10239-34-6

Usage

Uses

N,N''-Dibenzyl-1,3-diaminopropane is a hepatitis C virus inhibitor.

Upstream product

• 63674-16-8 N,N'-bisbenzylidene-1,3-diaminopropane 
• 109-64-8 1,3-dibromo-propane 
• 100-46-9 benzylamine 
• 100-44-7 benzyl chloride 
• 109-76-2 Trimethylenediamine 
• 63674-16-8 N,N'-Bis-[1-phenyl-meth-(E)-ylidene]-propane-1,3-diamine 
• 68388-03-4 N,N'-(propane-1,3-diyl)dibenzamide 
• 100-52-7 benzaldehyde 
• 98-88-4 benzoyl chloride 
• 102950-52-7 1,3-dibenzyl-2-phenyl-hexahydro-pyrimidine 
• 100-39-0 benzyl bromide 
• 921-01-7 rac-cysteine 
• 1606142-71-5 N,N'-(propane-1,3-diyl)bis(N-benzyl-2,4-dinitrobenzenesulfonamide) 

Downstream Products

• 124105-89-1 2-benzo[1,3]dioxol-5-yl-1,3-dibenzyl-hexahydro-pyrimidine 
• 102949-61-1 1,3-dibenzyl-2-(4-chloro-phenyl)-hexahydro-pyrimidine 
• 102946-39-4 acetic acid-[4-(1,3-dibenzyl-hexahydro-pyrimidin-2-yl)-anilide] 
• 102950-52-7 1,3-dibenzyl-2-phenyl-hexahydro-pyrimidine 
• 141070-32-8 1,3-Dibenzyl-2-pyridin-3-yl-hexahydro-pyrimidine 
• 107886-56-6 N,N'-dibenzyl-N-(3-phthalimidopropyl)-1,3-diaminopropane 
• 138034-80-7 (+/-)-tert-butyl 1,4-dibenzyl-1,4-diazepane-2-carboxylate 
• 132206-16-7 1,3-Dibenzyl-2-(4,4-dimethyl-2,6-dioxocyclohexylidene)hexahydropyrimidine 
• 97095-67-5 1,3-dibenzyl-2-chlorohexahydro-1,3,2-diazaphosphorine 
• 102292-16-0 C₃₉H₅₀N₂O₂ 
• 78134-06-2 N,N'-dibenzyl-perhydrodiazepine-2,3-dione 
• 217973-32-5 C₁₇H₂₀N₄O₂ 
• 259656-89-8 (2R,10R)-bis(trifluoromethanesulfonyl)-N⁴,N⁸-dibenzyl-N¹,N¹¹-diethyl-2,10-dihydroxy-N¹,N¹¹-norspermine 
• 259656-76-3 (2S,10S)-N¹,N¹¹-bis(p-toluenesulfonyl)-N⁴,N⁸-dibenzyl-N¹,N¹¹-diethyl-2,10-dihydroxynorspermine 

Relevant academic research and scientific papers

A minimalistic approach to develop new anti-apicomplexa polyamines analogs

The development of new chemical entities against the major diseases caused by parasites is highly desired. A library of thirty diamines analogs following a minimalist approach and supported by chemoinformatics tools have been prepared and evaluated agains

Novel bis-arylalkylamines as myeloperoxidase inhibitors: Design, synthesis, and structure-activity relationship study

Human myeloperoxidase (MPO) plays an important role in innate immunity but also aggravates tissue damage by oxidation of biomolecules at sites of inflammation. As a result from a recent high-throughput virtual screening approach for MPO inhibitors, bis-2,2′-[(dihydro-1,3(2H,4H) pyrimidinediyl)bis(methylene)]phenol was detected as a promising lead compound for inhibition of the MPO-typical two-electron oxidation of chloride to hypochlorous acid (IC50= 0.5 μM). In the present pharmacomodulation study, 37 derivatives of this lead compound were designed and synthesized driven by comprehensive docking studies and the impact on the chlorination activity of MPO. We describe the structural requirements for optimum (i) binding to the heme periphery and (ii) inhibition capacity. Finally, the best three inhibitors (bis-arylalkylamine derivatives) were probed for interaction with the MPO redox intermediates Compound I and Compound II. Determined apparent bimolecular rate constants together with determination of reduction potential and nucleophilicity of the selected compounds allowed us to propose a mechanism of inhibition. The best inhibitor was found to promote the accumulation of inactive form of MPO-Compound II and has IC50= 54 nM, demonstrating the successful approach of the drug design. Due to the similarity of ligand interactions between MPO and serotonine transporter, the selectivity of this inhibitor was also tested on the serotonin transporter providing a selectivity index of 14 (KiSERT/IC50MPO).

Synthesis and investigation of new cyclic haloamidinium salts

The presented work describes the synthesis of new six- and seven-membered haloamidinium salts and their reaction with different metals. The isolated metal complexes were tested in a catalytic reaction. Two different synthetic routes were applied to prepare five different salts. Chloroamidinium salts were very water-sensitive in comparison to their corresponding bromoamidinium salts. Hence, the preparation of the less sensitive bromoamidinium salts was higher prioritized. The formed salts were converted with metal sources to N-heterocyclic carbene (NHC) metal complexes through an oxidative insertion into the C-X bond. This type of formation is less examined for the synthesis of extended NHC metal complexes. Pd(PPh3)4 and cobalt powder were applied as metal sources, whereby two palladium complexes were isolated, characterized, and their crystal and molecular structures determined. The palladium complexes were investigated in the Suzuki-Miyaura reaction and showed promising catalytic activity.

Thiol activated prodrugs of sulfur dioxide (SO2) as MRSA inhibitors

Drug resistant infections are becoming common worldwide and new strategies for drug development are necessary. Here, we report the synthesis and evaluation of 2,4-dinitrophenylsulfonamides, which are donors of sulfur dioxide (SO2), a reactive sulfur species, as methicillin-resistant Staphylococcus aureus (MRSA) inhibitors. N-(3-Methoxyphenyl)-2,4-dinitro-N-(prop-2-yn-1-yl)benzenesulfonamide (5e) was found to have excellent in vitro MRSA inhibitory potency. This compound is cell permeable and treatment of MRSA cells with 5e depleted intracellular thiols and enhanced oxidative species both results consistent with a mechanism involving thiol activation to produce SO2.

INHIBITORS OF THE RENAL OUTER MEDULLARY POTASSIUM CHANNEL

The present invention provides compounds of Formula I and the pharmaceutically acceptable salts thereof, which are inhibitors of the ROMK (Kirl.1) channel. The compounds may be used as diuretic and/or natriuretic agents and for the therapy and prophylaxis of medical conditions including cardiovascular diseases such as hypertension, heart failure and conditions associated with excessive salt and water retention.

Synthesis and evaluation of hexahydropyrimidines and diamines as novel hepatitis C virus inhibitors

In order to identify novel anti-hepatitis C virus (HCV) agents we devised cell-based strategies and screened phenotypically small molecule chemical libraries with infectious HCV particles, and identified a hit compound (1) containing a hexahydropyrimidine (HHP) core. During our cell-based SAR study, we observed a conversion of HHP 1 into a linear diamine (6), which is the active component in inhibiting HCV and exhibited comparable antiviral activity to the cyclic HHP 1. In addition, we engaged into the biological characterization of HHP and demonstrated that HHP does not interfere with HCV RNA replication, but with entry and release of viral particles. Here we report the results of the preliminary SAR and mechanism of action studies with HHP.

The effect of the nitrogen non-bonding electron pair on the NMR and X-ray in 1,3-diazaheterocycles

The effect of the nitrogen nonbonding electron pair on the 1JC,H values of 1,3-diazaheterocycles was analyzed and compared to 1,5-diazabiciclo[3.2.1]octanes, which have a restricted conformation. The 1JC,H values were measured by observing the 13C satellites in the 1H NMR spectra and then determining the 1H-coupled 13C NMR spectra. The 1JC,H values are 10 Hz larger when the α-hydrogen is synperiplanar rather than antiperiplanar to the nonbonding electron pair on the nitrogen, which serves as experimental evidence of the orbital n N→σC,Hap interactions. In addition, the homoanomeric effect from the interactions of the nitrogen lone pair with the antibonding orbital of the equatorial hydrogen, which was in the β position, was discussed (nN→σC(β),H eq).

Synthesis and antikinetoplastid activity of a series of N,N×-substituted diamines

A series of 25 N,N×-substituted diamines were prepared by controlled reductive amination of free aliphatic diamines with different substituted benzaldehydes. The library was screened in vitro for antiparasitic activity on the causative agents of human Afr

Reversible aminal formation: Controlling the evaporation of bioactive volatiles by dynamic combinatorial/covalent chemistry

Dynamic mixtures generated by reversible aminal formation efficiently prolong the duration of evaporation of bioactive volatile aldehydes. Secondary diamines used for the generation of dynamic mixtures are obtained by treatment of primary diamines with carbonyl compounds and reduction of the diimines with NaBH4. The reversibilities of the reactions were demonstrated by NMR measurements in buffered aqueous solutions. Kinetic rate constants and equilibrium constants for the formation and hydrolysis of aminals were determined. The performance of dynamic mixtures as delivery systems for perfumery ingredients was tested after deposition onto cotton, and the long-lastingness of fragrance evaporation was investigated by dynamic headspace analysis against a reference sample. The simplicity of the concept together with its excellent performance makes this delivery system highly interesting for applied perfumery. Reversible aminal formation might also be successfully applicable to dynamic combinatorial/covalent chemistry for screening of pharmaceutically or catalytically active ligands and receptors. The evaporation of bioactive volatiles that are emitted from flowers to attract insects and that are used as fragrances in our everyday life is limited in time. Dynamic mixtures obtained by reversible aminal formation of suitably designed diamines with volatile aldehydes prolong the perception of these compounds in functional perfumery.

Reversible formation of aminals: A new strategy to control the release of bioactive volatiles from dynamic mixtures

Dynamic mixtures generated by reversible aminal formation of fragrance aldehydes with N,N′-dibenzyl alkyldiamines in aqueous systems were found to be suitable delivery systems for the controlled release of bioactive volatiles. The Royal Society of Chemistry 2010.