Tag: 100-200

Shibahara, Fumitoshi et al. published their research in Journal of Organic Chemistry in 2011 | CAS: 1826-13-7

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. 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 of 1826-13-7

Direct Arylation of Simple Azoles Catalyzed by 1,10-Phenanthroline Containing Palladium Complexes: An Investigation of C4 Arylation of Azoles and the Synthesis of Triarylated Azoles by Sequential Arylation was written by Shibahara, Fumitoshi;Yamaguchi, Eiji;Murai, Toshiaki. And the article was included in Journal of Organic Chemistry in 2011.Application of 1826-13-7 This article mentions the following:

Direct triarylation and sequential triarylation reactions of simple azoles catalyzed by [Pd(phen)2](PF6)2 are described. Simple azoles, such as N-methylimidazole, thiazole, and oxazole, were observed to undergo triarylation reactions even at their C4 positions when treated with aryl iodides in the presence of [Pd(phen)2](PF6)2 as a catalyst and a stoichiometric amount of Cs2CO3 in DMA at 150 °C. Using excess amounts of azoles, selective C5 monoarylation was achieved by using the same catalytic system. Subsequent efforts demonstrated that C5 arylated azoles undergo exclusive C2 arylation using [Pd(phen)2](PF6)2 as the catalyst with galvinoxyl as an additive. Finally, unprecedented C4 arylation reactions of 2,5-diarylazoles occur by using the new catalytic system to give the corresponding triarylated products in good to excellent yields. The results of mechanistic studies suggest that the C2 arylation process takes place by way of an electrophilic aromatic substitution (SEAr) palladation pathway, while arylation reactions at the C4 position occur via a SEAr palladation and/or radical mechanism. Finally, a concise, three-step synthesis of the Tie-2 Tyrosine Kinase Inhibitor has been executed starting with com. available N-methylimidazole by a route that employs the new sequential arylation process. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Application of 1826-13-7).

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. 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 of 1826-13-7

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

Galasso, V. et al. published their research in Tetrahedron in 1972 | CAS: 1826-13-7

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

Conformational analysis and electronic structure of phenylthiazoles and their protonated forms was written by Galasso, V.;Trinajstic, N.. And the article was included in Tetrahedron in 1972.Application of 1826-13-7 This article mentions the following:

The most probable conformation of 2-, 4-, and 5-phenylthiazole and their protonated forms was investigated using the extended Hueckel MO approach and it was found to be non-planar, the angle of twist about the interring linkage increasing in the order: 4- < 2- < 5-. For the energetically most favorable geometry the charge distribution calculated using the CNDO/2 (complete neglect of differential overlap) method is found to be consistent with the observed dipole moment. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Application of 1826-13-7).

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

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

Vernin, Gaston et al. published their research in Chimie Analytique (Paris) in 1964 | CAS: 1826-13-7

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

Thin-layer chromatography of thiazole derivatives was written by Vernin, Gaston;Metzger, Jacques. And the article was included in Chimie Analytique (Paris) in 1964.Electric Literature of C9H7NS This article mentions the following:

A series of thiazoles having Cl, SMe, OH, NH2, or SH in the 2-position and phenyl, p-tolyl, p-bromophenyl, p-chlorophenyl, p-methoxyphenyl, or p-nitrophenyl in the 4-position are separated by thin-layer chromatography on silica gel using heptane or benzene as the eluting solvent. Some 2, 4, 5-trisubstituted thiazoles were also tried. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Electric Literature of C9H7NS).

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

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

Primas, Nicolas et al. published their research in Tetrahedron in 2009 | CAS: 1826-13-7

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

Synthesis of 5-arylthiazoles. Comparative study between Suzuki cross-coupling reaction and direct arylation was written by Primas, Nicolas;Bouillon, Alexandre;Lancelot, Jean-Charles;El-Kashef, Hussein;Rault, Sylvain. And the article was included in Tetrahedron in 2009.HPLC of Formula: 1826-13-7 This article mentions the following:

A facile synthetic route to the thiazol-5-ylboronic acid pinacol ester was described herein. Its reactivity toward Suzuki cross-coupling reaction was studied to provide various 5-arylthiazoles. A comparative study between Suzuki cross-coupling reactions and palladium-catalyzed C5-H direct arylation on thiazole ring was achieved. 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. 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.HPLC of Formula: 1826-13-7

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

Fan, Shilu et al. published their research in Organic Letters in 2012 | CAS: 1826-13-7

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

Copper-Catalyzed Dehydrogenative Cross-Coupling of Benzothiazoles with Thiazoles and Polyfluoroarene was written by Fan, Shilu;Chen, Zhao;Zhang, Xingang. And the article was included in Organic Letters in 2012.Computed Properties of C9H7NS This article mentions the following:

A copper-catalyzed dehydrogenative cross-coupling of benzothiazoles with thiazoles and polyfluoroarene under mild reaction conditions is described. E.g., in presence of CuI, Ag2CO3, and t-BuOLi, cross-coupling reaction of benzothiazole and 4,5-dimethylthiazole gave 71% I and 14% of the benzothiazole homocoupling product. This protocol provides a straightforward and operationally simple method for the synthesis of the 2,2′-linkage of thiazoles and 2-polyfluoroarylthiazoles of interest in life and material sciences. 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. 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 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.Computed Properties of C9H7NS

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

Perez, Christian et al. published their research in Journal of Medicinal Chemistry in 2017 | CAS: 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.Computed Properties of C4H6N2S

Discovery of an Inhibitor of the Proteasome Subunit Rpn11 was written by Perez, Christian;Li, Jing;Parlati, Francesco;Rouffet, Matthieu;Ma, Yuyong;Mackinnon, Andrew L.;Chou, Tsui-Fen;Deshaies, Raymond J.;Cohen, Seth M.. And the article was included in Journal of Medicinal Chemistry in 2017.Computed Properties of C4H6N2S This article mentions the following:

The proteasome plays a crucial role in degradation of normal proteins that happen to be constitutively or inducibly unstable, and in this capacity it plays a regulatory role. Addnl., it degrades abnormal/damaged/mutant/misfolded proteins, which serves a quality-control function. Inhibitors of the proteasome have been validated in the treatment of multiple myeloma, with several FDA-approved therapeutics. Rpn11 is a Zn2+-dependent metallo-isopeptidase that hydrolyzes ubiquitin from tagged proteins that are trafficked to the proteasome for degradation A fragment-based drug discovery (FBDD) approach was utilized to identify fragments with activity against Rpn11. Screening of a library of metal-binding pharmacophores (MBPs) revealed that 8-thioquinoline (8TQ, IC50 value ∼2.5 μM) displayed strong inhibition of Rpn11. Further synthetic elaboration of 8TQ yielded a small mol. compound I (IC50 value ∼300 nM) that is a potent and selective inhibitor of Rpn11 that blocks proliferation of tumor cells in culture. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Computed Properties of C4H6N2S).

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.Computed Properties of C4H6N2S

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

Bosco, Marcella et al. published their research in Journal of the Chemical Society in 1976 | CAS: 1826-13-7

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. 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.Computed Properties of C9H7NS

Relative reactivity of groups bonded to positions 2 and 5 of the thiazole ring was written by Bosco, Marcella;Forlani, Luciano;Todesco, Paolo E.;Troisi, Luigi. And the article was included in Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999) in 1976.Computed Properties of C9H7NS This article mentions the following:

The substitution of halogen by MeO-, MeS- and PhS- ions and oxidation of phenylsulfinyl to phenylsulfonyl by PhC(O)OOH at positions 2 and 5 of the thiazole ring were studied quant. The ratio of the reactivities of the positions was moderate and the unusual nucleophilic halogen displacement for 5-halothiazoles together with the oxidation of the 5-sulfinyl groups indicated the slightly pos. character of C-5. 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. 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.Computed Properties of C9H7NS

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

Shibahara, Fumitoshi et al. published their research in Journal of Organic Chemistry in 2011 | CAS: 1826-13-7

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. 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 of 1826-13-7

Direct Arylation of Simple Azoles Catalyzed by 1,10-Phenanthroline Containing Palladium Complexes: An Investigation of C4 Arylation of Azoles and the Synthesis of Triarylated Azoles by Sequential Arylation was written by Shibahara, Fumitoshi;Yamaguchi, Eiji;Murai, Toshiaki. And the article was included in Journal of Organic Chemistry in 2011.Application of 1826-13-7 This article mentions the following:

Direct triarylation and sequential triarylation reactions of simple azoles catalyzed by [Pd(phen)2](PF6)2 are described. Simple azoles, such as N-methylimidazole, thiazole, and oxazole, were observed to undergo triarylation reactions even at their C4 positions when treated with aryl iodides in the presence of [Pd(phen)2](PF6)2 as a catalyst and a stoichiometric amount of Cs2CO3 in DMA at 150 °C. Using excess amounts of azoles, selective C5 monoarylation was achieved by using the same catalytic system. Subsequent efforts demonstrated that C5 arylated azoles undergo exclusive C2 arylation using [Pd(phen)2](PF6)2 as the catalyst with galvinoxyl as an additive. Finally, unprecedented C4 arylation reactions of 2,5-diarylazoles occur by using the new catalytic system to give the corresponding triarylated products in good to excellent yields. The results of mechanistic studies suggest that the C2 arylation process takes place by way of an electrophilic aromatic substitution (SEAr) palladation pathway, while arylation reactions at the C4 position occur via a SEAr palladation and/or radical mechanism. Finally, a concise, three-step synthesis of the Tie-2 Tyrosine Kinase Inhibitor has been executed starting with com. available N-methylimidazole by a route that employs the new sequential arylation process. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Application of 1826-13-7).

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. 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 of 1826-13-7

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

Galasso, V. et al. published their research in Tetrahedron in 1972 | CAS: 1826-13-7

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

Conformational analysis and electronic structure of phenylthiazoles and their protonated forms was written by Galasso, V.;Trinajstic, N.. And the article was included in Tetrahedron in 1972.Application of 1826-13-7 This article mentions the following:

The most probable conformation of 2-, 4-, and 5-phenylthiazole and their protonated forms was investigated using the extended Hueckel MO approach and it was found to be non-planar, the angle of twist about the interring linkage increasing in the order: 4- < 2- < 5-. For the energetically most favorable geometry the charge distribution calculated using the CNDO/2 (complete neglect of differential overlap) method is found to be consistent with the observed dipole moment. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Application of 1826-13-7).

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

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

Vernin, Gaston et al. published their research in Chimie Analytique (Paris) in 1964 | CAS: 1826-13-7

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

Thin-layer chromatography of thiazole derivatives was written by Vernin, Gaston;Metzger, Jacques. And the article was included in Chimie Analytique (Paris) in 1964.Electric Literature of C9H7NS This article mentions the following:

A series of thiazoles having Cl, SMe, OH, NH2, or SH in the 2-position and phenyl, p-tolyl, p-bromophenyl, p-chlorophenyl, p-methoxyphenyl, or p-nitrophenyl in the 4-position are separated by thin-layer chromatography on silica gel using heptane or benzene as the eluting solvent. Some 2, 4, 5-trisubstituted thiazoles were also tried. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Electric Literature of C9H7NS).

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

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