Day: November 21, 2022

Boutard, Nicolas published the artcileDiscovery and structure-activity relationships of N-aryl 6-aminoquinoxalines as potent PFKFB3 kinase inhibitors, COA of Formula: C14H18BNO2S, the publication is ChemMedChem (2019), 14(1), 169-181, database is CAplus and MEDLINE.

Energy and biomass production in cancer cells are largely supported by aerobic glycolysis in what is called the Warburg effect. The process is regulated by key enzymes, among which phosphofructokinase PFK-2 plays a significant role by producing fructose-2,6-biphosphate; the most potent activator of the glycolysis rate-limiting step performed by phosphofructokinase PFK-1. Herein, the synthesis, biol. evaluation and structure-activity relationship of novel inhibitors of 6-phosphofructo-2-kinase/fructose-2,6-biphosphatase 3 (PFKFB3), which is the ubiquitous and hypoxia-induced isoform of PFK-2, are reported. X-ray crystallog. and docking were instrumental in the design and optimization of a series of N-aryl 6-aminoquinoxalines. The most potent representative, N-(4-methanesulfonylpyridin-3-yl)-8-(3-methyl-1-benzothiophen-5-yl)quinoxalin-6-amine, displayed an IC₅₀ of 14 nM for the target and an IC₅₀ of 0.49 μM for fructose-2,6-biphosphate production in human colon carcinoma HCT116 cells. This work provides a new entry in the field of PFKFB3 inhibitors with potential for development in oncol.

ChemMedChem published new progress about 791614-90-9. 791614-90-9 belongs to thiazole, auxiliary class Boronate Esters,Boronic acid and ester,Boronic acid and ester, name is 2-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazole, and the molecular formula is C14H18BNO2S, COA of Formula: C14H18BNO2S.

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

Lei, Ying-jie published the artcileSynthesis of 2-(4-aminophenyl)-6-benzothiazoles derivatives in the presence of manganese(III) acetate, COA of Formula: C14H12N2S, the publication is Huaxue Yanjiu Yu Yingyong (2012), 24(10), 1596-1599, database is CAplus.

Several 4-nitrophenybenzothiazole intermediates were prepared by condensation reaction of 2-aminothiophenol and(substituted) 4-nitrobenzaldehyde in the presence of manganese(III) acetate and the procedure was shown to be mild and easy, which was followed with a reduction under the Pd/C catalyst to afford the desired amino derivatives and resulted in yields of 63-79%. The formation of the corresponding products was confirmed by IR, ¹HNMR and elemental anal.

Huaxue Yanjiu Yu Yingyong 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, COA of Formula: C14H12N2S.

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

Jana, Asim published the artcileI₂/DMSO mediated multicomponent reaction for the synthesis of 2-arylbenzo[d]imidazo[2,1-b]thiazole derivatives, HPLC of Formula: 95-24-9, the publication is Organic & Biomolecular Chemistry (2019), 17(21), 5316-5330, database is CAplus and MEDLINE.

Synthesis of a series of 2-arylbenzo[d]imidazo[2,1-b]thiazoles tethered with barbituric acid moiety was reported from the three component reaction of 2-aminobenzothiazoles, barbituric acids and terminal aryl acetylenes or aryl Me ketones in the presence of I₂ in DMSO medium. Both conventional and microwave heating conditions was used for this multicomponent reaction. The salient features of this methodol. are: (i) formation of one C-C and two C-N bonds in one-pot under metal-free oxidation followed by cyclization (ii) selective formation of the fused imidazole ring, (iii) wide substrate scope (iv) easy purification of the products (v) products having more than one pharmaceutically important motifs and (vi) gram scale synthesis possible.

Organic & Biomolecular 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, HPLC of Formula: 95-24-9.

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

Prasanna, Gutta Lakshmi published the artcileSynthesis and antibacterial activity of benzothiazole analogues, Safety of 2-(4-Aminophenyl)-6-methylbenzothiazole, the publication is Journal of Applicable Chemistry (Lumami, India) (2018), 7(6), 1558-1564, database is CAplus.

A series of novel benzothiazole fused derivatives I [R = Me, Cl, Br, I; R¹ = Me, OMe] was designed, synthesized and screened for their antibacterial activity against Escherichia coli (MTCC 40) (Gram-neg.) and Staphylococcus aureus (MTCC 96)(Gram-pos.) bacteria. Among them, derivative I [R = Cl; R¹ = Me] showed highest antibacterial activity against Gram-pos. and Gram-neg. bacteria.

Journal of Applicable Chemistry (Lumami, India) 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

Sharma, Neetesh Kumar published the artcileSynthesis and biological evaluation of 1-(6-chlorobenzo[d]thiazol-2-yl)-2-(disubstituted methylene)hydrazine derivatives, Name: 6-Chlorobenzothiazol-2-ylamine, the publication is Journal of Drug Delivery and Therapeutics (2019), 9(4-ASuppl.2), 561-572, database is CAplus.

Synthesis of a series of various 1-(6-chlorobenzo[d]thiazol-2-yl)-2-(disubstituted methylene)hydrazine derivatives (E/Z)-I [R¹ = Ph, Me; R² = Ph, Me, Et; R¹R² = -(CH₂)₅-], (E)-2-(6-chlorobenzo[d]thiazol-2-yl)-1-(7,7-dimethylbicyclo [2.2.1] heptan-2-ylidene) hydrazine and intermediates 6-chloro-2-amine-1,3-benzothiazole and 2-hydrazino-6-chloro-1,3-benzothiazole have been done. After spectral anal., antibacterial activity has been screened against S. aureus and E. coli.

Journal of Drug Delivery and Therapeutics 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 C8H10S, Name: 6-Chlorobenzothiazol-2-ylamine.

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

Wells, Geoffrey published the artcile4-Substituted 4-Hydroxycyclohexa-2,5-dien-1-ones with Selective Activities against Colon and Renal Cancer Cell Lines, COA of Formula: C14H12N2S, the publication is Journal of Medicinal Chemistry (2003), 46(4), 532-541, database is CAplus and MEDLINE.

The synthesis and antitumor evaluation of a series of new heteroaromatic- and aromatic-substituted hydroxycyclohexadienones (quinols), and their imine counterparts, are described. The quinols were synthesized via the addition of a lithiated aromatic moiety to a quinone ketal followed by deprotection. When the aromatic portion of the mol. is a fused heterobicyclic structure (e.g., benzothiazole derivative I), potent in vitro antitumor activity was observed in HCT 116 (GI₅₀ = 40 nM) and HT 29 (GI₅₀ = 380 nM) human colon as well in as MCF-7 and MDA 468 human breast cancer cell lines. When examined on the NCI Developmental Therapeutics Screening Program in vitro screen (60 human cancer cell lines), active compounds in this series consistently displayed a highly unusual pattern of selectivity; cytotoxicity (LC₅₀) was concentrated in certain colon and renal cell lines only. I also showed in vivo antitumor activity against human RXF 944XL renal xenografts in nude NMRI mice and is the focus of further study.

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 C18H26ClN3O, COA of Formula: C14H12N2S.

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

Karlsson, H. Jonas published the artcileSyntheses and DNA-binding studies of a series of unsymmetrical cyanine dyes: structural influence on the degree of minor groove binding to natural DNA, Application of 2-(4-Aminophenyl)-6-methylbenzothiazole, the publication is Bioorganic & Medicinal Chemistry (2004), 12(9), 2369-2384, database is CAplus and MEDLINE.

Twelve crescent-shaped unsym. dyes have been synthesized and their interactions with DNA have been investigated by spectroscopic methods. A new facile synthetic route to this type of cyanine dyes has been developed, involving the preparation of 6-substituted 2-thiomethyl-benzothiazoles in good yields. The new dyes are analogs to the minor groove binding unsym. cyanine dye, BEBO, recently reported by us. In this dye, the structure of the known intercalating cyanine dye BO was extended with a 6-methylbenzothiazole substituent. Herein we further investigate the role of the extending benzazole heterocycle, as well as of the pyridine or quinoline moiety of the cyanine chromophore, for the binding mode of these crescent-shaped dyes to calf thymus DNA. Flow LD and CD studies of the 12 dyes show that the extent of minor groove binding to mixed sequence DNA varies significantly between the dyes. We find that hydrophobicity and size are the crucial parameters for recognition of the minor groove. The relatively high fluorescence quantum yield of many of these cyanines bound to DNA, combined with their absorption at long wavelengths, may render them useful in biol. applications. In particular, two of the benzoxazole containing dyes BOXTO and 2-BOXTO show a high degree of minor groove binding and quantum yields of 0.52 and 0.32, resp., when bound to DNA.

Bioorganic & 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, Application of 2-(4-Aminophenyl)-6-methylbenzothiazole.

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

Ukrainets, I. V. published the artcileSynthesis, spectral characteristics and biological properties of 1-furfuryl-4-hydroxy-2-oxo-1,2,5,6,7,8-hexahydroquinoline-3-carboxylic acid anilides and heterylamides, Application In Synthesis of 92-36-4, the publication is Zhurnal Organichnoi ta Farmatsevtichnoi Khimii (2007), 5(1), 32-38, database is CAplus.

With the purpose of determination of regularities of their structure-antituberculosis activity relationship, the synthesis of 1-furfuryl-4-hydroxy-2-oxo-1,2,5,6,7,8-hexahydroquinoline-3-carboxylic acids N-R-amides has been carried out. The peculiarities of the NMR spectra of the compounds synthesized and the results of studying of their antimycobacterial activity are discussed.

Zhurnal Organichnoi ta Farmatsevtichnoi Khimii 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 C39H35N5O8, Application In Synthesis of 92-36-4.

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

Haj-Yehia, Abdullah I. published the artcileDetermination of aliphatic thiols by fluorometric high-performance liquid chromatography after precolumn derivatization with 2-(4-N-maleimidophenyl)-6-methylbenzothiazole, Safety of 2-(4-Aminophenyl)-6-methylbenzothiazole, the publication is Pharmaceutical Research (1995), 12(1), 155-60, database is CAplus and MEDLINE.

A sensitive, fluorometric high-performance liquid chromatog. method for the detection of aliphatic thiols, following pre-column derivatization with 2-(4-N-maleimidophenyl)-6-methylbenzothiazole, has been developed. The N-maleimide, the acid and the Me ester derivatives of the com. available 2-(4-aminophenyl)-6-methylbenzothiazole were synthesized and found to be equally effective for the precolumn derivatization procedure. The resulting fluorescent derivatives of aliphatic thiols were separated on a reversed-phase column (Ultrasphere-ODS) using 0.1% hexane-sulfonic acid in 10 mM potassium hydrogen phosphate:acetonitrile (65:35) as a mobile phase and were detected fluorometrically (excitation 320 nm; emission 405 nm). The method is highly sensitive (femtomole range) and is easily applied for determination of SH-containing drugs and endogenous thiols in biol. samples.

Pharmaceutical Research 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

Schmidt, Monika published the artcileBenzothiazolyl ureas are low micromolar and uncompetitive inhibitors of 17β-HSD10 with implications to Alzheimer’s disease treatment, Quality Control of 95-24-9, the publication is International Journal of Molecular Sciences (2020), 21(6), 2059, database is CAplus and MEDLINE.

Human 17β-hydroxysteroid dehydrogenase type 10 is a multifunctional protein involved in many enzymic and structural processes within mitochondria. This enzyme was suggested to be involved in several neurol. diseases, e.g., mental retardation, Parkinson’s disease, or Alzheimer’s disease, in which it was shown to interact with the amyloid-beta peptide. We prepared approx. 60 new compounds based on a benzothiazolyl scaffold and evaluated their inhibitory ability and mechanism of action. The most potent inhibitors contained 3-chloro and 4-hydroxy substitution on the Ph ring moiety, a small substituent at position 6 on the benzothiazole moiety, and the two moieties were connected via a urea linker (4at, 4bb, and 4bg). These compounds exhibited IC₅₀ values of 1-2μ and showed an uncompetitive mechanism of action with respect to the substrate, acetoacetyl-CoA. These uncompetitive benzothiazolyl inhibitors of 17β-hydroxysteroid dehydrogenase type 10 are promising compounds for potential drugs for neurodegenerative diseases that warrant further research and development.

International Journal of Molecular Sciences 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