Heterocyclic Building Blocks-Thiazole

Straightforward synthesis of 2-anilinobenzoxazoles and -benzothiazoles via mechanochemical ball-milling-promoted one-pot reactions was written by Zhang, Ze;Wang, Fang-Jian;Wu, Hao-Hao;Tan, Ya-Jun. And the article was included in Chemistry Letters in 2015.Related Products of 1843-21-6 This article mentions the following:

Under mechanochem. ball-milling and solvent-free conditions, a series of 2-anilinobenzoxazoles and 2-anilinobenzothiazoles were synthesized directly from the one-pot reaction of anilines, CS₂, and 2-aminophenol and -thiophenol. This protocol exhibited the free or cheap use of a cyclodesulfurization reagent, no separation of in-situ generated isothiocyanate, short reaction time and simple work-up procedure. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Related Products of 1843-21-6).

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. 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 1843-21-6

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

Quinazolone derivatives was written by Dash, B.;Mahapatra, Prasanta K.;Mahapatra, Prasanna K.. And the article was included in Journal of the Institution of Chemists (India) in 1983.HPLC of Formula: 6318-74-7 This article mentions the following:

Thiazolylquinazolones I [R = Me, Ph; R¹ = thienyl, (un)substituted Ph; R² = H, Ph, 2-Cl₆H₄, 4-ClC₆H₄] were prepared by aminolysis of benzoxazinones II with thiazolylamines III. Arylidenequinazolones I [R = R³C₆H₄CH:CH; R¹ = (un)substituted Ph; R² = H, Ph, 2-ClC₆H₄, 4-ClC₆H₄; R³ = 2-Cl, 4-Cl] were prepared by condensing I (R = Me) with R³C₆H₄CHO. At 500 ppm I inhibited Helminthosporium sativum by 50-70%, in vitro. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7HPLC of Formula: 6318-74-7).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) 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. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.HPLC of Formula: 6318-74-7

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

Reengineered tricyclic anti-cancer agents was written by Kastrinsky, David B.;Sangodkar, Jaya;Zaware, Nilesh;McClinch, Kimberly;Farrington, Caroline C.;Giannini, Heather M.;Izadmehr, Sudeh;Dhawan, Neil S.;Narla, Goutham;Ohlmeyer, Michael. And the article was included in Bioorganic & Medicinal Chemistry in 2015.Electric Literature of C6H7ClN2O3S2 This article mentions the following:

The phenothiazine and dibenzazepine tricyclics are potent neurotropic drugs with a documented but underutilized anti-cancer side effect. Reengineering these agents (TFP, CPZ, CIP) by replacing the basic amine with a neutral polar functional group (e.g., RTC-1, RTC-2) abrogated their CNS effects as demonstrated by in vitro pharmacol. assays and in vivo behavioral models. Further optimization generated several phenothiazines and dibenzazepines with improved anti-cancer potency, exemplified by RTC-5. This new lead demonstrated efficacy against a xenograft model of an EGFR driven cancer without the neurotropic effects exhibited by the parent mols. Its effects were attributed to concomitant neg. regulation of PI3K-AKT and RAS-ERK signaling. 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. 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.Electric Literature of C6H7ClN2O3S2

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

Design, synthesis, structure-activity relationship, and in vivo activity of azabicyclic aryl amides as α7 nicotinic acetylcholine receptor agonists was written by Walker, Daniel P.;Wishka, Donn G.;Piotrowski, David W.;Jia, Shaojuan;Reitz, Steven C.;Yates, Karen M.;Myers, Jason K.;Vetman, Tatiana N.;Margolis, Brandon J.;Jacobsen, E. Jon;Acker, Brad A.;Groppi, Vincent E.;Wolfe, Mark L.;Thornburgh, Bruce A.;Tinholt, Paula M.;Cortes-Burgos, Luz A.;Walters, Rodney R.;Hester, Matthew R.;Seest, Eric P.;Dolak, Lester A.;Han, Fusen;Olson, Barbara A.;Fitzgerald, Laura;Staton, Brian A.;Raub, Thomas J.;Hajos, Mihaly;Hoffmann, William E.;Li, Kai S.;Higdon, Nicole R.;Wall, Theron M.;Hurst, Raymond S.;Wong, Erik H. F.;Rogers, Bruce N.. And the article was included in Bioorganic & Medicinal Chemistry in 2006.Safety of Benzothiazole-5-carboxylic acid This article mentions the following:

A novel set of azabicyclic aryl amides have been identified as potent and selective agonists of the α7 nAChR. A two-pronged approach was taken to improve the potential hERG liability of previously disclosed α7 nAChR agonist, PNU-282,987, while maintaining the compound’s other desirable pharmacol. properties. The first approach involved further exploration of the aryl carboxylic acid fragment of PNU-282,987, while the second approach focused on modification of the azabicyclic amine portion of PNU-282,987. The best compounds from each series are characterized by rapid brain penetration, good oral bioavailability in rat, and demonstrate in vivo efficacy in a rat P50 auditory sensory gating assay. At least one analog from each series shows an improved hERG safety profile over PNU-282,987. In the experiment, the researchers used many compounds, for example, Benzothiazole-5-carboxylic acid (cas: 68867-17-4Safety of Benzothiazole-5-carboxylic acid).

Benzothiazole-5-carboxylic acid (cas: 68867-17-4) 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. For example, 2,4-dimethylthiazole is synthesized from thioacetamide and chloroacetone.Safety of Benzothiazole-5-carboxylic acid

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

A copper-mediated cross-coupling approach for the synthesis of 3-heteroaryl quinolone and related analogues was written by Shin, Sanghye;Kim, Yechan;Kim, Kiho;Hong, Sungwoo. And the article was included in Organic & Biomolecular Chemistry in 2014.Related Products of 1826-13-7 This article mentions the following:

An efficient and practical method for the direct cross-coupling between quinolones and a range of azoles was developed via copper-mediated C-H functionalization. This synthetic strategy provides a convenient access to a variety of C3-heteroaryl quinolones, quinolinone, nalidixic acid, uracil, pyridone, and chromone derivatives, which are prominent structural motifs in many biol. active compounds E.g., in presence of CuI and LiOCMe₃ in 1,4-dioxane under N₂ at 110 °C, coupling of 1-benzyl-3-iodo-4-quinolone with benzothiazole gave 80% 3-heteroaryl quinolone derivative (I). In the experiment, the researchers used many compounds, for example, 5-Phenylthiazole (cas: 1826-13-7Related Products 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 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.Related Products of 1826-13-7

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

Discovery of N-(4-aryl-5-aryloxy-thiazol-2-yl)-amides as potent RORγt inverse agonists was written by Wang, Yonghui;Yang, Ting;Liu, Qian;Ma, Yingli;Yang, Liuqing;Zhou, Ling;Xiang, Zhijun;Cheng, Ziqiang;Lu, Sijie;Orband-Miller, Lisa A.;Zhang, Wei;Wu, Qianqian;Zhang, Kathleen;Li, Yi;Xiang, Jia-Ning;Elliott, John D.;Leung, Stewart;Ren, Feng;Lin, Xichen. And the article was included in Bioorganic & Medicinal Chemistry in 2015.Formula: C15H12N2S This article mentions the following:

A novel series of N-(4-aryl-5-aryloxy-thiazol-2-yl)-amides as RORγt inverse agonists was discovered. Binding mode anal. of a RORγt partial agonist (2c) revealed by co-crystal structure in RORγt LBD suggests that the inverse agonists do not directly interfere with the interaction between H12 and the RORγt LBD. Detailed SAR exploration led to identification of potent RORγt inverse agonists such as 3m with a pIC₅₀ of 8.0. Selected compounds in the series showed reasonable activity in Th17 cell differentiation assay as well as low intrinsic clearance in mouse liver microsomes. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Formula: C15H12N2S).

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. 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.Formula: C15H12N2S

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

Chiral Pentacarboxycyclopentadiene-Based Bronsted Acid-Catalyzed Enantioselective Desymmetrization of Meso-Epoxides by 2-Mercaptobenzothiazoles was written by Yuan, Chao;Li, Jun;Li, Pingfan. And the article was included in ACS Omega in 2018.HPLC of Formula: 58759-63-0 This article mentions the following:

Enantioselective desymmetrization of meso-epoxides by 2-mercaptobenzothiazoles was realized by using the pentacarboxycyclopentadiene-based chiral Bronsted acid in combination of N-isopropylaniline as amine additive to give up to 90.5:9.5 er of the ring opening products. In the experiment, the researchers used many compounds, for example, 5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0HPLC of Formula: 58759-63-0).

5-Nitrobenzothiazole-2-thiol (cas: 58759-63-0) 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.HPLC of Formula: 58759-63-0

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

Organic base-catalyzed C-S bond construction from CO₂: a new route for the synthesis of benzothiazolones was written by Gao, Xiang;Deng, Yuehua;Lu, Changyu;Zhang, Lei;Wang, Xintao;Yu, Bo. And the article was included in Catalysts in 2018.Related Products of 62266-81-3 This article mentions the following:

Herein, a novel green method of synthesizing benzothiazolones such as I [R = H, 6-Me, 6-OMe, 6-Cl, 6-Br] via cyclocarbonylation of 2-aminothiophenols with CO₂ was developed. A series of organic bases was investigated for the catalysis of cyclocarbonylation, among which 1,5-diazabicyclo[4.3.0]non-5-ene displayed the best catalytic activity. Then, various reaction parameters such as CO₂ pressure, temperature, amount of catalyst and reaction time for the catalytic performance were studied. In the experiment, the researchers used many compounds, for example, 6-Chlorobenzo[d]thiazol-2(3H)-one (cas: 62266-81-3Related Products of 62266-81-3).

6-Chlorobenzo[d]thiazol-2(3H)-one (cas: 62266-81-3) 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. Prominent is the Hantzsch thiazole synthesis is a reaction between haloketones and thioamides.Related Products of 62266-81-3

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

A novel route to 4-aryl-5,6-dihydro-1,2-oxathiin-2,2-dioxides and related heterocyclic systems was written by Bonfand, Eric;Motherwell, William B.;Pennell, Andrew M. K.;Uddin, Muhammed K.;Ujjainwalla, Feroze. And the article was included in Heterocycles in 1997.Recommanded Product: 69812-29-9 This article mentions the following:

The addition of a tributylstannyl radical to arene and heteroarene sulfonate esters of homopropargyl alcs. triggers a sequence of [1,6] ipso-substitution followed by 6-endo addition and elimination to yield unusual 4-aryl-5,6-dihydro-1,2-oxathiin-2,2-dioxides and related heterocyclic systems. E.g., addition of AIBN and Bu₃SnH to 4-MeC₆H₄SO₂NMeCH₂CH₂CCH gave 15% 1,2-thiazine-S,S-dioxide I and 8% 4-MeC₆H₄C(:CH₂)CH₂CH₂NHMe. In the experiment, the researchers used many compounds, for example, 2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9Recommanded Product: 69812-29-9).

2-Acetamido-4-methylthiazole-5-sulfonyl chloride (cas: 69812-29-9) 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. 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.Recommanded Product: 69812-29-9

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

Synthesis of some thiazole Schiff bases and their derivatives was written by Dash, B.;Patra, M.;Mohapatra, P. K.. And the article was included in Journal of the Indian Chemical Society in 1985.Category: thiazole This article mentions the following:

Twenty-six thiazole Schiff bases I [R¹, R² = (un)substituted Ph; R³ = (un)substituted Ph, 2-hydroxynaphthyl] were prepared in 58-78% yield by refluxing a mist. of the appropriate aminothiazole and aldehyde in EtOH in the presence of piperidine. Cycloaddition of the Schiff bases with thioglycolic acid in C₆H₆ at reflux gave the thiazolidinones II in 65-77% yield (17 compounds). Reaction of I with cyclohexanone in EtOH at reflux in the presence of HCl gave the [(oxocyclohexy)methyl]amino derivatives III in 58-76% yields (13 compounds). All the compound prepared showed antifungal activity against Curvularia species. In the experiment, the researchers used many compounds, for example, 4,5-Diphenylthiazol-2-amine (cas: 6318-74-7Category: thiazole).

4,5-Diphenylthiazol-2-amine (cas: 6318-74-7) belongs to thiazole derivatives. Thiazoles are a class of five-membered rings containing nitrogen and sulfur with excellent antitumor, antiviral and antibiotic activities. 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.Category: thiazole

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