35947-93-4

Upstream product

• 6851-99-6 2-bromo-1-(2-nitrophenyl)ethanone 
• 579-71-5 2-nitrostyrene 
• 993-22-6 tetrabutylammoniun azide 
• 577-59-3 2-acetylnitrobenzene 
• 88057-15-2 2-bromo-1-(2-nitro-phenyl)-ethanol 

Downstream Products

• 305811-35-2 2-methyl-5-(2-nitrophenyl)oxazole 
• 830334-41-3 [5-(2-aminophenyl)oxazol-2-yl]-(2,3-dihydrobenzo[1,4]dioxin-6-yl)amine 
• 1402719-22-5 N-[2-hydroxy-2-(2-nitrophenyl)ethyl]-4-pentynamide 
• 1402719-24-7 1-(2-nitrophenyl)-2-(4-pentynamido)ethyl 6-hydroxyhexylcarbamate 
• 1402719-26-9 1-(2-nitrophenyl)-2-(4-pentynamido)ethyl 6-[bis(4-methoxyphenyl)(phenyl)methoxy]hexanoate 
• 1402719-27-0 (S)-6-hydroxyhexyl-O-1-(2-nitrophenyl)-2-(4-pentynamido)ethylcarbonothioate 
• 1402719-23-6 N-{2-[bis(4-methoxyphenyl)ACHTUNGTRENUNG(phenyl)methoxy]-2-(2-nitrophenyl)ethyl}-4-pentynamide 
• 1402719-25-8 1-(2-nitrophenyl)-2(4-pentynamido)ethyl 6-[bis(4-methoxyphenyl)-(phenyl)methoxy]hexylcarbamate 
• 1402719-28-1 S-6-[bis(4-methoxyphenyl)(phenyl)methoxy]hexyl-O-1-(2-nitrophenyl)-2-(4-pentynamido)ethyl carbonothioate 
• 73685-71-9 1-(o-nitrophenyl)-2-aminoethanol 
• 1629316-86-4 4-hydroxy-4-(2-nitrophenyl)pyrrolidin-2-one 
• 1629336-77-1 4-(2-nitrophenyl)-2-oxo-2,5-dihydropyrrole-1-carboxylic acid tert-butyl ester 
• 1629316-95-5 tert-butyl 2-(4-ethoxy-4-oxobutanoyl)-3-(2-nitrophenyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate 
• 1245633-18-4 4-azido-3-hydroxy-3-(2-nitrophenyl)butyric acid methyl ester 

Relevant academic research and scientific papers

A domino annulation approach to 3,4-diacylpyrrolo[1,2-a]pyrazines: decoration of pyrazine units

A new one-pot, sequential three-component access to 3,4-diacylpyrrolo[1,2-a]pyrazine was achieved from the reaction of an α-haloketone, azide, andN-substituted pyrrole-2-carboxaldehyde under mild reaction conditions, through which a polysubstitution pattern on the pyrazine moiety of the scaffold was realized. The formation of multiple bonds (one C-C and two C-N) was enabled by this domino process involving thein situgeneration of α-iminoketones, intermolecular Mannich reaction, intramolecular imine formation, and aromatization. Construction of the relevant 3,4-diacylpyrazino[1,2-a]indole and further expansion of this chemical spaceviasynthetic elaboration of the resulting products were demonstrated as well. Preliminary biological screening of the synthesized derivatives against oral adenosquamous carcinoma cells (CAL-27) and triple negative human breast cancer cells (MDA-MB-231) led us to identify a potent hit compound (7o) having ～3 times strongerin vitroanticancer activity than that of the anticancer agent, capecitabine.

Visible-Light-Accelerated Copper(II)-Catalyzed Regio- and Chemoselective Oxo-Azidation of Vinyl Arenes

The visible-light-accelerated oxo-azidation of vinyl arenes with trimethylsilylazide and molecular oxygen as stoichiometric oxidant was achieved. In contrast to photocatalysts based on iridium, ruthenium, or organic dyes, [Cu(dap)2]Cl or [Cu(dap)Cl2] were found to be unique for this transformation, which is attributed to their ability to interact with the substrates through ligand exchange and rebound mechanisms. CuII is proposed as the catalytically active species, which upon coordinating azide will undergo light-accelerated homolysis to form CuI and azide radicals. This activation principle (CuII-X→CuI+X.) opens up new avenues for copper-based photocatalysis.

One-pot synthesis of α-bromo- and α-azidoketones from olefins by catalytic oxidation with in situ-generated modified IBX as the key reaction

Simple one-pot protocols for the syntheses of α-bromoketones and α-azidoketones starting from olefins have been developed by employing catalytic oxidation of the intermediary bromohydrins with in situ-generated modified IBX as the key reaction. The improved procedure involves initial formation of bromohydrin by the reaction of olefin with NBS in acetonitrile-water mixture (1:1) at rt followed by oxidation with in situ-generated 3,4,5,6-tetramethyl-2-iodoxybenzoic acid (TetMe-IBX), produced in catalytic amounts from 3,4,5,6-tetramethyl-2-iodobenzoic and Oxone. α-Bromoketones are further converted in the same pot to the corresponding α-azidoketones using NaN3/NaHCO3. The one-pot conversions are versatile for a variety of olefins that include cyclic as well as acyclic aliphatic olefins and electron-rich and electron-deficient styrenes. Chemoselective bromohydroxylation of electron-rich double bond and subsequent oxidation to the α-bromoketone is demonstrated for a substrate that contains both electron-rich and deficient double bonds.

In vitro α-glucosidase inhibition by non-sugar based triazoles of dibenzoazepine, their structure-Activity relationship, and molecular docking

Background: α-Glucosidase inhibitors (AGIs) have been reported for their clinical potential against postprandial hyperglycemia, which is responsible for the risks associated with diabetes mellitus 2 and cardiovascular diseases (CVDs). Besides, a number of

Synthesis and in vitro evaluation of dibenzoazepine triazole derivatives: A novel class of antileishmanial agents

In the present study, a series of dibenzoazepine triazole derivatives (24-39) were synthesized and evaluated for their in vitro bioactivities including antiglycation, antibacterial, DPPH radical scavenging, urease inhibition, antileishmanial and immunomod

Synthetic strategies for the synthesis and transformation of substituted pyrrolinones as advanced intermediates for rhazinilam analogues

The biaryl core structure of rhazinilam with its fixed dihedral angle is a pivotal element for its unique in vitro cytotoxic activity. Most of the related natural products are oxidized versions of rhazinilam. Replacing the sensitive pyrrole ring by a pyrrolinone ring is the basis of our initial strategy towards rhazinilam analogues. With this goal, variants of the sequence crossed Mukaiyama aldol reaction followed by the Staudinger reaction were studied. Reacting a suitably substituted acetophenone with O-methyl O-trimethylsilyl ketene acetal gave pyrrolinones 8a and 8b in good to excellent yields. These intermediates could be transformed in four high-yielding steps into the pyrrolic precursors 7a-c containing all the atoms necessary for the construction of rings A, B, and C of rhazinilam. Our studies illustrate a lack of stability of these intermediates. Alternative synthetic approaches towards this central biaryl core structure are described.

Preparation of precursors for the synthesis of analogues of rhazinilam

Rhazinilam a structurally relatively simple tetracyclic natural product exerts interesting anticancer activities in vitro, which are difficult to reproduce in vivo. Based on the findings accumulated during the synthetic efforts and on the known metabolic

Photocaging strategy for functionalisation of oligonucleotides and its applications for oligonucleotide labelling and cyclisation

We have used a photocaging strategy to develop novel phosphoramidites and expand the repertoire of protecting groups for modification of oligonucleotides by solid-phase synthesis. We synthesised five photolabile phosphoramidites and four new photolabile c

Oxadiazole derivatives as a novel class of antimitotic agents: Synthesis, inhibition of tubulin polymerization, and activity in tumor cell lines

Oxadiazole derivatives were synthesized and evaluated for their ability to inhibit tubulin polymerization and to cause mitotic arrest in tumor cells. The most potent compounds inhibited tubulin polymerization at concentrations below 1 μM. Lead analogs caused mitotic arrest of A431 human epidermoid cells and cells derived from multi-drug resistant tumors (10, EC50 = 7.8 nM). Competition for the colchicine binding site and pharmacokinetic properties of selected potent compounds were also investigated and are reported herein, along with structure-activity relationships for this novel series of antimitotic agents.

Imidazoline derivatives as alpha-1A adrenoceptor ligands

Compound of formula (I) or a pharmaceutically acceptable salt or solvate thereof are disclosed. Such compounds are useful in the treatment of Alpha-1A mediated diseases or conditions such as urinary incontinence.