91471-08-8

Usage

Structure

benzaldehyde derivative with a methoxy group and a tetrahydro-2H-pyran-2-yl group attached to the fourth carbon atom of the benzene ring

Uses

building block in organic synthesis, medicinal chemistry, pharmaceutical industry, academic research, potential industrial uses

InChI:InChI=1/C13H16O4/c1-15-12-8-10(9-14)5-6-11(12)17-13-4-2-3-7-16-13/h5-6,8-9,13H,2-4,7H2,1H3

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 121-33-5 vanillin 
• 694-54-2 tetrahydro-2H-2-pyranol 
• 13330-65-9 2,4-dimethoxyphenol 
• 896460-67-6 C₁₃H₁₈O₄ 

Downstream Products

• 137889-63-5 (E)-3-Ethoxycarbonyl-4-(3-methoxy-4-tetrahydropyran-2-yloxyphenyl)butenoic acid 
• 7382-59-4 erythro-1-(4-Hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)-1,3-propanediol 
• 7382-59-4 threo-1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol 
• 121-33-5 vanillin 
• 64173-09-7 (E)-1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-en-1-one 
• 336784-85-1 4-hydroxy-4-[3-methoxy-4-(tetrahydro-pyran-2-yloxy)-phenyl]-1-(tetrahydro-pyran-2-yloxy)-butan-2-one 
• 4957-27-1 3,3′-dimethoxy-4,4′-dihydroxystilbene 
• 91471-11-3 1-(4-Hydroxy-3-methoxyphenyl)-1,2-diacetoxyethane 
• 91471-10-2 1-<3-Methoxy-4-(2,3,5,6-tetrahydropyran-2-yloxy)-phenyl>-1,2-ethanediol 
• 71324-20-4 1-(4-Hydroxy-3-methoxyphenyl)-1,2-ethanediol-4-sulfate potassium salt 
• 147904-88-9 allyl 4-[3-methoxy-4-(2-tetrahydropyranyloxy)cinnamoyl]-1-methyl-1-cyclohexanecarboxylate 
• 946161-34-8 C₃₂H₃₈O₇ 
• 946161-27-9 C₃₁H₃₆O₇ 
• 1224713-59-0 2-{4-[(E)-2-(3,5-dimethoxyphenyl)ethen-1-yl]-2-methoxyphenoxy}tetrahydro-2H-pyran 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of novel chalcone-like compounds as potent and reversible pancreatic lipase inhibitors

Pancreatic lipase (PL), a crucial enzyme responsible for hydrolysis of dietary lipids, has been validated as a key therapeutic target to prevent and treat obesity-associated metabolic disorders. Herein, we report the design, synthesis and biological evaluation of a series of chalcone-like compounds as potent and reversible PL inhibitors. Following two rounds of structural modifications at both A and B rings of a chalcone-like skeleton, structure-PL inhibition relationships of the chalcone-like compounds were studied, while the key substituents that would be beneficial for PL inhibition were revealed. Among all tested chalcone-like compounds, compound B13 (a novel chalcone-like compound bearing two long carbon chains) displayed the most potent PL inhibition activity, with an IC50 value of 0.33 μM. Inhibition kinetic analyses demonstrated that B13 could potently inhibit PL-mediated 4-MUO hydrolysis in a mixed inhibition manner, with the Ki value of 0.12 μM. Molecular docking simulations suggested that B13 could tightly bind on PL at both the catalytic site and a non-catalytic site that was located on the surface of PL, which was consistent with the mixed inhibition mode of this agent. In addition, B13 displayed excellent stability in artificial gastrointestinal fluids and good metabolic stability in human liver preparations. Collectively, our findings suggested that chalcone-like compounds were good choices for design and development of orally administrated PL inhibitors, while B13 could be served as a promising lead compound to develop novel anti-obesity agents via targeting on PL.

Design, synthesis and biological evaluation of indanone–chalcone hybrids as potent and selective hCES2A inhibitors

Human carboxylesterase 2 (hCES2A), one of the major serine hydrolases distributed in the small intestine, plays a crucial role in hydrolysis of ester-bearing drugs. Accumulating evidence has indicated that hCES2A inhibitor therapy can modulate the pharmacokinetic and toxicological profiles of some important hCES2A-substrate drugs, such as the anticancer agent CPT-11. Herein, a series of indanone–chalcone hybrids are designed and synthesized to find potent and highly selective hCES2A inhibitors. Inhibition assays demonstrated that most indanone–chalcone hybrids displayed strong to moderate hCES2A inhibition activities. Structure-hCES2A inhibition activity relationship studies showed that introduction of a hydroxyl at the C4’ site and introduction of an N-alkyl group at the C6 site were beneficial for hCES2A inhibition. Particularly, B7 (an N-alkylated 1-indanone–chalcone hybrid) exhibited the most potent inhibition on hCES2A and excellent specificity (this agent could not inhibit other human esterases including hCES1A and butyrylcholinesterase). Inhibition kinetic analyses demonstrated that B7 potently inhibited hCES2A-mediated FD hydrolysis in a mixed inhibition manner, with a calculated Ki value of 0.068 μM. Furthermore, B7 was capable of inhibiting intracellular hCES2A in living cells and displayed good metabolic stability. Collectively, our findings show that indanone–chalcone hybrids are good choices for the development of hCES2A inhibitors, while B7 is a promising candidate for the development of novel anti-diarrhea agents to ameliorate irinotecan-induced intestinal toxicity.

Design, synthesis, and structure-activity relationships of 2-benzylidene-1-indanone derivatives as anti-inflammatory agents for treatment of acute lung injury

Purpose: The purpose of this study was to design and synthesize novel 2-benzylidene-1-indanone derivatives for treatment of acute lung injury. Methods: A series of 39 novel 2-benzylidene-indanone structural derivatives were synthesized and evaluated for anti-inflammatory activity in lipopolysaccharide (LPS)-stimulated murine primary macrophages. Results: Most of the obtained compounds effectively inhibited the LPS-induced expression of IL-6 and TNF-α. The most active compound, 8f, was found to significantly reduce LPS-induced pulmonary inflammation, as reflected by reductions in the concentration of total protein, inflammatory cell count, as well as the lung wet/dry ratio in bronchoalveolar lavage (BAL) fluid. Furthermore, 8f effectively inhibited mRNA expression of several inflammatory cytokines after LPS challenge in vitro and in vivo. Administration of 8f also blocked LPS-induced activation of the proinflammatory NF-κB/MAPK signaling pathway. Conclusion: The simple synthetic preparation and biological properties of these derivatives make these 2-benzylidene-indanone scaffolds promising new entities for the development of anti-inflammatory therapeutics for the treatment of acute lung injury.

Curcumin analog, WZ37, promotes G2/M arrest and apoptosis of HNSCC cells through Akt/mTOR inhibition

Head and neck squamous cell carcinoma (HNSCC) is a leading form of malignancy arising from the head and neck region. Existing conventional therapies are toxic and induce resistance to advanced HNSCC, therefore, new highly efficient therapeutic agents are urgently needed. The present study investigated the anti-cancer efficacy of WZ37, a curcumin analog, in HNSCC cell lines, and defined the mechanism of this activity. Results indicated that WZ37 inhibited proliferation of several HNSCC cell types by G2/M cycle arrest, promoted expression of a pro-apoptotic protein profile, and induced ROS-dependent mitochondrial injury and ER stress. Pre-treatment with NAC, an ROS scavenger, lowered the anti-cancer activity of WZ37 in HEP-2 cells. Long-term treatment of WZ37 (24 h) decreased Akt/mTOR phosphorylation which was accompanied by increased expression of BAD and PTEN. Moreover, co-treatment of WZ37 with MK-2206 (Akt inhibitor) promoted cancer cell apoptosis. Our findings indicated that the anti-cancer potential of WZ37 was attributed to ROS-dependent cell cycle arrest, mitochondrial injury, and ER stress, leading to apoptosis. The basis of the HNSCC cell apoptosis was through a mechanism of inhibition of the oxidant-sensitive Akt/mTOR pathway. We conclude that WZ37 can be a promising anti-cancer agent for the treatment of HNSCC.

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.

Application of monocarbonyl curcumin compound in preparation of YAP protein antagonistic drug

The invention discloses application of a monocarbonyl curcumin compound in the preparation of a YAP protein antagonistic drug. The monocarbonyl curcumin compound has an excellent antitumous effect, and further provides application in the specific targeting tumor treatment by reconstructing an unstable B-diketone group and phenolic hydroxyl group in the curcumin matrix structure, performing C design synthesis on the matrix curcumin under the alkaline condition and having high affinity combined with a YAP protein.

STYRYLBENZOTHIAZOLE DERIVATIVES AND USES IN IMAGING

This disclosure relates to styrylbenzothiazole derivatives for use as in vivo imaging agents for the diagnosis of Parkinson's disease (PD) or other degenerative disorders or conditions of the central nervous system. Early diagnosis is particularly advantageous as neuroprotective treatment can be applied to healthy neural cells to delay or even prevent the onset of debilitating clinical symptoms.

2-sub-(3-methoxyl-4-hydroxyl)-benzyl-1-indanone analogue and applications thereof

The invention discloses a 2-sub-(3-methoxyl-4-hydroxyl)-benzyl-1-indanone analogue and applications thereof. The structure of the 2-sub-(3-methoxyl-4-hydroxyl)-benzyl-1-indanone analogue is represented by the formula (I) shown in the description. In the formula (I), R1 is independently selected from various alkoxyl, hydroxyl, various halogens, trifluoromethyl, or nitro. According to the invention,a plurality of experimental studies are carried out aiming at the technical field of the 2-sub-(3-methoxyl-4-hydroxyl)-benzyl-1-indanone analogue taking substituted chalcone as a parent nucleus structure, a plurality of design, synthesis and pharmacological activity screening are carried out on the 2-sub-(3-methoxyl-4-hydroxyl)-benzyl-1-indanone analogue taking substituted chalcone as a parent nucleus structure, and then the 2-sub-(3-methoxyl-4-hydroxyl)-benzyl-1-indanone analogue taking substituted chalcone as a parent nucleus structure is obtained. The 2-sub-(3-methoxyl-4-hydroxyl)-benzyl-1-indanone analogue of the invention has highly efficient and broad-spectrum anti-inflammatory use.

Selective hydrogenation of conjugated unsaturated ketones containing a hydroxyaryl substituent in the β-position

A high selectivity was achieved in the Ni2B-catalyzed hydrogenation of α,β-unsaturated ketones containing a hydroxyaryl (phenolic) substituent in the β-position. The developed hydrogenation procedure was used to synthesize natural compounds of the phenylpropane series and their structural analogs.