Category: thiazole

Synthesis and antimicrobial activity of new 3,5-diarylidene-4-piperidone derivatives was written by Singaram, Kulathooran;Marimuthu, Dhamodaran;Baskaran, Selvakumar;Ramaswamy, Venkataraman. And the article was included in Journal of the Serbian Chemical Society in 2016.Electric Literature of C6H7ClN2O3S2 This article mentions the following:

Three series of heteroaromatic analogs diarylidene-4-piperidones I [Ar = C₆H₅, 4-FC₆H₄, 2-thienyl, etc.], [diarylidene(substituted)sulfonyl]piperidin-4-ones II [R¹ = 3,5-Cl₂-2-OHC₆H₂, 4-Cl-3-pyridyl, 3,5-Me₂-4-isoxazolyl, etc.] and N-alkylcarbonyl-diarylidene-4-piperidones derivatives e.g., III, were synthesized. All the synthesized compounds were evaluated for their antimicrobial activity against six microbial strains, among them II [R¹ = 3,5-Cl₂-2-OHC₆H₂] showed best antifungal activity against Aspergillus niger and A. fumigatus. Structural elucidation of the synthesized compounds was realized based on various spectroscopic methods. In the experiment, the researchers used many compounds, for example, 2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9Electric Literature of C6H7ClN2O3S2).

2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9) 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 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.Electric Literature of C6H7ClN2O3S2

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

Discovery of triazolone derivatives as novel, potent stearoyl-CoA desaturase-1 (SCD1) inhibitors was written by Sun, Shaoyi;Zhang, Zaihui;Pokrovskaia, Natalia;Chowdhury, Sultan;Jia, Qi;Chang, Elaine;Khakh, Kuldip;Kwan, Rainbow;McLaren, David G.;Radomski, Chris C.;Ratkay, Leslie G.;Fu, Jianmin;Dales, Natalie A.;Winther, Michael D.. And the article was included in Bioorganic & Medicinal Chemistry in 2015.Application In Synthesis of Thiazol-2-ylmethanamine This article mentions the following:

Stearoyl-CoA deaturase-1 (SCD1) plays an important role in lipid metabolism Inhibition of SCD1 activity represents a potential novel approach for the treatment of metabolic diseases such as obesity, type 2 diabetes and dyslipidemia, as well as skin diseases, acne and cancer. Herein, we report the synthesis and structure-activity relationships (SAR) of a series of novel triazolone derivatives, culminating in the identification of pyrazolyltriazolone (I), a potent SCD1 inhibitor, which reduced plasma C16:1/C16:0 triglycerides desaturation index (DI) in an acute Lewis rat model in a dose dependent manner, with an ED₅₀ of 4.6 mg/kg. In preliminary safety studies, compound I did not demonstrate adverse effects related to SCD1 inhibition after repeat dosing at 100 mg/kg. Together, these data suggest that sufficient safety margins can be achieved with certain SCD1 inhibitors, thus allowing exploration of clin. utility in metabolic disease settings. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Application In Synthesis of Thiazol-2-ylmethanamine).

Thiazol-2-ylmethanamine (cas: 55661-33-1) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). 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.Application In Synthesis of Thiazol-2-ylmethanamine

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

Synthesis and biological evaluation of 4β-sulphonamido and 4β-[(4′-sulphonamido)benzamide]podophyllotoxins as DNA topoisomerase-IIα and apoptosis inducing agents was written by Kamal, Ahmed;Suresh, Paidakula;Ramaiah, M. Janaki;Mallareddy, Adla;Imthiajali, Syed;Pushpavalli, S. N. C. V. L.;Lavanya, A.;Pal-Bhadra, Manika. And the article was included in Bioorganic & Medicinal Chemistry in 2012.HPLC of Formula: 69812-29-9 This article mentions the following:

A series of new 4β-sulfonamido and 4β-[(4′-sulfonamido)benzamide] conjugates of podophyllotoxin (11a-j and 15a-g) were synthesized and evaluated for anticancer activity against six human cancer cell lines and found to be more potent than etoposide. Some of the compounds 11b, 11d and 11e that showed significant antiproliferative activity in Colo-205 cells, were superior to etoposide. The flow cytometric anal. indicates that these compounds (11b, 11d and 11e) showed G2/M cell cycle arrest and among them 11e is the most effective. It is observed that this compound (11e) caused both single-strand DNA breaks as observed by comet assay as well as double-strand DNA breaks as indicated by γ-H2AX. Further 11e showed inhibition of topo-IIα as observed from Western blot anal. and related studies. Compounds caused activation of ATM as well as Chk1 protein indicating that the compound caused effective DNA damage. Moreover activation of caspase-3, p21, p16, NF-kB and down regulation of Bcl-2 protein suggests that this compound (11e) has apoptotic cell death inducing ability, apart from acting as a topo-IIα inhibitor. In the experiment, the researchers used many compounds, for example, 2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9HPLC of Formula: 69812-29-9).

2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9) 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.HPLC of Formula: 69812-29-9

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

Iron-catalyzed tandem reactions of 2-halobenzenamines with isothiocyanates leading to 2-aminobenzothiazoles was written by Qiu, Jing-Wen;Zhang, Xing-Guo;Tang, Ri-Yuan;Zhong, Ping;Li, Jin-Heng. And the article was included in Advanced Synthesis & Catalysis in 2009.SDS of cas: 1843-21-6 This article mentions the following:

A highly practical method for the synthesis of 2-aminobenzothiazoles has been developed through an iron-catalyzed tandem reaction. The present tandem process allows the assembly of a wide range of 2-aminobenzothiazoles by the reactions of 2-halobenzenamines with isothiocyanates. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6SDS of cas: 1843-21-6).

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

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

Synthesis of 2-mercaptobenzothiazole using nitrobenzene and H₂S as starting materials was written by Li, Jinghua;Li, Zhenqiu;Yu, Guang;Song, Yuye. And the article was included in Qingdao Keji Daxue Xuebao, Ziran Kexueban in 2009.Reference of 1843-21-6 This article mentions the following:

H₂S which was the byproduct from 2-mercaptobenzothiazole synthesis process reacted with nitrobenzene to prepare aniline and the obtained aniline was directly used to synthesize 2-mercaptobenzothiazole. The sulfur obtained from reduction process was used as material for synthesizing 2-mercaptobenzothiazole. That is to say the byproducts H₂S and sulfur could be utilized circularly. Under the conditions of 80-100°C, certain pressure and 3-4 h, the yield of aniline could reach 6.619%. The feasibility of experiment was done by directly adding sulfur dissolved in carbon disulfide into the reduction mixture to prepare 2- mercaptobenzothiazole. A new clean synthesis method of 2-mercaptobenzothiazole with lower cost is explored. 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. 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.Reference of 1843-21-6

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

Synthesis and fungicidal activity of N,S-substituted α-thio-β-aminocrotonanilides was written by Pierce, James B.;Fanning, Robert J.;Davis, Robert Allan. And the article was included in Canadian Journal of Chemistry in 1975.Application In Synthesis of N-Phenylbenzo[d]thiazol-2-amine This article mentions the following:

A number of N,S-substituted α-thio-β-aminocrotonanilides have been synthesized. Their fungicidal activity on a number of organisms has been studied and in general it has been found that it is inferior to that of the 1,4-oxathiins to which these compounds bear some structural similarities. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Application In Synthesis of 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. 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.Application In Synthesis of N-Phenylbenzo[d]thiazol-2-amine

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

A Cu₂O/TBAB-promoted approach to synthesize heteroaromatic 2-amines via one-pot cyclization of aryl isothiocyanates with ortho-substituted amines in water was written by Zhang, Jinli;Chen, Ling;Dong, Yibo;Yang, Jinchen;Wu, Yangjie. And the article was included in Organic & Biomolecular Chemistry in 2020.Formula: C13H10N2S This article mentions the following:

An efficient approach to synthesize heteroaromatic 2-amines from one-pot desulfurization/dehydrogenative cyclization of aryl isothiocyanates with ortho-substituted amines in water was developed. This approach tolerated a wide range of functional groups on the aromatic ring, providing a practical and environment-friendly process to synthesize heteroaromatic 2-amines in moderate to excellent yields. A plausible mechanism was proposed and the role of TBAB and Cu₂O in the present strategy was suggested with the help of ESI mass spectrometry. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Formula: C13H10N2S).

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

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

Infrared and Raman study of monophenylthiazoles. Use of force fields of thiazole and benzene in the theoretical calculation of vibrational frequencies. Application to the determination of the dihedral angles of monophenylthiazoles was written by Conte, M.;Mille, G.;Avignon, T.;Metzger, J.. And the article was included in Analusis in 1976.COA of Formula: C9H7NS This article mentions the following:

The ir and Raman spectra of 2-phenyl-, 4-phenyl-, and 5-phenylthiazole are reported. The vibrational force fields of thiazole and of C6H6 are applied to the phenylthiazoles, and the calculations for the normal modes are in good agreement with the vibrational frequency data and assignments. The dihedral angles are 40° for 2-phenylthiazole and 45° for 4-phenyl- and 5-phenylthiazole. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7COA of Formula: C9H7NS).

5-Phenylthiazole (cas: 1826-13-7) 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.COA of Formula: C9H7NS

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

Novel diphenylthiazole derivatives with multi-target mechanism: Synthesis, docking study, anticancer and anti-inflammatory activities was written by Abdelazeem, Ahmed H.;El-Saadi, Mohammed T.;Said, Eman G.;Youssif, Bahaa G. M.;Omar, Hany A.;El-Moghazy, Samir M.. And the article was included in Bioorganic Chemistry in 2017.Product Details of 6318-74-7 This article mentions the following:

Over the last few decades, a growing body of studies addressed the anticancer activity of NSAIDs, particularly selective COX-2 inhibitors. However, their exact mol. mechanism is still unclear and is not fully investigated. In this regard, a novel series of compounds bearing a COXs privilege scaffold, di-Ph thiazole, was synthesized and evaluated for their anticancer activity against a panel of cancer cell lines. The most active compounds 10b, 14a,b, 16a, 17a,b and 18b were evaluated in vitro for COX-1/COX-2 inhibitory activity. These compounds were suggested to exert their anticancer activity through a multi-target mechanism based on their structural features. Thus, compounds 10b and 17b with the least IC₅₀ values in MTT assay were tested against three known anticancer targets; EGFR, BRAF and tubulin. Compounds 10b and 17b showed remarkable activity against EGFR with IC₅₀ values of 0.4 and 0.2 μM, resp. and good activity against BRAF with IC₅₀ values of 1.3 and 1.7 μM, resp. In contrast, they showed weak activity in tubulin polymerization assay. The in vivo anti-inflammatory potential was assessed and interestingly, compound 17b was the most potent compound Together, this study offers some important insights into the correlation between COXs inhibition and cancer treatment. Addnl., the results demonstrated the promising activity of these compounds with a multi-target mechanism as good candidates for further development into potential anticancer agents. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Product Details of 6318-74-7).

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. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Product Details of 6318-74-7

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

The Significance of Chirality in Drug Design and Synthesis of Bitopic Ligands as D₃ Receptor (D₃R) Selective Agonists was written by Battiti, Francisco O.;Cemaj, Sophie L.;Guerrero, Adrian M.;Shaik, Anver Basha;Lam, Jenny;Rais, Rana;Slusher, Barbara S.;Deschamps, Jeffery R.;Imler, Greg H.;Newman, Amy Hauck;Bonifazi, Alessandro. And the article was included in Journal of Medicinal Chemistry in 2019.Recommanded Product: 68867-17-4 This article mentions the following:

Because of the large degree of homol. among dopamine D₂-like receptors, discovering ligands capable of discriminating between the D₂, D₃, and D₄ receptor subtypes remains a significant challenge. Previous work has exemplified the use of bitopic ligands as a powerful strategy in achieving subtype selectivity for agonists and antagonists alike. Inspired by the potential for chem. modification of the D₃ preferential agonists (+)-PD128,907 (1) and PF592,379 (2), we synthesized bitopic structures to further improve their D₃R selectivity. We found that the (2S,5S) conformation of scaffold 2 resulted in a privileged architecture with increased affinity and selectivity for the D₃R. In addition, a cyclopropyl moiety incorporated into the linker and full resolution of the chiral centers resulted in lead compound 53 and eutomer 53a that demonstrate significantly higher D₃R binding selectivities than the reference compounds Moreover, the favorable metabolic stability in rat liver microsomes supports future studies in in vivo models of dopamine system dysregulation. In the experiment, the researchers used many compounds, for example, Benzothiazole-5-carboxylic acid (cas: 68867-17-4Recommanded Product: 68867-17-4).

Benzothiazole-5-carboxylic acid (cas: 68867-17-4) 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.Recommanded Product: 68867-17-4

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