75139-39-8

Usage

Uses

Used in Pharmaceutical Industry:
Carbazomycin A is used as an antimalarial agent for its ability to effectively combat malaria-causing parasites. It is particularly useful in areas where traditional antimalarial drugs have become less effective due to resistance.
Additionally, carbazomycin A is used as an antituberculosis agent, targeting and inhibiting the growth of Mycobacterium tuberculosis, the bacteria responsible for tuberculosis. Its effectiveness in treating drug-resistant strains of tuberculosis makes it a promising candidate for further research and development in the fight against this disease.
Used in Biological Studies:
In the field of biological research, carbazomycin A serves as a valuable tool for studying the mechanisms of action against malaria and tuberculosis. Its isolation from Streptomyces provides insights into the natural sources of potent antimicrobial compounds and their potential applications in medicine.

InChI:InChI=1/C16H17NO2/c1-9-10(2)15(18-3)16(19-4)13-11-7-5-6-8-12(11)17-14(9)13/h5-8,17H,1-4H3

Upstream product

• 67-56-1 methanol 
• 123719-43-7 tert-butyl 4-bromo-3-methoxy-1,2-dimethyl-9H-carbazole-9-carboxylate 
• 10511-51-0 1-Benzylindole-3-carboxaldehyde 
• 76306-35-9 3-methoxy-1,2-dimethyl-9H-carbazole 
• 118538-97-9 3-hydroxy-1,2-dimethyl-9H-carbazole 
• 147623-19-6 2-methoxy-3,4-dimethyl-5-nitrophenyl acetate 
• 118538-99-1 2-methoxy-3,4-dimethyl-5-nitrophenol 
• 100132-28-3 4,5-dimethoxy-2,3-dimethylaniline 
• 153709-76-3 1,2-dimethoxy-3,4-dimethyl-5-nitrobenzene 
• 248252-69-9 1,2-dimethoxy-3,4-dimethylbenzene 
• 74866-17-4 3,4-dimethoxy-2-methyl-1-bromobenzene 
• 4463-33-6 1,2-dimethoxy-3-methylbenzene 

Relevant academic research and scientific papers

Cascade Benzannulation Approach for the Syntheses of Lipocarbazoles, Carbazomycins, and Related Alkaloids

Herein, a state-of-the-art one-pot cascade benzannulation technique for the efficacious synthesis of valuable 3-hydroxy-2-methyl carbazoles, a linchpin of more than 25 carbazole-based alkaloids, is unveiled from readily affordable fundamental commodities. The key step of this strategy is gaining aromaticity by site-selective elimination of hydroxyl group controlled by nucleophilicity of the indole ring. The present strategy shows excellent functional group tolerance with a broad substrate scope. The utility of this convenient approach was appealingly exemplified via concise total syntheses of 10 carbazole-based alkaloids possessing significant biological activities and thus of medicinal importance.

INDOLE-YNONE MEDIATED BENZOANNULATION PROCESS FOR THE PREPARATION OF CARBAZOLES- CARBAZOMYCIN A, CALOTHRIXIN B AND STAUROSPORINONE

The present invention relates to carbazoles of general formula (I), and process for the preparation thereof: wherein 'R1' is H, C1-C6 alkyl, benzyl, or allyl; R2 is H, C1-C6 alkyl, cyclopropyl, phenyl, aryl, heteroaryl, or NO2; R3 is H, C1-C6 alkyl, cyclopropyl, phenyl aryl, heteroaryl, 4-methoxy phenyl, 4-ethyl phenyl, 2-methyl phenyl, or 2-Fluoro phenyl; R4 is H, benzoyl, -CO2Et, -CHO, Br, or -OMe; R5 is OH, OMOM, OMe, CN, or OTf; R6 is H, or O-alkyl; and R3-R4 is -CHNCH2CH2-. This invention also relates to the process for the preparation of carbazomycin A of Formula (1), calothrixin B of Formula (2) and staurosporinone of Formula (3) involving carbazoles of general formula (I) as an intermediate.

A General Carbazole Synthesis via Stitching of Indole-Ynones with Nitromethanes: Application to Total Synthesis of Carbazomycin A, Calothrixin B, and Staurosporinone

A new, one-pot domino benzannulation reaction between indole-3-ynones and various nitromethane derivatives has been explored for a general entry to diversely functionalized carbazole frameworks (28 examples). The scope of this new benzannulation has been

Total synthesis of carbazomycins A and B

Total syntheses of carbazomycins A and B were demonstrated using a ytterbium-catalyzed Diels-Alder reaction with (silyloxyvinyl)indole as a diene. The densely substituted benzene ring of the target compound was successfully constructed by functionalization of a hydrocarbazolone intermediate and subsequent aromatization using N-bromosuccinimide.

A direct palladium-catalyzed route to selectively substituted carbazoles through sequential C-C and C-N bond formation: Synthesis of carbazomycin A

The present paper offers a synthetically simple one-pot procedure for the catalytic preparation of the biologically interesting class of carbazoles. The new procedure is based on the combined catalysis of palladium and norbornene starting from o-substituted iodoarenes and N-sulfonylated or N-acetylated o-bromoanilines. A well-known member of this class, carbazomycin A, has been successfully prepared.

Transition metal complexes in organic synthesis, part 54.1 Improved total syntheses of the antibiotic alkaloids carbazomycin A and B

Considerably improved total syntheses of the carbazole antibiotics carbazomycin A and B are reported using a convergent iron-mediated one-pot construction of the carbazole framework by oxidative cyclization in the air.

Synthesis of the Carbazole Alkaloids Carbazomycin A and B and Hyellazole

The first synthesis of carbazomycins A and B (1) is described; the route involves Diels-Alder reaction of 1-methylpyranoindol-3-one with ethyl 3-trimethylsilylpropynoate followed by functional group interconversions; the marine alkaloid hyellazole