174402-48-3

Upstream product

• 4291-68-3 1-chloro-2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 174402-52-9 2,10-dibenzyloxy-12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-6-methyl-5,7-(6H)-dione 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 174402-47-2 3-(6-Benzyloxy-1H-indol-3-yl)-4-[6-benzyloxy-1-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-1H-indol-3-yl]-1-methyl-pyrrole-2,5-dione 

Downstream Products

• 1392193-72-4 6-(2,6-dihydroxycyclohexylamino)-2,10-dihydroxy-12-β-D-glucopyranosyl-12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione 
• 357401-16-2 12,13-dihydro-2,10-dibenzyloxy-6-N-(1-benzyloxymethyl-2-benzyloxyethylamino)-13-(β-D-2,3,4,6-tetra-O-benzylglucopyranosyl)-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione 
• 357401-10-6 12,13-dihydro-2,10-dibenzyloxy-13-(β-D-2,3,4,6-tetra-O-benzylglucopyranosyl)-5H-indolo[2,3-a]carbazole-5,6-dicarboxylic acid anhydride 

Relevant academic research and scientific papers

Synthesis and biological evaluation of rebeccamycin analogues modified at the imide moiety

Glycosylated indolocarbazoles related to the antibiotic rebeccamycin represent an important class of antitumour drugs. In the course of our structure-activity relationship studies, new rebeccamycin analogues modified at the imide moiety were synthesised. The antiproliferative activity of the compounds was evaluated on three human cancer cell lines, A2780 (ovarian cancer), H460 (lung cancer), and GLC4 (small-cell lung cancer). The in vitro cytotoxicity of compounds 2 and 4, characterised respectively by a 1,3-dioxolan and (1,3-dioxolan-4-yl)methylene groups linked to the imide moiety, was higher than the reference compound, edotecarin. The effect of compound 2 in inducing tumour regression in the A2780 xenograft model was also investigated.

PROCESS FOR PRODUCING INDOLOPYRROLOCARBAZOLE DERIVATIVE

The present invention relates to an industrially preferable process for producing an indolopyrrolocarbazole derivative represented by the formula (I): or a pharmaceutically acceptable salt thereof, which is useful as an anti-cancer agent. The above proce

Processes for the preparation of indolopyrrolocarbazole derivatives

This invention relates to processes for the preparation of intermediates which are useful in the synthesis of compounds of the general formula or pharmaceutically salts thereof, wherein R1 and R2 each represent an OH group, R1/

Practical synthesis of a potent indolocarbazole-based, DNA topoisomerase inhibitor

DNA topoisomerase I inhibitors are currently under investigation as cancer chemotherapy agents of which indolocarbazole glycoside (1) has been identified as a promising candidate. A practical, scalable synthesis of 1 that limits the isolation of cytotoxic compounds to only that of the final product is described. The convergent process features a novel phase transfer-promoted glycosylation of aglycone core (4); subsequent hydrolysis provides anhydride (8). The hydrazine fragment (3), which is coupled with 8, is synthesized via a modification of existing procedures. The coupled product (2) is subsequently hydrogenated to provide 1 in excellent purity via direct crystallization (>99.3 A%).

Synthesis and biological activities of NB-506 analogues modified at the glucose group

A new indolocarbazole compound, NB-506 (1), modified at the glucose group yielded a β-D-glucopyranoside, J-107,088 (2), which showed potent anticancer activity. A β-D-ribofuranoside, J-109,534 (3), was found to be 6 times more potent than J-107,088 at inhibiting topoisomerase I. (C) 2000 Elsevier Science Ltd. All rights reserved.

Synthesis and biological activities of NB-506 analogues: Effects of the positions of two hydroxyl groups at the indole rings

In the course of a study of 6-N-amino-substituted analogues of NB-506 (1), a more potent anticancer drag, J-109,404 (2), in which the formyl group of NB-506 was replaced with a 1,3-dihydroxypropane group, was reported. A study of further modification in the positions of two hydroxyl groups at the indole rings of 2 resulted in the discovery of a 2,10-dihydroxy analogue, J- 107,088 (3), which is a promising anticancer agent with a broader therapeutic window than J-109,404.

Synthesis of dissymmetric indolocarbazole glycosides using the Mitsunobu reaction at the glycosylation step

A novel method for the synthesis of N-glycosylated dissymmetric indolo[2,3-a]pyrrolo-[3,4-c]carbazole derivatives was developed by applying the Mitsunobu reaction to the N-glycosylation reaction of substituted indole substrates.