Diaziquone
-
Diaziquone
structure -
-
CAS No:
57998-68-2
-
Formula:
C16H20N4O6
-
Chemical Name:
Diaziquone
-
Synonyms:
Carbamic acid,N,N′-[2,5-bis(1-aziridinyl)-3,6-dioxo-1,4-cyclohexadiene-1,4-diyl]bis-,C,C′-diethyl ester;Carbamic acid,[2,5-bis(1-aziridinyl)-3,6-dioxo-1,4-cyclohexadiene-1,4-diyl]bis-,diethyl ester;1,4-Cyclohexadiene-1,4-dicarbamic acid,2,5-bis(1-aziridinyl)-3,6-dioxo-,diethyl ester;2,5-Diaziridinyl-3,6-bis(carboethoxyamino)-1,4-benzoquinone;NSC 182986;AZQ;3,6-Diaziridinyl-2,5-bis(carboethoxyamino)-1,4-benzoquinone;Diaziquone;Aziridinylbenzoquinone;CI 904
-
CAS No:
Description
ChEBI: A 1,4-benzoquinone that is substituted at positions 2 and 5 have been replaced by aziridin-1-yl groups and at positions 3 and 6 by (ethoxycarbonyl)amino groups.
Diaziquone is a 1,4-benzoquinone that is substituted at positions 2 and 5 have been replaced by aziridin-1-yl groups and at positions 3 and 6 by (ethoxycarbonyl)amino groups. It has a role as an antineoplastic agent and an alkylating agent. It is a carbamate ester, a member of aziridines, an enamine and a member of 1,4-benzoquinones.|Diaziquone is a water-soluble, synthetic aziridinylbenzoquinone with potential antineoplastic activity. Bioactivation of aziridinylbenzoquinone RH1 occurs through the two-electron reduction of the quinone to the hydroquinone by the two-electron quinone reductase DT-diaphorase (DTD). The resultant hydroquinone selectively alkylates and cross-links DNA at the 5'-GNC-3' sequence, inihibiting DNA replication, inducing apoptosis, and inhibiting tumor cell proliferation. DTD is over-expressed in many tumors relative to normal tissue, including lung, colon, breast and liver tumors.
Characteristics
117
0.34240
1.45g/cm3
230 °C (decomp)
495.56°C (rough estimate)
237.4ºC
1.62
Dimethylsulfoxide 25 - 30 (mg/mL)
Peritoneal-mouse LD50: 11.290 mg/kg; intravenous-mouse LD50: 10.3 mg/kg
Flammable; burning produces toxic nitrogen oxide fumes
Safety Information
40
22-36
EY8794000
Xn
Ventilated, low temperature and dry; stored separately from food materials in warehouse
Bulk: A sample stored at 60 °C in the dark for 30 days showed < 2% decomposition (HPLC). Solution: A sample in 5% DMA (1mg/mL) showed 18% decomposition after 8 hours at room temperature. (HPLC)
Drug Information
Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)|Reagents with two reactive groups, usually at opposite ends of the molecule, that are capable of reacting with and thereby forming bridges between side chains of amino acids in proteins; the locations of naturally reactive areas within proteins can thereby be identified; may also be used for other macromolecules, like glycoproteins, nucleic acids, or other. (See all compounds classified as Cross-Linking Reagents.)
1,4-cyclohexadiene-1,4-dicarbamic acid, 2,5-(bis-(1-aziridinyl))-3,6-dioxo diethyl ester
Computed Properties
Molecular Weight:364.35
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:8
Exact Mass:364.13828437
Monoisotopic Mass:364.13828437
Topological Polar Surface Area:117
Heavy Atom Count:26
Complexity:671
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes