1452759-99-7

Basic information

• Product Name: 3,3′-(1-(3,4,5-trimethoxyphenyl)ethane-1,1-diyl)bis(1H-indole)
• Synonyms: 3,3′-(1-(3,4,5-trimethoxyphenyl)ethane-1,1-diyl)bis(1H-indole)
• CAS NO: 1452759-99-7
• Molecular Weight: 426.515
• Mol File: 1452759-99-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 3,3′-(1-(3,4,5-trimethoxyphenyl)ethane-1,1-diyl)bis(1H-indole)(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3′-(1-(3,4,5-trimethoxyphenyl)ethane-1,1-diyl)bis(1H-indole)(1452759-99-7)
• EPA Substance Registry System: 3,3′-(1-(3,4,5-trimethoxyphenyl)ethane-1,1-diyl)bis(1H-indole)(1452759-99-7)

Safety Data

• Hazardous Substances Data: 1452759-99-7(Hazardous Substances Data)

Upstream product

• 120-72-9 indole 
• 4698-21-9 3-(3,4,5-trimethoxyphenyl)propiolic acid 
• 13400-02-7 3,4,5-trimethoxy styrene 
• 1136-86-3 methyl (3,4,5-trimethoxyphenyl) ketone 

Relevant articles and documents

Decarboxylative Addition of Propiolic Acids with Indoles to Synthesize Bis(indolyl)methane Derivatives with a Pd(II)/LA Catalyst

Exploring new protocols for efficient organic synthesis is crucial for pharmaceutical developments. The present work introduces a Pd(II)/LA-catalyzed (LA: Lewis acid) decarboxylative addition reaction for the synthesis of bis(indolyl)methane derivatives. The presence of Lewis acid such as Sc(OTf)3 triggered Pd(II)-catalyzed decarboxylative addition of propiolic acids with indoles to offer the bis(indolyl)methane derivatives in moderate to good yields, whereas neither Pd(II) nor Lewis acid alone was active for this synthesis. The catalytic efficiency of Pd(OAc)2 was highly dependent on the Lewis acidity of the added Lewis acid, that is, a stronger Lewis acid provided a higher yield of the bis(indolyl)methane derivatives. Meanwhile, this Pd(II)/LA-catalyzed decarboxylative addition reaction showed good tolerance toward versatile electron-rich or-deficient substituents on the indole skeleton and on the benzyl ring of propiolic acids. The studies on the in situ 1H NMR kinetics of this Pd(II)/Sc(III) catalysis disclosed the formation of a transient vinyl-Pd(II)/Sc(III) intermediate generated by the pyrrole addition to the alkynyl-Pd(II)/Sc(III) species after decarboxylation, which was scarcely observed before.

Synthesis of a new bis(indolyl)methane that inhibits growth and induces apoptosis in human prostate cancer cells

The synthesis and the antiproliferative activity against the human breast MCF-7, SkBr3 and the prostate LNCaP cancer cell lines of a series of bis(indolyl)methane derivatives are reported. The synthesis of new compounds was first accomplished by the reaction of different indoles with trimethoxyacetophenone in the presence of catalytic amounts of hydrochloric acid. A second procedure involving the use of oxalic acid dihydrate [(CO 2H)2·2H2O] and N-cetyl-N,N,N- trimethylammonium bromide in water was carried out and led to better yields. Compound 5b significantly reduced LNCaP prostate cancer cell viability in a dose-dependent manner, with an IC50 of 0.64 ± 0.09 M. To determine whether the growth inhibition was associated with the induction of apoptosis, treated cells were stained using DAPI. LNCaP cells treated with 1 M of 5b showed the morphological changes characteristic of apoptosis after 24 h of incubation.