78256-30-1

Usage

InChI:InChI=1/C13H8N2O3/c16-13-10-4-2-1-3-9(10)11-7-8(15(17)18)5-6-12(11)14-13/h1-7H,(H,14,16)

Upstream product

• 412336-10-8 6-methyl-2-nitro-phenanthridine 
• 1015-89-0 6(5H)-phenanthridinone 
• 15679-03-5 6-chlorophenanthridine 
• 24310-30-3 N-biphenyl-2-yl-4-methylbenzenesulfonamide 
• 90-41-5 2-phenylaniline 
• 847616-80-2 C₂₈H₂₆N₂O₄Pd₂ 
• 2446-51-7 N-methoxybenzamide 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 69605-58-9 5-methoxyphenanthridin-6(5H)-one 
• 98-80-6 phenylboronic acid 
• 615-43-0 2-iodophenylamine 
• 17337-13-2 [1,1'-biphenyl]-2-yl-isocyanate 
• 138344-50-0 tert-butyl [1,1′-biphenyl]-2-ylcarbamate 
• 115293-14-6 1,3-di(biphenyl-2-yl)urea 

Downstream Products

• 78256-05-0 2-aminophenanthridin-6(5H)-one 
• 1322074-81-6 2-nitro-N-[4-methylphenyl]sulfonyl-5,6-dihydrophenanthridine 
• 53364-98-0 2-nitro-6-chlorophenanthridine 

Relevant academic research and scientific papers

In Vitro and Cellular Probes to Study PARP Enzyme Target Engagement

Poly(ADP-ribose) polymerase (PARP) enzymes use nicotinamide adenine dinucleotide (NAD+) to modify up to seven different amino acids with a single mono(ADP-ribose) unit (MARylation deposited by PARP monoenzymes) or branched poly(ADP-ribose) polymers (PARylation deposited by PARP polyenzymes). To enable the development of tool compounds for PARP monoenzymes and polyenzymes, we have developed active site probes for use in in vitro and cellular biophysical assays to characterize active site-directed inhibitors that compete for NAD+ binding. These assays are agnostic of the protein substrate for each PARP, overcoming a general lack of knowledge around the substrates for these enzymes. The in vitro assays use less enzyme than previously described activity assays, enabling discrimination of inhibitor potencies in the single-digit nanomolar range, and the cell-based assays can differentiate compounds with sub-nanomolar potencies and measure inhibitor residence time in live cells. Wigle et al. describe a versatile set of NAD+-competitive probes for PARP enzymes that are used to build high-throughput in vitro and cellular biophysical assays that enable inhibitor screening and determination of residence time.

Rhodium(I)-Catalyzed Aryl C-H Carboxylation of 2-Arylanilines with CO2

An unprecedented Rh(I)-catalyzed, amino-group-assisted C-H carboxylation of 2-arylanilines with CO2 under redox-neutral conditions has been developed. This reaction was promoted by a phosphine ligand with t-BuOK as the base and did not require the use of additional strong organometallic reagent. It enabled an efficient direct conversion of a broad range of 2-(hetero)arylanilines including electron-deficient heteroarenes to various phenanthridinones. Possible intermediates of the reaction were also evaluated in the preliminary mechanistic studies.

Phenanthridinone compound with BRD4 protein inhibiting effect and preparation method and application thereof

The invention discloses a phenanthridinone compound with BRD4 protein inhibiting effect, a preparation method and application thereof. The phenanthridinone compound comprises a compound with a structure shown in a formula (I) and pharmaceutically acceptab

Novel phenanthridin-6(5H)-one derivatives as potent and selective BET bromodomain inhibitors: Rational design, synthesis and biological evaluation

Inhibition of BET family of bromodomain is an appealing intervention strategy for several cancers and inflammatory diseases. This article highlights our work toward the identification of potent, selective, and efficacious BET inhibitors using a structure-

Metal-Oxidant-Free Cobalt-Catalyzed C(sp2)-H Carbonylation of ortho-Arylanilines: An Approach toward Free (NH)-Phenanthridinones

A traceless directing group assisted Co-catalyzed C(sp2)-H carbonylation of ortho-arylanilines for the synthesis of free (NH)-phenanthridinones in metal-based-oxidant-free fashion was accomplished. This protocol employs diisopropyl azodicarboxylate as the CO source and oxygen as the sole oxidant, and provides good yields with various functional tolerance. The methodology has been applied for the total synthesis of PARP inhibitor PJ-34. Furthermore, the kinetic isotopic effect experiments reveal the C-H bond cleavage probably occurred in the rate-determining step.

Palladium-catalyzed cyclization of benzamides with arynes: Application to the synthesis of phenaglydon and N-methylcrinasiadine

N-Methyl or methoxy benzamides reacted with benzynes in the presence of Pd(OAc)2, organic acid and K2S2O8 in CH3CN yielding tricyclic phenanthridinone derivatives in good yields. This journal is

Pd(II)-catalyzed C(sp2)-H carbonylation of biaryl-2-amine: Synthesis of phenanthridinones

A Pd(OAc)2-catalyzed C(sp2)-H carbonylation protocol of arenes under carbon monoxide atmosphere has been developed. The scope of the carbonylation reaction is broad and tolerates a variety of useful functional groups. This reaction provides a novel and efficient method for the synthesis of biologically and pharmaceutically significant phenanthridinones.

Synthesis OF 5,6-dihydrophenanthridine (DHPA) sulfonamides and subsequent acid-catalyzed rearrangement to diaryl sulfones

As part of an ongoing investigation into the rearrangement of cyclic aryl aminesulfonanilides to diarylsulfones, a series of novel 5,6- dihydrophenanthridine (DHPA) sulfonamides were synthesized. Acid catalysts were used to rearrange them to DHPA arylsulfones. Taylor & Francis Group, LLC.

Methods for the treatment of neurodegenerative disorders using substituted phenanthridinone derivatives

This invention provides a novel class of substituted 6(5H)phenanthridinone compounds. The invention also includes pharmaceutical compositions, and methods of making and using the compounds, or a pharmaceutically acceptable salt, hydrate, prodrug, or mixture thereof. Methods of using the compounds and pharmaceutical compositions for treating neurodegenerative disorders, such as multiple sclerosis are also described.

Substituted phenanthridinones and methods of use thereof

This invention provides a novel class of substituted 6(5H)phenanthridinone compounds. Pharmaceutical compositions, and methods of making and using the compounds, or a pharmaceutically acceptable salt, hydrate, prodrug, or mixture thereof are also described.