39273-39-7

Usage

Chemical classification

Synthetic indole derivative

Role

Selective ligand for the sigma-1 receptor

Applications

a. Research studies
b. Potential candidate for anticancer drug development
c. Neuroprotective properties
d. Modulation of neurotransmitter release

Pharmacological activity

Exhibits antiproliferative and cytotoxic effects on various cancer cell lines

Structure

Unique chemical structure that contributes to its pharmacological activity

Therapeutic potential

Valuable tool for understanding the sigma-1 receptor and exploring its potential therapeutic applications
These properties and contents provide a comprehensive overview of BBI, highlighting its chemical composition, applications, and significance in research and therapeutic development.

Upstream product

• 134-32-7 1-amino-naphthalene 
• 201230-82-2 carbon monoxide 
• 130-00-7 1,8-naphtholactam 
• 542-69-8 1-iodo-butane 
• 4734-98-9 benzo[c,d]indole-2(1H)-thione 
• 109-65-9 1-bromo-butane 
• 7797-81-1 N-hydroxy-1,8-naphthalenedicarboximide 
• 109-69-3 n-Butyl chloride 
• 81-84-5 1,8-Naphthalic anhydride 

Relevant academic research and scientific papers

“Turn on” fluorescence response of monomethine cyanines caused by noncovalent binding to ct-DNA

Monomethine cyanines have been extensively studied for their use as probes for nucleic acids among other biological systems. Four monomethine cyanine dyes were synthesized with various heterocyclic moieties including quinoline, benzoxazole, benzothiazole, and 3,3-dimethylindolenine adjoining benz[c,d]indol-1-ium, which was found to directly influence their optical and energy profiles. The dyes were characterized by 1H and 13C NMR and HRMS. In this study the twisted conformation unique to monomethine cyanines was exploited in DNA binding studies where the benzoxazole containing sensor displayed up to 700-fold increase in fluorescence when bound to the DNA compared to the unbound form.

C8-H bond activation vs. C2-H bond activation: From naphthyl amines to lactams

Pd-catalyzed selective amine-oriented C8-H bond functionalization/N-dealkylative carbonylation of naphthyl amines has been achieved. The amine group from dealkylation is proposed to be the directing group for promoting this process. It represents a straightforward and easy method to access various biologically important benzo[cd]indol-2(1H)-one derivatives.

Benz[c,d]indolium-containing monomethine cyanine dyes: Synthesis and photophysical properties

Asymmetric monomethine cyanines have been extensively used as probes for nucleic acids among other biological systems. Herein we report the synthesis of seven monomethine cyanine dyes that have been successfully prepared with various heterocyclic moieties such as quinoline, benzoxazole, benzothiazole, dimethyl indole, and benz[e]indole adjoining benz[c,d]indol-1-ium, which was found to directly influence their optical and energy profiles. In this study the optical properties vs. structural changes were investigated using nuclear magnetic resonance and computational approaches. The twisted conformation unique to monomethine cyanines was exploited in DNA binding studies where the newly designed sensor displayed an increase in fluorescence when bound in the DNA grooves compared to the unbound form.

Synthesis of asymmetric monomethine cyanine dyes with red-shifted optical properties

Six novel asymmetrical monomethine cyanine dyes were synthesized via the condensation reaction of 1-butyl-2-(methylthio)benzo[c,d]indol-1-ium iodide and various 1,5-substituted indolenine salts under basic conditions. The dyes were characterized using UV-vis spectroscopy, fluorescence, 1H NMR, 13C NMR, and mass spectrometry; furthermore, the purity of these compounds was observed using LC/ELSD/MS.

Synthesis and biological evaluation of a benz[cd]indol-2(1H)-one derivatives

Virtual screening of a library of 6.4 million compounds versus the structure of Xenopus Laevis' Aurora B kinase identified 1-(n-propyl)-6-[2-(carboxyl)tetrahydropyrrol-1-yl]sulfonyl-benzo[cd]indol-2(1H)-one 1 as a possible lead compound. Then, a novel series of benz[cd]indol-2(1H)-one derivatives were synthesized and evaluated as Aurora B kinase inhibitors. The structures of the synthetic compounds were confirmed by 1H NMR, IR, mass spectrometry and elemental analysis. These compounds were evaluated by in vitro enzyme assay using spectrophotometry. Among them, compound 7e displayed potent antitumor activity against Aurora B kinase.

Alkylation of 1H-benz[de]isoquinoline-1,3(2H)dione and benz[cd]indol-2(1H)one under conditions of phase-transfer catalysis

The possibility of phase-transfer N-alkylation of 1H-benz[de]isoquinoline-1,3(2H)-dione (naphthalimide) and benz[cd]indol-2(1H)-one (naphthostyril), catalyzed with tetraalkylammonium nitrates, was studied.