454713-41-8

Usage

Uses

Used in Pharmaceutical Industry:
N-Boc-1-chloromethyl-1,2-dihydro-3H-benzo[e]indole is used as a synthetic intermediate for the preparation of benzindole and benzoquinoline derivatives. These derivatives are further utilized as prodrugs for tumor treatment, offering potential therapeutic benefits in the management of various types of cancer.
In the pharmaceutical industry, N-Boc-1-chloromethyl-1,2-dihydro-3H-benzo[e]indole plays a crucial role in the development of novel anticancer agents. Its unique chemical structure allows for the creation of prodrugs that can be activated in the body, leading to targeted delivery and enhanced efficacy against cancer cells. This makes it a valuable component in the ongoing efforts to develop more effective and targeted cancer treatments.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 20191-75-7 1-bromo-2-naphthylamine 
• 454713-46-3 bis(tert-butyl) 1-bromo-2-naphthyldicarbamate 
• 454713-47-4 tert-butyl (1-bromonaphthalen-2-yl)carbamate 
• 612-52-2 2-naphthylamine hydrochloride 
• 454713-45-2 naphthalen-2-yl-carbamic acid tert-butyl ester 
• 93-09-4 naphthalene-2-carboxylate 
• 454713-48-5 tert-butyl N-(1-bromo-2-naphthyl)-N-(3-chloroprop-2-enyl)carbamate 

Downstream Products

• 1363480-78-7 (E)-N-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1-(hydroxymethyl)-3-(3-(4-methoxyphenyl)acryloyl)-5-nitro-2,3-dihydro-1H-benzo[e]indole-7-sulfonamide 
• 1363480-82-3 (7-(N-(2-((tert-butyldimethylsilyl)oxy)ethyl)sulfamoyl)-5-nitro-3-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-2,3-dihydro-1H-benzo[e]indol-1-yl)methyl phenylmethanesulfonate 
• 1363480-84-5 (7-(N-(2-((tert-butyldimethylsilyl)oxy)ethyl)sulfamoyl)-3-(5-(2-(dimethylamino)ethoxy)-1H-indole-2-carbonyl)-5-nitro-2,3-dihydro-1H-benzo[e]indol-1-yl)methyl phenylmethanesulfonate 
• 1363480-88-9 (7-(N-(2-((tert-butyldimethylsilyl)oxy)ethyl)sulfamoyl)-3-(5-(2-morpholinoethoxy)-1H-indole-2-carbonyl)-5-nitro-2,3-dihydro-1H-benzo[e]indol-1-yl)methyl phenylmethanesulfonate 
• 1363481-19-9 (E)-di-tert-butyl (2-(1-(hydroxymethyl)-3-(3-(3-methoxyphenyl)acryloyl)-5-nitro-2,3-dihydro-1H-benzo[e]indole-7-sulfonamido)ethyl) phosphate 
• 1363481-23-5 (7-(N-(2-((di-tert-butoxyphosphoryl)oxy)ethyl)sulfamoyl)-5-nitro-3-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-2,3-dihydro-1H-benzo[e]indol-1-yl)methyl phenylmethanesulfonate 
• 1363481-25-7 (7-(N-(2-((di-tert-butoxyphosphoryl)oxy)ethyl)sulfamoyl)-3-(5-(2-(dimethylamino)ethoxy)-1H-indole-2-carbonyl)-5-nitro-2,3-dihydro-1H-benzo[e]indol-1-yl)methyl phenylmethanesulfonate 
• 1363481-29-1 (7-(N-(2-((di-tert-butoxyphosphoryl)oxy)ethyl)sulfamoyl)-3-(5-(2-morpholinoethoxy)-1H-indole-2-carbonyl)-5-nitro-2,3-dihydro-1H-benzo[e]indol-1-yl)methyl phenylmethanesulfonate 
• 1363479-11-1 (7-(N-(2-hydroxyethyl)sulfamoyl)-5-nitro-3-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-2,3-dihydro-1H-benzo[e]indol-1-yl)methyl phenylmethanesulfonate 
• 1363479-14-4 C₂HF₃O₂*C₃₅H₃₇N₅O₁₀S₂ 

Relevant academic research and scientific papers

Optimised synthesis of a nitroCBI hypoxia-activated prodrug with substantial anticancer activity

An optimised synthesis of a hypoxia-activated anticancer prodrug related to the duocarmycin family of natural products is described. The improved 10-step synthesis increases the overall yield from 4.4% to over 40% while requiring just 2 chromatography-bas

Re-engineering of the duocarmycin structural architecture enables bioprecursor development targeting CYP1A1 and CYP2W1 for biological activity

A library of duocarmycin bioprecursors based on the CPI and CBI scaffolds was synthesized and used to probe selective activation by cells expressing CYP1A1 and 2W1, CYPs known to be expressed in high frequency in some tumors. Several CPI-based compounds w

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.

Hypoxia-activated prodrugs: Substituent effects on the properties of nitro seco-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one (nitroCBI) prodrugs of DNA minor groove alkylating agents

Nitrochloromethylbenzindolines (nitroCBIs) are a new class of hypoxia-activated prodrugs for antitumor therapy. The recently reported prototypes undergo hypoxia-selective metabolism to form potent DNA minor groove alkylating agents and are selectively tox

NITROBENZINDOLES AND THEIR USE IN CANCER THERAPY

The present invention relates generally to nitro-1,2-dihydro-3H-benzo[e]indoles and related analogues, to their preparation, and to their use as hypoxia-selective drugs and radiosensitizers for cancer therapy, both alone or in combination with radiation a