4-Methylaeruginoic acid
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| Category | Antibiotics |
| Catalog number | BBF-01926 |
| CAS | |
| Molecular Weight | 237.28 |
| Molecular Formula | C11H11NO3S |
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Description
4-Methylaeruginoic acid is an antibiotic produced by Str. sp. KCTC9303. It has an effect on the cytotoxicity of several human tumor cell lines.
Specification
| Synonyms | (4S)-2-(2-hydroxyphenyl)-4-methyl-4,5-dihydro-1,3-thiazole-4-carboxylic acid; (S)-Desazadesferrithiocin |
| IUPAC Name | (4S)-2-(2-hydroxyphenyl)-4-methyl-5H-1,3-thiazole-4-carboxylic acid |
| Canonical SMILES | CC1(CSC(=N1)C2=CC=CC=C2O)C(=O)O |
| InChI | InChI=1S/C11H11NO3S/c1-11(10(14)15)6-16-9(12-11)7-4-2-3-5-8(7)13/h2-5,13H,6H2,1H3,(H,14,15)/t11-/m1/s1 |
| InChI Key | OXCVIPGXPILNPT-LLVKDONJSA-N |
Properties
| Appearance | Yellow Powder |
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Boiling Point | 450.8±55.0°C at 760 mmHg |
| Density | 1.4±0.1 g/cm3 |
Reference Reading
1. Effects of C-4 stereochemistry and C-4' hydroxylation on the iron clearing efficiency and toxicity of desferrithiocin analogues
R J Bergeron, J Wiegand, J S McManis, B H McCosar, W R Weimar, G M Brittenham, R E Smith J Med Chem. 1999 Jul 1;42(13):2432-40. doi: 10.1021/jm990058s.
Additional structure-activity studies of desferrithiocin analogues are carried out. The effects of stereochemistry at C-4 on the ligands' iron clearing efficiency are reviewed and assessed using the enantiomers 4,5-dihydro-2-(2, 4-dihydroxyphenyl)thiazole-4(R)-carboxylic acid and 4,5-dihydro-2-(2, 4-dihydroxyphenyl)thiazole-4(S)-carboxylic acid. The utility of 4'-hydroxylation as a method of reducing the toxicity of desazadesferrithiocin analogues is also examined further with the synthesis and in vivo comparison of 4, 5-dihydro-2-(2-hydroxyphenyl)-4-methylthiazole-4(S)-carboxylic acid, which is the natural product 4-methylaeruginoic acid, and 4, 5-dihydro-2-(2,4-dihydroxyphenyl)-4-methylthiazole-4(S)-carboxylic acid. The stereochemistry at C-4 is shown to have a substantial effect on the iron clearing efficiency of desferrithiocin analogues, as does C-4'-hydroxylation on the toxicity profile. All of the compounds are evaluated in a bile-duct-cannulated rodent model to determine iron clearance efficiency and are carried forward to the iron-overloaded primate for iron clearing measurements. On the basis of the results of the present work, although 4,5-dihydro-2-(2, 4-dihydroxyphenyl)thiazole-4(S)-carboxylic acid is still the most promising candidate for clinical evaluation, 4,5-dihydro-2-(2, 4-dihydroxyphenyl)-4-methylthiazole-4(S)-carboxylic acid (4'-hydroxydesazadesferrithiocin) also merits further preclinical assessment.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
