13910-48-0

Usage

Uses

Used in Pharmaceutical Industry:
3-(Benzylamino)propylamine is utilized as an intermediate in the synthesis of various pharmaceuticals and organic compounds. Its unique chemical structure allows it to serve as a building block for the development of new drugs and medicinal agents, contributing to the advancement of treatments for a range of health conditions.
Used in Organic Compounds Synthesis:
In the field of organic chemistry, 3-(Benzylamino)propylamine is employed as a key intermediate for the production of diverse organic compounds. Its reactivity and solubility properties make it a valuable component in the synthesis processes, facilitating the creation of complex molecules with specific functions and applications.

InChI:InChI=1/C10H16N2/c11-7-4-8-12-9-10-5-2-1-3-6-10/h1-3,5-6,12H,4,7-9,11H2

Upstream product

• 706-03-6 3-(benzylamino)propionitrile 
• 107-13-1 acrylonitrile 
• 100-46-9 benzylamine 
• 42245-33-0 N-benzyl-3-chloropropylamine 
• 109-76-2 Trimethylenediamine 
• 103-67-3 benzyl-methyl-amine 
• 87142-90-3 N¹-[1-Phenyl-meth-(E)-ylidene]-propane-1,3-diamine 
• 100-52-7 benzaldehyde 
• 100-44-7 benzyl chloride 
• 1111644-29-1 N-(3-benzylaminopropyl)-N'-(3-ethylaminopropyl)butane-1,4-diamine 
• 117654-79-2 1,14-bis(phenylmethyl)-1,5,10,14-tetraazatetradecane tetrahydrochloride 
• 107-15-3 ethylenediamine 
• 1111643-89-0 N⁽¹⁾-benzyl-N⁽¹⁾,N⁽³⁾-bis(2-nitrobenzenesulfonyl)propane-1,3-diamine 

Downstream Products

• 61797-12-4 Undec-10-enoic acid benzyl-(3-undec-10-enoylamino-propyl)-amide 
• 46465-08-1 3-Benzylamino-propylguanidin 
• 1602-94-4 1-benzyl-1,4,5,6-tetrahydropyrimidine 
• 571178-26-2 5-[1-(3-benzylaminopropylamino)ethylidene]-1,3-dimethylhexahydro-2,4,6-pyrimidinetrione 
• 90914-13-9 N⁴-Benzyl-N¹-(tert-butoxycarbonyl)norspermidine 
• 90914-10-6 N--N-(2-cyanoethyl)benzylamine 
• 90914-14-0 N⁴-Benzyl-N¹-(tert-butoxycarbonyl)spermidine 
• 90914-16-2 N⁴-Benzyl-N¹-(tert-butoxycarbonyl)-N⁷-(trifluoroacetyl)norspermidine 
• 90914-17-3 N⁴-Benzyl-N¹-(tert-butoxycarbonyl)-N⁸-(trifluoroacetyl)spermidine 
• 108992-03-6 1-benzyl-2-chloromethyl-1,4,5,6-tetrahydro-pyrimidine; hydrochloride 
• 61532-80-7 1-benzyl-2-nitromethylene-hexahydro-pyrimidine 
• 109-76-2 Trimethylenediamine 
• 3436-51-9 2,7-bis-[3-(benzylamino)propyl]benzo[lmn][3,8]phenanthroline-1,3,6,8-tetraone 

Relevant academic research and scientific papers

Low emission epoxy resin composition

An epoxy resin composition, the curing components of which contain at least one amine of formula (I) and optionally at least one amine A which is, in particular, an adduct of a polyamine and an epoxide. The amine for formula (I) is used in particular in the form of a reaction product of the reductive alkylation of 1,2-ethylenediamine and an aldehyde or ketone. The epoxy resin composition is used in particular as a low-emission, room-temperature-curing epoxy-resin coating. It is characterised by good processibility, quick curing, high hardness, a nice surface and a low tendency to yellowing.

A new kind of acetylcholine esterase inhibitors and its preparation method and application (by machine translation)

The present invention provides a novel acetyl choline esterase inhibitor and its preparation method and application, in particular, the invention discloses a formula A shown with double AChE binding site of substituted acridine compound, and its preparation method and as acetylcholinesterase inhibitors. The preparation of the novel compounds of this invention demonstrate good inhibit acetylcholine esterase role, can be used as a preparation for treating and preventing HAMER (AD) application value. (by machine translation)

Structure-activity relationships of novel substituted naphthalene diimides as anticancer agents

Novel 1,4,5,8-naphthalenetetracarboxylic diimide (NDI) derivatives were synthesized and evaluated for their antiproliferative activity on a wide number of different tumor cell lines. The prototypes of the present series were derivatives 1 and 2 characterized by interesting biological profiles as anticancer agents. The present investigation expands on the study of structure-activity relationships of prototypes 1 and 2, namely, the influence of the different substituents of the phenyl rings on the biological activity. Derivatives 3-22, characterized by a different substituent on the aromatic rings and/or a different chain length varying from two to three carbon units, were synthesized and evaluated for their cytostatic and cytotoxic activities. The most interesting compound was 20, characterized by a linker of three methylene units and a 2,3,4-trimethoxy substituent on the two aromatic rings. It displayed antiproliferative activity in the submicromolar range, especially against some different cell lines, the ability to inhibit Taq polymerase and telomerase, to trigger caspase activation by a possible oxidative mechanism, to downregulate ERK 2 protein and to inhibit ERKs phosphorylation, without acting directly on microtubules and tubuline. Its theoretical recognition against duplex and quadruplex DNA structures have been compared to experimental thermodynamic measurements and by molecular modeling investigation leading to putative binding modes. Taken together these findings contribute to define this compound as potential Multitarget-Directed Ligands interacting simultaneously with different biological targets.

Metabolism of N-alkylated spermine analogues by polyamine and spermine oxidases

N-alkylated polyamine analogues have potential as anticancer and antiparasitic drugs. However, their metabolism in the host has remained incompletely defined thus potentially limiting their utility. Here, we have studied the degradation of three different spermine analogues N,N′-bis-(3-ethylaminopropyl)butane-1,4-diamine (DESPM), N-(3-benzyl-aminopropyl)-N′-(3-ethylamino-propyl)butane-1,4-diamine (BnEtSPM) and N,N′-bis-(3-benzylaminopropyl)butane-1,4-diamine (DBSPM) and related mono-alkylated derivatives as substrates of recombinant human polyamine oxidase (APAO) and spermine oxidase (SMO). APAO and SMO metabolized DESPM to EtSPD [Km(APAO) = 10 μM, kcat(APAO) = 1.1 s -1 and Km(SMO) = 28 μM, kcat(SMO) = 0.8 s-1, respectively], metabolized BnEtSPM to EtSPD [Km(APAO) = 0.9 μM, kcat(APAO) = 1.1 s-1 and Km(SMO) = 51 μM, kcat(SMO) = 0.4 s-1, respectively], and metabolized DBSPM to BnSPD [Km(APAO) = 5.4 μM, k cat(APAO) = 2.0 s-1and Km(SMO) = 33 μM, kcat(SMO) = 0.3 s-1, respectively]. Interestingly, mono-alkylated spermine derivatives were metabolized by APAO and SMO to SPD [EtSPM Km(APAO) =16 μM, kcat(APAO) = 1.5 s -1; Km(SMO) = 25 μM, kcat(SMO) = 8.2 s -1; BnSPM Km(APAO) = 6.0 μM, kcat(APAO) = 2.8 s-1; Km(SMO) =19 μM, kcat(SMO) = 0.8 s-1, respectively]. Surprisingly, EtSPD [Km(APAO) = 37 μM, kcat(APAO) = 0.1 s-1; Km(SMO) =48 μM, kcat(SMO) = 0.05 s-1] and BnSPD [Km(APAO) = 2.5 μM, kcat(APAO) = 3.5 s-1; Km(SMO) =60 μM, kcat(SMO) = 0.54 s-1] were metabolized to SPD by both the oxidases. Furthermore, we studied the degradation of DESPM, BnEtSPM or DBSPM in the DU145 prostate carcinoma cell line. The same major metabolites EtSPD and/or BnSPD were detected both in the culture medium and intracellularly after 48 h of culture. Moreover, EtSPM and BnSPM were detected from cell samples. Present data shows that inducible SMO parallel with APAO could playanimportant roleinpolyamine based drug action, i.e. degradation of parent drug and its metabolites, having significant impact on efficiency of these drugs, and hence for the development of novel N-alkylated polyamine analogues. Springer-Verlag 2009.

One step from nitro to oxime: a convenient preparation of unsaturated oximes by the reduction of the corresponding vinylnitro compounds

A series of novel unsaturated oximes were conveniently prepared from the corresponding vinylnitro compounds by reduction with SnCl2·2H2O. The structures of the oximes were characterized by 1H and 13C NMR, IR and HRMS, and X-ray crystallography analysis of 1-(6-chloro-pyridin-3-ylmethyl)-4,5-dihydro-1H-imidazole-2-carbaldehyde oxime 2a reveals that, the hydroxyl group is arranged in a trans configuration. Some evidences from a brief investigation suggest that these oximes seem to be formed by reduction of the aci form of nitro aliphatic compounds.

Naphthyridine-based helical foldamers and macrocycles: Synthesis, cation binding, and supramolecular assemblies

(Figure Presented) Unraveling the factors that control the conformation of molecular chains is of great interest both for understanding the shape of biological molecular strands and for designing artificial ones that adopt desired forms. Thus, a variety of artificial folding codons have been identified that enforce the formation, among others, of helices, strands, and loops, the major emphasis being on the shape of the foldamer. We report herein the synthesis and study of a family of foldamers and macrocycles based on the 1,8-naphthyridine and pyrimidine units, whose internal cavity is large enough to accommodate ionic substrates, and focus on the impact of guest binding within a cylindrical environment. Interestingly, the binding event within these large oligomers is translated to the outside of the receptors and affects the interaction of the overall complexes with the outside world. For instance, alkali cations bind to the one-turn helices and macrocycles to promote fibril formation and aggregation. Also, polyammonium substrates are able to tune the length of the overall helix assemblies and the rigidity of long oligomers. The reported data on one-turn, two-turn helices and macrocycles not only allows one to devise a model for the ion-controlled supramolecular assembly of such systems but also provides evidence that such controlled scaffolds bear promise in the design of complex systems.

Synthesis of platinum complexes from N-benzyl-1,3-propanediamine derivatives, potential antineoplastic agents

This work describes the synthesis of seven new platinum complexes having N-benzyl 1,3-propanediamine derivatives as ligands. They were prepared by the reaction of K2[PtCl4] with the appropriate ligand in water. These complexes are an

Modular fluorescence sensors for saccharides

Modular photoinduced electron transfer (PET) sensors bearing two phenylboronic acid groups, a pyrene group and alkylene linkers, from trimethylene to octamethylene, have been prepared and evaluated. The diboronic acid systems with tetramethylene 34 pentamethylene 35 and hexamethylene 36 linkers display the greatest enhancement in binding relative to monoboronic acid 4 with D-glucose. The diboronic acid system with the hexamethylene 36 linker is particularly D-glucose selective and sensitive. Whilst the diboronic acid systems with the longer heptamethylene 37 and octamethylene 38 linkers display the greatest enhancement in binding relative to monoboronic acid 4 with D-galactose. All saccharide titrations were performed in methanolic aqueous solution.

Rapid synthesis of large enaminolactams, a novel class of macrocycles

An efficient preparation of enaminolactams using an original synthetic method based on the thermal decomposition of Meldrum's acids derivatives is reported. The key step involves an intramolecular addition of ω-aminoalkyl- aminomethyleneketenes.

Synthesis and antihypertensive activity of a series of 4-amino-6,7-dimethoxyquinazoline derivatives

A series of N2-[(acylamino)alkyl]-6,7-dimethoxy-2,4-quinazolinediamines was synthesized as potential α1-adrenoceptor antagonists. When administered to spontaneously hypertensive rats at 10 mg/kg po, a number of propanediamine derivatives showed good antihypertensive activity, whereas the ethanediamine derivatives, albeit being structurally more closely related to prazosin, were devoid of this property. The most active derivative, N-[3-[(4-amino-6,7-dimethoxy-2-quinazolinyl)methylamino]propyl]tetrahydro- 2-furancarboxamide hydrochloride, alfuzosin, showed high selectivity for peripheral α1-postjunctional adrenoceptors. At equiactive antihypertensive doses, its effect on the pressor response to postural changes in conscious dog was less marked than that shown by prazosin. In the light of these results, alfuzosin was selected for clinical evaluation.