69404-94-0

Upstream product

• 121-33-5 vanillin 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 69739-34-0 t-butyldimethylsiyl triflate 

Downstream Products

• 121-33-5 vanillin 
• 173531-47-0 tert-butyl-(4-ethynyl-2-methoxyphenoxy)dimethylsilane 
• 881-68-5 vanillin acetate 
• 1361253-08-8 (6-methoxy-1,3-benzothiazol-2-yl)[3-methoxy-4-(tert-butyldimethylsilanyloxy)phenyl]methanol 
• 1361252-75-6 (6-hydroxy-1,3-benzothiazol-2-yl)(3-hydroxy-4-phenoxyphenyl)methanone 
• 1361253-11-3 (6-methoxy-1,3-benzothiazol-2-yl)(3-methoxy-4-phenoxyphenyl)methanone 
• 1361253-10-2 (6-methoxy-1,3-benzothiazol-2-yl)(3-methoxy-4-hydroxyphenyl)methanone 
• 1361253-09-9 (6-methoxy-1,3-benzothiazol-2-yl)[3-methoxy-4-(tert-butyldimethylsilanyloxy)phenyl]methanone 
• 1428741-15-4 C₂₅H₃₉NO₈Si 
• 1428741-17-6 (3S,4S)-methyl 4-(tert-butyldimethylsilyloxy)-4-(4-(tert-butyldimethylsilyloxy)-3-methoxyphenyl)-3-((S)-4-isopropyl-2-oxooxazolidine-3-carbonyl)butanoate 
• 1428741-21-2 (S)-2-((S)-(tert-butyldimethylsilyloxy)(4-(tert-butyldimethylsilyloxy)-3-methoxyphenyl)methyl)-4-methoxy-4-oxobutanoic acid 

Relevant academic research and scientific papers

Chromium-Salen Complex/Nitroxyl Radical Cooperative Catalysis: A Combination for Aerobic Intramolecular Dearomative Coupling of Phenols

We describe an aerobic intramolecular dearomative coupling reaction of tethered phenols using a catalytic system consisting of a chromium-salen (Cr-salen) complex combined with a nitroxyl radical. This novel catalytic system enables formation of various spirocyclic dienone products including those unable to be accessed by previously reported methods efficiently under mild reaction conditions.

Synthesis and Photoswitching Properties of Bioinspired Dissymmetric I-Pyrone, an Analogue of Cyclocurcumin

Cyclocurcumin (CC), a turmeric curcuminoid with potential therapeutic properties, is also a natural photoswitch that may undergo E/Z photoisomerization under UV light. To be further exploited in relevant biological applications, photoactivation under near-infrared (NIR) irradiation is required. Such requirement can be met through opportune chemical modifications, by favoring two-photon absorption (TPA) probability. Herein, a general and efficient synthesis of a biomimetic 2,6-disubstituted-δ-pyrone analogue of CC is described, motivated by the fact that molecular modeling previews an order of magnitude increase of its NIR TPA compared to CC. Three retrosynthetic pathways have been identified (i) via an aryl-oxazole intermediate or via aryl-diynone through (ii) a bottom-up or (iii) a top-down approach. While avoiding the passage through unstable synthons or low-yield intermediate reactions, only the latest approach could conveniently afford the 2,6-disubstituted-I-pyrone analogue of CC, in ten steps and with an overall yield of 18%. The photophysical properties of our biomimetic analogue have also been characterized showing an improved photoisomerization yield over the parent natural compound. The potentially improved nonlinear optical properties, as well as enhanced stability, may be correlated to the enforcement of the planarity of the pyrone moiety leading to a quadrupolar D-π-A-π-D system.

Synthesis method of yakuchinone-A

The invention provides a synthesis method of yakuchinone-A, and belongs to the technical field of organic chemical synthesis. The preparation method is suitable for industrial production of the yakuchinone-A. According to the method, vanillin is taken as a starting raw material, an alkylation reaction, a wittig-harner reaction, a hydrolysis reaction, a reduction reaction and various reactions are sequentially carried out to finally obtain crude yakuchinone, and then the crude yakuchinone is recrystallized by an organic solvent to prepare the high-purity yakuchinone. The method specifically characterized by synthesizing a compound 8 through the vanillin, synthesizing a compound 9 through the compound 8, synthesizing a compound 10 through the compound 9, synthesizing a compound 11 through the compound 10, and finally synthesizing the yakuchinone-A through the compound 11, and then obtaining the high-purity yakuchinone-A through a recrystallization means. The synthesis method disclosed by the invention has the advantages of easily available raw materials, low cost, easiness in operation, good safety, less pollution, simplicity in purification, easiness in quality control and the like.

Copper-Catalyzed Transfer Hydrodeuteration of Aryl Alkenes with Quantitative Isotopomer Purity Analysis by Molecular Rotational Resonance Spectroscopy

A copper-catalyzed alkene transfer hydrodeuteration reaction that selectively incorporates one hydrogen and one deuterium atom across an aryl alkene is described. The transfer hydrodeuteration protocol is selective across a variety of internal and terminal alkenes and is also demonstrated on an alkene-containing complex natural product analog. Beyond using 1H, 2H, and 13C NMR analysis to measure reaction selectivity, six transfer hydrodeuteration products were analyzed by molecular rotational resonance (MRR) spectroscopy. The application of MRR spectroscopy to the analysis of isotopic impurities in deuteration chemistry is further explored through a measurement methodology that is compatible with high-throughput sample analysis. In the first step, the MRR spectroscopy signatures of all isotopic variants accessible in the reaction chemistry are analyzed using a broadband chirped-pulse Fourier transform microwave spectrometer. With the signatures in hand, measurement scripts are created to quantitatively analyze the sample composition using a commercial cavity enhanced MRR spectrometer. The sample consumption is below 10 mg with analysis times on the order of 10 min using this instrument - both representing order-of-magnitude reduction compared to broadband MRR spectroscopy. To date, these measurements represent the most precise spectroscopic determination of selectivity in a transfer hydrodeuteration reaction and confirm that product regioselectivity ratios of >140:1 are achievable under this mild protocol.

PHOTOPROXIMITY PROFILING OF PROTEIN-PROTEIN INTERACTIONS IN CELLS

Photoactive probes and probe systems for detecting biological interactions are described. The photoactive probes include probes that combine both photocleavable and photoreactive moieties. The photoactive probe systems can include a first probe comprising a photocatalytic group and a second probe comprising a group that can act as a substrate for the reaction catalyzed by the photocatalytic group. The probes and probe systems can also include groups that can specifically bind to a binding partner on a biological entity of interest and a detectable group or a precursor thereof. The probes and probe systems can detect spatiotemporal interactions of proteins or cells. In some embodiments, the interactions can be detected in live cells. Also described are methods of detecting the biological interactions.

Natural product inspired optimization of a selective TRPV6 calcium channel inhibitor

Transient receptor potential vanilloid 6 (TRPV6) is a calcium channel implicated in multifactorial diseases and overexpressed in numerous cancers. We recently reported the phenyl-cyclohexyl-piperazine cis-22a as the first submicromolar TRPV6 inhibitor. This inhibitor showed a seven-fold selectivity against the closely related calcium channel TRPV5 and no activity on store-operated calcium channels (SOC), but very significant off-target effects and low microsomal stability. Here, we surveyed analogues incorporating structural features of the natural product capsaicin and identified 3OG, a new oxygenated analog with similar potency against TRPV6 (IC50 = 0.082 ± 0.004 μM) and ion channel selectivity, but with high microsomal stability and very low off-target effects. This natural product-inspired inhibitor does not exhibit any non-specific toxicity effects on various cell lines and is proposed as a new tool compound to test pharmacological inhibition of TRPV6 mediated calcium flux in disease models.

Synthesis and Cytotoxicity Studies of Stilbene Long-Chain Fatty Acid Conjugates

A series of 16 conjugates of the tubulin polymerization inhibitor combretastatin A4 (CA-4) and other functionally related stilbene with four 18-carbon fatty acids, namely, stearic, oleic, linoleic, and linolenic acids, have been synthesized in good yields. These new derivatives have been evaluated against the KB-3-1 (human epidermoid carcinoma), NCI-H460 (human lung cancer), HEK293 (human embryonic kidney), and MCF-7 (human breast adenocarcinoma) cell lines for antiproliferative activity, with the exhibited cytotoxic activities comparable with those of CA-4 and colchicine. Compounds 22 and 23, CA-4 conjugates of linoleic and linolenic acids, respectively, were determined to have exhibited the most active in vitro assays, with compound 23 exhibiting very similar activity to the parent compound against the NCI-H460 cell line. Our studies further delineated the structurally required Z-geometry of the stilbene moiety and that conjugation of the less active E-stilbenes with the most active fatty acid had minimal or no improvement in their respective activities.

Discovery and Characterization of Pure RhlR Antagonists against Pseudomonas aeruginosa Infections

Pseudomonas aeruginosa (P. aeruginosa) is an opportunistic human pathogen that forms biofilms and produces virulence factors via quorum sensing (QS). Blocking the QS system in P. aeruginosa is an excellent strategy to reduce biofilm formation and the production of virulence factors. RhlR plays an essential role in the QS system of P. aeruginosa. We synthesized 55 analogues based on the chemical structure of 4-gingerol and evaluated their RhlR inhibitory activities using the cell-based reporter strain assay. Comprehensive structure-activity relationship studies identified the alkynyl ketone 30 as the most potent RhlR antagonist. This compound displayed selective RhlR antagonism over LasR and PqsR, strong inhibition of biofilm formation, and reduced production of virulence factors in P. aeruginosa. Furthermore, the survival rate of Tenebrio molitor larvae treated with 30 in vivo greatly improved. Therefore, compound 30, a pure RhlR antagonist, can be utilized for developing QS-modulating molecules in the control of P. aeruginosa infections.

BIS PHENYL HEXA TRIEN DERIVATIVES, PREPARATION METHOD THEREOF, AND COMPOSITION FOR SKIN WHITENING CONTAINING THE SAME AS AN ACTIVE INGREDIENT

The present invention relates to a bis phenyl hexa triene derivative, a preparation method thereof and a composition for skin whitening comprising the same as an active ingredient. The said derivative inhibits the expression of tyrosinase, TRP 1 (tyrosina

Biological evaluation of natural and synthesized homovanillic acid esters as inhibitors of intestinal fatty acid uptake in differentiated Caco-2 cells

With raising prevalence of obesity, the regulation of human body fat is increasingly relevant. The modulation of fatty acid uptake by enterocytes represents a promising target for body weight maintenance. Recent results demonstrated that the trigeminal active compounds capsaicin, nonivamide, and trans-pellitorine dose-dependently reduce fatty acid uptake in differentiated Caco-2 cells as a model for the intestinal barrier. However, non-pungent alternatives have not been investigated and structural determinants for the modulation of intestinal fatty acid uptake have not been identified so far. Thus, based on the previous results, we synthesized 23 homovanillic acid esters in addition to the naturally occurring capsiate and screened them for their potential to reduce intestinal fatty acid uptake using the fluorescent fatty acid analog Bodipy-C12 in differentiated Caco-2 cells as an enterocyte model. Whereas pre-incubation with 100 μM capsiate did not change fatty acid uptake by Caco-2 enterocytes, a maximum inhibition of ?47% was reached using 100 μM 1-methylpentyl-2-(4-hydroxy-3-methoxy-phenyl)acetate. Structural analysis of the 24 structural analogues tested in the present study revealed that a branched fatty acid side chain, independent of the chain length, is one of the most important structural motifs associated with inhibition of fatty acid uptake in Caco-2 enterocytes. The results of the present study may serve as an important basis for designing potent dietary inhibitors of fatty acid uptake.