Month: November 2022

He, Wei-Bao published the artcileVisible-light-initiated malic acid-promoted cascade coupling/cyclization of aromatic amines and KSCN to 2-aminobenzothiazoles without photocatalyst, Quality Control of 95-24-9, the publication is Chinese Chemical Letters (2020), 31(7), 1895-1898, database is CAplus.

By using ambient air as the oxidant and malic acid as the promoter, a practical method for the preparation of 2-aminobenzothiazoles through visible-light-initiated cascade reaction of aromatic amines and KSCN in eco-friendly bis(methoxypropy)ether under metal-, hazardous additive-, photocatalyst-free conditions was established.

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 C7H5ClN2S, Quality Control of 95-24-9.

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

Chanon, Michel published the artcileAlkylation reactions of thiazoles. II. Comparative study of the pK(sub a) values of various 2-(methylthio)thiazoles and of their kinetic constants in the reaction with methyl iodide, Product Details of C4H5NS2, the publication is Bulletin de la Societe Chimique de France (1968), 2885-9, database is CAplus.

The 4- (I) and 5-di-Me derivatives (II) of 2-(methylthio)thiazole were treated with MeI in Me2CO at 20, 25, and 30° and the reaction site, order of reaction, and the magnitude of activation determined The pKa values of the bases were measured. The pKa values were lowered by the influence of the methylthio group; the protonation reaction on N was less sensitive to steric effects than acylation; the methylthio group withdrew the electrons in the thiazole ring and sterically hindered the reaction site; and the Me substituent increased the rate constants

Bulletin de la Societe Chimique de France 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, Product Details of C4H5NS2.

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

HajKacem, Sihem published the artcileBioreactor Membranes for Laccase Immobilization Optimized by Ionic Liquids and Crosslinking Agents, Category: thiazole, the publication is Applied Biochemistry and Biotechnology (2020), 190(1), 1-17, database is CAplus and MEDLINE.

A novel concept of membrane bioreactor based on polymeric ionic liquids laccase membrane has been implemented in batch process for decolorization of the anthraquinonic dye Remazol Brillant Blue R (RBBR). New laccase immobilization strategy has been optimized by casting the enzyme into a polymeric inclusion membrane (PIM) using ionic liquids (ILs) and polyvinyl chloride (PVC) leading to laccase polymeric IL membrane (PILM). Four different ILs (1-octyl-3-metylimidazolium bis(trifluoromethylsulfonyl)imide, [OMIM][NTF₂]; cholinium bis(trifluoromethylsulfonyl)imide, [Ch ol][NTF₂]; cholinium dihydrogenphosphate, [Chol][H₂PO₄] and hydroxyethylammonium formate, [HEA][Fo]) have been screened and mixed to constitute the active phase of the support of PIM. This strategy has been fully succeeded since high laccase immobilization rates were recorded (about 98%) when using the optimal mixture containing three ILs (45% [OMIM][NTf₂]/5% [Chol][NTf₂]/2.5% [HEA][Fo]) and supplemented by 0.5% glutaraldehyde. It was found that such mixture contributes to increase the stability and reusability of laccase-PILM during eight successive assays in a batch discontinued stirred reactor. Decolorization rate of 75% has been reached in the batch decolorization process of RBBR with high reusability yield.

Applied Biochemistry and Biotechnology 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, Category: thiazole.

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

Li, Jun published the artcileComparison of fruit quality and characteristics at different growth stages of kumquat from Rongan, Recommanded Product: Ammonium 2,2′-(hydrazine-1,2-diylidene)bis(3-ethyl-2,3-dihydrobenzo[d]thiazole-6-sulfonate), the publication is Xiandai Shipin Keji (2021), 37(2), 138-146, database is CAplus.

A study on the dynamic change of the physicochem. properties and the active ingredients of kumquat fruits at different growth stages was carried out with Guangxi Rongan specialty Fortunella margarita (Lour.) ′Youpi′ (YP) and Fortunella margarita (Lour.) ′Cuipi′ (CP). The results showed that from Sept. to Dec., the phys. and chem. indexes such as single fruit weight, juice yield, pH value, soluble solids, and sugar-acid ratio of kumquat increased, and the fruit seed rate and titratable acid content decreased. The main sugar content rose from 39.04 and 32.38 mg/g to 111.23 and 137.11 mg/g, resp. The main organic acids were ascorbic acid, malic acid and oxalic acid, and the ascorbic acid content increased first and then decreased. In Oct., kumquat ascorbic acid content peaked (48.23 and 23.20 mg/g, resp.). While malic acid and oxalic acid contents continued to decline. Compared with Sept., the total flavonoid contents of YP and CP kumquat decreased from 3.45 and 2.14 mg RE/g to 1.21 and 0.76 mg RE/g resp. in Dec., in which the characteristic flavonoid fortunellin content increased significantly. The total phenol content and antioxidant activity decreased significantly. Between the two varieties, there were no significant differences in mature single fruit weight, titratable acid, TFs, and hesperidin content, and the fruit seed rate, ascorbic acid, fortunellin, TPs content, and total antioxidant capacity of YP were significantly higher than those of CP. While the juice yield, fruit juice pH, soluble solids, sugar-acid ratio, fructose, glucose, sucrose, malic acid, oxalic acid, and rutin content of YP were significantly lower than those of CP. This study clarifies the fruit quality characteristics of the two kinds of kumquat at different growth stages and provides a theor. basis for the development and utilization of kumquat fruit.

Xiandai Shipin Keji 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, Recommanded Product: Ammonium 2,2′-(hydrazine-1,2-diylidene)bis(3-ethyl-2,3-dihydrobenzo[d]thiazole-6-sulfonate).

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

Li, Yudong published the artcileProton Transfer Can Govern Regioselectivity Assisted by Iron Catalysis, Application of 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine, the publication is iScience (2020), 23(6), 101214, database is CAplus and MEDLINE.

Ortho-selective aromatic C-H functionalization is frequently used in organic synthesis and chem./pharmaceutical industries. However, this reaction relies heavily on the use of directing groups suffering from limited substrate scope and extra steps to put on and remove the directing/protecting groups. Herein authors present the previously neglected concept that enables good to nearly complete selective ortho position. Proton transfer was utilized to tune the electron d. on the aryl ring and determine the positional selectivity of electrophilic substitution. Consistently with deuteration experiments and DFT studies, this work demonstrates that acid-promoted proton transfer directs accelerated ortho-selective halogenation of NH/OH contained aromatic amines/phenols with excellent selectivity (>40 examples; up to 98:2 ortho/para selectivity). The application potential of this Fe-catalyzed method is demonstrated by the convenient synthesis of three alkaloids and tizanidine. This report raises the possibility that proton transfer could serve as the basis of developing new selective C-H functionalization reactions.

iScience 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 C6H4ClN3S, Application of 5-Chlorobenzo[c][1,2,5]thiadiazol-4-amine.

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

Marcantonio, Karen M. published the artcileA practical preparation of 5-(ketoaryl)thiazoles, Synthetic Route of 5053-24-7, the publication is Tetrahedron Letters (2002), 43(49), 8845-8848, database is CAplus.

This article describes a facile synthesis of 2-substituted-5-(ketoaryl)thiazoles, which are important intermediates for the synthesis of biol. active compounds A variety of 2-substituted thiazole anions were added to aryl nitriles to provide the desired ketones after aqueous hydrolysis.

Tetrahedron Letters 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

Hoveyda, Hamid R. published the artcileOptimization of Novel Antagonists to the Neurokinin-3 Receptor for the Treatment of Sex-Hormone Disorders (Part II), Name: 3-Methyl-1,2,4-thiadiazole-5-carbohydrazide, the publication is ACS Medicinal Chemistry Letters (2015), 6(7), 736-740, database is CAplus and MEDLINE.

Further lead optimization on N-acyl-triazolopiperazine antagonists to the neurokinin-3 receptor (NK₃R) based on the concurrent improvement in bioactivity and ligand lipophilic efficiency (LLE) is reported. Overall, compound I (LLE > 6) emerged as the most efficacious in castrated rat and monkey to lower plasma LH, and it displayed the best off-target safety profile that led to its clin. candidate nomination for the treatment of sex-hormone disorders.

ACS Medicinal Chemistry Letters published new progress about 1375066-73-1. 1375066-73-1 belongs to thiazole, auxiliary class Thiadiazole,Hydrazine,Amine,Hydrazide,Amide, name is 3-Methyl-1,2,4-thiadiazole-5-carbohydrazide, and the molecular formula is C4H6N4OS, Name: 3-Methyl-1,2,4-thiadiazole-5-carbohydrazide.

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

Hoveyda, Hamid R. published the artcileDiscovery and Optimization of Novel Antagonists to the Human Neurokinin-3 Receptor for the Treatment of Sex-Hormone Disorders (Part I), HPLC of Formula: 1375066-73-1, the publication is Journal of Medicinal Chemistry (2015), 58(7), 3060-3082, database is CAplus and MEDLINE.

Neurokinin-3 receptor (NK₃R) has recently emerged as important in modulating the tonic pulsatile gonadotropin-releasing hormone (GnRH) release. The authors therefore decided to explore NK₃R antagonists as therapeutics for sex-hormone disorders that can potentially benefit from lowering GnRH pulsatility with consequent diminished levels of plasma LH and correspondingly attenuated levels of circulating androgens and estrogens. The discovery and lead optimization of a novel N-acyl-triazolopiperazine NK₃R antagonist chemotype achieved through bioisosteric lead change from the high-throughput screening (HTS) hit is described. A concomitant improvement in the antagonist bioactivity and ligand lipophilic efficiency (LLE) parameter were the principal guidelines in the lead optimization efforts. Examples of advanced lead analogs to demonstrate the amenability of this chemotype to achieving a suitable pharmacokinetic (PK) profile are provided as well as pharmacokinetic-pharmacodynamic (PKPD) correlations to analyze the trends observed for LH inhibition in castrated rats and monkeys that served as preliminary in vivo efficacy models.

Journal of Medicinal Chemistry published new progress about 1375066-73-1. 1375066-73-1 belongs to thiazole, auxiliary class Thiadiazole,Hydrazine,Amine,Hydrazide,Amide, name is 3-Methyl-1,2,4-thiadiazole-5-carbohydrazide, and the molecular formula is C4H6N4OS, HPLC of Formula: 1375066-73-1.

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

Noerholm, Ann-Beth published the artcileSynthesis, Pharmacological and Structural Characterization, and Thermodynamic Aspects of GluA2-Positive Allosteric Modulators with a 3,4-Dihydro-2H-1,2,4-benzothiadiazine 1,1-Dioxide Scaffold, Formula: C10H11FN2O2S, the publication is Journal of Medicinal Chemistry (2013), 56(21), 8736-8745, database is CAplus and MEDLINE.

Pos. allosteric modulators of ionotropic glutamate receptors are potential compounds for treatment of cognitive disorders, e.g., Alzheimer’s disease. The modulators bind within the dimer interface of the ligand-binding domain (LBD) and stabilize the agonist-bound conformation, thereby slowing receptor desensitization and/or deactivation. Here we describe the synthesis and pharmacol. testing at GluA2 of a new generation of 3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxides. The most potent modulator I in complex with GluA2-LBD-L483Y-N754S was subjected to structural anal. by X-ray crystallog., and the thermodn. of binding was studied by isothermal titration calorimetry. Compound I binds to GluA2-LBD-L483Y-N754S with a K_d of 0.35 μM (ΔH = -7.5 kcal/mol and -TΔS = -1.3 kcal/mol). This is the first time that submicromolar binding affinity has been achieved for this type of pos. allosteric modulator. The major structural factor increasing the binding affinity of I seems to be interactions between the cyclopropyl group of I and the backbone of Phe495 and Met496.

Journal of Medicinal Chemistry published new progress about 1204572-55-3. 1204572-55-3 belongs to thiazole, auxiliary class Neuronal Signaling,GluR, name is 4-Cyclopropyl-7-fluoro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide, and the molecular formula is C10H11FN2O2S, Formula: C10H11FN2O2S.

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

Noerholm, Ann-Beth published the artcileThermodynamic Characterization of New Positive Allosteric Modulators Binding to the Glutamate Receptor A2 Ligand-Binding Domain: Combining Experimental and Computational Methods Unravels Differences in Driving Forces, Name: 4-Cyclopropyl-7-fluoro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide, the publication is Journal of Chemical Information and Modeling (2014), 54(12), 3404-3416, database is CAplus and MEDLINE.

Pos. allosteric modulation of the ionotropic glutamate receptor GluA2 presents a potential treatment of cognitive disorders, for example, Alzheimer’s disease. In the present study, the authors describe the synthesis, pharmacol., and thermodn. studies of a series of monofluoro-substituted 3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxides I [R = 5-F, 6-F, 7-F, 8-F]. Measurements of ligand binding by isothermal titration calorimetry (ITC) showed similar binding affinities for the modulator series at the GluA2 LBD but differences in the thermodn. driving forces. Binding of I [R = 7-F] and I [R = H] is enthalpy driven, and I [R = 5-F] and I [R = 6-F] are entropy driven. For I [R = 8-F], both quantities were equal in size. Thermodn. integration (TI) and one-step perturbation (OSP) were used to calculate the relative binding affinity of the modulators. The OSP calculations had a higher predictive power than those from TI, and combined with the shorter total simulation time, the authors found the OSP method to be more effective for this setup. Furthermore, from the mol. dynamics simulations, the authors extracted the enthalpies and entropies, and along with the ITC data, this suggested that the differences in binding free energies are largely explained by the direct ligand-surrounding enthalpies. Furthermore, the authors used the OSP setup to predict binding affinities for a series of polysubstituted fluorine compounds and monosubstituted Me compounds and used these predictions to characterize the modulator binding pocket for this scaffold of pos. allosteric modulators.

Journal of Chemical Information and Modeling published new progress about 1204572-55-3. 1204572-55-3 belongs to thiazole, auxiliary class Neuronal Signaling,GluR, name is 4-Cyclopropyl-7-fluoro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide, and the molecular formula is C10H11FN2O2S, Name: 4-Cyclopropyl-7-fluoro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide.

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