Tag: 100-200

Cobalt-catalyzed alkenylation of thiazoles with alkynes via C-H bond functionalization was written by Ding, Zhenhua;Yoshikai, Naohiko. And the article was included in Synthesis in 2011.Computed Properties of C9H7NS This article mentions the following:

A cobalt-Xantphos catalyst has been developed for the syn addition of (benzo)thiazoles to internal alkynes via C-H bond functionalization. The reaction affords C2-alkenylated (benzo)thiazoles with high regio- and stereoselectivities under mild conditions. E.g., reaction of 4,5-dimethylthiazole and oct-2-yne, catalyzed by CoBr₂-Xantphos, gave 90% (E)-4,5-dimethyl-2-(oct-4-en-4-yl)thiazole (I). In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Computed Properties of C9H7NS).

5-Phenylthiazole (cas: 1826-13-7) 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.Computed Properties of C9H7NS

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

The discovery of N-(1,3-thiazol-2-yl)pyridin-2-amines as potent inhibitors of KDR kinase was written by Bilodeau, Mark T.;Rodman, Leonard D.;McGaughey, Georgia B.;Coll, Kathleen E.;Koester, Timothy J.;Hoffman, William F.;Hungate, Randall W.;Kendall, Richard L.;McFall, Rosemary C.;Rickert, Keith W.;Rutledge, Ruth Z.;Thomas, Kenneth A.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2004.Product Details of 329794-40-3 This article mentions the following:

An azo-dye lead was modified to a N-(1,3-thiazol-2-yl)pyridin-2-amine series of KDR kinase inhibitors through the use of rapid analog libraries. The two lead compounds were N-butyl-N,3-dimethyl-4-[(5-nitro-2-thiazolyl)azo]benzenamine and N-(5-phenyl-2-thiazolyl)benzamide. This class has been found to be potent, selective, and of low mol. weight Mol. modeling has postulated an interesting conformational preference and binding mode for these compounds in the active site of the enzyme. A binding mode was proposed for the lead compound N-(5-phenyl-2-thiazolyl)-2-pyridinamine (I) in the KDR kinase active site. In the experiment, the researchers used many compounds, for example, 2-Chloro-5-phenylthiazole (cas: 329794-40-3Product Details of 329794-40-3).

2-Chloro-5-phenylthiazole (cas: 329794-40-3) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. 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.Product Details of 329794-40-3

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

Synthesis of α-phosphoramidate containing benzothiazole group was written by Xu, Xue-li;Song, Wei;Gao, Wei-xia. And the article was included in Huaxue Shiji in 2014.SDS of cas: 68867-17-4 This article mentions the following:

This work is designed to use 3-nitro-4-thiosalicylic acid as the substrate, which was taken to cyclization, esterification, reduction, oxidation and the addition reactions, it was 6 steps in all. 14α-Phosphoramidates e. g., I, which contained benzothiazole groups were synthesized. And the products were confirmed by m.p., NMR, MS and IR. 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 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.SDS of cas: 68867-17-4

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

Alkylation of camphor and pinanone imines of 2-(aminomethyl)thiazole. Enantioselective synthesis of 2-(1-aminoalkyl)thiazoles was written by Dondoni, Alessandro;Merchan, Francisco L.;Merino, Pedro;Rojo, Isabel;Tejero, Tomas. And the article was included in Synthesis in 1996.Formula: C4H6N2S This article mentions the following:

A method for the enantioselective synthesis of (aminoalkyl)thiazoles I (R = PhCH₂, allyl,cyclohexylmethyl, Me, 4-ClC₆H₄CH₂) via stereoselective alkylation of the imines of (+)-(R)-camphor or (-)-(1S,2S,5S)-2-hydroxy-3-pinanone and 2-thiazolemethanamine is described. Compounds I served as α-amino aldehyde precursors via thiazolyl-to-formyl conversion. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Formula: C4H6N2S).

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. 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.Formula: C4H6N2S

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

Asymmetric Synthesis of Heterocyclic Chloroamines and Aziridines by Enantioselective Protonation of Catalytically Generated Enamines was written by McLean, Liam A.;Ashford, Matthew W.;Fyfe, James W. B.;Slawin, Alexandra M. Z.;Leach, Andrew G.;Watson, Allan J. B.. And the article was included in Chemistry – A European Journal in 2022.Category: thiazole This article mentions the following:

A method for the synthesis of chiral vicinal chloroamines RCH(Cl)CH₂NHR¹ [R = 2-quinolyl, quinazolin-2-yl, 1,3-benzothiazol-2-yl, etc.; R¹ = Ph, 4-MeC₆H₄, benzothiophen-5-yl, etc.] via asym. protonation of catalytically generated prochiral chloroenamines using chiral Bronsted acids was reported. The process was highly enantioselective, with the origin of asymmetry and catalyst substituent effects elucidated by DFT calculations The utility of the method showed as an approach to the synthesis of a broad range of heterocycle-substituted aziridines I [R² = 2-quinolyl, quinoxalin-2-yl, 5-cyano-2-pyridyl, etc.; Ar = Ph, 4-MeOC₆H₄, 3-BrC₆H₄, etc.] by treatment of the chloroamines with base in a one-pot process, as well as the utility of the process to allow access to vicinal diamines II [R³ = 4-tert-butoxycarbonylpiperazin-1-yl, morpholino, thiomorpholino]. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Category: thiazole).

5-Phenylthiazole (cas: 1826-13-7) 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 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.Category: thiazole

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

Novel and Efficient Synthesis of Benzimidazole and Benzthiazole Moieties Mediated by Triflic Anhydride and 2-Nitropyridine was written by Quadri, Syed Aziz Imam;Das, Tonmoy C.;Farooqui, Mazahar. And the article was included in ChemistrySelect in 2017.Computed Properties of C7H4ClNOS This article mentions the following:

In the present report, inter and intramol. C-N bond formation between the carbonyl carbon of urea or amide functional group with various amines, e.g., I, mediated by triflic anhydride and 2-nitropyridine is successfully investigated for the first time. The versatility of the method is demonstrated by exploring it on a wide range of substrates to synthesize diversified 2-aminobenzimidazoles II [Y = NH; R = H; R¹ = 4-ClC₆H₄NH, 1H-pyrazol-1-yl, 1H-indazol-1-yl, etc.], 2-aminobenzothiazoles II [Y = S; R = H, Cl; R¹ 2-O₂N-4-F₃CC₆H₃NH, 4-CN-3-F₃CC₆H₃, [6-cyano-5-(trifluoromethyl)pyridin-3-yl]aminyl, etc.], 2-aminopyridoimidazoles III [R³ = H, Cl; X = N; Z = NH₂; R² = C₂H₅, (CH₃)₂CHCH₂] and 2-substituted benzimidazoles III [X = CH; R = H; R² = Me, Et, Pr, (CH₃)₃CCH₂; Z = Cy, furan-2-yl, 4-BrC₆H₄, etc.]. Short reaction time, high yields and applicability in milder metal free reaction conditions are the highlights of the present methodol. In the experiment, the researchers used many compounds, for example, 6-Chlorobenzo[d]thiazol-2(3H)-one (cas: 62266-81-3Computed Properties of C7H4ClNOS).

6-Chlorobenzo[d]thiazol-2(3H)-one (cas: 62266-81-3) 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.Computed Properties of C7H4ClNOS

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

Applications of Snyder’s theory on linear adsorption chromatography to heterocyclic compounds. I. Influence of the polar and steric effects of various substituents on the adsorption energy of thiazoles on alumina was written by Vernin, Gaston;Vernin, G. Mrs.. And the article was included in Journal of Chromatography in 1970.HPLC of Formula: 1826-13-7 This article mentions the following:

The Snyder theory of linear adsorption chromatog., that was applied to on e hundred thiazole derivatives, made it possible to determine exptl. the adsorption energies of the compounds and to compare these with the adsorption energies calculated by means of fixed tables. In a study on thiazoles containing one or two alkyl groups, this comparison made it possible to determine the variations in adsorption energy of the N atom of the ring due to the polarization effects and to the steric effects induced by the alkyl groups and to relate these effects to the constant relations which exist between the polarization and steric effects of the substituents. A similar investigation was made on 4-aryl thiazoles with various substituents in the 2-position. In this case variations in the adsorption energy of the mols. due to the polarization effects of the groups substituted para to the phenyl group with respect to the substituents in the 2-position were studied, and the mutual electronic interactions between the various groups were determined In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7HPLC of Formula: 1826-13-7).

5-Phenylthiazole (cas: 1826-13-7) 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. 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.HPLC of Formula: 1826-13-7

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

Vinblastine 20′ Amides: Synthetic Analogues That Maintain or Improve Potency and Simultaneously Overcome Pgp-Derived Efflux and Resistance was written by Lukesh, John C.;Carney, Daniel W.;Dong, Huijun;Cross, R. Matthew;Shukla, Vyom;Duncan, Katharine K.;Yang, Shouliang;Brody, Daniel M.;Brutsch, Manuela M.;Radakovic, Aleksandar;Boger, Dale L.. And the article was included in Journal of Medicinal Chemistry in 2017.Safety of Benzothiazole-5-carboxylic acid This article mentions the following:

A series of 180 vinblastine 20′ amides were prepared in three steps from com. available starting materials, systematically exploring a typically inaccessible site in the mol. enlisting a powerful functionalization strategy. Clear structure-activity relationships and a structural model were developed in the studies which provided many such 20′ amides that exhibit substantial and some even remarkable enhancements in potency, many that exhibit further improvements in activity against a Pgp overexpressing resistant cancer cell line, and an important subset of the vinblastine analogs that display little or no differential in activity against a matched pair of vinblastine sensitive and resistant (Pgp overexpressing) cell lines. The improvements in potency directly correlated with target tubulin binding affinity, and the reduction in differential functional activity against the sensitive and Pgp overexpressing resistant cell lines was found to correlate directly with an impact on Pgp-derived efflux. In the experiment, the researchers used many compounds, for example, Benzothiazole-5-carboxylic acid (cas: 68867-17-4Safety of Benzothiazole-5-carboxylic acid).

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

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

Synthesis and in vitro evaluation of 5-substituted benzovesamicol analogs containing N-substituted amides as potential positron emission tomography tracers for the vesicular acetylcholine transporter was written by Roslin, Sara;De Rosa, Maria;Deuther-Conrad, Winnie;Eriksson, Jonas;Odell, Luke R.;Antoni, Gunnar;Brust, Peter;Larhed, Mats. And the article was included in Bioorganic & Medicinal Chemistry in 2017.Recommanded Product: 55661-33-1 This article mentions the following:

Herein, new ligands for the vesicular acetylcholine transporter (VAChT), based on a benzovesamicol scaffold, are presented. VAChT is acknowledged as a marker for cholinergic neurons and a positron emission tomog. tracer for VAChT could serve as a tool for quant. anal. of cholinergic neuronal d. With an easily accessible triflate precursor, aminocarbonylations were utilized to evaluate the chem. space around the C5 position on the tetrahydronaphthol ring. Synthesized ligands were evaluated for their affinity and selectivity for VAChT. Small, preferably aromatic, N-substituents proved to be more potent than larger substituents. Of the fifteen compounds synthesized, benzyl derivatives (±)-7i and (±)-7l had the highest affinities for VAChT. Compound (±)-7i was chosen to investigate the importance of stereochem. for binding to VAChT and selectivity toward the σ₁ and σ₂ receptors. Enantiomeric resolution gave (+)-7i and (-)-7i, and the eutomer showed seven times better affinity. Although racemate (±)-7i was initially promising, the affinity of (-)-7i for VAChT was not better than 56.7 nM which precludes further preclin. evaluation. However, the nanomolar binding together with the ready synthesis of [¹¹C]-(±)-7i shows that (-)-7i can serve as a scaffold for future optimizations to provide improved ¹¹C-labeled VAChT PET tracers. 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. 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.Recommanded Product: 55661-33-1

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