Carbazoquinocin D
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Enzyme inhibitors |
| Catalog number | BBF-00489 |
| CAS | 155233-28-6 |
| Molecular Weight | 323.43 |
| Molecular Formula | C21H25NO2 |
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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 0.37 mmol/L.
Specification
| IUPAC Name | 2-methyl-1-(5-methylheptyl)-9H-carbazole-3,4-dione |
| Canonical SMILES | CCC(C)CCCCC1=C(C(=O)C(=O)C2=C1NC3=CC=CC=C32)C |
| InChI | InChI=1S/C21H25NO2/c1-4-13(2)9-5-6-10-15-14(3)20(23)21(24)18-16-11-7-8-12-17(16)22-19(15)18/h7-8,11-13,22H,4-6,9-10H2,1-3H3 |
| InChI Key | KDTAIOIWWSESBU-UHFFFAOYSA-N |
Properties
| Appearance | Dark Green Powder |
| Melting Point | 208-210 °C |
| Solubility | Soluble in Methanol |
Reference Reading
1. 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.
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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 ╳
