Carbazoquinocin D

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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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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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