102202-87-9

Upstream product

• 56-18-8 bis(3-aminopropyl)amine 
• 85-44-9 phthalic anhydride 
• 22509-74-6 N-ethoxycarbonylphthalimide 

Downstream Products

• 66322-78-9 N,N,N-tris(3-phthalimidopropyl)amine 
• 164913-26-2 N¹,N⁹-dibenzyl-N⁵,N¹³-ditosyl-1,5,9,13-tetraazacyclohexadecane 
• 1555-71-1 N1-(3-amino-propyl)-N1-benzyl-propane-1,3-diamine 
• 47771-56-2 N⁴-benzyl-N¹,N⁷-ditosyl-4-aza-1,7-heptanediamine 
• 313983-96-9 [4-({bis-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propyl]-carbamoyloxy}-methyl)-phenoxy]-acetic acid 
• 313983-90-3 [4-({bis-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propyl]-carbamoyloxy}-methyl)-phenoxy]-acetic acid allyl ester 
• 107886-36-2 N,N-bis(3-phthalimidopropyl)benzylamine 

Relevant academic research and scientific papers

Oligonucleotides Containing Aminated 2′-Amino-LNA Nucleotides: Synthesis and Strong Binding to Complementary DNA and RNA

Mono- and diaminated 2′-amino-LNA monomers were synthesized and introduced into oligonucleotides. Each modification imparts significant stabilization of nucleic acid duplexes and triplexes, excellent sequence selectivity, and significant nuclease resistance. Molecular modeling suggested that structural stabilization occurs via intrastrand electrostatic attraction between the protonated amino groups of the aminated 2′-amino-LNA monomers and the host oligonucleotide backbone.

Synthesis, cytotoxicity and cucurbituril binding of triamine linked dinuclear platinum complexes

The platinum complexes trans-[{PtCl(NH3)2} 2(μ-NH2(CH2)3NH 2(CH2)3NH2)]3+ (CT033) and the corresponding N4-dimethyl linked analogue trans-[{PtCl(NH 3)2}2(μ-NH2(CH2) 3N(Me)2(CH2)3NH2)] 3+ (CT233) have been synthesised, and their cytotoxicity, ability to bind cucurbit[7,8]uril (Q[7,8]) and reaction with cysteine studied. Both platinum complexes show good activity in the L1210 cell line and maintain their activity in the corresponding cisplatin L1210/DDP cell line. However, the N4-dimethyl analogue CT233 is approximately 50-times less active than the CT033 complex. This suggests that the insertion of a positive charge into the linking ligand may not, per se, be responsible for the higher cytotoxicity generally observed for dinuclear platinum complexes linked by polyamines. The upfield shifts of the resonances from the methylene protons in the linking triamine ligand observed in the 1H NMR spectra of either CT033 and CT233 upon addition of either Q[7] or Q[8] indicate that the cucurbituril is positioned over the linking ligand. However, the results show that the protonated secondary amine in CT033 acts as a barrier to encapsulation, with the Q[7,8] being positioned over only one propyl-arm at a time. Alternatively, the entire triamine linking ligand of CT233 is fully encapsulated within the Q[7,8] cavity. Encapsulation by Q[7,8] was found to reduce the rate of reaction of CT033 and CT233 with the thiol containing amino acid cysteine, with a greater rate reduction observed for CT233. These results are consistent with the NMR results of the Q[7,8] binding studies of the two platinum complexes. For CT033 encapsulated in Q[7,8], one of the two platinum centres is completely exposed to the solvent, whereas, for CT233 both platinum centres are simultaneously positioned within the portals of the cucurbit[n]uril, thereby, affording greater protection.

Polyamines. III. Spectroscopic properties of N,N-bis-(phthalimidopropyl)-N-octylamine and supramolecular interactions in its crystals

A new derivative of polyamine, N,N-bis-(phthalimidopropyl)-N-octylamine has been synthesized and its structure studied by X-ray diffraction, FTIR, 1H and 13C NMR spectroscopy. The B3LYP and DFT calculations have been carried out. The molecular conformation of N,N-bis-(phthalimidopropyl)-N-octylamine is folded and stabilized by an intramolecular C{single bond}H?O hydrogen bond. A close similarity to the conformation of N,N-bis-(phthalimidopropyl)-N-propylamine has been found. The both molecules differ by the length of the saturated chains on the N-amine atom. The long N-octyl chain substituent gives rise to the supramolecular structure which is different to that one formed by the N-propyl derivative. The supramolecular structure is driven by weak C{single bond}H?O and π?π interactions. The optimized bond lengths as well as bond angles for N,N-bis-(phthalimidopropyl)-N-octylamine calculated by B3LYP/6-31G(d,p) approach are compared with the X-ray data. The screening constants for 13C and 1H atoms have been calculated by the GIAO/B3LYP/6-31G(d,p) approach and analyzed. Linear correlations between the experimental 1H and 13C chemical shifts and the computed screening constants have been obtained.

Copper(ii) complexes as turn on fluorescent sensors for nitric oxide

Two copper(ii) complexes, 1 and 2, of two tridentate N-donor ligands, L1 and L2 [L1 = dansyl derivative of bis-[3-(dimethylamino)-propyl]amine; L2 = dansyl derivative of dipropylenetriamine] were synthesized and characterized. The quenched fluorescence intensity of complexes 1 and 2, in degassed methanol or aqueous (buffered at pH 7.2) solution, was found to reappear on exposure to nitric oxide. This is attributed to the reduction of paramagnetic Cu(ii) center by nitric oxide to diamagnetic Cu(i).

Synthesis of a symmetrically branched template for parallel α-helix dimers

The synthesis of a symmetrical diamino acid is described for the assembly of parallel α-helices in solid phase peptide synthesis. This handle is designed to replace the C-terminal half of a class of DNA binding proteins, the Leucine Zipper.

Syntheses of tertiary tetraamines and quaternary pentaamines with three and four methylene chain units

Tertiary tetraamines and quaternary pentaamines composed of aminopropyl and/or aminobutyl groups were synthesized as authentic samples for the identification of naturally occurring branched polyamines. Four tertiary tetraamines were obtained by alkylating the free secondary amine group of diphthaloyl derivatives of sym-norspermidine or sym-homospermidine with N-(3-bromopropyl)phthalimide or N-(4-bromobutyl)phthalimide in the presence of KF-Celite. Five quaternary pentaamines were obtained by fusing triphthaloyl derivatives of the tertiary tetraamines with an excess amount of N-(3-iodopropyl)phthalimide or N-(4-iodobutyl)phthalimide. The present methods are simple and achieved high yields. The 13C-NMR spectra of these branched polyamines were recorded in D2O as fully protonated forms, and all 13C chemical shifts were assigned consistently.

Unusual specificity of a receptor for Nd3+ among other lanthanide ions for selective colorimetric recognition

A rare example of a reversible recognition of Nd3+ by a newly synthesized molecular receptor (L1), having a diazo group as the reporter functionality, is reported. Studies revealed that this receptor eventually forms a [Nd3+]2L1 type complex, through the formation of the intermediate complex [Nd3+]L 1 following a two-step equilibrium process. Respective equilibrium constants for two successive processes were evaluated based on data obtained from the systematic fluorescence titration. Formation of [Nd3+] 2L1 caused a detectable change in color, and associated affinity constants were also evaluated from spectrophotometric titration data. A rather unusual binding mode of L1 for Nd3+ ion is established by various spectroscopic studies. The remarkable specificity of L1 for Nd3+, constitutes a rare example of a highly selective receptor for this ion in the presence of excess of all other lanthanide ions.

The influence of amine functionalities on anion binding in polyamide-containing macrocycles

Image Presented Mixed amide/amine macrocyclic anion hosts of varying sizes and with different amine substituents have been synthesized and characterized. Host 2, containing a 28-membered ring and secondary amines, has shown selective binding for HSO4- over other oxo anions and halides in DMSO-d 6 using NMR titrations. Crystal structures of SO4 2-, HPO42-, H2PO4-, and H2P2O72- with the 28-membered ring hosts indicate different macrocyclic conformations depending on the N-substituent. Anion affinities appear to be correlated with macrocycle conformation.

Polyamines. I. Spectroscopic properties of N,N-bis-(phthalimidopropyl)-N-propylamine and supramolecular interactions in its crystals

A new derivative of polyamine, N,N-bis-(phthalimidopropyl)-N-propylamine (1) has been synthesized and its structure studied by X-ray diffraction, FTIR, Raman, 1H and 13C NMR spectroscopies. The B3LYP and DFT calculations have been carried out. The molecular structure of N,N-bis-(phthalimidopropyl)-N-propylamine (1) presents the first case of a folded conformation for this group of compounds which is stabilized by an intramolecular hydrogen bond C-H?O. Neither C-H?π, π?π or C{double bond, short}O?C{double bond, short}O interactions operate in this case. Also the supramolecular structure is stabilized by weak C-H?O and C-H?π hydrogen bonds. The optimized bond lengths as well as bond angles for 1 calculated by B3LYP/6-31G(d,p) approach are compared with the X-ray data. The screening constants for 13C and 1H atoms have been calculated by the GIAO/B3LYP/6-31G(d,p) approach and analyzed. Linear correlations between the experimental 1H and 13C chemical shifts and the computed screening constants have been obtained.

Synthesis and antimicrobial activity of the symmetric dimeric form of temporin A based on 3-N,N-di(3-aminopropyl)amino propanoic acid as the branching unit

Dimeric derivative of antimicrobial peptide amide Temporin A (TA) was synthesized by using a new branching unit 3-N,N-di(3-aminopropyl) amino propanoic acid (DAPPA), which allows building of the parallelly symmetric α-helical structures. Antimicrobial effect of the original peptide amide, its monomeric carboxy (TAc) and novel dimeric (TAd) analogues were tested against Staphylococcus aureus (Gram-positive) and Escherichia coli (Gram-negative). Both TA and TAd completely inhibited the growth of S. aureus at the concentrations of 5 and 10μM, respectively, whereas TAc did not show any inhibitory activity. The activities of TAc TA and TAd correlate directly with the net charges of the molecules, +1, +2 and +4, respectively. Interestingly, TAd displayed antibacterial effect against E. coli at a concentration of 10μM, whereas as monomeric TA did not show any activity at concentration as high as 20μM. The results indicate that the novel structural modification improves the antibacterial properties of Temporin A especially towards Gram-negative bacteria. Copyright