83520-63-2

Upstream product

• 280113-46-4 5-nitro-2-(2-propynyloxy)styrene 
• 280113-67-9 5-nitro-2-(prop-2-ynyloxy)benzaldehyde 
• 97-51-8 5-Nitrosalicylaldehyde 
• 1779-49-3 Methyltriphenylphosphonium bromide 

Downstream Products

• 104333-07-5 2-(2-Hydroxy-ethyl)-4-nitro-phenol 
• 1046817-88-2 2-(3-(4-nitro-2-vinylphenoxy)propyl)isoindoline-1,3-dione 
• 1607446-72-9 (E)-2-(2-hydroxy-5-nitrophenyl)-4-methylhex-4-en-3-one 
• 1607446-73-0 C₁₇H₁₈N₂O₄ 
• 1607447-02-8 N,N-dimethyl-4-(3-methyl-5-nitrobenzofuran-2-yl)aniline 
• 1607446-74-1 C₁₆H₁₅NO₅ 
• 1607447-01-7 2-(4-methoxyphenyl)-3-methyl-5-nitrobenzofuran 
• 1607446-75-2 2-(2-hydroxy-5-nitrophenyl)-1-phenylpropan-1-one 
• 860580-15-0 C₁₅H₁₃NO₄ 
• 1607446-76-3 methyl 4-(2-(2-hydroxy-5-nitrophenyl)propanoyl)benzoate 
• 1607446-77-4 1-(4-hydroxy-3-methoxyphenyl)-2-(2-hydroxy-5-nitrophenyl)propan-1-one 
• 2725-81-7 6-nitrocoumarin 

Relevant academic research and scientific papers

Aryloxybenzylidene ruthenium chelates: Synthesis, structure and catalytic activity in olefin metathesis

New aryloxybenzylidene ruthenium chelates behave like a promising latent catalyst of olefin metathesis. The catalysts are characterised by substantial stability and catalytic inactivity in their dormant forms and a dramatic increase in activity after addi

7-Acylamino-3H-1,2-benzoxathiepine 2,2-dioxides as new isoform-selective carbonic anhydrase IX and XII inhibitors

A series of 3H-1,2-benzoxathiepine 2,2-dioxides incorporating 7-acylamino moieties were obtained by an original procedure starting from 5-nitrosalicylaldehyde, which was treated with propenylsulfonyl chloride followed by Wittig reaction of the bis-olefin intermediate. The new derivatives, belonging to the homosulfocoumarin chemotype, were assayed as inhibitors of the zinc metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1). Four pharmacologically relevant human (h) isoforms were investigated, the cytosolic hCA I and II and the transmembrane, tumour-associated hCA IX and XII. No relevant inhibition of hCA I and II was observed, whereas some of the new derivatives were effective, low nanomolar hCA IX/XII inhibitors, making them of interest for investigations in situations in which the activity of these isoforms is overexpressed, such as hypoxic tumours, arthritis or cerebral ischaemia.

3H-1,2-benzoxathiepine 2,2-dioxides: a new class of isoform-selective carbonic anhydrase inhibitors

A new chemotype with carbonic anhydrase (CA, EC 4.2.1.1) inhibitory action has been discovered, the homo-sulfocoumarins (3H-1,2-benzoxathiepine 2,2-dioxides) which have been designed considering the (sulfo)coumarins as lead molecules. An original synthetic strategy of a panel of such derivatives led to compounds with a unique inhibitory profile and very high selectivity for the inhibition of the tumour associated (CA IX/XII) over the cytosolic (CA I/II) isoforms. Although the CA inhibition mechanism with these new compounds is unknown for the moment, we hypothesize that it may be similar to that of the sulfocoumarins, i.e. hydrolysis to the corresponding sulfonic acids which thereafter anchor to the zinc-coordinated water molecule within the enzyme active site.

Bichromatic Photosynthesis of Coumarins by UV Filter-Enabled Olefin Metathesis

Herein, we report on a two-step bichromatic synthesis of coumarins involving UV-A and UV-C light. The first step is a UV-A-photoinduced ruthenium-catalyzed cross-metathesis (CM) reaction of 2-nitrobenzyl-protected 2-hydroxystyrenes with acrylates, using an external solution of 1-pyrenecarboxaldehyde as a UV filter. Irradiation in the absence of the filter permanently inhibits the light-activated catalyst due to photocleavage of the photolabile protecting group (PPG) and ensuing phenolate chelation to the ruthenium. The simple removal of the external filter after CM allows further photochemical reactions with UV-C light to achieve more complex architectures, such as the coumarins presented in this work. (Figure presented.).

Aryloxybenzylidene ruthenium chelates: Synthesis, structure and catalytic activity in olefin metathesis

New aryloxybenzylidene ruthenium chelates behave like a promising latent catalyst of olefin metathesis. The catalysts are characterised by substantial stability and catalytic inactivity in their dormant forms and a dramatic increase in activity after addi

Substrate-directed hydroacylation: Rhodium-catalyzed coupling of vinylphenols and nonchelating aldehydes

We report a protocol for the hydroacylation of vinylphenols with aryl, alkenyl, and alkyl aldehydes to form branched products with high selectivity. This cross-coupling yields α-aryl ketones that can be cyclized to benzofurans, and it enables access to eu

Endo-selective pd-catalyzed silyl methyl heck reaction

A palladium (Pd)-catalyzed endo-selective Heck reaction of iodomethylsilyl ethers of phenols and aliphatic alkenols has been developed. Mechanistic studies reveal that this silyl methyl Heck reaction operates via a hybrid Pd-radical process and that the silicon atom is crucial for the observed endo selectivity. The obtained allylic silyloxycycles were further oxidized into (Z)-alkenyldiols.

Synthesis of tricyclic aromatic compounds by the intramolecular Pauson-Khand reaction promoted by molecular sieves

Pauson-Khand reactions are carried out with different substituted aromatic enynes, yielding tricyclic cyclopentenones related to natural products such as chromenes. Enynes are easily obtained in a two-step approximation from the corresponding salicylaldehydes. The reaction is promoted by dissolved TMANO (trimethylamine N-oxide) and/or 4 A molecular sieves. This new way of induction for the Pauson-Khand reaction increases yields remarkably, allowing the reaction of some substituted alkenes which fail to react in the absence of the zeolite. Isomerization of the double bond of the cyclopentenone ring is observed except when nonterminal triple bonds are used. For trisubstituted alkenes, an interrupted Pauson-Khand process is observed with moderate yields.