Heterocyclic Building Blocks-Thiazole

Design of Aminobenzothiazole Inhibitors of Rho Kinases 1 and 2 by Using Protein Kinase A as a Structure Surrogate was written by Judge, Russell A.;Scott, Victoria E.;Simler, Gricelda H.;Pratt, Steve D.;Namovic, Marian T.;Putman, C. Brent;Aguirre, Ana;Stoll, Vincent S.;Mamo, Mulugeta;Swann, Steven I.;Hobson, Adrian D.. And the article was included in ChemBioChem in 2018.Category: thiazole This article mentions the following:

We describe the design, synthesis, and structure-activity relationships (SARs) of a series of 2-aminobenzothiazole inhibitors of Rho kinases (ROCKs) 1 and 2, which were optimized to low nanomolar potencies by use of protein kinase A (PKA) as a structure surrogate to guide compound design. A subset of these mols. also showed robust activity in a cell-based myosin phosphatase assay and in a mech. hyperalgesia in vivo pain model. In the experiment, the researchers used many compounds, for example, 6-Bromo-2-chlorobenzothiazole (cas: 80945-86-4Category: thiazole).

6-Bromo-2-chlorobenzothiazole (cas: 80945-86-4) 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.Category: thiazole

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

CNDO/S method interpretation of ultraviolet spectra of phenylthiazoles was written by Bouscasse, L.;Lebreton, M.;Aune, J. P.. And the article was included in Spectroscopy Letters in 1994.Application of 1826-13-7 This article mentions the following:

The UV spectra of three phenylthiazoles are reported. These exptl. results are interpreted using CNDO/S method (CNDO for Spectroscopy). Calculations show that the observed transitions, except two, are pseudo π → π^* type transitions. 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. 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.Application of 1826-13-7

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

Novel 2-(4-methylsulfonylphenyl)pyrimidine derivatives as highly potent and specific COX-2 inhibitors was written by Orjales, Aurelio;Mosquera, Ramon;Lopez, Beatriz;Olivera, Roberto;Labeaga, Luis;Nunez, M. Teresa. And the article was included in Bioorganic & Medicinal Chemistry in 2008.COA of Formula: C4H6N2S This article mentions the following:

New series of 2-(4-methylsulfonylphenyl) and 2-(4-sulfamoylphenyl)pyrimidines were synthesized and evaluated for their ability to inhibit cyclooxygenase-2 (COX-2). COX-1 and COX-2 inhibitory activity of these compounds was determined using purified enzyme (PE) and human whole blood (HWB) assays. Extensive structure-activity relationship (SAR) work was carried out within these series, and a wide number of potent and specific COX-2 inhibitors were identified (HWB COX-2 IC₅₀ = 2.4-0.3 nM and 80- to 780-fold more selective than rofecoxib). In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1COA of Formula: C4H6N2S).

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. 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.COA of Formula: C4H6N2S

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

Benzimidazole-carboxamides as potent and bioavailable stearoyl-CoA desaturase (SCD1) inhibitors from ligand-based virtual screening and chemical optimization was written by Matter, Hans;Zoller, Gerhard;Herling, Andreas W.;Sanchez-Arias, Juan-Antonio;Philippo, Christophe;Namane, Claudie;Kohlmann, Markus;Pfenninger, Anja;Voss, Marc D.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2013.SDS of cas: 55661-33-1 This article mentions the following:

The discovery of potent benzimidazole stearoyl-CoA desaturase (SCD1) inhibitors by ligand-based virtual screening is described. ROCS 3D-searching gave a favorable chem. motif that was subsequently optimized to arrive at a chem. series of potent and promising SCD1 inhibitors. In particular, compound SAR224 was selected for further pharmacol. profiling based on favorable in vitro data. After oral administration to male ZDF rats, this compound significantly decreased the serum fatty acid desaturation index, thus providing conclusive evidence for SCD1 inhibition in vivo by SAR224. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1SDS of cas: 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). 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.SDS of cas: 55661-33-1

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

Diphenylthiazole-induced changes in renal ultrastructure and enzymology: toxicologic mechanisms in polycystic kidney disease? was written by Hjelle, J. T.;Hjelle, J. J.;Maziasz, T. J.;Carone, F. A.. And the article was included in Journal of Pharmacology and Experimental Therapeutics in 1987.Recommanded Product: 6318-74-7 This article mentions the following:

Renal cystic disease was chem. induced in rats by feeding 2-amino-4,5-diphenylthiazole (DPT)(I) for up to 4 wk. After 4 days of feeding, DPT had induced a 4-fold increase in total urine output relative to diet-restricted control groups. Both groups maintained, but did not gain, weight during the feeding schedule. Cyst formation was localized to the medullary collecting tubules. Relative to diet-restricted controls, rats fed DPT exhibited diminished renal and hepatic catalase activity, but elevated activity for UDP-glucuronosyltransferase. Medulla showed an increase in the specific activities of the enzymes galactosyltransferase and sulfatase B. These enzymol. findings correlated with ultrastructural observations of a loss of peroxisomes, proliferation of endoplasmic reticulum, and enlargement of the Golgi apparatus Serum and urinary levels of inorganic sulfate were significantly increased in DPT-fed rats relative to controls. Tissue levels of UDP-glucuronic acid and adenosine 3′-phosphate 5′-phosphosulfate were not depressed by DPT feeding. Thus, DPT-induced cyst formation and loss of staining for glycosaminoglycans does not involve gross depletions of UDP-glucuronic acid and adenosine 3′-phosphate 5′-phosphosulfate, mutual cosubstrates for Phase II drug conjugation reactions, and glycosaminoglycan synthesis. 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 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: 6318-74-7

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

Schiff bases in heterocyclic synthesis: synthesis of some new heterocycles of pharmaceutical interest was written by El-Ablak, F. Z.;Etman, H. A.;Metwally, M. A.. And the article was included in Zhonghua Yaoxue Zazhi in 1993.Reference of 6318-74-7 This article mentions the following:

Treating aminothiazoles I (R¹ = H, Ph, R² = H, Ph, substituted Ph) with salicylic acid derivative II gave intermediate Schiff bases which underwent reductive cyclization with NaNB₄ to give thiazoloquinazolines III. Amination of II by R²NH₂ (R² = Ph, Et) gave the corresponding Schiff bases which were cyclized by HSCH₂CO₂H to give thiazolidinones IV and by ClCH₂COCl to give azetidinone V. Addnl. obtained were benzoisoquinoline and pyridoquinazoline derivatives 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. 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. 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 6318-74-7

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

The rates of reaction of α-halo ketones with thiosemicarbazides was written by Okamiya, Jiro. And the article was included in Nippon Kagaku Zasshi in 1962.Recommanded Product: 4,5-Diphenylthiazol-2-amine This article mentions the following:

The rates of reaction of phenacyl bromides with thiosemicarbazides were determined by conductivity measurement in EtOH. The reaction is second order up to 85% completion; the rate constant is obtained. The activation energies are 10.511.3 kcal./mole for the reaction of H₂NCSNHNHPh (I) and 8.5-9.3 kcal./mole for H₂NCSNHNH₂ (II). The activation energy for the reaction between PhC(:NOH)CH₂Br and NH₂CSNH₂ (III) or II is obtained as 10.2 or 6.6 kcal./mole. Thus, the reaction rate is shown as III > II > I and the reaction of oximes is much slower than that of the parent α-halo ketone itself. Hammett’s rule is applicable to the reaction and p is obtained as 0.63 and 0.74 for I and II, resp. The reaction products, 2-amino-5-(p-aminophenyl)thiazoles were prepared Bromomethyl ketone (0.003 mole), 0.003 mole I, and 20 cc. EtOH were heated 2 hrs., heated 30 min. after addition of 1 cc. HCl, 50 cc. H₂O added, and the mixture filtered after boiling and basified with NH₃ to give 55-90% yield. Methyl ketone, iodine, and I were heated 8 hrs. and treated similarly to give 40-70% yield. Thus, the following 4-substituted 2-amino-5(p-aminophenyl)thiazoles (IV) are obtained (R and m. p. given): H, 204°; Ph, 200-1°; p-MeC₆H₄, 190°; o-MeC₆H₄,210°; p-MeOC₆H₄, 237°; p-ClC₆H₄, 224°; p-BrC₆H₄, 247°; m-BrC₆H₄, 213-14°; m-IC₆H₄, 261°; m-IC₆H₄, 195°; m-O₂NC₆H₄, 252°; m-O₂NC₆H₄, 231°; o-O₂NC₆H₄, 241°; p-H₂NC₆H₄, 111° and 223° (double m.p.); p-PhC₆H₄, 237°; α-C₁₀₀H₇, 155°. KOH (5 g.) in 5 cc. H₂O was saturated with H₂S and 5 g. PhCOCHBrPh in 10 cc. EtOH added to give 2.5 g. PhCOCH₂Ph (V) after 2 hrs. heating. PhCOCHClPh (1.1 g.) in EtOH and III EtOH were mixed and heated 2 hrs. with 3.5 cc. 3N NaOH after standing 3 hrs. to give 0.1 g. V and 0.8 g. 2-amino-4,5diphenylthiazole, m. 188°. 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. 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.Recommanded Product: 4,5-Diphenylthiazol-2-amine

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

C-H Functionalization of Benzothiazoles via Thiazol-2-yl-phosphonium Intermediates was written by Zi, You;Schoemberg, Fritz;Wagner, Konrad;Vilotijevic, Ivan. And the article was included in Organic Letters in 2020.Application of 1843-21-6 This article mentions the following:

Benzothiazoles undergo regioselective C2-H functionalization with triphenylphosphine to form thiazol-2-yl-triphenylphosphonium salts, and these phosphonium salts react with a wide range of O- and N-centered nucleophiles to give the corresponding ethers, amines, and C-N biaryls. The reactions proceed under mild conditions and allow for the recovery of triphenylphosphine at the end of the sequence. In the presence of hydroxide, phosphonium salts undergo disproportionation, resulting in the reduction of the benzothiazole, which is useful for specific C2 deuteration of benzothiazoles. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6Application 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. 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.Application of 1843-21-6

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

The reaction of benzothiazolyl substituted α-phosphorylmethyl sulfoxides with several amines was written by Morita, Hiroyuki;Tashiro, Shintaro;Takeda, Masahiro;Yamada, Nobuhiko;Sheikh, Chanmiya Md.;Kawaguchi, Hiroyuki. And the article was included in Tetrahedron in 2008.COA of Formula: C13H10N2S This article mentions the following:

The reactivities of α-phosphorylmethyl benzothiazolyl sulfoxides in the thermolyses and in the presence of several amines, such as aniline, benzylamine, piperidine, morpholine, and pyrrolidine was examined Thermolyses of the derivatives in the presence of 2,3-dimethyl-1,3-butadiene afforded 2-phosphoryl substituted 4,5-dimethyl-3,6-dihydro-2H-thiopyran S-oxide. In the reaction with amines, the complex product mixture, which contains α-phosphorylmethyl benzothiazolyl sulfides, α-phosphorylmethyl disulfides, and 2-amino substituted benzothiazole was formed besides the target phosphinecarbothioamides. Several mechanistic studies were performed to elucidate the formation mechanism, particularly for deoxygenated products from the starting sulfoxides. In the experiment, the researchers used many compounds, for example, N-Phenylbenzo[d]thiazol-2-amine (cas: 1843-21-6COA of Formula: C13H10N2S).

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

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

A novel small-molecule inhibitor of IL-6 signalling was written by Zinzalla, Giovanna;Haque, Mohammad R.;Piku Basu, B.;Anderson, John;Kaye, Samantha L.;Haider, Shozeb;Hasan, Fyeza;Antonow, Dyeison;Essex, Samantha;Rahman, Khondaker M.;Palmer, Jonathan;Morgenstern, Daniel;Wilderspin, Andrew F.;Neidle, Stephen;Thurston, David E.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2010.Formula: C4H6N2S This article mentions the following:

A small library of pyrrolidinesulfonylaryl mols., e.g. I, has been synthesized via an efficient 4-step route, and members evaluated for their ability to inhibit IL-6 signalling. One mol., I, was found to have promising activity against IL-6/STAT3 (interleukin-6/signal transducer and activator of transcription-3) signalling at the low micromolar level, and to selectively inhibit phosphorylation of STAT3 (but not STAT1) in IL-6 stimulated MDA-MB-231 breast cancer and HeLa cell lines. It was also selectively cytostatic in MDA-MB-231 (STAT3-dependent) vs. A4 (STAT3-null) cells suggesting STAT3-specific inhibitory properties. In the experiment, the researchers used many compounds, for example, Thiazol-2-ylmethanamine (cas: 55661-33-1Formula: 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). 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: C4H6N2S

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