Aclacinomycin A (Aclarubicin)

Base Information

• Chemical Name: Aclacinomycin A (Aclarubicin)
• CAS No.: 57576-44-0
• Molecular Formula: C42H53NO15
• Molecular Weight: 811.881
• European Community (EC) Number: 260-824-3
• Wikipedia: Aclarubicin
• Mol file: 57576-44-0.mol

Synonyms:Aclacinomycin A (Aclarubicin);57576-44-0;methyl (1R,2R,4S)-4-[(2R,4S,5S,6S)-4-(dimethylamino)-5-[(2S,4S,6S)-4-hydroxy-6-methyl-5-[(2R,6S)-6-methyl-5-oxooxan-2-yl]oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxy-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-3,4-dihydro-1H-tetracene-1-carboxylate;AKOS030254907

Chemical Property of Aclacinomycin A (Aclarubicin)

Chemical Property:

• Vapor Pressure: 1.17E-34mmHg at 25°C
• Melting Point: 151-153 °C
• Refractive Index: 1.629
• Boiling Point: 897.676 °C at 760 mmHg
• PKA: 6.41±0.70(Predicted)
• Flash Point: 496.696 °C
• PSA: 217.05000
• Density: 1.42 g/cm³
• LogP: 3.15770
• Storage Temp.: 2-8°C
• Solubility.: Dichloromethane (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 10
• Exact Mass: 811.34151998
• Heavy Atom Count: 58
• Complexity: 1530

Purity/Quality:

98%,99%, ^*data from raw suppliers

Aclacinomycin A ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1(CC(C2=C(C3=C(C=C2C1C(=O)OC)C(=O)C4=C(C3=O)C(=CC=C4)O)O)OC5CC(C(C(O5)C)OC6CC(C(C(O6)C)OC7CCC(=O)C(O7)C)O)N(C)C)O
• Isomeric SMILES: CC[C@]1(C[C@@H](C2=C(C3=C(C=C2[C@H]1C(=O)OC)C(=O)C4=C(C3=O)C(=CC=C4)O)O)O[C@H]5C[C@@H]([C@@H]([C@@H](O5)C)O[C@H]6C[C@@H](C([C@@H](O6)C)O[C@H]7CCC(=O)[C@@H](O7)C)O)N(C)C)O
• Uses: Aclarubicin is an anthracycline antibiotic. It is used in the treatment of cancer. Antineoplastic.
• Therapeutic Function: Antitumor, Antibiotic

Technology Process of Aclacinomycin A (Aclarubicin)

There total 1 articles about Aclacinomycin A (Aclarubicin) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(+)-aklavinone (16234-96-1) → aclacinomycin A (57576-44-0) + aclacinomycin X

Guidance literature:

With soybean meal; dipotassium hydrogenphosphate; D-glucose; KE₃₀₃ of S_. galilaeus MA₁₄₄-M₁; magnesium sulfate; copper(II) sulfate; iron(II) sulfate; zinc(II) sulfate; sodium chloride; manganese(ll) chloride; starch; yeast extract; In water; at 28 ℃; for 96h;

DOI:10.7164/antibiotics.49.669

Reference yield: 100.0%

aclacinomycin A (57576-44-0) → (+)-aklavinone (16234-96-1)

Guidance literature:

With hydrogenchloride; In water; at 90 ℃;

DOI:10.1021/acs.jmedchem.0c01191

Reference yield:

aclacinomycin A (57576-44-0) → 3',3'-didesmethyl-aclarubicin (77607-10-4)

Guidance literature:

Multi-step reaction with 4 steps

1: hydrogenchloride / water / 90 °C

2: (triphenylphosphine)gold(I) chloride; silver(I) triflimide / dichloromethane / 0.5 h / -20 °C / Molecular sieve

3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; aq. phosphate buffer / 1.5 h / 0 °C / pH 7

4: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / dichloromethane / 0.25 h / Inert atmosphere

With hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,3-dimethylbarbituric acid; (triphenylphosphine)gold(I) chloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; silver(I) triflimide; In aq. phosphate buffer; dichloromethane; water;

DOI:10.1021/acs.jmedchem.0c01191

upstream raw materials:

(+)-aklavinone

Downstream raw materials:

3,5,5-trimethyl-2-oxomorpholine

5,6-dihydro-3,5,5-trimethyl-1,4-oxazin-2-one

methyl 9(R,S)-ethyl-4,6,9(R,S)-trihydroxy-5,12-dioxo-7,8,9,10-tetrahydronaphthacene-10(R,S)-carboxylate

bi(7-deoxyaklavinon-7-yl)

Refernces