CP-263114
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02793 |
| CAS | 186700-09-4 |
| Molecular Weight | 552.61 |
| Molecular Formula | C31H36O9 |
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Description
CP-263114 inhibits Ras farnesyl transferase from the mouse brain and Squalene synthase.
Specification
| IUPAC Name | 2-[(1S,2R,9S,12R,13R,15S)-15-[(E)-hex-4-enoyl]-12-[(E)-oct-6-enyl]-4,6,18-trioxo-5,16,17-trioxapentacyclo[7.7.2.01,10.02,13.03,7]octadeca-3(7),10-dien-9-yl]acetic acid |
| Canonical SMILES | CC=CCCCCCC1C=C2C3(CC4=C(C5C1CC(OC52OC3=O)C(=O)CCC=CC)C(=O)OC4=O)CC(=O)O |
| InChI | InChI=1S/C31H36O9/c1-3-5-7-8-9-11-12-18-14-23-30(17-24(33)34)16-20-25(28(36)38-27(20)35)26-19(18)15-22(21(32)13-10-6-4-2)39-31(23,26)40-29(30)37/h3-6,14,18-19,22,26H,7-13,15-17H2,1-2H3,(H,33,34)/b5-3+,6-4+/t18-,19+,22-,26+,30-,31+/m0/s1 |
| InChI Key | PZLSMKXFWOLXHD-FCTVBEETSA-N |
Reference Reading
1. Synthetic studies on CP-225,917 and CP-263,114: access to advanced tetracyclic systems by intramolecular conjugate displacement and [2,3]-Wittig rearrangement
Farzad Malihi, Derrick L J Clive, Che-Chien Chang, Minaruzzaman J Org Chem. 2013 Feb 1;78(3):996-1013. doi: 10.1021/jo302467w. Epub 2013 Jan 17.
An advanced intermediate related to the structures of CP-225,917 and CP-263,114 was constructed by a sequence based on the use of Grob-like fragmentation, intramolecular conjugate displacement, and [2,3]-Wittig rearrangement. A variant of the [2,3]-Wittig rearrangement was developed.
2. Elucidation of Late-Stage Biosynthesis of Phomoidride: Proposal of Cyclization Mechanism Affording Characteristic Nine-Membered Ring of Fungal Dimeric Anhydride
Shintaro Yamamoto, Taro Matsuyama, Taro Ozaki, Junya Takino, Hajime Sato, Masanobu Uchiyama, Atsushi Minami, Hideaki Oikawa J Am Chem Soc. 2022 Nov 23;144(46):20998-21004. doi: 10.1021/jacs.2c09308. Epub 2022 Nov 14.
Antihypercholesterolemic agent phomoidride (PMD) B has a highly elaborated bicyclo[4.3.1]deca-1,6-diene core scaffold derived from dimeric anhydride with a nine-membered ring. This report elucidated the late stage transformation from an anhydride monomer to PMD B through the heterologous expression of three enzyme genes, TstC, TstK, and TstE. Additional in vitro studies of TstK and TstE provided evidence on the formation of PMD via dimerization, three-step oxidation, and unusual methylation-triggered bicyclic ketal formation. Elucidation of the function of cyclase TstC prompts us to examine the cyclization mechanism of TstC by using a computational approach. Computational analytical data on PMD and structurally related glaucanic acid indicated that the initial decarboxylation of monomer results in enolate and subsequent double Michael reactions of another monomer, followed by an optional aldol reaction proceeding in an endo-selective manner to give cycloadducts, supporting the fact that the starting orientation of two monomers is directly transferred to the product configurations.
3. Studies on the total synthesis of (-)-CP-263,114
Takehiko Yoshimitsu, Shuji Sasaki, Yoshimasa Arano, Hiroto Nagaoka J Org Chem. 2004 Dec 24;69(26):9262-8. doi: 10.1021/jo048681u.
Alkoxyl radicals have a wide range of applications in organic synthesis due to their remarkable chemical properties in molecular transformation. The present study shows two types of alkoxyl radicals (primary vs tertiary) to selectively undergo dehydrogenation and beta-scission to give rise to key structural elements of (-)-CP-263,114 (1). By alkoxyl radical transformation followed by installation of the C19-C25 (CP numbering) side chain and the bridged bisacetal unit, the functionalized CP precursor 2 was obtained.
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
