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205432-12-8,MFCD06407868
Catalog No.:AA002A0L

205432-12-8 | 1-Piperazinecarboxylic acid, 4-[2-(2,4-dinitrophenoxy)-1-oxidodiazenyl]-, ethyl ester

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1mg
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA002A0L
Chemical Name:
1-Piperazinecarboxylic acid, 4-[2-(2,4-dinitrophenoxy)-1-oxidodiazenyl]-, ethyl ester
CAS Number:
205432-12-8
Molecular Formula:
C13H16N6O8
Molecular Weight:
384.3015
MDL Number:
MFCD06407868
SMILES:
CCOC(=O)N1CCN(CC1)N(=NOc1ccc(cc1[N+](=O)[O-])[N+](=O)[O-])=O
NSC Number:
724771
Properties
Computed Properties
 
Complexity:
582  
Covalently-Bonded Unit Count:
1  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
27  
Hydrogen Bond Acceptor Count:
10  
Rotatable Bond Count:
5  
XLogP3:
2  

Literature

Title: Structural modifications modulate stability of glutathione-activated arylated diazeniumdiolate prodrugs.

Journal: Bioorganic & medicinal chemistry 20120501

Title: Activation of the c-Jun N-terminal kinase/activating transcription factor 3 (ATF3) pathway characterizes effective arylated diazeniumdiolate-based nitric oxide-releasing anticancer prodrugs.

Journal: Journal of medicinal chemistry 20111124

Title: Synthesis and evaluation of piperazine and homopiperazine analogues of JS-K, an anti-cancer lead compound.

Journal: Bioorganic & medicinal chemistry letters 20090515

Title: Synthesis, mechanistic studies, and anti-proliferative activity of glutathione/glutathione S-transferase-activated nitric oxide prodrugs.

Journal: Bioorganic & medicinal chemistry 20081115

Title: Synthesis and in vitro anti-leukemic activity of structural analogues of JS-K, an anti-cancer lead compound.

Journal: Bioorganic & medicinal chemistry letters 20080201

Title: JS-K, a GST-activated nitric oxide generator, induces DNA double-strand breaks, activates DNA damage response pathways, and induces apoptosis in vitro and in vivo in human multiple myeloma cells.

Journal: Blood 20070715

Title: JS-K, a nitric oxide prodrug, induces cytochrome c release and caspase activation in HL-60 myeloid leukemia cells.

Journal: Leukemia research 20061001

Title: Antitumor activity of JS-K [O2-(2,4-dinitrophenyl) 1-[(4-ethoxycarbonyl)piperazin-1-yl]diazen-1-ium-1,2-diolate] and related O2-aryl diazeniumdiolates in vitro and in vivo.

Journal: Journal of medicinal chemistry 20060713

Title: Nitric oxide prodrugs and metallochemotherapeutics: JS-K and CB-3-100 enhance arsenic and cisplatin cytolethality by increasing cellular accumulation.

Journal: Molecular cancer therapeutics 20040601

Title: JS-K, a novel non-ionic diazeniumdiolate derivative, inhibits Hep 3B hepatoma cell growth and induces c-Jun phosphorylation via multiple MAP kinase pathways.

Journal: Journal of cellular physiology 20031201

Title: JS-K, a glutathione/glutathione S-transferase-activated nitric oxide donor of the diazeniumdiolate class with potent antineoplastic activity.

Journal: Molecular cancer therapeutics 20030401

Title: Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells.

Journal: The Journal of biological chemistry 20020419

Title: The secondary amine/nitric oxide complex ion R(2)N[N(O)NO](-) as nucleophile and leaving group in S9N)Ar reactions.

Journal: The Journal of organic chemistry 20010504

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Tags:205432-12-8 Molecular Formula|205432-12-8 MDL|205432-12-8 SMILES|205432-12-8 1-Piperazinecarboxylic acid, 4-[2-(2,4-dinitrophenoxy)-1-oxidodiazenyl]-, ethyl ester