amphotericin B methyl ester
AmBisome
Conditions | Yield |
---|---|
With lithium hydroxide In tetrahydrofuran; water at 25℃; for 1h; | 80% |
4-formylphenylcarbonyl-terminated poly(ethylene glycol)-poly[Nε-(4-formylphenyl-carbonyl)-L-lysine] amphotericin B Schiff's base, block copolymer, Mw = 26700, Mw/Mn = 1.11
AmBisome
Conditions | Yield |
---|---|
With water In phosphate buffer at 37℃; pH=5.5; Kinetics; |
AmBisome
Conditions | Yield |
---|---|
With phosphate buffer In methanol at 37℃; pH=5.5; Kinetics; Acid hydrolysis; |
poly(ethylene glycol), Mw 10000 (of polyethylene glycol chain), conjugated with amphotericin B through O,O'-bis(1,4-C(O)C6H4-C=)-linker, in molar ratio 1:2
AmBisome
Conditions | Yield |
---|---|
With phosphate buffer In methanol at 37℃; pH=5.5; Kinetics; Acid hydrolysis; |
poly(ethylene glycol), Mw 20000 (of polyethylene glycol chain), conjugated with amphotericin B through O,O'-bis-(1,4-C(O)C6H4-C=)-linker, in molar ratio 1:2
AmBisome
Conditions | Yield |
---|---|
With phosphate buffer In methanol at 37℃; pH=5.5; Kinetics; Acid hydrolysis; |
AmBisome
Conditions | Yield |
---|---|
With phosphate buffer In methanol at 37℃; pH=5.5; Kinetics; Acid hydrolysis; |
AmBisome
Conditions | Yield |
---|---|
With phosphate buffer In methanol at 37℃; pH=5.5; Kinetics; Acid hydrolysis; |
AmBisome
Conditions | Yield |
---|---|
With phosphate buffer In methanol at 37℃; pH=5.5; Kinetics; Acid hydrolysis; |
AmBisome
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) CSA; 2.) H2O / 1.) MeOH, 25 deg C, 2 h; 2.) MeOH, 25 deg C, 4 h 2: 80 percent / LiOH / tetrahydrofuran; H2O / 1 h / 25 °C View Scheme |
AmBisome
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 90 percent / HS(CH2)3SH, Et3N / methanol / 24 h / 25 °C 2: 1.) CSA; 2.) H2O / 1.) MeOH, 25 deg C, 2 h; 2.) MeOH, 25 deg C, 4 h 3: 80 percent / LiOH / tetrahydrofuran; H2O / 1 h / 25 °C View Scheme |
amphotericin B methyl pivalate
AmBisome
Conditions | Yield |
---|---|
With water In dimethyl sulfoxide at 37℃; pH=7; Phosphate buffer; Enzymatic reaction; |
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
AmBisome
3′-N-Fmoc-AmB
Conditions | Yield |
---|---|
With pyridine In N,N-dimethyl-formamide at 20℃; for 18h; | 100% |
With pyridine In methanol; N,N-dimethyl-formamide at 23℃; for 4h; | 99% |
With pyridine In methanol; N,N-dimethyl-formamide at 20℃; for 12h; | 95% |
Conditions | Yield |
---|---|
With pyridine In methanol; N,N-dimethyl-formamide at 23℃; for 16h; Inert atmosphere; | 100% |
In methanol; N,N-dimethyl-formamide at 23℃; for 16h; | 100% |
With pyridine In methanol; N,N-dimethyl-formamide at 23℃; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With pyridine In methanol; N,N-dimethyl-formamide | 99% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere; | 97% |
AmBisome
L-histidine methyl ester
Conditions | Yield |
---|---|
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dimethyl sulfoxide at 23 - 25℃; for 24h; Reagent/catalyst; Solvent; Inert atmosphere; Darkness; | 97% |
Conditions | Yield |
---|---|
With diphenyl phosphoryl azide; triethylamine In N,N-dimethyl acetamide at 20℃; | 95.5% |
With triethylamine In N,N-dimethyl acetamide at 20℃; Inert atmosphere; |
Conditions | Yield |
---|---|
With diphenyl phosphoryl azide; triethylamine In N,N-dimethyl acetamide at 20℃; Darkness; Inert atmosphere; | 95.09% |
Conditions | Yield |
---|---|
Michael Addition; | 94.6% |
(R)-(+)-tryptophan methyl ester hydrochloride
AmBisome
Conditions | Yield |
---|---|
With diphenyl phosphoryl azide; triethylamine In N,N-dimethyl acetamide at 20℃; | 93.85% |
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide | 93.3% |
Conditions | Yield |
---|---|
Michael Addition; | 92.2% |
AmBisome
poly(ethylene glycol), Mw 20000 (of polyethylene glycol chain), conjugated with amphotericin B through O,O'-bis-(1,4-C(O)C6H4-C=)-linker, in molar ratio 1:2
Conditions | Yield |
---|---|
With 4 A molecular sieve; trimethyl orthoformate In N,N-dimethyl-formamide at 20℃; | 92% |
Conditions | Yield |
---|---|
With diphenyl phosphoryl azide; triethylamine In N,N-dimethyl acetamide at 20℃; for 12h; Inert atmosphere; Darkness; | 92% |
AmBisome
1-(2-tert-butylphenyl)-1H-pyrrole-2,5-dione
N-(N-2-tert-butylphenylsuccinimidyl)-amphotericin B
Conditions | Yield |
---|---|
Michael Addition; | 91.9% |
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide | 91.1% |
1-(2,4,6-trimethylphenyl)pyrrole-2,5-dione
AmBisome
N-(N-2,4,6-trimethylphenylsuccinimidyl)-amphotericin B
Conditions | Yield |
---|---|
Michael Addition; | 89.9% |
Stage #1: AmBisome With triethylamine In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: 1-(2,4,6-trimethylphenyl)pyrrole-2,5-dione In N,N-dimethyl-formamide at 20℃; | 30 mg |
AmBisome
N-(N-methyl-Oγ-tert-butyl-L-glutamyl)amphotericin B
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide | 89.9% |
AmBisome
1-[(pyridin-4-yl)methyl]pyrrole-2,5-dione
Conditions | Yield |
---|---|
Michael Addition; | 89.7% |
AmBisome
(2R)-2-amino-4-tert-butoxy-4-oxobutanoic acid
N-(Oβ-tert-butyl-D-aspartyl)amphotericin B
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide | 88.4% |
1-benzyl-1H-pyrrole-2,5-dione
AmBisome
N-(N-benzylsuccinimidyl)-amphotericin B
Conditions | Yield |
---|---|
Michael Addition; | 88% |
1-piperidinepropionic acid
AmBisome
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide | 87.9% |
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide | 87.6% |
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide | 87% |
AmBisome
4-formylphenylcarbonyl-terminated poly(ethylene glycol)-poly[Nε-(4-formylphenyl-carbonyl)-L-lysine] amphotericin B Schiff's base, block copolymer, Mw = 26700, Mw/Mn = 1.11
Conditions | Yield |
---|---|
With 4 A molecular sieve; trimethyl orthoformate | 86% |
AmBisome
Conditions | Yield |
---|---|
With 4 A molecular sieve; trimethyl orthoformate In N,N-dimethyl-formamide at 20℃; | 86% |
1-[3-(N,N-dimethylamino)-2,2-dimethylpropyl]-pyrrole-2,5-dione
AmBisome
N-{N-[3-(N,N-dimethylamino)-2,2-dimethylpropyl]-succinimidyl}-amphotericin B
Conditions | Yield |
---|---|
Michael Addition; | 85.5% |
AmBisome
N-[β-(pyridine-1-yl)-D-alanyl]amphotericin B
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide | 85.3% |
AmBisome
6-(9H-fluoren-9-ylmethoxycarbonylamino)hexanoic acid 2,5-dioxopyrrolidin-1-yl ester
N-(Fmoc-6-aminohexanoyl)-amphotericin B
Conditions | Yield |
---|---|
With pyridine In N,N-dimethyl-formamide for 20h; | 85% |
Conditions | Yield |
---|---|
With 4 A molecular sieve; trimethyl orthoformate In dimethyl sulfoxide at 25℃; for 48h; | 84% |
AmBisome
poly(ethylene glycol), Mw 10000 (of polyethylene glycol chain), conjugated with amphotericin B through O,O'-bis(1,4-C(O)C6H4-C=)-linker, in molar ratio 1:2
Conditions | Yield |
---|---|
With 4 A molecular sieve; trimethyl orthoformate In N,N-dimethyl-formamide at 20℃; | 83% |
The Amphotericin B, with the CAS registry number 1397-89-3,is also known as 33-[(3-Amino-3,6-dideoxy-beta-D-mannopyranosyl)oxy]-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-Dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid; Fungizone. It belongs to the product categories of Antifungal;Carbohydrates & Derivatives;Chiral Reagents. This chemical's molecular formula is C47H73NO17 and molecular weight is 924.08.Its EINECS number is 215-742-2. What's more,Its systematic name is Amphotericin B.It is a Crystalline Yellow Solid which is stable,incompatible with strong oxidizing agents,but may be light sensitive. It is a kind of polyene antifungal drugs,Isolated from Streptomyces culture.
Physical properties about Amphotericin B are:
(1)ACD/LogP: 1.164; (2)# of Rule of 5 Violations: 3; (3)ACD/LogD (pH 5.5): -1.34; (4)ACD/LogD (pH 7.4): -1.41; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 18; (10)#H bond donors: 13; (11)#Freely Rotating Bonds: 14; (12)Index of Refraction: 1.614; (13)Molar Refractivity: 240.249 cm3; (14)Molar Volume: 689.435 cm3; (15)Surface Tension: 71.6880035400391 dyne/cm; (16)Density: 1.34 g/cm3; (17)Flash Point: 643.47 °C; (18)Enthalpy of Vaporization: 189.982 kJ/mol; (19)Boiling Point: 1140.365 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES:C[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@@H](C[C@H]2[C@@H]([C@H](C[C@](O2)(C[C@H](C[C@H]([C@@H](CC[C@H](C[C@H](CC(=O)O[C@H]([C@@H]([C@@H]1O)C)C)O)O)O)O)O)O)O)C(=O)O)O[C@H]3[C@H]([C@H]([C@@H]([C@H](O3)C)O)N)O;
(2)Std. InChI:InChI=1S/C47H73NO17/c1-27-17-15-13-11-9-7-5-6-8-10-12-14-16-18-34(64-46-44(58)41(48)43(57)30(4)63-46)24-38-40(45(59)60)37(54)26-47(61,65-38)25-33(51)22-36(53)35(52)20-19-31(49)21-32(50)23-39(55)62-29(3)28(2)42(27)56/h5-18,27-38,40-44,46,49-54,56-58,61H,19-26,48H2,1-4H3,(H,59,60)/b6-5+,9-7+,10-8+,13-11+,14-12+,17-15+,18-16+/t27-,28-,29-,30+,31+,32+,33-,34-,35+,36+,37-,38-,40+,41-,42+,43+,44-,46-,47+/m0/s1;
(3)Std. InChIKey:APKFDSVGJQXUKY-INPOYWNPSA-N.
Safety Information of Amphotericin B:
The Amphotericin B is irritating to eyes, respiratory system and skin and harmful if swallowed.But there is limited evidence of a carcinogenic effect.It is toxic by inhalation, in contact with skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. When you use it ,wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) .
The toxicity data of Amphotericin B as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LD50 | intravenous | 6mg/kg (6mg/kg) | KIDNEY, URETER, AND BLADDER: OTHER CHANGES | Biokhimiya Vol. 43, Pg. 2043, 1978. |
infant | TDLo | intravenous | 15mg/kg/4D-I (15mg/kg) | Journal of Toxicology, Clinical Toxicology. Vol. 28, Pg. 371, 1990. | |
infant | TDLo | intravenous | 15mg/kg/4D-I (15mg/kg) | Journal of Toxicology, Clinical Toxicology. Vol. 28, Pg. 371, 1990. | |
man | LDLo | intravenous | 164ug/kg/5H-I (0.164mg/kg) | CARDIAC: OTHER CHANGES | Drug Intelligence and Clinical Pharmacy. Vol. 17, Pg. 547, 1983. |
mouse | LD | unreported | > 50mg/kg (50mg/kg) | Journal of Antibiotics. Vol. 24, Pg. 561, 1971. | |
mouse | LD12 | oral | 280mg/kg (280mg/kg) | British UK Patent Application. Vol. #2067993, | |
mouse | LD50 | intramuscular | > 5gm/kg (5000mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 7, Pg. 108, 1976. | |
mouse | LD50 | intraperitoneal | 27740ug/kg (27.74mg/kg) | National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986, | |
mouse | LD50 | intravenous | 1200ug/kg (1.2mg/kg) | Pharmacy International. Vol. 6, Pg. 164, 1985. | |
rabbit | LDLo | intravenous | 5mg/kg (5mg/kg) | BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Antibiotics Annual. Vol. 5, Pg. 53, 1957/1958. |
rat | LD50 | intramuscular | > 5gm/kg (5000mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 7, Pg. 108, 1976. | |
rat | LD50 | intraperitoneal | > 5gm/kg (5000mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 7, Pg. 108, 1976. | |
rat | LD50 | intravenous | 1600ug/kg (1.6mg/kg) | Journal of Antimicrobial Chemotherapy. Vol. 28(Suppl, | |
rat | LD50 | oral | > 5gm/kg (5000mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 7, Pg. 108, 1976. | |
women | LDLo | intravenous | 22mg/kg/4D-I (22mg/kg) | BLOOD: LEUKOPENIA | Southern Medical Journal. Vol. 76, Pg. 409, 1983. |
women | TDLo | intravenous | 20ug/kg (0.02mg/kg) | LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | New England Journal of Medicine. Vol. 315, Pg. 836, 1986. |
women | TDLo | intravenous | 1mg/kg/1H-C (1mg/kg) | CARDIAC: PULSE RATE | Lancet. Vol. 341, Pg. 372, 1993. |
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