6845-81-4

Usage

InChI:InChI=1/C9H7ClO3/c10-9(11)4-6-1-2-7-8(3-6)13-5-12-7/h1-3H,4-5H2

Upstream product

• 120-57-0 piperonal 
• 35453-09-9 2-(3,4-methylenedioxyphenyl)-1-(methylsulfinyl)-1-(methylthio)ethylene 
• 26664-86-8 (benzo[1,3]dioxol-5-yl)acetic acid ethyl ester 
• 25379-88-8 2-(3,4-dihydroxyphenyl)acetic acid methyl ester 
• 102-32-9 3,4-dihydroxyphenylacetate 
• 326-59-0 benzo[1,3]dioxol-5-yl-acetic acid methyl ester 
• 2861-28-1 1,3-benzodioxole-5-acetic acid 

Downstream Products

• 87232-89-1 2-Hydroxy-3,4,5,6-tetramethoxyphenyl 3,4-methylenedioxybenzyl ketone 
• 62684-38-2 2-hydroxy-3,4,6-trimethoxyphenyl-3,4-methylenedioxybenzyl ketone 
• 96718-69-3 2-Benzo[1,3]dioxol-5-yl-N-phenyl-acetamide 
• 5653-25-8 α-(1,3-benzodioxol-5-yl)-2,4-dihydroxyacetophenone 
• 107914-36-3 Benzo[1,3]dioxol-5-yl-acetic acid 3-hydroxy-phenyl ester 
• 347378-55-6 5-benzyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline 
• 347378-45-4 5-benzyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline 
• 347378-50-1 (S)-N-[2-(3,4-methylenedioxyphenyl)ethyl]-1-phenylethanolamine 
• 347378-40-9 (R)-N-[2-(3,4-methylenedioxyphenyl)ethyl]-1-phenylethanolamine 
• 347378-46-5 5-benzyl-6-propyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline 
• 347378-56-7 5-benzyl-6-propyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline 
• 347378-51-2 (S)-N-(1-phenyl-2-phenylacetylethoxy)-N-[2-(3,4-methylenedioxyphenyl)ethyl]-2-phenylacetamide 
• 347378-41-0 (R)-N-(1-phenyl-2-phenylacetylethoxy)-N-[2-(3,4-methylenedioxyphenyl)ethyl]-2-phenylacetamide 
• 347378-43-2 (1S)-1-benzyl-(R)-N-(1-phenyl-2-phenylacetylethoxy)-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline 

Relevant academic research and scientific papers

A Diverse Library of Chiral Cyclopropane Scaffolds via Chemoenzymatic Assembly and Diversification of Cyclopropyl Ketones

Chiral cyclopropane rings are key pharmacophores in pharmaceuticals and bioactive natural products, making libraries of these building blocks a valuable resource for drug discovery and development campaigns. Here, we report the development of a chemoenzymatic strategy for the stereoselective assembly and structural diversification of cyclopropyl ketones, a highly versatile yet underexploited class of functionalized cyclopropanes. An engineered variant of sperm whale myoglobin is shown to enable the highly diastereo- and enantioselective construction of these molecules via olefin cyclopropanation in the presence of a diazoketone carbene donor reagent. This biocatalyst offers a remarkably broad substrate scope, catalyzing this reaction with high stereoselectivity across a variety of vinylarene substrates as well as a range of different α-aryl and α-alkyl diazoketone derivatives. Chemical transformation of these enzymatic products enables further diversification of these molecules to yield a collection of structurally diverse cyclopropane-containing scaffolds in enantiopure form, including core motifs found in drugs and natural products as well as novel structures. This work illustrates the power of combining abiological biocatalysis with chemoenzymatic synthesis for generating collections of optically active scaffolds of high value for medicinal chemistry and drug discovery.

Two-Photon Excitable Photoremovable Protecting Groups Based on the Quinoline Scaffold for Use in Biology

Photoremovable protecting groups (PPGs) are powerful tools for physiological studies, harnessing light as an on/off switch to provide tight spatio-temporal control over the release of biological effectors through two-photon excitation (2PE) in tissue culture and whole-animal studies. We carried out a series of systematic structural modifications to the (8-cyano-7-hydroxyquinolin-2-yl)methyl (CyHQ) chromophore to conduct an SAR study with the aim of enhancing its photochemical properties, especially its two-photon uncaging action cross section (δu). The best results were obtained when substituents were added at the C4 position, which improved δu for release of acetate up to 7-fold, while retaining all the other excellent properties of the CyHQ PPG, including high quantum yield (φu), low susceptibility to spontaneous hydrolysis in the dark, and good aqueous solubility. Hammett correlation analysis suggested that photolysis efficiency is favored by electron-rich substituents at C4, giving important insights into the mechanism of the photolysis reaction. The four best CyHQ derivatives were used to mediate the efficient release of homopiperonylic acid in high yield under simulated physiological conditions. Our efforts have led to the development of 2PE-sensitive PPGs with remarkable δu values (up to 2.64 GM), excellent quantum yields (up to 0.88), and high-yielding effector release (up to 92%).

N-monoarylacetothioureas as potent urease inhibitors: synthesis, SAR, and biological evaluation

A urease inhibitor with good in vivo profile is considered as an alternative agent for treating infections caused by urease-producing bacteria such as Helicobacter pylori. Here, we report a series of N-monosubstituted thioureas, which act as effective urease inhibitors with very low cytotoxicity. One compound (b19) was evaluated in detail and shows promising features for further development as an agent to treat H. pylori caused diseases. Excellent values for the inhibition of b19 against both extracted urease and urease in intact cell were observed, which shows IC50 values of 0.16 ± 0.05 and 3.86 ± 0.10 μM, being 170- and 44-fold more potent than the clinically used drug AHA, respectively. Docking simulations suggested that the monosubstituted thiourea moiety penetrates urea binding site. In addition, b19 is a rapid and reversible urease inhibitor, and displays nM affinity to urease with very slow dissociation (koff=1.60 × 10?3 s?1) from the catalytic domain.

Visible-Light-Assisted Gold-Catalyzed Fluoroarylation of Allenoates

A strategically novel synthetic method for the fluoroarylation of allenic ester was developed that enables the expedient construction of a host of β-fluoroalkyl-containing cinnamate derivatives. The reaction proceeds through visible-light-promoted gold redox catalysis, occurs smoothly under very mild reaction conditions, accommodates a large variety of functional groups, and more importantly allows the incorporation of fluorine and aryl groups with excellent regio- and stereoselectivity. The concomitant activation mode for both the allene motif and the hydrogen fluoride is key for the success of the reaction.

Ni-Catalyzed Regiodivergent and Stereoselective Hydroalkylation of Acyclic Branched Dienes with Unstabilized C(sp3) Nucleophiles

Two complementary regiodivergent [(P,N)Ni]-catalyzed hydroalkylations of branched dienes are reported. When amides are employed as unstabilized C(sp3) nucleophiles, a highly regioselective 1,4-addition process is favored. The addition products are obtained in high yield and with excellent stereocontrol of the internal olefin. With use of a chiral ligand and imides as carbon nucleophiles, a 3,4-addition protocol was developed, enabling construction of two contiguous tertiary stereocenters in a single step with moderate to high levels of diastereocontrol and excellent enantiocontrol. Both methods operate under mild reaction conditions, display a broad scope, and show excellent functional group tolerance. The synthetic potential of the 3,4-hydroalkylation reaction was established via a series of postcatalytic modifications.

Discovery of γ-Lactam alkaloid derivatives as potential fungicidal agents targeting steroid biosynthesis

Biological control of plant pathogens is considered as one of the green and effective technologies using beneficial microorganisms or microbial secondary metabolites against plant diseases, and so microbial natural products have played important roles in the research and development of new and green agrochemicals. To explore the potential applications for natural γ-lactam alkaloids and their derivatives, 26 γ-lactams that have flexible substituent patterns were synthesized and characterized, and their in vitro antifungal activities against eight kinds of plant pathogens belonging to oomycetes, basidiomycetes, and deuteromycetes were fully evaluated. In addition, the high potential compounds were further tested using an in vivo assay against Phytophthora blight of pepper to verify a practical application for controlling oomycete diseases. The potential modes of action for compound D1 against Phytophthora capsici were also investigated using microscopic technology (optical microscopy, scanning electron microscopy, and transmission electron microscopy) and label-free quantitative proteomics analysis. The results demonstrated that compound D1 may be a potential novel fungicidal agent against oomycete diseases (EC50 = 4.9748 μg·mL-1 for P. capsici and EC50 = 5.1602 μg·mL-1 for Pythium aphanidermatum) that can act on steroid biosynthesis, which can provide a certain theoretical basis for the development of natural lactam derivatives as potential antifungal agents.

Preparation of Organic Nitrates from Aryldiazoacetates and Fe(NO3)3·9H2O

A thermal protocol is reported for the formal insertion of nitric acid into aryldiazoacetates using Fe(NO3)3·9H2O. This strategy is mild and high yielding and allows the preparation of a large variety of members of an unprecedented family of organic nitrates. The nitrate group can be also readily transformed into other functional groups and heterocyclic moieties and can possibly allow new biological explorations of untapped potential associated with their NO-releasing ability.

Retinoid Compounds containing DOPAC and preparing method thereof

The present invention relates to retinoid compounds comprising dopamine metabolites and a preparation method of the same, and more specifically, to retinoid compounds comprising dopamine metabolites, which by bonding a dopamine metabolite, 3,4-(methylenedioxy)phenylacetic acid or 3,4-dihydroxyphenylacetic acid to retinol, enhances the function of retinol while minimizing its degradation over a long term usage; and to a preparation method of the same. According to the present invention, a retinoid compound having minimized its degradation over a long term usage, thereby having excellent stability can be obtained from preparing a retinoid compound by bonding a dopamine metabolite, 3,4-(methylenedioxy)phenylacetic acid or 3,4-dihydroxyphenylacetic acid to a terminal end of retinol. Additionally, according to the present invention, a retinoid compound having low irritability when applied to the skin can be obtained from preparing a retinoid compound by bonding a dopamine metabolite, 3,4-(methylenedioxy)phenylacetic acid or 3,4-dihydroxyphenylacetic acid to a terminal end of retinol.(S101) Pre-treat 3.4-(methylenedioxy)phenylacetic acid by using oxalyl chloride(S201) React the pre-treated 3.4-(methylenedioxy)phenylacetic acid with retinol to form an ester bond, and thereby form a retinoid compound containing dopamine metabolites(S301) Extract a retinoid compound containing the synthesized DOPACCOPYRIGHT KIPO 2017

Stereoselective synthesis of Z-vinylsilanes via palladium-catalyzed direct intermolecular silylation of C(sp2)-H bonds

An efficient and convenient palladium-catalyzed direct intermolecular silylation of C(sp2)-H bonds by using disilanes as the silicon source with the assistance of a readily removable bidentate directing group is reported. This strategy provided a regio- and stereoselective protocol for exclusive synthesis of Z-vinylsilanes with reasonable to excellent yields and good functional group compatibility. Silylation of the isolated palladacycle intermediate revealed the Z-stereoselective pathway. Moreover, the practicality and effectiveness of this method were illustrated by a gram-scale experiment and further functionalization of the silylation product.

Synthesis of 2-oxindoles via 'transition-metal-free' intramolecular dehydrogenative coupling (IDC) of sp2 C-H and sp3 C-H bonds

The synthesis of a variety of 2-oxindoles bearing an all-carbon quaternary center at the pseudo benzylic position has been achieved via a 'transition-metal-free' intramolecular dehydrogenative coupling (IDC). The construction of 2-oxindole moieties was carried out through formation of carbon-carbon bonds using KOt-Bu-catalyzed one pot C-alkylation of β-N-arylamido esters with alkyl halides followed by a dehydrogenative coupling. Experimental evidences indicated toward a radical-mediated path for this reaction.