Brevicompanine B
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| Category | Bioactive by-products |
| Catalog number | BBF-04591 |
| CAS | 215121-47-4 |
| Molecular Weight | 367.48 |
| Molecular Formula | C22H29N3O2 |
| Purity | >99% by HPLC |
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Description
A diketopiperazine-related metabolite produced by penicillium brevicompactum and aspergillus species. It has obvious plant growth regulation activity, but is devoid of antifungal or antimicrobial activity. It is active against Plasmodium falciparum.
Specification
| Synonyms | (3R,5aS,10bR,11aS)-10b-(1,1-dimethyl-2-propen-1-yl)-6,10b,11,11a-tetrahydro-3-(2-methylpropyl)-2H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4(3H,5aH)-dione |
| Storage | Store at -20°C |
| IUPAC Name | (1S,4R,7S,9R)-9-(2-methylbut-3-en-2-yl)-4-(2-methylpropyl)-2,5,16-triazatetracyclo[7.7.0.02,7.010,15]hexadeca-10,12,14-triene-3,6-dione |
| Canonical SMILES | CC(C)CC1C(=O)N2C(CC3(C2NC4=CC=CC=C43)C(C)(C)C=C)C(=O)N1 |
| InChI | InChI=1S/C22H29N3O2/c1-6-21(4,5)22-12-17-18(26)23-16(11-13(2)3)19(27)25(17)20(22)24-15-10-8-7-9-14(15)22/h6-10,13,16-17,20,24H,1,11-12H2,2-5H3,(H,23,26)/t16-,17+,20+,22-/m1/s1 |
| InChI Key | HAXPBJUEOMQIJN-HBCLNWRISA-N |
| Source | Penicillium sp. |
Properties
| Appearance | Amorphous Powder |
| Antibiotic Activity Spectrum | Parasites |
| Boiling Point | 576.8±50.0°C at 760 mmHg |
| Melting Point | 79-82°C |
| Density | 1.2±0.1 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water |
Reference Reading
1. Diketopiperazine alkaloids from a deep ocean sediment derived fungus Penicillium sp
Tianjiao Zhu, Qianqun Gu, Lin Du, Hyun Park, Xinying Yang, Xiang Xiao, Fengping Wang Chem Pharm Bull (Tokyo) . 2009 Aug;57(8):873-6. doi: 10.1248/cpb.57.873.
Five new diketopiperazine alkaloids, brevicompanines D-H (3-7), together with two known analogs, allo-brevicompanine B (1) and fructigenine B (2), were isolated from a deep ocean sediment derived fungus Penicillium sp. Their structures were established by spectroscopic methods including 2D NMR and chiral HPLC analysis. Compounds 4 and 7 inhibited lipopolysaccharide (LPS)-induced nitric oxide production in BV2 microglial cells.
2. Ir-catalyzed reverse prenylation of 3-substituted indoles: total synthesis of (+)-aszonalenin and (-)-brevicompanine B
Erick M Carreira, Jonathan Ruchti J Am Chem Soc . 2014 Dec 3;136(48):16756-9. doi: 10.1021/ja509893s.
The selective reverse prenylation of 3-substituted-1H-indoles at C3 is described. The iridium-catalyzed reaction proceeds with high branched to linear selectivity (>20:1) for a variety of indoles. In addition, a diastereoselective reverse prenylation of tryptophan methyl ester is disclosed, and its synthetic utility is demonstrated in the synthesis of (+)-aszonalenin and (-)-brevicompanine B.
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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 ╳
