Scyphostatin
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02889 |
| CAS | 169062-93-5 |
| Molecular Weight | 485.66 |
| Molecular Formula | C29H43NO5 |
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Description
It is a mammalian N-SMase inhibitor produced by the strain of Trichopeziza mollissima SANK 13892. It inhibits N-SMase with IC50 of 1.0 μmol/L.
Specification
| Synonyms | (2E,4E,6E,12E)-(8R,10S,14R)-8,10,12,14-Tetramethyl-hexadeca-2,4,6,12-tetraenoic acid [(S)-1-hydroxymethyl-2-((1S,2S,6S)-2-hydroxy-3-oxo-7-oxa-bicyclo[4.1.0]hept-4-en-2-yl)-ethyl]-amide; (2'S,2''E,4S,4''E,5S,6S,6''E,8''R,10''S,12''E,14''R)-4,5-epoxy-6-hydroxy-6-[3'-hydroxy-2'-(8'',10'',12'',14''-tetramethylhexadeca-2'',4'',6'',12''-tetraenoylamino)-propyl]-2-cyclohexen-1-one; (+)-scyphostatin |
| IUPAC Name | (2E,4E,6E,8R,10S,12E,14R)-N-[(2S)-1-hydroxy-3-[(1S,2S,6S)-2-hydroxy-3-oxo-7-oxabicyclo[4.1.0]hept-4-en-2-yl]propan-2-yl]-8,10,12,14-tetramethylhexadeca-2,4,6,12-tetraenamide |
| Canonical SMILES | CCC(C)C=C(C)CC(C)CC(C)C=CC=CC=CC(=O)NC(CC1(C2C(O2)C=CC1=O)O)CO |
| InChI | InChI=1S/C29H43NO5/c1-6-20(2)15-22(4)17-23(5)16-21(3)11-9-7-8-10-12-27(33)30-24(19-31)18-29(34)26(32)14-13-25-28(29)35-25/h7-15,20-21,23-25,28,31,34H,6,16-19H2,1-5H3,(H,30,33)/b8-7+,11-9+,12-10+,22-15+/t20-,21+,23+,24+,25+,28+,29-/m1/s1 |
| InChI Key | KSIWZCYBCSQXTA-JPOQAJQISA-N |
Properties
| Appearance | Pale Yellow Powder |
| Solubility | Soluble in Methanol |
Reference Reading
1. A strategy for the late-stage divergent syntheses of scyphostatin analogues
Jacob Y Cha, G Leslie Burnett th, Yaodong Huang, Jarrod B Davidson, Thomas R R Pettus J Org Chem. 2011 Mar 4;76(5):1361-71. doi: 10.1021/jo102327e. Epub 2011 Jan 21.
This account details the synthesis of two scyphostatin analogues exhibiting a reactive polar epoxycyclohexenone core and various amide side chains outfitted for late-stage chemical derivatization into the desirable lipophilic tails. Our efforts highlight a key ipso-dearomatization process and provide new insights regarding the incompatibility and orthogonal reactivity of scyphostatin's functional groups. We further showcase the utility of resorcinol derived 2,5-cyclohexadienones as synthetic platforms capable of participating in selective chemical reactivity, and we further demonstrate their potential for rapid elaboration into complex structural motifs.
2. Concise approach to the carbocyclic core of the naturally occurring sphingomyelinase inhibitor scyphostatin
Goverdhan Mehta, Nagi Reddy Modugu J Org Chem. 2013 Apr 5;78(7):3367-73. doi: 10.1021/jo3028196. Epub 2013 Mar 6.
A flexible strategy toward the carbocyclic core of the naturally occurring sphingomyelinase inhibitor scyphostatin, from the readily available Diels-Alder adducts of cyclopentadiene and 2-allyl-p-benzoquinone, has been devised. This approach leverages the stereochemical predisposition of the norbornyl-fused scaffolds to generate the desired stereochemical pattern and leads to a concise synthesis of the epoxycyclohexenoid core of scyphostatin with a manipulable allyl side arm.
3. Synthesis of Scyphostatin Analogues through Hypervalent Iodine-Mediated Phenol Dearomatization
Mourad El Assal, Philippe A Peixoto, Romain Coffinier, Tony Garnier, Denis Deffieux, Karinne Miqueu, Jean-Marc Sotiropoulos, Laurent Pouységu, Stéphane Quideau J Org Chem. 2017 Nov 17;82(22):11816-11828. doi: 10.1021/acs.joc.7b02366. Epub 2017 Oct 18.
A concise synthesis of two scyphostatin analogues is achieved from readily available ortho-substituted phenols. Key features include an asymmetric and biomimetic hydroxylative phenol dearomatization (HPD) reaction promoted by a chiral salen-type bis(λ5-iodane) reagent, followed by an in situ regio- and diastereocontrolled epoxidation.
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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 ╳
