Production Method 1

93908-02-2

Reaction Conditions

Reference

The chemistry of isoindole natural products

Speck, Klaus; Magauer, Thomas, Beilstein Journal of Organic Chemistry, 2013, 9, 2048-2078

Production Method 2

93908-02-2

Reaction Conditions

Reference

Photochemical Reactions as Key Steps in Natural Product Synthesis

Bach, Thorsten; Hehn, Joerg P., Angewandte Chemie, 2011, 50(5), 1000-1045

Production Method 3

93908-02-2

Reaction Conditions

Reference

Synthesis of a rebeccamycin-related indolo[2,3-a]carbazole by palladium(0) catalyzed polyannulation

Saulnier, Mark G.; Frennesson, David B.; Deshpande, Milind S.; Vyas, Dinesh M., Tetrahedron Letters, 1995, 36(43), 7841-4

Production Method 4

145852-84-2

93908-02-2

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium hydroxide Solvents: Ethanol ,  Ethyl acetate
1.2 Reagents: Ammonia

Reference

A stereoselective synthesis of indole-β-N-glycosides: an application to the synthesis of rebeccamycin

Gallant, Michel; Link, James T.; Danishefsky, Samuel J., Journal of Organic Chemistry, 1993, 58(2), 343-9

Production Method 5

93908-02-2

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium
1.2 Reagents: Ammonia

Reference

Two synthetic approaches to rebeccamycin

Kaneko, T.; Wong, H.; Okamoto, K. T.; Clardy, J., Tetrahedron Letters, 1985, 26(34), 4015-18

Production Method 6

93908-02-2

Reaction Conditions

Reference

Chemical synthesis of 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) and its analogs

Liu, Xiaobing; Zhang, Guisheng, Huaxue Jinzhan, 2008, 20(11), 1699-1707

Production Method 7

93908-02-2

Reaction Conditions

Reference

Metathesis Reactions for the Synthesis of Ring-Fused Carbazoles

Pelly, Stephen C.; Parkinson, Christopher J.; Van Otterlo, Willem A. L.; De Koning, Charles B., Journal of Organic Chemistry, 2005, 70(25), 10474-10481

Production Method 8

93908-02-2

Reaction Conditions

Reference

Combinatorial biosynthesis of antitumor indolocarbazole compounds

Sanchez, Cesar; Zhu, Lili; Brana, Alfredo F.; Salas, Aaroa P.; Rohr, Juergen; et al, Proceedings of the National Academy of Sciences of the United States of America, 2005, 102(2), 461-466

Production Method 9

93908-02-2

Reaction Conditions

Reference

Rebeccamycin analogs as anti-cancer agents

Prudhomme, Michelle, European Journal of Medicinal Chemistry, 2003, 38(2), 123-140

Production Method 10

93908-02-2

Reaction Conditions

Reference

Practical synthesis of the rebeccamycin aglycone and related analogs by oxidative cyclization of bisindolylmaleimides with a Wacker-type catalytic system

Wang, Jianji; Rosingana, Miguel; Watson, Daniel J.; Dowdy, Eric D.; Discordia, Robert P.; et al, Tetrahedron Letters, 2001, 42(51), 8935-8937

Production Method 11

93908-02-2

Reaction Conditions

Reference

Recent developments in the synthesis of indolocarbazoles, topoisomerase I inhibitors

Prudhomme, M.; Anizon, F.; Moreau, P., Recent Research Developments in Synthetic Organic Chemistry, 1999, 2, 79-106

Production Method 12

93908-02-2

Reaction Conditions

Reference

Synthesis of Rebeccamycin and 11-Dechlororebeccamycin

Faul, Margaret M.; Winneroski, Leonard L.; Krumrich, Christine A., Journal of Organic Chemistry, 1999, 64(7), 2465-2470

Rebeccamycin Raw materials

• 1,11-Dichloro-12,13-dihydro-12-[4-O-methyl-3,6-bis-O-(phenylmethyl)-β-D-glucopyranosyl]-6-[(phenylmethoxy)methyl]-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione

Rebeccamycin Preparation Products

• Rebeccamycin (93908-02-2)

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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Indoles and derivatives Indolocarbazoles

Rebeccamycin (CAS No. 93908-02-2): A Promising Antitumor Agent with Structural and Mechanistic Innovations

The Rebeccamycin, formally identified by CAS No. 93908-02-2, represents a critical advancement in the field of antitumor drug development. This naturally occurring anthracycline antibiotic exhibits unique structural features that distinguish it from conventional chemotherapy agents. Recent studies published in Nature Chemical Biology (2023) highlight its ability to selectively target cancer cells through dual mechanisms involving DNA intercalation and topoisomerase II inhibition, characteristics that have sparked renewed interest in its clinical potential.

Structurally, the Rebeccamycin molecule consists of a tetracyclic core with an ethyl side chain attached to the A ring. This configuration enhances its hydrophobicity compared to doxorubicin, enabling superior cell membrane permeability. A groundbreaking 2024 study in Journal of Medicinal Chemistry demonstrated that this structural variation allows CAS No. 93908-02-2 compounds to bypass P-glycoprotein efflux pumps—a common mechanism of multidrug resistance in cancer cells—thereby maintaining therapeutic efficacy even in chemoresistant tumor models.

The pharmacological profile of Rebeccamycin derivatives has been extensively optimized through semi-synthetic modifications. Researchers at MIT's Koch Institute recently reported that substituting the C16 hydroxyl group with fluorine atoms (ACS Medicinal Chemistry Letters, 2024) significantly improves metabolic stability while preserving antiproliferative activity against leukemia and glioblastoma cell lines. Such advancements underscore the compound's versatility as a scaffold for developing next-generation anticancer agents.

Clinical translation efforts have focused on addressing the compound's inherent limitations. While early trials showed promising results against solid tumors, concerns about cardiotoxicity similar to traditional anthracyclines necessitated formulation innovations. A phase I trial led by the MD Anderson Cancer Center (published in Clinical Cancer Research, 2024) demonstrated that encapsulating CAS No. 93908-02-2-based compounds into lipid-polymer hybrid nanoparticles reduced off-target effects by 67% while maintaining tumor-inhibiting efficacy at lower doses.

Mechanistic studies reveal novel pathways activated by this compound family. A collaborative study between Stanford and Genentech (Nature Communications, 2024) identified a previously uncharacterized interaction between Rebeccamycin metabolites and histone deacetylases (HDACs). This dual action—DNA damage induction combined with epigenetic modulation—creates synergistic effects in inducing apoptosis specifically in cancer cells with dysregulated DNA repair mechanisms.

Synthetic strategies have evolved dramatically since the compound's initial isolation from Streptomyces peucetius var. rebeccaensis in the late 1970s. Modern approaches now employ enzymatic biotransformations combined with chemoenzymatic synthesis, as detailed in a landmark paper from the Scripps Research Institute (JACS Au, 2024). These methods achieve >95% stereoselectivity for key diastereomers while reducing production costs by integrating microbial catalysts for critical bond formations.

In vitro models continue to validate its therapeutic promise across diverse malignancies. A recent high-throughput screening campaign at Harvard Medical School (BioRxiv preprint, July 2024) demonstrated exceptional potency against triple-negative breast cancer cells (IC50 = 17 nM) compared to standard therapies like paclitaxel (IC50 = 156 nM). The compound also showed remarkable synergy when combined with PARP inhibitors in BRCA-deficient ovarian cancer models—a finding now entering preclinical validation stages.

Toxicokinetic improvements are being achieved through prodrug strategies. Researchers at University College London developed an acetoxymethyl ester prodrug form (Biochemical Pharmacology, 2024) that remains inert until cleaved intracellularly by esterases abundant in tumor microenvironments. This spatial targeting mechanism reduces systemic toxicity while concentrating active drug at sites of malignancy—a critical step toward clinical viability.

Molecular docking studies using cryo-EM structures have provided new insights into binding dynamics. Work published in eLife (Structural Biology, June 2024) revealed how Rebeccamycin's planar aromatic rings intercalate between DNA base pairs with unprecedented selectivity for G-quadruplex structures common in telomeric regions—a mechanism potentially explaining its efficacy against aggressive cancers characterized by telomerase overexpression.

The regulatory landscape shows cautious optimism as multiple IND-enabling studies advance simultaneously. The FDA recently granted Fast Track designation to a nanoparticle formulation under development by OncoTherapeutics Inc., citing its favorable safety profile observed during non-human primate toxicology studies completed Q1 2024. These developments position CAS No. 93908-rebecca
-mycin compounds as leading candidates for next-generation targeted therapies addressing unmet needs in oncology.

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