Category: thiazole

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

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 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

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 June 30, 2019, Abo-Ashour, Mahmoud F.; Eldehna, Wagdy M.; Nocentini, Alessio; Ibrahim, Hany S.; Bua, Silvia; Abdel-Aziz, Hatem A.; Abou-Seri, Sahar M.; Supuran, Claudiu T. published an article.Synthetic Route of 2010-06-2 The title of the article was Novel synthesized SLC-0111 thiazole and thiadiazole analogues: Determination of their carbonic anhydrase inhibitory activity and molecular modeling studies. And the article contained the following:

In the presented work, we report the design and synthesis of novel SLC-0111 thiazole and thiadiazole analogs (11a-d, 12a-d, 16a-c and 17a-d). A bioisosteric replacement approach was adopted to replace the 4-fluorophenyl tail of SLC-0111 with thiazole and thiadiazole ones, which were thereafter extended with lipophilic un/substituted Ph moieties. All the newly synthesized SLC-0111 analogs were evaluated in vitro for their inhibitory activity towards a panel of the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1) isoforms (hCA I, II, IX and XII), using a stopped-flow CO2 hydrase assay. All the examined isoforms were inhibited by the primary sulfonamide derivatives (11a-d and 12a-d) in variable degrees with the following KI ranges: 162.6-7136 nM for hCA I, 9.0-833.6 nM for hCA II, 7.9-153.0 nM for hCA IX, and 9.4-94.0 nM for hCA XII. In particular, compounds 12b and 12d displayed 5.5-fold more potent inhibitory activity (KIs = 8.3 and 7.9 nM, resp.) than SLC-0111 (KI = 45 nM) towards hCA IX. Mol. docking study was carried out for 12d within the hCA IX (PDB 3IAI) active site, to justify its inhibitory activity. The experimental process involved the reaction of 4-Phenylthiazol-2-amine(cas: 2010-06-2).Synthetic Route of 2010-06-2

The Article related to carbonic anhydrase inhibitors mol docking slc0111 analogs, carbonic anhydrase inhibitors, molecular docking, slc-0111 analogues, thiazoles and thiadiazoles, ureido-benzenesulfonamide and other aspects.Synthetic Route of 2010-06-2

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

On July 31, 2009, Yotnoi, Bunlawee; Limtrakul, Jumras; Prior, Timothy; Rujiwatra, Apinpus published an article.Recommanded Product: 2-(4-Aminophenyl)-6-methylbenzothiazole The title of the article was Preparation and Characterization of Bis(μ-1,2-diaminoethane)cobalt(II) Hexavanadate: A Layered Polyoxovanadate Pillared by a Cobalt Coordination Complex. And the article contained the following:

The first example of polyoxovanadate layered framework with a cobalt coordination complex as a pillaring unit, CoII(μ-C2N2H8)2[VIV4VV2O14], was readily synthesized under hydrothermal conditions. The structure can be solved and refined in monoclinic P21/n with a 9.143(3), b 6.5034(11), c 15.874(4) Å, β = 101.90(2), V = 923.6(4) Å3 and Z = 2. The crystal structure comprises two-dimensional {VIV4VV2O14}2- layers extending parallel to [101], constructed from tetrahedral {VVO4} and square pyramidal {VIVO5} building units. Adjacent layers are linked through the octahedral {CoIIO2(μ-C2N2H8)2} pillars, within which the CoII resides on an inversion center. The structure displays N-H···O and C-H···O hydrogen bonding between the ethylenediamine and vanadium oxide layers. The experimental process involved the reaction of 2-(4-Aminophenyl)-6-methylbenzothiazole(cas: 92-36-4).Recommanded Product: 2-(4-Aminophenyl)-6-methylbenzothiazole

The Article related to cobalt diaminoethane bridge layered polyoxovanadate pillared complex hydrothermal preparation, crystal structure cobalt diaminoethane bridge layered polyoxovanadate pillared complex and other aspects.Recommanded Product: 2-(4-Aminophenyl)-6-methylbenzothiazole

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

On December 31, 2019, Kizimova, I. A.; Igidov, N. M.; Dmitriev, M. V.; Chashchina, S. V.; Makhmudov, R. R.; Siutkina, A. I. published an article.Application In Synthesis of 4-Phenylthiazol-2-amine The title of the article was Synthesis, Structure, and Biological Activity of 4-R-4-Oxo-2-[2-(phenylamino)benzoyl]hydrazinylidene-N-hetarylbutanamides. And the article contained the following:

Decyclization of N’-[5-R-2-oxofuran-3(2H)-ylidene]-2-(phenylamino)benzohydrazides I (R = Ph, t-Bu, 4-chlorophenyl, etc.) under the action of heterocyclic amines R1NH2 (R1 = thiazol-2-yl, 1,3,4-thiadiazol-2-yl, 4-phenylthiazol-2-yl, etc.) leads to the formation of N-hetaryl-4-R-4-oxo-2-[2-(phenylamino)benzoyl]hydrazinylidenebutanamides II and in some cases ring-chain tautomers. Antinociceptive and anti-inflammatory activities of the obtained compounds were studied. The experimental process involved the reaction of 4-Phenylthiazol-2-amine(cas: 2010-06-2).Application In Synthesis of 4-Phenylthiazol-2-amine

The Article related to hetaryl oxo phenylamino benzoyl hydrazinylidene butanamide preparation antinociceptive antiinflammatory, oxofuranylidene phenylamino benzohydrazide heterocyclic amine decyclization and other aspects.Application In Synthesis of 4-Phenylthiazol-2-amine

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

On June 18, 2009, Ellman, Jonathan A.; Brak, Katrien published a patent.Related Products of 19989-66-3 The title of the patent was Triazole derivatives and aminocoumarin derivatives as nonpeptidic inhibitors of cruzain and their preparation and use in the treatment of Chagas disease. And the patent contained the following:

Cruzain is the major cysteine protease of T. cruzi, which is the causative agent of Chagas’ disease and is a promising target for the development of chemotherapy. With the goal of developing potent nonpeptidic inhibitors of cruzain, of formula I, the substrate activity screening method was used to screen a library of protease substrates initially designed to target the homologous human protease cathepsin S. Structure-based design was next used to further improve substrate cleavage efficiency by introducing addnl. binding interactions in the S3 pocket of cruzain. Substrates of formula I wherein R1 is H, OH and derivatives, NH2 and derivatives, SH and derivatives, SOH and derivatives, SO2H and derivatives, SO2NH2 and derivatives, NO2, halo, CN, (un)substituted (hetero)alkyl, etc.; are claimed. The optimized substrates were then converted to inhibitors by the introduction of cysteine protease mechanism-based pharmacophores. Inhibitors II and III were prepared by multistep procedures (procedures given). Inhibitor II was determined to be reversible even though it incorporated the vinyl sulfone pharmacophore that is well documented to give irreversible cruzain inhibition for peptidic inhibitors. The previously unexplored β-chloro vinyl sulfone pharmacophore provided mechanistic insight that led to the development of potent irreversible acyl- and aryl- oxymethyl ketone cruzain inhibitors. For these inhibitors, potency did not solely depend on leaving group pTa, with 2,3,5,6-tetrafluorophenoxy Me ketone III identified as one of the most potent inhibitors with a second order inactivation constant of 147,000 s-1M-1. This inhibitor completely eradicated the T. cruzi parasite from mammalian cell cultures and consequently has the potential to lead to new chemo therapeutics for Chagas’ disease. The experimental process involved the reaction of Benzo[d]thiazol-6-ylmethanol(cas: 19989-66-3).Related Products of 19989-66-3

The Article related to triazole derivative preparation nonpeptidic cruzain inhibitor treatment chagas disease, aminocoumarin derivative preparation nonpeptidic cruzain inhibitor treatment chagas disease and other aspects.Related Products of 19989-66-3

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

On December 1, 2015, Maracic, Silvija; Kraljevic, Tatjana Gazivoda; Paljetak, Hana Cipcic; Peric, Mihaela; Matijasic, Mario; Verbanac, Donatella; Cetina, Mario; Raic-Malic, Silvana published an article.Safety of 2-(4-Aminophenyl)-6-methylbenzothiazole The title of the article was 1,2,3-Triazole pharmacophore-based benzofused nitrogen/sulfur heterocycles with potential anti-Moraxella catarrhalis activity. And the article contained the following:

Versatile 1,2,3-triazole pharmacophore-based benzofused heterocycles containing halogen-substituted aromatic, 7-substituted coumarin or penciclovir-like subunit were designed and synthesized to evaluate their antibacterial activities against selected Gram-pos. and Gram-neg. bacteria. Hybridization approach using environmentally friendly Cu(I)-catalyzed click reaction under microwave irradiation was adopted in the synthesis of regioselective 1,4-disubstituted 1,2,3-triazole tethered heterocycles, while post-N-alkylation of NH-1,2,3-triazoles afforded both 2,4- and 1,4-disubstituted 1,2,3-triazole regioisomers. Several compounds revealed fluorescence in the violet region of the visible spectrum with a strong influence of Ph spacer in 25-30 on both wavelength and emission intensity. Fusion of selected subunits led to new hybrid architecture, benzothiazole-1,2,3-triazolecoumarin derivative I that demonstrated extremely narrow spectrum activity towards fastidious Gram-neg. bacteria Moraxella catarrhalis. Selected hybrids showed the potency against Moraxella catarrhalis (MIC ≤ 0.25 μg/mL) comparable to that of reference antibiotic azithromycin, which suggested that further investigations are necessary to optimize this potential hit compound as a new anti-Moraxella catarrhalis agent. The experimental process involved the reaction of 2-(4-Aminophenyl)-6-methylbenzothiazole(cas: 92-36-4).Safety of 2-(4-Aminophenyl)-6-methylbenzothiazole

The Article related to moraxella catarrhalis antibacterial triazole heterocycle preparation, 1,2,3-triazole, antibacterial activity, coumarin, fluorescence, hybridization approach, moraxella catarrhalis and other aspects.Safety of 2-(4-Aminophenyl)-6-methylbenzothiazole

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

Gaddam, Lakshmi Teja; Thata, Sreenivasulu; Adivireddy, Padmaja; Venkatapuram, Padmavathi published an article in 2019, the title of the article was Synthesis of carboxamide and sulfonyl carboxamide linked heterocycles under green conditions.HPLC of Formula: 2010-06-2 And the article contains the following content:

Direct coupling of heteroaldehydes RCHO (R = furan-2-yl, pyridin-4-yl, 2,4-dichloro-1,3-oxazol-5-yl, etc.) with heteroaryl amines R1NH2 (R1 = 4-phenyl-1H-imidazol-2-yl, 4-phenyl-1,3-thiazol-2-yl)/sulfonylamine N-(5-(aminosulfonyl)-4-phenyl-1H-imidazol-2-yl)benzamide is performed under green conditions using PEG-400 in the presence of oxidant CCl3CN/H2O2. The presence of electron withdrawing substituents on heteroaldehydes increased the yield. Further heteroaryl amines favor the reaction when compared with heteroaryl sulfonylamines. 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 carboxamide preparation green chem, heteroaldehyde heteroaryl amine coupling reaction, sulfonyl carboxamide preparation green chem, sulfonylamine heteroaldehyde coupling reaction and other aspects.HPLC of Formula: 2010-06-2

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