14-Bromodaunorubicin

Base Information

• Chemical Name: 14-Bromodaunorubicin
• CAS No.: 65026-79-1
• Molecular Formula: C27H28 Br N O10
• Molecular Weight: 606.42
• DSSTox Substance ID: DTXSID20215356
• Wikidata: Q83091382
• Mol file: 65026-79-1.mol

Synonyms:14-bromodaunorubicin;14-bromodaunorubicin hydrobromide;14-bromodaunorubicin hydrochloride;14-bromodaunorubicin, (L-arabino)-isomer, 2-(14)C-labeled;14-bromodaunorubicin, 2-(14)C-labeled

Chemical Property of 14-Bromodaunorubicin

Chemical Property:

• Vapor Pressure: 1.08E-27mmHg at 25°C
• Boiling Point: 809.6°C at 760 mmHg
• PKA: 7.34±0.60(Predicted)
• Flash Point: 443.4°C
• PSA: 185.84000
• Density: 1.72g/cm³
• LogP: 2.10420
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 5
• Exact Mass: 605.08966
• Heavy Atom Count: 39
• Complexity: 982

Purity/Quality:

99% ^*data from raw suppliers

14-BROMODAUNORUBICIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CBr)O)N)O
• Isomeric SMILES: C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CBr)O)N)O

Technology Process of 14-Bromodaunorubicin

There total 3 articles about 14-Bromodaunorubicin 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: 88.0%

daunomycin hydrochloride (23541-50-6) → 14-bromodaunorubicin (65026-79-1)

Guidance literature:

With bromine; In 1,4-dioxane; methanol; chloroform; for 2h; Ambient temperature;

DOI:10.1021/jm00147a017

Reference yield:

daunomycin hydrochloride (23541-50-6) → 14-chlorodaunorubicine hydrobromide (121250-06-4) + 14-bromodaunorubicin (65026-79-1)

Guidance literature:

daunomycin hydrochloride; With bromine; trimethyl orthoformate; In 1,4-dioxane; methanol; at 11 ℃; for 2h; Inert atmosphere;

With methyloxirane; In 1,4-dioxane; methanol; at 4 ℃; for 1.25h; Inert atmosphere;

With hydrogen bromide; In 1,4-dioxane; methanol; acetone; at 20 ℃; for 48h; Inert atmosphere;

Reference yield:

14-bromo-13-dimethylketal-daunorubicin (106401-68-7) → 14-bromodaunorubicin (65026-79-1)

Guidance literature:

With hydrogen bromide; In water; acetone; at 15 - 20 ℃; for 6h; pH=3;

upstream raw materials:

daunomycin hydrochloride

14-bromo-13-dimethylketal-daunorubicin

Downstream raw materials:

C₅₇H₆₂N₂O₂₀S₂

adriamycin 14-thiobenzoate

14-n-butyl-14-thiaadriamycin

14-n-pentyl-14-thiaadriamycin

Refernces

Adriamycin analogues. Preparation and biological evaluation of some thio ester analogues of adriamycin and N-(trifluoroacetyl)adriamycin 14-valerate

10.1021/jm00157a025

The study investigates the preparation and biological evaluation of thio ester analogues of the antitumor antibiotic adriamycin and its derivative N-(trifluoroacetyl)adriamycin. The researchers synthesized a series of N-(trifluoroacetyl)adriamycin 14-thio esters (compounds 3a-e) and adriamycin 14-thio esters (compounds 4a-e) using reactions with various thio acids and N-(trifluoroacetyl)-14-bromodaunorubicin or 14-bromodaunorubicin, respectively. These compounds were evaluated for their in vitro growth-inhibitory activity against human leukemic cells, in vivo antitumor activity in a murine P388 leukemia model, and the rate of thio ester deacylation by esterases in mouse serum. The study found that while the adriamycin thio esters (4a-e) exhibited significant in vivo antitumor activity and interacted with DNA similarly to adriamycin, none of the N-(trifluoroacetyl)adriamycin thio esters (3a-e) showed biological activity. The results suggest that the presence of a sulfur function in the thio ester structure significantly affects the biological activity and metabolic stability of these compounds.

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