Category: thiazole

Mass spectrometry of some heterocycles was written by Dash, B.;Das, Kasturi;Dash, P. K.. And the article was included in Journal of Teaching and Research in Chemistry in 1994.Recommanded Product: 4,5-Diphenylthiazol-2-amine This article mentions the following:

The fragmentation pattern of some thiazoles and their Schiff bases, thiazolidones, oxadiazoles, thiazolopyrimidones, rhodanines, and 2-amino-3-(2-pyridylamino)benzofuran have been described. Apart from determining the mol. weights, the mass spectral fragmentations have been used in assigning the structure of the compounds Some important rearrangements have been discussed. The mass spectra of some Schiff base metal complexes in which ion decomposition is markedly dependent on the oxidation states normally assumed by the metals have also been discussed. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Recommanded Product: 4,5-Diphenylthiazol-2-amine).

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. 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: 4,5-Diphenylthiazol-2-amine

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

Potent N-(1,3-Thiazol-2-yl)pyridin-2-amine Vascular Endothelial Growth Factor Receptor Tyrosine Kinase Inhibitors with Excellent Pharmacokinetics and Low Affinity for the hERG Ion Channel was written by Bilodeau, Mark T.;Balitza, Adrienne E.;Koester, Timothy J.;Manley, Peter J.;Rodman, Leonard D.;Buser-Doepner, Carolyn;Coll, Kathleen E.;Fernandes, Christine;Gibbs, Jackson B.;Heimbrook, David C.;Huckle, William R.;Kohl, Nancy;Lynch, Joseph J.;Mao, Xianzhi;McFall, Rosemary C.;McLoughlin, Debra;Miller-Stein, Cynthia M.;Rickert, Keith W.;Sepp-Lorenzino, Laura;Shipman, Jennifer M.;Subramanian, Raju;Thomas, Kenneth A.;Wong, Bradley K.;Yu, Sean;Hartman, George D.. And the article was included in Journal of Medicinal Chemistry in 2004.Formula: C9H6ClNS This article mentions the following:

A series of N-(1,3-thiazol-2-yl)pyridin-2-amine KDR kinase inhibitors have been developed that possess optimal properties. Compounds have been discovered that exhibit excellent in vivo potency. The particular challenges of overcoming hERG binding activity and QTc increases in vivo in addition to achieving good pharmacokinetics have been accomplished by discovering a unique class of amine substituents. These compounds have a favorable kinase selectivity profile that can be accentuated with appropriate substitution. In the experiment, the researchers used many compounds, for example, 2-Chloro-5-phenylthiazole (cas: 329794-40-3Formula: C9H6ClNS).

2-Chloro-5-phenylthiazole (cas: 329794-40-3) 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.Formula: C9H6ClNS

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

Decarbonylative C-H coupling of azoles and aryl esters: Unprecedented nickel catalysis and application to the synthesis of Muscoride A was written by Amaike, Kazuma;Muto, Kei;Yamaguchi, Junichiro;Itami, Kenichiro. And the article was included in Journal of the American Chemical Society in 2012.Computed Properties of C9H7NS This article mentions the following:

A nickel-catalyzed decarbonylative C-H biaryl coupling of azoles and aryl esters is described. The newly developed catalytic system does not require the use of expensive metal catalysts or silver- or copper-based stoichiometric oxidants. We have successfully applied this new C-H arylation reaction to a convergent formal synthesis of muscoride A. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Computed Properties of C9H7NS).

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. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Computed Properties of C9H7NS

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

Copper-catalyzed tandem reactions of 2-halobenzenamines with isothiocyanates under ligand- and base-free conditions was written by Guo, Yan-Jin;Tang, Ri-Yuan;Zhong, Ping;Li, Jin-Heng. And the article was included in Tetrahedron Letters in 2010.Reference of 1843-21-6 This article mentions the following:

A ligand-free copper-catalyzed reaction of 2-halobenzenamines with isothiocyanates has been developed for the synthesis of 2-aminobenzothiazoles. In the presence of CuBr and TBAB (tetra-Bu ammonium bromide, additive), a variety of 2-halobenzenamines underwent the reaction with isothiocyanates at 40 °C, affording 2-aminobenzothiazoles, e.g., I (R¹ = H, MeO, Cl, NO₂; R² = H, Me, Cl, F), in moderate to excellent yields. It is noteworthy that the reaction is conducted under mild, relatively low catalyst loading, and ligand- and base-free conditions. 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. 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.Reference of 1843-21-6

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

Design, synthesis and characterization of novel N-heterocyclic-1-benzyl-1H-benzo[d]imidazole-2-amines as selective TRPC5 inhibitors leading to the identification of the selective compound, AC1903 was written by Sharma, Swagat H.;Pablo, Juan Lorenzo;Montesinos, Monica Suarez;Greka, Anna;Hopkins, Corey R.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2019.Synthetic Route of C4H6N2S This article mentions the following:

The transient receptor potential cation channel 5 (TRPC5) has been previously shown to affect podocyte survival in the kidney. As such, inhibitors of TRPC5 are interesting candidates for the treatment of chronic kidney disease (CKD). Herein, we report the synthesis and biol. characterization of a series of N-heterocyclic-1-benzyl-1H-benzo[d]imidazole-2-amines as selective TRPC5 inhibitors. Work reported here evaluates the benzimidazole scaffold and substituents resulting in the discovery of I, a TRPC5 inhibitor that is active in multiple animal models of CKD. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Synthetic Route of C4H6N2S).

Thiazol-2-ylmethanamine (cas: 55661-33-1) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). 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.Synthetic Route of C4H6N2S

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

Synthesis and properties of novel Y-shaped NLO molecules containing thiazole and imidazole chromophores was written by Ren, Jun;Wang, Shi-Min;Wu, Li-Fang;Xu, Zu-Xun;Dong, Bing-Hai. And the article was included in Dyes and Pigments in 2008.Application of 6318-74-7 This article mentions the following:

Two new second-order NLO mols., derived from a five-membered heterocyclic ring (thiazole and imidazole), were synthesized. The thermal stability, optical transparency and second-order nonlinear optical (NLO) properties were investigated. As a result, good nonlinearity-transparency-thermal stability trade-off was achieved. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Application of 6318-74-7).

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

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

A new asymmetric synthesis of (S)-dolaphenine and its heteroaromatic congeners utilizing (+)-2-hydroxy-3-pinanone and (-)-3-hydroxy-2-caranone as chiral auxiliaries was written by Irako, Naoko;Hamada, Yasumasa;Shioiri, Takayuki. And the article was included in Tetrahedron in 1995.Reference of 55661-33-1 This article mentions the following:

(+)-2-Hydroxy-3-pinanone and (-)-3-hydroxy-2-caranone were resp. converted to the corresponding Schiff bases derived from 2-thiazolemethanamine, 2-thiophenemethanamine, 2-furanmethanamine and benzyl amine. Alkylation of the Schiff base derivative of 2-thiazolemethanamine followed by removal of the chiral auxiliaries (+)-2-hydroxy-3-pinanone and (-)-3-hydroxy-2-caranone afforded (S)-α-(phenylmethyl)-2-thiazolemethanamine [i.e., (S)-dolaphenine] in optically pure form. The method was applied to the asym. synthesis of the dolaphenine analogs also. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Reference of 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.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Reference of 55661-33-1

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

Identification and SAR of selective inducible nitric oxide synthase (iNOS) dimerization inhibitors was written by Gahman, Timothy C.;Herbert, Mark R.;Lang, Henk;Thayer, Angie;Symons, Kent T.;Nguyen, Phan Manh;Massari, Mark E.;Dozier, Sara;Zhang, Yan;Sablad, Marciano;Rao, Tadimeti S.;Noble, Stewart A.;Shiau, Andrew K.;Hassig, Christian A.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2011.Safety of Thiazol-2-ylmethanamine This article mentions the following:

A series of imidazole containing thiadiazoles and pyrimidines has been designed and synthesized as dimerization inhibitors of inducible nitric oxide synthase (iNOS). The necessity of key imidazole and piperonyl functionality was demonstrated, and SAR studies led to the identification of compound I, which showed a dose dependent inhibition in multiple pain models, including tactile allodynia induced by spinal nerve ligation (Chung model). In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Safety of Thiazol-2-ylmethanamine).

Thiazol-2-ylmethanamine (cas: 55661-33-1) 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. 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.Safety of Thiazol-2-ylmethanamine

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

Synthesis and Carbonic Anhydrase Inhibition of Novel 2-(4-(Aryl)thiazole-2-yl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione Derivatives was written by Kocyigit, Umit M.;Aslan, Osman Nuri;Gulcin, Ilhami;Temel, Yusuf;Ceylan, Mustafa. And the article was included in Archiv der Pharmazie (Weinheim, Germany) in 2016.Reference of 6318-74-7 This article mentions the following:

A number of 2-(4-(aryl)thiazole-2-yl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione derivatives were synthesized and evaluated for their inhibitory characteristics against the human CA isoenzymes I and II (hCA I and hCA II). The structures of the new isoindolylthiazole derivatives were confirmed by means of IR, ¹H NMR, ¹³C NMR, and elemental anal. These compounds exhibited excellent inhibitory effects, in the low nanomolar range, with K_i values in the range of 27.07-37.80 nM against hCA I and in the range of 11.80-25.81 nM against hCA II. Our findings suggested that the new isoindolylthiazole derivatives have superior inhibitory effect over acetazolamide (AZA), which was used as clin. CA inhibitor with K_i values of 34.50 and 28.93 nM against the hCA I and hCA II isoenzymes, resp. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Reference of 6318-74-7).

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

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

Design, synthesis, and biological evaluation of novel dipeptide-type SARS-CoV 3CL protease inhibitors: Structure-activity relationship study was written by Thanigaimalai, Pillaiyar;Konno, Sho;Yamamoto, Takehito;Koiwai, Yuji;Taguchi, Akihiro;Takayama, Kentaro;Yakushiji, Fumika;Akaji, Kenichi;Kiso, Yoshiaki;Kawasaki, Yuko;Chen, Shen-En;Naser-Tavakolian, Aurash;Schon, Arne;Freire, Ernesto;Hayashi, Yoshio. And the article was included in European Journal of Medicinal Chemistry in 2013.Application of 1826-13-7 This article mentions the following:

This work describes the design, synthesis, and evaluation of low-mol. weight peptidic SARS-CoV 3CL protease inhibitors. The inhibitors were designed based on the potent tripeptidic Z-Val-Leu-Ala(pyrrolidone-3-yl)-2-benzothiazole (I) (K_i = 4.1 nM), in which the P3 valine unit was substituted with a variety of distinct moieties. The resulting series of dipeptide-type inhibitors displayed moderate to good inhibitory activities against 3CL^pro. In particular, compounds (II) (R¹ = OMe, R² = H and R¹ = H, R² = OMe) exhibited good inhibitory activities with K_i values of 0.39 and 0.33 μM, resp. These low-mol. weight compounds are attractive leads for the further development of potent peptidomimetic inhibitors with pharmaceutical profiles. Docking studies were performed to model the binding interaction of the compound II (R¹ = OMe, R² = H) with the SARS-CoV 3CL protease. The preliminary SAR study of the peptidomimetic compounds with potent inhibitory activities revealed several structural features that boosted the inhibitory activity: (i) a benzothiazole warhead at the S1′ position, (ii) a γ-lactam unit at the S1-position, (iii) an appropriately hydrophobic leucine moiety at the S2-position, and (iv) a hydrogen bond between the N-arylglycine unit and a backbone hydrogen bond donor at the S3-position. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Application of 1826-13-7).

5-Phenylthiazole (cas: 1826-13-7) 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 of 1826-13-7

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