Month: November 2022

Song, Xiaoxiao published the artcileHighly Stereoselective Palladium-Catalyzed [3+2] Cycloaddition of Vinyl Epoxides and N-Benzothiazolimines, Product Details of C7H5ClN2S, the publication is Asian Journal of Organic Chemistry (2019), 8(12), 2180-2183, database is CAplus.

An asym. [3+2] cycloaddition of racemic vinyl epoxides with N-benzothiazolimines was presented under Pd-catalysis. This transformation provided rapid access to highly functionalized oxazolidine scaffolds such as I [R = H, 4-Me, 5-Br, etc.; Ar = Ph, 1-naphthyl, 2-thienyl, etc.] in generally good yields along with high stereoselectivities (up to 99% ee, 8.5 : 1 d.r.) under mild conditions. The use of chiral BINAP ligand enabled this asym. transformation with a broad substrate tolerance.

Asian Journal of Organic 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 C16H12O, Product Details of C7H5ClN2S.

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

Polak, Jolanta published the artcileBioactive Properties of a Novel Antibacterial Dye Obtained from Laccase-Mediated Oxidation of 8-Anilino-1-naphthalenesulfonic Acid, Application of Ammonium 2,2′-(hydrazine-1,2-diylidene)bis(3-ethyl-2,3-dihydrobenzo[d]thiazole-6-sulfonate), the publication is Molecules (2022), 27(2), 487, database is CAplus and MEDLINE.

Fungal laccase obtained from a Cerrena unicolor strain was used as an effective biocatalyst for the transformation of 8-anilino-1-naphthalenesulfonic acid into a green-colored antibacterial compound, which can be considered as both an antimicrobial agent and a textile dye, simultaneously. The process of biosynthesis was performed in buffered solutions containing methanol as a co-solvent, allowing better solubilization of substrate. The transformation process was optimized in terms of the buffer pH value, laccase activity, and concentrations of the substrate and co-solvent. The crude product obtained exhibited low cytotoxicity, antibacterial properties against Staphylococcus aureus and Staphylococcus epidermidis, and antioxidant properties. Moreover, the synthesized green-colored compound proved non-allergenic and demonstrated a high efficiency of dyeing wool fibers.

Molecules 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, Application of 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

Liebig, H. published the artcileExperimental results with systematically synthesized substances for antiviral chemotherapy. 4. Role of physical binding in the synthesis of antiviral chemotherapeutics and its influence on potential mutagenic effects, Application of 4-(Naphthalen-1-yl)thiazol-2-amine, the publication is Arzneimittel-Forschung (1975), 25(11), 1716-22, database is CAplus and MEDLINE.

Of 13 antiviral substances containing specific hydrogen bridge linkage systems of the classes of 2-substituted 4-phenylthiazoles, 4-phenylimidazoles, and 1,3-indandiones tested for mutagenicity in the host-mediated assay, in bone marrow of rats, in spermatogonia of mice, and in the micronucleus test in rats, only N1-methyl-N2-(4-phenylthiazol-2-yl)urea (I) [52968-02-2] was mutagenic. Thus, the antiviral effectiveness of these substances was not caused by a chem. change in the coding system but by formation of phys. linkages like H bridge complexes with coding structures.

Arzneimittel-Forschung 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, Application of 4-(Naphthalen-1-yl)thiazol-2-amine.

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

Liskovykh, Mikhail published the artcileA novel assay to screen siRNA libraries identifies protein kinases required for chromosome transmission, Quality Control of 95-24-9, the publication is Genome Research (2019), 29(10), 1719-1732, database is CAplus and MEDLINE.

One of the hallmarks of cancer is chromosome instability (CIN), which leads to aneuploidy, translocations, and other chromosome aberrations. However, in the vast majority of human tumors the mol. basis of CIN remains unknown, partly because not all genes controlling chromosome transmission have yet been identified. To address this question, we developed an exptl. high-throughput imaging (HTI) siRNA assay that allows the identification of novel CIN genes. Our method uses a human artificial chromosome (HAC) expressing the GFP transgene. When this assay was applied to screen an siRNA library of protein kinases, we identified PINK1, TRIO, IRAK1, PNCK, and TAOK1 as potential novel genes whose knockdown induces various mitotic abnormalities and results in chromosome loss. The HAC-based assay can be applied for screening different siRNA libraries (cell cycle regulation, DNA damage response, epigenetics, and transcription factors) to identify addnl. genes involved in CIN. Identification of the complete spectrum of CIN genes will reveal new insights into mechanisms of chromosome segregation and may expedite the development of novel therapeutic strategies to target the CIN phenotype in cancer cells.

Genome 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, Quality Control of 95-24-9.

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

Gundala, Trivikram Reddy published the artcileCitric Acid-catalyzed Synthesis of 2,4-Disubstituted Thiazoles from Ketones via C-Br, C-S, and C-N Bond Formations in One Pot: A Green Approach, Safety of 4-(Naphthalen-1-yl)thiazol-2-amine, the publication is Journal of the Chinese Chemical Society (Weinheim, Germany) (2017), 64(12), 1408-1416, database is CAplus.

An improved and greener protocol has been developed for the synthesis of 2,4-disubstituted thiazoles via C-Br, C-S, and, C-N bond formations in a single step from readily available ketones, N-bromosuccinimide (NBS), and thiourea catalyzed by citric acid in a mixture of ethanol and water (3:1) under reflux conditions. This method has the advantages of freedom from the isolation of lachrymatory α-bromoketones, ease of carrying out, cleaner reaction profile, broad substrate scope, freedom from chromatog. purification, and suitability for large-scale synthesis.

Journal of the Chinese Chemical Society (Weinheim, Germany) 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

Jarrige, Lucie published the artcileChiral phosphoric acid-catalyzed enantioselective construction of structurally diverse benzothiazolopyrimidines, Related Products of thiazole, the publication is Chemical Science (2019), 10(13), 3765-3769, database is CAplus and MEDLINE.

A highly efficient catalytic enantioselective [4+2] cycloaddition was developed between 2-benzothiazolimines and enecarbamates. A wide range of benzothiazolopyrimidines bearing three contiguous stereogenic centers was obtained in high to excellent yields and with excellent diastereo- and enantioselectivities (d.r. > 98 : 2 and up to >99% ee). Furthermore, this chiral phosphoric acid-catalyzed strategy was scalable and enabled access to a new class of optically pure Lewis base isothiourea derivatives

Chemical Science 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, Related Products of thiazole.

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

Goya-Jorge, Elizabeth published the artcilePredictive modeling of aryl hydrocarbon receptor (AhR) agonism, Safety of 2-(4-Aminophenyl)-6-methylbenzothiazole, the publication is Chemosphere (2020), 127068, database is CAplus and MEDLINE.

The aryl hydrocarbon receptor (AhR) plays a key role in the regulation of gene expression in metabolic machinery and detoxification systems. In the recent years, this receptor has attracted interest as a therapeutic target for immunol., oncogenic and inflammatory conditions. In the present report, in silico and in vitro approaches were combined to study the activation of the AhR. To this end, a large database of chem. compounds with known AhR agonistic activity was employed to build 5 classifiers based on the Adaboost (AdB), Gradient Boosting (GB), Random Forest (RF), Multilayer Perceptron (MLP) and Support Vector Machine (SVM) algorithms, resp. The built classifiers were examined, following a 10-fold external validation procedure, demonstrating adequate robustness and predictivity. These models were integrated into a majority vote based ensemble, subsequently used to screen an inhouse library of compounds from which 40 compounds were selected for prospective in vitro exptl. validation. The general correspondence between the ensemble predictions and the in vitro results suggests that the constructed ensemble may be useful in predicting the AhR agonistic activity, both in a toxicol. and pharmacol. context. A preliminary structure-activity anal. of the evaluated compounds revealed that all structures bearing a benzothiazole moiety induced AhR expression while diverse activity profiles were exhibited by phenolic derivatives

Chemosphere 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, Safety of 2-(4-Aminophenyl)-6-methylbenzothiazole.

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

Drapier, Thomas published the artcileEnhancing Action of Positive Allosteric Modulators through the Design of Dimeric Compounds, Safety of 4-Cyclopropyl-7-fluoro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine 1,1-dioxide, the publication is Journal of Medicinal Chemistry (2018), 61(12), 5279-5291, database is CAplus and MEDLINE.

The present study describes the identification of highly potent dimeric 1,2,4-benzothiadiazine 1,1-dioxide (BTD)-type pos. allosteric modulators of the AMPA receptors (AMPApams) obtained by linking two monomeric BTD scaffolds through their resp. 6-positions. Using previous X-ray data from monomeric BTDs cocrystd. with the GluA2 ligand-binding domain (LBD), a mol. modeling approach was performed to predict the preferred dimeric combinations. Two 6,6-ethylene-linked dimeric BTD compounds (16 and 22) were prepared and evaluated as AMPApams on HEK293 cells expressing GluA2_o(Q) (calcium flux experiment). These compounds were found to be about 10,000 times more potent than their resp. monomers, the most active dimeric compound being the bis-4-cyclopropyl-substituted compound 22 [6,6′-(ethane-1,2-diyl)bis(4-cyclopropyl-3,4-dihydro-2H-1,2,4-benzothiadiazine 1,1-dioxide], with an EC₅₀ value of 1.4 nM. As a proof of concept, the bis-4-methyl-substituted dimeric compound 16 (EC₅₀ = 13 nM) was successfully cocrystd. with the GluA2_o-LBD and was found to occupy the two BTD binding sites at the LBD dimer interface.

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, Safety of 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

Campos, Ludmila E. published the artcileSearching new structural scaffolds for BRAF inhibitors. An integrative study using theoretical and experimental techniques, COA of Formula: C6H8N2O2S, the publication is Bioorganic Chemistry (2019), 103125, database is CAplus and MEDLINE.

The identification of the V600E activating mutation in the protein kinase BRAF in around 50% of melanoma patients has driven the development of highly potent small inhibitors (BRAFi) of the mutated protein. To date, Dabrafenib and Vemurafenib, two specific BRAFi, have been clin. approved for the treatment of metastatic melanoma. Unfortunately, after the initial response, tumors become resistant and patients develop a progressive and lethal disease, making imperative the development of new therapeutic options. The main objective of this work was to find new BRAF inhibitors with different structural scaffolds than those of the known inhibitors. Our study was carried out in different stages; in the first step we performed a virtual screening that allowed us to identify potential new inhibitors. In the second step, we synthesized and tested the inhibitory activity of the novel compounds founded. Finally, we conducted a mol. modeling study that allowed us to understand interactions at the mol. level that stabilize the formation of the different mol. complexes. Our theor. and exptl. study allowed the identification of four new structural scaffolds, which could be used as starting structures for the design and development of new inhibitors of BRAF. Our exptl. data indicate that the most active compounds reduced significantly ERK1/2 phosphorylation, a measure of BRAF inhibition, and cell viability. Thus, from our theor. and exptl. results, we propose new substituted hydroxynaphthalenecarboxamides, N-(hetero)aryl-piperazinylhydroxyalkylphenylcarbamates, substituted piperazinylethanols and substituted piperazinylpropandiols as initial structures for the development of new inhibitors for BRAF. Moreover, by performing QTAIM anal., we are able to describe in detail the mol. interactions that stabilize the different Ligand-Receptor complexes. Such anal. indicates which portion of the different mols. must be changed in order to obtain an increase in the binding affinity of these new ligands.

Bioorganic Chemistry published new progress about 64987-16-2. 64987-16-2 belongs to thiazole, auxiliary class Thiazole,Amine,Ester, name is Methyl 2-(2-aminothiazol-4-yl)acetate, and the molecular formula is C6H8N2O2S, COA of Formula: C6H8N2O2S.

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

Moloney, Gerard P. published the artcileSynthesis and serotonergic activity of variously substituted (3-amido)phenylpiperazine derivatives and benzothiophene-4-piperazine derivatives: novel antagonists for the vascular 5-HT_1B receptor, Recommanded Product: 2-(4-Aminophenyl)-6-methylbenzothiazole, the publication is European Journal of Medicinal Chemistry (2004), 39(4), 305-321, database is CAplus and MEDLINE.

The synthesis and vascular 5-HT_1B receptor activity of a novel series of substituted 3-amido phenylpiperazine and 4-(4-methyl-1-piperazinyl)-1-benzo[b]thiophene derivatives is described. Modifications to the amido linked sidechains of the 3-amidophenyl piperazine derivatives and to the 2-side-chain of the 1-benzo[b]thiophene derivatives have been explored. Several compounds were identified which exhibited affinity at the vascular 5-HT_1B receptor of pK_B > 7.0. From the 3-amidophenyl-piperazine series, N-[5-(4-chlorophenyl)-2-thiazolyl]-3-(4-methyl-1-piperazinyl)benzamide (I) and from the benzo[b]thiophene-4-piperazine series N-(2-ethylphenyl)-4-(4-methyl-1-piperazinyl)benzo[b]thiophene-2-carboxamide (II) were identified as a highly potent, silent (as judged by the inability of angiotensin II to unmask 5-HT_1B receptor mediated agonist activity in the rabbit femoral artery) and competitive vascular 5-HT_1B receptor antagonist. The affinity of compounds from these two series of compounds for the vascular 5-HT_1B receptor is discussed as well as a proposed mode of binding to the receptor pharmacophore.

European 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 C14H12N2S, Recommanded Product: 2-(4-Aminophenyl)-6-methylbenzothiazole.

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