Category: thiazole

Synthesis of thiazolylquinazolin-4(3H)-ones was written by Badr, M. Z. A.;El-Sherief, H. A. H.;El-Naggar, G. M.;Mahmoud, A. M.. And the article was included in Indian Journal of Chemistry in 1979.Application of 6318-74-7 This article mentions the following:

3-Thiazolylquinazol-4-ones I (R = Me, Ph; R¹ = H, CO₂Et; R² = Ph, 4-MeC₆H₄, 4-MeOC₆H₄, 4-ClC₆H₄, 4-BrC₆H₄, Me) were prepared by condensing 3,1-benzoxazin-4(H)-ones II with aminothiazoles III. Heating 2-aroylaminothiazoles IV in dry pyridine also give I. 2-Styrylquinazol-4-ones I (R = 4-O₂NC₆H₄CH:CH, R¹ = H, Ph, CO₂Et, R² = Ph, Me, 4-MeC₆H₄; R = 4-ClC₆H₄CH:CH, R¹ = R² = Ph) were prepared by condensing aromatic aldehydes with I (R = Me). I and IV showed bactericidal activity. 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. 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 6318-74-7

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

Non-peptidic small molecule inhibitors of XIAP was written by Park, Cheol-Min;Sun, Chaohong;Olejniczak, Edward T.;Wilson, Alan E.;Meadows, Robert P.;Betz, Stephen F.;Elmore, Steven W.;Fesik, Stephen W.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2005.Recommanded Product: 6318-74-7 This article mentions the following:

Non-peptidic small mol. SMAC mimetics were designed and synthesized that bind to the BIR3 domain of XIAP using structure-based design. Substituted five-membered heterocycles such as thiazoles and imidazoles were identified that serve as replacements for peptide fragments of the lead. An example compound thus prepared and evaluated was an N-(thiazolyl)-L-alaninamide derivative (I). In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Recommanded Product: 6318-74-7).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) 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.Various laboratory methods exist for the organic synthesis of thiazoles. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Recommanded Product: 6318-74-7

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

Amphiphilic π-Allyliridium C,O-Benzoates Enable Regio- and Enantioselective Amination of Branched Allylic Acetates Bearing Linear Alkyl Groups was written by Meza, Arismel Tena;Wurm, Thomas;Smith, Lewis;Kim, Seung Wook;Zbieg, Jason R.;Stivala, Craig E.;Krische, Michael J.. And the article was included in Journal of the American Chemical Society in 2018.Safety of Thiazol-2-ylmethanamine This article mentions the following:

The first examples of amphiphilic reactivity in the context of enantioselective catalysis are described. Com. available π-allyliridium C,O-benzoates, which are stable to air, water and SiO₂ chromatog., and are well-known to catalyze allyl acetate-mediated carbonyl allylation, are now shown to catalyze highly chemo-, regio- and enantioselective substitutions of branched allylic acetates bearing linear alkyl groups with primary amines. 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. 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. 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.Safety of Thiazol-2-ylmethanamine

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

Development of Glucose Regulated Protein 94-Selective Inhibitors Based on the BnIm and Radamide Scaffold was written by Crowley, Vincent M.;Khandelwal, Anuj;Mishra, Sanket;Stothert, Andrew R.;Huard, Dustin J. E.;Zhao, Jinbo;Muth, Aaron;Duerfeldt, Adam S.;Kizziah, James L.;Lieberman, Raquel L.;Dickey, Chad A.;Blagg, Brian S. J.. And the article was included in Journal of Medicinal Chemistry in 2016.Related Products of 55661-33-1 This article mentions the following:

(Arylmethyl)imidazolylethyl chlorodihydroxybenzoates I (R = Ph, 4-FC₆H₄, 4-ClC₆H₄, 4-BrC₆H₄, 4-IC₆H₄, 4-MeC₆H₄, 4-EtC₆H₄, 4-i-PrC₆H₄, 4-NCC₆H₄, 4-HCCC₆H₄, 4-F₃CC₆H₄, 4-PhC₆H₄, 4-MeOC₆H₄, 3,4-Cl₂C₆H₃, 1-naphthyl, 2-naphthyl, 5-quinolinyl, 3-FC₆H₄, 3-ClC₆H₄, 3-BrC₆H₄, 3-IC₆H₄, 3-MeOC₆H₄, 3-MeC₆H₄, 3-PhC₆H₄, 2-FC₆H₄, 2-ClC₆H₄, 2-BrC₆H₄, 2-MeC₆H₄, 2-H₂NC₆H₄, 2-MeOC₆H₄, 2-EtC₆H₄, 2-EtOC₆H₄, 2-i-PrOC₆H₄, 2-n-PrOC₆H₄, 2-F₃CC₆H₄, 2-MeO-4-MeC₆H₃, 3-furanyl, 2-furanyl, 5-Me-2-furanyl, 5-Cl-2-furanyl, 3,5-dimethyl-2-furanyl, 2-thienyl, 3-thienyl, 5-Me-2-thienyl, 5-Cl-2-thienyl, 4-Cl-2-thienyl, 3-Cl-2-thienyl, 5-isoxazolyl, 2-thiazolyl, 3-vinyl-2-thienyl, 3-vinyl-2-furanyl, 3-Et-2-thienyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 5-pyrimidinyl) were prepared as selective inhibitors of glucose regulated protein 94 (Grp94), the endoplasmic reticulum-resident isoform of the heat shock protein 90 (Hsp90), for potential use in the treatment of glaucoma and cancer; the effect of the aryl substituents on Grp94 binding and selectivity was determined I were prepared by the cyclocondensation of a bissilylated chloro(oxopropyl)dihydroxybenzoate with glyoxal and arylmethylamines RCH₂NH₂ (R = Ph, 4-FC₆H₄, 4-ClC₆H₄, 4-BrC₆H₄, 4-IC₆H₄, 4-MeC₆H₄, 4-EtC₆H₄, 4-i-PrC₆H₄, 4-NCC₆H₄, 4-HCCC₆H₄, 4-F₃CC₆H₄, 4-PhC₆H₄, 4-MeOC₆H₄, 3,4-Cl₂C₆H₃, 1-naphthyl, 2-naphthyl, 5-quinolinyl, 3-FC₆H₄, 3-ClC₆H₄, 3-BrC₆H₄, 3-IC₆H₄, 3-MeOC₆H₄, 3-MeC₆H₄, 3-PhC₆H₄, 2-FC₆H₄, 2-ClC₆H₄, 2-BrC₆H₄, 2-MeC₆H₄, 2-H₂NC₆H₄, 2-MeOC₆H₄, 2-EtC₆H₄, 2-EtOC₆H₄, 2-i-PrOC₆H₄, 2-n-PrOC₆H₄, 2-F₃CC₆H₄, 2-MeO-4-MeC₆H₃, 3-furanyl, 2-furanyl, 5-Me-2-furanyl, 5-Cl-2-furanyl, 3,5-dimethyl-2-furanyl, 2-thienyl, 3-thienyl, 5-Me-2-thienyl, 5-Cl-2-thienyl, 4-Cl-2-thienyl, 3-Cl-2-thienyl, 5-isoxazolyl, 2-thiazolyl, 3-vinyl-2-thienyl, 3-vinyl-2-furanyl, 3-Et-2-thienyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 5-pyrimidinyl) followed by desilylation. I (R = 2-MeO-4-MeC₆H₃CH₂, 5-chloro-2-furanylmethyl) were tested as inhibitors of cell migration in a cancer metastasis model and for their enhancement of the degradation of mutants of the protein myocilin in a glaucoma model. The structures of the lead compound radamide bound to Hsp82 and Grp94 and of I (R = 5-chloro-2-furanyl) bound to the N-terminal domain of Hsp94 lacking its acidic linker were determined by X-ray crystallog. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Related Products of 55661-33-1).

Thiazol-2-ylmethanamine (cas: 55661-33-1) belongs to thiazole derivatives. The thiazole ring is notable as a component of the vitamin thiamine (B1). Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Related Products of 55661-33-1

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

Synthesis and SAR study of novel 7-(pyridinium-3-yl)-carbonyl imidazo[5,1-b]thiazol-2-yl carbapenems was written by Maruyama, Takahisa;Kano, Yuko;Yamamoto, Yasuo;Kurazono, Mizuyo;Iwamatsu, Katsuyoshi;Atsumi, Kunio;Shitara, Eiki. And the article was included in Bioorganic & Medicinal Chemistry in 2007.Related Products of 55661-33-1 This article mentions the following:

A new series of 1β-Me carbapenems, possessing a 7-substituted imidazo[5,1-b]thiazol-2-yl group directly attached to the C-2 position of the carbapenem nucleus, was synthesized and evaluated for antibacterial activity. These compounds showed potent activities against Gram-pos. bacteria, in particular methicillin-resistant Staphylococcus aureus (MRSA) and penicillin-resistant Streptococcus pneumoniae (PRSP). They also exhibited potent activity against β-lactamase-neg. ampicillin-resistant Haemophilus influenzae (BLNAR). In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Related Products of 55661-33-1).

Thiazol-2-ylmethanamine (cas: 55661-33-1) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. 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.Related Products of 55661-33-1

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

radicAl rEactivity in thiazoles. i. comparison of the reactivity of thiazole, mono- and dialkylthiazoles and mono- and diphenylthiazoles in was written by Vernin, Gaston;Dou, Henri J. M.;Metzger, Jacques. And the article was included in Bulletin de la Societe Chimique de France in 1967.SDS of cas: 1826-13-7 This article mentions the following:

The radical reactivity in thiazoles (I) was studied by examining the products formed by the decomposition of Bz2O2 in I. Thus, thiazole (85 g.) was treated with 10 g. Bz2O2 20 hrs. at 78°, according to method described by G. Vernin and J. Metzger (1963), to give the following compounds: CO2 0.5, BzOH and phenylbenzoic acid 7, basic fractions (containing phenylthiazoles 80, dithiazolyls 15, and others 5%) 1, and resins 1 g. 4-Methylthiazole and 2,4-dimethylthiazole were treated similarly and showed an increase in the formation of secondary products due to the dimerization of thiazolyl methylene radical produced. The determination of I isomers in the basic fraction at position 2, 4, and 5 was carried out by gas chromatog. using 5% diethylene glycol succinate at 200° or by Al2O3 column using C6H6 as eluant. Column chromatog. gave 4 sep. fractions: the 1st was rich in 2-phenyl- and 4-phenylthiazole (II); the 2nd contained 2,2′- and 2,5′-dithiazolyls; the 3rd contained 5-phenylthiazole (III); and the 4th (eluted by 10% MeOH in C6H6) contained polythiazolyls, polyphenylthiazoles, and hydroxythiazoles. The 3 first fraction isomers were further separated by gas chromatog. using by 10% Carbowax 20M. The effect of temperature and Bz2O2 concentration on the % of phenylthiazole isomers was studied at 80-115° and 0.01-0.1 mole Bz2O2/mole I. The results show the highest percentages of II and III were obtained at 115-20° and 0.1 mole Bz2O2. The phenylation of I was also carried out in presence of AcOH. The results showed an increased activity of position 2 of the ring. The steric effect of substituents at the 2 and 4 position of thiazole ring on % isomers and radical reactivity was examined in acidic and neutral media. Radical phenylation of thiazole-2-d was carried in acid media. No isotopic effect was shown on % of 4- and 5- isomers. The phenylation of phenylthiazoles was carried in acidic and neutral media in the presence of 0.001 mole Bz2O2. The results showed that the decomposition of Bz2O2 in both media is the same. The following are % triphenylthiazoles obtained from 2,4-diphenylthiazole 17, 2,5-diphenylthiazole 3, and 4,5-diphenylthiazole 25%. The relative rates of arylation of I were determined by the competitive Ingold method using 5% Bz2O2 solutions and PhNO2 as a reference substrate at 120° in both acidic and neutral media. The reaction products were analyzed by gas chromatog. using Silicone SE-30 and Carbowax 20M columns. The % of nitrobiphenyls and phenylthiazoles were determined by Bartlet and Smith method (1960). The results showed the exptl. reactivity of I in phenylation reactions are in the order of -5>-2>-4 positions in the ring. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7SDS of cas: 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). 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.SDS of cas: 1826-13-7

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

Copper-Catalyzed Thiolation of Terminal Alkynes Employing Thiocyanate as the Sulfur Source Leading to Enaminone-Based Alkynyl Sulfides under Ambient Conditions was written by R., Chandran;Pise, Ashwini;Shah, Suraj Kumar;D., Rahul;V., Suman;Tiwari, Keshri Nath. And the article was included in Organic Letters in 2020.SDS of cas: 6294-52-6 This article mentions the following:

A highly efficient protocol for copper-catalyzed thio-alkynylation of enaminone-based thiocyanates with terminal alkynes under mild conditions has been developed. This scalable amino group-directed thio-alkynylation proceeds in the open air with a broad substrate scope and an excellent yield. The demonstrated synthetic transformation creates the opportunity for a wide variety of sulfur-containing useful materials. Gram-scale synthesis and further synthetic transformations of alkynyl sulfides highlight the potential utility of the method. In the experiment, the researchers used many compounds, for example, 5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6SDS of cas: 6294-52-6).

5,6-Dimethoxybenzo[d]thiazol-2-amine (cas: 6294-52-6) 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: 6294-52-6

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

[Chemical-induced polycyst with renal tumor and expression of 8-OHdG in kidney tissue]. was written by Huang, X;Wang, X;Zhu, J;Hou, S;Dong, J. And the article was included in Zhonghua wai ke za zhi [Chinese journal of surgery] in 2000.Application of 6318-74-7 This article mentions the following:

OBJECTIVE: To induce the rat model of polycyst with renal tumor and investigate the expression of 8-OHdG in the kidney tissues. METHODS: The rat model of polycyst with renal tumor, similar to human acquired cystic disease of the kidney (ACDK), was induced by oral administration of 2-amino-4, 5-diphenylthiazole (DPT) and N-nitrosomorpholine (NNM). Immunohistochemical method (LSAB) was used to assay the expression of 8-hydroxydeoxyguanosine (8-OHdG) in the rat kidney tissue. RESULTS: Three of 10 rats in the NNM group had renal solid adenomatous lesions. Bilateral polycysts were observed in all 9 rats of the DPT/NNM group. Seven of the 9 rats had cystic multistage renal tumor. In the DPT/NNM group, 4 rats had cystic adenomatous lesions, but none in the other groups showed this lesion. In the model, adenomatous lesions derived from polycysts in the rats were closely consistent to human ACDK in morphology. The significant expression of 8-OHdG was found on renal tubular cell, cystic epithelial cell, stromal cell and tumor cell in all rats of the NNM and DPT/NNM group. CONCLUSION: A rat model of polycysts with renal tumor, similar to human ACDK, induced by DPT and NNM provides evidences for further study on pathogenic mechanism in human ACDK with renal cell carcinoma. The expression of 8-OHdG, a DNA damage marker, in the renal tissues of rat model might help to explain the mechanism of cysticogenesis and carcinogenesis in human ACDK. 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 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. Various laboratory methods exist for the organic synthesis of thiazoles. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Application of 6318-74-7

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

Design and synthesis of new tripeptide-type SARS-CoV 3CL protease inhibitors containing an electrophilic arylketone moiety was written by Konno, Sho;Thanigaimalai, Pillaiyar;Yamamoto, Takehito;Nakada, Kiyohiko;Kakiuchi, Rie;Takayama, Kentaro;Yamazaki, Yuri;Yakushiji, Fumika;Akaji, Kenichi;Kiso, Yoshiaki;Kawasaki, Yuko;Chen, Shen-En;Freire, Ernesto;Hayashi, Yoshio. And the article was included in Bioorganic & Medicinal Chemistry in 2013.Name: 5-Phenylthiazole This article mentions the following:

We describe here the design, synthesis and biol. evaluation of a series of mols. toward the development of novel peptidomimetic inhibitors of SARS-CoV 3CL^pro. A docking study involving binding between the initial lead compound (I) and the SARS-CoV 3CL^pro motivated the replacement of a thiazole with a benzothiazole unit as a warhead moiety at the P1′ site. This modification led to the identification of more potent derivatives, including (II) (R¹ = R₂ = H; R¹ = OMe, R² = H; R¹ = H, R² = OMe; R¹ = NMe₂, H² = H; R¹ = H, R² = NMe2), with IC₅₀ or K_i values in the submicromolar to nanomolar range. In particular, compounds II (R¹ = R² = H; R¹ = H, R² = NMe₂) exhibited the most potent inhibitory activities, with K_i values of 4.1 and 3.1 nM, resp. The peptidomimetic compounds identified through this process are attractive leads for the development of potential therapeutic agents against SARS. The structural requirements of the peptidomimetics with potent inhibitory activities against SARS-CoV 3CL^pro may be summarized as follows: (i) the presence of a benzothiazole warhead at the S1′-position; (ii) hydrogen bonding capabilities at the cyclic lactam of the S1-site; (iii) appropriate stereochem. and hydrophobic moiety size at the S2-site and (iv) a unique folding conformation assumed by the phenoxyacetyl moiety at the S4-site. In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Name: 5-Phenylthiazole).

5-Phenylthiazole (cas: 1826-13-7) 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. 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.Name: 5-Phenylthiazole

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

Use of molecular oxygen as a reoxidant in the synthesis of 2-substituted benzothiazoles via palladium-catalyzed C-H functionalization/intramolecular C-S bond formation was written by Inamoto, Kiyofumi;Hasegawa, Chisa;Kawasaki, Junpei;Hiroya, Kou;Doi, Takayuki. And the article was included in Advanced Synthesis & Catalysis in 2010.Safety of N-Phenylbenzo[d]thiazol-2-amine This article mentions the following:

Mol. oxygen (O₂) was successfully employed as a reoxidant in cyclizations of thiobenzanilides through a palladium-catalyzed C-H functionalization/intramol. C-S bond formation process, leading to an efficient, green method for the synthesis of 2-arylbenzothiazoles I (R¹ = 6-CN, 6-EtOCO, 6-NO₂, 6-MeO, 5-MeO, 4-Me, 6-Cl, 6-Br, 5-Br, 6-I, 4-F, 5-N, 6-N, R² = H; R¹ = H, R² = 4-CN, 4-Cl, 4-MeO, 3-MeO; R¹ =6-CN, R² = 4-MeO). Addition of cesium fluoride (CsF) greatly enhanced the reactions, which produced variously substituted 2-aryl-benzothiazoles with good functional group tolerance. Thioureas were also found to be suitable substrates for the cyclization process using a palladium/O₂ catalyst system, thus generating 2-aminobenzothiazoles II (R¹ = H, R² = 4-MeO-Bn, 4-NO₂-Bn, 2-Me-Bn, Ph, 1-Ph-Et, R³ = H ; R¹ = H, 6-MeO, 6-CN, 4-Me, R² = Bn, R³ = H; R¹ = H, R², R³ = morpholinyl). One-pot syntheses of 2-aminobenzothiazoles II from aryl isothiocyanates and amines were also successful. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Safety of N-Phenylbenzo[d]thiazol-2-amine).

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.Safety of N-Phenylbenzo[d]thiazol-2-amine

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