Heterocyclic Building Blocks-Thiazole

Copper-Catalyzed Oxidative Arylation of Heteroarenes under Mild Conditions Using Dioxygen as the Sole Oxidant was written by Yang, Fanzhi;Xu, Zhaoqing;Wang, Zhe;Yu, Zhengkun;Wang, Rui. And the article was included in Chemistry – A European Journal in 2011.Category: thiazole This article mentions the following:

A novel copper-catalyzed oxidative heteroarene arylation reaction is reported. Heteroarene compounds such as benzoxazole and benzothiazole are easily cross-coupled with arylboronic esters under an O₂ atmosphere. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Category: thiazole).

5-Phenylthiazole (cas: 1826-13-7) 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.Category: thiazole

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

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

Orally bioavailable small molecule ketoamide-based inhibitors of cathepsin K was written by Barrett, David G.;Catalano, John G.;Deaton, David N.;Long, Stacey T.;Miller, Larry R.;Tavares, Francis X.;Wells-Knecht, Kevin J.;Wright, Lois L.;Zhou, Hui-Qiang Q.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2004.Electric Literature of C4H6N2S This article mentions the following:

An orally available series of ketoamide-based inhibitors of cathepsin K has been identified. Starting from a potent inhibitor with poor oral bioavailability, modifications to P¹ and P¹‘ elements led to enhancements in solubility and permeability. These improvements resulted in orally available cathepsin K inhibitors. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Electric Literature of C4H6N2S).

Thiazol-2-ylmethanamine (cas: 55661-33-1) 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 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.Electric Literature of C4H6N2S

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

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

Photochemical rearrangements in heterocyclic series. III. Arythiazoles and arylisothiazoles isomers. Experimental results and theoretical study was written by Vernin, G.;Riou, C.;Dou, H. J. M.;Bouscasse, L.;Metzger, J.;Loridan, G.. And the article was included in Bulletin de la Societe Chimique de France in 1973.COA of Formula: C9H7NS This article mentions the following:

In the presence of I2 the photoisomerization of 3 phenylthiazoles and 3 phenylisothiazoles was selective. Five possible mechanisms from published data were examined; those best fitting the results were a valence isomerization mechanism with or without preliminary opening of weaker bonds in the 1st excited state and a mechanism involving torsion of bonds adjacent to S. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7COA of Formula: 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. 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.COA of Formula: C9H7NS

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

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

Palladium-Catalyzed Tandem Ester Dance/Decarbonylative Coupling Reactions was written by Kubo, Masayuki;Inayama, Naomi;Ota, Eisuke;Yamaguchi, Junichiro. And the article was included in Organic Letters in 2022.Computed Properties of C9H7NS This article mentions the following:

“Dance reaction” on the aromatic ring is a powerful method in organic chem. to translocate functional groups on arene scaffolds. Notably, dance reactions of halides and pseudohalides offer a unique platform for the divergent synthesis of substituted (hetero)aromatic compounds when combined with transition-metal-catalyzed coupling reactions. Herein, a tandem reaction of ester dance and decarbonylative coupling enabled by palladium catalysis is reported. In this reaction, 1,2-translocation of the ester moiety on the aromatic ring is followed by decarbonylative coupling with nucleophiles to enable the installation of a variety of nucleophiles at the position adjacent to the ester in the starting material. 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. 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.Computed Properties of C9H7NS

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