Cytoxazone
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01692 |
| CAS | 42902-32-9 |
| Molecular Weight | 223.22 |
| Molecular Formula | C11H13NO4 |
| Purity | >98% |
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Description
Cytoxazone is a cytokine regulator produced by Streptornyces sp. RK95-31. It inhibits the production of IL-4 and IL-10 induced by Pokeween mitogen (PWM) at 6.25-25 μg/mL, but does not inhibit the production of GM-CSF induced by PWM.
Specification
| Synonyms | (-)-Cytoxazone |
| Storage | -20°C |
| IUPAC Name | (4R,5R)-5-(hydroxymethyl)-4-(4-methoxyphenyl)-1,3-oxazolidin-2-one |
| Canonical SMILES | COC1=CC=C(C=C1)C2C(OC(=O)N2)CO |
| InChI | InChI=1S/C11H13NO4/c1-15-8-4-2-7(3-5-8)10-9(6-13)16-11(14)12-10/h2-5,9-10,13H,6H2,1H3,(H,12,14)/t9-,10+/m0/s1 |
| InChI Key | BUIFCOFNXXUCMV-VHSXEESVSA-N |
Properties
| Appearance | Colorless Crystal |
| Boiling Point | 385.3°C at 760 mmHg |
| Melting Point | 118-121°C |
| Density | 1.282 g/cm3 |
| Solubility | Soluble in DMSO |
Reference Reading
1. Stereoselective Synthesis of Oxazolidin-2-Ones via an Asymmetric Aldol/Curtius Reaction: Concise Total Synthesis of (-)-Cytoxazone
Hosam Choi, Hanho Jang, Joohee Choi, Kiyoun Lee Molecules. 2021 Jan 23;26(3):597. doi: 10.3390/molecules26030597.
Herein, we are reporting an efficient approach toward the synthesis of 4,5-disubstituted oxazolidin-2-one scaffolds. The developed approach is based on a combination of an asymmetric aldol and a modified Curtius protocol, which uses an effective intramolecular ring closure to rapidly access a range of oxazolidin-2-one building blocks. This strategy also permits a straightforward and concise asymmetric total synthesis of (-)-cytoxazone. Consisting of three steps, this is one of the shortest syntheses reported to date. Ultimately, this convenient platform would provide a promising method for the early phases of drug discovery.
2. Synthesis Approaches to (-)-Cytoxazone, a Novel Cytokine Modulator, and Related Structures
Izabel L Miranda, Ítala K B Lopes, Marisa A N Diaz, Gaspar Diaz Molecules. 2016 Sep 6;21(9):1176. doi: 10.3390/molecules21091176.
(-)-Cytoxazone, originally isolated from cultures of a Streptomyces species has an oxazolidin-2-one 4,5-disubstituted ring. It is known that this natural product presents a cytokine modulator effect through the signaling pathway of Th2 cells (type 2 cytokines), which are involved in the process of growth and differentiation of cells. From this, the interest in the development of research aimed at the total synthesis of this molecule and its analogs has remained high, which can be confirmed by the large number of publications on the topic, more than 30 to date. This review focuses on the various creative methods for the synthesis of (-)-cytoxazone and its congeners. The assessment of the preparation of this oxazolidinone and related structures serves as a treatise on the efforts made in the synthesis of this important class of compound from its first total synthesis in 1999.
3. Stereoselective synthesis of (-)-cytoxazone and its unnatural congener (+)-5-epi-cytoxazone
Izabel Luzia Miranda, Pedro Henrique Costa Dos Santos, Markus Kohlhoff, Gislaine Aparecida Purgato, Marisa Alves Nogueira Diaz, Gaspar Diaz-Muñoz Chirality. 2021 Aug;33(8):479-489. doi: 10.1002/chir.23334. Epub 2021 Jul 1.
An interesting protocol for stereoselective synthesis of (-)-cytoxazone and its unnatural stereoisomer (+)-5-epi-cytoxazone from d-4-hydroxyphenylglycine in overall yields of 10% and 16%, respectively, is described. The stereoselective addition of cyanide to an N-Boc protected aminoaldehyde (tert-butyl ((R)-1-(4-methoxyphenyl)-2-oxoethyl)carbamate) (5) constitutes the key step in this approach, producing a mixture of cyanohydrins 6a and b (1,2-anti and 1,2-syn tert-butyl (2-cyano-2-hydroxy-1-(4-methoxyphenyl)ethyl)carbamate) in 89% yield, with reasonable stereoselectivity (1.0:1.8) in favor of the anti-Felkin product (1,2-syn). A one-pot sequence of three successive steps from this mixture produced the oxazolidinone isomers 9a and b ((4R,5R)- and (4R,5S)-4-(4-methoxyphenyl)-2-oxooxazolidine-5-carboxylate). Chromatographic column separation and reduction of the ester function of both precursors led to (-)-cytoxazone and (+)-5-epi-cytoxazone.
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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 ╳
