Tag: 200-300

Discovery of N-(4-aryl-5-aryloxy-thiazol-2-yl)-amides as potent RORγt inverse agonists was written by Wang, Yonghui;Yang, Ting;Liu, Qian;Ma, Yingli;Yang, Liuqing;Zhou, Ling;Xiang, Zhijun;Cheng, Ziqiang;Lu, Sijie;Orband-Miller, Lisa A.;Zhang, Wei;Wu, Qianqian;Zhang, Kathleen;Li, Yi;Xiang, Jia-Ning;Elliott, John D.;Leung, Stewart;Ren, Feng;Lin, Xichen. And the article was included in Bioorganic & Medicinal Chemistry in 2015.Formula: C15H12N2S This article mentions the following:

A novel series of N-(4-aryl-5-aryloxy-thiazol-2-yl)-amides as RORγt inverse agonists was discovered. Binding mode anal. of a RORγt partial agonist (2c) revealed by co-crystal structure in RORγt LBD suggests that the inverse agonists do not directly interfere with the interaction between H12 and the RORγt LBD. Detailed SAR exploration led to identification of potent RORγt inverse agonists such as 3m with a pIC₅₀ of 8.0. Selected compounds in the series showed reasonable activity in Th17 cell differentiation assay as well as low intrinsic clearance in mouse liver microsomes. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Formula: C15H12N2S).

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. 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.Formula: C15H12N2S

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

Reengineered tricyclic anti-cancer agents was written by Kastrinsky, David B.;Sangodkar, Jaya;Zaware, Nilesh;McClinch, Kimberly;Farrington, Caroline C.;Giannini, Heather M.;Izadmehr, Sudeh;Dhawan, Neil S.;Narla, Goutham;Ohlmeyer, Michael. And the article was included in Bioorganic & Medicinal Chemistry in 2015.Electric Literature of C6H7ClN2O3S2 This article mentions the following:

The phenothiazine and dibenzazepine tricyclics are potent neurotropic drugs with a documented but underutilized anti-cancer side effect. Reengineering these agents (TFP, CPZ, CIP) by replacing the basic amine with a neutral polar functional group (e.g., RTC-1, RTC-2) abrogated their CNS effects as demonstrated by in vitro pharmacol. assays and in vivo behavioral models. Further optimization generated several phenothiazines and dibenzazepines with improved anti-cancer potency, exemplified by RTC-5. This new lead demonstrated efficacy against a xenograft model of an EGFR driven cancer without the neurotropic effects exhibited by the parent mols. Its effects were attributed to concomitant neg. regulation of PI3K-AKT and RAS-ERK signaling. 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. The thiazole ring is notable as a component of the vitamin thiamine (B1). Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Electric Literature of C6H7ClN2O3S2

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

Quinazolone derivatives was written by Dash, B.;Mahapatra, Prasanta K.;Mahapatra, Prasanna K.. And the article was included in Journal of the Institution of Chemists (India) in 1983.HPLC of Formula: 6318-74-7 This article mentions the following:

Thiazolylquinazolones I [R = Me, Ph; R¹ = thienyl, (un)substituted Ph; R² = H, Ph, 2-Cl₆H₄, 4-ClC₆H₄] were prepared by aminolysis of benzoxazinones II with thiazolylamines III. Arylidenequinazolones I [R = R³C₆H₄CH:CH; R¹ = (un)substituted Ph; R² = H, Ph, 2-ClC₆H₄, 4-ClC₆H₄; R³ = 2-Cl, 4-Cl] were prepared by condensing I (R = Me) with R³C₆H₄CHO. At 500 ppm I inhibited Helminthosporium sativum by 50-70%, in vitro. 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. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities.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

Straightforward synthesis of 2-anilinobenzoxazoles and -benzothiazoles via mechanochemical ball-milling-promoted one-pot reactions was written by Zhang, Ze;Wang, Fang-Jian;Wu, Hao-Hao;Tan, Ya-Jun. And the article was included in Chemistry Letters in 2015.Related Products of 1843-21-6 This article mentions the following:

Under mechanochem. ball-milling and solvent-free conditions, a series of 2-anilinobenzoxazoles and 2-anilinobenzothiazoles were synthesized directly from the one-pot reaction of anilines, CS₂, and 2-aminophenol and -thiophenol. This protocol exhibited the free or cheap use of a cyclodesulfurization reagent, no separation of in-situ generated isothiocyanate, short reaction time and simple work-up procedure. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Related Products of 1843-21-6).

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. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Related Products of 1843-21-6

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

Synthesis of novel 4,5-diphenylthiazole derivatives as potential acyl-CoA : cholesterol O-acyltransferase inhibitors was written by Romeo, G.;Salerno, L.;Milla, P.;Siracusa, M.;Cattel, L.;Russo, Filippo. And the article was included in Pharmazie in 1999.Recommanded Product: 4,5-Diphenylthiazol-2-amine This article mentions the following:

Several N-(4,5-diphenylthiazol-2-yl)-N’-aryl- or -alkyl-(thio)ureas and N-(4,5-diphenylthiazol-2-yl)alkanamides were prepared as potential acyl-CoA : cholesterol O-acyltransferase (ACAT) inhibitors. Synthesis was accomplished by reaction of 2-amino-4,5-diphenylthiazole with suitable isocyanates, isothiocyanates, or acyl chlorides. Some analogs without a 5-Ph substituent or both the Ph groups in 4- and 5-position of the thiazole ring were also prepared Moreover, some bio-isosteres of the title compounds in which the thiazole ring was replaced by an imidazole were synthesized starting from 2-amino-4,5-diphenyl-1H-imidazole. The ability of synthesized compounds to inhibit ACAT was evaluated in vitro by measuring the formation of cholesteryl[¹⁴C]oleate from cholesterol and [1-¹⁴C]oleoyl-CoA in rat liver microsomes. Among the tested compounds, only some thiazole ureas were able to inhibit ACAT in a reasonable degree. N-(4,5-diphenylthiazol-2-yl)-N’-[2,6-bis(2-methylethyl)phenyl]urea and N-(4,5-diphenylthiazol-2-yl)-N’-butylurea were the most active compounds in the series showing IC₅₀ values in the low micromolar range. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Recommanded Product: 4,5-Diphenylthiazol-2-amine).

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

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

Selective inhibition of cytosolic epoxide hydrolase activity in vitro by compounds that inhibit catalase was written by Guenthner, Thomas M.;Hjelle, J. Thomas;Whalen, Robert. And the article was included in Journal of Biochemical Toxicology in 1989.Application In Synthesis of 4,5-Diphenylthiazol-2-amine This article mentions the following:

The ability of inhibitors of catalase to affect cytosolic and microsomal epoxide hydrolase measured as enzymic trans-stilbene oxide hydrolysis and styrene oxide hydrolysis, resp., was investigated. Catalase and cytosolic epoxide hydrolase are inhibited by hydroxylated metabolites of 2-amino-4,5-diphenylthiazole (DPT). The metabolite hydroxylated on the 4-phenyl ring (4OH-DPT) and the metabolite hydroxylted on both Ph rings (4,5-DIOH-DPT) are potent inhibitors of both enzymes; the metabolite hydroxylated on the 5-Ph ring (5OH-DPT) is less potent. Unmetabolized DPT has no effect on either enzyme. 4OH-DPT inhibits, but 5OH-DPT enhances, microsomal epoxide hydrolase. 4,5-DIOH-DPT and DPT have no effect on this enzyme. Other compounds that inhibit both catalase and cytosolic epoxide hydrolase, but do not inhibit microsomal epoxide hydrolase, are nordihydroguaiaretic acid and 2-aminothiazole. Microsomal epoxide hydrolase is enhanced by 2-aminothiazole and levamisole. Thus, these inhibitors of catalase are selective epoxide hydrolase inhibitors in that they inhibit cytosolic epoxide hydrolase activity, but have either no effect on, or increase the activity of, microsomal epoxide hydrolase. Conversely, the selective cytosolic epoxide hydrolase inhibitors 4-phenylchalcone oxide and 4′-phenylchalcone oxide do not inhibit catalase, nor does trichloropropene oxide, a selective microsomal epoxide hydrolase inhibitor. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Application In Synthesis of 4,5-Diphenylthiazol-2-amine).

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

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

Design, synthesis, and AChE inhibitory activity of new benzothiazole-piperazines was written by Demir Ozkay, Umide;Can, Ozgur Devrim;Saglik, Begum Nurpelin;Acar Cevik, Ulviye;Levent, Serkan;Ozkay, Yusuf;Ilgin, Sinem;Atli, Ozlem. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2016.Computed Properties of C9H10N2O2S This article mentions the following:

In the current study, 14 new benzothiazole-piperazine compounds were designed to meet the structural requirements of acetylcholine esterase (AChE) inhibitors. The target compounds were synthesized in three steps. Structures of the newly synthesized compounds (7–20) were confirmed using IR, ¹H NMR, ¹³C NMR, and HRMS methods. The inhibitory potential of the compounds on AChE (E.C.3.1.1.7, from elec. eel) was then investigated. Among the compounds, two compounds, 19 and 20 showed very good activity on AChE enzyme. Kinetics studies were performed to observe the effects of the most active compounds on the substrate-enzyme relationship. Cytotoxicity studies, genotoxicity studies, and theor. calculation of pharmacokinetics properties were also carried out. The compounds 19 and 20 were found to be nontoxic in both of the toxicity assays. A good pharmacokinetics profile was predicted for the synthesized compounds Mol. docking studies were performed for the most active compounds, 19 and 20, and interaction modes with enzyme active sites were determined Docking studies indicated a strong interaction between the active sites of AChE enzyme and the analyzed compounds In the experiment, the researchers used many compounds, for example, 5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6Computed Properties of C9H10N2O2S).

5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6) 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.Computed Properties of C9H10N2O2S

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

Development of a more highly selective M₁ antagonist from the continued optimization of the MLPCN Probe ML012 was written by Melancon, Bruce J.;Lamers, Alexander P.;Bridges, Thomas M.;Sulikowski, Gary A.;Utley, Thomas J.;Sheffler, Douglas J.;Noetzel, Meredith J.;Morrison, Ryan D.;Scott Daniels, J.;Niswender, Colleen M.;Jones, Carrie K.;Jeffrey Conn, P.;Lindsley, Craig W.;Wood, Michael R.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2012.Category: thiazole This article mentions the following:

This Letter describes the continued optimization of an MLPCN probe mol. (ML012) through an iterative parallel synthesis approach. After exploring extensive modifications throughout the parent structure, we arrived at a more highly M₁-selective antagonist, compound (I; VU0415248). Muscarinic subtype selectivity across all five human and rat receptors for I, along with rat selectivity for the lead compound (ML012), is presented. In the experiment, the researchers used many compounds, for example, 2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9Category: thiazole).

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

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

Quantitative structure-activity relationships of antitumor guanidinothiazolecarboxamides with survival enhancement for therapy in the 3LL Lewis lung carcinoma model was written by Schnur, Rodney C.;Gallaschun, Randall J.;Singleton, David H.;Grissom, Martin;Sloan, Donald E.;Goodwin, Peter;McNiff, Patricia A.;Fliri, Anton F. J.;Mangano, F. Michael. And the article was included in Journal of Medicinal Chemistry in 1991.SDS of cas: 6294-52-6 This article mentions the following:

Title compounds, e.g., I (R = H, 4-Cl, 4-Me, 4-OMe, 4-NO₂, 4-F, 4-CHMe₂, 4-SMe, 4-OH, 5-F, 5-SMe, 5-NO₂, 5-OEt, 5-Ph, 5-OH, 5-OBu, 6-Cl, 6-F, 6-OMe, 6-CONH₂, 6-Ph, 6-SO₂NH₂, 6-cyano, 6-Me, 5,6-Cl₂, 5,6-F₂, 5,6-Me₂, 5-F-6-OMe, 5-F-6-Cl) were prepared and tested for antitumor activity against exptl. pulmonary metastases of 3LL Lewis lung carcinoma. They produce enhancement of survival by using 8 days of i.p. dosing initiated 2 days after i.v. tumor challenge. Quant. structure-activity relationships have been discovered in the series with survival enhancement correlated to substituent parameters. The most effective analog in this series was I (R = 5-F). In the experiment, the researchers used many compounds, for example, 5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6SDS of cas: 6294-52-6).

5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6) 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.SDS of cas: 6294-52-6

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

Naphtho[1,2-d]thiazol-2-ylamine (SKA-31), a new activator of KCa2 and KCa3.1 potassium channels, potentiates the endothelium-derived hyperpolarizing factor response and lowers blood pressure was written by Sankaranarayanan, Ananthakrishnan;Raman, Girija;Busch, Christoph;Schultz, Tim;Zimin, Pavel I.;Hoyer, Joachim;Kohler, Ralf;Wulff, Heike. And the article was included in Molecular Pharmacology in 2009.Product Details of 6294-52-6 This article mentions the following:

Small-conductance (KCa2.1-2.3) and intermediate-conductance (KCa3.1) calcium-activated K⁺ channels are critically involved in modulating calcium-signaling cascades and membrane potential in both excitable and nonexcitable cells. Activators of these channels constitute useful pharmacol. tools and potential new drugs for the treatment of ataxia, epilepsy, and hypertension. Here, we used the neuroprotectant riluzole as a template for the design of KCa2/3 channel activators that are potent enough for in vivo studies. Of a library of 41 benzothiazoles, we identified 2 compounds, anthra[2,1-d]thiazol-2-ylamine (SKA-20) and naphtho[1,2-d]thiazol-2-ylamine (SKA-31), which are 10 to 20 times more potent than riluzole and activate KCa2.1 with EC₅₀ values of 430 nM and 2.9 μM, KCa2.2 with an EC₅₀ value of 1.9 μM, KCa2.3 with EC₅₀ values of 1.2 and 2.9 μM, and KCa3.1 with EC₅₀ values of 115 and 260 nM. Likewise, SKA-20 and SKA-31 activated native KCa2.3 and KCa3.1 channels in murine endothelial cells, and the more “drug-like” SKA-31 (half-life of 12 h) potentiated endothelium-derived hyperpolarizing factor-mediated dilations of carotid arteries from KCa3.1(+/+) mice but not from KCa3.1(-/-) mice. Administration of 10 and 30 mg/kg SKA-31 lowered mean arterial blood pressure by 4 and 6 mm Hg in normotensive mice and by 12 mm Hg in angiotensin-II-induced hypertension. These effects were absent in KCa3.1-deficient mice. In conclusion, with SKA-31, we have designed a new pharmacol. tool to define the functional role of the KCa2/3 channel activation in vivo. The blood pressure-lowering effect of SKA-31 suggests KCa3.1 channel activation as a new therapeutic principle for the treatment of hypertension. In the experiment, the researchers used many compounds, for example, 5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6Product Details of 6294-52-6).

5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6) 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. 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 6294-52-6

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