879-72-1

Usage

Chemical Properties

white crystalline powder

InChI:InChI=1/C11H15NO/c1-12(2)9-8-11(13)10-6-4-3-5-7-10/h3-7H,8-9H2,1-2H3/p+1

Upstream product

• 50599-78-5 4-dimethylamino-2-phenyl-butyronitrile 
• 50-00-0 formaldehyd 
• 506-59-2 N,N-dimethylammonium chloride 
• 98-86-2 acetophenone 
• 646-06-0 1,3-DIOXOLANE 
• 30354-18-8 N,N-dimethyl(methylene)ammonium chloride 
• 124-40-3 dimethyl amine 
• 110-88-3 1,3,5-Trioxan 
• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 

Downstream Products

• 124-40-3 dimethyl amine 
• 768-03-6 Phenyl vinyl ketone 
• 55563-72-9 3-methoxy-1-phenylpropan-1-one 
• 24070-51-7 β-iodopropiophenone 
• 46814-59-9 C₁₂H₁₉N₅ 
• 21787-15-5 4-[1-(3-oxo-3-phenyl-propyl)-pyrrolidin-3-yl]-4H-benzo[1,4]oxazin-3-one 
• 99060-13-6 β-Formylamino-propiophenon 
• 67961-02-8 6-ethyl-3-phenylcyclohex-2-enone 
• 59066-55-6 3-(methyl(phenyl)amino)-1-phenylpropan-1-one 
• 2538-44-5 3-(N-1,1-Diphenylmethylamino)-1-phenylpropan-1-on 
• 90548-69-9 3-dimethylamino-1-phenyl-2-(1-pyrrolidinylmethyl)-1-propanone dihydrobromide 
• 833-86-3 1-(phenyl)-3-(1'-pyrrolidin)propanone hydrochloride 
• 886-06-6 1-phenyl-3-piperidino-propan-1-one; hydrochloride 
• 142954-77-6 5-phenyl-4,7-dihydro-1,2,4-triazolo<1,5-a>pyrimidine 

Relevant academic research and scientific papers

Platinum and palladium complexes of tridentate ?C^N^N (phen-ide)-pyridine-thiazol ligands – A case study involving spectroelectrochemistry, photoluminescence spectroscopy and TD-DFT calculations

Four Pd(II) and Pt(II) complexes [M(C^N^N)Cl] (HC^N^N = 2-(6-phenylpyridin-2-yl)thiazoles) were synthesised, analysed and characterised using 1H NMR and MS in solution, as well as single crystal XRD in the solid. Cyclic voltammetry of the square planar complexes showed reversible or partially reversible reductions and irreversible oxidations. DFT calculations allowed assigning them to essentially metal-centred oxidations and ligand-centred reductions. Absorption spectra of the complexes show intense absorption bands into π-π* states in the UV to visible spectral range and long-wavelength bands which were assigned to transitions into mixed metal-to-ligand charge transfer (MLCT)/π-π* states, based on TD-DFT calculations. Comparison of Pt and Pd derivatives showed that the energy of the (MLCT)/π-π* bands are increased for Pd over Pt. This was also observed for the phosphorescence at 77 K and is attributed to the higher oxidation potential for Pd and supported by spectroelectrochemical measurements. The photoluminescence quantum yield (ΦL) drops drastically from Pt to Pd at room temperature, where only the two Pt(II) complexes are luminescent showing a broad unstructured phosphorescence from a 3MLCT state. At 77 K, the phosphorescence is blue-shifted and shows a clear vibrational progression, which is related to an enhanced ligand-centred character due to the lack of solvent stabilisation in the frozen matrix that otherwise increases the MLCT contribution. The Pd(II) complexes are not emissive at 298 K, but luminesce at 77 K. This is due to metal-centred dissociative d-d* states that facilitate radiationless deactivation, which cannot be thermally populated at low temperatures. Thus, similar ΦL are observed in frozen glassy matrices for both metals. TD-DFT calculations provided insight into the excited states and showed that the substitution pattern does not affect the emission, due to the lack of participation of the phenyl unit in the orbitals that are relevant for the description of the emissive state.

Synthesis of 4-(3-oxo-3-phenylpropyl)morpholin-4-ium chloride analogues and their inhibitory activities of nitric oxide production in lipopolysaccharide-induced BV2 cells

Based on our previous report that 3-morpholino-1-phenylpropan-1-one 2, one of the fluoxetine's simplified morpholino analogue, inhibited nitric oxide (NO) production, in this paper, various substituted benzene analogues with morpholine hydrochloride of 2 were synthesized and their inhibitory effects on NO production in lipopolysaccharide (LPS)-induced BV2 cells were tested. Among the synthesized compounds, 2-trifluoromethyl analogue 16n (IC50 = 8.6 μM) showed a significantly higher inhibitory activity than that of the parent compound 2a (IC50 > 50 μM) and suppressed NO production dose-dependently without cytotoxicity. Compound 16n also inhibited iNOS expression in LPS-induced BV2 cells at 2, 10 and 20 μM concentrations. These results suggest that compound 16n inhibited NO production by suppressing the expression of iNOS and can be used as a lead structure for developing new inhibitor of NO production.

1,2,4-Triazolo[1,5-a]pyrimidines: Efficient one-step synthesis and functionalization as influenza polymerase PA-PB1 interaction disruptors

In the search for new anti-influenza virus (IV) compounds, we have identified the 1,2,4-triazolo[1,5-a]pyrimidine (TZP) as a very suitable scaffold to obtain compounds able to disrupt IV RNA-dependent RNA polymerase (RdRP) PA-PB1 subunits heterodimerization. In this work, in order to acquire further SAR insights for this class of compounds and identify more potent derivatives, we designed and synthesized additional series of analogues to investigate the role of the substituents around the TZP core. To this aim, we developed four facile and efficient one-step procedures for the synthesis of 5-phenyl-, 6-phenyl- and 7-phenyl-2-amino-[1,2,4]triazolo[1,5-a]pyrimidines, and 2-amino-5-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-ol. Two analogues having the ethyl carboxylate moiety at the C-2 position of the TZP were also prepared in good yields. Then, the scaffolds herein synthesized and two previous scaffolds were functionalized and evaluated for their anti-IAV activity, leading to the identification of compound 22 that showed both anti-PA-PB1 (IC50 = 19.5 μM) and anti-IAV activity (EC50 = 16 μM) at non-toxic concentrations, thus resulting among the most active TZP derivatives reported to date by us. A selection of the synthesized compounds, along with a set of in-house available analogues, was also tested against SARS-CoV-2. The most promising compound 49 from this series displayed an EC50 value of 34.47 μM, highlighting the potential of the TPZ scaffold in the search for anti-CoV agents.

Fluoxetine scaffold to design tandem molecular antioxidants and green catalysts

Fluoxetine finds application in the treatment of depression and mood disorders. This selective serotonin-reuptake inhibitor (SSRI) also contrasts oxidative stress by direct ROS scavenging, modulation of the endogenous antioxidant defense system, and/or enhancement of the serotonin antioxidant capacity. We synthesised some fluoxetine analogues incorporating a selenium nucleus, thus expanding its antioxidant potential by enabling a hydroperoxides-inactivating, glutathione peroxidase (GPx)-like activity. Radical scavenging and peroxidatic activity were combined in a water-soluble, drug-like, tandem antioxidant molecule. Selenofluoxetine derivatives were reacted with H2O2in water, and the mechanistic details of the reaction were unravelled combining nuclear magnetic resonance (NMR), electrospray ionisation-mass spectrometry (ESI-MS) and quantum chemistry calculations. The observed oxidation-elimination process led to the formation of seleninic acid and cinnamylamine in atrans-selective manner. This mechanism is likely to be extended to other substrates for the preparation of unsaturated cinnamylamines.

Stereoselective Construction of γ-Lactams via Copper-Catalyzed Borylacylation

A versatile and highly stereoselective borylative cyclization to generate polyfunctionalized γ-lactams has been developed. The stereoselective synthesis of these key ring systems is crucial due to their ubiquity in natural products. We report the diastero- and enantioselective construction of di- and trisubstituted γ-lactam cores, with examples containing an enantioenriched quaternary carbon.

Structural, spectroscopic, Hirshfeld surface and charge distribution analysis of 3-(1H-imidazole-1-yl)-1-phenylpropan-1-ol complemented by molecular docking predictions: An integrated experimental and computational approach

The optimized structure of title compound 3-(1H-imidazole-1-yl)-1-phenylpropan-1-ol (3HIP) was predicted according to the density functional theory (DFT) using the B3LYP method with 6-311G (d,p) basis set. Computed structural parameters of 3HIP were compared with X-ray diffraction data. Recorded and computed wavenumbers were assigned according to the total energy distribution (TED) using VEDA software. The natural bond orbital (NBO) analysis was used to characterize intramolecular rehybridization and delocalization of the electron density within the title molecule. Predictions of the NMR (1H and 13C) chemical shift assignments obtained by applying the gauge including atomic orbital (GIAO) approach were consistent with the corresponding experimental values. Ultraviolet-visible spectra of the title compound were simulated and validated experimentally. A molecular electrostatic potential (MEP) diagram visualized the electrophilic and nucleophilic sites of the 3HIP molecule. Hirshfeld surface analysis assessed the potential interactions of each atom inside the 3HIP molecule. Moreover, molecular docking analysis simulated the potential binding site pose of 3HIP within the active site of its target protein. The resulting 3HIP–target protein model can provide guidance for the development of new potent antifungal treatments.

Spectral characterization, computed frequencies analysis and electronic structure calculations on (1E)–N-hydroxy-3-(1H-imidazol-1-yl)-1-phenylpropan-1-imine: An oxime-bearing precursor to potential antifungal agents

(1E)–N-Hydroxy-3-(1H-imidazol-1-yl)-1-phenylpropan-1-imine (H3IPI) is a precursor to potential antifungal agents and was subjected to experimental and simulated spectroscopic (UV, FT-IR, FT-Raman as well as 1H and 13C NMR) characterization. Density functional theory, Hartree-Fock fundamental wavenumbers and intensity of the modes are interpreted with the aid of structure optimizations and normal force field computations. The complete wavenumbers assignments of H3IPI were made on the basis of potential energy distribution of each vibrational mode. The electronic and excited state properties have been determined by time dependent-density functional theory method. The responsiveness parameters as chemical potential, global hardness, and electrophilicity index have also been calculated. The scaled B3LYP/6–311++G (d,p) calculations showed better coincidence with the experimental findings of H3IPI over the other computation method. Molecular electrostatic potential and thermodynamic properties of the title compound were also investigated. In addition, Mulliken and natural charges distribution, non-linear optics properties as well as natural bond orbital analysis of the title molecule were calculated and interpreted. Theoretical calculations of the NMR chemical shifts of H3IPI were carried out through GIAO method at B3LYP/6–311++G (d,p) level and the results were compared with the experimental values.

Design of two alternative routes for the synthesis of naftifine and analogues as potential antifungal agents

Two practical and efficient approaches have been implemented as alternative procedures for the synthesis of naftifine and novel diversely substituted analogues 16 and 20 in good to excellent yields, mediated by Mannich-type reactions as the key step of the processes. In these approaches, theγ-aminoalcohols 15 and 19 were obtained as the key intermediates and their subsequent dehydration catalyzed either by Br?nsted acids like H2SO4 and HCl or Lewis acid like AlCl3, respectively, led to naftifine, along with the target allylamines 16 and 20. The antifungal assay results showed that intermediates 18 (bearing both a β-aminoketo- and N-methyl functionalities in their structures) and products 20 were the most active. Particularly, structures 18b, 18c, and the allylamine 20c showed the lowest MIC values, in the 0.5-7.8 μg/mL range, against the dermatophytes Trichophyton rubrum and Trichophyton mentagrophytes. Interesting enough, compound 18b bearing a 4-Br as the substituent of the phenyl ring, also displayed high activity against Candida albicans and Cryptococcus neoformans with MIC80 = 7.8 μg/mL, being fungicide rather than fungistatic with a relevant MFC value = 15.6 μg/mL against C. neoformans.

3-[(BENZO[D][1,3]DIOXOLAN-4-YL)-OXY]-3-ARYLPROPYLAMINE TYPE COMPOUNDS AND APPLICATIONS THEREOF

The present invention relates to 3-[(benzo[d][1,3]dioxolan-4-yl)-oxy]-3-arylpropylamine compounds of formula I or pharmaceutically acceptable salts thereof and use thereof. The compound may be used to prepare an antidepressant agent.

Luminescent PtII Complexes of Tridentate Cyclometalating 2,5-Bis(aryl)-pyridine Ligands

Bis-cyclometalated PtII complexes of dianionic 2,5-bis(aryl)-pyridine ligands (L1–6)2–, carrying various cyclometalating or pending aryl groups, are synthesised in two steps. The reactions of H2L protoligands with K2[PtCl4] in acetic acid give the mono-cyclometalated complexes [Pt(HL)Cl]2. Heating these complexes in hot DMSO (dimethyl sulfoxide) yields the double-cyclometalated DMSO complexes [Pt(L1–6)(DMSO)]. The reaction of [Pt(L4)(DMSO)] with N,N-dimethylimidazolium iodide in the presence of KOtBu as the base gives the carbene complex [Pt(L4)(Me2Imd)]. Detailed photophysical studies reveal the intense orange luminescence of these complexes in CH2Cl2 solution, with quantum yields up to 0.22, and increased quantum yields of up to 1.00 in glassy frozen CH2Cl2/MeOH (1:1) and up to 0.44 in PMMA matrices. Detailed electrochemistry (including spectroelectrochemistry) reveals reversible ligand-based first reductions at –2.1 to –2.3 V, irreversible Pt-centred oxidations at around 0.8 V and electrochemical band gaps of 2.8–3.0 eV. Further reduction waves at very negative potentials interfere with the solvent (THF with traces of water) discharge and can be traced, with UV/Vis spectroelectrochemistry, to Pt-centred reductions for the DMSO complexes and to a second ligand-centred reduction for the Me2Imd complex from. The photo/electrochemical properties can be roughly correlated with the ligand pattern and suggest their use in optoelectronic applications.