CAS 120243-02-9

N,N′-[(1S)-1-(Hydroxymethyl)-1,5-pentanediyl]bis[2,3-dihydroxybenzamide]

Description:

N,N′-[(1S)-1-(Hydroxymethyl)-1,5-pentanediyl]bis[2,3-dihydroxybenzamide], with the CAS number 120243-02-9, is a chemical compound characterized by its dual amide functional groups and a hydroxymethyl-substituted pentanediyl linker. This compound features two 2,3-dihydroxybenzamide moieties, which contribute to its potential biological activity, particularly in interactions with biological targets due to the presence of hydroxyl groups that can participate in hydrogen bonding. The stereochemistry indicated by the (1S) configuration suggests specific spatial arrangements that may influence its reactivity and interactions. The presence of multiple hydroxyl groups enhances its solubility in polar solvents and may also affect its pharmacokinetic properties. This compound may be of interest in medicinal chemistry and biochemistry for its potential applications in drug development or as a biochemical probe, although specific biological activities and applications would require further investigation through empirical studies.

Formula: C₂₀H₂₄N₂O₇

InChI: InChI=1S/C20H24N2O7/c23-11-12(22-20(29)14-7-4-9-16(25)18(14)27)5-1-2-10-21-19(28)13-6-3-8-15(24)17(13)26/h3-4,6-9,12,23-27H,1-2,5,10-11H2,(H,21,28)(H,22,29)/t12-/m0/s1

InChI key: InChIKey=WNBVGSNESTZACV-LBPRGKRZSA-N

SMILES: C(N[C@@H](CCCCNC(=O)C1=C(O)C(O)=CC=C1)CO)(=O)C2=C(O)C(O)=CC=C2

Synonyms:

• (S)-(-)-Myxochelin A
• Benzamide, N,N'-(1-(hydroxymethyl)-1,5-pentanediyl)bis(2,3-dihydroxy-
• Benzamide, N,N′-[(1S)-1-(hydroxymethyl)-1,5-pentanediyl]bis[2,3-dihydroxy-
• Myxochelin
• N,N'-(6-hydroxyhexane-1,5-diyl)bis(2,3-dihydroxybenzamide)
• N,N'-Bis(2,3-dihydroxybenzoyl)lysinol
• N,N′-[(1S)-1-(Hydroxymethyl)-1,5-pentanediyl]bis[2,3-dihydroxybenzamide]
• Myxochelin A

Myxochelin A

CAS: 120243-02-9

Myxochelin A from A. disciformis fights Gram-positive bacteria, inhibits 5-LO with IC50 of 1.9 μM, and is cytotoxic to colon cancer cells.

Formula: C₂₀H₂₄N₂O₇

Color and Shape: Solid

Molecular weight: 404.419

Ref: TM-T35692

Myxochelin A

CAS: 120243-02-9

Ref: 7W-GW8199

Myxochelin A

Controlled Product

CAS: 120243-02-9

Applications Myxochelin A is a potent inhibitor of human 5-lipoxygenase (5-LO). Studies show that Myxochelin A is a natural product that may possess potent antitumor activity at non-cytotoxic concentrations.
References Schieferdecker, S., et al.: Tetrahedron Lett., 57, 1359 (2016); Korp, J., et al.: ChemBioChem., 16, 2445 (2015); Schieferdecker, S., et al.: J. Nat. Prod., 78, 335 (2015)

Formula: C₂₀H₂₄N₂O₇

Color and Shape: Neat

Molecular weight: 404.414

Ref: TR-M900000

Myxochelin A

CAS: 120243-02-9

Myxochelin A is an iron-chelating siderophore, which is a specialized secondary metabolite produced by certain strains of myxobacteria. These microorganisms, often found in soil and decomposing material, synthesize Myxochelin A to scavenge iron from the environment, essential for their survival and growth. The mode of action of Myxochelin A involves the sequestration of ferric iron (Fe^3+) ions through its high-affinity binding sites. This effectively deprives competing microorganisms of the iron required for crucial biological processes, imparting an antimicrobial effect.

Formula: C₂₀H₂₄N₂O₇

Purity: Min. 95%

Molecular weight: 404.4 g/mol

Ref: 3D-VEA24302