Day: January 5, 2023

Efficient and facile strategy to substituted 2-aminothiazoles via ring opening of α-nitroepoxides was written by Zhu, Yue;Wang, Qilin;Luo, Haofan;Zhang, Guolin;Yu, Yongping. And the article was included in Tetrahedron in 2018.Synthetic Route of C15H12N2S This article mentions the following:

A novel and efficient reaction has been developed to synthesize a set of substituted 2-aminothiazoles I (R¹=Phenyl, 4-fluorophenyl, 3-fluorophenyl etc. R²=Methyl, Et, phenyl) from α-nitroepoxides and ammonium thiocyanate. This reaction could proceed smoothly at mild condition, to afford products for a wide range of substrates with good to excellent yields. A possible mechanism has also been proposed. 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. 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.Synthetic Route of C15H12N2S

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

Iron-catalyzed tandem reactions of ortho-aminobenzenethiols with isothiocyanates leading to 2-aminobenzothiazoles under ligand- and solvent-free conditions was written by Ding, Qiuping;Cao, Banpeng;Yang, Qin;Liu, Xianjin;Peng, Yiyuan. And the article was included in Phosphorus, Sulfur and Silicon and the Related Elements in 2011.Formula: C13H10N2S This article mentions the following:

An efficient route to the synthesis of a variety of 2-aminobenzothiazoles I (R¹ = H, MeO, Br, I; R² = Ph, Et, 4-O₂NC₆H₄, cyclohexyl, etc.) has been discovered. It involves the reaction of ortho-aminobenzenethiols with isothiocyanates via an iron-catalyzed tandem addition-annulation process under ligand and solvent free conditions on a silica gel surface. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Formula: 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.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Formula: C13H10N2S

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

Discovery of Novel Small Molecules that Activate Satellite Cell Proliferation and Enhance Repair of Damaged Muscle was written by Billin, Andrew N.;Bantscheff, Marcus;Drewes, Gerard;Ghidelli-Disse, Sonja;Holt, Jason A.;Kramer, Henning F.;McDougal, Alan J.;Smalley, Terry L.;Wells, Carrow W.;Zuercher, William J.;Henke, Brad R.. And the article was included in ACS Chemical Biology in 2016.Safety of Thiazol-2-ylmethanamine This article mentions the following:

Skeletal muscle progenitor stem cells (referred to as satellite cells) represent the primary pool of stem cells in adult skeletal muscle responsible for the generation of new skeletal muscle in response to injury. Satellite cells derived from aged muscle display a significant reduction in regenerative capacity to form functional muscle. This decrease in functional recovery has been attributed to a decrease in proliferative capacity of satellite cells. Hence, agents that enhance the proliferative abilities of satellite cells may hold promise as therapies for a variety of pathol. settings, including repair of injured muscle and age- or disease-associated muscle wasting. Through phenotypic screening of isolated murine satellite cells, we identified a series of 2,4-diaminopyrimidines (e.g., 2) that increased satellite cell proliferation. Importantly, compound 2 was effective in accelerating repair of damaged skeletal muscle in an in vivo mouse model of skeletal muscle injury. While these compounds were originally prepared as c-Jun N-terminal kinase 1 (JNK-1) inhibitors, structure-activity analyses indicated JNK-1 inhibition does not correlate with satellite cell activity. Screening against a broad panel of kinases did not result in identification of an obvious mol. target, so we conducted cell-based proteomics experiments in an attempt to identify the mol. target(s) responsible for the potentiation of the satellite cell proliferation. These data provide the foundation for future efforts to design improved small mols. as potential therapeutics for muscle repair and regeneration. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Safety of Thiazol-2-ylmethanamine).

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. 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 Thiazol-2-ylmethanamine

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

Lewis Acid-Catalyzed, Copper(II)-Mediated Synthesis of Heteroaryl Thioethers under Base-Free Conditions was written by Dai, Chao;Xu, Zhaoqing;Huang, Fei;Yu, Zhengkun;Gao, Yan-Feng. And the article was included in Journal of Organic Chemistry in 2012.Application In Synthesis of 5-Phenylthiazole This article mentions the following:

A Lewis acid (Ag^I, Ni^II, or Fe^II) catalyzed, Cu^II-mediated thiolation reaction between heteroarenes and thiols was achieved with good yield under base-free conditions. DMSO could serve as an effective methylthiolation reagent for the synthesis of heterocyclic Me thioethers. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Application In Synthesis of 5-Phenylthiazole).

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. 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 5-Phenylthiazole

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

Oxidation potentials and ionization potentials of some phenyl derivatives of thiazole was written by Bonnier, Jane Marie;Arnaud, Roger;Maurey-Mey, Monique. And the article was included in Comptes Rendus des Seances de l’Academie des Sciences, Serie C: Sciences Chimiques in 1968.HPLC of Formula: 1826-13-7 This article mentions the following:

The half-wave oxidation potentials and the ionization potentials (determined from the charge transfer of the complexes and by the Hueckel method) are given for thiazole, 2-, 4-, and 5-phenylthiazole, 2,4-, 2,5-, and 4,5-diphenylthiazole, 2-phenyl-4-biphenylylthiazole, 4-phenyl-2-biphenylylthiazole, and 2,4-bis(biphenylyl)thiazole. A linear relation existed between the ionization potentials and the halfwave oxidation potentials. 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 are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. 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.HPLC of Formula: 1826-13-7

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

Design, synthesis, and biological evaluation of 2-substituted ethenesulfonic acid ester derivatives as selective PTP1B inhibitors was written by Liu, Jingbao;Deng, Xinxian;Jin, Yan;Xu, Buzhe;Liu, Wenlu;Jiang, Faqin;Fu, Lei. And the article was included in Pharmazie in 2015.COA of Formula: C15H12N2S This article mentions the following:

Fifteen 2-substituted ethenesulfonic acid ester derivatives were designed, synthesized, and evaluated for the inhibitory activities against protein tyrosine phosphatase 1B (PTP1B) and T-Cell protein tyrosine phosphatase (TCPTP). The structural activity relationship (SAR) of these compounds were discussed to clarify the impact of the linker and the optimized tail on the inhibitory activity of PTP1B and selectivity over TCPTP. Most of the compounds exhibited excellent inhibitory activities against PTP1B with IC₅₀ values of 1.5-8.9 μM. SAR anal. revealed that the substituents at the hydrophobic tail significantly alter the inhibitory activity against PTP1B and selectivity over TCPTP, e.g. compound Ethyl-2-(4-(3-(4-(2-chlorophenyl)thiazol-2-ylamino)propoxy)phenyl)ethenesulfonate showed excellent inhibitory activity to PTP1B with IC₅₀ = 7.8 μM, and ∼6-fold selectivity over TCPTP. Combined with our previous findings, that the linker length and the substituted hydrophobic tail had decisive influence on the PTP1B inhibitory activity and selectivity was confirmed. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7COA of Formula: C15H12N2S).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) 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. 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: C15H12N2S

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

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

Benzothiazole-based compounds as potent endothelial lipase inhibitors was written by Meng, Wei;Adam, Leonard P.;Behnia, Kamelia;Zhao, Lei;Yang, Richard;Kopcho, Lisa M.;Locke, Gregory A.;Taylor, David S.;Yin, Xiaohong;Wexler, Ruth R.;Finlay, Heather. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2019.SDS of cas: 80945-86-4 This article mentions the following:

A series of benzothiazoles with a cyano group was synthesized and evaluated as endothelial lipase (EL) inhibitors for the potential treatment of cardiovascular diseases. Efforts to reduce mol. weight and polarity in the series led to improved physicochem. properties of these compounds, as well as selectivity for EL over hepatic lipase (HL). As a benchmark compound, I demonstrated potent EL activity, an acceptable absorption, distribution, metabolism and elimination (ADME) profile and pharmacokinetic (PK) exposure which allowed further evaluation in preclin. animal efficacy studies. In the experiment, the researchers used many compounds, for example, 6-Bromo-2-chlorobenzothiazole (cas: 80945-86-4SDS of cas: 80945-86-4).

6-Bromo-2-chlorobenzothiazole (cas: 80945-86-4) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). 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.SDS of cas: 80945-86-4

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

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