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| CAS No.: | 157-03-9 |
|---|---|
| Name: | 6-DIAZO-5-OXO-L-NORLEUCINE |
| Article Data: | 6 |
| Molecular Structure: | |
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|
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| Formula: | C6H9 N3 O3 |
| Molecular Weight: | 171.156 |
| Synonyms: | Norleucine,6-diazo-5-oxo-, L- (8CI);6-Diazo-5-oxo-L-norleucine;DON;DON(pharmaceutical);L-6-Diazo-5-oxonorleucine;L-DON;NSC 7365; |
| Density: | g/cm3 |
| Melting Point: | -145oC (dec.) |
| Boiling Point: | °Cat760mmHg |
| Flash Point: | °C |
| Hazard Symbols: | T |
| Risk Codes: | 23/24/25 |
| Safety: | Poison by ingestion, intraperitoneal, and intravenous routes. Experimental teratogenic and reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. |
| PSA: | 117.78000 |
| LogP: | -0.17044 |
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| Conditions | Yield |
|---|---|
| With sodium hydroxide In methanol for 0.5h; Ambient temperature; | 88% |
- 208520-02-9
ethyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-6-diazo-5-oxohexanoate
- 157-03-9
6-diazo-5-oxo-L-norleucine
| Conditions | Yield |
|---|---|
| With piperidine for 0.0333333h; | 81% |
- 157-03-9
6-diazo-5-oxo-L-norleucine
| Conditions | Yield |
|---|---|
| With piperidine for 0.0333333h; Inert atmosphere; | 52% |
- 884594-54-1
(S)-6-diazo-5-oxo-2-(2,2,2-trifluoro-acetylamino)-hexanoic acid ethyl ester
- 157-03-9
6-diazo-5-oxo-L-norleucine
| Conditions | Yield |
|---|---|
| With sodium hydroxide |
- 42294-25-7
(2S)-2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)pentanedioic acid α-methyl ester
- 157-03-9
6-diazo-5-oxo-L-norleucine
| Conditions | Yield |
|---|---|
| ueber mehrere Stufen; |
- 157-03-9
6-diazo-5-oxo-L-norleucine
| Conditions | Yield |
|---|---|
| With piperidine |
- 157-03-9
6-diazo-5-oxo-L-norleucine
| Conditions | Yield |
|---|---|
| With sodium hydroxide |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 5 steps 1: diethyl ether 2: TFA / CH2Cl2 3: N-methylmorpholine / 0 °C 4: diethyl ether 5: 4M NaOH View Scheme |
- 160002-61-9
N-(9-fluorenylmethoxycarbonyl)glutamic acid (O-tert-butyl) methyl ester
- 157-03-9
6-diazo-5-oxo-L-norleucine
| Conditions | Yield |
|---|---|
| Multi-step reaction with 4 steps 1: TFA / CH2Cl2 2: N-methylmorpholine / 0 °C 3: diethyl ether 4: 4M NaOH View Scheme |
- 145038-49-9
4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-methoxy-5-oxopentanoic acid
- 157-03-9
6-diazo-5-oxo-L-norleucine
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: N-methylmorpholine / 0 °C 2: diethyl ether 3: 4M NaOH View Scheme |
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Chemistry
Molecule structure of 6-Diazo-5-oxonorleucine (CAS NO.157-03-9) :
IUPAC Name: 5-amino-1-diazonio-6-hydroxy-6-oxohex-1-en-2-olate
Molecular Weight: 171.15396 g/mol
Molecular Formula: C6H9N3O3
Melting Point: ~145 °C (dec.)
Appreance: light yellow crystalline
Merck: 13.3026
XLogP3-AA: -1.5
H-Bond Donor: 2
H-Bond Acceptor: 5
Rotatable Bond Count: 4
Exact Mass: 171.064391
MonoIsotopic Mass: 171.064391
Topological Polar Surface Area: 115
Heavy Atom Count: 12
Complexity: 240
Canonical SMILES: C(CC(=C[N+]#N)[O-])C(C(=O)O)N
InChI: InChI=1S/C6H9N3O3/c7-5(6(11)12)2-1-4(10)3-9-8/h3,5H,1-2,7H2,(H-,10,11,12)
InChIKey: MKZFABOMIIHLIT-UHFFFAOYSA-N
Storage temp.: −20 °C
Uses
6-Diazo-5-oxonorleucine (CAS NO.157-03-9) exerts a growth inhibitory effect selectively on the neuroendocrine tumour cell line BON and is proposed as an antitumour drug.
Toxicity Data With Reference
| 1. | pic-esc 5 µg/plate | CNREA8 Cancer Research. 43 (1983),2819. | ||
| 2. | ipr-rat LD50:80 mg/kg | CPCHAO Clinical Proceedings of the Childrens Hospital of the District of Columbia. 18 (1962),307. | ||
| 3. | orl-mus LD50:197 mg/kg | NCISP* National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program, Bethesda, MD 20205 JAN86 . | ||
| 4. | ipr-mus LDLo:300 mg/kg | JOENAK Journal of Endocrinology. 18 (1959),204. | ||
| 5. | ivn-mus LD50:74 mg/kg | 85ERAY Antibiotics: Origin, Nature, and Properties. 2 (1978),1253. |
Consensus Reports
EPA Genetic Toxicology Program.
Safety Profile
Poison by ingestion, intraperitoneal, and intravenous routes. Experimental teratogenic and reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes: 
T
Risk Statements: 23/24/25
R23/24/25: Toxic by inhalation, in contact with skin and if swallowed
Safety Statements: 36/37/39-45
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
RTECS: RC6340000
F: 8
Specification
6-Diazo-5-oxonorleucine (CAS NO.157-03-9) is also called 6-Diazo-5-oxo,l-norleucin ; 6-Diazo-5-oxo-l-norleucin ; Diazo-oxo-norleucine ; Don(pharmaceutical) ; 6-Diazo-5-oxo-l-2-aminohexanoic acid ; 6-Diazo-5-oxo-l-norleucine ; 6-diazo-5-oxo-norleucine ; L-don .