Month: February 2023

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

Lanthanide-catalyzed cyclocarbonylation and cyclothiocarbonylation: a facile synthesis of benzannulated 1,3-diheteroatom five- and six-membered heterocycles was written by Jing, Yu Feng;Liu, Rui Ting;Lin, Yang Hui;Zhou, Xi Geng. And the article was included in Science China: Chemistry in 2014.HPLC of Formula: 1843-21-6 This article mentions the following:

La[N(SiMe₃)₂]₃ proved to be an efficient catalytic system for the cyclocarbonylation of 1,2-disubstituted benzenes with isocyanates. Aryl/alkyl isocyanates were reacted with o-phenylenediamine, o-aminophenol, o-aminothiophenol, catechols and anilines ortho-substituted by CH₂NH₂ and CONH₂ to form the corresponding benzimidazolones, benzoxazolones, benzothiazolones, benzodioxolones, 3,4-dihydroquinazolin-2(1H)-one and quinazolinediones resp. This methodol. was also applicable for the preparation of the corresponding thio analogs starting from aryl/alkyl isothiocyanates or CS₂ in good to excellent yields. Based on the results of experiments performed using an o-aminobenzamido dianion lanthanide complex, a general mechanism involving the tandem reaction of two lanthanide-ligand bonds was proposed. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6HPLC of Formula: 1843-21-6).

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. 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.HPLC of Formula: 1843-21-6

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

Synthesis and antiplatelet activity of 2-amino-4,5-diphenylthiazole derivatives was written by Inoue, Hisataka;Ikesue, Koichi;Taniguchi, Yasuaki. And the article was included in Yakugaku Zasshi in 1995.Product Details of 6318-74-7 This article mentions the following:

A series of 4,5-diphenylthiazoles containing morpholinoalkyl amino groups at the 2 position was synthesized and their anti-platelet activities were evaluated. The inhibitory effects of the compounds in which Ph groups at the 4 position were substituted by methoxy groups were more potent than those of aspirin and ibuprofen on the collagen-induced rabbit platelet aggregation. These compounds were also shown to have potent efficacies on the arachidonic acid-induced platelet aggregation. These compounds did not affect the ADP-induced platelet aggregation similarly to non-steroidal anti-inflammatory agents. Moreover, their efficacies on the inhibition of prostaglandin synthesis were more potent than that of ibuprofen. Therefore, the authors thought that 2-(morpholinoalkyl)amino-4,5-diphenylthiazoles, in spite of their basic properties, inhibited the platelet aggregation based on cyclooxygenase. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Product Details of 6318-74-7).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) 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.Product Details of 6318-74-7

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

Vicinal diaryl azole-based urea derivatives as potential cholesterol lowering agents acting through inhibition of SOAT enzymes was written by Pal, Palash;Gandhi, Hardik P.;Kanhed, Ashish M.;Patel, Nirali R.;Mankadia, Niraj N.;Baldha, Satish N.;Barmade, Mahesh A.;Murumkar, Prashant R.;Yadav, Mange Ram. And the article was included in European Journal of Medicinal Chemistry in 2017.HPLC of Formula: 6318-74-7 This article mentions the following:

A novel series of vicinal diaryl azole-urea derivatives were synthesized and evaluated for their potential to inhibit SOAT enzyme. Among the reported compounds, 1-butyl-3-(4-(2-methyl-4-(p-tolyl)thiazol-5-yl)phenyl)urea emerged as the most potent compound with an IC₅₀ value of 2.43 μM. In polaxamer-407 induced lipoprotein lipase inhibition model, 1-butyl-3-(4-(2-methyl-4-(p-tolyl)thiazol-5-yl)phenyl)urea reduced triglyceride turnover in vivo. 1-Butyl-3-(4-(2-methyl-4-(p-tolyl)thiazol-5-yl)phenyl)urea also showed dose-dependent prevention of serum total cholesterol and prevention of LDL-C elevation at a dose of 30 mg/kg. Furthermore, 1-butyl-3-(4-(2-methyl-4-(p-tolyl)thiazol-5-yl)phenyl)urea showed potential to stop falling levels of serum HDL-C dose-dependently and improved the atherogenic index. Effect of 1-butyl-3-(4-(2-methyl-4-(p-tolyl)thiazol-5-yl)phenyl)urea on body weight, plaque formation and development of atherogenic lesions were studied. Toxicol. study of 1-butyl-3-(4-(2-methyl-4-(p-tolyl)thiazol-5-yl)phenyl)urea indicated that at a dose of 2000 mg/kg, 1-butyl-3-(4-(2-methyl-4-(p-tolyl)thiazol-5-yl)phenyl)urea was devoid of any signs of toxicity or mortality. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7HPLC of Formula: 6318-74-7).

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.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.HPLC of Formula: 6318-74-7

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

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

Glycogen Synthase Kinase-3 (GSK-3) Inhibitory Activity and Structure-Activity Relationship (SAR) Studies of the Manzamine Alkaloids. Potential for Alzheimer’s Disease was written by Hamann, Mark;Alonso, Diana;Martin-Aparicio, Ester;Fuertes, Ana;Perez-Puerto, M. Jose;Castro, Ana;Morales, Susana;Navarro, Maria Luisa;del Monte-Millan, Maria;Medina, Miguel;Pennaka, Hari;Balaiah, Akula;Peng, Jiangnan;Cook, Jennifer;Wahyuono, Subagus;Martinez, Ana. And the article was included in Journal of Natural Products in 2007.Recommanded Product: 2-Acetamido-4-methylthiazole-5-sulfonyl chloride This article mentions the following:

Manzamine A and related derivatives isolated from a common Indonesian sponge, Acanthostrongylophora, have been identified as a new class of GSK-3β inhibitors. The semisynthesis of new analogs and the first structure-activity relationship studies with GSK-3β are also reported. Moreover, manzamine A proved to be effective in decreasing tau hyperphosphorylation in human neuroblastoma cell lines, a demonstration of its ability to enter cells and interfere with tau pathol. Inhibition studies of manzamine A against a selected panel of five different kinases related to GSK-3β, specifically CDK-1, PKA, CDK-5, MAPK, and GSK-3α, show the specific inhibition of manzamine A on GSK-3β and CDK-5, the two kinases involved in tau pathol. hyperphosphorylation. These results suggest that manzamine A constitutes a promising scaffold from which more potent and selective GSK-3 inhibitors could be designed as potential therapeutic agents for Alzheimer’s disease. In the experiment, the researchers used many compounds, for example, 2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9Recommanded Product: 2-Acetamido-4-methylthiazole-5-sulfonyl chloride).

2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9) 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.Recommanded Product: 2-Acetamido-4-methylthiazole-5-sulfonyl chloride

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

Syntheses of 2-aminothiazole derivatives. I was written by Tajika, Yoshio;Nitta, Yoshihiro;Yomoda, Jitsuho;Oya, Hiroshi. And the article was included in Yakugaku Zasshi in 1951.Application of 6318-74-7 This article mentions the following:

R¹COCH₂R², X, and H₂NCSNH₂ (R¹, R² = alkyl or aryl group, and X = halogen) are heated to obtain S.C(NH₂):N.CR¹:CR² (I). For the following I, R¹, R², and m.p., resp., are as follows: p-MeOC₆H₄, Me, 114-17°; Me, p-MeOC₆H₄, 187-8°; Ph, H, 147.5-8.5°; p-MeOC₆H₄, H, 205-6°; Ph, BzNH, 190-1°; Ph, Ph, 186-7°. The antibacterial action of these compounds toward Staphylococcus aureus is given. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Application of 6318-74-7).

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. 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.Application of 6318-74-7

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

Discovery and Optimization of a Series of Sulfonamide Inverse Agonists for the Retinoic Acid Receptor-Related Orphan Receptor-a was written by Doebelin, Christelle;He, Yuanjun;Campbell, Sean;Nuhant, Philippe;Kumar, Naresh;Koenig, Marcel;Garcia-Ordonez, Ruben;Chang, Mi Ra;Roush, William R.;Lin, Li;Kahn, Susan;Cameron, Michael D.;Griffin, Patrick R.;Solt, Laura A.;Kamenecka, Theodore M.. And the article was included in Medicinal Chemistry (Sharjah, United Arab Emirates) in 2019.Electric Literature of C6H7ClN2O3S2 This article mentions the following:

Background: Despite a massive industry endeavor to develop RORalpha-modulators for autoimmune disorders, there has been no indication of efforts to target the close family member RORa for similar indications. This may be due to the misconception that RORa is redundant to RORalpha, or the inherent difficulty in cultivating tractable starting points for RORa. RORa-selective modulators would be useful tools to interrogate the biol. of this understudied orphan nuclear receptor. Objective: The goal of this research effort was to identify and optimize synthetic ligands for RORa starting from the known LXR agonist T0901317. Methods: Fourty-five analogs of the sulfonamide lead (1) were synthesized and evaluated for their ability to suppress the transcriptional activity of RORa, RORalpha, and LXRa in cell-based assays. Analogs were characterized by 1H-NMR, 13C-NMR, and LC-MS anal. The pharmacokinetic profile of the most selective RORa inverse agonist was evaluated in rats with i.p. (i.p.) and per oral (p.o.)dosing. Results: Structure-activity relationship studies led to potent dual RORa/RORalpha inverse agonists as well as RORa-selective inverse agonists (20, 28). LXR activity could be reduced by removing the sulfonamide nitrogen substituent. Attempts to improve the potency of these selective leads by varying substitution patterns throughout the mol. proved challenging. In the experiment, the researchers used many compounds, for example, 2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9Electric Literature of C6H7ClN2O3S2).

2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9) 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.Electric Literature of C6H7ClN2O3S2

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

Fluorescence Properties of 5-(5,6-Dimethoxybenzothiazol-2-yl)-2′-deoxyuridine (d^btU) and Oligodeoxyribonucleotides Containing d^btU was written by Hirose, Wataru;Sato, Kousuke;Matsuda, Akira. And the article was included in European Journal of Organic Chemistry in 2011.COA of Formula: C9H10N2O2S This article mentions the following:

We describe the synthesis and photo-phys. properties of 11 substituted 5-(benzothiazol-2-yl)-2′-deoxyuridine derivatives and oligodeoxyribonucleotides (ODNs) containing 5-(5,6-dimethoxybenzothiazol-2-yl)-2′-deoxyuridine (d^btU), which was the strongest fluorescent derivative among those prepared The fluorescence properties of d^btU itself and ODNs containing d^btU show the same tendency of being weaker in both neutral and acidic solution and stronger in basic solution The ODNs (15mer) containing 16 combinations of 5′-X^btU-3′ and 5′-^btUY-3′, where X, Y = A, T, G, or C, were synthesized, and their fluorescence intensity and quantum yield in basic solution were compared. On average, only the ODN with the 5′-G^btU-3′ sequence shows a 7.9-fold lower fluorescence intensity than the other sequences. Ab initio calculations of 5′-G^btU-3′ and 5′-^btUG-3′ as models under basic conditions suggest that the lower fluorescence of the ODN containing the 5′-G^btU-3′ sequence is caused by a wider overlap between stacked guanine (Gua) and ^btUra than that of the 5′-^btUG-3′ sequence and that the HOMO is delocalized not only on ^btUra but also on Gua. In the experiment, the researchers used many compounds, for example, 5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6COA of Formula: C9H10N2O2S).

5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6) 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. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.COA of Formula: C9H10N2O2S

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

The near-ultraviolet absorption spectra of some heterocyclic compounds. II. Benzothiazoles was written by Cerniani, A.;Passerini, R.. And the article was included in Journal of the Chemical Society in 1954.Recommanded Product: N-Phenylbenzo[d]thiazol-2-amine This article mentions the following:

The UV spectra of benzothiazole and a series of derivatives similar to benzoxazole derivatives obtained previously (loc. cit.) have been measured. The absorption maximum of 35 compounds are given and discussed briefly. The benzothiazoles show bathochromic shifts of bands without intensification. The following compounds were prepared by refluxing ethanolic solutions of 2-chloro- or 6-nitro-2-chlorobenzothiazole and the appropriate K mercaptide or aniline derivative: 2-(ο-tolylthio)benzothiazole, b₁₇ 237°; 2-(m-tolylthio)benzothiazole, b₁₇ 245°; 2-(ο-toluidino)benzothiazole, m. 127°; 2-(m-toluidino)benzothiazole, m. 124°; 3-(m-nitroanilino)benzothiazole, m. 190°; 6-nitro-2-(phenylthio)benzothiazole, m. 104°; 6-nitro-2-(ο-tolylthio)benzothiazole, m. 102°; 6-nitro-2-(m-tolylthio)benzothiazole, m. 134°; 6-nitro-2-(p-tolylthio)benzothiazole, m. 146°; 6-nitro-2-(m-toluidino)benzothiazole, m. 222°. Heating 2-chloro-6-nitrobenzothiazole and m-nitroaniline yielded 6-nitro-2-(m-nitrophenyl)bensothiazole, yellow needles from AcOH, m. 257°. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Recommanded Product: N-Phenylbenzo[d]thiazol-2-amine).

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.Recommanded Product: N-Phenylbenzo[d]thiazol-2-amine

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