Tag: M.W=150-200

Dai, Fang published the artcileA promising redox cycle-based strategy for designing a catechol-type diphenylbutadiene as a potent prooxidative anti-melanoma agent, Safety of 2,3-Dimethoxybenzaldehyde, the main research area is melanoma antitumor catechol type diphenylbutadiene oxidative stress ROS; tyrosinase NQO1; Hydrogen peroxide; NQO1; Prooxidant; Redox; Tyrosinase.

Developing anti-melanoma agents with increased activity and specificity is highly desirable due to the increasing incidence, highly metastatic malignancy, and high mortality rate of melanoma. Abnormal redox characteristics such as higher levels of tyrosinase, NAD(P)H: quinone oxidoreductase-1 (NQO1) and reactive oxygen species (ROS) observed in melanoma cells than in other cancer cells and normal cells illustrate their redox vulnerability and have opened a window for developing prooxidative anti-melanoma agents (PAAs) to target the vulnerability. However, how to design PAAs which promote selectively the ROS accumulation in melanoma cells remains a challenge. This work describes a promising redox cycle-based strategy for designing a catechol-type diphenylbutadiene as such type of PAA. This mol. is capable of constructing an efficient catalytic redox cycle with tyrosinase and NQO1 in melanoma B16F1 cells to induce selectively the ROS (mainly including hydrogen peroxide, H2O2) accumulation in the cells, resulting in highly selective suppression of melanoma B16F1 cells over tyrosinase-deficient HeLa and normal L-02 cells.

Free Radical Biology & Medicine published new progress about Antitumor agents. 86-51-1 belongs to class isoquinoline, name is 2,3-Dimethoxybenzaldehyde, and the molecular formula is C9H10O3, Safety of 2,3-Dimethoxybenzaldehyde.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

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

Chen, Qian published the artcileDesign and synthesis of novel nordihydroguaiaretic acid (NDGA) analogues as potential FGFR1 kinase inhibitors with anti-gastric activity and chemosensitizing effect, Application In Synthesis of 86-51-1, the main research area is gastric cancer FGFR1 NDGA growth survival migration; chemosensitizing effect; fibroblast growth factor receptor-1 inhibitor; gastric cancer; nordihydroguaiaretic acid analogues; synthesis.

Aberrant fibroblast growth factor receptor-1 (FGFR1), a key driver promoting gastric cancer (GC) progression and chemo-resistance, has been increasingly recognized as a potential therapeutic target in GC. Hereon, we designed and synthesized a series of asym. analogs using Af23 and NDGA as lead compounds by retaining the basic structural framework (bisaryl-1,4-dien-3-one) and the unilateral active functional groups (3,4-dihydroxyl). Thereinto, Y14 showed considerable inhibitory activity against FGFR1. Next, pharmacol. experiments showed that Y14 could significantly inhibit the phosphorylation of FGFR1 and its downstream kinase AKT and ERK, thus inhibiting the growth, survival, and migration of gastric cancer cells. Furthermore, compared with 5-FU treatment alone, the combination of Y14 and 5-FU significantly reduced the phosphorylation level of FGFR1, and enhanced the anti-cancer effect by inhibiting the viability and colony formation in two gastric cancer cell lines. These results confirmed that Y14 exerted anti-gastric activity and chemosensitizing effect by inhibiting FGFR1 phosphorylation and its downstream signaling pathway in vitro. This work also provides evidence that Y14, an effective FGFR1 inhibitor, could be used alone or in combination with chemotherapy to treat gastric cancer in the future.

Frontiers in Pharmacology published new progress about Antitumor agents. 86-51-1 belongs to class isoquinoline, name is 2,3-Dimethoxybenzaldehyde, and the molecular formula is C9H10O3, Application In Synthesis of 86-51-1.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Hosseinzadeh, Leila published the artcileSynthesis of 4-phenyl-4,5-dihydropyranopyrazolone derivatives with activated potassium carbonate: evaluation of anticancer activity on cancer cell lines and apoptosis mechanism, Related Products of isoquinoline, the main research area is phenyl dihydropyranopyrazolone derivative potassium carbonate apoptosis anticancer activity.

A green and efficient one-pot, four-component synthesis of 4-phenyl-4,5-dihydropyranopyrazolone derivatives 5a-5l is described in ethanol-water with activated potassium carbonate and evaluation of anticancer activity on cancer cell lines and apoptosis mechanism is also investigated. This method provides several advantages such as environmental friendliness, shorter reaction time, excellent yields, and simple workup procedure. The in vitro cytotoxic activity of the synthesized compounds was investigated against cancer cell lines (PC-3, MCF-7, and A-2780) in comparison with doxorubicin, a well-known anticancer drug, using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-tetrazolium bromide colorimetric assay. Also apoptosis studies were investigated by caspase-3 and caspase-9 enzymes and mitochondrial membrane potential. Our compounds showed acceptable and moderate cytotoxicity compared with doxorubicin in the studied cell lines. The compounds 5g in PC3 cell line (half maximal inhibitory concentration (IC50 = 104 μM)), 5g and 5i in MCF7 cell line (IC50 = 23 and 87 μM, resp.), and 5g-5i in A2780 cell line (IC50 = 60, 50, and 31 μM, resp.) showed the best results close to the control drug doxorubicin. The compound 5h showed significant result in the activation of caspase-3 and caspase-9 enzymes in comparison with the control. Only the 5g in MCF7 cells and the 5g-5i derivatives in A2780 cells caused increased mitochondrial membrane potential compared to the control group.

Journal of Reports in Pharmaceutical Sciences published new progress about Antitumor agents. 86-51-1 belongs to class isoquinoline, name is 2,3-Dimethoxybenzaldehyde, and the molecular formula is C9H10O3, Related Products of isoquinoline.

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

Pereira, Daniela published the artcileDesign and synthesis of new inhibitors of p53-MDM2 interaction with a chalcone scaffold, Related Products of isoquinoline, the main research area is chalcone derivative anticancer agent p53 MDM2 interaction docking cancer.

The virtual screening of a library of chalcone derivatives led us to the identification of potential new MDM2 ligands. The chalcones with the best docking scores obeying the Lipinski rule of five were subsequently prepared by base-catalyzed aldol reactions. The activity of these compounds as inhibitors of p53-MDM2 interaction was investigated using a yeast-based screening assay. Using this approach two chalcones (3 and 4) were identified as putative small mol. inhibitors of p53-MDM2 interaction. The activity of both chalcones was further investigated in a panel of human tumor cells. Chalcones 3 and 4 revealed a pronounced tumor cell growth inhibitory effect on tumor cell lines. Addnl., chalcone 4 caused alterations in the cell cycle profile, induced apoptosis and increased the levels of p53, p21 and PUMA proteins in NCI-H460 cells. Computational docking studies allowed to predict that, like nutlin-3A (a well-known small-mol. inhibitor of p53-MDM2 interaction), chalcones 3 and 4 bind to the p53-binding site of MDM2. The results here presented will be valuable for the structure-based design of novel and potent p53-MDM2 inhibitors.

Arabian Journal of Chemistry published new progress about Antitumor agents. 86-51-1 belongs to class isoquinoline, name is 2,3-Dimethoxybenzaldehyde, and the molecular formula is C9H10O3, Related Products of isoquinoline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem