fill this void and enable more extensive study of the 6′-functionality. This chem. allowed direct access to “caged” amide and bright azetidine analogs, but also revealed thioether inhibitors and unexpectedly luminogenic aryl amine derivatives In the experiment, the researchers used many compounds, for example, 6-Bromo-2-chlorobenzothiazole (cas: 80945-86-4Recommanded Product: 80945-86-4).

6-Bromo-2-chlorobenzothiazole (cas: 80945-86-4) 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.Recommanded Product: 80945-86-4

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

Copper-catalyzed synthesis of 2-aminophenyl benzothiazoles: a novel approach was written by Boddapati, S. N. Murthy;Kurmarayuni, Chandra Mohan;Mutchu, Baby Ramana;Tamminana, Ramana;Bollikolla, Hari Babu. And the article was included in Organic & Biomolecular Chemistry in 2018.COA of Formula: C13H10N2S This article mentions the following:

A novel, convenient and efficient protocol for the construction of various 2-aminophenyl benzothiazoles by domino intra- and intermol. C-N cross-coupling reactions of arylisothioureas with aryl iodides using an inexpensive, air stable and readily available copper catalyst was described. The arylisothioureas were obtained from thiourea via copper promoted desulfurization followed by nucleophilic substitution. In addition, the reactivity of arylhalides and the reaction mechanism were studied. The protocol featured operational simplicity and a broad substrate scope. 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 in peptides or their ability to bind proteins, DNA and RNA has led to many synthetic studies and new applications. 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

Novel and Potent Dopamine D₂ Receptor Go-Protein Biased Agonists was written by Bonifazi, Alessandro;Yano, Hideaki;Guerrero, Adrian M.;Kumar, Vivek;Hoffman, Alexander F.;Lupica, Carl R.;Shi, Lei;Newman, Amy Hauck. And the article was included in ACS Pharmacology & Translational Science in 2019.SDS of cas: 68867-17-4 This article mentions the following:

The discovery of functionally biased and physiol. beneficial ligands directed toward G-protein coupled receptors (GPCRs) has provided the impetus to design dopamine D₂ receptor (D₂R) targeted mols. that may be therapeutically advantageous for the treatment of certain neuropsychiatric or basal ganglia related disorders. Here we describe the synthesis of a novel series of D₂R agonists linking the D₂R unbiased agonist sumanirole with privileged secondary mol. fragments. The resulting ligands demonstrate improved D₂R affinity and selectivity over sumanirole. Extensive in vitro functional studies and bias factor anal. led to the identification of a novel class of highly potent Go-protein biased full D₂R agonists with more than 10-fold and 1000-fold bias selectivity toward activation of specific G-protein subtypes and β-arrestin, resp. Intracellular electrophysiol. recordings from midbrain dopamine neurons demonstrated that Go-protein selective agonists can elicit prolonged ligand-induced GIRK activity via D₂Rs, which may be beneficial in the treatment of dyskinesias associated with dopamine system dysfunction. In the experiment, the researchers used many compounds, for example, Benzothiazole-5-carboxylic acid (cas: 68867-17-4SDS of cas: 68867-17-4).

Benzothiazole-5-carboxylic acid (cas: 68867-17-4) 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.SDS of cas: 68867-17-4

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

Synthesis of 5-Phenylthiazolamines by Using Thiourea as an α-Bromination Shuttle was written by Roslan, Irwan Iskandar;Ng, Kian-Hong;Chuah, Gaik-Khuan;Jaenicke, Stephan. And the article was included in European Journal of Organic Chemistry in 2017.Electric Literature of C15H12N2S This article mentions the following:

A straightforward synthesis of 5-phenylthiazolamines by coupling thiourea with phenylacetones, phenylacetophenones, and β-tetralone has been developed. Thiourea acts as a substrate and an α-bromination shuttle by transferring a Br atom from CBrCl₃ to the α-carbon of the carbonyl moiety. A series of steps are then triggered to reach the final product. Isolated yields from 80 to 95 % were obtained. Key features of this protocol include its minimal use of reagents (i.e., substrates, CBrCl₃, and CsHCO₃), its short reaction times under mild conditions (at 80 °C for 2-3 h), and its ease of scale up to prepare gram quantities of product. 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. 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.Electric Literature of C15H12N2S

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