Month: January 2023

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

Interaction of sulfur monochloride with thiocarbamide and thiocarbanilide was written by Sahasrabudhey, R. H.. And the article was included in Journal of the Indian Chemical Society in 1950.Safety of N-Phenylbenzo[d]thiazol-2-amine This article mentions the following:

S₂Cl₂ (I) with thiourea in CHCl₃ or absolute EtOH gave a yellow solid from which water extracted α,α’-dithiodiformamidine (II); nitrate, m. 138° (decomposition); picrate, m. 154° (decomposition). Alk. hydrolysis of II formed S, thiourea, and NH₂CN. I (2 cc.) in 10 cc. of C₆H₆ or CHCl₃ refluxed 20 min. with 4 g. of CS(NHPh)₂ in 50 cc. of solvent, after evaporation of the solvent and extraction with EtOH, gave 3.6 g. 2-anilinobenzothiazole, m. 159°; Ac derivative, m. 162-3°. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Safety of N-Phenylbenzo[d]thiazol-2-amine).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) 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.Safety of N-Phenylbenzo[d]thiazol-2-amine

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

Copper(II)-Mediated Dehydrogenative Cross-Coupling of Heteroarenes was written by Mao, Zhifeng;Wang, Zhe;Xu, Zhaoqing;Huang, Fei;Yu, Zhengkun;Wang, Rui. And the article was included in Organic Letters in 2012.Related Products of 1826-13-7 This article mentions the following:

Cu(OAc)₂-mediated dehydrogenative cross-coupling between two heteroarenes has been realized in the absence of any other additive. A mechanism involving a formal Cu(II) to Cu(0) route by convergent disproportionation of the copper mediator is proposed and has been evidenced by copper mirror formation during the reaction. This synthetic protocol provides a concise and “green” access to unsym. biheteroarenes bearing structural motifs of substantial utility in organic synthesis. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Related Products of 1826-13-7).

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. 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 1826-13-7

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

Design and Synthesis of New Pyrazole-Based Heterotricycles and their Derivatization by Automated Library Synthesis was written by Fricero, Prisca;Bialy, Laurent;Czechtizky, Werngard;Mendez, Maria;Harrity, Joseph P. A.. And the article was included in ChemMedChem in 2020.COA of Formula: C4H6N2S This article mentions the following:

This work highlighted how a readily assembled N-hydroxyethyl pyrazole trifluoroborate offered rapid access to architecturally distinct 5-6-6- and 5-7-6-fused tricyclic compounds such as I [R = F, NO₂, CO₂H, etc.] and II [R¹ = NEt₂, N-morpholino, NHCH₂-2-pyridyl, etc.]. This chem. was not only amenable to single compound synthesis, but also to high-throughput experimentation. It give easy access to diverse compound arrays with various physicochem. and ADME profiles by fully automated library synthesis. The combination of the high-throughput experimentation with rapid testing of the compounds in an integrated physicochem. and ADME profiling workflow allowed accelerated design of novel lead compounds in drug-discovery projects. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1COA of Formula: C4H6N2S).

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. 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.COA of Formula: C4H6N2S

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

Infrared and the near-ultraviolet absorption spectra of guanidine and benzothiazole derivatives was written by Suresh, K. S.;Ramachandran, J.;Rao, C. N. R.. And the article was included in Journal of Scientific & Industrial Research in 1961.Computed Properties of C13H10N2S This article mentions the following:

Infrared and ultraviolet absorption spectra of guanidine and benzothiazole derivatives showed characteristic bands. Mono-, di-, and triphenyl guanidines had bands at 1692, 1647, and 1659 cm.^-1, possibly due to variations of band order with conjugation, while in the ultraviolet region they showed progressively increasing bathochromic shifts. The ultraviolet spectrum of 2-mercaptobenzothiazole (I) in acid and basic media showed a variation in the absorption maximum, possibly due to the 2,3-dihydrobenzathiazole-2-thione structure assumed by I. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Computed Properties of C13H10N2S).

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. 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 C13H10N2S

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

4,6-Substituted-1H-indazoles as potent IDO1/TDO dual inhibitors was written by Yang, Lingling;Chen, Yang;He, Junlin;Njoya, Emmanuel Mfotie;Chen, Jianjun;Liu, Siyan;Xie, Congqiang;Huang, Wenze;Wang, Fei;Wang, Zhouyu;Li, Yuzhi;Qian, Shan. And the article was included in Bioorganic & Medicinal Chemistry in 2019.Electric Literature of C10H14N2O4S This article mentions the following:

Indoleamine 2,3-dioxygenase 1 (IDO1) and tryptophan 2,3-dioxygenase (TDO) are constitutively overexpressed in many types of cancer cells and exert important immunosuppressive functions. In this article, a series of 4,6-substituted-1H-indazole derivatives were synthesized and evaluated the inhibitory activities against IDO1 and TDO, as well as their structure-activity relationships (SARs). Among these, compound 35(I) displayed the most IDO1 inhibitory potency with an IC₅₀ value of 0.74 μM in an enzymic assay and 1.37 μM in HeLa cells. Quant. anal. of the Western blot results indicated that I significantly decreased the INFγ-induced IDO1 expression in a concentration-dependent manner. In addition, I showed promising TDO inhibition with an IC₅₀ value of 2.93 μM in the enzymic assay and 7.54 μM in A172 cells. Moreover, I exhibited in vivo antitumor activity in the CT26 xenograft model. These findings suggest that I is a potent IDO1/TDO dual inhibitor, and has the potential to be developed for IDO1/TDO-related cancer treatment. In the experiment, the researchers used many compounds, for example, Methyl 2-Boc-aminothiazole-4-carboxylate (cas: 850429-62-8Electric Literature of C10H14N2O4S).

Methyl 2-Boc-aminothiazole-4-carboxylate (cas: 850429-62-8) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). 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 C10H14N2O4S

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