460096-34-8

Upstream product

• 1074-86-8 4-formyl indole 
• 24424-99-5 di-tert-butyl dicarbonate 
• 298-12-4 Glyoxilic acid 
• 676448-17-2 4-bromoindole-1-carboxylic acid tert-butyl ester 
• 68-12-2 N,N-dimethyl-formamide 
• 52488-36-5 4-bromo-1H-indole 
• 1233500-93-0 C₁₄H₁₄N₂O₂ 
• 16136-52-0 4-cyanoindole 

Downstream Products

• 460096-20-2 (S)-N^α-benzyloxycarbonyl-Nⁱⁿ-tert-butyloxycarbonyl-3-(indol-4'-yl)-alanine, methyl ester 
• 938185-67-2 3-(1H-indol-4-yl)propyl phenyl sulfoxide 
• 938185-65-0 3-{1-[(tert-butoxy)carbonyl]-1H-indol-4-yl}propyl phenyl sulfoxide 
• 938185-63-8 3-{1-[(tert-butoxy)carbonyl]-1H-indol-4-yl}propyl phenyl sulfide 
• 938185-59-2 N,N-dimethyl-1H-indole-4-propanethioamide 
• 938185-48-9 1-[(tert-butoxy)carbonyl]-N-methyl-N-phenyl-1H-indole-4-propanamide 
• 460096-31-5 (Z)-N^α-benzyloxycarbonyl-Nⁱⁿ-tert-butyloxycarbonyl-2,3-dehydro-3-(indol-4'-yl)-alanine, methyl ester 

Relevant academic research and scientific papers

An efficient and concise synthesis of Indiacen A and Indiacen B

A novel total synthesis of antimicrobial prenyl indoles, Indiacen A and its chloro analogue Indiacen B has been accomplished by using Horner-Wadsworth-Emmons olefination for terminal conjugated enynes, carboalumination, chlorination and Vilsmeier-Haack formylation as the key transformations.

Structure-guided design, synthesis, and biological evaluation of (2-(1 H-Indol-3-yl)-1 H-imidazol-4-yl)(3,4,5-trimethoxyphenyl) methanone (ABI-231) analogues targeting the colchicine binding site in Tubulin

ABI-231 is a potent, orally bioavailable tubulin inhibitor that interacts with the colchicine binding site and is currently undergoing clinical trials for prostate cancer. Guided by the crystal structure of ABI-231 in complex with tubulin, we performed structure-activity relationship studies around the 3-indole moiety that led to the discovery of several potent ABI-231 analogues, most notably 10ab and 10bb. The crystal structures of 10ab and 10bb in complex with tubulin confirmed their improved molecular interactions to the colchicine site. In vitro, biological studies showed that new ABI-231 analogues disrupt tubulin polymerization, promote microtubule fragmentation, and inhibit cancer cell migration. In vivo, analogue 10bb not only significantly inhibits primary tumor growth and decreases tumor metastasis in melanoma xenograft models but also shows a significant ability to overcome paclitaxel resistance in a taxane-resistant PC-3/TxR model. In addition, pharmacological screening suggested that 10bb has a low risk of potential off-target function.

Synthesis of Aldehydes by Organocatalytic Formylation Reactions of Boronic Acids with Glyoxylic Acid

Reported herein is a conceptually novel organocatalytic strategy for the formylation of boronic acids. New reactivity is engineered into the α-amino-acid-forming Petasis reaction occurring between aryl boronic acids, amines, and glyoxylic acids to prepare aldehydes. The operational simplicity of the process and its ability to generate structurally diverse and valued aryl, heteroaryl, and α,β-unsaturated aldehydes containing a wide array of functional groups, demonstrates the practical utility of the new synthetic strategy.

Synthesis of functionalized cyclohexenone core of welwitindolinones via rhodium-catalyzed [5 + 1] cycloaddition

The cyclohexenone core of welwitindolinones was synthesized by a Rh(I)-catalyzed [5 + 1]-cycloaddition of an allenylcyclopropane with CO. A pentasubstituted cyclopropane was prepared successfully by a Rh(II)-catalyzed intramolecular cyclopropanation of alkenes with chlorodiazoacetates.

INDOLE AND INDAZOLE ANALOGS AS GLYCOGEN SYNTHASE ACTIVATORS

Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful

Catalytic asymmetric synthesis of protected tryptophan regioisomers

Tryptophan 1 (Trp) is superior to all other naturally occurring peptide residues in its ability to bind cations (the cation - π interaction). In an effort to expand the toolbox of Trp-like amino acids, in this note we report catalytic asymmetric syntheses of Trp regioisomers 2a - e, where the alanine unit is attached not to C-3 of indole but to C-2, C-4, C-5, C-6, or C-7. Excellent asymmetric induction is obtained in each case (generally >97% ee). Ab initio calculations suggest that the indole nuclei of 2a-e will bind Na+ with the same affinity as that of Trp.