Aplysiatoxin, 17-debromo-

Base Information

• Chemical Name: Aplysiatoxin, 17-debromo-
• CAS No.: 52423-28-6
• Molecular Formula: C32H48 O10
• Molecular Weight: 592.727
• NSC Number: 271679
• Wikipedia: Debromoaplysiatoxin
• Wikidata: Q104887546
• Mol file: 52423-28-6.mol

Synonyms:debromoaplysiatoxin

Chemical Property of Aplysiatoxin, 17-debromo-

Chemical Property:

• Vapor Pressure: 2.02E-24mmHg at 25°C
• Boiling Point: 762.2°Cat760mmHg
• Flash Point: 239°C
• PSA: 140.98000
• Density: 1.24g/cm³
• LogP: 4.38670
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 7
• Exact Mass: 592.32474772
• Heavy Atom Count: 42
• Complexity: 956

Purity/Quality:

99% ^*data from raw suppliers

DEBROMOAPLYSIATOXIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC(C23CC(C(C(O2)C(C)CCC(C4=CC(=CC=C4)O)OC)C)OC(=O)CC(OC(=O)CC1(O3)O)C(C)O)(C)C
• General Description: Debromoaplysiatoxin (DAT) is a bioactive compound derived from marine sources, known for its interaction with protein kinase C (PKC) and its potential anti-proliferative effects against cancer cells. Simplified analogs of DAT, such as 10-methyl-aplog-1 and its derivatives, have been explored to improve potency and reduce toxicity, with studies highlighting the role of CH/π interactions in enhancing binding affinity to the PKC δ-C1B domain. However, further optimization is required to maximize therapeutic efficacy.

Technology Process of Aplysiatoxin, 17-debromo-

There total 1 articles about Aplysiatoxin, 17-debromo- 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: 61.0%

(1S,3R,4S,5S,9R,13S,14R)-9-((R)-1-Benzyloxymethoxy-ethyl)-3-[(1S,4S)-4-(3-benzyloxymethoxy-phenyl)-4-methoxy-1-methyl-butyl]-13-hydroxy-4,14,16,16-tetramethyl-2,6,10,17-tetraoxa-tricyclo[11.3.1.11,5]octadecane-7,11-dione → debromo aplysiatoxin (52423-28-6)

Guidance literature:

With hydrogen; triethylamine; palladium on activated charcoal; In ethanol; Ambient temperature;

DOI:10.1021/ja00254a062

Reference yield: 42.0%

debromo aplysiatoxin (52423-28-6) → C31H46O9 (1446754-13-7)

Guidance literature:

With 20% palladium hydroxide-activated charcoal; hydrogen; In ethyl acetate; at 20 ℃; for 2.83333h;

DOI:10.1016/j.bmcl.2013.05.096

Reference yield: 18.0%

debromo aplysiatoxin (52423-28-6) → C31H44O8

Guidance literature:

With 20% palladium hydroxide-activated charcoal; hydrogen; In ethyl acetate; at 20 ℃; for 2.83333h;

DOI:10.1016/j.bmcl.2013.05.096

Downstream raw materials:

monomethylether of debromoaplysiatoxin

debromoaplysiatoxin 20-acetate

debromoaplysiatoxin 20,30-diacetate

anhydrodebromoaplysiatoxin

Refernces

Synthesis and biological activities of simplified aplysiatoxin analogs focused on the CH/π interaction

10.1016/j.bmcl.2020.127657

The research focused on synthesizing and evaluating simplified analogs of debromoaplysiatoxin (DAT) to enhance their anti-proliferative activity against cancer cells while minimizing adverse effects. The study synthesized a new derivative, 10-methyl-aplog-1 (1), and its analog 2, which features a naphthalene ring to improve CH/π interactions with the protein kinase C (PKC) δ-C1B domain. The synthesis involved multiple chemicals, including 6-hydroxy-1-naphthoic acid, diethyl malonate, and various protecting groups such as benzyl and triethylsilyl ethers. The results indicated that while the anti-proliferative activity of compound 2 was more potent than that of 1, its binding affinity to the PKC δ-C1B domain did not exceed that of 1, suggesting that further structural optimization is needed to enhance the interactions and therapeutic potential of these compounds.

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