58286-56-9

Basic information

• Product Name: Nanaomycin A methyl ester
• Synonyms: (1S,3R)-3,4-Dihydro-3β-(methoxycarbonylmethyl)9-hydroxy-1α-methyl-1H-naphtho[2,3-c]pyran-5,10-dione;Nanaomycin A methyl ester;OM173-alphaA
• CAS NO: 58286-56-9
• Molecular Formula: C₁₇H₁₆O₆
• Molecular Weight: 316.30534
• Mol File: 58286-56-9.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Nanaomycin A methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Nanaomycin A methyl ester(58286-56-9)
• EPA Substance Registry System: Nanaomycin A methyl ester(58286-56-9)

Safety Data

• Hazardous Substances Data: 58286-56-9(Hazardous Substances Data)

Usage

Description

Nanaomycin A methyl ester is a bioactive compound that functions as a selective inhibitor of the DNA methyltransferase 3B (Dnmt3b) enzyme. It exhibits antibiotic, antimycoplasmic, and antifungal properties, making it a versatile molecule with potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
Nanaomycin A methyl ester is used as a therapeutic agent for its antibiotic, antimycoplasmic, and antifungal properties, targeting a wide range of pathogens and contributing to the treatment and prevention of infections.
Used in Epigenetic Research:
As a selective Dnmt3b inhibitor, Nanaomycin A methyl ester is utilized in epigenetic research to study the role of DNA methylation in various biological processes, including gene regulation, cellular differentiation, and disease development.
Used in Drug Development:
Nanaomycin A methyl ester serves as a lead compound in drug development for the creation of novel therapeutics targeting the Dnmt3b enzyme. Its potential applications include the treatment of cancer, neurological disorders, and other conditions influenced by epigenetic mechanisms.

Upstream product

• 78340-69-9 trans-methyl <9-methoxy-1-methyl-5,10-dioxo-3,4,5,10-tetrahydro-1H-naphtho<2,3-c>pyran-3-yl>acetate 
• 78340-68-8 cis-methyl <9-methoxy-1-methyl-5,10-dioxo-3,4,5,10-tetrahydro-1H-naphtho<2,3-c>pyran-3-yl>acetate 
• 1515-76-0 1-acetoxy-1,3-butadiene 
• 1246659-64-2 (+)-methyl 2-[(1S,3R)-5,8-dioxo-1-methyl-3,4-dihydro-1H-benzopyran-3-yl]acetate 
• 124287-42-9 methyl (4-acetyl-2,3-dihydro-5-hydroxybenzofuran-2-yl)acetate 
• 78284-27-2 methyl trans-5,9,10-trimethoxy-1-methyl-3,4-dihydro-1H-naphtho<2,3-c>pyran-3-ylacetate 
• 78311-26-9 3-(3-bromo-1,4,5-trimethoxy-2-naphthyl)propanoic acid 
• 78284-25-0 3-acetyl-2-formylmethyl-1,4,5-trimethoxynaphthalene 
• 78284-32-9 5,9,10-trimethoxy-1-methyl-3,4-dihydro-1H-naphtho<2,3-c>pyran-3-ol 
• 78284-23-8 3-bromo-5-methoxy-2-(2-methoxycarbonylethyl)-1,4-naphthoquinone 
• 78284-31-8 3-(1'-hydroxyethyl)-1,4,5-trimethoxy-2-(prop-2'-enyl)naphthalene 
• 78284-22-7 2,3-dihydro-4,8,9-trimethoxy-1H-benz[f]inden-1-one 
• 78284-24-9 4,5,9-trimethoxy-3-methylbenzindene 
• 78284-30-7 2-allyl-3-bromo-1,4,5-trimethoxynaphthalene 

Downstream Products

• 107222-54-8 9-Benzyloxy-3,4-dihydro-5,10-dimethoxy-1-methyl-1H-naphtho<2,3-c>pyran-3-essigsaeure-methylester 
• 107222-55-9 9-Benzyloxy-3,4-dihydro-5,10-dimethoxy-1-methyl-1H-naphtho<2,3-c>pyran-3-essigsaeure 

Relevant articles and documents

Intra- And intermolecular oxa-pictet-spengler cyclization strategy for the enantioselective synthesis of deoxy analogues of (+)-nanomycin A methyl ester, (+)-eleutherin, (+)-allo-eleutherin, and (+)-thysanone

Enantioselective synthesis of deoxy analogues of pyranonaphthoquinone antibiotics (+)-nanomycin A methyl ester, (+)eleutherin, (+)-allo-eleutherin, and (+)-thysanone was achieved in good overall yield with high enantio- and diastereoselectivity from the common intermediate (R)-3-(2,5-dimethoxyph.enyl) propane-1,2-diol. The intramolecular oxaPictet-Spengler cyclization of 6-a:ryl-l.,3-dioxolone was de-veloped for the first time and utilized in the enantioselective synthesis of (H-)-deoxynanomycin A methyl ester, whereas the intermolecular oxa-Pictet-Spengler cycllzation strategy was applied to the enantioselective synthesis of deoxy analogues of (+)-eleutherm, (+)-allo-eleutherin, and. (+)-thysanone,

A versatile intermediate for the synthesis of pyranoquinone antibiotics

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Allylation of 2-Alkanoyl 1,4-Quinones with Allylsilanes and Allylstannanes. Efficient Synthesis of Pyranonaphthoquinone Antibiotics

Total syntheses of pyranonaphthoquinone antibiotics eleutherin, isoeleutherin, nanaomycin A, and deoxyfrenolicin are described.The crucial step in the route is a regioselective allylation of alkanoyl quinones with allylsilanes and allylstannanes.The allyl