CAS 93908-02-2

(+)-Rebeccamycin

Description:

(+)-Rebeccamycin is a naturally occurring indolocarbazole alkaloid that exhibits notable biological activity, particularly as an antitumor agent. It is derived from the bacterium *Nocardia hygroscopicus* and is characterized by its complex polycyclic structure, which includes a fused indole and carbazole moiety. The compound has demonstrated the ability to inhibit topoisomerase I, an enzyme crucial for DNA replication and transcription, thereby interfering with cancer cell proliferation. (+)-Rebeccamycin is also known for its potential antimicrobial properties. In terms of solubility, it is typically more soluble in organic solvents than in water, which can influence its bioavailability and therapeutic application. The stereochemistry of (+)-Rebeccamycin contributes to its biological activity, with the specific configuration playing a role in its interaction with biological targets. Overall, this compound is of significant interest in medicinal chemistry and pharmacology due to its unique structure and promising therapeutic potential.

Formula: C₂₇H₂₁Cl₂N₃O₇

InChI: InChI=1S/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

InChI key: InChIKey=QEHOIJJIZXRMAN-QZQSLCQPSA-N

SMILES: O=C1C2=C3C(N(C=4C3=CC=CC4Cl)[C@@H]5O[C@H](CO)[C@@H](OC)[C@H](O)[C@H]5O)=C6C(=C2C(=O)N1)C=7C(N6)=C(Cl)C=CC7

Synonyms:

• 1,11-Dichloro-12,13-dihydro-12-(4-O-methyl-β-<span class="text-smallcaps">D</span>-glucopyranosyl)-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione
• 1,11-dichloro-12-(4-O-methyl-beta-D-glucopyranosyl)-12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione
• 1,11-dichloro-12-(4-O-methylhexopyranosyl)-12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione
• 5H-Indolo(2,3-a)pyrrolo(3,4-c)carbazole-5,7(6H)-dione, 1,11-dichloro-12,13-dihydro-12-(4-O-methyl-beta-D-glucopyranosyl)-
• 5H-Indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione, 1,11-dichloro-12,13-dihydro-12-(4-O-methyl-β-<span class="text-smallcaps">D</span>-glucopyranosyl)-
• Brn 4732638
• Nsc 359079
• Rebeccamycin
• 5H-Indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione, 1,11-dichloro-12,13-dihydro-12-(4-O-methyl-β-D-glucopyranosyl)-
• 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

Rebeccamycin

CAS: 93908-02-2

Rebeccamycin: an antitumor antibiotic; targets DNA topoisomerase I; minor effect on kinase C and topo II.

Formula: C₂₇H₂₁Cl₂N₃O₇

Purity: 98%

Color and Shape: Solid

Molecular weight: 570.38

Ref: TM-T16726

Rebeccamycin solid

CAS: 93908-02-2

Formula: C₂₇H₂₁Cl₂N₃O₇

Molecular weight: 570.4

Ref: 7W-GA2054

Rebeccamycin

Controlled Product

CAS: 93908-02-2

Formula: C₂₇H₂₁Cl₂N₃O₇

Color and Shape: Neat

Molecular weight: 570.378

Ref: TR-R140000