Heterocyclic Building Blocks-Thiazole

Mor, Satbir published the artcileSynthesis, Type II diabetes inhibitory activity, antimicrobial evaluation and docking studies of indeno[1,2-c]pyrazol-4(1H)-ones, HPLC of Formula: 95-24-9, the publication is Medicinal Chemistry Research (2020), 29(1), 46-62, database is CAplus and MEDLINE.

A convenient and efficient synthesis of indeno[1,2-c]pyrazol-4(1H)-ones I (R¹ = Me, i-Pr, i-butyl; R² = H, Me, Cl, etc.) by the reaction of a variety of 2-acyl-(1H)-indene-1,3(2H)-diones and 2-hydrazinylbenzo[d]thiazole/2-hydrazinyl-6-substitutedbenzo[d]thiazoles in the presence of glacial acetic acid in good yields is reported. All the synthesized indeno[1,2-c]pyrazol-4(1H)-ones I were assayed for their in vitro Type II diabetes inhibitory activity by using Acarbose as standard drug and in vitro antimicrobial activity utilizing Streptomycin and Fluconazole as reference drugs. Among the synthesized derivatives, I (R¹ = Me; R² = Br) (IC₅₀ = 6.71 μg/mL) was found to be more potent against α-glucosidase enzyme as compared with the standard Acarbose (IC₅₀ = 9.35 μg/mL) and I (R¹ = i-propyl; R² = Cl) (IC₅₀ = 11.90 μg/mL) exhibited good inhibitory activity against α-amylase enzyme as compared with the standard Acarbose (IC₅₀ = 22.87 μg/mL). Also, all the titled compounds showed good antimicrobial activity. In addition, in vitro α-glucosidase and α-amylase inhibition were supported by docking studies performed on the derivatives I (R¹ = Me, i-butyl; R² = Br) resp.

Medicinal Chemistry Research 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, HPLC of Formula: 95-24-9.

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

Nishad, Ravi K. published the artcileDesign and Synthesis of 2-Substituted Benzothiazole Derivatives as Antioxidant and Antimicrobial Agents, Computed Properties of 95-24-9, the publication is Current Bioactive Compounds (2020), 16(8), 1242-1248, database is CAplus.

An upsurge in the number of antibiotic-resistant microbial infections has warranted the discovery and development of new antibiotics. This is a matter of great concern for effective therapy for a search of novel antimicrobial agents. Literature has a number of reports of involvement of oxidative stress due to an imbalance between the generation and neutralization of free radicals in many diseases. Heterocyclic compounds have been involved in the treatment of various disorders. Benzothiazole is one such heterocyclic nucleus having benzene ring merged with the thiazole ring. Among the various substitutions possible in this nucleus, substitutions at position-2 have already been reported with potential bioactivities. Thus, different substituted compounds have been synthesized which could serve as antimicrobials and antioxidants. Benzothiazole derivatives (B₁-B₇) were synthesized by two-step reactions and the structures were confirmed through IR, mass and NMR spectroscopy. The compounds were evaluated for in vitro antioxidant and antimicrobial activities using standard methods. The results of antibacterial and antifungal activity showed that compound B₄ exhibited maximum activity against all the tested strains of microorganisms with the zone of inhibition 17.1-18.5 mm and MIC value 1.1-1.5μg/mL. Compound B₅ exhibited potent antioxidant activity. The compounds substituted with halogen on the aryl ring showed increased antimicrobial activity as seen in the case of compound B₄ (6-fluoro). The compounds substituted with a hydroxyl group (B₅) exhibited good antioxidant activity.

Current Bioactive Compounds 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, Computed Properties of 95-24-9.

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

Oh, Se Young published the artcileDurability and polarization characteristics of PVA polarizing film prepared with a dichroic azo dye, HPLC of Formula: 92-36-4, the publication is Kongop Hwahak (2000), 11(4), 426-431, database is CAplus.

A novel dichroic azo dyes having a benzothiazole moiety were synthesized and used to prepare poly(vinyl alc.) (PVA)-based polarizing films for application in liquid crystal displays. The UV-Visible spectrum of PVA-dye polarizing film showed absorption bands corresponding to aromatic rings and dye chromophoric species at 326 and 584 nm. The polarization efficiency and the transmittance of PVA-dye polarizing film were significantly influenced by dye concentration, dipping time and addition of salt catalyst. The PVA-dye polarizing film exhibited a high polarization efficiency of 99.5% and a good transmittance of 42%. Especially, the heat and humidity resistance of PVA-dye polarizing film was higher than that of a conventional PVA-I₂ polarizing film.

Kongop Hwahak 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, HPLC of Formula: 92-36-4.

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

Li, Zijie published the artcileEfficient room temperature catalytic synthesis of alternating conjugated copolymers via C-S bond activation, Synthetic Route of 5053-24-7, the publication is Nature Communications (2022), 13(1), 144, database is CAplus and MEDLINE.

Structural defects in conjugated copolymers are severely detrimental to the optoelectronic properties and the performance of the resulting electronic devices fabricated from them. Therefore, the much-desired precision synthesis of conjugated copolymers with highly regular repeat units is important, but presents a significant challenge to synthetic materials chemists. To this end, aryl sulfides are naturally abundant substances and offer unrealized potential in cross-coupling reactions. Here we report an efficient room temperature polycondensation protocol which implements aryl disulfide C-S activation to produce defect-minimized semiconducting conjugated copolymers with broad scope and applicability. Thus, a broad series of arylstannanes and thioethers are employed via the present protocol to afford copolymers with number-average mol. weights (Mns) of 10.0-45.0 kDa. MALDI and NMR anal. of selected copolymers reveals minimal structural defects. Moreover, the polymer trap d. here is smaller and the field effect mobility higher than that in the analogous polymer synthesized through thermal-activation Stille coupling.

Nature Communications 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, Synthetic Route of 5053-24-7.

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

Zhu, Yu-Shen published the artcileIodine-catalyzed amination of benzothiazoles with KSeCN in water to access primary 2-aminobenzothiazoles, Computed Properties of 95-24-9, the publication is Chinese Chemical Letters (2022), 33(3), 1497-1500, database is CAplus.

A facile and sustainable approach for the amination of benzothiazoles I (X = H, N; R = H, 4-Cl, 5-OMe, 6-NO₂, 7-C(O)OMe; R¹ = H) with KSeCN using iodine as the catalyst in water has been disclosed under transition-metal free conditions. The reaction proceeded smoothly to afford various primary 2-amino benzothiazoles I (R¹ = NH₂) in up to 96% yield. A series of control experiments were performed, suggesting that a ring-opening mechanism was involved via a radical process. This protocol provides efficient synthesis of primary 2-aminobenzothiazole I (R¹ = NH₂).

Chinese Chemical Letters 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 C8H5F3O3, Computed Properties of 95-24-9.

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

Liu, Xiang-Wei published the artcileDiversified syntheses of multifunctionalized thiazole derivatives via regioselective and programmed C-H activation, Related Products of thiazole, the publication is Chemical Communications (Cambridge, United Kingdom) (2015), 51(22), 4599-4602, database is CAplus and MEDLINE.

The sequential construction of diversified multifunctionalized thiazole derivatives through Pd-catalyzed regioselective C-H alkenylation was accomplished. This versatile approach provides the diversified thiazole derivatives featuring orthogonal substitution patterns at the C-2, C-4 and C-5 positions from mono-substituted (2- or 4-substituted) thiazole derivatives or even more challenging simple thiazole.

Chemical Communications (Cambridge, United Kingdom) 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, Related Products of thiazole.

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

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