92689-49-1

Basic information

• Product Name: annamycin
• Synonyms: annamycin;(7S,9S)-7-[(2R,3R,4R,5R,6S)-4,5-Dihydroxy-3-iodo-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-8,10-dihydro-7H-tetracene-5,12-dione
• CAS NO: 92689-49-1
• Molecular Formula: C26H25IO11
• Molecular Weight: 640.372
• Mol File: 92689-49-1.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 822.1 °C at 760 mmHg
• Flash Point: 451 °C
• Appearance: /
• Density: 1.94 g/cm³
• Vapor Pressure: 1.31E-28mmHg at 25°C
• Refractive Index: 1.763
• PKA: 7.75±0.60(Predicted)
• CAS DataBase Reference: annamycin(CAS DataBase Reference)
• NIST Chemistry Reference: annamycin(92689-49-1)
• EPA Substance Registry System: annamycin(92689-49-1)

Safety Data

• Hazardous Substances Data: 92689-49-1(Hazardous Substances Data)

Usage

Description

Annamycin is a potent anthracycline antibiotic and antitumor agent derived from the actinomycete strain Streptomyces refuineus var. annamyceticus. It exhibits a unique chemical structure characterized by a tricyclic aglycon system and a disaccharide side chain, which contributes to its biological activity.

Uses

Used in Pharmaceutical Industry:
Annamycin is used as a topoisomerase II inhibitor for its anti-tumor activity. It plays a crucial role in cancer research, particularly in the induction of apoptosis in cancer cells, making it a valuable compound in the development of anticancer therapies.
Used in Cancer Research:
Annamycin is utilized as an apoptosis inducer, targeting and disrupting the activity of topoisomerase II, an enzyme essential for DNA replication. This inhibition leads to the prevention of cancer cell proliferation and the promotion of cell death, offering a potential strategy for combating various types of cancer.

InChI:InChI=1/C26H25IO11/c1-9-19(30)24(35)18(27)25(37-9)38-13-7-26(36,14(29)8-28)6-12-15(13)23(34)17-16(22(12)33)20(31)10-4-2-3-5-11(10)21(17)32/h2-5,9,13,18-19,24-25,28,30,33-36H,6-8H2,1H3/t9-,13-,18+,19-,24-,25-,26-/m0/s1

Upstream product

• 92689-48-0 (7S,9S)-14-O-(tert-butyldimethylsilyl)-4-demethoxy-7-O-(2,6-dideoyxy-2-iodo-α-L-mannopyranosyl)adriamycinone 
• 73983-23-0 Acetic acid (2S,3S,4S,5R,6R)-4-acetoxy-5,6-dihydroxy-2-methyl-tetrahydro-pyran-3-yl ester 
• 65818-86-2 4-demethoxyadriamycinone 
• 81979-75-1 (+/-)-14-bromo-4-demethoxydaunomycinone 
• 92761-44-9 (7S,9S)-14-O-(tert-butyldimethylsilyl)-4-demethoxy-7-O-(3,4-di-O-acetyl-2,6-dideoxy-2-iodo-α-L-mannopyranosyl)adriamycinone 
• 92689-46-8 14-O-(tert-butyldimethylsilyl)-4-demethoxyadriamycinone 

Relevant articles and documents

Synthesis of 4-demethoxyadriamycinone utilizing ruthenium-catalyzed oxidation of allyl acetates

A new method for the construction of the side chain of anti-cancer drugs adriamycins is demonstrated by the synthesis of 4-demethoxyadriamycinone. The key step is the ruthenium-catalyzed oxidation of allyl acetates to the corresponding α-hydroxyketones.