Category: thiazole

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

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

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

Development of an efficient ruthenium catalyzed synthetic process and mechanism for the facile conversion of benzothiazoles to orthanilic acids was written by Jagadeesh, R. V.;Karthikeyan, P.;Nithya, P.;Sandhya, Y. Sree;Reddy, S. Sudhaker;Reddy, P. Pradeep Kumar;Kumar, M. Vinod;Charan, K. T. Prabhu;Narender, R.;Bhagat, P. R.. And the article was included in Journal of Molecular Catalysis A: Chemical in 2010.HPLC of Formula: 68867-17-4 This article mentions the following:

Ruthenium-Schiff base complex catalyzed efficient protocol has been developed for the synthesis of orthanilic acids from benzothiazoles in good to excellent yields using N-haloamines. Hexa-coordinated ruthenium complex with Schiff base and triphenylphosphine ligands has been prepared and its catalytic function was invented for the synthesis of orthanilic acids. The synthetic process utilizes our efficient method for the selective and preferential oxidation of thiazole ring of benzothiazoles using N-haloamines without effecting Ph ring. The detailed catalytic, mechanistic and kinetic investigations have been made for the synthetic reactions. Solvent isotope studies have been made in H₂O-D₂O and the reactions were carried out at different temperatures Under the identical set of conditions, the kinetics of catalyzed reactions has been compared with uncatalyzed reactions and found that the catalyzed reactions are 9-11 folds faster. The catalytic constants (K_C) have been calculated for each N-haloamine at different temperatures and the values of activation parameters with respect to the catalyst have been evaluated. Spectroscopic evidence for the formation of 1:1 complex between N-haloamine and ruthenium has been obtained. The observed results have been explained by a plausible mechanism and the related rate law has been deduced. In the experiment, the researchers used many compounds, for example, Benzothiazole-5-carboxylic acid (cas: 68867-17-4HPLC of Formula: 68867-17-4).

Benzothiazole-5-carboxylic acid (cas: 68867-17-4) 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. 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.HPLC of Formula: 68867-17-4

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

MOARF, an Integrated Workflow for Multiobjective Optimization: Implementation, Synthesis, and Biological Evaluation was written by Firth, Nicholas C.;Atrash, Butrus;Brown, Nathan;Blagg, Julian. And the article was included in Journal of Chemical Information and Modeling in 2015.Product Details of 55661-33-1 This article mentions the following:

We describe the development and application of an integrated, multiobjective optimization workflow (MOARF) for directed medicinal chem. design. This workflow couples a rule-based mol. fragmentation scheme (SynDiR) with a pharmacophore fingerprint-based fragment replacement algorithm (RATS) to broaden the scope of reconnection options considered in the generation of potential solution structures. Solutions are ranked by a multiobjective scoring algorithm comprising ligand-based (shape similarity) biochem. activity predictions as well as physicochem. property calculations Application of this iterative workflow to optimization of the CDK2 inhibitor Seliciclib (CYC202, R-roscovitine) generated solution mols. in desired physicochem. property space. Synthesis and exptl. evaluation of optimal solution mols. demonstrates CDK2 biochem. activity and improved human metabolic stability. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Product Details of 55661-33-1).

Thiazol-2-ylmethanamine (cas: 55661-33-1) 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. 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.Product Details of 55661-33-1

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

Photo-oxidative Cross-Dehydrogenative Coupling-Type Reaction of Thiophenes with α-Position of Carbonyls Using a Catalytic Amount of Molecular Iodine was written by Sudo, Yusuke;Yamaguchi, Eiji;Itoh, Akichika. And the article was included in Organic Letters in 2017.Application In Synthesis of 5-Phenylthiazole This article mentions the following:

Substituted thiophenes and thiazoles such as I (R = Me, Ph, 4-MeC₆H₄, 4-MeOC₆H₄, 4-O₂NC₆H₄, 4-OHCC₆H₄, 4-MeO₂CC₆H₄, PhCOOCH₂) underwent regioselective and chemoselective photochem. aerobic dehydrogenative coupling with 1,1,1-tricarbonyl compounds such as (EtO₂C)₂CHR¹ (R¹ = EtO₂C, Me₂NCO, PhSO₂) in the presence of I₂ and K₃PO₄ in MeCN/H₂O (and in the absence of added metals) under irradiation by compact fluorescent lamps to give substituted thienyl and thiazolyl tricarbonyl compounds such as II (R = Me, Ph, 4-MeC₆H₄, 4-MeOC₆H₄, 4-O₂NC₆H₄, 4-OHCC₆H₄, 4-MeO₂CC₆H₄, PhCOOCH₂; R¹ = EtO₂C, Me₂NCO, PhSO₂). The coupling reaction did not occur in the absence of light or in the presence of radical inhibitors, and II (R = Me; R¹ = EtO₂C) was formed from coupling of 2-methylthiophene and IC(CO₂Et)₃ in the absence of iodine; a mechanism for the coupling reaction is proposed. 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. 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 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.Application In Synthesis of 5-Phenylthiazole

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

2-Aminobenzothiazole and its 2- and 3-derivatives in a reaction with acrylic acid was written by Rozhkova, N. K.;Saprykina, V. A.. And the article was included in Uzbekskii Khimicheskii Zhurnal in 1974.COA of Formula: C13H10N2S This article mentions the following:

Benzothiazolepropionic acids (I; R = H, Me, Ph) were obtained in 38-93% yields by addition of CH2:CHCO2H to 2-aminobenzothiazoles. N-Benzothiazolylidene-p-alanine derivatives (II; R = CH2CH2CO2H, Me, Ph) were obtained in 31-97% yields by addition of CH2:CHCO2H to 2-iminobenzothiazoles. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6COA of Formula: C13H10N2S).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) 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.COA of Formula: C13H10N2S

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

Design, synthesis and analgesic/anti-inflammatory evaluation of novel diarylthiazole and diarylimidazole derivatives towards selective COX-1 inhibitors with better gastric profile was written by Abdelazeem, Ahmed H.;El-Saadi, Mohammed T.;Safi El-Din, Asmaa G.;Omar, Hany A.;El-Moghazy, Samir M.. And the article was included in Bioorganic & Medicinal Chemistry in 2017.Application In Synthesis of 4,5-Diphenylthiazol-2-amine This article mentions the following:

The inhibition of gastric cyclooxygenase 1 (COX-1) enzyme was believed to be the major cause of non-steroidal anti-inflammatory drugs (NSAIDs)-induced gastric ulcer. Recent studies disproved this belief and showed that the gastric tissues vulnerability is not solely connected to COX-1 inhibition. This work aimed at exploring and rationalizing the differential analgesic and anti-inflammatory activities of novel selective COX-1 inhibitors with improved gastric profile. Two novel series of 4,5-diarylthiazole and diarylimidazole were designed, synthesized in analogy to selective COX-1 inhibitors (mofezolac and FR122047) which lack gastric damaging effects. The new compounds were evaluated in vitro for their COXs inhibitory activity and in vivo for their anti-inflammatory and analgesic potentials. Four compounds; diphenylthiazole glycine derivatives (15a, 15b) and diphenylimidazolo acetic acid derivatives (19a, 19b), which possess carboxylic acid group exhibited significant activity and selectivity against COX-1 over COX-2. Of these compounds, (4,5-bis(4-methoxyphenyl)thiazol-2-yl)glycine 15b was the most potent compound against COX-1 with an inhibitory half maximal concentration (IC₅₀) of 0.32 μM and a selectivity index (COX-2 IC₅₀/COX-1 IC₅₀) of 28.84. Furthermore, an ulcerogenicity study was performed where the tested compounds demonstrated a significant gastric tolerance. Interestingly, the most selective COX-1 inhibitor showed higher analgesic activity in vivo as expected compared to their moderate anti-inflammatory activity. This study underscores the need for further design and development of novel analgesic agents with low tendency to cause gastric damage based on improving their COX-1 affinity and selectivity profile. 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. 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. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Application In Synthesis of 4,5-Diphenylthiazol-2-amine

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

Preparation and spectroscopy of new bi-, tri-, and tetracyclic thiazole derivatives was written by Sanchez-Viesca, F.. And the article was included in Revista Latinoamericana de Quimica in 1990.Synthetic Route of C15H12N2S This article mentions the following:

Thiazoles I [R – NH₂, Me; R¹ = 2,4,5-(MeO)₃C₆H₂, Ph; R² = H, Me, Ph] were obtained from RCSNH₂ and ClCHR²COR¹. Thiazolothiazole II and bithiazole III were prepared from 2,4,5-(MeO)₃C₆H₂CHO or 2,4,5-(MeO)₃C₆H₂COCH₂Cl and dithiooxamide. 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. 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.Synthetic Route of C15H12N2S

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