93908-02-2

Basic information

• Product Name: REBECCAMYCIN
• Synonyms: 5h-indolo(2,3-a)pyrrolo(3,4-c)carbazole-5,7(6h)-dione,1,11-dichloro-12,13-dihy;dro-12-(4-o-methyl-beta-d-glucopyranosyl)-;REBECCAMYCIN;REBECCAMYCIN, SACCHAROTHRIX AEROCOLONIGENES;1,11-Dichloro-12,13-dihydro-12-(4-O-methyl-β-D-glucopyranosyl)-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione;NSC 359079;7,10-Dichloro-8-(3,4-dihydroxy-6-(hydroxymethyl)-5-methoxytetrahydro-2H-pyran-2-yl)-8,9-dihydro-1H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-1,3(2H)-dione
• CAS NO: 93908-02-2
• Molecular Formula: C₂₇H₂₁Cl₂N₃O₇
• Molecular Weight: 570.38
• Mol File: 93908-02-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: yellow/solid
• Density: 1.87g/cm³
• Refractive Index: 1.844
• Storage Temp.: −20°C
• Solubility: DMSO: ≥3 mg/mL
• CAS DataBase Reference: REBECCAMYCIN(CAS DataBase Reference)
• NIST Chemistry Reference: REBECCAMYCIN(93908-02-2)
• EPA Substance Registry System: REBECCAMYCIN(93908-02-2)

Safety Data

• Hazardous Substances Data: 93908-02-2(Hazardous Substances Data)

Usage

Description

Rebeccamycin, an indolocarbazole alkaloid, is a naturally occurring compound isolated from the bacterium Lechevalieria aerocolonigenes. It exhibits selective antitumor activity against various cancer cell lines and is known for its potent catalytic inhibition of both topoisomerases I and II through strong DNA intercalation. REBECCAMYCIN has garnered significant interest in the field of cancer therapy, with its analogues being tested in clinical trials.

Uses

Used in Pharmaceutical Industry:
Rebeccamycin is utilized as a novel topoisomerase I inhibitor for its cancer therapeutic applications. Its primary mechanism of action involves the strong intercalation of DNA, leading to the potent inhibition of both topoisomerases I and II. This action results in the suppression of tumor growth and the selective targeting of cancer cells.
Additionally, rebeccamycin and its analogues are being tested in clinical trials for their potential use in cancer therapy. These trials aim to evaluate the safety, efficacy, and optimal dosages of rebeccamycin-based treatments for various types of cancer. The development of rebeccamycin as a cancer therapeutic agent holds promise for the advancement of targeted cancer treatments and the improvement of patient outcomes.

InChI:InChI=1/C27H21Cl2N3O7/c1-38-24-13(8-33)39-27(23(35)22(24)34)32-20-10(5-3-7-12(20)29)15-17-16(25(36)31-26(17)37)14-9-4-2-6-11(28)18(9)30-19(14)21(15)32/h2-7,13,22-24,27,30,33-35H,8H2,1H3,(H,31,36,37)/t13-,22-,23-,24-,27-/m1/s1

Upstream product

• 102147-55-7 C₄₁H₃₅Cl₂N₃O₁₁ 
• 502498-34-2 1-bromo-2,3,6-tri-O-acetyl-4-O-methylglucose 
• 102147-53-5 1,11-dichloro-12,13-dihydro-6-[(phenylmethoxy)methyl]-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione 

Downstream Products

• 215796-54-6 1,11-dichloro-12[4-O-methyl-β-D-(2'-O-tosyl)glucopyranosyl]-6,7,12,13-tetrahydro(5H)-indolo[2,3-a]-pyrrolo[3,4-c]-carbazole-5,7-dione 

Relevant articles and documents

Synthesis of rebeccamycin and 11-dechlororebeccamycin

Glycosylated 7-chloroindole-3-acetamide 9, prepared in four steps and 26% yield from 7-chloroindole (1), was condensed with methyl 7-chloroindole- 3-glyoxylate 11 and methyl indole-3-glyoxylate 12 to provide bisindolylmaleimides 7 and 8 in 86% and 84% yield, respectively. Oxidation of 7 and 8 followed by debenzylation provided a new approach to the synthesis of rebeccamycin and completed for the first time a synthesis of 11- dechlororebeccamycin.

Two synthetic approaches to rebeccamycin

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