157922-77-5

Basic information

• Product Name: (S)-(1-(chloromethyl)-5-hydroxy-1H-benzo[e]indol-3(2H)-yl)(5,6,7-trimethoxy-1H-indol-2-yl)methanone
• CAS NO: 157922-77-5
• Molecular Weight: 466.921
• Mol File: 157922-77-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 711.7±60.0 °C(Predicted)
• Density: 1.389±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (S)-(1-(chloromethyl)-5-hydroxy-1H-benzo[e]indol-3(2H)-yl)(5,6,7-trimethoxy-1H-indol-2-yl)methanone(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(1-(chloromethyl)-5-hydroxy-1H-benzo[e]indol-3(2H)-yl)(5,6,7-trimethoxy-1H-indol-2-yl)methanone(157922-77-5)
• EPA Substance Registry System: (S)-(1-(chloromethyl)-5-hydroxy-1H-benzo[e]indol-3(2H)-yl)(5,6,7-trimethoxy-1H-indol-2-yl)methanone(157922-77-5)

Safety Data

• Hazardous Substances Data: 157922-77-5(Hazardous Substances Data)

Usage

Description

(S)-(1-(chloromethyl)-5-hydroxy-1H-benzo[e]indol-3(2H)-yl)(5,6,7-trimethoxy-1H-indol-2-yl)methanone is a complex organic molecule characterized by its unique structural features. It incorporates a chloromethyl group, a hydroxy group, and multiple methoxy groups, along with an indol-2-yl and benzo[e]indol-3(2H)-yl moiety. These structural elements suggest potential interactions with biological receptors or enzymes, indicating possible pharmaceutical or medicinal applications. However, further research and analysis are required to fully comprehend the properties and potential uses of this molecule.

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

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

Relevant articles and documents

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.

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.