Heterocyclic Building Blocks-Thiazole

On July 1, 2020, Amorim, Carina R.; Pavani, Thais F. A.; Lopes, Andrey F. S.; Duque, Marcelo D.; Mengarda, Ana C. A.; Silva, Marcos P.; de Moraes, Josue; Rando, Daniela G. G. published an article.Name: 4-Phenylthiazol-2-amine The title of the article was Schiff bases of 4-Phenyl-2-Aminothiazoles as hits to new antischistosomals: Synthesis, in-vitro, in-vivo and in-silico studies. And the article contained the following:

The synthesis of seventeen Schiff bases of 4-(4-Substituted phenyl)-N-(4-substituted benzylidene)thiazole-2-amines I [X = S, CH=CH; Z =H, O2N; R = H, 4-Me, 4-Et] which were tested in-vitro and in-vivo against Schistosoma mansoni adult worms. Moreover, in-silico studies to propose potential macromol. targets and to predict the oral bioavailability were also performed. The analog I [X = S; Z = O2N; R = H] exhibited the best in-vitro performance (IC50: 29.4μM, SI:6.1) associated with promising in-vivo activity, with a significant decrease in the adult life forms and oviposition. Oral bioavailability was impaired by the predicted low water solubility of I [X = S; Z = O2N; R = H] although it also exhibited good membrane permeability. The water solubility, however, was improved by decreasing the particles size. Serine/Threonine- and Tyrosine Kinases, Carbonic Anhydrase, Tyrosine Phosphatase and Arginase were predicted as potential macromol. targets through which the I [X = S; Z = O2N; R = H] was acting against the helminth. This class of compounds I exhibited an interesting initial therapeutic profile with the advantage of being chem. diverse from the PZQ and be easily synthesized from com. reagents which could lead to low-cost drugs. These aspects make this class of compounds I interesting hits to be explored against schistosomiasis. The experimental process involved the reaction of 4-Phenylthiazol-2-amine(cas: 2010-06-2).Name: 4-Phenylthiazol-2-amine

The Article related to phenyl aminothiazole diastereoselective preparation antischistosomal agent mol modeling, 4-phenyl-2-aminothiazoles, antischistosomal, schiff bases, schistosoma mansoni, target fishing and other aspects.Name: 4-Phenylthiazol-2-amine

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

On August 26, 2003, Bizzarro, Fred Thomas; Corbett, Wendy Lea; Grippo, Joseph Francis; Haynes, Nancy-Ellen; Holland, George William; Kester, Robert Francis; Mahaney, Paige Erin; Sarabu, Ramakanth published a patent.Application In Synthesis of Methyl 2-(2-aminothiazol-4-yl)acetate The title of the patent was Preparation of cycloalkylheteroaryl propionamides as glucokinase activators for treatment of type II diabetes. And the patent contained the following:

Title compounds [I; R1, R2 = H, halo, amino, hydroxyamino, NO2, cyano, sulfonamido, perfluoroalkyl, alkylthio, alkylsulfonyl, alkylsulfinyl, etc.; R3 = alkyl, cycloalkyl; R4 = certain un- or monosubstituted 5- and 6-membered heteroaromatic rings connected by a ring C atom; R4 (claims) = un- or monosubstituted triazine, pyrazine, or pyridazine; and their pharmaceutical acceptable salts], were prepared via amidation, for use as glucokinase activators for treatment of type II diabetes. Thus, the invention compound N-(5-chlorothiazol-2-yl)-3-cyclopentyl-2(R)-[4-(methanesulfonyl)phenyl]propionamide (II) was prepared by addition of 3-cyclopentyl-2(R)-[4-(methanesulfonyl)phenyl]propionic acid (preparation given) to a stirred mixture of triphenylphosphine and N-bromosuccinimide in methylene chloride at 0°, followed by stirring at room temperature for 30 min, addition of a solution of 2-amino-5-chlorothiazole hydrochloride and pyridine in methylene chloride, and stirring at 25° overnight. All of the exemplified compounds I activated glucokinase in vitro, exhibiting an SC1.5 ≤ 30 μM. Selected invention compounds exhibited glucokinase activator activity in vivo when administered orally to mice. Thus, I are expected to increase insulin secretion in the treatment of type II diabetes. The experimental process involved the reaction of Methyl 2-(2-aminothiazol-4-yl)acetate(cas: 64987-16-2).Application In Synthesis of Methyl 2-(2-aminothiazol-4-yl)acetate

The Article related to cycloalkylheteroaryl propionamide preparation thiazolyl glucokinase activator diabetes, antidiabetic thiazole pyrazine pyridazine pyridine pyrimidine glucokinase activator preparation and other aspects.Application In Synthesis of Methyl 2-(2-aminothiazol-4-yl)acetate

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

Hussein, Awaz Jamil; Azeez, Hashim Jalal published an article in 2013, the title of the article was Synthesis and antimicrobial activity of some new thiazolidin-4-one derivatives of 4-(6-methylbenzo[d]thiazol-2-yl)benzamine.COA of Formula: C14H12N2S And the article contains the following content:

A number of derivatives of 2-(substituted phenyl)-3-(4-(6-methylbenzo[d]thiazol-2-yl)phenyl)thiazolidin-4-one were synthesized from the reaction of 4-(6-methylbenzo[d]thiazol-2-yl)benzenamine with different substituted benzaldehydes followed by cyclocondensation reaction of the prepared imines with 2-mercaptoacetic acid in high yields. Furthermore, the structures of the newly synthesized compounds were confirmed by FT-IR, 13C-NMR, 13C-DEPT, and 1H-NMR spectral data. The imines and thiazolidin-4-one derivatives were evaluated for their antibacterial activity against Escherichia coli as gram neg. and Staphylococcus aureus as gram pos., the results have shown significant activity against both types of bacteria. The experimental process involved the reaction of 2-(4-Aminophenyl)-6-methylbenzothiazole(cas: 92-36-4).COA of Formula: C14H12N2S

The Article related to benzothiazolylaniline aryl aldehyde condensation, schiff base preparation antibacterial cyclization mercaptoacetate, aryl benzothiazolylphenyl thiazolidinone preparation antibacterial and other aspects.COA of Formula: C14H12N2S

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

On December 31, 2021, Lemilemu, Fitsum; Bitew, Mamaru; Demissie, Taye B.; Eswaramoorthy, Rajalakshmanan; Endale, Milkyas published an article.HPLC of Formula: 2010-06-2 The title of the article was Synthesis, antibacterial and antioxidant activities of Thiazole-based Schiff base derivatives: a combined experimental and computational study. And the article contained the following:

Thiazole-based Schiff base compounds display significant pharmacol. potential with an ability to modulate the activity of many enzymes involved in metabolism They also demonstrated to have antibacterial, antifungal, anti-inflammatory, antioxidant, and antiproliferative activities. In this work, conventional and green approaches using ZnO nanoparticles as catalyst were used to synthesize thiazole-based Schiff base compounds Among the synthesized compounds, 11 showed good activities towards Gram-neg. E. coli (14.40 ± 0.04), and Gram-pos. S. aureus (15.00 ± 0.01 mm), resp., at 200 μg/mL compared to amoxicillin (18.00 ± 0.01 mm and 17.00 ± 0.04). Compounds 7 and 9 displayed better DPPH radical scavenging potency with IC50 values of 3.6 and 3.65 μg/mL, resp., compared to ascorbic acid (3.91 μg/mL). The binding affinity of the synthesized compounds against DNA gyrase B is within – 7.5 to – 6.0 kcal/mol, compared to amoxicillin (- 6.1 kcal/mol). The highest binding affinity was achieved for compounds 9 and 11 (- 6.9, and – 7.5 kcal/mol, resp.). Compounds 7 and 9 displayed the binding affinity values of – 5.3 to – 5.2 kcal/mol, resp., against human peroxiredoxin 5. These values are higher than that of ascorbic acid (- 4.9 kcal/mol), in good agreement with the exptl. findings. In silico cytotoxicity predictions showed that the synthesized compounds LD (LD50) value are class three (50 ≤ LD50 ≤ 300), indicating that the compounds could be categorized under toxic class. D. functional theory calculations showed that the synthesized compounds have small band gap energies ranging from 1.795 to 2.242 eV, demonstrating that the compounds have good reactivities. The synthesized compounds showed moderate to high antibacterial and antioxidant activities. The in vitro antibacterial activity and mol. docking anal. showed that compound 11 is a promising antibacterial therapeutics agent against E. coli, whereas compounds 7 and 9 were found to be promising antioxidant agents. Moreover, the green synthesis approach using ZnO nanoparticles as catalyst was found to be a very efficient method to synthesize biol. active compounds compared to the conventional method. The experimental process involved the reaction of 4-Phenylthiazol-2-amine(cas: 2010-06-2).HPLC of Formula: 2010-06-2

The Article related to thiazole schiff base derivative antibacterial antioxidant activity computational biol, antibacterial, antioxidant, dft analysis, drug likeness, molecular docking, schiff base, thiazole and other aspects.HPLC of Formula: 2010-06-2

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

Vibhute, Prashant K.; Aghao, Arvind K.; Jadhav, Satish B.; Dawane, Bhaskar S. published an article in 2021, the title of the article was Design, synthesis and characterization of some novel thiazole and quinoline containing schiff bases and evaluation of their in-vitro anti-inflammatory and antimicrobial activity.Category: thiazole And the article contains the following content:

A novel and eco-friendly series of quinoline based Schiff bases I [R = H, 4-Cl, 4-Br, etc.] in PEG-400 were synthesized. It contd. two pharmacol. active nucleus i.e. 8-hydroxyquinoline and 4-substituted phenylthiazole. The targeted compounds were obtained in good yield by reacting 2-amino-4-substituted phenylthiazole with 8-hydroxyquinoline-2-carbaldehyde which was obtained by oxidative product of 8-hydroxy-2-Me quinoline. The mol. structures of the synthesized compounds I were confirmed by physicochem. properties and spectral characteristics (IR, NMR, elemental anal. and Mass spectra). The synthesized compounds I were screened for the in-vitro anti-inflammatory and antimicrobial activity. Thiazole quinoline Schiff base could be a promising mol. in developing area of antimicrobial agents for modern pharmacologists and chemists. The experimental process involved the reaction of 4-Phenylthiazol-2-amine(cas: 2010-06-2).Category: thiazole

The Article related to hydroxyquinoline carbaldehyde phenylthiazole diastereoselective schiff imination green chem, phenylthiazolyliminomethyl quinolinol preparation antiinflammatory antibacterial antifungal and other aspects.Category: thiazole

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

On May 16, 2022, Kong, Weixi; Liu, Yunting; Huang, Chen; Zhou, Liya; Gao, Jing; Turner, Nicholas J.; Jiang, Yanjun published an article.Reference of 2-Acetylthiazole The title of the article was Direct Asymmetric Reductive Amination of Alkyl (Hetero)Aryl Ketones by an Engineered Amine Dehydrogenase. And the article contained the following:

The direct asym. reductive amination of heteroaryl ketones has been a long-standing synthetic challenge. Here we report the engineering of an amine dehydrogenase (AmDH) from Jeotgalicoccus aerolatus for the asym. synthesis of chiral α-(hetero)aryl primary amines in excellent conversions (up to 99%) and enantioselectivities (up to 99% ee). The best AmDH variant (Ja-AmDH-M33) exhibited high activity and specificity toward alkyl (hetero)aryl ketones, even for those bearing a bulky alkyl chain. An efficient directed evolution approach based on mol. docking was implemented to enlarge the active pocket with a more hydrophobic entrance, which is responsible for the high activity. The Ja-AmDH-M33 was also used for preparative-scale synthesis of pharmaceutically relevant amines and a key intermediate of chiral pincer ligands, which highlighted its practical application in synthetic chem. The experimental process involved the reaction of 2-Acetylthiazole(cas: 24295-03-2).Reference of 2-Acetylthiazole

The Article related to jeotgalicoccus amination alkyl aryl ketone amine dehydrogenase mutation, alkyl (hetero)aryl ketones, amine dehydrogenase, asymmetric reductive amination, chiral amines, directed evolution and other aspects.Reference of 2-Acetylthiazole

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

On June 15, 2021, Hassan, Abdelfattah; Badr, Mohamed; Hassan, Heba A.; Abdelhamid, Dalia; Abuo-Rahma, Gamal El-Din A. published an article.Category: thiazole The title of the article was Novel 4-(piperazin-1-yl)quinolin-2(1H)-one bearing thiazoles with antiproliferative activity through VEGFR-2-TK inhibition. And the article contained the following:

A new series of 2-(4-(2-oxo-1,2-dihydroquinolin-4-yl)piperazin-1-yl)-N-(4-phenylthiazol-2-yl)acetamide derivatives were synthesized and evaluated for anticancer activity. All target compounds showed anticancer activity higher than that of their 2-oxo-4-piperazinyl-1,2-dihydroquinolin-2(1H)-one precursors. Multidose testing of target compounds was performed against breast cancer T-47D cell line. Five compounds showed higher cytotoxic activity than Staurosporine. The dihalogenated derivative showed the best cytotoxic activity with IC50 2.73 +/= 0.16μM. In addition, the VEGFR-2 inhibitory activity of all synthetic compounds was evaluated. Two compounds of 6-fluoro-4-(piperazin-1-yl)quinolin-2(1H)-ones showed inhibitory activity comparable to sorafenib with IC50 46.83 +/= 2.4, 51.09 +/= 2.6 and 51.41 +/= 2.3 nM, resp. The cell cycle anal. of two compounds namely, 2-(4-(6-fluoro-2-oxo-1,2-dihydroquinolin-4-yl)piperazin-1-yl)-N-(4-phenylthiazol-2-yl)acetamide and N-(4-(4-chlorophenyl)thiazol-2-yl)-2-(4-(2-oxo-1-phenyl-1,2-dihydroquinolin-4-yl)piperazin-1-yl)acetamide revealed that the arrest of cell cycle occurred at S phase. The experimental process involved the reaction of 4-Phenylthiazol-2-amine(cas: 2010-06-2).Category: thiazole

The Article related to piperazinylquinolinone thiazole preparation docking anticancer vegfr 2 inhibition human, 4-phenylthiazole, 4-piperazinylquinolin‐2(1h)-one, angiogenesis, breast cancer, vegfr‐2 inhibitors and other aspects.Category: thiazole

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

On March 20, 2012, Murray, Anthony; Lau, Jesper; Vedsoe, Per published a patent.Synthetic Route of 859522-19-3 The title of the patent was Urea glucokinase activators. And the patent contained the following:

This application relates to novel urea glucokinase activators and use of the compounds of the invention for preparation of a medicament for the treatment of various diseases, e.g. for the treatment of type 2 diabetes. Further encompassed is a pharmaceutical composition comprising a compound according to the invention and a process for preparing such. The experimental process involved the reaction of Ethyl 2-((2-aminothiazol-5-yl)thio)acetate(cas: 859522-19-3).Synthetic Route of 859522-19-3

The Article related to arylcyclopentylmethylureidothiazolylthioalkanoate preparation glucokinase activator, diabetes hyperglycemia obesity dyslipidemia treatment thiazolylthioalkanoate ureido aryl cyclopentylmethyl and other aspects.Synthetic Route of 859522-19-3

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

On July 17, 2008, Murray, Anthony; Lau, Jesper; Vedsoe, Per published a patent.Quality Control of Ethyl 2-((2-aminothiazol-5-yl)thio)acetate The title of the patent was Preparation of arylureidothiazolylthioalkanoates as glucokinase activators. And the patent contained the following:

Title compounds [I; R = CH2CO2H, CH2CMe2CO2H, CMe2CO2H; R1 = substituted (heteroaryl-fused) Ph], were prepared for treatment of diabetes, hyperglycemia, obesity, syndrome X, dyslipidemia, and impaired glucose tolerance (no data). Thus, cyclopentylmethyl(2,5-difluorophenyl)amine (preparation given), Et 3-(2-aminothiazol-5-ylsulfanyl)-2,2-dimethylpropionate (preparation given), carbonyldiimidazole, and DMAP were stirred together in THF at 40-50° to give the desired urea ester, which was saponified with aqueous NaOH in THF/MeOH to give [2-[3-cyclopentylmethyl-3-(2,5-difluorophenyl)ureido]thiazol-5-ylsulfanyl]acetic acid. The experimental process involved the reaction of Ethyl 2-((2-aminothiazol-5-yl)thio)acetate(cas: 859522-19-3).Quality Control of Ethyl 2-((2-aminothiazol-5-yl)thio)acetate

The Article related to arylcyclopentylmethylureidothiazolylthioalkanoate preparation glucokinase activator, diabetes hyperglycemia obesity dyslipidemia treatment thiazolylthioalkanoate ureido aryl cyclopentylmethyl and other aspects.Quality Control of Ethyl 2-((2-aminothiazol-5-yl)thio)acetate

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

On August 31, 2022, Ghamry, Mohamed; Ghazal, Ahmed Fathy; Al-Maqtqri, Qais Ali; Li, Li; Zhao, Wei published an article.COA of Formula: C5H5NOS The title of the article was Impact of a novel probiotic Lactobacillus strain isolated from the bee gut on GABA content, antioxidant activity, and potential cytotoxic activity against HT-29 cell line of rice bran. And the article contained the following:

Rice bran was fermented with Lactobacillus apis, isolated from the bee gut as a novel probiotic strain, and Saccharomyces cerevisiae to investigate the relationship between its metabolites and antioxidant activity, nutraceutical value, and cytotoxic activity against the HT-29 cell line. The findings showed that L. apis improved the antioxidant activity (DPPH of 37.73%) and antioxidant capacity (ABTS of 37.62 mg Trolox/g,), as well as, hydroxyl radical-scavenging activity (91.55%) of rice bran compared to S. cerevisiae. The metabolic anal. of volatile compounds revealed an increase of alcs. and lactones in the samples fermented with S. cerevisiae. While the samples fermented with L. apis displayed an increase of ketones, esters, and thiazoles. On the other hand, L. apis and S. cerevisiae exhibited a significant ability to increase γ-aminobutyric acid during different fermentation times. Compared with non-fermented samples (18.54%), L. apis increased the cytotoxic activity of rice bran against the HT-29 cell line to 34.17%, and S. cerevisiae to 31.34%. These results suggest that the fermentation of rice bran with S. cerevisiae and L. apis provides a promising strategy to improve the antioxidant activity and nutraceuticals of rice bran, and a potential source for plant-based pharmaceutical products. The experimental process involved the reaction of 2-Acetylthiazole(cas: 24295-03-2).COA of Formula: C5H5NOS

The Article related to lactobacillus apis saccharomyces cerevisiae fermentation antioxidant nutraceutical cytotoxic activity, antioxidants, cytotoxic activity, lactobacillus apis, rice bran, saccharomyces cerevisiae and other aspects.COA of Formula: C5H5NOS

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