39895-56-2

Usage

Chemical Properties

Off-White Solid

InChI:InChI=1/C8H11NO/c9-5-7-1-3-8(6-10)4-2-7/h1-4,10H,5-6,9H2

Upstream product

• 7153-22-2 ethyl 4-cyanobenzoate 
• 6757-31-9 methyl-4-carbamoylbenzoate 
• 56-91-7 p-aminomethylbenzoic acid 
• 1129-35-7 4-cyanobenzoic acid methyl ester 
• 105-07-7 4-cyanobenzaldehyde 
• 17201-43-3 4-cyanobenzyl bromide 
• 1679-64-7 Monomethyl terephthalate 
• 6232-11-7 methyl 4-(aminomethyl)benzoate hydrochloride 
• 168761-51-1 4-chloro-7-ethylamino-6-nitroquinazoline 
• 79606-51-2 4-cyano-N,N-diphenylbenzamide 
• 510772-10-8 4-(azidomethyl)benzaldehyde 
• 439691-96-0 [4-(azidomethyl)phenyl]methanol 
• 52010-97-6 4-(hydroxylmethyl)benzaldehyde 
• 51359-78-5 4-(bromomethyl)benzaldehyde 

Downstream Products

• 112656-25-4 2-(4-hydroxymethyl-benzylamino)-2-deoxy-D-glucononitrile 
• 13990-98-2 4-<(dimethylamino)methyl>benzyl alcohol 
• 136869-07-3 N-acetyl(4-hydroxymethyl)benzylamine 
• 123986-64-1 tert-butyl 4-hydroxymethylbenzylcarbamate 
• 171723-95-8 2,2,2-trifluoro-N-[[4-(hydroxymethyl)phenyl]methyl]acetamide 
• 874-89-5 4-Cyanobenzyl alcohol 
• 565448-33-1 N-[4-(chloromethyl)benzyl]methanesulfonamide 
• 617691-20-0 N-(4-hydroxymethylbenzyl)nicotinamide 
• 617691-15-3 N-(4-hydroxymethylbenzyl)-4-pyrrolidin-1-ylbenzamide 
• 1007859-08-6 N-((4-(hydroxymethyl)phenyl)methyl)prop-2-enyloxycarboxamide 
• 864850-82-8 N-[4-(hydroxymethyl)benzyl]-2-naphthamide 
• 750562-31-3 N-((4-(hydroxymethyl)phenyl)methyl)-4-amino-1-methylpiperidine 
• 866123-51-5 5-nitrofuran-2-carboxylic acid 4-hydroxymethyl-benzylamide 
• 944247-89-6 C₂₆H₂₀O₆N₂ 

Relevant academic research and scientific papers

Complexation of 5-aminovaleric acid zwitterions in aqueous/methanol solution by heterotopic tri-cationic receptors

Heterotopic tri-cationic receptors based on 4,10,16-triaza-18-crown-6 are capable of efficient and selective binding of the zwitterionic form of 5-aminovaleric acid (5-AVA) in aqueous/methanol solution. The cooperative participation of both cation and ani

A wash-free SNAP-tag fluorogenic probe based on the additive effects of quencher release and environmental sensitivity

A 1,8-naphthalimide-derived fluorogenic probe was reported to label SNAP-tag fusion proteins in living cells. The probe can rapidly label a SNAP-tag and exhibit a fluorescence increase of 36-fold due to the additive effects of environment sensitivity of fluorophores and inhibition of photo-induced electron transfer from O6-benzylguanine to the fluorophore. The labeling of intracellular proteins has been successfully achieved without a wash-out procedure.

Chiral molecular recognition in a tripeptide benzylviologen cyclophane host

A cationic chiral cyclophane was synthesized and studied as a host for chiral and racemic π-donor molecules. The cyclophane host has a rigid binding cavity flanked by (S)-(valine-leucine-alanine) and N,N'-dibenzyl- 4,4'-bipyridinium subunits, which allow for hydrogen-bonding and π-stacking interactions with included aromatic guest molecules. 1H NMR binding titrations were performed with several different pharmaceutically interesting guest molecules including β-blockers, NSAIDs, and amino acids and amino acid derivatives. The host-guest complexation constants were generally small for neutral and cationic guests (0-39 M-1 at 20 °C in water/acetone mixtures. However, a (R)/(S) enantioselectivity ratio of 13 ± 5 was found for DOPA, a strongly π-donating cationic guest. Two-dimensional NOESY 1H NMR spectra confirm that (R)-DOPA binds inside the cavity of the host and that there is no measurable interaction of the cavity with (S)-DOPA under the same conditions.

Tuning the Reactivity of a Substrate for SNAP-Tag Expands Its Application for Recognition-Driven DNA-Protein Conjugation

Recognition-driven modification has been emerging as a novel approach to modifying biomolecular targets of interest site-specifically and efficiently. To this end, protein modular adaptors (MAs) are the ideal reaction model for recognition-driven modification of DNA as they consist of both a sequence-specific DNA-binding domain (DBD) and a self-ligating protein-tag. Coupling DNA recognition by DBD and the chemoselective reaction of the protein tag could provide a highly efficient sequence-specific reaction. However, combining an MA consisting of a reactive protein-tag and its substrate, for example, SNAP-tag and benzyl guanine (BG), revealed rather nonselective reaction with DNA. Therefore new substrates of SNAP-tag have been designed to realize sequence-selective rapid crosslinking reactions of MAs with SNAP-tag. The reactions of substrates with SNAP-tag were verified by kinetic analyses to enable the sequence-selective crosslinking reaction of MA. The new substrate enables the distinctive orthogonality of SNAP-tag against CLIP-tag to achieve orthogonal DNA-protein crosslinking by six unique MAs.

A ppm level Rh-based composite as an ecofriendly catalyst for transfer hydrogenation of nitriles: Triple guarantee of selectivity for primary amines

Hydrogenation of nitriles to afford amines under mild conditions is a challenging task with an inexpensive heterogeneous catalyst, and it is even more difficult to obtain primary amines selectively because of the accompanying self-coupling side reactions. An efficient catalytic system was designed as Fe3O4@nSiO2-NH2-RhCu@mSiO2 to prepare primary amines through the transfer hydrogenation of nitrile compounds with economical HCOOH as the hydrogen donor. The loading of rhodium in the catalyst could be at the ppm level, and the TOF reaches 6803 h-1 for Rh. This catalytic system has a wide substrate range including some nitriles that could not proceed in the previous literature. The experimental results demonstrate that the excellent selectivity for primary amines is guaranteed by three tactics, which are the strong active site, the inhibition of side products by the hydrogen source and the special pore structure of the catalyst. In addition, the catalyst could be reused ten times without activity loss through convenient magnetic recovery.

XANTHINE DERIVATIVES AND USES THEREOF AS INHIBITORS OF BROMODOMAINS OF BET PROTEINS

The present invention relates to a compound having the following formula (I): (I) wherein: - R is a (C1-C6)alkyl group;- R'' is preferably H;- Ar is a (C5-C12)arylene radical;- X1 is -C(=O)- or -SO2-; and- R' is chosen from the group consisting of possibly substituted (C1-C6)alkyl, heteroaryl, (C5-C12)aryl, and (hetero)cycloalkyl groups, or a pharmaceutically acceptable salt and/or tautomeric form thereof, or its racemates, diastereomers or enantiomers.

Green and convenient protocols for the efficient reduction of nitriles and nitro compounds to corresponding amines with NaBH4 in water catalyzed by magnetically retrievable CuFe2O4 nanoparticles

Abstract: In this study, firstly, CuFe2O4 nanoparticles were prepared by a simple operation. The structure of the mentioned nanoparticles was characterized by Fourier transform infrared spectroscopy, X-ray diffraction, scanning electron microscopy, transmission electron microscopy, energy-dispersive X-ray spectroscopy, inductively coupled plasma-optical emission spectrometry, vibrating sample magnetometer and also Brunauer–Emmett–Teller and Barrett–Joyner–Halenda analyses. The prepared magnetically copper ferrite nanocomposite was successfully applied as a simple, cost-effective, practicable, and recoverable catalyst on the green, highly efficient, fast, base-free, and ligand-free reduction of nitriles and also on the affordable and eco-friendly reduction of nitro compounds with the broad substrate scope to the corresponding amines with NaBH4 in water at reflux in high to excellent yields. Graphical abstract: [Figure not available: see fulltext.].

Switching the Selectivity of Cobalt-Catalyzed Hydrogenation of Nitriles

Previous studies of base metals for catalytic hydrogenation of nitriles to primary amines or secondary aldimines focus on designing complexes with elaborate structures. Herein, we report "twin" catalytic systems where the selectivity of nitrile hydrogenation can be tuned by including or omitting the ligand HN(CH2CH2PiPr2)2 (iPrPNHP). Simply treating CoBr2 with NaHBEt3 generates cobalt particles, which can catalyze the hydrogenation of nitriles to primary amines with high selectivity and broad functional group tolerance. Ligating CoBr2 with iPrPNHP followed by the addition of NaHBEt3, however, forms a homogeneous catalyst favoring secondary aldimines for both hydrogenation and hydrogenative coupling of benzonitrile.

Integrated Strategy for Lead Optimization Based on Fragment Growing: The Diversity-Oriented-Target-Focused-Synthesis Approach

Over the past few decades, hit identification has been greatly facilitated by advances in high-throughput and fragment-based screenings. One major hurdle remaining in drug discovery is process automation of hit-to-lead (H2L) optimization. Here, we report a time- and cost-efficient integrated strategy for H2L optimization as well as a partially automated design of potent chemical probes consisting of a focused-chemical-library design and virtual screening coupled with robotic diversity-oriented de novo synthesis and automated in vitro evaluation. The virtual library is generated by combining an activated fragment, corresponding to the substructure binding to the target, with a collection of functionalized building blocks using in silico encoded chemical reactions carefully chosen from a list of one-step organic transformations relevant in medicinal chemistry. The proof of concept was demonstrated using the optimization of bromodomain inhibitors as a test case, leading to the validation of several compounds with improved affinity by several orders of magnitude.

SUBSTITUTED PYRIDINES AS INHIBITORS OF DNMT1

The invention is directed to substituted pyridine derivatives. Specifically, the invention is directed to compounds according to Formula (Iar): (Iar) wherein Yar, X1ar, X2ar, R1ar, R2ar, R3ar, R4ar and R5ar are as defined herein; or a pharmaceutically acceptable salt or prodrug thereof. The compounds of the invention are selective inhibitors of DNMT1 and can be useful in the treatment of cancer, pre-cancerous syndromes, beta hemoglobinopathy disorders, sickle cell disease, sickle cell anemia, and beta thalassemia, and diseases associated with DNMT1 inhibition. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting DNMT1 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.