Day: November 29, 2022

Rao, Ashwin U. published the artcileSynthesis and structure-activity relationships of 2-(1,4′-bipiperidin-1′-yl)thiazolopyridines as H₃ receptor antagonists, SDS of cas: 31784-71-1, the publication is Bioorganic & Medicinal Chemistry Letters (2009), 19(21), 6176-6180, database is CAplus and MEDLINE.

A series of 2-(1,4′-bipiperidin-1′-yl)thiazolopyridines I (X = N, Y = CH; X = CH, Y = N; R = H, H₂N, CN, Cl, MeCONH, 4-NCC₆H₄, 2-fluoro-3-pyridyl, 5-pyrimidyl, etc.) was synthesized and evaluated as a new lead of non-imidazole histamine H₃ receptor antagonists. Introduction of diversity at the 6-position of the pyridine ring was designed to enhance in vitro potency and decrease hERG activity. The structure-activity relationships for these new thiazolopyridine antagonists are discussed.

Bioorganic & Medicinal Chemistry Letters published new progress about 31784-71-1. 31784-71-1 belongs to thiazole, auxiliary class Other Aromatic Heterocyclic,Chloride,Amine, name is 5-Chlorothiazolo[5,4-b]pyridin-2-amine, and the molecular formula is C6H4ClN3S, SDS of cas: 31784-71-1.

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

Fleau, Charlotte published the artcileChagas Disease Drug Discovery: Multiparametric Lead Optimization against Trypanosoma cruzi in Acylaminobenzothiazole Series, COA of Formula: C7H5ClN2S, the publication is Journal of Medicinal Chemistry (2019), 62(22), 10362-10375, database is CAplus and MEDLINE.

Acylaminobenzothiazole hits were identified as potential inhibitors of T. cruzi replication, a parasite responsible for Chagas Disease. We selected compound 1, N-(6-chlorobenzo[d]thiazol-2-yl)cyclopropanecarboxamide, for lead optimization, aiming to improve in parallel its anti-T. cruzi activity (IC50 = 0.630μM) and its human metabolic stability (human clearance = 9.57mL/min/g). A total of 39 analogs of 1 were synthesized and tested in vitro. We established a multiparametric structure activity relationship, allowing optimization of both anti-parasite activity, physicochem. parameters and ADME properties. We identified compound 50, N-(5-Fluoro-6-(trifluoromethyl)benzothiazol-2-yl)cyclopropanecarboxamide, as an advanced lead with an improved anti-T. cruzi activity in vitro (IC50 = 0.079μM), an enhanced metabolic stability (Human Clearance = 0.413mL/min/g) and opportunity for oral route of administration. After tolerability assessment, compound 50 demonstrated a promising in vivo efficacy.

Journal of 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, COA of Formula: C7H5ClN2S.

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

Acar Cevik, Ulviye published the artcileSynthesis of new benzothiazole derivatives bearing thiadiazole as monoamine oxidase inhibitors, Application of 6-Chlorobenzothiazol-2-ylamine, the publication is Journal of Heterocyclic Chemistry (2020), 57(5), 2225-2233, database is CAplus.

In this study, a novel series of benzothiazole-thiadiazole I (R¹ = Et, methoxyethyl, n-Pr, n-Bu; R² = H, Cl, NO₂) was synthesized. These compounds I were evaluated as inhibitors for types A and B MAO enzymes. Compounds I [(A), R¹ = methoxyethyl, R² = NO₂; R¹ = n-Bu, R² = NO₂, (B)] were the most active derivatives in the series with IC₅₀ values of 0.107 ± 0.003 and 0.128 ± 0.004, resp. Furthermore, compounds (A) and (B) were investigated for their cytotoxicity and found as non-cytotoxic.

Journal of Heterocyclic 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, Application of 6-Chlorobenzothiazol-2-ylamine.

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

Yu, Jianwei published the artcile2,1,3-Benzothiadiazole-5,6-dicarboxylicimide-Based Polymer Semiconductors for Organic Thin-Film Transistors and Polymer Solar Cells, Category: thiazole, the publication is ACS Applied Materials & Interfaces (2017), 9(48), 42167-42178, database is CAplus and MEDLINE.

A series of polymer semiconductors incorporating 2,1,3-benzothiadiazole-5,6-dicarboxylicimide (BTZI) as strong electron-withdrawing unit and an alkoxy-functionalized head-to-head linkage containing bithiophene or bithiazole as highly electron-rich co-unit are designed and synthesized. Because of the strong intramol. charge transfer characteristics, all three polymers BTZI-TRTOR (P1), BTZI-BTOR (P2), and BTZI-BTzOR (P3) exhibit narrow bandgaps of 1.13, 1.05, and 0.92 eV, resp., resulting in a very broad absorption ranging from 350 to 1400 nm. The highly electron-deficient 2,1,3-benzothiadiazole-5,6-dicarboxylicimide and alkoxy-functionalized bithiophene (or thiazole) lead to polymers with low-lying lowest unoccupied MOs (-3.96 to -4.28 eV) and high-lying highest occupied MOs (-5.01 to -5.20 eV). Hence, P1 and P3 show substantial and balanced ambipolar transport with electron mobilities/hole mobilities of up to 0.86/0.51 and 0.95/0.50 cm² V^-1 s^-1, resp., and polymer P2 containing the strongest donor unit exhibited unipolar p-type performance with an average hole mobility of 0.40 cm² V^-1 s^-1 in top-gate/bottom-contact thin-film transistors with gold as the source and drain electrodes. When incorporated into bulk heterojunction polymer solar cells, the narrow bandgap (1.13 eV) polymer P1 shows an encouraging power conversion efficiency of 4.15% with a relatively large open-circuit voltage of 0.69 V, which corresponds to a remarkably small energy loss of 0.44 eV. The power conversion efficiency of P1 is among the highest reported to date with such a small energy loss in polymer:fullerene solar cells.

ACS Applied Materials & Interfaces published new progress about 2215018-37-2. 2215018-37-2 belongs to thiazole, auxiliary class Thiazoles, name is 4,4′-Bis(octyloxy)-2,2′-bis(trimethylstannyl)-5,5′-bithiazole, and the molecular formula is C9H13NO2, Category: thiazole.

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

Kaseke, Tafadzwa published the artcileOxidative stability of pomegranate seed oil from blanched and microwave pretreated seeds: Kinetic and thermodynamic studiaaafes under accelerated conditions, HPLC of Formula: 30931-67-0, the publication is Journal of Food Processing and Preservation (2021), 45(10), e15798, database is CAplus.

This work aimed to evaluate the effects of blanching and microwave heating of pomegranate seed on the oxidative stability and shelf-life of ultrasound-assisted and ethanol extracted oil. Pomegranate seeds (cv. Herskawitz) were independently blanched at 95°C for 3 min and microwave heated at 261 W for 102 s. The oil samples were subjected to accelerated oxidation (30, 40, and 50°C) to evaluate lipid oxidation kinetics, thermodn. parameters, and estimate the shelf-life. The Arrhenius model and activated complex theory were used to estimate the energy for activation (E_a), enthalpy (ΔH ), entropy (ΔS ), and Gibbs-free energy (ΔG ), which varied from 6.2 to 8.59 kJ/mol, 3.69 to 6.38 kJ/mol, -146.62 to -155.06 J/K mol^-1, and 48.13 to 64.74 kJ/mol, resp. According to the thermodn. parameters, the lipid oxidation reactions in all oil samples were non-spontaneous, endothermic, and endergonic. Based on the developed Arrhenius models, blanching of pomegranate seed increased the oil shelf-life at 25°C from 21 to 24 days, while microwave pretreatment did not change the oil shelf-life. Seed pretreatment is a novel approach that could be used to enhance the oil antioxidant properties. This study has established that the blanching of seeds is beneficial in enhancing the storability and shelf life of pomegranate seed oil (PSO). In addition, the study has demonstrated that antioxidant compounds and fatty acid composition are indispensable factors in PSO oxidation The findings are useful in the design and establishment of PSO packaging, storage conditions, and application of modern technologies such as encapsulation to maximize its storability and retain the health-promoting properties.

Journal of Food Processing and Preservation 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, HPLC of Formula: 30931-67-0.

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

Hirose, Masaaki published the artcileDesign and synthesis of novel DFG-out RAF/vascular endothelial growth factor receptor 2 (VEGFR2) inhibitors: 3. Evaluation of 5-amino-linked thiazolo[5,4-d]pyrimidine and thiazolo[5,4-b]pyridine derivatives, Quality Control of 31784-71-1, the publication is Bioorganic & Medicinal Chemistry (2012), 20(18), 5600-5615, database is CAplus and MEDLINE.

Our aim was to discover RAF/vascular endothelial growth factor receptor 2 (VEGFR2) inhibitors that possess strong activity and sufficient oral absorption, and thus, we selected a 5-amino-linked thiazolo[5,4-d]pyrimidine derivative as the lead compound because of its potential kinase inhibitory activities and its desired solubility The novel tertiary 1-cyano-1-methylethoxy substituent was designed to occupy the hydrophobic region of ‘back pocket’ of BRAF on the basis of the X-ray co-crystal structure data of BRAF. In addition, we found that N-methylation of the amine linker could control the twisted mol. conformation leading to improved solubility These approaches produced N-Me thiazolo[5,4-b]pyridine-5-amine derivative 5 (I). To maximize the in vivo efficacy, we attempted salt formation of 5. Our result indicated that the besylate monohydrate salt form (5c) showed significant improvement of both solubility and oral absorption. Owing to the improved physicochem. properties, compound 5c demonstrated regressive antitumor efficacy in a HT-29 xenograft model.

Bioorganic & Medicinal Chemistry published new progress about 31784-71-1. 31784-71-1 belongs to thiazole, auxiliary class Other Aromatic Heterocyclic,Chloride,Amine, name is 5-Chlorothiazolo[5,4-b]pyridin-2-amine, and the molecular formula is C6H4ClN3S, Quality Control of 31784-71-1.

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

Tomoshige, Shusuke published the artcileDiscovery of Small Molecules that Induce the Degradation of Huntingtin, COA of Formula: C14H12N2S, the publication is Angewandte Chemie, International Edition (2017), 56(38), 11530-11533, database is CAplus and MEDLINE.

Huntington’s disease (HD) is an autosomal dominant neurodegenerative disorder caused by the aggregation of mutant huntingtin (mHtt), and removal of toxic mHtt is expected to be an effective therapeutic approach. The authors designed two small hybrid mols. by linking a ligand for ubiquitin ligase (cellular inhibitor of apoptosis protein 1; cIAP1) with probes for mHtt aggregates, anticipating that these compounds would recruit cIAP1 to mHtt and induce selective degradation by the ubiquitin-proteasome system. The synthesized compounds reduced mHtt levels in HD patient fibroblasts and appear to be promising candidates for the development of a treatment for HD.

Angewandte Chemie, International Edition 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 C10H12O5, COA of Formula: C14H12N2S.

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

Otsuka, Shinya published the artcilePalladium-Catalyzed Insertion of Isocyanides into the C-S Bonds of Heteroaryl Sulfides, Category: thiazole, the publication is Angewandte Chemie, International Edition (2018), 57(22), 6653-6657, database is CAplus and MEDLINE.

Insertion of tert-Bu isocyanide into the C(sp²)-S bonds of heteroaryl sulfides is catalyzed by a palladium diphosphine complex. Thioimidates generated through this reaction could be readily hydrolyzed under acidic conditions to yield the corresponding thioesters, which are of synthetic use. This insertion is useful because starting heteroaryl sulfides were readily prepared by either conventional ways or through sulfur-specific extended Pummerer reactions.

Angewandte Chemie, International Edition 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, Category: thiazole.

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

Arisawa, Mieko published the artcileRhodium-catalyzed 2-methylthiolation reaction of thiazoles/oxazoles using 2-(methylthio)thiazole, Application of 2-(Methylthio)thiazole, the publication is Heterocycles (2015), 90(2), 939-949, database is CAplus.

RhH(PPh₃)₄ and 1,3-bis(dicyclohexyl)phosphinopropane (dcypp) catalyze the 2-methylthiolation of oxazoles and thiazoles I (R¹ = Me, Ph, pMeOC₆H₄, etc.; R² = H, Me, n-C₄H₉, etc; X = O, S) using 2-(methylthio)thiazole as a thiolating reagent. The methylthio transfer reaction is under equilibrium and various 2-methylthiolated thiazoles and oxazoles II were obtained in moderate to good yields by removing thiazole under refluxing o-dichlorobenzene.

Heterocycles 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, Application of 2-(Methylthio)thiazole.

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

Roeder, Liesa published the artcileFlow hydrodediazoniation of aromatic heterocycles, Formula: C7H5ClN2S, the publication is Molecules (2019), 24(10), 1996pp., database is CAplus and MEDLINE.

Continuous flow processing was applied for the rapid replacement of an aromatic amino group with a hydride. The approach was applied to a range of aromatic heterocycles RNH₂ (R = 1,3-benzoxazol-2-yl, 2-pyridyl, 4-cyano-1-phenyl-1H-1,2,3-triazol-5-yl, etc.) confirming the wide scope and substituent-tolerance of the processes. Flow equipment was utilized and the process optimized to overcome the problematically-unstable intermediates that have restricted yields in previous studies relying on batch procedures. Various common organic solvents were investigated as potential hydride sources. The approach has allowed key structures, such as amino-pyrazoles and aminopyridines to be deaminated in good yield using a purely organic-soluble system.

Molecules 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, Formula: C7H5ClN2S.

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