Fluoroindolocarbazole B

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Category Antibiotics
Catalog number BBF-01419
CAS
Molecular Weight 523.44
Molecular Formula C26H19F2N3O7

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Description

Fluoroindolocarbazole B is produced by the strain of Saccharothrothrix aerocolonigenes. Fluoroindolocarbazole B has antitumor effect.

Specification

Synonyms 2,10-Difluoro-12,13-dihydro-12-[-D-glucopyranosyl]-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione
IUPAC Name 6,20-difluoro-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4(9),5,7,10,15,17(22),18,20-nonaene-12,14-dione
Canonical SMILES C1=CC2=C(C=C1F)NC3=C4C(=C5C(=C23)C(=O)NC5=O)C6=C(N4C7C(C(C(C(O7)CO)O)O)O)C=C(C=C6)F
InChI InChI=1S/C26H19F2N3O7/c27-8-1-3-10-12(5-8)29-19-15(10)17-18(25(37)30-24(17)36)16-11-4-2-9(28)6-13(11)31(20(16)19)26-23(35)22(34)21(33)14(7-32)38-26/h1-6,14,21-23,26,29,32-35H,7H2,(H,30,36,37)/t14-,21-,22+,23-,26-/m1/s1
InChI Key NKNQTGRKBYNURK-QCUUGYDUSA-N

Properties

Appearance Light Yellow Solid
Antibiotic Activity Spectrum neoplastics (Tumor)

Reference Reading

1. Production, isolation and structure determination of novel fluoroindolocarbazoles from Saccharothrix aerocolonigenes ATCC 39243
K S Lam, D R Schroeder, J M Veitch, K L Colson, J A Matson, W C Rose, T W Doyle, S Forenza J Antibiot (Tokyo). 2001 Jan;54(1):1-9. doi: 10.7164/antibiotics.54.1.
Saccharothrix aerocolonigenes ATCC 39243 produces an indolocarbazole antitumor agent rebeccamycin under submerged fermentation conditions. Adding DL-6-fluorotryptophan to culture of S. aerocolonigenes ATCC 39243 induces the formation of two novel indolocarbazoles, fluoroindolocarbazoles A and B. Feeding DL-5-fluorotryptophan to culture of S. aerocolonigenes ATCC 39243 induces the production of a novel indolocarbazole, fluoroindolocarbazole C. These fluoroindolocarbazoles have been isolated from culture broth and purified to homogeneity by vacuum liquid chromatography and column chromatography. All three fluoroindolocarbazoles are more potent than rebeccamycin against P388 leukemia by ip route in murine model.

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