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Usage

Uses

Used in Pharmaceutical Industry:
(S)-(1-(chloromethyl)-5-hydroxy-1H-benzo[e]indol-3(2H)-yl)(5,6,7-trimethoxy-1H-indol-2-yl)methanone is used as a potential pharmaceutical compound for its structural features that may allow it to interact with biological receptors or enzymes. The presence of a chloromethyl group and hydroxy group could facilitate its modification for specific targeting or activation purposes.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (S)-(1-(chloromethyl)-5-hydroxy-1H-benzo[e]indol-3(2H)-yl)(5,6,7-trimethoxy-1H-indol-2-yl)methanone is used as a starting material for the synthesis of novel drugs. Its unique structure may be exploited to design molecules with specific biological activities, such as agonists, antagonists, or inhibitors of certain targets.
Used in Drug Discovery:
(S)-(1-(chloromethyl)-5-hydroxy-1H-benzo[e]indol-3(2H)-yl)(5,6,7-trimethoxy-1H-indol-2-yl)methanone is used as a lead compound in drug discovery. Its structural complexity and the presence of multiple functional groups make it a promising candidate for the development of new therapeutic agents, particularly if its biological activity can be confirmed through further research.
Used in Chemical Synthesis:
This complex molecule can also be used as an intermediate in chemical synthesis, particularly for the production of other organic compounds with potential applications in various industries, including pharmaceuticals, materials science, and agrochemicals.

Upstream product

• 128781-07-7 5,6,7-trimethoxy-1H-indole-2-carboxylic acid 
• 1001016-30-3 C₃₀H₃₂ClN₃O₇ 
• 122745-41-9 tert-butyl (1S)-1-(chloromethyl)-5-hydroxy-1,2-dihydro-3H-benzo[e]indole-3-carboxylate 

Relevant academic research and scientific papers

CBI-TMI: Synthesis and evaluation of a key analog of the duocarmycins. Validation of a direct relationship between chemical solvolytic stability and cytotoxic potency and confirmation of the structural features responsible for the distinguishing behavior of enantiomeric pairs of agents

The synthesis of (+)- and ent-(-)-CBI-TMI (3), a key analog of the naturally occurring potent antitumor antibiotics duocarmycin SA (1) and duocarmycin A (2), is disclosed and was facilitated by the development of a general and direct chromatographic resolution of the advanced synthetic intermediate 13 on a preparative Diacel Chiralcel OD HPLC column. The DNA alkylation properties and the cytotoxic activity of (+)- and (-)-CBI-TMI (3) are detailed in conjunction with a comparative study of a key series of duocarmycin SA and A analogs. (+)-CBI-TMI proved to be an effective DNA alkylating agent which exhibited a selectivity and efficiency of DNA alkylation that are not distinguishable from those of (+)-duocarmycin SA (1), and it was found to be an exceptionally potent cytotoxic agent (IC50 = 30 pM, L1210). The comparative examination of the natural enantiomers of duocarmycin SA, duocarmycin A (2), CBI-TMI (3), and CI-TMI (4) revealed that the agents follow a predictable linear relationship between solvolytic chemical stability and cytotoxic activity which spans 3-4 orders of magnitude for the series of agents examined. In contrast, ent-(-)-CBI-TMI, unlike ent-(-)-duocarmycin SA, exhibited less effective DNA alkylation properties (100x) and it proved to be a relatively nonpotent cytotokic agent (100x). These latter observations are consistent with expectations based on recent models advanced which suggest that the distinguishing behavior of such unnatural enantiomers is the result of destabilizing steric interactions surrounding the duocarmycin C7 center.

SELENOPHENE-FUSED AROMATIC COMPOUND AND MANUFACTURING METHOD THEREOF

The present disclosure relates to a method for more easily and economically producing a selenophene-fused aromatic compound derivative containing various substituents and the selenophene-fused aromatic compound produced according to the method, and the selenophene-fused aromatic compound can be used for various purposes such as an intermediate of an anti-bacterial or anticancer substance, an indicator of which color is changed depending on a solvent, or a fluorescent substance.

CBI DERIVATIVES SUBJECT TO REDUCTIVE ACTIVATION

A unique class of N-acyl O-amino phenol prodrugs of CBI-TMI and CBI-indole2 were synthesized and shown to be prodrugs, subject to reductive activation by nucleophilic cleavage of a weak N-O bond, effectively releasing the free drug in functional cellular assays for cytotoxic activity approaching or matching the activity of the free drug, yet remain essentially stable to ex vivo DNA alkylation conditions. Most impressively, assessment of the in vivo antitumor activity of a representative O- (acylamino) prodrug, 8, indicate that they approach the potency and exceed the efficacy of the free drug itself (CBI-indole2), indicating that the inactive prodrugs not only effectively release the free drug in vivo, but that they offer additional advantages related to a controlled or targeted release in vivo.

Unsymmetrical DNA cross-linking agents: Combination of the CBI and PBD pharmacophores

A set of 10 compounds, each combining the seco-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one (seco-CBI) and pyrrolo [2,1-c] [1,4] benzodiazepine (PBD) pharmacophores, was designed and prepared. These compounds were anticipated to cross-link between N3 of adenine and N2 of guanine in the minor groove of DNA. The compounds, which differ in the chain length separating the two alkylation subunits, and the configuration of the CBI portion, showed great variation in cellular toxicity (over 4 orders of magnitude in a cell line panel) with the most potent example exhibiting IC50S in the pM range. Cytotoxicity correlated with the ability of the compounds to cross-link naked DNA. Cross-linking was also observed in living cells, at much lower concentrations than for a related symmetrical PBD dimer. A thermal cleavage assay was used to assess sequence selectivity, demonstrating that the CBI portion controlled the alkylation sites, while the PBD substituent increased the overall efficiency of alkylation. Several compounds were tested for in vivo activity using a tumor growth delay assay against WiDr human colon carcinoma xenografts, with one compound (the most cytotoxic and most efficient cross-linker) showing a statistically significant increase in survival time following a single iv dose.