Carbazoquinocin A
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Enzyme inhibitors |
| Catalog number | BBF-00486 |
| CAS | 164322-78-5 |
| Molecular Weight | 295.37 |
| Molecular Formula | C19H21NO2 |
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Description
It is produced by the strain of Streptomyces violaceus 2448-SVT2. It acts as an antioxidant and GMP phosphodiesterase inhibitor. IC50 is 0.41 mmol/L.
Specification
| IUPAC Name | 2-methyl-1-(3-methylpentyl)-9H-carbazole-3,4-dione |
| Canonical SMILES | CCC(C)CCC1=C(C(=O)C(=O)C2=C1NC3=CC=CC=C32)C |
| InChI | InChI=1S/C19H21NO2/c1-4-11(2)9-10-13-12(3)18(21)19(22)16-14-7-5-6-8-15(14)20-17(13)16/h5-8,11,20H,4,9-10H2,1-3H3 |
| InChI Key | HRRLXMQMBJABIM-UHFFFAOYSA-N |
Properties
| Appearance | Dark Green Powder |
| Melting Point | 210-212 °C |
Reference Reading
1. Total synthesis of carbazoquinocin C: application of the o-benzannulation of Fischer carbene complexes to carbazole-3,4-quinone alkaloids
Manish Rawat, William D Wulff Org Lett. 2004 Feb 5;6(3):329-32. doi: 10.1021/ol0360445.
[reaction: see text] The photoinduced o-benzannulation of 3-(2-vinyl)indolylcarbene complexes provides a direct route to carbazole derivatives that are oxygenated in the 3- and 4-positions. This reaction is quite efficient and provides for a unique synthesis of the lipid peroxidation inhibitor carbazoquinocin C.
2. An approach to functionalized carbazoles from Z-enoate propargylic alcohols. A unified total synthesis of N-Me-carazostatin, N-Me-carbazoquinocin C and N-Me-lipocarbazole A4
Debayan Roy, Prabhakararao Tharra, Beeraiah Baire Chem Commun (Camb). 2022 Sep 13;58(73):10210-10213. doi: 10.1039/d2cc03526j.
Development of an acid catalyzed, intramolecular benzannulation of indoles for the synthesis of functionalized carbazoles has been reported. The indole appended Z-enoate propargylic alcohols have been employed. The N-EDG-indoles involve the 5-exo-dig cyclization followed by 1,2-migration to give the carbazole-butenoates, whereas the N-EWG-indoles undergo the Z-enoate assisted Meyer-Schuster rearrangement to give the dihydrocarbazole-4-oxo-butanoates. Utilizing one of the 2-methyl-carbazole-butyraldehyde (obtained from the corresponding carbazole-butanoate) as the key intermediate, we have developed a simple approach for an efficient synthesis of N-Me-carazostatin, N-Me-carbazoquinocin C and N-Me-lipocarbazole A4.
3. Metabolomic Comparison and Assessment of Co-cultivation and a Heat-Killed Inducer Strategy in Activation of Cryptic Biosynthetic Pathways
Libang Liang, Guanqiao Wang, Bradley Haltli, Douglas H Marchbank, Henrik Stryhn, Hebelin Correa, Russell G Kerr J Nat Prod. 2020 Sep 25;83(9):2696-2705. doi: 10.1021/acs.jnatprod.0c00621. Epub 2020 Sep 1.
Co-cultivation has been used as a promising tool to turn on or up-regulate cryptic biosynthetic pathways for microbial natural product discovery. Recently, a modified culturing strategy similar to co-cultivation was investigated, where heat-killed inducer cultures were supplemented to the culture medium of producer fermentations to induce cryptic pathways. In the present study, the repeatability and effectiveness of both methods in turning on cryptic biosynthetic pathways were unbiasedly assessed using UHPLC-HRESIMS-based metabolomics analysis. Both induction methods had good repeatability, and they resulted in very different induced metabolites from the tested producers. Co-cultivation generated more induced mass features than the heat-killed inducer cultures, while both methods resulted in the induction of mass features not observed using the other induction method. As examples, pathways leading to two new natural products, N-carbamoyl-2-hydroxy-3-methoxybenzamide (1) and carbazoquinocin G (5), were induced and up-regulated through co-culturing a producer Streptomyces sp. RKND-216 with inducers Alteromonas sp. RKMC-009 and M. smegmatis ATCC 120515, respectively.
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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 ╳
