EI-1941-2
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02814 |
| CAS | 189828-32-8 |
| Molecular Weight | 238.24 |
| Molecular Formula | C12H14O5 |
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Description
It is originally isolated from Farrowia sp. E-1941. EI-1941-2 inhibited recombinant human ICE with an IC50 of 0.006 μmol/L. It also inhibits elastase and cathepsin.
Specification
| IUPAC Name | (1aS,2R,5R,7aS)-2-hydroxy-5-propyl-2,5,6,7a-tetrahydro-1aH-oxireno[2,3-g]isochromene-3,7-dione |
| Canonical SMILES | CCCC1CC2=C(C(C3C(C2=O)O3)O)C(=O)O1 |
| InChI | InChI=1S/C12H14O5/c1-2-3-5-4-6-7(12(15)16-5)9(14)11-10(17-11)8(6)13/h5,9-11,14H,2-4H2,1H3/t5-,9-,10-,11+/m1/s1 |
| InChI Key | HNHUZZHNVSTBDM-PRTGYXNQSA-N |
Properties
| Boiling Point | 503.1±50.0°C at 760 mmHg |
| Density | 1.4±0.1 g/cm3 |
Reference Reading
1. Enantio- and diastereoselective total synthesis of EI-1941-1, -2, and -3, inhibitors of interleukin-1beta converting enzyme, and biological properties of their derivatives
Mitsuru Shoji, Takao Uno, Hideaki Kakeya, Rie Onose, Isamu Shiina, Hiroyuki Osada, Yujiro Hayashi J Org Chem. 2005 Nov 25;70(24):9905-15. doi: 10.1021/jo0516436.
[reaction: see text] The first asymmetric total synthesis of EI-1941-1, -2, and -3, inhibitors of the interleukin-1beta converting enzyme (ICE), has been accomplished, starting from a chiral epoxy iodoquinone 11, a key intermediate in our total synthesis of epoxyquinols A and B. Despite a failure to synthesize the inhibitors by our postulated biosynthetic route, we were able to diastereoselectively synthesize them via an intramolecular carboxypalladation with the key steps being a 6-endo cyclization mode followed by beta-hydride elimination. The investigation of the biological properties of EI-1941-1, -2, and -3 and their derivatives disclosed them to be potent and effective ICE inhibitors with less cytotoxicity than EI-1941-1 and -2 in a cultured cell system.
2. Total synthesis of the interleukin-1beta converting enzyme inhibitor EI-1941-2 using tandem oxa-electrocyclization/oxidation1
Andrew S Kleinke, Chaomin Li, Nicolas Rabasso, John A Porco Jr Org Lett. 2006 Jun 22;8(13):2847-50. doi: 10.1021/ol060954f.
[reaction: see text] The total synthesis of the interleukin-1beta converting enzyme inhibitor EI-1941-2 was achieved utilizing tandem oxidation/oxa-electrocyclization/oxidation to access a key alpha-pyrone intermediate. Support for the tandem reaction mechanism was obtained by evaluation of a stepwise oxidation protocol.
3. Stereoselective total synthesis of ent-EI-1941-2 and Epi-ent-EI-1941-2
Mitsuru Shoji, Takao Uno, Yujiro Hayashi Org Lett. 2004 Nov 25;6(24):4535-8. doi: 10.1021/ol0481479.
The first asymmetric total syntheses of ent-EI-1941-2 and epi-ent-EI-1941-2 have been accomplished, starting from a chiral epoxy iodoquinone 6, a key intermediate in our total syntheses of epoxyquinols A and B. A key step in the preparation of ent-EI-1941-2 is an intramolecular carboxypalladation via a 6-endo cyclization mode, followed by beta-hydride elimination, while carboxymercuration is a key step in the synthesis of epi-ent-EI-1941-2. [reaction: see text]
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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 ╳
