Day: December 6, 2022

Xu, Jia published the artcileSynthesis of tizanidine hydrochloride, Product Details of C6H4ClN3S, the publication is Zhongguo Yiyao Gongye Zazhi (2005), 36(10), 593-595, database is CAplus.

Tizanidine hydrochloride [i.e., 5-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-2,1,3-benzothiadiazol-4-amine hydrochloride] was synthesized from 4-chloro-2-nitroaniline by reduction with Zn/NaOH, cyclization, nitration and reduction of nitro group with Fe/HOAc to afford 5-chloro-4-amino-2,1,3-benzothiadiazole which subsequently was subjected to condensation with 1-acetyl-2-imidazolidinone, hydrolysis and then HCl salt formation with an overall yield of 46%.

Zhongguo Yiyao Gongye Zazhi published new progress about 30536-19-7. 30536-19-7 belongs to thiazole, auxiliary class Other Aromatic Heterocyclic,Chloride,Amine, name is 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine, and the molecular formula is C10H15NO, Product Details of C6H4ClN3S.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Wu, Bei published the artcileImproved synthesis of tizanidine hydrochloride, Category: thiazole, the publication is Zhongguo Xinyao Zazhi (2006), 15(8), 621-623, database is CAplus.

The synthetic way of tizanidine hydrochloride [i.e., 5-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-2,1,3-benzothiadiazol-4-amine hydrochloride] is reported. Tizanidine hydrochloride was synthesized using 4-chloro-2-nitroaniline as a starting material via several steps, including reduction with hydrazine/Fe-C, cyclization, nitration and reduction of nitro group with Fe/HOAc, condensation of 5-chloro-4-amino-2,1,3-benzothiadiazole with N-acetyl-2-imidazolidinone, alcoholysis and salt formation. The total yield of the target compound was 52.4%. The structure of the target compound was confirmed by IR, ¹H-NMR, ¹³C-NMR, MS and element anal. This improved synthetic procedure was mild and easily manipulated.

Zhongguo Xinyao Zazhi published new progress about 30536-19-7. 30536-19-7 belongs to thiazole, auxiliary class Other Aromatic Heterocyclic,Chloride,Amine, name is 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine, and the molecular formula is C2H4ClNO, Category: thiazole.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Wu, Xishan published the artcileDiscovery and Characterization of Benzimidazole Derivative XY123 as a Potent, Selective, and Orally Available RORγ Inverse Agonist, Application In Synthesis of 92-36-4, the publication is Journal of Medicinal Chemistry (2021), 64(12), 8775-8797, database is CAplus and MEDLINE.

Receptor-related orphan receptor γ (RORγ) has emerged as an attractive therapeutic target for the treatment of cancer and inflammatory diseases. Herein, we report our effort on the discovery, optimization, and evaluation of benzothiazole and benzimidazole derivatives as novel inverse agonists of RORγ. The representative compound 27h (designated as XY123) (I) potently inhibited the RORγ transcription activity with a half-maximal inhibitory concentration (IC₅₀) value of 64 nM and showed excellent selectivity against other nuclear receptors. 27H also potently suppressed cell proliferation, colony formation, and the expression of androgen receptor (AR)-regulated genes in AR-pos. prostate cancer cell lines. In addition, 27h demonstrated good metabolic stability and a pharmacokinetic property with reasonable oral bioavailability (32.41%) and moderate half-life (t_1/2 = 4.98 h). Significantly, oral administration of compound 27h achieved complete and long-lasting tumor regression in the 22Rv1 xenograft tumor model in mice. Compound 27h may serve as a new valuable lead compound for further development of drugs for the treatment of prostate cancer.

Journal of Medicinal Chemistry published new progress about 92-36-4. 92-36-4 belongs to thiazole, auxiliary class Organic Pigment, name is 2-(4-Aminophenyl)-6-methylbenzothiazole, and the molecular formula is C9H11BO2, Application In Synthesis of 92-36-4.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Tank, Pragya published the artcileViscometric studies of Cu(II) surfactants derived from mustard oil in benzene at 303.15 K, Application of 6-Chlorobenzothiazol-2-ylamine, the publication is Tenside, Surfactants, Detergents (2019), 56(2), 158-163, database is CAplus.

The viscosity, specific viscosity, and fluidity of Cu(II) surfactant complexes derived from mustard oil with urea/thiourea/2-amino-6-chloro benzothiazole in a non-aqueous solvent has been determined at a constant temperature of 303.15 K. The results were used to determine the critical micelle concentration (CMC), soap complex-solvent interactions and the effect of chain length of the surfactant mol. on various parameters. The conclusions with regard to solute-solute and solute-solvent interaction have been discussed in terms of well-known Moulik and Jones-Dole equations. The effect of surfactant concentration on the viscosity of the solution in non-polar solvent has been discussed. The observations suggested that the structure breaking effect by the solute on the solvent mols. is more prominent above CMC as compared to below CMC after the formation of the micelles. This information plays a role in various industrial and biol. applications.

Tenside, Surfactants, Detergents published new progress about 95-24-9. 95-24-9 belongs to thiazole, auxiliary class Organic Pigment, name is 6-Chlorobenzothiazol-2-ylamine, and the molecular formula is C5H10O2S, Application of 6-Chlorobenzothiazol-2-ylamine.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Behera, G. B. published the artcileQuaternization at an Sp² nitrogen. II. An analysis on the substituent effect and on the nature of the transition state, Safety of 4-(Naphthalen-1-yl)thiazol-2-amine, the publication is Bulletin of the Chemical Society of Japan (1979), 52(2), 604-7, database is CAplus.

The kinetics of N-phenacylation of a number of substituted thiazoles with substituted phenacyl bromides were investigated in PhNO₂ and in a number of other dipolar aprotic solvents. The rate constants of 2-amino-4-phenylthiazoles and 2-aminobenzothiazoles were calculated with suitably developed equations. The deviation of the observed values from the calculated results was ascribed to the steric effect. A 7-membered H-bonded transition state was proposed on the basis of the results obtained from the substituent and medium effects.

Bulletin of the Chemical Society of Japan published new progress about 56503-96-9. 56503-96-9 belongs to thiazole, auxiliary class Thiazole,Amine,Naphthalene, name is 4-(Naphthalen-1-yl)thiazol-2-amine, and the molecular formula is C13H10N2S, Safety of 4-(Naphthalen-1-yl)thiazol-2-amine.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Dai, Wen published the artcileHighly Chemoselective and Enantioselective Catalytic Oxidation of Heteroaromatic Sulfides via High-Valent Manganese(IV)-Oxo Cation Radical Oxidizing Intermediates, HPLC of Formula: 5053-24-7, the publication is ACS Catalysis (2017), 7(7), 4890-4895, database is CAplus.

A manganese complex with a porphyrin-like ligand that catalyzes the highly chemoselective and enantioselective oxidation of heteroaromatic sulfides, including imidazole, benzimidazole, indole, pyridine, pyrimidine, pyrazine, sym-triazine, thiophene, thiazole, benzothiazole, and benzoxazole, with hydrogen peroxide is described, furnishing the corresponding sulfoxides in good to excellent yields and enantioselectivities (up to 90% yield and up to >99% ee) within a short reaction time (0.5 h). The practical utility of the method has been demonstrated in the gram-scale synthesis of chiral sulfoxide. Mechanistic studies, performed with ¹⁸O-labeled water (H₂¹⁸O), hydrogen peroxide (H₂¹⁸O₂), and cumyl hydroperoxide, reveal that a highvalent manganese-oxo species is generated as the oxygen atom delivering agent via carboxylic acid assisted heterolysis of O-O bonds. D. functional theory (DFT) calculations were also carried out to give further insight into the mechanism of manganese-catalyzed sulfoxidation On the basis of the theor. study, the coupled high-valent manganese(IV)-oxo cation radical species, which bears obvious similarities with that of reactive intermediates in the catalytic oxygenation reactions based on the cytochrome P 450 and metalloporphyrin models, has been proposed as the reactive oxidant in the non-heme manganese catalyst system.

ACS Catalysis published new progress about 5053-24-7. 5053-24-7 belongs to thiazole, auxiliary class Thiazole,sulfides, name is 2-(Methylthio)thiazole, and the molecular formula is C4H5NS2, HPLC of Formula: 5053-24-7.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Nath, Rajarshi published the artcileSynthesis and anticonvulsant evaluation of indoline derivatives of functionalized aryloxadiazole amine and benzothiazole acetamide, Quality Control of 95-24-9, the publication is Journal of Molecular Structure (2021), 129742, database is CAplus.

A series of I [R = H, 6-Cl, 5-O₂N, etc.] and II [R¹ = H, 4-MeO, 2-O₂N, 4-O₂N; R² = H, 5-Cl, 5-Br] were designed, synthesized and fulfilled structural requirement of pharmacophore and evaluated for anticonvulsant activities using maximal electroshock test (MES), s.c. pentylenetetrazole (scPTZ) seizures and neurotoxicity by motor impairment model in mice. The most active compound I [R = 6-Cl] showed significant anticonvulsant activity against both MES and scPTZ screens and emerged as most effective anticonvulsant compound with median dose of 35.7 mg/kg (MES ED₅₀), 88.15 mg/kg (scPTZ ED₅₀) and toxic dose (TD₅₀) was found to be > 500mg/kg. In-silico studies including mol. docking study were carried out to establish the mol. interaction of potent compound I [R = 6-Cl] in both Na⁺ channel and GABA_A receptors. The prediction of pharmacokinetic parameters and distance mapping of compounds were performed to establish the drug likeness property.

Journal of Molecular Structure published new progress about 95-24-9. 95-24-9 belongs to thiazole, auxiliary class Organic Pigment, name is 6-Chlorobenzothiazol-2-ylamine, and the molecular formula is C7H5ClN2S, Quality Control of 95-24-9.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Gao, Kai published the artcileNanoscale, automated, high throughput synthesis and screening for the accelerated discovery of protein modifiers, Recommanded Product: 6-Chlorobenzothiazol-2-ylamine, the publication is RSC Medicinal Chemistry (2021), 12(5), 809-818, database is CAplus and MEDLINE.

Hit finding in early drug discovery is often based on high throughput screening (HTS) of existing and historical compound libraries, which can limit chem. diversity, is time-consuming, very costly, and environmentally not sustainable. On-the-fly compound synthesis and in situ screening in a highly miniaturized and automated format has the potential to greatly reduce the medicinal chem. environmental footprint. Here, acoustic dispensing technol. has been used to synthesize a library in a 1536 well format based on the Groebke-Blackburn-Bienayme’ reaction (GBB-3CR) on a nanomole scale. The unpurified library was screened by differential scanning fluorimetry (DSF) and cross-validated using microscale thermophoresis (MST) against the oncogenic protein-protein interaction menin-MLL. Several GBB reaction products were found as μM menin binder, and the structural basis of the interactions with menin was elucidated by co-crystal structure anal. Miniaturization and automation of the organic synthesis and screening process can lead to an acceleration in the early drug discovery process, which is an alternative to classical HTS and a step towards the paradigm of continuous manufacturing

RSC Medicinal Chemistry published new progress about 95-24-9. 95-24-9 belongs to thiazole, auxiliary class Organic Pigment, name is 6-Chlorobenzothiazol-2-ylamine, and the molecular formula is C7H5ClN2S, Recommanded Product: 6-Chlorobenzothiazol-2-ylamine.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Ikhtiarini, Asefin Nurul published the artcileOptimization of ultrasound-assisted extraction and the antioxidant activities of Sidaguri (Sida rhombifolia), Synthetic Route of 30931-67-0, the publication is Journal of Applied Pharmaceutical Science (2021), 11(8), 070-076, database is CAplus.

Sidaguri (Sida rhombifolia) is widely distributed in tropical and subtropical regions and has been reported to possess many bioactive compounds that are beneficial for human health, including polyphenolics having antioxidant activities. The objective of this study was (1) to optimize ultrasound-assisted extraction (UAE) of Sidaguri and (2) to evaluate antioxidant activities of extracts resulting from the optimized condition using radical scavenging assay of 2,2′-diphenil-1-picrylhydrazyl (DPPH) and 2,2′-azinobis-3-ethylbenzothiazoline-6-sulfonic acid. The optimum UAE conditions obtained were solvent to solid ratio of 26:1, temperature of extraction of 45.45°C, methanol concentration of 42%, power of sonication of 86%, and time of extraction of 5 min. Sidaguri obtained from locations of Kretek and Ngemplak had the highest radical scavenging activity accounting for 83.69% ± 0.30% and 82.95% ± 0.49%, resp.

Journal of Applied Pharmaceutical Science published new progress about 30931-67-0. 30931-67-0 belongs to thiazole, auxiliary class Salt,Hydrazine,Amine,Benzothiazole, name is Ammonium 2,2′-(hydrazine-1,2-diylidene)bis(3-ethyl-2,3-dihydrobenzo[d]thiazole-6-sulfonate), and the molecular formula is C18H24N6O6S4, Synthetic Route of 30931-67-0.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica

Chen, Yen Ting published the artcileParallel synthesis of a library of bidentate protein tyrosine phosphatase inhibitors based on the α-ketoacid motif, Application of 2-(4-Aminophenyl)-6-methylbenzothiazole, the publication is Bioorganic & Medicinal Chemistry (2004), 12(12), 3289-3298, database is CAplus and MEDLINE.

Protein tyrosine phosphatases (PTPases) regulate intracellular signal transduction pathways by controlling the level of tyrosine phosphorylation in cells. These enzymes play an important role in a variety of diseases including type II diabetes and infection by the bacterium Yersinia pestis, which is the causative agent of bubonic plague. This report describes the synthesis, using parallel solution-phase methods, of a library of 104 potential inhibitors of PTPases. The library members are based on the bis(aryl α-ketocarboxylic acid) motif that incorporates a carboxylic acid on the central benzene linker. This carboxylic acid was coupled with a variety of different aromatic amines through an amide linkage. The aromatic component of the resulting amides is designed to make contacts with residues that surround the active site of the PTPase. The library was screened against the Yersinia PTPase and PTP1B. Based upon the screening results, four members of the library were selected for further study. These four compounds were evaluated against the Yersinia PTPase, PTP1B, TCPTP, CD45, and LAR. Compound 14 has an IC₅₀ value of 590 nM against PTP1B and is a reversible competitive inhibitor. This affinity represents a greater than 120-fold increase in potency over compound 2, the parent structure upon which the library was based. A second inhibitor, compound 12, has an IC₅₀ value of 240 nM against the Yersinia PTPase. In general, the selectivity of the inhibitors for PTP1B was good compared to LAR, but modest when compared to TCPTP and CD45.

Bioorganic & Medicinal Chemistry published new progress about 92-36-4. 92-36-4 belongs to thiazole, auxiliary class Organic Pigment, name is 2-(4-Aminophenyl)-6-methylbenzothiazole, and the molecular formula is C14H12N2S, Application of 2-(4-Aminophenyl)-6-methylbenzothiazole.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/thiazole,
Thiazole | chemical compound | Britannica