Carbazoquinocin C
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00488 |
| CAS | 155233-27-5 |
| Molecular Weight | 309.40 |
| Molecular Formula | C20H23NO2 |
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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 0.22 mmol/L.
Specification
| Synonyms | SCHEMBL13424600 |
| IUPAC Name | 1-heptyl-2-methyl-9H-carbazole-3,4-dione |
| Canonical SMILES | CCCCCCCC1=C(C(=O)C(=O)C2=C1NC3=CC=CC=C32)C |
| InChI | InChI=1S/C20H23NO2/c1-3-4-5-6-7-10-14-13(2)19(22)20(23)17-15-11-8-9-12-16(15)21-18(14)17/h8-9,11-12,21H,3-7,10H2,1-2H3 |
| InChI Key | XFGOIZUEQXLEAH-UHFFFAOYSA-N |
Properties
| Appearance | Dark Green Powder |
| Melting Point | 210-212 °C |
| Solubility | Soluble in Methanol |
Reference Reading
1. 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.
2. Total Syntheses of Carazostatin, Hyellazole, and Carbazoquinocins B-F
Tominari Choshi, Takuya Sada, Hiroyuki Fujimoto, Chizu Nagayama, Eiichi Sugino, Satoshi Hibino J Org Chem. 1997 Apr 18;62(8):2535-2543. doi: 10.1021/jo962038t.
Total syntheses of carazostatin (1), hyellazole (2a), and carbazoquinocins B-F (3b-f) have been completed. The cross-coupling reaction between 3-iodoindole 8 and vinylstannane 11b gave the 3-alkenylindole 7. Treatment of 7 with ethynylmagnesium bromide, followed by etherification of the resulting alcohol 12 with MOMCl, yielded the 3-alkenyl-2-propargylindole 6. The compound 6 was treated with t-BuOK in t-BuOH at 90 degrees C to obtain the desired carbazoles 4 together with the N-deprotected carbazole 13 through an allene-mediated electrocyclic reaction. The carbazole 13a, derived from 4a or 4c, was converted into the triflate 24 in two steps. The triflate 24 was subjected to the Suzuki cross-coupling reaction with either 9-heptyl-9-BBN or phenylboronic acid in the presence of a palladium catalyst to produce the 1-heptylcarbazole 25a and the 1-phenylcarbazole 25b. Cleavage of the ether bond of 25a yielded carazostatin (1). Cleavage of the ether bond of 25b followed by O-methylation gave hyellazole (2a). Oxidation of carazostatin (1) with benzene seleninic anhydride afforded carbazoquinocin C (3c). In a similar way, carbazoquinocins B and D-F (3b,d-f) were synthesized, respectively.
3. 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.
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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 ╳
