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[ CAS No. 30562-34-6 ] {[proInfo.proName]}

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Chemical Structure| 30562-34-6
Chemical Structure| 30562-34-6
Structure of 30562-34-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 30562-34-6 ]

CAS No. :30562-34-6 MDL No. :MFCD00274570
Formula : C29H40N2O9 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :560.64 Pubchem ID :-
Synonyms :
Geldanamycin

Calculated chemistry of [ 30562-34-6 ]

Physicochemical Properties

Num. heavy atoms : 40
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.52
Num. rotatable bonds : 5
Num. H-bond acceptors : 9.0
Num. H-bond donors : 3.0
Molar Refractivity : 151.03
TPSA : 163.48 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -8.31 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.84
Log Po/w (XLOGP3) : 1.99
Log Po/w (WLOGP) : 2.03
Log Po/w (MLOGP) : -0.54
Log Po/w (SILICOS-IT) : 0.74
Consensus Log Po/w : 1.41

Druglikeness

Lipinski : 2.0
Ghose : None
Veber : 1.0
Egan : 1.0
Muegge : 1.0
Bioavailability Score : 0.11

Water Solubility

Log S (ESOL) : -4.24
Solubility : 0.0323 mg/ml ; 0.0000576 mol/l
Class : Moderately soluble
Log S (Ali) : -5.05
Solubility : 0.005 mg/ml ; 0.00000893 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -3.25
Solubility : 0.313 mg/ml ; 0.000558 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 7.71

Safety of [ 30562-34-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 30562-34-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 30562-34-6 ]
  • Downstream synthetic route of [ 30562-34-6 ]

[ 30562-34-6 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 107-11-9 ]
  • [ 30562-34-6 ]
  • [ 75747-14-7 ]
YieldReaction ConditionsOperation in experiment
99% at 20℃; for 18 h; (+) -Geldanamycin (5.1 mg, 9. 0 mol) was stirred with allylamine (10.0 ul, 0.13 mmol) in chloroform (1.5 ml) at room temperature. Upon the complete conversion of GA shown by thin layer chromatography (18 hours), the mixture was washed with brine, dried over anhydrous sodium sulfate, and concentrated. Separation by flash column chromatography on silica gel (hexane/ethyl acetate) gave the product as a purple solid (5.3 mg, 99percent). IR (KBr) (can~') 3464,3333, 2958,2929, 2825,1728, 1691,1652, 1571,1485, 1372,1323, 1189,1101, 1057; UV (95percent EtOH) (nm) 332 (s = 2. 0 x 104) ;'H NMR (CDC13, 500 MHz) 8 9. 14 (s, 1H), 7.28 (s, 1H), 6.93 (bd, J= 11.5 Hz, 1H), 6.56 (bdd, J= 11. 5,11. 0 Hz, 1H), 6.38 (bt, J= 6. 0 Hz, 1H), 5.94-5. 81 (m, 3H), 5.30-5. 24 (m, 2H), 5.17 (s, 1H), 4.82 (bs, 2H), 4.29 (bd, J= 10.0 Hz, 1H), 4.21 (bs, 1H), 4.18-4. 08 (m, 2H), 3.55 (ddd, J= 9.0, 6.5, 2.0 Hz, 1H), 3.43 (ddd, J= 9.0, 3.0, 3.0 Hz, 1H), 3. 34 (s, 3H), 3.25 (s, 3H), 2.72 (dqd, J= 9.5, 7.0, 2.0 Hz, 1H), 2.63 (d, J= 14.0 Hz, 1H), 2.34 (dd, J= 14. 0,11. 0 Hz, 1H), 2.00 (bs, 3H), 1.78 (d, J= 1.0 Hz, 3H), 1.78-1. 74 (m, 2H), 1.74-1. 67 (m, 1H), 0.99-0. 95 (m, 6H) ; 3C NMR (CDC13, 125 MHz, assignment of protonated carbons aided by DEPT) 8 183.8 (18-C), 180.9 (21-C), 168.4 (1-C), 156.0 (7- OzCNHz), 144.6 (17-C), 141.2 (20-C), 135.8 (5-C), 134.9 (2-C), 133.7 (9-C), 132.7 (8-C), 132.5 (3'-C), 126.9 (4-C), 126.5 (3-C), 118.5 (3'-C), 108.8 (19-C), 108.7 (16-C), 81.6 (7-C), 81.4 (12-C), 81.2 (6-C), 72.6 (11-C), 57.1 (6-or 12-OCH3), 56.7 (6-or 12-OCH3), 47.8 (1'-C), 35.0 (13-C), 34.3 (15-C), 32.3 (10-C), 28.4 (14-C), 22.9 (14-CH3), 12.8 (8-CH3), 12.6 (2-CH3), 12.3 (10-CH3); HRMS (FAB) found 586.3120 [M+H] +, calcd. 586.3129 for C31H44N30g.
95% at 23℃; 17-AAG was synthesized in the lab from geldanamycin (GA) (LC Laboratories, Woburn, MA). Briefly, 100 mg of GA (0.2 mmol) was dissolved in 2 mL of dry CH2Cl2. Next, 5 equivalents of allylamine (57.1 g/mol, d = 0.763 g/mL) was added dropwise to the flask. The reaction was stirred at room temperature (RT; ∼23 °C) under low light until complete by TLC analysis (approx. 2 days) (95:5 CHCl3:MeOH, Rf 0.21), precipitated with hexane (3x), centrifuged at 2000 g's for 15 minutes, and evaporated to dryness. Yield: 95 mg, 95percent; MS m/z 584 (M-); 1H NMR (CDCl3) δ 0.99 (m, 6H, 10-Me, 14-Me), 1.25 (t, 1H, H-13), 1.60-1.85 (br m, 6H, H-13, H-14, 8-Me), 2.05 (s, 3H, 2-Me), 2.46 (br m, 2H, H-15), 2.83-2.90 (br m, 3H, H-10), 3.27 (s, 3H, OMe), 3.36 (s, 3H, OMe), 3.40 (t, 1H, H-12), 3.58-3.68 (br m, 2H, H-11, H-23), 4.31 (d, 1H, H-7), 5.10 (br s, 1H), 5.21-5.55 (br m, 3H, H-9, H-24), 5.86-5.99 (br t, 2H, H-5, H-23), 6.59 (t, 1H, H-4), 6.94 (d, 1H, H-3), 7.28 (br s, 1H, H-19).
82.6% at 20℃; for 4 h; To 45.0 g (80.4 mmol) of geldanamycin in 1.45 L of dry THF in a dry 2 L flask was added drop-wise over 30 minutes 36.0 mL (470 mmol) of allyl amine in 50 mL of dry THF. The reaction mixture was stirred at room temperature under nitrogen for 4 hr at which time TLC analysis indicated the reaction was complete [(GDM: bright yellow: Rf=0.40; (5percent MeOH-95percent CHCl3); 17-AAG: purple: Rf=0.42 (5percent MeOH-95percent CHCl3)]. The solvent was removed by rotary evaporation and the crude material was slurried in 420 mL of H2O:EtOH (90:10) at 25° C., filtered and dried at 45° C. for 8 hr to give 40.9 g (66.4 mmol) of 17-AAG as purple crystals (82.6percent yield, >98percent pure by HPLC monitored at 254 nm). MP 206-212° C. 1H NMR and HPLC are consistent with the desired product.
82.6% at 20℃; for 4.5 h; To 45.0 g (80.4 mmol) of geldanamycin in 1.45 L of dry THF in a dry 2 L flask was added drop-wise over 30 minutes 36.0 mL (470 mmol) of allyl amine in 50 mL of dry THF. The reaction mixture was stirred at room temperature under nitrogen for 4 hr at which time TLC analysis indicated the reaction was complete [(GDM: bright yellow: Rf=0.40; (5percent MeOH-95percent CHCl3); 17-AAG: purple: Rf=0.42 (5percent MeOH-95percent CHCl3)]. The solvent was removed by rotary evaporation and the crude material was slurried in 420 mL of H2O:EtOH (90:10) at 25° C., filtered and dried at 45° C. for 8 hr to give 40.9 g (66.4 mmol) of 17-AAG as purple crystals (82.6percent yield, >98percent pure by HPLC monitored at 254 nm). m.p. 206-212° C. 1H NMR and HPLC are consistent with the desired product.
82.6% at 20℃; for 4.5 h; To 45.0 g (80.4 mmol) of geldanamycin in 1.45 L of dry THF in a dry 2 L flask was added drop-wise over 30 minutes, 36.0 mL (470 mmol) of allyl amine in 50 mL of dry THF. The reaction mixture was stirred at room temperature under nitrogen for 4 hr at which time TLC analysis indicated the reaction was complete [(GDM: bright yellow: Rf=0.40; (5percent MeOH-95percentCHCl3); 17-AAG: purple: Rf=0.42 (5percent MeOH-95percent CHCl3)]. The solvent was removed by rotary evaporation and the crude material was slurried in 420 mL of H2O:EtOH (90:10) at 25° C., filtered and dried at 45° C. for 8 hr to give 40.9 g (66.4 mmol) of 17 purple crystals (82.6percent yield, >98percent pure by HPLC monitored at 254 nm). MP 206-212° C. as determined using differential scanning colorimetry (DSC). 1H NMR and HPLC are consistent with the desired product.
77% at 20℃; for 6 h; To a solution of geldanamycin (20.0 g, 35.7 mmol, 1 eq.) in DCM (750 mL) was added allylamine (53 mL, 714 mmol, 20 eq) at room temperature and under nitrogen atmosphere.
The slurry was stirred at room temperature for 6 hours.
The resulting purple solution was quenched with water (300 mL) and acidified with 2N HCl (300 mL) to pH 3 and stirred for and additional 30 min.
The aqueous phase was extracted with DCM (300 mL) and the combined organic layers washed with water (300 mL), dried over MgSO4, filtered, and concentrated.
The purple residue was dissolved into acetone (300 mL) at 60° C. and heptanes (1.5 L) was added and the resulting mixture cooled to 5° C., filtered, and the solid washed with heptane (200 mL) to afford crude 17-AAG (18.15 g) after drying.
The purple solid was dissolved in of acetone (306 mL) heated to 55-60° C. and n-heptane (1.2 L) was slowly added to form a slurry.
The mixture was maintained at 55° C. for 30 minutes and cooled to room temperature.
The crystalline material was collected and dried under vacuum for 48 hours to afford 17-AAG as purple needles. (16.15 g, 28 mmol, 77percent yield).
>99percent pure by HPLC monitoredat;254 nm) mp 210-212° C.

Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 10, p. 2939 - 2943
[2] Patent: WO2005/95347, 2005, A1, . Location in patent: Page/Page column 33
[3] Patent: EP2480207, 2016, B1, . Location in patent: Paragraph 0091
[4] Patent: US2006/67953, 2006, A1, . Location in patent: Page/Page column 14
[5] Patent: US2006/228405, 2006, A1, . Location in patent: Page/Page column 12
[6] Patent: US2007/129342, 2007, A1, . Location in patent: Page/Page column 9
[7] Patent: US2008/221077, 2008, A1, . Location in patent: Page/Page column 23
[8] Patent: WO2005/63714, 2005, A1, . Location in patent: Page/Page column 111
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