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Fluoroindolocarbazole B

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

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Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

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

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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
Appearance Light Yellow Solid
Antibiotic Activity Spectrum neoplastics (Tumor)
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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