5690-03-9

Usage

Uses

Used in Anti-inflammatory Applications:
Splitomicin is used as an anti-inflammatory agent for its ability to selectively and potently inhibit the Sir2 protein, which in turn produces an inhibitory effect on neutrophils. This property makes it a valuable compound in the development of treatments for various inflammatory conditions.
Used in Cancer Research:
In the field of cancer research, Splitomicin is used as a selective and potent inhibitor of Sir2 for its potential to sensitize mammalian cells to a variety of DNA-damaging agents by abrogating Sir2p activity on p53. This characteristic makes it a promising candidate for the development of novel cancer therapeutics, particularly in combination with conventional DNA-damaging agents to enhance their efficacy.
Used in Drug Delivery Systems:
To improve the delivery, bioavailability, and therapeutic outcomes of Splitomicin, researchers are exploring the development of novel drug delivery systems. These systems may involve the use of various organic and metallic nanoparticles as carriers for Splitomicin, aiming to enhance its overall effectiveness in targeting cancer cells and reducing inflammation.

Synthesis Reference(s)

Journal of the American Chemical Society, 69, p. 2341, 1947 DOI: 10.1021/ja01202a027

Biological Activity

Inhibitor of Sir2p (IC 50 = 60 μ M), an NAD + -dependent Sir2 family deacetylase required for chromatin-dependent silencing in yeast.

Biochem/physiol Actions

Cell permeable: yes

InChI:InChI=1/C13H10O2/c14-13-8-6-11-10-4-2-1-3-9(10)5-7-12(11)15-13/h1-5,7H,6,8H2

Upstream product

• 10441-53-9 3-(2-hydroxynaphthalen-1-yl)propanoic acid 
• 107-13-1 acrylonitrile 
• 135-19-3 β-naphthol 
• 79-10-7 acrylic acid 
• 14233-73-9 3-(2-hydroxynaphthalen-1-yl)propanenitrile 
• 14103-18-5 ethyl 3-oxo-2,3-dihydro-1H-benzo[f]chromene-2-carboxylate 
• 4352-89-0 3H-benzo[f]chromen-3-one 

Downstream Products

• 34225-11-1 3-(2-methoxynaphthalen-1-yl)propanoic acid 
• 10441-53-9 3-(2-hydroxynaphthalen-1-yl)propanoic acid 
• 1262309-20-5 C₂₂H₂₄O₄ 
• 1360652-03-4 (R)-1-phenyl-1H-benzo[f]chromen-3(2H)-one 
• 1232144-29-4 1-phenyl-1,2-dihydro-3H-benzo[f]chromen-3-one 
• 5448-11-3 NSC 17364 
• 1360546-18-4 (E)-ethyl 3-(1-(3-(dibenzylamino)-3-thioxopropyl)naphthalen-2-yl)acrylate 
• 1360546-28-6 ethyl 2-((2R,3S)-2-(dibenzylcarbamothioyl)-2,3-dihydro-1H-cyclopenta[a]naphthalen-3-yl)acetate 

Relevant academic research and scientific papers

Organocatalyst-Mediated Dynamic Kinetic Enantioselective Acylation of 2-Chromanols

We recently developed a novel chiral catalyst-directed dynamic kinetic diastereoselective acylation of hemiacetals for the synthesis of carbohydrates. In this update, we describe a catalytic method for the dynamic kinetic enantioselective acylation of 2-c

Chiral Hypervalent Organoiodine-Catalyzed Enantioselective Oxidative Spirolactonization of Naphthol Derivatives

Highly enantioselective oxidative dearomatization of 2-naphthol derivatives was achieved for the first time by using conformationally flexible organoiodine catalysts derived from 2-aminoalcohol as a chiral source. Moreover, with the use of these catalysts

IODOARENE DERIVATIVE, METHOD FOR PRODUCING OPTICALLY ACTIVE SPIROLACTONE COMPOUND USING SAME, AND METHOD FOR PRODUCING OPTICALLY ACTIVE CYCLIZATION ADDUCT

An optically active spirolactone compound is highly enantioselectively produced by using an iodoarene derivative which can be synthesized easily and which is not racemized easily. [Solution] A hypervalent iodine compound precursor (iodoarene derivative) w

Catalytic asymmetric conjugate addition/oxidative dearomatization towards multifunctional spirocyclic compounds

Naphthol compounds bearing a pendant α,β-unsaturated ester undergo a copper(I)-catalyzed asymmetric conjugate addition/copper(II)-mediated intramolecular oxidative coupling to afford benzofused spirocyclic cyclohexenones (see scheme). This one-pot strategy results in two new carbon-carbon bonds and three contiguous stereocenters. The products contain a high degree of functionality and molecular complexity.

Anionic alternating copolymerization of epoxide and six-membered lactone bearing naphthyl moiety

This article describes the anionic copolymerization of glycidyl phenyl ether (GPE) and 1,2-dihydro-3H-naphtho[2,1-b]pyran-3-one (DHNP), a six-membered aromatic lactone bearing naphthyl moiety. The copolymerization proceeded in a 1:1 alternating manner, to

Methods for inhibiting deacetylase activity

A method for identifying a compound that inhibits the NAD+-dependent deacetylase activity of a SIR2 protein is disclosed. These compounds are useful for the treatment of cancers and other diseases, through the activation of silenced genes, through the promotion of apoptosis in cancerous cells, and through the inhibition of transcriptional repressor activity in oncogenes.

Direct functionalization of arenes by primary alcohol sulfonate esters catalyzed by gold(III)

Alkylation of arenes by primary alcohol triflate or methanesulfonate esters can be efficiently catalyzed by AuCl3 with silver triflate. Copyright

Inhibitors of Sir2: Evaluation of Splitomicin Analogues

Splitomicin (1) and 41 analogues were prepared and evaluated in cell-based Sir2 inhibition and toxicity assays and an in vitro Sir2 inhibition assay. Lactone ring or naphthalene (positions 7-9) substituents decrease activity, but other naphthalene substitutions (positions 5 and 6) are well-tolerated. The hydrolytically unstable aromatic lactone is important for activity. Lactone hydrolysis rates were used as a measure of reactivity; hydrolysis rates correlate with inhibitory activity. The most potent Sir2 inhibitors were structurally similar to and had hydrolysis rates similar to 1.

A Facile Synthesis of Dihydronaphthopyrans

Efficient and specific syntheses of naturally occurring linear dihydronaphthopyran (6a) and its angular analogues (3b and 4), from appropriate ortho-methoxynaphthaldehydes, have been described.

A facile synthesis of dihydronaphthopyrans

Efficient syntheses of the naturally occurring linear dihydronaphthopyran (6a) and its angular analogues (3b and 4), from the appropriate ortho-methoxynaphthaldehydes, are described.