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CAS No.: | 219989-84-1 |
---|---|
Name: | IXABEPILONE |
Article Data: | 6 |
Molecular Structure: | |
Formula: | C27H42N2O5S |
Molecular Weight: | 506.707 |
Synonyms: | AzaepothiloneB;BMS 247550;BMS 247550-1;Ixempra; |
EINECS: | 630-424-7 |
Density: | 1.122 g/cm3 |
Boiling Point: | 697.815 °C at 760 mmHg |
Flash Point: | 375.825 °C |
PSA: | 140.29000 |
LogP: | 4.37930 |
[4S-[4R*,7S*,8R*,9R*,15R*(E)]]-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-1-aza-13(Z)-cyclohexadecene-2,6-dione
ixabepilone
Conditions | Yield |
---|---|
With DMDO In dichloromethane at -78 - -50℃; for 1h; | 69% |
With 3,3-dimethyldioxirane In dichloromethane; acetone at -78 - -50℃; for 1.5h; Inert atmosphere; | 42.8% |
With 3-chloro-benzenecarboperoxoic acid In chloroform at -20 - -15℃; for 4h; Inert atmosphere; | 0.31 g |
ixabepilone
Conditions | Yield |
---|---|
With diphenyl phosphoryl azide; sodium hydrogencarbonate In N,N-dimethyl-formamide at 0 - 4℃; for 24h; Inert atmosphere; | 40% |
(3S,6R,7S,8S)-11-((2R,3S)-3-((S,E)-2-amino-3-methyl-4-(2-methylthiazol-4-yl)but-3-enyl)-2-methyloxiran-2-yl)-3,7-dihydroxy-4,4,6,8-tetramethyl-5-oxoundecanoic acid
ixabepilone
Conditions | Yield |
---|---|
With diphenyl-phosphinic acid; sodium hydrogencarbonate In N,N-dimethyl-formamide at 4℃; for 24h; | 43% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide; acetonitrile at 0 - 30℃; for 12h; Inert atmosphere; | 3.2 g |
C29H47N3O7S
ixabepilone
Conditions | Yield |
---|---|
With diphenyl phosphoryl azide; sodium hydrogencarbonate In N,N-dimethyl-formamide at 0℃; for 24h; Inert atmosphere; |
(3S,6R,7S,8S)-11-((2R,3S)-3-((S,E)-2-azido-3-methyl-4-(2-methylthiazol-4-yl)but-3-enyl)-2-methyloxiran-2-yl)-3,7-dihydroxy-4,4,6,8-tetramethyl-5-oxoundecanoic acid
ixabepilone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 71 percent / PMe3; H2O / tetrahydrofuran; toluene / 2 h / 25 °C 2: 43 percent / DPPA; NaHCO3 / dimethylformamide / 24 h / 4 °C View Scheme | |
Multi-step reaction with 2 steps 1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere View Scheme |
epothilone B
ixabepilone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.5 h / 25 °C / Inert atmosphere 1.2: 1 h / 45 °C 2.1: triphenylphosphine / tetrahydrofuran / 14 h / 45 °C / Inert atmosphere 2.2: 4 h / 45 °C 3.1: sodium hydrogencarbonate; diphenyl phosphoryl azide / N,N-dimethyl-formamide / 24 h / 0 - 4 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere 2: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere 3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere View Scheme |
(Z)-(6R,7S,8S)-3-Methoxy-4,4,6,8-tetramethyl-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-undeca-2,10-dienoic acid tert-butyl ester
ixabepilone
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1: tetrahydrofuran / 1 h / 25 °C 2: 70 percent / Pd(dppf)Cl2*CH2Cl2; AsPh3; Cs2CO3 / dimethylformamide; H2O; tetrahydrofuran / 2 h 3: tetrahydrofuran / 19 h / 40 °C 4: 3.9 g / H2O / tetrahydrofuran / 4 h / 65 °C 5: 70 percent / Et3N / acetonitrile / 16 h / 20 °C 6: 82 percent / p-TsOH / acetone / 22 h / 20 °C 7: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr 8: TFA / CH2Cl2 / 2 h / 20 °C 9: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C 10: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C 11: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C View Scheme |
(5R)-5-hydroxy-2-iodo-6-methyl-7-(2-methylthiazol-4-yl)-2,6-heptadiene
ixabepilone
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1: 85 percent / diphenylphosphoryl azide; DBU / toluene / 2 h / 2 - 25 °C 2: 70 percent / Pd(dppf)Cl2*CH2Cl2; AsPh3; Cs2CO3 / dimethylformamide; H2O; tetrahydrofuran / 2 h 3: tetrahydrofuran / 19 h / 40 °C 4: 3.9 g / H2O / tetrahydrofuran / 4 h / 65 °C 5: 70 percent / Et3N / acetonitrile / 16 h / 20 °C 6: 82 percent / p-TsOH / acetone / 22 h / 20 °C 7: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr 8: TFA / CH2Cl2 / 2 h / 20 °C 9: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C 10: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C 11: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C View Scheme |
(5S)-5-azido-2-iodo-6-methyl-7-(2-methylthiazol-4-yl)-2,6-heptadiene
ixabepilone
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1: 70 percent / Pd(dppf)Cl2*CH2Cl2; AsPh3; Cs2CO3 / dimethylformamide; H2O; tetrahydrofuran / 2 h 2: tetrahydrofuran / 19 h / 40 °C 3: 3.9 g / H2O / tetrahydrofuran / 4 h / 65 °C 4: 70 percent / Et3N / acetonitrile / 16 h / 20 °C 5: 82 percent / p-TsOH / acetone / 22 h / 20 °C 6: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr 7: TFA / CH2Cl2 / 2 h / 20 °C 8: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C 9: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C 10: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C View Scheme |
ixabepilone
Conditions | Yield |
---|---|
Multi-step reaction with 12 steps 1: 99 percent / aq. AcOH / tetrahydrofuran / 8 h / 20 °C 2: 85 percent / diphenylphosphoryl azide; DBU / toluene / 2 h / 2 - 25 °C 3: 70 percent / Pd(dppf)Cl2*CH2Cl2; AsPh3; Cs2CO3 / dimethylformamide; H2O; tetrahydrofuran / 2 h 4: tetrahydrofuran / 19 h / 40 °C 5: 3.9 g / H2O / tetrahydrofuran / 4 h / 65 °C 6: 70 percent / Et3N / acetonitrile / 16 h / 20 °C 7: 82 percent / p-TsOH / acetone / 22 h / 20 °C 8: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr 9: TFA / CH2Cl2 / 2 h / 20 °C 10: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C 11: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C 12: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C View Scheme |
The Ixabepilone, with the CAS registry number 219989-84-1, is also known as Azaepothilone B. This chemical's molecular formula is C27H42N2O5S and molecular weight is 506.70. What's more, its systematic name is (1R,5S,6S,7R,10S,14S,16S)-6,10-dihydroxy-1,5,7,9,9-pentamethyl-14-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-17-oxa-13-azabicyclo[14.1.0]heptadecane-8,12-dione. Its classification codes are: (1)Antimitotic; (2)Antineoplastic; (3)Antineoplastic Agents. Ixabepilone, in combination with capecitabine, has demonstrated effectiveness in the treatment of metastatic or locally advanced breast cancer in patients after failure of an anthracycline and a taxane. It has been investigated for use in treatment of non-Hodgkin's lymphoma.
Physical properties of Ixabepilone are: (1)ACD/LogP: 1.772; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 1.77; (4)ACD/LogD (pH 7.4): 1.77; (5)ACD/BCF (pH 5.5): 13.07; (6)ACD/BCF (pH 7.4): 13.09; (7)ACD/KOC (pH 5.5): 218.97; (8)ACD/KOC (pH 7.4): 219.36; (9)#H bond acceptors: 7; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 140.29 Å2; (13)Index of Refraction: 1.532; (14)Molar Refractivity: 140.117 cm3; (15)Molar Volume: 451.556 cm3; (16)Polarizability: 55.547×10-24cm3; (17)Surface Tension: 40.93 dyne/cm; (18)Density: 1.122 g/cm3; (19)Flash Point: 375.825 °C; (20)Enthalpy of Vaporization: 107.302 kJ/mol; (21)Boiling Point: 697.815 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES: Cc3nc(/C=C(\C)[C@@H]1C[C@@H]2O[C@]2(C)CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)N1)cs3
(2)Std. InChI: InChI=1S/C27H42N2O5S/c1-15-9-8-10-27(7)22(34-27)12-20(16(2)11-19-14-35-18(4)28-19)29-23(31)13-21(30)26(5,6)25(33)17(3)24(15)32/h11,14-15,17,20-22,24,30,32H,8-10,12-13H2,1-7H3,(H,29,31)/b16-11+/t15-,17+,20-,21-,22-,24-,27+/m0/s1
(3)Std. InChIKey: FABUFPQFXZVHFB-PVYNADRNSA-N