63563-83-7

Basic information

• Product Name: bis(phthalimidylethyl)amine
• Synonyms: bis(phthalimidylethyl)amine
• CAS NO: 63563-83-7
• Molecular Weight: 363.373
• Mol File: 63563-83-7.mol

Chemical Properties

• CAS DataBase Reference: bis(phthalimidylethyl)amine(CAS DataBase Reference)
• NIST Chemistry Reference: bis(phthalimidylethyl)amine(63563-83-7)
• EPA Substance Registry System: bis(phthalimidylethyl)amine(63563-83-7)

Safety Data

• Hazardous Substances Data: 63563-83-7(Hazardous Substances Data)

Upstream product

• 85-44-9 phthalic anhydride 
• 111-40-0 3-azapentane-1,5-diamine 
• 1074-82-4 potassium phtalimide 
• 334-22-5 N,N-bis(chloro-2-ethyl)amine 

Downstream Products

• 23538-91-2 N,N-bis(2-(1,3-dioxoisoindolin-2-yl)ethyl)-4-methylbenzenesulfonamide 
• 1040797-37-2 C₂₈H₂₃N₃O₆ 
• 1320346-07-3 2-[bis(2-phthalimidoethyl)aminomethyl]phenyl bromide 
• 23538-89-8 2-[bis(2-phthalimidoethyl)aminomethyl]phenyl chloride 
• 190122-16-8 [1,2-bis(diphenylphosphino-k.P,P')ethane](N,N'-iminodiethylenebis(phthalimide)dithiocarbamato)nickel(II) tetraphenylborate monohydrate 
• 190122-13-5 bis(triphenylphosphine-k.P,P')(N,N'-iminodiethylenebis(phthalimide)dithiocarbamato)nickel(II) perchlorate * methanol * H₂O 
• 1314403-21-8 2,2′-(((2-hydroxybenzyl)azanediyl)bis(ethane-2,1-diyl))bis-(isoindoline-1,3-dione) 
• 1237536-38-7 4'-[p-{1,5-bis(phthalimido)-3-azapentan-3-ylmethyl}phenyl]-2,2':6',2'-terpyridine 
• 1445-69-8 2,3-dihydrophthalazine-1,4-dione 
• 3084-40-0 diethyl (1-hydroxymethyl)phosphonate 

Relevant articles and documents

Tricyclic host for linear anions

A tricyclic host for anions consisting of two tetraamide monocycles attached by two ethylene chains was designed and synthesized. Structural and binding results indicate that the receptor is selective for linear triatomic anions. Crystallographic data for two hydrated free bases, along with FHF -, N3-, and SO42- complexes indicate that there are at least two preferred gross conformations for the host, one of which possesses pseudo-D2 symmetry and the other pseudo-C2h symmetry. Both FHF- and N3 - are encapsulated in the pseudo-D2 symmetric complex, bridging the two tetraamido macrocyclic halves. The pseudo-C2h octahydrate structure shows an ice-like H-bonded (H2O)6 array of water molecules embedded in the host cavity. The SO4 2- structure has a nearly superimposable host conformation to the octahydrate but with the SO42- anions lying outside the host. Binding studies in DMSO-d6 indicate selectivity for FHF -, with lesser affinity for other inorganic anions.

Toward a Rational Design of Polyamine-Based Zinc-Chelating Agents for Cancer Therapies

In vitro viability assays against a representative panel of human cancer cell lines revealed that polyamines L1a and L5a displayed remarkable activity with IC50 values in the micromolar range. Preliminary research indicated that both compounds promoted G1 cell cycle arrest followed by cellular senescence and apoptosis. The induction of apoptotic cell death involved loss of mitochondrial outer membrane permeability and activation of caspases 3/7. Interestingly, L1a and L5a failed to activate cellular DNA damage response. The high intracellular zinc-chelating capacity of both compounds, deduced from the metal-specific Zinquin assay and ZnL2+ stability constant values in solution, strongly supports their cytotoxicity. These data along with quantum mechanical studies have enabled to establish a precise structure-Activity relationship. Moreover, L1a and L5a showed appropriate drug-likeness by in silico methods. Based on these promising results, L1a and L5a should be considered a new class of zinc-chelating anticancer agents that deserves further development.

Trapped bifluoride

(Figure Presented) The quest is over: A tricyclic amide-based anion receptor has been synthesized by connecting two monocyclic precursors. The receptor is highly selective for the binding of the elusive bifluoride anion HF2-, and the adduct represents the first structural example of an encapsulated bifluoride. The bifluoride lies midway between the two macrocycles making up the tricycle and is held by four hydrogen-bonding contacts with the macrocyclic amides.

Fluorescent ligand design for mononuclear copper(I) complex fluorescence in aqueous solution

The fluorescent ligands 3-(2-methylquinolyl)diethylenetriamine (QDETA) and bis(2-pyridylmethyl)(2-quinolylmethyl)amine (BPQA), and these Cu(II) complexes were synthesized. The fluorescence of [Cu(I/II)(qdeta)]+/2+ and [Cu(I/II)(bpqa)]+/2+ in aqueous solution was characterized; [Cu(I)(qdeta)]+ and [Cu(I)(bpqa)]+ were found to fluoresce in aqueous solution, whereas the fluorescence of [Cu(II)(qdeta)]2+ and [Cu(II)(bpqa)]2+ was almost completely quenched. The chelation enhanced fluorescence effect was observed for both [Cu(I)(qdeta)]+ and [Cu(I)(bpqa)]+. The pentacoordinated Cu(II) complex, [Cu(II)(qdeta)(H2O)]NDSA?2H2O (NDSA = 1,5-Naphthalenedisulfonate anion) was characterized by single crystal X-ray crystallography. The geometry around the copper center is a distorted square pyramid with four nitrogen atoms from the QDETA and an oxygen atom from the aqua.

Synthesis and coordination properties of an azamacrocyclic Zn(II) chemosensor containing pendent methylnaphthyl groups

The synthesis of a polyazamacrocycle constituted by two diethylenetriamine bridges functionalized at their central nitrogen with naphth-2-ylmethyl units and interconnected through 2,6-dimethylpyridine spacers (L1) is reported. The protonation behaviour of the new macrocycle in water and in water-ethanol 70/30 v/v mixed solvent has been examined by means of pH-metric, UV-Vis and steady-state fluorescence techniques. The fluorescence emission is slightly quenched following the deprotonation of the central tertiary amines and more deeply quenched upon deprotonation of the secondary amino groups. pH-Metric titrations show that in water-ethanol 70/30 v/v L1 forms stable mononuclear complexes with the divalent transition and post-transition metal ions Mn 2+, Fe2+, Co2+, Cu2+, Zn 2+, Cd2+, Hg2+ and Pb2+. In the case of Cu2+, Zn2+, Hg2+ and Pb2+, formation of binuclear complexes has also been observed. Steady-state fluorescence emission studies show that while interaction with Cu2+ leads to quenching of the fluorescence emission above pH = 2, interaction with Zn2+, Cd2+, Hg2+ and Pb2+ give rise to enhancements of the fluorescence above pH ca. 5, which is particularly noticeable in the case of Zn2+.

Design, synthesis of methotrexate-diosgenin conjugates and biological evaluation of their effect on methotrexate transport-resistant cells

A series of methotrexate-diosgenin conjugates was designed and synthesized to enhance the passive internalization of methotrexate (MTX) into transport-resistant cells. The inhibitory effects of these conjugates on dihydrofolate reductase (DHFR), and their anti-proliferation behaviors against a transport-resistant breast cancer cell line, MDA-MB-231, were investigated. All of the synthesized conjugates retained an ability to inhibit DHFR after the diosgenin substitution. The MTX conjugates were much more potent against methotrexate-resistant MDA-MB-231 cells than MTX. Conjugate 18, containing a disulfide bond, exhibited the most potent anti-proliferative and DHFR inhibitory effects (IC50?=?4.1?μM and 17.21?nM, respectively). Anti-proliferative activity was higher in the conjugate with a longer space linker (conjugate 21) than those with shorter linkers (conjugates 19 and 20). These results suggest that diosgenin conjugation of MTX may be an effective way to overcome its transport resistance in cancer cells.

Synthesis of two derivatives of 3,6,9-tri(carboxymethyl)-3,6,9-triazaundecanedioic acid and the stabilities of their complexes with Ca2+, Cu2+, Zn2+, Dy3+ and Gd3+

Two N-2-hydroxy-1-phenylethyl and N-2-hydroxy-2-phenylethyl derivatives of DTPA (3,6,9-tri(carboxymethyl)-3,6,9-triazaundecanedioic acid), DTPA-H1P = 3,9-di(carboxymethyl)-6-2-hydroxy-1-phenylethyl-3,6,9-triazaundecanedioic acid, and DTPA-H2P = 3,9-di(carboxymethyl)-6-2-hydroxy-2-phenylethyl-3,6,9-triazaundecanedioic acid were synthesized. Their protonation constants were determined by potentiometric titration in 0.10 M Me4NNO3 and by NMR pH titration at 25.0 ± 0.1 °C. The formations of lanthanide(III), copper(II), zinc(II) and calcium(II) complexes were investigated quantitatively by potentiometry. The stability constant for Gd(III) complex is larger than those for Ca(II), Zn(II) and Cu(II) complexes with these two ligands. The selectivity constants and modified selectivity constants of the DTPA-H1P and DTPA-H2P for Gd(III) over endogenously available metal ions were calculated. Comparing pM values at physiological pH 7.4 assesses effectiveness of these two ligands in binding divalent and trivalent metal ions in biological media. The observed water proton relaxivity values of [Gd(DTPA-H1P)] and [Gd(DTPA-H2P)]- became constant with respect to pH changes over the range of 4-10. 17O NMR shifts showed that the [Dy(DTPA-H1P)]- and [Dy(DTPA-H2P)]- complexes at pH 6.30 had 1.91 and 2.28 inner-sphere water molecules, respectively. Water proton spin-lattice relaxation rates of [Gd(DTPA-H1P)]- and [Gd(DTPA-H2P)]- complexes were also consistent with the inner-sphere Gd(III) coordination.

Palladium anchored on guanidine-terminated magnetic dendrimer (G3-Gu-Pd): An efficient nano-sized catalyst for phosphorous-free Mizoroki-Heck and copper-free Sonogashira couplings in water

In this research, a novel type of Fe3O4&at;silica-supported dendrimer capped by guanidine groups for immobilization of palladium was reported. This novel nano-sized catalyst was characterized by FTIR, TGA, XRD, FESEM, EDX, VSM, XPS and HRTEM methods. Enhanced catalytic activity of the prepared catalyst in Mizoroki-Heck and copper-free Sonogashira coupling reactions were evaluated in water as a green solvent. The influence of the various reaction parameters such as catalyst dosage, time and temperature on two mentioned C–C coupling reactions were studied. Results showed that the catalyst could be easily recovered by simple separation by an external magnet and reused for five cycles of recovery without considerable losing of its activity.

Phthalimide compound and preparation method thereof

The invention relates to a phthalimide compound and a preparation method thereof. The preparation method comprises the following steps that 1, dissolving bis (2-phthalimide) amine, allyl glycidyl ether and sodium hydroxide in cyclohexane to obtain a mixed system A; step 2, reacting the mixed system A at 70-80 DEG C to obtain a mixed system B; and 3, sequentially removing cyclohexane and impuritiesin the mixed system B. Under alkaline conditions, active primary amine at the center of bis (2-phthalimide) amine and allyl glycidyl ether are subjected to a ring-opening reaction; OH easily enables -NH to lose H under alkalinity and high temperature, -NH forms -N with stronger nucleophilicity to attack an epoxy group to open rings, proton H is combined with an O atom of an open-ring epoxy group,-N ions are combined with C atoms, and N-(3-allyloxy-2-hydroxypropyl)-bis (ethyl-2-phthalimide) is prepared.

Synthesis of Titanium Complexes Supported by Carbinolamide- And Amide-Containing Ligands Derived from Ti(NMe2)4-Mediated Selective Amidations of Carbonyl Groups

An efficient strategy for the syntheses of a series of titanium complexes has been developed. This protocol features the employment of Ti(NMe2)4 both as the metal center to trigger the deprotonation of the ligands and as an amine source to proceed the amidation reactions of carbonyl functionalities of the ligands. Treatment of Ti(NMe2)4 with a ligand HL1 (HL1 = 2,2′-(((2-hydroxybenzyl)azanediyl)bis(ethane-2,1-diyl))bis(isoindoline-1,3-dione) results in the formation of Ti(L1′)(NMe2) (1) (H3L1′ = N1-(2-((2-(1-(dimethylamino)-1-hydroxy-3-oxoisoindolin-2-yl)ethyl)(2-hydroxybenzyl)amino)ethyl)-N2,N2-dimethylphthalamide). One important feature regarding the synthesis of 1 is the occurrence of the in situ metal-ligand reaction between Ti(NMe2)4 and HL1, leading to the simultaneous formations of carbinolamide and amide scaffolds. Another prominent feature in terms of the preparation of 1 is the achievement of the selective ring-opening reaction of one of the two phthalimide units of the HL1 ligand, affording carbinolamide and amide functionalities within one ligand set. The developed methodology characterizes an ample substrate scope. The selective amidation reactions of the carbonyl groups have been realized for a series of analogous ligands HL2-HL7. Density functional theory calculations were employed to disclose the mechanisms for the formation of 1-7, and the details for the selective ring-opening reactions of the phthalimide unit were uncovered.