Fredericamycin A
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| Category | Antibiotics |
| Catalog number | BBF-01442 |
| CAS | 80455-68-1 |
| Molecular Weight | 539.49 |
| Molecular Formula | C30H21NO9 |
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Description
Produced by the strain of Streptomyces griseus (FCRC-48), Fredericamycin A has anti-gram-positive bacterial and fungal activity, and shows strong anti-tumor effect in vivo and in vitro.
Specification
| Synonyms | Fcrc-A48; NSC-305263; (S)-6',7'-Dihydro-4,9,9'-trihydroxy-6-methoxy-3'-[(1E,3E)-1,3-pentadienyl]spiro[2H-benz[f]indene-2,8'-[8H]cyclopent[g]isoquinoline]-1,1',3,5,8(2'H)-pentone; 4',9,9'-trihydroxy-6'-methoxy-3-[(1E,3E)-penta-1,3-dienyl]spiro[6,7-dihydro-2H-cyclopenta[g]isoquinoline-8,2'-cyclopenta[g]naphthalene]-1,1',3',5',8'-pentone |
| IUPAC Name | (8S)-1',3',9-trihydroxy-6'-methoxy-3-[(1E,3E)-penta-1,3-dienyl]spiro[6,7-dihydro-2H-cyclopenta[g]isoquinoline-8,2'-cyclopenta[b]naphthalene]-1,4',5',8',9'-pentone |
| Canonical SMILES | CC=CC=CC1=CC2=CC3=C(C(=C2C(=O)N1)O)C4(CC3)C(=C5C(=C4O)C(=O)C6=C(C5=O)C(=O)C=C(C6=O)OC)O |
| InChI | InChI=1S/C30H21NO9/c1-3-4-5-6-14-10-13-9-12-7-8-30(22(12)26(36)17(13)29(39)31-14)27(37)20-21(28(30)38)25(35)19-18(24(20)34)15(32)11-16(40-2)23(19)33/h3-6,9-11,36-38H,7-8H2,1-2H3,(H,31,39)/b4-3+,6-5+/t30-/m0/s1 |
| InChI Key | NJLAGDPRCAPJIF-MHSJTTIKSA-N |
Properties
| Appearance | Red Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; fungi; neoplastics (Tumor) |
| Boiling Point | 1030.142°C at 760 mmHg |
| Melting Point | >350°C |
| Density | 1.654 g/cm3 |
| Solubility | Soluble in Acetic acid, DMF, DMSO, Pyridine |
Reference Reading
1. Synthetic Approach to the ABCD Ring System of Anticancer Agent Fredericamycin A via Claisen Rearrangement and Ring-Closing Metathesis as Key Steps
Sambasivarao Kotha, Subba Rao Cheekatla, Ambareen Fatma ACS Omega. 2019 Oct 14;4(17):17109-17116. doi: 10.1021/acsomega.9b01178. eCollection 2019 Oct 22.
A new synthetic strategy to the ABCD ring system of the anticancer agent fredericamycin A (NSC-305263) was realized by the Diels-Alder reaction and olefin metathesis as key steps. The tactics developed here for the construction of the ABCD ring system also involve double Claisen rearrangement followed by a retro-Diels-Alder reaction and ring-closing metathesis. The metathesis approach performs a key role in the construction of A and D rings of the ABCD core unit. More importantly, ABCD fragment synthesis was accomplished without the involvement of protecting groups.
2. Assembly of multicyclic isoquinoline scaffolds from pyridines: formal total synthesis of fredericamycin A
Fang-Xin Wang, Jia-Lei Yan, Zhixin Liu, Tingshun Zhu, Yingguo Liu, Shi-Chao Ren, Wen-Xin Lv, Zhichao Jin, Yonggui Robin Chi Chem Sci. 2021 Jun 28;12(30):10259-10265. doi: 10.1039/d1sc02442f. eCollection 2021 Aug 4.
The construction of an isoquinoline skeleton typically starts with benzene derivatives as substrates with the assistance of acids or transition metals. Disclosed here is a concise approach to prepare isoquinoline analogues by starting with pyridines to react with β-ethoxy α,β-unsaturated carbonyl compounds under basic conditions. Multiple substitution patterns and a relatively large number of functional groups (including those sensitive to acidic conditions) can be tolerated in our method. In particular, our protocol allows for efficient access to tricyclic isoquinolines found in hundreds of natural products with interesting bioactivities. The efficiency and operational simplicity of introducing structural complexity into the isoquinoline frameworks can likely enable the collective synthesis of a large set of natural products. Here we show that fredericamycin A could be obtained via a short route by using our isoquinoline synthesis as a key step.
3. Novel Fredericamycin Variant Overproduced by a Streptomycin-resistant Streptomyces albus subsp. chlorinus Strain
Marta Rodríguez Estévez, Maksym Myronovskyi, Birgit Rosenkränzer, Thomas Paululat, Lutz Petzke, Jeanette Ristau, Andriy Luzhetskyy Mar Drugs. 2020 May 28;18(6):284. doi: 10.3390/md18060284.
Streptomycetes are an important source of natural products potentially applicable in the pharmaceutical industry. Many of these drugs are secondary metabolites whose biosynthetic genes are very often poorly expressed under laboratory cultivation conditions. In many cases, antibiotic-resistant mutants exhibit increased production of natural drugs, which facilitates the identification and isolation of new substances. In this study, we report the induction of a type II polyketide synthase gene cluster in the marine strain Streptomyces albus subsp. chlorinus through the selection of streptomycin-resistant mutants, resulting in overproduction of the novel compound fredericamycin C2 (1). Fredericamycin C2 (1) is structurally related to the potent antitumor drug lead fredericamycin A.
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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 ╳
