Day: November 21, 2022

Dogan, Kubra published the artcileNovel Fluorescent Azacyanine Compounds: Improved Synthesis and Optical Properties, Synthetic Route of 95-24-9, the publication is ACS Omega (2020), 5(36), 22874-22882, database is CAplus and MEDLINE.

Benzothiazoles are known to possess a number of biol. activities and therefore are considered to be an important scaffold in the design and synthesis of pharmacophores. In this study, an improved synthesis method for novel fluorescent benzothiazole-based cyclic azacyanine (CAC) dyes bearing different electron-donating/withdrawing groups on their scaffold is presented. The improved method enabled us to increase the synthesis yield for the previously reported CACs. More importantly, it allowed us to synthesize new CAC dyes that were not synthesizable with the previously reported method. The synthesized dyes were characterized by ¹H and ¹³C NMR spectroscopy, elemental anal., and mass spectrometry and their optical (absorption and fluorescence) properties were investigated. All of the synthesized CACs were found to be displaying strong absorption within the range of 387-407 nm. The spectral shifts observed in the absorption and fluorescence measurements suggested that the spectroscopic and optical properties of CACs can be directly modulated by the nature of the electron-donating/withdrawing substituents. The fluorescence quantum yields (QYs) of the unsubstituted (parent CAC) and substituted CACs were also measured and compared. The fluorescence QY of CACs with electron-donating substituents (methoxy or ethoxy) was found to be at least four times higher than that of the parent CAC with no substitutions.

ACS Omega 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, Synthetic Route of 95-24-9.

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

Fonseca, I. published the artcileUndervalued Atlantic brown seaweed species (Cystoseira abies-marina and Zonaria tournefortii): influence of treatment on their nutritional and bioactive potential and bioaccessibility, Quality Control of 30931-67-0, the publication is European Food Research and Technology (2021), 247(1), 221-232, database is CAplus.

The brown seaweed species Cystoseira abies-marina and Zonaria tournefortii are abundant Atlantic resources that remain undervalued. This results from an insufficient knowledge of their nutrients’ and bioactive potential. There is also uncertainty regarding the adequate culinary treatment of these seaweeds prior to their consumption. Thus, the current study evaluated the composition, bioactivity, and bioaccessibility of target compounds and bioactivities of these two species as a function of two treatments, simple rehydration and steaming, in comparison to sun-dried seaweed. The proportion of SFA, MUFA, and PUFA differed between species. C. abies-marina was richer in PUFA (30-31% vs 20-21%) and Z. tournefortii was richer in SFA (53-57% vs 46-47%). Main contributors to ω3 PUFA content were different in each species: alpha-linolenic acid in C. abies-marina, 4.5-5.1%, and eicosapentaenoic acid in Z. tournefortii, 5.8-6.7%. The sum of Mg and Ca contents in Z. tournefortii was two-fold the same sum in the other species. Furthermore, rehydration led to an elemental concentration reduction in most instances. The As content in C. abies-marina was very high, ranging between 295 ± 5 mg/kg dw and 369 ± 2 mg/kg dw, in rehydrated and steam-cooked seaweed, resp. While aqueous extracts of C. abies-marina had the highest phenolic contents, 620-1280 mg GAE/100 g dw, aqueous extracts of Z. tournefortii contained 170-280 mg GAE/100 g dw. Regarding bioaccessibility, Mg, K, Ca, As, and Cd showed relatively high bioaccessibility levels and it was shown that only a limited part of the original antioxidant activity in both species is bioaccessible.

European Food Research and Technology 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, Quality Control of 30931-67-0.

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

Zhang, Zhen published the artcileSynthesis and biological evaluation of novel indoleamide derivatives as antioxidative and antitumor agents, Formula: C7H5ClN2S, the publication is Journal of Heterocyclic Chemistry (2020), 57(3), 1165-1172, database is CAplus.

Novel indole amide derivatives I [R = pyrazin-2-amino, (2-methoxy-1-methyl-2-oxo-ethyl)amino, (2-oxoazepan-3-yl)amino, etc.] were successfully synthesized and characterized by ¹H NMR, ¹³C NMR, IR, MS, and elemental anal., and their mol. formulas were C₁₄H₁₀N₆O, C₁₃H₁₀N₄O, C₁₆H₁₃N₃O₂, C₁₉H₁₄N₂O₂, C₁₆H₁₁N₃OS, C₁₅H₁₃N₃O, C₁₂H₉N₅O, C₁₆H₁₀ClN₃OS, C₁₅H₁₇N₃O₂ and C₁₃H₁₄N₂O₃, resp. The primary biol. activities of these compounds I were evaluated in-vitro by the DPPH assay, H₂O₂ induced oxidative stress injury assay and cytotoxicity assay. The results indicated that compounds I [R = imidazo[4,5-d]pyridazin-4-amino, pyrazin-2-amino, 7-hydroxynaphthalen-1-amino, 5H-1,2,4-triazin-4-amino, (2-oxoazepan-3-yl)amino] exhibited DPPH·scavenging ability, while I [R = 2-carbamoylanilino, 7-hydroxynaphthalen-1-amino, 1,3-benzothiazol-2-amino, 6-chloro-1,3-benzothiazol-2-amino] showed potent growth-inhibitory activities against various human tumor cells, including MDA-MB-231, Hela, A549 and HT29. Interestingly, compound I [R = 7-hydroxynaphthalen-1-amino] showed potent scavenging effects on the DPPH radical and possessed protective effect on H₂O₂-induced oxidative stress injury in human neuroblastoma SH-SY5Y cells at low concentrations; however, I [R = 7-hydroxynaphthalen-1-amino] exhibited significant toxicity against four human tumor cells at a higher concentration in all treatments, and the range of IC₅₀ value was 7.91 to 13.35μM.

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 C19H17N2NaO4S, Formula: C7H5ClN2S.

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

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