5-[(3S,5R,10S,13R,14S,17R)-3,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one

Base Information

• Chemical Name: 5-[(3S,5R,10S,13R,14S,17R)-3,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one
• CAS No.: 465-21-4
• Molecular Formula: C24H34O4
• Molecular Weight: 386.532
• Hs Code.: 29322090
• European Community (EC) Number: 621-198-0
• Wikipedia: Bufalin
• Mol file: 465-21-4.mol

Synonyms:NSC 89595;465-21-4;BRN 5141601;5beta-Bufa-20,22-dienolide, 3beta,14-dihydroxy-;(3beta,5beta)-3,14-dihydroxybufa-20,22-dienolide;(3-beta,5-beta)-3,14-Dihydroxybufa-20,22-dienolide;5-beta-BUFA-20,22-DIENOLIDE, 3-beta,14-DIHYDROXY-;Bufa-20,22-dienolide, 3,14-dihydroxy-, (3beta,5beta)-;Bufa-20,22-dienolide, 3,14-dihydroxy-, (3-beta,5-beta)-;SCHEMBL14007456;AKOS015896786;5-[(3S,5R,10S,13R,14S,17R)-3,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one;LS-45286;5beta,20(22)-Bufadienolide-3beta,14-diol

Chemical Property of 5-[(3S,5R,10S,13R,14S,17R)-3,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one

Chemical Property:

• Appearance/Colour: White solid.
• Vapor Pressure: 1.05E-14mmHg at 25°C
• Melting Point: 242 - 243oC
• Refractive Index: 1.593
• Boiling Point: 556.6 °C at 760 mmHg
• PKA: 15.01±0.70(Predicted)
• Flash Point: 189 °C
• PSA: 70.67000
• Density: 1.226 g/cm³
• LogP: 4.24190
• Storage Temp.: 2-8°C
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 386.24570956
• Heavy Atom Count: 28
• Complexity: 741

Purity/Quality:

99% ^*data from raw suppliers

Bufalin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 28
• Safety Statements: 28-36/37-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC12CCC(CC1CCC3C2CCC4(C3(CCC4C5=COC(=O)C=C5)O)C)O
• Isomeric SMILES: C[C@]12CC[C@@H](C[C@H]1CCC3C2CC[C@]4([C@@]3(CC[C@@H]4C5=COC(=O)C=C5)O)C)O
• Uses: A bufadienolide derivative, cardiac steroid, a component of bufadienolides present in the traditional Chinese medicine Chan'su, used therapeutically for the treatment of heart disease, also has been reported as a protective factor in many tumors. Bufalin has been used: to test its effect on invasion and activation of nuclear factor kappa- B (NF-κB) cells and tumor necrosis factor-α (TNF-α) stimulated rheumatoid arthritis fibroblast-like synoviocytes (RAFLSs) as a nuclear receptor coactivator 3 (NCOA3) inhibitor in chondrocytesto test its anti-metastasis effect in lung cancer cells (NCI-H460) resistant to gefitinib

Technology Process of 5-[(3S,5R,10S,13R,14S,17R)-3,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one

There total 35 articles about 5-[(3S,5R,10S,13R,14S,17R)-3,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one 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: 73.0%

C33H55BrO4Si2 → bufalin (465-20-3,465-21-4,33766-62-0,107033-69-2)

Guidance literature:

C₃₃H₅₅BrO₄Si₂; With triethyl borane; oxygen; tri-n-butyl-tin hydride; In hexane; dichloromethane; at 20 ℃; for 4h; under 760.051 Torr;

With hydrogenchloride; water; In methanol; hexane; dichloromethane; at 20 ℃; for 20h; Inert atmosphere;

DOI:10.1021/acs.orglett.0c03251

Reference yield: 70.0%

5-(3'β-benzyloxy-14'-hydroxy-5'β,14'β-androstan-17'β-yl)-2H-pyran-2-one (83911-60-8) → bufalin (465-20-3,465-21-4,33766-62-0,107033-69-2)

Guidance literature:

With palladium dihydroxide;

DOI:10.1139/v82-309

Reference yield:

2-mesitylenesulphonyl chloride (773-64-8) → bufalin (465-20-3,465-21-4,33766-62-0,107033-69-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) Et₃N; 2.) DBN / 1.) CH₂Cl₂, in ice-bath, 30 min; 2.) benzene, reflux, 1 h

2: 1.) NBS, 1percent HClO₄; 2.) AcONa / 2.) Raney-Ni / 1.) acetone, H₂O, r. t., 30 min; 2.) MeOH, CH₂Cl₂, 30 min

3: 70 percent / H₂ / Pd(OH)2/C / benzene; ethanol; cyclohexane / 2 h / Heating

With N-Bromosuccinimide; perchloric acid; 2,6-dichloro-benzonitrile; hydrogen; sodium acetate; triethylamine; palladium dihydroxide; nickel; In ethanol; cyclohexane; benzene;

DOI:10.1002/hlca.19830660831

upstream raw materials:

(+)-digitoxigenin

5-(3'β-benzyloxy-14'-hydroxy-5'β,14'β-androstan-17'β-yl)-2H-pyran-2-one

2-mesitylenesulphonyl chloride

5-(3'β-benzyloxy-5'β-androst-14'-en-17'β-yl)-3,6-dihydro-2H-pyran-2,3-diol

Downstream raw materials:

(3β,5β)-3-(acetyloxy)-14-hydroxy-bufa-20,22-dienolide

14-hydroxy-3β-(4-nitro-benzoyloxy)-5β,14β-bufa-20,22-dienolide

3β-hydroxy-21-nor-5β-pregnen-(14)-oic acid-(20)

12β-hydroxybufalin

Refernces

• 1、 Wiesner,Tsai,Sen,et al.. "On cardioactive steroids. XII. The synthesis of (natural) bufalin and α'-isobufalin". . p. 2632 - 2640. Retrieved 2007/10/02.