FR 900482
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-03565 |
| CAS | 102363-08-6 |
| Molecular Weight | 321.28 |
| Molecular Formula | C14H15N3O6 |
Online Inquiry
Description
FR 900482 is produced by the strain of Streptomyces sandaensis No. 6897. It is highly sensitive to Bacillus stearothermophilus var. calidolactis C 953 and has anti-P388, B16, EL4, FM3A, L1210, BHK-21 and other cell activities.
Specification
| Synonyms | Antibiotic FR 900482; BRN 4886722; (5-Formyl-7,9-dihydroxy-1,1a,2,8,9,9a-hexahydro-3,9-epoxyazireno[2,3-c][1]benzazocin-8-yl)methyl hydrogen carbonimidate |
| IUPAC Name | [(8R,9R,10R,12R)-4-formyl-6,9-dihydroxy-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2(7),3,5-trien-8-yl]methyl carbamate |
| Canonical SMILES | C1C2C(N2)C3(C(C4=C(N1O3)C=C(C=C4O)C=O)COC(=O)N)O |
| InChI | InChI=1S/C14H15N3O6/c15-13(20)22-5-7-11-9(1-6(4-18)2-10(11)19)17-3-8-12(16-8)14(7,21)23-17/h1-2,4,7-8,12,16,19,21H,3,5H2,(H2,15,20)/t7-,8+,12+,14+/m0/s1 |
| InChI Key | XVPSPMLUMQEEIU-PWLJWKHCSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; neoplastics (Tumor) |
| Boiling Point | 572.3±60.0°C at 760 mmHg |
| Melting Point | 175°C |
| Density | 1.7±0.1 g/cm3 |
Reference Reading
1. 6-Bromomethyl-4H-1,3-dioxin: a versatile bromomethyl vinyl ketone equivalent for heterocycle and carbocycle construction
Thomas J Greshock, Raymond L Funk J Am Chem Soc. 2002 Feb 6;124(5):754-5. doi: 10.1021/ja0123554.
6-Bromomethyl-4H-1,3-dioxin has been prepared in three steps from allyl iodide. A variety of enolates were then alkylated with this bromide. The resulting 6-alkyl-4H-1,3-dioxins were either subjected to further multistep transformations and/or heated to effect facile retrocycloaddition reactions. The resulting enones smoothly participated in novel endo-conjugate addition reactions with both carbon and nitrogen nucleophiles. For example, several bicyclo[4.3.1]decan-3,10-diones, the carbon framework of the CP compounds, were constructed using this novel annulation strategy. In another natural product study, a benzazocine related to the heterocyclic framework of the ring-opened tautomeric form of FR-900482 was also prepared using this methodology. Finally, a piperidin-4-one obtained from a 6-endo conjugate addition was converted to the naturally occurring (2S,4R)-4-hydroxypipecolic acid. Collectively, these examples document the synthetic equivalency of dioxin 1 with bromomethyl vinyl ketone and, moreover, delineate a strategy for accomplishing the sequential reactions with nucleophiles at the alpha' followed by the beta electrophilic sites.
2. Total synthesis of natural product DNA cross-linking agents
R S Coleman Curr Opin Drug Discov Devel. 2001 Jul;4(4):435-49.
A variety of naturally occurring compounds interact with duplex DNA by the formation of covalent cross-links. This review describes recent progress on the total synthesis of four natural product families, including the mitomycins, the structurally and functionally related agent FR-900482, the bis-pyrrole isochrysohermidine and the azinomycins.
3. Intramolecular 1,3-dipolar cycloaddition strategy for enantioselective synthesis of FR-900482 analogues
M Kambe, E Arai, M Suzuki, H Tokuyama, T Fukuyama Org Lett. 2001 Aug 9;3(16):2575-8. doi: 10.1021/ol016243t.
[reaction: see text] Enantioselective synthesis of FR-900482 analogues is described. The key reaction of the synthesis is intramolecular 1,3-dipolar cycloaddition of a highly functionalized nitrile oxide with complete stereo- and regioselectivities to construct the eight-membered benzazocine ring.
Recommended Products
| BBF-01826 | Deoxymannojirimycin | Inquiry |
| BBF-01825 | Loganin | Inquiry |
| BBF-03753 | Baicalin | Inquiry |
| BBF-01829 | Deoxynojirimycin | Inquiry |
| BBF-03755 | Actinomycin D | Inquiry |
| BBF-03754 | Castanospermine | Inquiry |
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 ╳
Recently viewed products
Waol B | Ramoplanin | Cefuzonam | Hydramycin | ICM0201 | Chlorolecideoidin | Streptovaricin C | FR 900482
