Heterocyclic Building Blocks-Thiazole

Hydroxybiphenylamide GroEL/ES inhibitors are potent antibacterials against planktonic and biofilm forms of Staphylococcus aureus was written by Kunkle, Trent;Abdeen, Sanofar;Salim, Nilshad;Ray, Anne-Marie;Stevens, Mckayla;Ambrose, Andrew J.;Victorino, Jose;Park, Yangshin;Hoang, Quyen Q.;Chapman, Eli;Johnson, Steven M.. And the article was included in Journal of Medicinal Chemistry in 2018.Computed Properties of C7H4ClNS This article mentions the following:

We recently reported the identification of a GroEL/ES inhibitor (1, N-(4-(benzo[d]thiazol-2-ylthio)-3-chlorophenyl)-3,5-dibromo-2-hydroxybenzamide) that exhibited in vitro antibacterial effects against Staphylococcus aureus comparable to vancomycin, an antibiotic of last resort. To follow up, we have synthesized 43 compound 1 analogs to determine the most effective functional groups of the scaffold for inhibiting GroEL/ES and killing bacteria. Our results identified that the benzothiazole and hydroxyl groups are important for inhibiting GroEL/ES-mediated folding functions, with the hydroxyl essential for antibacterial effects. Several analogs exhibited >50-fold selectivity indexes between antibacterial efficacy and cytotoxicity to human liver and kidney cells in cell culture. We found that MRSA was not able to easily generate acute resistance to lead inhibitors in a gain-of-resistance assay and that lead inhibitors were able to permeate through established S. aureus biofilms and maintain their bactericidal effects. In the experiment, the researchers used many compounds, for example, 2-Chlorobenzothiazole (cas: 615-20-3Computed Properties of C7H4ClNS).

2-Chlorobenzothiazole (cas: 615-20-3) belongs to thiazole derivatives. Thiazoles in peptides or their ability to bind proteins, DNA and RNA has led to many synthetic studies and new applications. 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.Computed Properties of C7H4ClNS

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

Thin-layer and gas chromatography of thiazole and benzothiazole heterocycles was written by Vernin, Gaston;Metzger, Jacques. And the article was included in Bulletin de la Societe Chimique de France in 1967.Product Details of 5351-51-9 This article mentions the following:

Compounds of the general formula I, II, and III were prepared according to known methods and the effect of different factors on their mobility was studied. The following were prepared (I, R, R1, R2, and b.p. given): H, H, H, 117-18掳; Me, H, H, 128-30掳; Et, H, H, 148掳; H, Me, Me, 133掳; H, Et, H, 145掳; H, iso-Pr, H, 171掳; H, H, Me, 141掳; H, H, Et, 162掳; Me, Me, H, 145掳; Me, H, Me, 149掳; H, Me, Me, 158掳; iso-Pr, H, H, 160掳; Pr, H, H, 175掳; iso-Bu, H, H, 172掳; tert-Bu, H, H, 180掳; neopentyl, H, H, 198掳; Cl, H, H, 142掳; Br, H, H, b20 69-71掳; iso-Pr, Me, H, b50 92掳; tert-Bu, Me, H, b50 96掳; Me, tert-Bu, H, b50 96掳; Et, tert-Bu, H, b50 108掳; iso-Pr, tert-Bu, H, b50 113掳; tert-Bu, tert-Bu, H, b50 114掳; MeS, H, H, -; EtS, H, H, -; PrS, H, H, -; iso-PrS, H, H, -; tert-BuS, H, H, -; iso-Bu, H, H, -; PhCH2S, H, H, -; SH, H, H, -; SH, Me, H, -; SH, H, Me, -; MeS, H, H, -, SH, Me, Me, -; MeS, Me, H, -; MeS, Me, Me, -; SH, Ph, H, -; (II, R, R1, and R2 given): H, H, H; H, Me, H; H, H, Me; Me, H, H; H, Me, Me; Me, Me, H; Me, Me, Me; H, Ph, H; and (III, R and b.p. given): H, 231掳; Me, 240掳; Et, 252掳; Pr, 256掳; iso-Pr, 261掳; iso-Bu, 269掳; tert-Bu, b16 138掳; neopentyl, -, m. 52掳. Thin-layer chromatog. gives a better separation than gas phase chromatog. for the 2-Me, 2-Ph, 4-Me, 4-Ph, and 2,4-di-Me compounds The mobility of methylthiazoles decreases in the following manner: 4-Me > 5-Me > 2-Me; polar effects are similar for the groups: Et, iso-Pr, and tert-Bu. Steric effects become important for the groups iso-Pr and tert-Bu. In the experiment, the researchers used many compounds, for example, 4,5-Dimethylthiazole-2(3H)-thione (cas: 5351-51-9Product Details of 5351-51-9).

4,5-Dimethylthiazole-2(3H)-thione (cas: 5351-51-9) 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.Product Details of 5351-51-9

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

Head-to-head bisbenzazole derivatives as antiproliferative agents: design, synthesis, in vitro activity, and SAR analysis was written by Ersan, Ronak Haj;Alagoz, Mehmet Abdullah;Ertan-Bolelli, Tugba;Duran, Nizami;Burmaoglu, Serdar;Algul, Oztekin. And the article was included in Molecular Diversity in 2021.Computed Properties of C9H7NO2S2 This article mentions the following:

Abstract: In the present work, a series of bisbenzazole derivatives were designed and synthesized as antiproliferative agents. The antiproliferative activity of these compounds was investigated using MTT assay. Bisbenzazole derivatives showed significant antiproliferative activity against all the four tested cancer cell lines. Among the various bisbenzazole derivatives, bisbenzoxazole derivatives exhibited the most promising anticancer activity followed by bisbenzimidazole and bisbenzothiazole derivatives All the derivatives were found to be less toxic as compared to methotrexate (pos. control) in normal human cells, indicating selective and efficient antiproliferative activity of these bisbenzazole derivatives The structure-activity relationships of heteroaromatic systems and linkers present in bisbenzazole derivatives were analyzed in detail. In silico ADMET prediction revealed that bisbenzazole is a drug-like small mol. with a favorable safety profile. Compound 31 is a potential antiproliferative hit compound that exhibits unique cytotoxic activity distinct from methotrexate. Graphic abstract: Twenty-one bisbenzoxazole derivatives have been designed synthesized and evaluated to be an antiproliferative activity against four human tumor cell lines.[graphic not available: see fulltext]. In the experiment, the researchers used many compounds, for example, 2-(Benzo[d]thiazol-2-ylthio)acetic acid (cas: 6295-57-4Computed Properties of C9H7NO2S2).

2-(Benzo[d]thiazol-2-ylthio)acetic acid (cas: 6295-57-4) 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 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 C9H7NO2S2

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

Ruthenium-catalyzed hydrosilylation of C:N bond in benzothiazole was written by Kucinski, Krzysztof;Hreczycho, Grzegorz. And the article was included in Journal of Organometallic Chemistry in 2017.SDS of cas: 2942-06-5 This article mentions the following:

Various tertiary hydrosilanes are shown to be compatible with ruthenium-catalyzed hydrosilylation of carbon-nitrogen double bond in benzothiazole. The addition reaction was successfully performed by using a catalytic amount of Ru₃(CO)₁₂. The products were isolated and characterized by IR, ¹H NMR, ¹³C NMR, ²⁹Si NMR, HRMS and MS anal. This is the first example for the catalytic hydrosilylation of benzothiazole. In the experiment, the researchers used many compounds, for example, 6-Nitrobenzothiazole (cas: 2942-06-5SDS of cas: 2942-06-5).

6-Nitrobenzothiazole (cas: 2942-06-5) belongs to thiazole derivatives. Thiazoles in peptides or their ability to bind proteins, DNA and RNA has led to many synthetic studies and new applications. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.SDS of cas: 2942-06-5

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

A podocyte-based automated screening assay identifies protective small molecules was written by Lee, Ha Won;Khan, Samia Q.;Faridi, Mohd. Hafeez;Wei, Changli;Tardi, Nicholas J.;Altintas, Mehmet M.;Elshabrawy, Hatem A.;Mangos, Steve;Quick, Kevin L.;Sever, Sanja;Reiser, Jochen;Gupta, Vineet. And the article was included in Journal of the American Society of Nephrology in 2015.Reference of 1226056-71-8 This article mentions the following:

Podocyte injury and loss mark an early step in the pathogenesis of various glomerular diseases, making these cells excellent targets for therapeutics. However, cell-based high-throughput screening assays for the rational development of podocyte-directed therapeutics are currently lacking. Here, we describe a novel high-content screening-based phenotypic assay that analyzes thousands of podocytes per assay condition in 96-well plates to quant. measure dose-dependent changes in multiple cellular features. Our assay consistently produced a Z’ value >0.44, making it suitable for compound screening. On screening with >2100 pharmacol. active agents, we identified 24 small mols. that protected podocytes against injury in vitro (1% hit rate). Among the identified hits, we confirmed an 尾1-integrin agonist, pyrintegrin, as a podocyte-protective agent. Treatment with pyrintegrin prevented damage-induced decreases in F-actin stress fibers, focal adhesions, and active 尾1-integrin levels in cultured cells. In vivo, administration of pyrintegrin protected mice from LPS-induced podocyte foot process effacement and proteinuria. Anal. of the murine glomeruli showed that LPS administration reduced the levels of active 尾1 integrin in the podocytes, which was prevented by cotreatment with pyrintegrin. In rats, pyrintegrin reduced peak proteinuria caused by puromycin aminonucleoside-induced nephropathy. Our findings identify pyrintegrin as a potential therapeutic candidate and show the use of podocyte-based screening assays for identifying novel therapeutics for proteinuric kidney diseases. In the experiment, the researchers used many compounds, for example, N-Benzyl-2-(pyrimidin-4-ylamino)thiazole-4-carboxamide (cas: 1226056-71-8Reference of 1226056-71-8).

N-Benzyl-2-(pyrimidin-4-ylamino)thiazole-4-carboxamide (cas: 1226056-71-8) 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.Reference of 1226056-71-8

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

Isolation and characterization of a highly virulent Edwardsiella piscicida strain responsible for mass mortality in marbled eel (Anguilla marmorata) cultured in Korea was written by Jung, Won Joon;Kwon, Jun;Giri, Sib Sankar;Kim, Sang Guen;Kim, Sang Wha;Kang, Jeong Woo;Lee, Sung Bin;Lee, Young Min;Oh, Woo Taek;Jun, Jin Woo;Park, Se Chang. And the article was included in Aquaculture in 2022.Product Details of 78110-38-0 This article mentions the following:

Edwardsiella infections have the potential to induce immense economic losses by affecting multiple fish species, and have been increasingly reported in aquaculture. Edwardsiella tarda, Edwardsiella hoshinae, and Edwardsiella ictaluri have all been previously associated with mass mortality. Recent technol. advances in bacterial identification have identified E. piscicida and E. anguillarum as important pathogens affecting global fisheries. Strains previously identified as E. tarda have been re-grouped based on new sequence data and phylogenetic studies. E. piscicida was classified as a novel species in 2012 and has since been reported to have caused mortality in diverse fish species in numerous countries that are potentially more threatening than the mortality caused by E. tarda. Eels are one of the most consumed fish species in Asia, and Anguilla japonica is a commonly reared species in fisheries. However, due to increasing global eel consumption, attempts to culture marbled eel (A. marmorata) have been recently carried out in many Asian countries including Korea. The external clin. signs of Edwardsiella piscicida- infected marbled eel (A. marmorata) were enlarged liver, hemorrhagic congestion at the base of fins and on the skin, as well as hemorrhagic ascites and multifocal abscesses were found in the liver. Histopathol. on E. piscicida- infected tissues revealed bacteremia, multifocal necrotizing hepatitis with vasculitis and splenitis with vasculitis. This study reports the first E. piscicida infection case responsible for mass mortality in A. marmorata cultured in Korea. Our study focused on the isolation and histopathol. characterization of this bacterial strain to better understand its damage on A. marmorata. In the experiment, the researchers used many compounds, for example, 2-((((Z)-1-(2-Aminothiazol-4-yl)-2-(((2S,3S)-2-methyl-4-oxo-1-sulfoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid (cas: 78110-38-0Product Details of 78110-38-0).

2-((((Z)-1-(2-Aminothiazol-4-yl)-2-(((2S,3S)-2-methyl-4-oxo-1-sulfoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid (cas: 78110-38-0) 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 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.Product Details of 78110-38-0

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

Emergence and evolution of unique plasmids harboring blaIMP-70 and blaCTX-M-253 in multidrug-resistant Providencia rettgeri was written by Watanabe, Mako;Nakano, Ryuichi;Tanouchi, Ayako;Nakano, Akiyo;Suzuki, Yuki;Saito, Kai;Sakata, Ryuji;Ogawa, Miho;Yano, Hisakazu. And the article was included in Microbiology Spectrum in 2022.HPLC of Formula: 78110-38-0 This article mentions the following:

Although the prevalence of carbapenem-resistant Enterobacterales remains low in Japan, these bacteria are a growing problem worldwide, owing to their multidrug resistance phenotype. We isolated a multidrug-resistant Providencia rettgeri strain, NR1418, harboring a rare blaIMP variant, blaIMP-70, a novel blaCTX-M variant, designated blaCTX-M-253, and blaMOX-1. This strain is resistant to 尾-lactams, amikacin, levofloxacin, and colistin. Genomic anal. revealed that NR1418 carries two plasmids, designated pNR1418-1 and pNR1418-2. The pNR1418-1 plasmid harbors blaCTX-M-253, blaTEM-1, and blaMOX-1, while the pNR1418-2 plasmid harbors blaIMP-70, which is located in a class 1 integron. Both plasmids exhibit high similarities with the plasmid of the P. rettgeri isolate BML2526, which also harbors blaIMP-70 and was identified in the same region of Japan as NR1418 at a different point in time. This indicates the possibility of the emergence and evolution of IMP-70-producing P. rettgeri and suggests that the plasmid of BML2526 may have occurred following recombination of the two plasmids harbored by NR1418. Further, blaIMP-70 and blaCTX-M-253 were found on unique plasmids, indicating that they likely evolved through mutations and recombination. In the experiment, the researchers used many compounds, for example, 2-((((Z)-1-(2-Aminothiazol-4-yl)-2-(((2S,3S)-2-methyl-4-oxo-1-sulfoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid (cas: 78110-38-0HPLC of Formula: 78110-38-0).

2-((((Z)-1-(2-Aminothiazol-4-yl)-2-(((2S,3S)-2-methyl-4-oxo-1-sulfoazetidin-3-yl)amino)-2-oxoethylidene)amino)oxy)-2-methylpropanoic acid (cas: 78110-38-0) belongs to thiazole derivatives. Thiazole is a five-membered, unsaturated, planar, 蟺-excessive heteroaromatic containing one sulfur atom and one pyridine-type nitrogen atom at position 3 of the cyclic ring system. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.HPLC of Formula: 78110-38-0

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

Copper Acetate-Catalyzed, Mild, Highly Efficient, and Practical Synthesis of Thiazoles and Aminothiazoles was written by Meshram, H. M.;Kumar, D. Aravind;Vara Prasad, B. Ramalinga. And the article was included in Synthetic Communications in 2009.Application of 74370-93-7 This article mentions the following:

A mild and highly efficient synthesis of thiazoles by the condensation of 伪-bromo ketones with thiourea in the presence of a catalytic amount of copper acetate at room temperature has been described. The method is applicable for a variety of aryl and alkyl 伪-bromo ketones. The catalyst is inexpensive, and substituted thiazoles are obtained in good yields. In the experiment, the researchers used many compounds, for example, 4-(tert-Butyl)thiazol-2-amine (cas: 74370-93-7Application of 74370-93-7).

4-(tert-Butyl)thiazol-2-amine (cas: 74370-93-7) 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.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Application of 74370-93-7

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

Comparative examination of compatibility of potassium canrenoate (Soldactone) at the clinical usage was written by Ozawa, Kazuo;Abe, Seiji;Nemoto, Akiko;Ito, Yoko;Satoh, Kazue;Yamamoto, Toshinori;Murayama, Jun-Ichiro. And the article was included in Iryo Yakugaku in 2002.Recommanded Product: (6R,7R)-7-(2-(2-Aminothiazol-4-yl)acetamido)-3-(((1-(2-(dimethylamino)ethyl)-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid dihydrochloride This article mentions the following:

The authors examined the compatibility of a commercialized potassium canrenoate preparation (Soldactone) with 124 other kinds of currently prescribed injectable preparations as counter substances based upon the physicochem. parameters. The appearance, pH, and the concentration of canrenoate were used as markers after mixing for 24 h with other injectable preparations, since appearances can be deceptive. In order to estimate the remaining content of canrenoate after mixing, the concentrations of canrenoate were determined by UV absorption at the wavelength of 293 nm, using a spectrophotometer and reversed phase high-performance liquid chromatog. (HPLC). As the results, no change was detected in 53 of the 124 counter preparations in the mixture and the content of canrenoate was above 90%. Sixteen total parenteral nutrition solutions, 5 amino acid solutions and 17 antibiotics dissolved in saline were incompatible with canrenoate. We also examined the compatibility of canrenoate, which was directly added to furosemide (20 mg and 100 mg) and 5% of glucose preparations In the case of a furosemide injection (20mg), the appearance, pH and turbidity did not change, while the concentration of canrenoate decreased to less than 90% of the control. On the other hand, a glucose preparation (5%) did not show any incompatibility with the counter preparations Therefore, the canrenoate preparations can be dissolved into 5% glucose solution, prior to the clin. application. In the experiment, the researchers used many compounds, for example, (6R,7R)-7-(2-(2-Aminothiazol-4-yl)acetamido)-3-(((1-(2-(dimethylamino)ethyl)-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid dihydrochloride (cas: 66309-69-1Recommanded Product: (6R,7R)-7-(2-(2-Aminothiazol-4-yl)acetamido)-3-(((1-(2-(dimethylamino)ethyl)-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid dihydrochloride).

(6R,7R)-7-(2-(2-Aminothiazol-4-yl)acetamido)-3-(((1-(2-(dimethylamino)ethyl)-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid dihydrochloride (cas: 66309-69-1) 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.Recommanded Product: (6R,7R)-7-(2-(2-Aminothiazol-4-yl)acetamido)-3-(((1-(2-(dimethylamino)ethyl)-1H-tetrazol-5-yl)thio)methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid dihydrochloride

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

One-dimensional La(III) coordination polymer displaying multi-responsive luminescence activities towards Fe³⁺, acetone and benzothiozoles was written by Chen, Yuqian;Xian, Guoxuan;Yan, Hui;Wang, Yuhao;Li, Yunwu;Lu, Jing;Xu, Haijun;Tao, Jiayu;Wang, Suna. And the article was included in Journal of Solid State Chemistry in 2021.HPLC of Formula: 615-20-3 This article mentions the following:

Through reaction of La(NO₃)₃ with a flexible carboxylic acid ligand named 3,5-bis[(2-carboxyphenyl)oxy]benzoic acid (H₃L) under solvothermal condition, the complex with the formula of [La(L)(DMF)₂] (1) was obtained. One-dimensional chain of the complex was generated through the connection of binuclear units of La₂(COO)₄ across the flexible acid ligands. Luminescence results showed that different pollutants (Fe³⁺, acetone and benzothiophene organic compounds) could quench the luminescence of the blue emission of the complex in DMF with much low detection limit. Among several 2-substituted benzothiophene compounds, 2,2鈥?dithiobisbenzothiazole (DM) has a strongest binding constant of 10.8 x 10⁴ M^-1 and lowest detection limit of 0.332 渭M (0.110 ppm). All quenching effect was found within 15 s. The sensing mechanism was investigated through a series of experiments and theor. calculation Complex 1 could be employed as a multi-responsive chemosensor for detection of different pollutants with high sensitivity and fast response. In the experiment, the researchers used many compounds, for example, 2-Chlorobenzothiazole (cas: 615-20-3HPLC of Formula: 615-20-3).

2-Chlorobenzothiazole (cas: 615-20-3) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). 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: 615-20-3

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