β-Naphthocyclinone epoxide
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| Category | Antibiotics |
| Catalog number | BBF-05599 |
| CAS | 83333-54-4 |
| Molecular Weight | 692.62 |
| Molecular Formula | C35H32O15 |
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Description
It is a naphthoquinone antibiotic isolated from Streptomyces arenae. It has activity against gram-positive bacteria.
Specification
| Synonyms | beta-Naphthocyclinone epoxide; 8a,12a-Epoxy-6,15-methano-12H-pyrano[4'',3'':6',7']naphtho[2',3':5,6]cyclohepta[1,2-g]-2-benzopyran-3,10-diacetic acid, 6-(acetyloxy)-1,3,4,6,8,9,10,13,15,16-decahydro-7,14,17-trihydroxy-1,12-dimethyl-8,13,16-trioxo-, α3-methyl ester, (1S,3R,6S,8aR,10R,12S,12aS,15R)-; b-Naphthocyclinone epoxide |
| IUPAC Name | 2-[(1R,6S,7S,9R,11R,16S,21R,23S)-16-acetyloxy-3,14,25-trihydroxy-21-(2-methoxy-2-oxoethyl)-7,23-dimethyl-5,12,27-trioxo-8,22,29-trioxaoctacyclo[14.11.1.16,11.02,15.04,13.06,11.017,26.019,24]nonacosa-2(15),3,13,17(26),18,24-hexaen-9-yl]acetic acid |
| Canonical SMILES | CC1C2=C(C3=C(C=C2CC(O1)CC(=O)OC)C4(CC(C3=O)C5=C4C(=C6C(=C5O)C(=O)C78C(OC(CC7(C6=O)O8)CC(=O)O)C)O)OC(=O)C)O |
| InChI | InChI=1S/C35H32O15/c1-11-21-14(5-15(47-11)8-20(39)46-4)6-18-23(28(21)41)27(40)17-10-33(18,49-13(3)36)26-22(17)29(42)24-25(30(26)43)31(44)34-9-16(7-19(37)38)48-12(2)35(34,50-34)32(24)45/h6,11-12,15-17,41-43H,5,7-10H2,1-4H3,(H,37,38)/t11-,12-,15+,16-,17+,33-,34-,35+/m0/s1 |
| InChI Key | QTTNTZSBZNWXSL-UGRSFXRNSA-N |
Properties
| Appearance | Yellow Amorphous Powder |
| Antibiotic Activity Spectrum | Gram-positive becteria |
| Melting Point | 194°C |
| Solubility | Soluble in Chloroform |
Reference Reading
1. [Fatty acid epoxides in the regulation of the inflammation]
O Y Kytikova, Y K Denisenko, T P Novgorodtseva, N V Bocharova, I S Kovalenko Biomed Khim. 2022 Jun;68(3):177-189. doi: 10.18097/PBMC20226803177.
Cyclooxygenase and lipoxygenase derived lipid metabolites of polyunsaturated fatty acids (PUFAs), as well as their role in the inflammation, have been studied quite thoroughly. However, cytochrome P450 derived lipid mediators, as well as their participation in the regulation of the inflammation, need deeper understanding. In recent years, it has become known that PUFAs are oxidized by cytochrome P450 epoxygenases to epoxy fatty acids, which act as the extremely powerful lipid mediators involved in resolving inflammation. Recent studies have shown that the anti-inflammatory mechanisms of ω-3 PUFAs are also mediated by their conversion to the endocannabinoid epoxides. Thus, it is clear that a number of therapeutically relevant functions of PUFAs are due to their conversion to PUFA epoxides. However, with the participation of cytochrome P450 epoxygenases, not only PUFA epoxides, but also other metabolites are formed. They are further are converted by epoxide hydrolases into pro-inflammatory dihydroxy fatty acids and anti-inflammatory dihydroxyeicosatrienoic acids. The study of the role of PUFA epoxides in the regulation of the inflammation and pharmacological modeling of the activity of epoxide hydrolases are the promising strategies for the treatment of the inflammatory diseases. This review systematizes the current literature data of the fatty acid epoxides, in particular, the endocannabinoid epoxides. Their role in the regulation of inflammation is discussed.
2. Efficient methods for the synthesis of chiral 2-oxazolidinones as pharmaceutical building blocks
Ken Okuno, Ryuichi Nishiyori, Koki Abe, Taiki Mori, Seiji Shirakawa Chirality. 2022 Jul;34(7):915-924. doi: 10.1002/chir.23452. Epub 2022 Apr 29.
Although the wide variety of heterocyclic compounds is common knowledge, chiral 2-oxazolidinones are recognized as some of the most important heterocycles in medicinal chemistry. Many important pharmaceutical molecules have been constructed based on the chiral 2-oxazolidinone backbone. Therefore, the development of even more efficient catalytic methods for the synthesis of chiral 2-oxazolidinones remains a very important pursuit in the field of synthetic organic chemistry. This review summarizes the coupling reactions of epoxides and isocyanates for the preparation of 2-oxazolidinones. Both metal catalysts and organocatalysts promote these reactions. Optically pure 2-oxazolidinones are prepared from optically pure epoxide substrates via these catalytic methods. A synthetic example of a commercially available pharmaceutical compound utilizing this method is also introduced.
3. Use of Limonene Epoxides and Derivatives as Promising Monomers for Biobased Polymers
Elodie Louisy, Veronika Khodyrieva, Sandra Olivero, Véronique Michelet, Alice Mija Chempluschem. 2022 Aug;87(8):e202200190. doi: 10.1002/cplu.202200190.
(R)-Limonene, a renewable terpene, and its epoxidized derivatives, i. e. limonene epoxides, have prompted growing attention over the last decade as building blocks for the synthesis of biobased monomers and polymers. With the goal of replacing petroleum-based polymers several polymerization techniques have been applied on limonene oxide and limonene dioxide monomers. This paper aims to contribute to the literature by presenting a review dedicated to limonene oxide and dioxide as raw monomers of renewable origin for the development of biobased polymers. The polymerization techniques described are namely the homopolymerization, the copolymerization with carbon dioxide and anhydrides, and the copolymerization of limonene epoxide-based monomers. Limonene oxide polymerizations will be investigated first, followed by limonene dioxide polymerizations.
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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 ╳
