34231-22-6

Usage

Uses

Used in Pharmaceutical Research:
(3-(aminomethyl)phenyl)methanol is used as a starting material for the synthesis of pharmaceutical compounds, contributing to the development of new drugs and therapeutic agents.
Used in Organic Synthesis:
(3-(aminomethyl)phenyl)methanol is used as a versatile reagent for the preparation of a wide range of organic compounds, facilitating the creation of diverse chemical entities for various applications.
Used in Medicinal Chemistry:
(3-(aminomethyl)phenyl)methanol is used as a building block in the design and synthesis of heterocyclic compounds, which are often found in biologically active molecules and have potential applications in drug discovery.
Used in Drug Development:
(3-(aminomethyl)phenyl)methanol is utilized in the development of new drugs, playing a crucial role in advancing pharmaceutical research and the discovery of innovative therapeutic agents.

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

Upstream product

• 620-22-4 3-Methylbenzonitrile 
• 168761-51-1 4-chloro-7-ethylamino-6-nitroquinazoline 
• 28188-41-2 m-(bromomethyl)benzonitrile 
• 13531-48-1 methyl 3-cyanobenzoate 
• 1877-72-1 3-Cyanobenzoic acid 
• 221226-95-5 m-cyanobenzaldiacetate 
• 24964-64-5 3-Cyanobenzaldehyde 
• 323578-57-0 methanesulfonic acid 3-hydroxymethyl-benzyl ester 
• 626-18-6 1,3-dimethanol benzene 

Downstream Products

• 655251-01-7 C₁₉H₂₉N₃O₅ 
• 1253889-40-5 N⁽¹⁾-(4-butylphenyl)-N⁽²⁾-(3-(hydroxymethyl)benzyl)phthalamide 
• 1253889-47-2 N⁽¹⁾-(3,5-bis(trifluoromethyl)phenyl)-N⁽²⁾-(3-(hydroxymethyl)benzyl)phthalamide 
• 1313991-67-1 3-(((3S,6S,10aS)-6-((S)-2-(methylamino)propanamido)-5-oxodecahydropyrrolo[1,2-a]azocine-3-carboxamido)methyl)benzyl 3-oxobutanoate 
• 220364-34-1 tert-butyl (3-(bromomethyl)benzyl)carbamate 
• 1300730-20-4 C₁₂H₁₅NO₃ 
• 1112172-80-1 methyl trans-4-((5-(2-((3-(hydroxymethyl)benzyl)carbamoyl)-6-methylpyridin-4-yl)-2H-tetrazol-2-yl)methyl)cyclohexanecarboxylate 
• 1112171-83-1 N-(3-hydroxymethyl-benzyl)-4-(2-((trans-4-acetylamino-cyclohexyl)methyl)-2H-tetrazol-5-yl)-6-methyl-picolinamide 
• 86207-88-7 3-(p-nitrobenzyloxycarbonyl)aminomethylbenzyl alcohol 
• 916794-55-3 Biphenyl-2-ylcarbamic acid 1-[2-(3-hydroxymethylbenzylcarbamoyl)ethyl]piperidin-4-yl Ester 
• 655251-04-0 C₂₀H₃₁N₃O₇S 

Relevant academic research and scientific papers

BICYCLIC COMPOUNDS

Provided herein are compounds and pharmaceutical compositions comprising said compounds that are useful for treating cancers. Specific cancers include those that are mediated by YAP/TAZ or those that are modulated by the interaction between YAP/TAZ and TEAD.

LIBRARIES OF PYRIDINE-CONTAINING MACROCYCLIC COMPOUNDS AND METHODS OF MAKING AND USING THE SAME

The present disclosure relates to novel pyridine-containing macrocyclic compounds and libraries thereof that are useful as research tools for drug discovery efforts. This disclosure also relates to methods of preparing these compounds and libraries and methods of using these libraries, such as in high throughput screening. In particular, these libraries are useful for evaluation of bioactivity at existing and newly identified pharmacologically relevant targets, including G protein-coupled receptors, nuclear receptors, enzymes, ion channels, transporters, transcription factors, protein-protein interactions and nucleic acid-protein interactions. As such, these libraries can be applied to the search for new pharmaceutical agents for the treatment and prevention of a range of medical conditions.

Photoinduced charge transfer in a conformational switching chlorin dimer-azafulleroid in polar and nonpolar media

In the present study, a biomimetic reaction center model, that is, a molecular triad consisting of a chlorin dimer and an azafulleroid, is synthesized and its photophysical properties are studied in comparison with the corresponding molecular dyad, which consists only of a chlorin monomer and an azafulleroid. As evidenced by 1H NMR, UV/Vis, and fluorescence spectroscopy, the chlorin dimer-azafulleroid folds in nonpolar media into a C2-symmetric geometry through hydrogen bonding, resulting in appreciable electronic interactions between the chlorins, whereas in polar media the two chlorins diverge from contact. Femtosecond transient absorption spectroscopy studies reveal longer charge-separated states for the chlorin dimer-azafulleroid; 1.6 ns in toluene, compared with the lifetime of ≈0.9 ns for the corresponding chlorin monomer-azafulleroid in toluene. In polar media, for example, benzonitrile, similar charge-separated states are observed, but the lifetimes are inevitably shorter: 65 and 73 ps for the dimeric and monomeric chlorin-azafulleroids, respectively. Nanosecond transient absorption and singlet oxygen phosphorescence studies corroborate that in toluene, the charge-separated state decays indirectly via the triplet excited state to the ground state, whereas in benzonitrile, direct recombination to the ground state is observed. Complementary DFT studies suggest two energy-minima conformations, that is, a folded chlorin dimer-azafulleroid, which is present in nonpolar media, and another conformation in polar media, in which the two hydrophobic chlorins wrap the azafulleroid. Inspection of the frontier molecular orbitals shows that in the folded conformation, the HOMO on each chlorin is equivalent and is shared owing to partial π-π overlap, resulting in delocalization of the conjugated π electrons, whereas the wrapped conformation lacks this stabilization. As such, the longer charge-separated lifetime for the dimer is rationalized by both the electron donor-acceptor separation distance and the stabilization of the radical cation through delocalization. The chlorin folding seems to change the photophysical properties in a manner similar to that observed in the chlorophyll dimer in natural photosynthetic reaction centers.

Structure-guided, single-point modifications in the phosphinic dipeptide structure yield highly potent and selective inhibitors of neutral aminopeptidases

Seven crystal structures of alanyl aminopeptidase from Neisseria meningitides (the etiological agent of meningitis, NmAPN) complexed with organophosphorus compounds were resolved to determine the optimal inhibitor-enzyme interactions. The enantiomeric phosphonic acid analogs of Leu and hPhe, which correspond to the P1 amino acid residues of well-processed substrates, were used to assess the impact of the absolute configuration and the stereospecific hydrogen bond network formed between the aminophosphonate polar head and the active site residues on the binding affinity. For the hPhe analog, an imperfect stereochemical complementarity could be overcome by incorporating an appropriate P1 side chain. The constitution of P1′-extended structures was rationally designed and the lead, phosphinic dipeptide hPhePψ[CH2]Phe, was modified in a single position. Introducing a heteroatom/heteroatom-based fragment to either the P1 or P1′ residue required new synthetic pathways. The compounds in the refined structure were low nanomolar and subnanomolar inhibitors of N. meningitides, porcine and human APNs, and the reference leucine aminopeptidase (LAP). The unnatural phosphinic dipeptide analogs exhibited a high affinity for monozinc APNs associated with a reasonable selectivity versus dizinc LAP. Another set of crystal structures containing the NmAPN dipeptide ligand were used to verify and to confirm the predicted binding modes; furthermore, novel contacts, which were promising for inhibitor development, were identified, including a π-π stacking interaction between a pyridine ring and Tyr372.

Selective targeting of dendritic cell-specific intercellular adhesion molecule-3-grabbing nonintegrin (Dc-Sign) with mannose-based glycomimetics: Synthesis and interaction studies of bis(benzylamide) derivatives of a pseudomannobioside

Dendritic cell-specific intercellular adhesion molecule-3-grabbing nonintegrin (DC-SIGN) and Langerin are C-type lectins of dendritic cells (DCs) that share a specificity for mannose and are involved in pathogen recognition. HIV is known to use DC-SIGN on DCs to facilitate transinfection of T-cells. Langerin, on the contrary, contributes to virus elimination; therefore, the inhibition of this latter receptor is undesired. Glycomimetic molecules targeting DC-SIGN have been reported as promising agents for the inhibition of viral infections and for the modulation of immune responses mediated by DC-SIGN. We show here for the first time that glycomimetics based on a mannose anchor can be tuned to selectively inhibit DC-SIGN over Langerin. Based on structural and binding studies of a mannobioside mimic previously described by us (2), a focused library of derivatives was designed. The optimized synthesis gave fast and efficient access to a group of bis(amides), decorated with an azide-terminated tether allowing further conjugation. SPR inhibition tests showed improvements over the parent pseudomannobioside by a factor of 3-4. A dimeric, macrocyclic structure (11) was also serendipitously obtained, which afforded a 30-fold gain over the starting compound (2). The same ligands were tested against Langerin and found to exhibit high selectivity towards DC-SIGN. Structural studies using saturation transfer difference NMR spectroscopy (STD-NMR) were performed to analyze the binding mode of one representative library member with DC-SIGN. Despite the overlap of some signals, it was established that the new ligand interacts with the protein in the same fashion as the parent pseudodisaccharide. The two aromatic amide moieties showed relatively high saturation in the STD spectrum, which suggests that the improved potency of the bis(amides) over the parent dimethyl ester can be attributed to lipophilic interactions between the aromatic groups of the ligand and the binding site of DC-SIGN. Receptor targeting: For the first time glycomimetics based on a mannose anchor have been tuned to selectively inhibit DC-SIGN (dendritic cell-specific intercellular adhesion molecule-3-grabbing nonintegrin) over Langerin. Based on structural and binding studies of a mannobioside mimic previously described, a focused library of derivatives was designed (see figure). Copyright

Rhodium-catalyzed asymmetric hydrogenation of olefins with PhthalaPhos, a new class of chiral supramolecular ligands

A library of 19 binol-derived chiral monophosphites that contain a phthalic acid diamide group (Phthala- Phos) has been designed and synthesized in four steps. These new ligands were screened in the rhodium-catalyzed enantioselective hydrogenation of prochiral dehydroamino esters and enamides. Several members of the library showed excellent enantioselectivity with methyl 2-acetamido acrylate (6 ligands gave >97% ee), methyl (Z)-2- acetamido cinnamate (6 ligands gave >94% ee), and N-(1-phenylvinyl)acetamide (9 ligands gave >95% ee), whilst only a few representatives afforded high enantioselectivities for challenging and industrially relevant substrates N-(3,4-dihydronaphthalen-1- yl)-acetamide (96% ee in one case) and methyl (E)-2-(acetamidomethyl)-3- phenylacrylate (99% ee in one case). In most cases, the new ligands were more active and more stereoselective than their structurally related monodentate phosphites (which are devoid of functional groups that are capable of hydrogen-bonding interactions). Control experiments and kinetic studies were carried out that allowed us to demonstrate that hydrogen-bonding interactions involving the diamide group of the PhthalaPhos ligands strongly contribute to their outstanding catalytic properties. Computational studies carried out on a rhodium precatalyst and on a conceivable intermediate in the hydrogenation catalytic cycle shed some light on the role played by hydrogen bonding, which is likely to act in a substrate-orientation effect.

IMIDAZOLE DERIVATIVES AS IDO INHIBITORS

Presently provided are IDO inhibitors of general formulae (VII), (VIII) as shown below and pharmaceutical compositions thereof, useful for modulating an activity of indoleamine 2,3-dioxygenase; treating indoleamine 2,3-dioxygenase (IDO) mediated immunosuppression; treating a medical conditions that benefit from the inhibition of enzymatic activity of indoleamine-2,3-dioxygenase; enhancing the effectiveness of an anti-cancer treatment comprising administering an anti-cancer agent; treating tumor-specific immunosuppression associated with cancer; and treating immunosupression associated with an infectious disease.

General base-guanidinium cooperation in bifunctional artificial phosphodiesterases

Artificial phosphodiesterases that combine a guanidinium unit with a general base connected by a m-xylylene linker catalyze the transesterification of the RNA model compound 2-hydroxypropyl p-nitrophenyl phosphate (HPNP). The bifunctional catalysts presented in this work show varying extents of cooperation between catalytic units and a rate enhancement of 4 ×10 4 in the most favorable case.

Control of chemoselectivity in hydrogenations of substituted nitro- and cyano-aromatics by cluster-derived ruthenium nanocatalysts

Catalyst precursors 1 and 2, made by ion-pairing [H3Ru 4(CO)12]- with NR4+ groups of functionalized MCM-41 and water-soluble poly(diallyldimethylammonium chloride), PDADMAC, respectively, have been evaluated for the chemoselective hydrogenation of nitro- and cyano-benzaldehydes. They are found to be inert toward -NO2 and -CN groups, but active for the reduction of -CHO and >C=C4 (3) or with (5%)Ru-Al2O3, where both the functional groups are hydrogenated. Kinetic analyses have been carried out for the hydrogenation of 4-nitrobenzaldehyde with 2. Existence of an induction time and two competitive equilibriums followed by the product-forming rate-determining step are inferred from the empirically derived rate expression. The kinetic results, structural evidences, and previous work strongly suggest that the observed chemoselectivity is probably a result of the absence of multiple crystal planes, differing in Miller indices, in the cluster-derived catalysts.

Phthalaphos: Chiral supramolecular ligands for enantioselective rhodium-catalyzed hydrogenation reactions

Interligand hydrogen bonding of chiral monodentate phosphite ligands bearing H-bond donor and acceptor groups leads to formation of supramolecular bidentate ligands, rhodium complexes of which (see picture) afford excellent enantiomeric excesses in catalyzed hydrogenation of classical benchmark and industrially relevant substrates. cod=1,5-cyclooctadiene.