Category: thiazole

Applications of Snyder’s theory on linear adsorption chromatography to heterocyclic compounds. I. Influence of the polar and steric effects of various substituents on the adsorption energy of thiazoles on alumina was written by Vernin, Gaston;Vernin, G. Mrs.. And the article was included in Journal of Chromatography in 1970.HPLC of Formula: 1826-13-7 This article mentions the following:

The Snyder theory of linear adsorption chromatog., that was applied to on e hundred thiazole derivatives, made it possible to determine exptl. the adsorption energies of the compounds and to compare these with the adsorption energies calculated by means of fixed tables. In a study on thiazoles containing one or two alkyl groups, this comparison made it possible to determine the variations in adsorption energy of the N atom of the ring due to the polarization effects and to the steric effects induced by the alkyl groups and to relate these effects to the constant relations which exist between the polarization and steric effects of the substituents. A similar investigation was made on 4-aryl thiazoles with various substituents in the 2-position. In this case variations in the adsorption energy of the mols. due to the polarization effects of the groups substituted para to the phenyl group with respect to the substituents in the 2-position were studied, and the mutual electronic interactions between the various groups were determined In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7HPLC of Formula: 1826-13-7).

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. 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.HPLC of Formula: 1826-13-7

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

Discovery of potent, selective small molecule inhibitors of α-subtype of type III phosphatidylinositol-4-kinase (PI4KIIIα) was written by Raubo, Piotr;Andrews, David M.;McKelvie, Jennifer C.;Robb, Graeme R.;Smith, James M.;Swarbrick, Martin E.;Waring, Michael J.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2015.COA of Formula: C7H3BrClNS This article mentions the following:

The discovery and optimization of novel, potent and selective small mol. inhibitors of the α-isoform of type III phosphatidylinositol-4-kinase (PI4Kα) are described. Lead compounds show cellular activity consistent with their PI4Kα potency inhibiting the accumulation of IP1 after PDGF stimulation and reducing cellular PIP, PIP2 and PIP3 levels. Hence, these compounds are useful in vitro tools to delineate the complex biol. pathways involved in signaling through PI4Kα. In the experiment, the researchers used many compounds, for example, 6-Bromo-2-chlorobenzothiazole (cas: 80945-86-4COA of Formula: C7H3BrClNS).

6-Bromo-2-chlorobenzothiazole (cas: 80945-86-4) 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.COA of Formula: C7H3BrClNS

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

Imine-amine isomerization in a series of benzothiazoles was written by Saprykina, V. A.;Ambartsumova, R. F.. And the article was included in Doklady Akademii Nauk UzSSR in 1987.Category: thiazole This article mentions the following:

Thermolysis of iminobenzothiazole (I; R = Me) at 110° gave predominantly isomerized aminobenzothiazole (II; 45%) and bis(benzothiazolylamino) derivative (III; 47%). Thermolysis of I (R = H) afforded tetrahydropyrimidinobenzothiazole IV in 41% yield. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Category: thiazole).

N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6) 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. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Category: thiazole

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

Vinblastine 20′ Amides: Synthetic Analogues That Maintain or Improve Potency and Simultaneously Overcome Pgp-Derived Efflux and Resistance was written by Lukesh, John C.;Carney, Daniel W.;Dong, Huijun;Cross, R. Matthew;Shukla, Vyom;Duncan, Katharine K.;Yang, Shouliang;Brody, Daniel M.;Brutsch, Manuela M.;Radakovic, Aleksandar;Boger, Dale L.. And the article was included in Journal of Medicinal Chemistry in 2017.Safety of Benzothiazole-5-carboxylic acid This article mentions the following:

A series of 180 vinblastine 20′ amides were prepared in three steps from com. available starting materials, systematically exploring a typically inaccessible site in the mol. enlisting a powerful functionalization strategy. Clear structure-activity relationships and a structural model were developed in the studies which provided many such 20′ amides that exhibit substantial and some even remarkable enhancements in potency, many that exhibit further improvements in activity against a Pgp overexpressing resistant cancer cell line, and an important subset of the vinblastine analogs that display little or no differential in activity against a matched pair of vinblastine sensitive and resistant (Pgp overexpressing) cell lines. The improvements in potency directly correlated with target tubulin binding affinity, and the reduction in differential functional activity against the sensitive and Pgp overexpressing resistant cell lines was found to correlate directly with an impact on Pgp-derived efflux. In the experiment, the researchers used many compounds, for example, Benzothiazole-5-carboxylic acid (cas: 68867-17-4Safety of Benzothiazole-5-carboxylic acid).

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

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

Facile, efficient synthesis of polysubstituted thiazoles via α-nitroepoxides and thioureas was written by Zhao, Donghong;Guo, Shanshan;Guo, Xiao;Zhang, Guolin;Yu, Yongping. And the article was included in Tetrahedron in 2016.Name: 4,5-Diphenylthiazol-2-amine This article mentions the following:

An efficient synthesis of 2,4,5-trisubstituted thiazoles via the reaction of α-nitroepoxides and thioureas under mild conditions was developed. This reaction proceeded well at room temperature, to afford products in excellent yields for a wide range of substrate and a possible mechanism was proposed. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Name: 4,5-Diphenylthiazol-2-amine).

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

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

Synthesis of some 4H-pyrimido[2,1-b]benzothiazol-4-ones was written by Alaimo, Robert J.. And the article was included in Journal of Heterocyclic Chemistry in 1973.Product Details of 6294-52-6 This article mentions the following:

A series of 8-substituted and 7,8-disubstituted-4-oxo-3-(4H-pyrimido[2,1-b]benzothiazole)carboxylic acids (I) and esters including a 9-aza analog were synthesized from substituted 2-aminobenzothiazoles and di-Et ethoxymethylenemalonate. No significant antiparasitic activity was detected. 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. 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. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Product Details of 6294-52-6

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

Phenanthroline-functionalized porous aromatic framework: An efficient heterogeneous catalyst for the tandem reaction of 2-iodoanilines and isothiocyanates in water was written by Yue, Jie-Yu;Wang, Ling;Zhang, Li;Ma, Yu;Yang, Peng;Tang, Bo. And the article was included in Microporous and Mesoporous Materials in 2020.Reference of 1843-21-6 This article mentions the following:

A phenanthroline-functionalized porous aromatic framework (Phen-PAF) was synthesized by the Sonogashira reaction between 1,3,5-tris-(4-ethynylphenyl)benzene (TEB) and 3,8-dibromo-1,10-phenanthroline (DPHEN). Phen-PAF was demonstrated to have highly catalytic effect on the tandem reaction between 2-iodoanilines 4-R¹-2-I-C₆H₃NH₂ (R¹ = H, Me, Cl) and isothiocyanates R²C₆H₄N=C=S (R² = 2-Me, 4-Cl, 4-CN, 4-Me), leading to a series of 2-aminobenzothiazole derivatives I in good to excellent yield (80-99%). The reaction was environmentally friendly for utilizing water as solvent under mild heating conditions. More importantly, Phen-PAF catalyst can be recycled by simple filtration and drying. Phen-PAF kept its robust chem. structure and catalytic activity for at least 5 catalytic cycles, which was in accordance with sustainable chem. Phen-PAF reported so far as the first organic porous heterogeneous catalyst towards the tandem reaction of 2-iodoanilines and isothiocyanates with environmentally friendly solvent may enlighten to design more function-oriented PAF materials as heterogeneous catalysts towards various organic reactions. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Reference of 1843-21-6).

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. 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.Reference of 1843-21-6

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

Synthesis and in vitro evaluation of 5-substituted benzovesamicol analogs containing N-substituted amides as potential positron emission tomography tracers for the vesicular acetylcholine transporter was written by Roslin, Sara;De Rosa, Maria;Deuther-Conrad, Winnie;Eriksson, Jonas;Odell, Luke R.;Antoni, Gunnar;Brust, Peter;Larhed, Mats. And the article was included in Bioorganic & Medicinal Chemistry in 2017.Recommanded Product: 55661-33-1 This article mentions the following:

Herein, new ligands for the vesicular acetylcholine transporter (VAChT), based on a benzovesamicol scaffold, are presented. VAChT is acknowledged as a marker for cholinergic neurons and a positron emission tomog. tracer for VAChT could serve as a tool for quant. anal. of cholinergic neuronal d. With an easily accessible triflate precursor, aminocarbonylations were utilized to evaluate the chem. space around the C5 position on the tetrahydronaphthol ring. Synthesized ligands were evaluated for their affinity and selectivity for VAChT. Small, preferably aromatic, N-substituents proved to be more potent than larger substituents. Of the fifteen compounds synthesized, benzyl derivatives (±)-7i and (±)-7l had the highest affinities for VAChT. Compound (±)-7i was chosen to investigate the importance of stereochem. for binding to VAChT and selectivity toward the σ₁ and σ₂ receptors. Enantiomeric resolution gave (+)-7i and (-)-7i, and the eutomer showed seven times better affinity. Although racemate (±)-7i was initially promising, the affinity of (-)-7i for VAChT was not better than 56.7 nM which precludes further preclin. evaluation. However, the nanomolar binding together with the ready synthesis of [¹¹C]-(±)-7i shows that (-)-7i can serve as a scaffold for future optimizations to provide improved ¹¹C-labeled VAChT PET tracers. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Recommanded Product: 55661-33-1).

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. 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.Recommanded Product: 55661-33-1

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

In Silico Design, Synthesis and Evaluation of Novel Series of Benzothiazole- Based Pyrazolidinediones as Potent Hypoglycemic Agents was written by Haroun, Michelyne. And the article was included in Medicinal Chemistry (Sharjah, United Arab Emirates) in 2020.Quality Control of 5,6-Dimethoxybenzo[d]thiazol-2-amine This article mentions the following:

The discovery of novel ligand binding domain (LBD) of peroxisome proliferator- activated receptor γ (PPARγ) has recently attracted attention to few research groups in order to develop more potent and safer antidiabetic agents. This study is focused on docking-based design and synthesis of novel compounds combining benzothiazole and pyrazolidinedione scaffold as potential antidiabetic agents. Several benzothiazole-pyrazolidinedione hybrids were synthesized and tested for their in vivo anti-hyperglycemic activity. Interactions profile of title compounds against PPARγ was examined through mol. modeling approach. All tested compounds exhibited anti-hyperglycemic activity similar or superior to the reference drug Rosiglitazone. Introducing chlorine atom and alkyl group at position-6 and -5 resp. on benzothiazole core resulted in enhancing the anti-hyperglycemic effect. Docking study revealed that such groups demonstrated favorable hydrophobic interactions with novel LBD Ω – pocket of PPARγ protein. Among the tested compounds, N-(6-chloro-5-methylbenzo[d]thiazol-2-yl-4-(4((3,5- dioxopyrazolidin-4-ylidene)methyl)phenoxy)butanamide) 5b was found to be the most potent compound and provided valuable insights to further develop novel hybrids as anti-hyperglycemic agents. In the experiment, the researchers used many compounds, for example, 5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6Quality Control of 5,6-Dimethoxybenzo[d]thiazol-2-amine).

5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). 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.Quality Control of 5,6-Dimethoxybenzo[d]thiazol-2-amine

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

Synthesis of 2-Aminobenzothiazole via Copper(I)-Catalyzed Tandem Reaction of 2-Iodobenzenamine with Isothiocyanate was written by Ding, Qiuping;He, Xiaodan;Wu, Jie. And the article was included in Journal of Combinatorial Chemistry in 2009.Name: N-Phenylbenzo[d]thiazol-2-amine This article mentions the following:

Copper(I)-catalyzed tandem reaction of 2-iodobenzenamines with isothiocyanates under mild conditions is described, which provides an efficient and practical route for the synthesis of 2-aminobenzothiazoles. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Name: 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. 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.Name: N-Phenylbenzo[d]thiazol-2-amine

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