34716-73-9

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 100-83-4 meta-hydroxybenzaldehyde 
• 7440-44-0 pyrographite 
• 26638-97-1 5,6-dihydro-2H-pyran-2-one 
• 694-54-2 tetrahydro-2H-2-pyranol 

Downstream Products

• 154348-98-8 1-(3-tetrahydropyranyloxyphenyl)-2-nitroethanol 
• 220430-86-4 (E)-1-[2-Hydroxy-4-(tetrahydro-pyran-2-yloxy)-phenyl]-3-[3-(tetrahydro-pyran-2-yloxy)-phenyl]-propenone 
• 944250-15-1 C₅₆H₅₈O₄ 
• 1092706-09-6 C₂₂H₂₂O₆ 
• 105904-51-6 1-(furan-2-yl)-3-(3-hydroxyphenyl)prop-2-en-1-one 
• 93717-60-3 3-(3-hydroxyphenyl)-1-(pyridin-4-yl)prop-2-en-1-one 
• 292619-23-9 1-(5-methylfuran-2-yl)-3-(3-hydroxyphenyl)prop-2-en-1-one 
• 1446252-22-7 (E)-2-(3-(4-((tetrahydro-2H-pyran-2-yloxy)methyl)styryl)phenoxy)tetrahydro-2H-pyran 

Relevant academic research and scientific papers

Synthesis of novel 4-Boc-piperidone chalcones and evaluation of their cytotoxic activity against highly-metastatic cancer cells

In this study, six curcuminoids containing a tert-butoxycarbonyl (Boc) piperidone core were successfully synthesized, five of them are novel compounds reported here for the first time. These compounds were prepared through an aldolic condensation by adding tetrahydropyranyl-protected benzaldehydes or substituted benzaldehyde to a reaction mixture containing 4-Boc-piperidone and lithium hydroxide in an alcoholic solvent. A 44–94% yield was obtained supporting the developed methodology as a good strategy for the synthesis of 4-Boc-piperidone chalcones. Cytotoxic activity against LoVo and COLO 205 human colorectal cell lines was observed at GI50 values that range from 0.84 to 34.7 μg/mL, while in PC3 and 22RV1 human prostate cancer cell lines, GI50 values ranging from 17.1 to 22.9 μg/mL were obtained. Results from biochemical assays suggest that the cytotoxicity of the 4-Boc-piperidone chalcones can be linked to their ability to induce apoptosis, decrease the activity of NFκB and cellular proliferation. Our findings strongly support the potential of Boc-piperidone chalcones as novel cytotoxic agents against highly-metastatic cancer cells.

Discovery of Salidroside-Derivated Glycoside Analogues as Novel Angiogenesis Agents to Treat Diabetic Hind Limb Ischemia

Therapeutic angiogenesis is a potential therapeutic strategy for hind limb ischemia (HLI); however, currently, there are no small-molecule drugs capable of inducing it at the clinical level. Activating the hypoxia-inducible factor-1 (HIF-1) pathway in skeletal muscle induces the secretion of angiogenic factors and thus is an attractive therapeutic angiogenesis strategy. Using salidroside, a natural glycosidic compound as a lead, we performed a structure-activity relationship (SAR) study for developing a more effective and druggable angiogenesis agent. We found a novel glycoside scaffold compound (C-30) with better efficacy than salidroside in enhancing the accumulation of the HIF-1α protein and stimulating the paracrine functions of skeletal muscle cells. This in turn significantly increased the angiogenic potential of vascular endothelial and smooth muscle cells and, subsequently, induced the formation of mature, functional blood vessels in diabetic and nondiabetic HLI mice. Together, this study offers a novel, promising small-molecule-based therapeutic strategy for treating HLI.

PYRAZOLO[1,5-A][1,3,5]TRIAZINE-2-AMINE DERIVATIVE, PREPARATION METHOD THEREFOR AND MEDICAL USE THEREOF

Disclosed are a pyrazolo[1,5-a][1,3,5]triazine-2-amine derivative as shown in general formula (I), a preparation method therefor, a pharmaceutical composition containing the derivative and the use of same as a therapeutic agent, in particular the use thereof as an A2a receptor antagonist and the use thereof in the preparation of drugs for treating conditions or diseases improved by the inhibition of A2a receptors.

Hydroxy-substituted trans-cinnamoyl derivatives as multifunctional tools in the context of Alzheimer's disease

Alzheimer's disease (AD) is a multifactorial pathology that requires multifaceted agents able to address its peculiar nature. In recent years, a plethora of proteins and biochemical pathways has been proposed as possible targets to counteract neurotoxicity. Although the complex scenario is not completely elucidated, close relationships are emerging among some of these actors. In particular, increasing evidence has shown that aggregation of amyloid beta (Aβ), glycogen synthase kinase 3β (GSK-3β) and oxidative stress are strictly interconnected and their concomitant modulation may have a positive and synergic effect in contrasting AD-related impairments. We designed compound 3 which demonstrated the ability to inhibit both GSK-3β (IC50 = 24.36 ± 0.01 μM) and Aβ42 self-aggregation (IC50 = 9.0 ± 1.4 μM), to chelate copper (II) and to act as exceptionally strong radical scavenger (kinh = 6.8 ± 0.5 · 105 M?1s?1) even in phosphate buffer at pH 7.4 (kinh = 3.2 ± 0.5 · 105 M?1s?1). Importantly, compound 3 showed high-predicted blood-brain barrier permeability, did not exert any significant cytotoxic effects in immature cortical neurons up to 50 μM and showed neuroprotective properties at micromolar concentration against toxic insult induced by glutamate.

PROCESS FOR THE SYNTHESIS OF SUBSTITUTED 1-BENZYL-3-(1-(ISOXAZOL-4-YLMETHYL)-1H-PYRAZOL-4-YL)IMIDAZOLIDINE-2,4-DIONES

The present invention relates to processes and intermediates for the preparation of compounds of formula (I): or a salt or oxide thereof, wherein Alk, M1, M2, R1, R2, R3, R4, R5,

New chalcones containing nucleosides exhibiting in vitro anti-cancer activities

Twenty-one new chalcones 9a-m (excluding 9e, 9j and 9l) and 10a-m (excluding 10j and 10l), containing nucleobases were synthesized from 2'-hydroxyacetophenone (1) by the reactions including chloromethylation, nucleophilic substitution with thymine and uracil, and Claisen-Schmidt reactions. These new chalcones were evaluated for in vitro cytotoxicity against five human cancer cell lines: SK-LU-1, Hep-G2, MCF7, SW480 and P388. The results showed that most of the tested chalcones exhibited inhibitory activity against five cancer cell lines except 10h, and 10i. Among the synthesized chalcones, compound 10c exhibited most potent cytotoxicity against MCF-7, SK-LU-1, SW480, HepG2 and P388 with IC50 values of 4.42, 4.81, 5.27, 3.67 and 4.11μg/mL, respectively.

Novel analogues of resveratrol: Metabolism and inhibition of colon cancer cell proliferation

Resveratrol is a phytochemical present in the skin of red grapes, and hence red wine as well as a variety of berries and nuts. It is an anti-oxidant, which has shown cancer chemopreventive properties in preclinical rodent models of carcinogenesis. The bioavailability of resveratrol is low, as it is rapidly metabolised to glucuronides and sulfates. The pharmacological activities of conjugate metabolites of phenols are often much lower than those of their metabolic progenitors. Therefore chemical synthetic manipulations aimed at slowing the rate of metabolic conjugation of phenols may generate analogues with increased bioavailability and efficacy. Here we describe the synthesis using the Wittig-Horner-Emmons reaction of a new series of resveratrol analogues in which the phenol moieties were systematically replaced by hydroxymethyl and/or methoxy groups. Incubation of analogues, which lack phenol groups with phase II metabolising enzyme preparations generated hardly any, or only small amounts of, conjugates. Four of the new analogue inhibited the growth of human-derived HCA-7 colon cancer cells, but with much less potency than resveratrol.

1-Phenyl-4-benzoyl-1H-1,2,3-triazoles as orally bioavailable transcriptional function suppressors of Estrogen-related receptor α

Estrogen-related receptor α is a potential candidate target for therapeutic treatment of breast cancer. We describe the discovery and structure-activity relationship study of a series of 1-phenyl-4-benzoyl-1H-1,2, 3-triazoles as novel suppressors of ERRα

Synthesis and QSAR analysis of chalcone derivatives as nitric oxide inhibitory agent

In this study, thirty-eight chalcone analogs were synthesized and evaluated for nitric oxide (NO) inhibition activity on RAW 264.7 cells. Among these compounds, chalcones bearing furanyl group showed remarkable anti-inflammatory activity. Both compounds 2d and 2j were identified as the most potent NO inhibitor on IFN-γ/LPS-activated RAW 264.7 cells. In order to examine the structure-activity relationship, a 3D QSAR analysis was carried out by comparative molecular field analysis (CoMFA) method on the selected chalcones. Partial least square analysis produced a statistically coherent model with good predictive value, r2 = 0.989 and a good cross validated value, q 2 = 0.583.

Anhydrous FePO4 as a cost-effective and recyclable catalyst for tetrahydropyranylation and tetrahydrofuranylation of alcohols and phenols

In this article, a mild and efficient protocol for the tetrahydropyranylation and tetrahydrofuranylation of various aliphatic and benzylic alcohols and phenols into their corresponding THP and THF ethers (with 3,4-dihydro- 2H-pyran, DHP and 2,3-dihydrofuran, DHF) has been developed using a catalytic amount of anhydrous FePO4 at room temperature and relatively short reaction times in good to excellent yields.