Category: 104-01-8

Luo, Guoshun published the artcile3,9-di-O-substituted coumestrols incorporating basic amine side chains act as novel apoptosis inducers with improved pharmacological selectivity, COA of Formula: C9H10O3, the main research area is neoplasm antitumor coumestrol pharmacokinetics; Apoptosis; Cell cycle; Coumestrol; Estrogenic activity; Tubulin polymerization inhibitor.

There is much interest in the use of phytoestrogens such as coumestrol in breast cancer intervention due to their antiestrogenic activity and multiple modes of tumor cell death. However, the clear beneficial effects of naturally occurring estrogen mimetic coumestrol remain controversial due to exptl. evidence that it has been shown to stimulate MCF-7 cell proliferation via agonist effect on estrogen receptor at low concentration Herein, to disconnect the ER interaction and apoptosis-specific mechanism of coumestrol, various 3, 9-di-O-substituted coumestrols (7a-7e) and their furan ring-opened analogs (5a-5e) were synthesized and assessed for antiproliferative properties. Attachment of a dimethylamine-containing side chain to 3-O of coumestrol led to the most promising compound 7e (I) with improved antiproliferative activity (1.7-fold increase) against MCF-7 cells, decreased estrogen activity (>20 times weaker ERα binder) and a novel action to induce apoptosis. Mechanistic studies revealed that I is a tubulin polymerization inhibitor, which could arrest cell cycle at G2/M phase and induce apoptosis along with the decrease of mitochondrial membrane potential. In summary, such subtle modifications to the 3, 9-di-hydroxyl groups of coumestrol allow the generation of a novel apoptosis inducer with distinct pharmacol. properties, providing an excellent starting point to future development of novel tumor-vascular disrupting agents targeting tubulin.

Bioorganic Chemistry published new progress about Antitumor agents. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, COA of Formula: C9H10O3.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Yang, Kun published the artcileSynthesis, mitochondrial localization of fluorescent derivatives of cinnamamide as anticancer agents, COA of Formula: C9H10O3, the main research area is cinnamamide preparation anticancer fluorescent mitochondrial localization human; Cinnamamide; Cytotoxicity; Fluorescent image; Targeting mitochondria; Thia-Michael addition; Uptake.

The mitochondria-targeted derivatives, e.g., I were designed by the incorporation of cinnamamides into a fluorophore carrier of coumarin-3-carboxamide with a 1:1 stoichiometry. Using the amide linkers, twenty-one compounds were synthesized and the cytotoxicity against a panel of cancer cells (MCF-7, Hela, HepG2, HL-60) was tested. In particular, compound I displayed the potent cytotoxicity toward HL-60 leukemia cells, which could quickly and efficiently entry into HL-60 cells and specifically localize within mitochondria. And compound I preferred enrichment in HL-60 cells than in PBMC normal cells, accounting for the higher toxicity to cancer cells than to normal cells. Moreover, the dissipations of mitochondrial membrane potential and enhancement of cellular ROS level were also preceded upon compound I treatment, leading to cell cycle arrest and apoptosis/necrosis in HL-60 cells. Besides, acted as a Michael acceptor, compound I initiated a thia-Michael addition reaction toward cysteamine (1:2 stoichiometry), detecting by the UV-Vis spectrum and HRMS anal. This could result in the blue emission of compound I in mitochondria after the procedure of cell fixation, owing to the formation of covalent bond with mitochondrial thiols. This study reported compound I might be useful for the further development into a mitochondria-targeted anti-leukemia agent and the Michael acceptor might be a versatile functional group.

European Journal of Medicinal Chemistry published new progress about Antitumor agents. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, COA of Formula: C9H10O3.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Yang, Lifang published the artcileDesign, synthesis and biological evaluation of a series of new resveratrol analogues as potential anti-cancer agents, SDS of cas: 104-01-8, the main research area is benzeneacetic acid benzaldehyde Perkin condensation reaction; diphenylpropenoic acid preparation antitumor SAR apoptosis mol docking; anti-cancer; molecular docking; resveratrol; synthesis of resveratrol analogues; tubulin.

A series of novel resveratrol derivatives I [R1 = 3,4-Cl2, 2-OCF3O, 2-NO2-5-Cl, etc; R2 = 3,4,5-(MeO)3, 4-MeO, 3,5-Me2] were designed, synthesized and evaluated as anti-cancer agents. Most of compounds I showed significant anti-proliferative activities against three human cancer cell lines (HepG2, A549 and Hela). Among these compounds, compound I [R1 = 2-Cl-5-CF3, R2 = 4-MeO (II)] displayed the most potent inhibitory activity and showed low cytotoxic activity. Cell apoptosis and cell cycle assays demonstrated that compound II significantly induced apoptosis (p < 0.001) and arrested cell cycle at S phase. Immunofluorescence microscopy anal. showed compound II disrupted the tubulin network. Docking simulations supported the pharmacol. results of compound II. It was believed that this work was very useful for designing a new series of tubulin inhibitors. Royal Society Open Science published new progress about Antitumor agents. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, SDS of cas: 104-01-8.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

O’Boyle, Niamh M. published the artcileSynthesis and evaluation of antiproliferative microtubule-destabilising combretastatin A-4 piperazine conjugates, Quality Control of 104-01-8, the main research area is piperazine conjugate preparation antitumor microtubule human SAR docking cytotoxicity.

Design, synthesis, biochem. evaluation and mol. modeling studies were described for the series of analogs of the microtubule-destabilizing agent, combretastatin A-4 (CA-4) I [R1 = H, OH, OMe, NO2, F; R2 = OH, OMe; R3 = OH, piperazin-1-yl, 1,4-diazepan-1-yl, etc.] and II [R4 = H, OH; R5 = OH, piperazin-1-yl, 4-phenylpiperazin-1-yl, etc.] contain the CA-4 core structure with modifications to the stilbene linking group, and were predominantly piperazine derivatives Synthesis was achieved in a two-step process by firstly obtaining the acrylic acid via a Perkin reaction using microwave enhanced synthesis, followed by coupling using either DCC or Mukaiyama’s reagent. All target compounds I and II were screened for antiproliferative activity in MCF-7 breast cancer cells, among them compounds, I [R1 = OH; R2 = OMe, R3 = 4-phenylpiperazin-1-yl] displayed potent antiproliferative activity (IC50 = 190 nM). Two amino-containing derivatives, I [R1 = NH2; R2 = OMe; R3 = 4-benzylpiperazin-1-yl, 4-(p-tolyl)piperazin-1-yl] were the most potent with IC50 values of 130 nM and 83 nM resp. Representative compounds were shown to depolymerize tubulin, induce G2/M arrest and apoptosis in MCF-7 cells but not peripheral blood mononuclear cells and induce cleavage of the DNA repair enzyme poly ADP ribose polymerase (PARP) in MCF-7 cells. Modeling studies predicted that the compounds I and II bind to tubulin within the colchicine-binding site.

Organic & Biomolecular Chemistry published new progress about Antitumor agents. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Quality Control of 104-01-8.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Bhukya, Balakishan published the artcileBrevifoliol ester induces apoptosis in prostate cancer cells by activation of caspase pathway, SDS of cas: 104-01-8, the main research area is brevifoliol ester preparation apoptosis prostate cancer caspase; Ehrlich ascites carcinoma; acute oral toxicity; anticancer; apoptosis; brevifoliol analogues.

Prostate cancer is fourth most abundant cancer type around the globe. Brevifoliol, a rearranged taxoid from Taxus walllichiana needles has been derivatized as C5 esters using Steglich esterification reaction. Seventeen diverse analogs were evaluated against a panel of human cancer cell lines by MTT assay. Among these, two of the semi-synthetic analogs, i.e., 13 and 16 exhibited potent cytotoxicity, selectively against PC-3, prostate cancer cell lines. In cell cycle anal., analog 13 induced S and G2/M phase arrest and induced apoptosis by activating caspase-3. Compound 13 showed moderate efficacy in in-vivo Ehrlich ascites carcinoma in Swiss albino mice. Further, compound 13 was found to be safe in Swiss albino mice up to 1,000 mg/kg dose in acute oral toxicity. Brevifoliol ester 13 may further be optimized for better efficacy.

Chemical Biology & Drug Design published new progress about Antitumor agents. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, SDS of cas: 104-01-8.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Xu, Geng published the artcileMitochondria-Targeted Triphenylphosphonium Conjugated C-3 Modified Betulin: Synthesis, Antitumor Properties and Mechanism of Action, Product Details of C9H10O3, the main research area is triphenylphosphonium conjugated betulin apoptosis cell cycle arrest antitumor; antiproliferation; betulin; conjugation; drug discovery; mitochondria; structure-activity relationship; triphenylphosphonium.

A series of mitochondria-targeted triphenylphosphonium conjugated C-3 modified betulin were synthesized and evaluated against tumor cells. As a result, a new derivative 13 i, the conjugate of 3-O-(3′-acetylphenylacetate)-betulin with triphenylphosphonium, was identified as the one with the best anti-tumor effect. Conjugate 13 i significantly inhibited HCT116 cells with IC50 at 0.66 μM. While betulin, C-3 modified betulin, and the triphenylphosphonium moiety showed no inhibition of HCT116 cell proliferation at 20 μM. More importantly, 13 i exhibited a more cytotoxic effect against the tumor cell HCT116 than normal cell NCM460. Mode of action studies demonstrated that 13 i induced the G2/M phase cell cycle arrest and apoptosis in HCT116 cells through the mitochondrial pathway. Structure-activity relationship anal. revealed that integration of triphenylphosphonium moiety into the C-28 of betulin can greatly improve cytotoxicity. Appropriate modification on C-3 of the conjugate would improve the selectivity.

ChemMedChem published new progress about Antitumor agents. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Product Details of C9H10O3.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Vavaiya, Bhavinkumar published the artcileIn silico and in vitro antitubercular studies for nitrogen rich hybrids of homopiperazine-pyrimidine-pyrazole adducts, Category: isoquinoline, the main research area is Mycobacterium antitubercular nitrogen rich hybrid homopiperazine pyrimidine pyrazole.

Novel homopiperazine-pyrimidine-pyrazole hybrids (3a-j) were synthesized using Et 2-cyanoacetate and 4,6-dichloropyrimidine as starting materials by a multi-step process to afford Et 5-amino-1-(6-chloropyrimidin-4-yl)-1H-pyrazole-4-carboxylate in good yields using polar protic media. The intermediate 1, in two steps, chloroamine condensation followed by acid amine coupling, furnished the title compounds Et 5-amino-1-(6-(4-substituted aryl-1,4-diazepan-1-yl)pyrimidin-4-yl)-1H-pyrazole-4-carboxylate (3a-j). The synthesized compounds were docked in the crystal structure of Mycobacterium tuberculosis (PDB ID: 4TRO) to get insights into structural requirements for antitubercular activity. In vitro antitubercular activity against M. tuberculosis H37Rv strains showed that compounds 3a, 3d, 3e and 3g were found to be the most potent (Docking score: > -21; MIC = 1.6 μg/mL) among the synthesized mols. All the synthesized compounds showed acceptable drug-like properties which make them suitable for further lead modification using in silico design approaches.

Asian Journal of Chemistry published new progress about Crystal structure. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Category: isoquinoline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Chen, Jiangyan published the artcileApplication of UHPLC-Q-TOF MS based untargeted metabolomics reveals variation and correlation amongst different tissues of Eucommia ulmoides Oliver, Recommanded Product: 4-Methoxyphenylacetic acid, the main research area is metabolomic variation Eucommia liquid chromatog mass spectrometry.

The biol. function of Eucommia ulmoides Oliver (EU) is related to its metabolites. However, due to the complexity of distribution of metabolites in different tissues, currently, the comprehensive information anal. on metabolome of EU has been limited. In this study, we analyzed the components of leaves, seeds and barks of EU by using ultra high-performance liquid chromatog.-tandem time-of-flight mass spectrometer (UHPLC-Q-TOF MS) untargeted metabolomics before 2373 metabolites were identified in total. By using Principal Component Anal. (PCA), Partial Least Square Discriminant Anal. (PLS-DA) and other multivariate statistical anal. methods, there were 116 metabolites expressing differently in all samples. The result showed that the metabolic composition of leaves was similar to that of barks and there still existed significant differences amongst different tissues in HCA anal. Besides, the heatmap of differential metabolites also showed the higher concentrations of organic acids and derivatives, lipids and lipid-like mols. in seeds compared to leaves and barks. Furthermore, we detected 13,456 metabolites-metabolites correlations and determined 1098 metabolic pairs which resulted in significant correlation by Pearsons correlation anal. At last, all detected metabolites were annotated in KEGG and 966 of them had KEGG ID. After enrichment anal., 311 metabolites were mapped in 168 pathways and 26 of these pathways had apparent influence in the metabolic differences amongst different parts of EU. This work provides the first comprehensive metabolomic of EU, which will provide theor. basis for the separation and identification of medicinal activities of EU and potentially help advance studies in EU metabolic engineering.

Microchemical Journal published new progress about Eucommia ulmoides. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Recommanded Product: 4-Methoxyphenylacetic acid.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Ye, Zenghui published the artcilePIDA-Mediated Rearrangement for the Synthesis of Enantiopure Triazolopyridinones, Application In Synthesis of 104-01-8, the main research area is hydrazide diacetoxyiodobenzene tandem oxidative cyclization carbon migration rearrangement; triazolopyridinone preparation.

A tandem oxidative cyclization/1,2-carbon migration of hydrazides for the synthesis of otherwise inaccessible hindered or enantiopure triazolopyridinones has been developed. This protocol exhibits broad substrate scope and can be easily scaled up by continuous flow synthesis under mild conditions. Most importantly, this method demonstrates a rearrangement with retention of configuration and can be readily applied for the late-stage modification of carboxylic-acid-containing pharmaceuticals, amino acids, and natural products to access enantiopure triazolopyridinones.

Organic Letters published new progress about Flow. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Application In Synthesis of 104-01-8.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Era, Benedetta published the artcileLooking for new xanthine oxidase inhibitors: 3-Phenylcoumarins versus 2-phenylbenzofurans, Application of 4-Methoxyphenylacetic acid, the main research area is gout phenylcoumarin phenylbenzofuran xanthine oxidase inhibitor mol docking; 2-Phenylbenzofurans; 3-Phenylcoumarins; Xanthine oxidase inhibitors.

Overproduction of uric acid in the body leads to hyperuricemia, which is also closely related to gout. Uric acid production can be lowered by xanthine oxidase (XO) inhibitors. Inhibition of XO has also been proposed as a mechanism for improving cardiovascular health. Therefore, the search for new efficient XO inhibitors is an interesting topic in drug discovery. 3-Phenylcoumarins and 2-phenylbenzofurans are privileged scaffolds in medicinal chem. Their structural similarity makes them interesting mols. for a comparative study. Methoxy and nitro substituents were introduced in both scaffolds. The current study gives some insights into the synthesis and biol. activity of these mols. against this important target. For the best compound of the series, the 3-(4-methoxyphenyl)-6-nitrocoumarin (4), the IC50 value, type of inhibition, cytotoxicity on B16F10 cells and ADME theor. properties, were determined Docking studies were also performed in order to better understand the interactions of this mol. with the XO binding pocket. This work is a preliminary screening for further design and synthesis of new non-purinergic derivatives as potential compounds involved in the inflammatory suppression, specially related to gout.

International Journal of Biological Macromolecules published new progress about Gout. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Application of 4-Methoxyphenylacetic acid.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem