22291-04-9,MFCD27923061
Catalog No.:AA00BHK2

22291-04-9 | 2,7-Bis(2-(dimethylamino)ethyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2h,7h)-tetraone

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95+%
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
Technical Information
Catalog Number:
AA00BHK2
Chemical Name:
2,7-Bis(2-(dimethylamino)ethyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2h,7h)-tetraone
CAS Number:
22291-04-9
Molecular Formula:
C22H24N4O4
Molecular Weight:
408.4504
MDL Number:
MFCD27923061
SMILES:
CN(CCn1c(=O)c2ccc3c4c2c(c1=O)ccc4c(=O)n(c3=O)CCN(C)C)C
Properties
Computed Properties
 
Complexity:
641  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0  
Defined Bond Stereocenter Count:
0  
Formal Charge:
0  
Heavy Atom Count:
30  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
0  
Isotope Atom Count:
0  
Rotatable Bond Count:
6  
Undefined Atom Stereocenter Count:
0  
Undefined Bond Stereocenter Count:
0  
XLogP3:
1.2  

Downstream Synthesis Route

[1]BioorganicandMedicinalChemistry,2001,vol.9,p.2015-2024

[2]ChemicalCommunications,2011,vol.47,p.5581-5583

[3]SpectrochimicaActaPartA:MolecularandBiomolecularSpectroscopy,2006,vol.64,p.435-441

[4]BioorganicandMedicinalChemistry,2007,vol.15,p.555-562

[5]BioorganicandMedicinalChemistryLetters,2008,vol.18,p.1668-1673

[6]Patent:WO2009/68916,2009,A1.Locationinpatent:Page/Pagecolumn29

[7]Chemistry-AEuropeanJournal,2014,vol.20,p.7309-7316

[8]JournalofMedicinalChemistry,1985,vol.28,p.1216-1222

[9]SpectrochimicaActaPartA:MolecularandBiomolecularSpectroscopy,2008,vol.70,p.907-915

[10]AngewandteChemie-InternationalEdition,2018,vol.57,p.17115-17119    Angew.Chem.,2018,vol.130,p.17361-17365,5

1-(4-Iodobutyl)thymine 
  22291-04-9   
C40H50N8O8(2+)*2I(1-) 

[1]ChemicalCommunications,1996,p.379-380

1-(4-Iodobutyl)thymine 
  22291-04-9   
C40H50N8O8(2+)*2F6P(1-) 

[1]ChemicalCommunications,1996,p.379-380

81-30-1    108-00-9    383413-13-6    22291-04-9   
N-(O-dimethoxytrityl-2-dimethyl-3-hydroxypropyl)-N'-2-(N,N-dimethylamino)-ethyl-1,4,5,8-naphtalenetetracarboxylicdiimide 
 
2,7-bis-{3-bis-(4-methoxy-phenyl)-phenyl-methoxy-2,2-dimethyl-propyl}-benzo<i>lmn</i>3,8phenanthroline-1,3,6,8-tetraone 

[1]BioorganicandMedicinalChemistry,2001,vol.9,p.2329-2334

Literature

Title: Improving the affinity of naphthalene diimide ligand to telomeric DNA by incorporating Zn²⁺ ions into its dipicolylamine groups.

Journal: Bioorganic & medicinal chemistry 20121101

Title: Stable solution-processed molecular n-channel organic field-effect transistors.

Journal: Advanced materials (Deerfield Beach, Fla.) 20120822

Title: Hydrogen-bonding-mediated vesicular assembly of functionalized naphthalene-diimide-based bolaamphiphile and guest-induced gelation in water.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20120806

Title: Self-assembly of supra-amphiphiles based on dual charge-transfer interactions: from nanosheets to nanofibers.

Journal: Langmuir : the ACS journal of surfaces and colloids 20120724

Title: Subtle recognition of 14-base pair DNA sequences via threading polyintercalation.

Journal: Biochemistry 20120605

Title: Reactions of brominated naphthalene diimide with bis(tributylstannyl)acetylene: a simple approach for conjugated polymers and versatile coupling intermediates.

Journal: Organic letters 20120601

Title: Aromatically functionalized cyclic tricholate macrocycles: aggregation, transmembrane pore formation, flexibility, and cooperativity.

Journal: The Journal of organic chemistry 20120518

Title: Room-temperature long-lived triplet excited states of naphthalenediimides and their applications as organic triplet photosensitizers for photooxidation and triplet-triplet annihilation upconversions.

Journal: The Journal of organic chemistry 20120420

Title: Photoinduced electron transfer in zinc naphthalocyanine-naphthalenediimide supramolecular dyads.

Journal: Chemphyschem : a European journal of chemical physics and physical chemistry 20120410

Title: Design, synthesis and biological evaluation of new naphtalene diimides bearing isothiocyanate functionality.

Journal: European journal of medicinal chemistry 20120201

Title: DNA-templated assembly of naphthalenediimide arrays.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20120102

Title: Supramolecular naphthalenediimide nanotubes.

Journal: Topics in current chemistry 20120101

Title: Elongation of lifetime of the charge-separated state of ferrocene-naphthalenediimide-[60]fullerene triad via stepwise electron transfer.

Journal: The journal of physical chemistry. A 20111222

Title: Complexes of aryl-substituted porphyrins and naphthalenediimide (NDI): investigations by synchrotron X-ray diffraction and NMR spectroscopy.

Journal: Dalton transactions (Cambridge, England : 2003) 20111107

Title: Electrochemical DNA analysis with a supramolecular assembly of naphthalene diimide, ferrocene, and β-cyclodextrin.

Journal: Analytical chemistry 20111001

Title: Supramolecular construction of vesicles based on core-substituted naphthalene diimide appended with triethyleneglycol motifs.

Journal: Chemical communications (Cambridge, England) 20110807

Title: Naphthalene diimide scaffolds with dual reversible and covalent interaction properties towards G-quadruplex.

Journal: Biochimie 20110801

Title: Negative polaron and triplet exciton diffusion in organometallic 'molecular wires'.

Journal: Journal of the American Chemical Society 20110727

Title: A bio-inspired design strategy: Organization of tryptophan-appended naphthalenediimide into well-defined architectures induced by molecular interactions.

Journal: Nanoscale 20110601

Title: Electropolymerization of intercalator-grafted conducting polymer for direct and amplified DNA detection.

Journal: Chemical communications (Cambridge, England) 20110207

Title: Discrimination of phosphorylated double stranded DNA by naphthalene diimide having zinc(II) dipicolylamine complexes.

Journal: Bioorganic & medicinal chemistry 20110201

Title: An unusual addition reaction for constructing a novel pH-controlled fluorescence switch.

Journal: Organic letters 20110121

Title: Variation of the ultrafast fluorescence quenching in 2,6-sulfanyl-core-substituted naphthalenediimides by electron transfer.

Journal: The journal of physical chemistry. A 20101209

Title: Tetrasubstituted naphthalene diimide ligands with selectivity for telomeric G-quadruplexes and cancer cells.

Journal: Bioorganic & medicinal chemistry letters 20101115

Title: Evidence of preferential pi-stacking: a study of intermolecular and intramolecular charge transfer complexes.

Journal: Chemical communications (Cambridge, England) 20100814

Title: Near-IR core-substituted naphthalenediimide fluorescent chemosensors for zinc ions: ligand effects on PET and ICT channels.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20100726

Title: Experimental evidence for the functional relevance of anion-pi interactions.

Journal: Nature chemistry 20100701

Title: A pi-conjugated hydrogel based on an Fmoc-dipeptide naphthalene diimide semiconductor.

Journal: Chemical communications (Cambridge, England) 20100628

Title: Kinetics of charge separation in poly(A)-poly(T) DNA hairpins.

Journal: The journal of physical chemistry. B 20100520

Title: Substituted heterocyclic naphthalene diimides with unexpected acidity. Synthesis, properties, and reactivity.

Journal: The Journal of organic chemistry 20091120

Title: Self-assembly of 1-D n-type nanostructures based on naphthalene diimide-appended dipeptides.

Journal: Journal of the American Chemical Society 20091118

Title: Synthesis and photophysics of core-substituted naphthalene diimides: fluorophores for single molecule applications.

Journal: Chemistry, an Asian journal 20091005

Title: Quinone methides tethered to naphthalene diimides as selective G-quadruplex alkylating agents.

Journal: Journal of the American Chemical Society 20090916

Title: Excited-state dynamics of hybrid multichromophoric systems: toward an excitation wavelength control of the charge separation pathways.

Journal: The journal of physical chemistry. A 20090723

Title: Targeting human gastrointestinal stromal tumor cells with a quadruplex-binding small molecule.

Journal: Journal of medicinal chemistry 20090625

Title: Immobilization of a naphthalene diimide-DNA complex on the gold through dithiolane moieties.

Journal: Nucleic acids symposium series (2004) 20090101

Title: Identification of oligo(p-phenylene vinylene)-naphthalene diimide heterocomplexes by scanning tunneling microscopy and spectroscopy at the liquid-solid interface.

Journal: Chemical communications (Cambridge, England) 20081121

Title: Ultrafast photoinduced charge separation in naphthalene diimide based multichromophoric systems in liquid solutions and in a lipid membrane.

Journal: The journal of physical chemistry. B 20080731

Title: Self-assembled zinc chlorin rod antennae powered by peripheral light-harvesting chromophores.

Journal: Journal of the American Chemical Society 20080507

Title: Screening of pi-basic naphthalene and anthracene amplifiers for pi-acidic synthetic pore sensors.

Journal: Journal of the American Chemical Society 20080402

Title: Novel naphthalene diimides as activatable precursors of bisalkylating agents, by reduction and base catalysis.

Journal: The Journal of organic chemistry 20071026

Title: Tri-, tetra- and heptacyclic perylene analogues as new potential antineoplastic agents based on DNA telomerase inhibition.

Journal: Bioorganic & medicinal chemistry 20070101

Title: Metallomacrocycles that incorporate cofacially aligned diimide units.

Journal: Chemistry, an Asian journal 20061120

Title: Chemistry. From electron pump to proton channel.

Journal: Science (New York, N.Y.) 20060707

Title: Photoproduction of proton gradients with pi-stacked fluorophore scaffolds in lipid bilayers.

Journal: Science (New York, N.Y.) 20060707

Title: Direct detection of DNA with an electrocatalytic threading intercalator.

Journal: Analytical chemistry 20050101

Title: Photochemistry of naphthalene diimides: EPR study of free radical formation via photoredox process.

Journal: Photochemistry and photobiology 20050101

Title: Electrochemical gene detection by using adamantyl naphthalene diimide coupled with ferrocenyl-beta-cyclodextrin.

Journal: Nucleic acids symposium series (2004) 20040101

Title: Conjugates of PNA with naphthalene diimide derivatives having a broad range of DNA affinities.

Journal: Bioconjugate chemistry 20030101

Title: Bis-naphthalene diimide exhibiting an effective bis-threading intercalating ability.

Journal: Nucleic acids research. Supplement (2001) 20030101

Title: Novel synthesis and RNA-binding properties of aminoglycoside dimers conjugated via a naphthalene diimide-based intercalator.

Journal: Bioorganic & medicinal chemistry letters 20011119

Title: Tethered naphthalene diimide intercalators enhance DNA triplex stability.

Journal: Bioorganic & medicinal chemistry 20010901

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SDS
Tags:22291-04-9 Molecular Formula|22291-04-9 MDL|22291-04-9 SMILES|22291-04-9 2,7-Bis(2-(dimethylamino)ethyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2h,7h)-tetraone
Catalog No.: AA00BHK2
22291-04-9,MFCD27923061
22291-04-9 | 2,7-Bis(2-(dimethylamino)ethyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2h,7h)-tetraone
Pack Size: 250mg
Purity: 95+%
in stock
$35.00 $25.00
Pack Size: 1g
Purity: 95+%
in stock
$103.00 $72.00
Quantity
- +
Add to Card
Order Now
bulk Quotation Request
Technical Information
Catalog Number: AA00BHK2
Chemical Name: 2,7-Bis(2-(dimethylamino)ethyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2h,7h)-tetraone
CAS Number: 22291-04-9
Molecular Formula: C22H24N4O4
Molecular Weight: 408.4504
MDL Number: MFCD27923061
SMILES: CN(CCn1c(=O)c2ccc3c4c2c(c1=O)ccc4c(=O)n(c3=O)CCN(C)C)C
Properties
Complexity: 641  
Covalently-Bonded Unit Count: 1  
Defined Atom Stereocenter Count: 0  
Defined Bond Stereocenter Count: 0  
Formal Charge: 0  
Heavy Atom Count: 30  
Hydrogen Bond Acceptor Count: 6  
Hydrogen Bond Donor Count: 0  
Isotope Atom Count: 0  
Rotatable Bond Count: 6  
Undefined Atom Stereocenter Count: 0  
Undefined Bond Stereocenter Count: 0  
XLogP3: 1.2  
Downstream Synthesis Route
81-30-1    108-00-9    22291-04-9 

[1]BioorganicandMedicinalChemistry,2001,vol.9,p.2015-2024

[2]ChemicalCommunications,2011,vol.47,p.5581-5583

[3]SpectrochimicaActaPartA:MolecularandBiomolecularSpectroscopy,2006,vol.64,p.435-441

[4]BioorganicandMedicinalChemistry,2007,vol.15,p.555-562

[5]BioorganicandMedicinalChemistryLetters,2008,vol.18,p.1668-1673

[6]Patent:WO2009/68916,2009,A1.Locationinpatent:Page/Pagecolumn29

[7]Chemistry-AEuropeanJournal,2014,vol.20,p.7309-7316

[8]JournalofMedicinalChemistry,1985,vol.28,p.1216-1222

[9]SpectrochimicaActaPartA:MolecularandBiomolecularSpectroscopy,2008,vol.70,p.907-915

[10]AngewandteChemie-InternationalEdition,2018,vol.57,p.17115-17119    Angew.Chem.,2018,vol.130,p.17361-17365,5

1-(4-Iodobutyl)thymine 
  22291-04-9   
C40H50N8O8(2+)*2I(1-) 

[1]ChemicalCommunications,1996,p.379-380

1-(4-Iodobutyl)thymine 
  22291-04-9   
C40H50N8O8(2+)*2F6P(1-) 

[1]ChemicalCommunications,1996,p.379-380

81-30-1    108-00-9    383413-13-6    22291-04-9   
N-(O-dimethoxytrityl-2-dimethyl-3-hydroxypropyl)-N'-2-(N,N-dimethylamino)-ethyl-1,4,5,8-naphtalenetetracarboxylicdiimide 
 
2,7-bis-{3-bis-(4-methoxy-phenyl)-phenyl-methoxy-2,2-dimethyl-propyl}-benzo<i>lmn</i>3,8phenanthroline-1,3,6,8-tetraone 

[1]BioorganicandMedicinalChemistry,2001,vol.9,p.2329-2334

Literature fold

Title: Improving the affinity of naphthalene diimide ligand to telomeric DNA by incorporating Zn²⁺ ions into its dipicolylamine groups.

Journal: Bioorganic & medicinal chemistry20121101

Title: Stable solution-processed molecular n-channel organic field-effect transistors.

Journal: Advanced materials (Deerfield Beach, Fla.)20120822

Title: Hydrogen-bonding-mediated vesicular assembly of functionalized naphthalene-diimide-based bolaamphiphile and guest-induced gelation in water.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany)20120806

Title: Self-assembly of supra-amphiphiles based on dual charge-transfer interactions: from nanosheets to nanofibers.

Journal: Langmuir : the ACS journal of surfaces and colloids20120724

Title: Subtle recognition of 14-base pair DNA sequences via threading polyintercalation.

Journal: Biochemistry20120605

Title: Reactions of brominated naphthalene diimide with bis(tributylstannyl)acetylene: a simple approach for conjugated polymers and versatile coupling intermediates.

Journal: Organic letters20120601

Title: Aromatically functionalized cyclic tricholate macrocycles: aggregation, transmembrane pore formation, flexibility, and cooperativity.

Journal: The Journal of organic chemistry20120518

Title: Room-temperature long-lived triplet excited states of naphthalenediimides and their applications as organic triplet photosensitizers for photooxidation and triplet-triplet annihilation upconversions.

Journal: The Journal of organic chemistry20120420

Title: Photoinduced electron transfer in zinc naphthalocyanine-naphthalenediimide supramolecular dyads.

Journal: Chemphyschem : a European journal of chemical physics and physical chemistry20120410

Title: Design, synthesis and biological evaluation of new naphtalene diimides bearing isothiocyanate functionality.

Journal: European journal of medicinal chemistry20120201

Title: DNA-templated assembly of naphthalenediimide arrays.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany)20120102

Title: Supramolecular naphthalenediimide nanotubes.

Journal: Topics in current chemistry20120101

Title: Elongation of lifetime of the charge-separated state of ferrocene-naphthalenediimide-[60]fullerene triad via stepwise electron transfer.

Journal: The journal of physical chemistry. A20111222

Title: Complexes of aryl-substituted porphyrins and naphthalenediimide (NDI): investigations by synchrotron X-ray diffraction and NMR spectroscopy.

Journal: Dalton transactions (Cambridge, England : 2003)20111107

Title: Electrochemical DNA analysis with a supramolecular assembly of naphthalene diimide, ferrocene, and β-cyclodextrin.

Journal: Analytical chemistry20111001

Title: Supramolecular construction of vesicles based on core-substituted naphthalene diimide appended with triethyleneglycol motifs.

Journal: Chemical communications (Cambridge, England)20110807

Title: Naphthalene diimide scaffolds with dual reversible and covalent interaction properties towards G-quadruplex.

Journal: Biochimie20110801

Title: Negative polaron and triplet exciton diffusion in organometallic 'molecular wires'.

Journal: Journal of the American Chemical Society20110727

Title: A bio-inspired design strategy: Organization of tryptophan-appended naphthalenediimide into well-defined architectures induced by molecular interactions.

Journal: Nanoscale20110601

Title: Electropolymerization of intercalator-grafted conducting polymer for direct and amplified DNA detection.

Journal: Chemical communications (Cambridge, England)20110207

Title: Discrimination of phosphorylated double stranded DNA by naphthalene diimide having zinc(II) dipicolylamine complexes.

Journal: Bioorganic & medicinal chemistry20110201

Title: An unusual addition reaction for constructing a novel pH-controlled fluorescence switch.

Journal: Organic letters20110121

Title: Variation of the ultrafast fluorescence quenching in 2,6-sulfanyl-core-substituted naphthalenediimides by electron transfer.

Journal: The journal of physical chemistry. A20101209

Title: Tetrasubstituted naphthalene diimide ligands with selectivity for telomeric G-quadruplexes and cancer cells.

Journal: Bioorganic & medicinal chemistry letters20101115

Title: Evidence of preferential pi-stacking: a study of intermolecular and intramolecular charge transfer complexes.

Journal: Chemical communications (Cambridge, England)20100814

Title: Near-IR core-substituted naphthalenediimide fluorescent chemosensors for zinc ions: ligand effects on PET and ICT channels.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany)20100726

Title: Experimental evidence for the functional relevance of anion-pi interactions.

Journal: Nature chemistry20100701

Title: A pi-conjugated hydrogel based on an Fmoc-dipeptide naphthalene diimide semiconductor.

Journal: Chemical communications (Cambridge, England)20100628

Title: Kinetics of charge separation in poly(A)-poly(T) DNA hairpins.

Journal: The journal of physical chemistry. B20100520

Title: Substituted heterocyclic naphthalene diimides with unexpected acidity. Synthesis, properties, and reactivity.

Journal: The Journal of organic chemistry20091120

Title: Self-assembly of 1-D n-type nanostructures based on naphthalene diimide-appended dipeptides.

Journal: Journal of the American Chemical Society20091118

Title: Synthesis and photophysics of core-substituted naphthalene diimides: fluorophores for single molecule applications.

Journal: Chemistry, an Asian journal20091005

Title: Quinone methides tethered to naphthalene diimides as selective G-quadruplex alkylating agents.

Journal: Journal of the American Chemical Society20090916

Title: Excited-state dynamics of hybrid multichromophoric systems: toward an excitation wavelength control of the charge separation pathways.

Journal: The journal of physical chemistry. A20090723

Title: Targeting human gastrointestinal stromal tumor cells with a quadruplex-binding small molecule.

Journal: Journal of medicinal chemistry20090625

Title: Immobilization of a naphthalene diimide-DNA complex on the gold through dithiolane moieties.

Journal: Nucleic acids symposium series (2004)20090101

Title: Identification of oligo(p-phenylene vinylene)-naphthalene diimide heterocomplexes by scanning tunneling microscopy and spectroscopy at the liquid-solid interface.

Journal: Chemical communications (Cambridge, England)20081121

Title: Ultrafast photoinduced charge separation in naphthalene diimide based multichromophoric systems in liquid solutions and in a lipid membrane.

Journal: The journal of physical chemistry. B20080731

Title: Self-assembled zinc chlorin rod antennae powered by peripheral light-harvesting chromophores.

Journal: Journal of the American Chemical Society20080507

Title: Screening of pi-basic naphthalene and anthracene amplifiers for pi-acidic synthetic pore sensors.

Journal: Journal of the American Chemical Society20080402

Title: Novel naphthalene diimides as activatable precursors of bisalkylating agents, by reduction and base catalysis.

Journal: The Journal of organic chemistry20071026

Title: Tri-, tetra- and heptacyclic perylene analogues as new potential antineoplastic agents based on DNA telomerase inhibition.

Journal: Bioorganic & medicinal chemistry20070101

Title: Metallomacrocycles that incorporate cofacially aligned diimide units.

Journal: Chemistry, an Asian journal20061120

Title: Chemistry. From electron pump to proton channel.

Journal: Science (New York, N.Y.)20060707

Title: Photoproduction of proton gradients with pi-stacked fluorophore scaffolds in lipid bilayers.

Journal: Science (New York, N.Y.)20060707

Title: Direct detection of DNA with an electrocatalytic threading intercalator.

Journal: Analytical chemistry20050101

Title: Photochemistry of naphthalene diimides: EPR study of free radical formation via photoredox process.

Journal: Photochemistry and photobiology20050101

Title: Electrochemical gene detection by using adamantyl naphthalene diimide coupled with ferrocenyl-beta-cyclodextrin.

Journal: Nucleic acids symposium series (2004)20040101

Title: Conjugates of PNA with naphthalene diimide derivatives having a broad range of DNA affinities.

Journal: Bioconjugate chemistry20030101

Title: Bis-naphthalene diimide exhibiting an effective bis-threading intercalating ability.

Journal: Nucleic acids research. Supplement (2001)20030101

Title: Novel synthesis and RNA-binding properties of aminoglycoside dimers conjugated via a naphthalene diimide-based intercalator.

Journal: Bioorganic & medicinal chemistry letters20011119

Title: Tethered naphthalene diimide intercalators enhance DNA triplex stability.

Journal: Bioorganic & medicinal chemistry20010901

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