FR 66979
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| Category | Antibiotics |
| Catalog number | BBF-03552 |
| CAS | 102409-60-9 |
| Molecular Weight | 323.30 |
| Molecular Formula | C14H17N3O6 |
| Purity | 97% |
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Description
FR 66979 is produced by the strain of Streptomyces sandaensis No. 6897. It has inhibitory activity against tumor cells, including leukemia P388 cells and melanoma B16 cells.
Specification
| Synonyms | [7,9-Dihydroxy-5-(hydroxymethyl)-1,1a,2,8,9,9a-hexahydro-3,9-epoxyazireno[2,3-c][1]benzazocin-8-yl]methyl hydrogen carbonimidate |
| IUPAC Name | [6,9-dihydroxy-4-(hydroxymethyl)-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)CO)COC(=O)N)O |
| InChI | InChI=1S/C14H17N3O6/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/h1-2,7-8,12,16,18-19,21H,3-5H2,(H2,15,20) |
| InChI Key | WUQJQATXUALTBZ-UHFFFAOYSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Boiling Point | 613.3°C at 760 mmHg |
| Melting Point | 165-170°C |
| Density | 1.74 g/cm3 |
Reference Reading
1. A concise total synthesis of (+)-FR900482 and (+)-FR66979
Ted C Judd, Robert M Williams J Org Chem. 2004 Apr 16;69(8):2825-30. doi: 10.1021/jo035828t.
The concise, enantioselective total synthesis of the potent antitumor antibiotics (+)-FR900482 and (+)-FR66979 are described. Sharpless asymmetric epoxidation technology has been deployed to construct the optically active aziridine-containing fragment that is joined to the aromatic moiety in a highly convergent manner. Dimethyldioxirane effects the remarkable one-step deprotection/oxidative cyclization of an eight-membered ring amino-ketone to the unique hydroxylamine hemiketal ring system that is a distinctive structural motif of FR900482. This reaction has been exploited in a concise 33-step enantioselective total synthesis of FR900482.
2. Observations on the covalent cross-linking of the binding domain (BD) of the high mobility group I/Y (HMG I/Y) proteins to DNA by FR66979
S R Rajski, R M Williams Bioorg Med Chem. 2000 Jun;8(6):1331-42. doi: 10.1016/s0968-0896(00)00078-x.
FR66979, a drug closely related to the mitomycin C class of antitumor antibiotics, is shown to covalently cross-link DNA to the DNA-binding domain of the High Mobility Group I/Y (HMG I/Y) DNA-binding proteins in the minor groove.
3. Synthesis of polycyclic benzofused nitrogen heterocycles via a tandem ynamide benzannulation/ring-closing metathesis strategy. Application in a formal total synthesis of (+)-FR900482
Xiao Yin Mak, Aimee L Crombie, Rick L Danheiser J Org Chem. 2011 Mar 18;76(6):1852-73. doi: 10.1021/jo2000308. Epub 2011 Feb 15.
A two-stage "tandem strategy" for the synthesis of benzofused nitrogen heterocycles is described that is particularly useful for the construction of systems with a high level of substitution on the benzenoid ring. The first stage in the strategy involves a benzannulation based on the reaction of cyclobutenones with ynamides. This cascade process proceeds via a sequence of four pericyclic reactions and furnishes a multiply substituted aniline derivative which can bear a variety of functionalized substituents at the position ortho to the nitrogen. In the second stage of the tandem strategy, ring-closing metathesis generates the nitrogen heterocyclic ring. This two-step sequence provides efficient access to highly substituted dihydroquinolines, benzazepines, benzazocines, and related benzofused nitrogen heterocyclic systems. The application of this chemistry in a concise formal total synthesis of the anticancer agents (+)-FR900482 and (+)-FR66979 is described.
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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 ╳
