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[ CAS No. 23541-50-6 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
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Inaccessible (Haz class 6.1), Domestic USD 80+
Inaccessible (Haz class 6.1), International USD 150+
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Chemical Structure| 23541-50-6
Chemical Structure| 23541-50-6
Structure of 23541-50-6 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 23541-50-6 ]

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Product Citations

Product Details of [ 23541-50-6 ]

CAS No. :23541-50-6 MDL No. :MFCD04974507
Formula : C27H30ClNO10 Boiling Point : No data available
Linear Structure Formula :- InChI Key :GUGHGUXZJWAIAS-QQYBVWGSSA-N
M.W : 563.98 Pubchem ID :62770
Synonyms :
RP 1357 HCl; Daunomycin HCl; Rubidomycin HCl
Chemical Name :(8S,10S)-8-Acetyl-10-(((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione hydrochloride

Calculated chemistry of [ 23541-50-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 39
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.44
Num. rotatable bonds : 4
Num. H-bond acceptors : 11.0
Num. H-bond donors : 5.0
Molar Refractivity : 138.47
TPSA : 185.84 ?2

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 : Yes
Log Kp (skin permeation) : -7.87 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.63
Log Po/w (WLOGP) : 1.51
Log Po/w (MLOGP) : -1.15
Log Po/w (SILICOS-IT) : 1.77
Consensus Log Po/w : 0.95

Druglikeness

Lipinski : 2.0
Ghose : None
Veber : 1.0
Egan : 1.0
Muegge : 2.0
Bioavailability Score : 0.17

Water Solubility

Log S (ESOL) : -4.96
Solubility : 0.00622 mg/ml ; 0.000011 mol/l
Class : Moderately soluble
Log S (Ali) : -6.18
Solubility : 0.00037 mg/ml ; 0.000000656 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -4.04
Solubility : 0.0516 mg/ml ; 0.0000914 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 5.84

Safety of [ 23541-50-6 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P261-P281-P301+P310 UN#:2811
Hazard Statements:H301-H334-H351 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 23541-50-6 ]

* 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.

  • Downstream synthetic route of [ 23541-50-6 ]

[ 23541-50-6 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 34270-90-1 ]
  • [ 23541-50-6 ]
  • [ 79867-78-0 ]
YieldReaction ConditionsOperation in experiment
55% With triethylamine; In DMF (N,N-dimethyl-formamide); at 20℃; for 36h; 3.1 Preparation of Y1-IgG-M-Daunorubicin Derivative: Antibody-toxin conjugates such as morpholino-doxorubicin-Y1-IgG (FIG. 13) and antibody-M-daunorubicin conjugates (see below) were prepared. Daunorubicin was modified, joined to one of two different linkers, and then joined to the antibody via the antibody's free amino groups or via the antibody's reduced disulfide bonds. The term M-DNR-LINKER refers to both (6-Maleimidocaproyl)hydrazone of Morphlinyldaunorubicin acetate and to M-DNR-AES. a. Preparation of 3'-Deamino-3'-(4-morpholinyl)daunorubicin acetate (M-DNR-Ac) Dry triethylamine was added to a solution of daunorubicin hydrochloride in dry dimethylformamide, under argon, followed by <strong>[34270-90-1]bis(2-iodoethyl) ether</strong>. The reaction mixture was protected from light and stirred for 36 hours at room temperature. The resulting aqueous mixture was extracted with methylene chloride. The organic phase was dried over anhydrous sodium sulfate, filtered through celite and evaporated to dryness. The crude product was purified by silica gel column chromatography, and the relevant fractions pooled together and evaporated to yield the M-DNR free base as a red oil, which was found to be 98% pure (by HPLC). The yield was 55%. After reaction with acetic acid, the resulting free base was isolated as its solid acetate salt followed by lyophilization. M-DNR-Ac is stable for at least 12 months under argon at -20 C. b. Preparation of (6-Maleimidocaproyl)hydrazone of Morphlinyldaunorubicin acetate 6-maleimidocaproylhydrazide was added to a solution of M-DNR-Ac in dry methanol, under argon, followed by trifluoroacetic acid. The clear solution was protected from light and stirred for 24 hours at room temperature. The methanolic solution was evaporated to dryness under reduced pressure at 25 C., resulting in a red oily residue, which was dissolved in dry methanol. To this solution, dry ether was added and the precipitated red solid isolated by centrifugation. The pure crystalline product, which had a purity of 98% and a yield of 88%, was obtained after three triturations with dry ether, dried under high vacuum, and kept under argon at -20 C. (6-Maleimidocaproyl)hydrazone of Morphlinyldaunorubicin acetate is stable for at least 4 months under argon at -20 C. c. Preparation of N-hydroxysuccimimide Ester of Adipic Acid Monohydrazone of Morpholinodaunorubicin (M-DNR-AES) 1. Preparation of Adipic Acid Monohydrazone of Morpholinodaunorubicin The following were combined and stirred at room temperature under Ar while being protected from light for 1 hour: morpholinodaunorubicin acetate salt, dry MeOH, freshly prepared methanolic solution (hydrazidoadipic acid hydrochloride and Et3N and TFA stock solutions). The solvent was removed under reduced pressure and the resulting residue dissolved in NH4OAc:AN and injected into a semiprep HPLC column. The mixture was washed and concentrated under isocratic conditions. The desired product was collected after about 4.5 min and concentrated by C-18 Sep Pak cartridge. The product was eluted, lyophilized, and stored at -20 C. under Ar. The product was obtained as a red solid with an 80% yield and 95% purity. 2. Preparation of N-hydroxysuccimimide Ester of Adipic Acid Monohydrazone of Morpholinodaunorubicin Hydroxysuccinimide in dry THF and DCC in dry THF were added to the adipic acid monohydrazone of morpholinodaunorubicin in dry THF. The clear, red solution was stirred for 24 h at room temperature under Ar. The end of the reaction was determined by analytical HPLC, and the solvent was removed. The glacial solid was then dissolved in buffer solution (N-methylmorpholinium acetate/AN) and filtered through cotton. The product was isolated by RP-HPLC, diluted with two volumes of n-Methylmorpholinium acetate solution and loaded on a Sep-Pak (900 mg). The product was eluted and lyophilized to obtain a powder with 73% yield and 97.4% purity. d. Preparation of M-DNR-Y1-IgG Conjugate M-DNR-LINKER in dry DMF was added to the MAb solution at a molar ratio M-DNR-LINKER/Y1-IgG of 23. The mixture was gently shaken overnight at room temperature under argon, then centrifuged. The supernatant was filtered through SPIN-X tubes (Costar) and shaken with Bio-Beads SM-2 (Biorad) for 1 hour at room temperature. The mixture was allowed to stand for 10 minutes. The supernatant was passed through PD-10 columns (Pharmacia) that had been equilibrated with PBS. The conjugate was eluted with PBS and the protein-containing fractions combined. The purified conjugate was sterilized by SPIN-X filtration. The conjugate solutions were frozen and stored at -70 C. The product conjugate was obtained in 45-50% yield and had the following characteristics: 5% aggregates; 2%-5% absorbed, non-covalently linked M-DNR derivatives; average molecular ratio of drug to antibody is 4. e. Preparation of M-DNR-Y1IgG Conjugate (via Reduction of the S-S Bonds in the Fe Region) Y1-IgG in a buffer composed of NaCl, MES and EDTA was added to cysteamine hydrochloride so...
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