CP-225917
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| Category | Enzyme inhibitors |
| Catalog number | BBF-02792 |
| CAS | |
| Molecular Weight | 570.63 |
| Molecular Formula | C31H38O10 |
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Description
CP-225917 inhibits Ras farnesyl transferase from the mouse brain and Squalene synthase.
Specification
| IUPAC Name | 2-[(1S,8R,11R,14S,15S)-11-hydroxy-15-[(E,2R)-2-hydroxy-3-oxooct-6-enyl]-14-[(E)-oct-6-enyl]-3,5,9-trioxo-4,10-dioxatetracyclo[9.4.0.02,6.08,12]pentadeca-2(6),12-dien-8-yl]acetic acid |
| Canonical SMILES | CC=CCCCCCC1C=C2C3(CC4=C(C(C1CC(C(=O)CCC=CC)O)C2(OC3=O)O)C(=O)OC4=O)CC(=O)O |
| InChI | InChI=1S/C31H38O10/c1-3-5-7-8-9-11-12-18-14-23-30(17-24(34)35)16-20-25(28(37)40-27(20)36)26(31(23,39)41-29(30)38)19(18)15-22(33)21(32)13-10-6-4-2/h3-6,14,18-19,22,26,33,39H,7-13,15-17H2,1-2H3,(H,34,35)/b5-3+,6-4+/t18-,19+,22-,26+,30-,31+/m1/s1 |
| InChI Key | PXJMQYXPSSIUGS-LZQVYANHSA-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. Wharton-fragmentation-based approach to the carbocyclic core of the phomoidrides
Graham K Murphy, Naoto Hama, Aaron Bedermann, Ping Dong, Chris M Schneider, Travis C McMahon, Ran N Tao, Barry M Twenter, David A Spiegel, John L Wood Org Lett. 2012 Sep 7;14(17):4544-7. doi: 10.1021/ol302011b. Epub 2012 Aug 23.
The carbocyclic core of the phomoidrides has been synthesized efficiently and in high yield. Key steps include a phenolic oxidation/intramolecular Diels-Alder sequence, tandem radical cyclization, and a late-stage Wharton fragmentation of a densely functionalized isotwistane skeleton.
3. Total synthesis of the CP-molecules (CP-263,114 and CP-225,917, phomoidrides B and A). 3. Completion and synthesis of advanced analogues
K C Nicolaou, Y-L Zhong, P S Baran, J Jung, H-S Choi, W H Yoon J Am Chem Soc. 2002 Mar 13;124(10):2202-11. doi: 10.1021/ja0120126.
The completion of the total syntheses of the CP-molecules is reported. Several strategies and tactics, including the use of amide-based protecting groups for the homologated C-29 carboxylic acid and the use of an internal pyran protecting group scheme, are discussed. The endeavors leading to the design of new methods for the homologation of hindered aldehydes and to the isolation of a polycyclic byproduct (23), which inspired the development of a new series of reactions based on iodine(V) reagents, are described. In addition, the discovery and development of the LiOH-mediated conversion of CP-263,114 (1) to CP-225,917 (2) is described, and a mechanistic rationale is presented. Finally, a synthetic route to complex analogues of the CP-molecules harboring a maleimide moiety in place of the maleic anhydride is presented.
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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 ╳
