Conditions | Yield |
---|---|
With sodium carbonate In water at 24℃; for 0.25h; pH=7 - 7.5; | 100% |
succinic acid anhydride
deferoxamine mesylate
N-Succinyl-desferri-ferrioxyamin B
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide at 20℃; for 42h; Inert atmosphere; | 97% |
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 50℃; Solvent; Temperature; Inert atmosphere; | |
With pyridine at 20℃; Inert atmosphere; | 0.232 g |
2-benzyloxybenzoyl chloride
deferoxamine mesylate
N,O',O'',O'''-Tetra(2-benzyloxy-benzoyl)desferri-ferrioxamin B
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In diethyl ether; water for 1h; | 93% |
Conditions | Yield |
---|---|
With sodium hydroxide In methanol at 40℃; for 4h; Product distribution / selectivity; | 92% |
1-(N-succinimidyloxycarbonyl)adamantane
deferoxamine mesylate
DFOB-AdA
Conditions | Yield |
---|---|
Stage #1: deferoxamine mesylate With sodium hydroxide In methanol Stage #2: 1-(N-succinimidyloxycarbonyl)adamantane In methanol at 55℃; for 4h; Product distribution / selectivity; | 92% |
1 ,4-phenylenediisothiocyanate
deferoxamine mesylate
N-[5-({3-[5-(acetyl-hydroxy-amino)-pentylcarbamoyl]-propionyl}-hydroxy-amino)-pentyl]-N'-hydroxy-N'-{5-[3-(4-isothiocyanato-phenyl)-thioureido]-pentyl}-succinamide
Conditions | Yield |
---|---|
With triethylamine In chloroform; water; isopropyl alcohol | 85% |
di-tert-butyl dicarbonate
deferoxamine mesylate
1-(tert-Butoxycarbonyl)-7,18,29-trihydroxy-8,11,19,22,30-pentaoxo-1,7,12,18,23,29-hexaazahentriacontane
Conditions | Yield |
---|---|
With triethylamine In 1,4-dioxane; water at 40℃; for 16h; | 83% |
With sodium carbonate In 1,4-dioxane; water |
Conditions | Yield |
---|---|
Stage #1: deferoxamine mesylate With N-ethyl-N,N-diisopropylamine In ethanol at 50℃; for 1h; Stage #2: 3,4-diethoxy-3-cyclobuten-1,2-dione In ethanol at 50℃; for 0.5h; | 83% |
Stage #1: deferoxamine mesylate With N-ethyl-N,N-diisopropylamine In ethanol at 50℃; for 1h; Stage #2: 3,4-diethoxy-3-cyclobuten-1,2-dione In ethanol at 50℃; for 0.5h; | 83% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide for 4h; | 82% |
3,5-dimethyl-1-adamantanecarboxylic acid
deferoxamine mesylate
DFOB-AdAdMe
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere; | 80% |
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere; | 80% |
deferoxamine mesylate
Conditions | Yield |
---|---|
With potassium hydroxide In water addn. of desferal to fresh prepared Al(OH)3 gel in water (by hydrolysis of Al(NO3)3 with a pH 10 NH4+/NH3 buffer soln. or 0.5 m KOH soln.), stirring overnight; filtn. and solvent removal under vac., elem. anal., mixt. of 2 isomers; | 78% |
deferoxamine mesylate
2-tert-butoxycarbonylamino-3-(tritylsulfanyl)propionic acid 2,5-dioxopyrrolidin-1-yl ester
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide at 20℃; for 18h; | 77% |
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; | 74% |
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere; | 73% |
Conditions | Yield |
---|---|
Stage #1: 2-(1-imidazolyl)acetic acid hydrochloride; deferoxamine mesylate With benzotriazol-1-ol; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 45℃; for 1h; Inert atmosphere; Stage #2: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 8h; | 72% |
1-octyl-3-(carboxymethyl)-imidazolium bromide
deferoxamine mesylate
Conditions | Yield |
---|---|
Stage #1: 1-octyl-3-(carboxymethyl)-imidazolium bromide; deferoxamine mesylate With benzotriazol-1-ol; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 50℃; for 1h; Inert atmosphere; Stage #2: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; | 71% |
deferoxamine mesylate
ferrioxamine B perchlorate pentahydrate
Conditions | Yield |
---|---|
With perchloric acid; sodium hydrogencarbonate In water ligand was dissolved in H2O, Fe-salt was added with stirring for 30 min, solid NaHCO3 was added, stirred for 1 h, filtered, passed through anion-exchange column (HClO4), washed, solvent was removed under reduced pressure, dissolved in MeOH, filtered; poured with excess of EtOAc with stirring, collected by centrifugation,redissolved in MeOH, filtered, EtOAc was added, collected, supernatant was decanted, solvent was slowly removed under midl vac. in vac. desiccator at 90°C for 2 d; elem. anal; | 70% |
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere; | 70% |
deferoxamine mesylate
1-carboxymethyl-3-hydroxy-2-methylpyridin-4-one
DFOB-L1D
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere; | 70% |
Conditions | Yield |
---|---|
Stage #1: 6-dibenzocyclooctynamidehexanoic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: deferoxamine mesylate With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere; | 69% |
deferoxamine mesylate
trolox
Conditions | Yield |
---|---|
Stage #1: trolox With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 1h; Inert atmosphere; Stage #2: deferoxamine mesylate In N,N-dimethyl-formamide for 16h; Inert atmosphere; | 68.8% |
Conditions | Yield |
---|---|
Stage #1: deferoxamine mesylate With sodium hydroxide In methanol Stage #2: biotin N-Hydroxysuccinimide ester In methanol at 55℃; for 4h; | 68% |
With sodium hydroxide In methanol at 60℃; Inert atmosphere; | 55% |
1-carboxymethyl-3-methyl-3H-imidazolium bromide
deferoxamine mesylate
Conditions | Yield |
---|---|
Stage #1: 1-carboxymethyl-3-methyl-3H-imidazolium bromide; deferoxamine mesylate With benzotriazol-1-ol; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 50℃; for 1h; Inert atmosphere; Stage #2: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; | 68% |
Conditions | Yield |
---|---|
Stage #1: C29H45N3O13 With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide for 0.166667h; Stage #2: deferoxamine mesylate In dimethyl sulfoxide for 3h; | 68% |
1-butyl-3-(carboxymethyl)-imidazolium bromide
deferoxamine mesylate
Conditions | Yield |
---|---|
Stage #1: 1-butyl-3-(carboxymethyl)-imidazolium bromide; deferoxamine mesylate With benzotriazol-1-ol; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 50℃; for 1h; Inert atmosphere; Stage #2: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; | 66% |
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere; | 65% |
deferoxamine mesylate
Conditions | Yield |
---|---|
Stage #1: deferoxamine mesylate With potassium carbonate In methanol at 20℃; for 0.5h; Stage #2: With copper(ll) sulfate pentahydrate; 3-azidosulfonyl-3H-imidazole-1-ium hydrogen sulfate In methanol; water at 20℃; for 4.5h; | 65% |
deferoxamine mesylate
Conditions | Yield |
---|---|
Stage #1: 2-[({[(1S,2E,6S)-6-{[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}-6-methylcyclooct-2-en-1-yl]oxy}carbonyl)(methyl)amino]acetic acid With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide for 0.166667h; Stage #2: deferoxamine mesylate In dimethyl sulfoxide for 3h; | 64% |
deferoxamine mesylate
(R)-trolox
Conditions | Yield |
---|---|
Stage #1: (R)-trolox With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide for 1h; Inert atmosphere; Stage #2: deferoxamine mesylate In N,N-dimethyl-formamide for 16h; Inert atmosphere; | 62% |
Molecular Structure of Deferoxamine mesylate (CAS NO.138-14-7):
IUPAC Name: N-[5-[[4-[5-[Acetyl(hydroxy)amino]pentylamino]-4-oxobutanoyl]-hydroxyamino]pentyl]-N'-(5-aminopentyl)-N'-hydroxybutanediamide ; Methanesulfonic acid
Molecular Weight: 656.78968 [g/mol]
Molecular Formula: C26H52N6O11S
H-Bond Donor: 7
H-Bond Acceptor: 12
EINECS: 205-314-3
Storage temp.: −20 °C
Solubility: H2O: 50 mg/mL
Appearance: white to off-white powder
Flash Point: 538.5 °C
Enthalpy of Vaporization: 152.67 kJ/mol
Boiling Point: 966.9 °C at 760 mmHg
Vapour Pressure: 0 mmHg at 25 °C
Classification Code: Antidote [to iron poisoning]; Chelating agent; Drug / Therapeutic Agent; Human Data
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
man | TDLo | parenteral | 16gm/kg/34W-I (16000mg/kg) | CARDIAC: PERICARDITIS GASTROINTESTINAL: ULCERATION OR BLEEDING FROM SMALL INTESTINE BLOOD: OTHER CHANGES | American Journal of Kidney Diseases. Vol. 10, Pg. 71, 1987. |
man | TDLo | subcutaneous | 143mg/kg/4D-I (143mg/kg) | SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" GASTROINTESTINAL: NAUSEA OR VOMITING | British Medical Journal. Vol. 291, Pg. 448, 1985. |
mouse | LD50 | intraperitoneal | 1240mg/kg (1240mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Oyo Yakuri. Pharmacometrics. Vol. 7, Pg. 1181, 1973. |
mouse | LD50 | intravenous | 273mg/kg (273mg/kg) | Drugs in Japan Vol. 6, Pg. 496, 1982. | |
mouse | LD50 | oral | 15200mg/kg (15200mg/kg) | Drugs in Japan Vol. 6, Pg. 496, 1982. | |
mouse | LD50 | subcutaneous | 1280mg/kg (1280mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Oyo Yakuri. Pharmacometrics. Vol. 7, Pg. 1181, 1973. |
rat | LD50 | intravenous | 330mg/kg (330mg/kg) | Drugs in Japan Vol. 6, Pg. 496, 1982. | |
rat | LD50 | oral | 17300mg/kg (17300mg/kg) | Drugs in Japan Vol. 6, Pg. 496, 1982. | |
rat | LD50 | subcutaneous | 5500mg/kg (5500mg/kg) | Drugs in Japan Vol. 6, Pg. 496, 1982. | |
women | TDLo | subcutaneous | 150mg/kg/4D-I (150mg/kg) | GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" GASTROINTESTINAL: NAUSEA OR VOMITING | British Medical Journal. Vol. 291, Pg. 448, 1985. |
women | TDLo | unreported | 900mg/kg/30W- (900mg/kg) | BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA | American Journal of Medicine. Vol. 87, Pg. 468, 1989. |
Safety Information of Deferoxamine mesylate (CAS NO.138-14-7):
Safety Statements: 22-24/25
S22:Do not breathe dust.
S24/25:Avoid contact with skin and eyes.
WGK Germany: 2
RTECS: UG5310000
Poison by intravenous route. Moderately toxic by subcutaneous and intraperitoneal routes. Mildly toxic by ingestion. Human systemic effects: acute pulmonary edema, blood changes, cardiomyopathy, degenerative brain changes, diarrhea, hypermotility, nausea or vomiting, pericarditis, ulceration or bleeding from small intestine, visual field changes. When heated to decomposition it emits toxic fumes of NOx and SOx.
Deferoxamine mesylate (CAS NO.138-14-7), its Synonyms are Butanediamide, N'-(5-((4-((5-(acetylhydroxyamino)pentyl)amino)-1,4-dioxobutyl)hydroxyamino)pentyl)-N-(5-aminopentyl)-N-hydroxy-, monomethanesulfonate ; Desferal methanesulfonate ; Desferrioxamine B mesylate ; Desferrioxamine B methanesulfonate ; Desferrioxamine mesylate ; Desferrioxamine methanesulfonate ; N-(5-(3-((5-Aminopentyl)hydroxycarbamoyl)propionamido)pentyl)-3-((5-(N-hydroxyacetamido)pentyl)carbamoyl)propionohydroxamic acid monomethanesulfonate (salt) .
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