Cinatrin C1
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00338 |
| CAS | 136266-35-8 |
| Molecular Weight | 374.42 |
| Molecular Formula | C18H30O8 |
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Description
It is produced by the strain of Circinotrichum falcatisporum RF-641. Cinatrin C1 has the activity of inhibiting phosphoesterase A2.
Specification
| Synonyms | 2,3-Furandicarboxylic acid, 2-dodecyltetrahydro-3,4-dihydroxy-5-oxo-, (2S-(2alpha,3alpha,4beta))- |
| IUPAC Name | (2S,3R,4R)-2-dodecoxycarbonyl-4-hydroxy-5-oxooxolane-3-carboperoxoic acid |
| Canonical SMILES | CCCCCCCCCCCCOC(=O)C1C(C(C(=O)O1)O)C(=O)OO |
| InChI | InChI=1S/C18H30O8/c1-2-3-4-5-6-7-8-9-10-11-12-24-18(22)15-13(16(20)26-23)14(19)17(21)25-15/h13-15,19,23H,2-12H2,1H3/t13-,14-,15+/m1/s1 |
| InChI Key | YYAODTFONAOLHT-KFWWJZLASA-N |
Properties
| Appearance | Colorless Powder |
| Melting Point | 162-164 °C |
Reference Reading
1. Total synthesis of (-)-cinatrin C1 based on an In(OTf)3-catalyzed Conia-Ene reaction
Fumiya Urabe, Shunsuke Nagashima, Keisuke Takahashi, Jun Ishihara, Susumi Hatakeyama J Org Chem. 2013 Apr 19;78(8):3847-57. doi: 10.1021/jo400263w. Epub 2013 Apr 11.
The stereocontrolled total synthesis of (-)-cinatrin C1, a phospholipase A2 inhibitor, has been accomplished. The key feature includes the stereoselective construction of the highly substituted tetrahydrofuran core by In(OTf)3-catalyzed Conia-ene reaction of the oxygen-tethered acetylenic malonic ester followed by dihydroxylation with concomitant lactonization.
2. Cinatrins, a novel family of phospholipase A2 inhibitors. II. Biological activities
K Tanaka, H Itazaki, T Yoshida J Antibiot (Tokyo). 1992 Jan;45(1):50-5. doi: 10.7164/antibiotics.45.50.
Cinatrins A, B and C3 inhibited phospholipase A2 purified from rat platelets in a dose-dependent manner. Cinatrin C3, the most potent component (IC50 70 microM), was noncompetitive with a Ki value of 36 microM. Cinatrins B and C3 also inhibited both porcine pancreas and Naja naja venom phospholipase A2. Inhibition of rat platelet phospholipase A2 by cinatrin C3 was independent of Ca2+ and substrate concentration. Comparison with duramycin, another phospholipase A2 inhibitor, displayed inhibition dependent on substrate concentration when phosphatidylethanolamine was the substrate. These results indicate that the inhibition of phospholipase A2 by cinatrin C3 may result from direct interaction with the enzyme.
3. Enantiospecific synthesis of the phospholipase A2 inhibitors (-)-cinatrin C1 and (+)-cinatrin C3
Anthony N Cuzzupe, Romina Di Florio, Jonathan M White, Mark A Rizzacasa Org Biomol Chem. 2003 Oct 21;1(20):3572-7. doi: 10.1039/b308028e.
The enantiospecific synthesis of (-)cinatrin C1 (3) and (+)-cinatrin C3 (5) from the D-arabinose derivative 9 is described. The stereochemistry at C2 was introduced via a chelation-controlled addition of a carbanion to alpha-hydroxy ketone 8. The best selectivity was achieved by use of the Grignard reagent derived from trimethylsilylacetylene. Transformation of the terminal alkyne into methyl ester 17 followed by acetal hydrolysis and selective lactol oxidation gave cinatrin C1 dimethyl ester (7). Base hydrolysis and acid induced relactonization then gave a 1:1 mixture of cinatrins C1 (3) and C3 (5).
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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 ╳
