64258-95-3

Upstream product

• 120-72-9 indole 
• 202979-89-3 formylamino-piperidinomethyl-malonic acid diethyl ester 
• 46397-90-4 N-[(1H-indol-3-yl)methyl]-N-ethylethanamine 
• 6326-44-9 diethyl 2-formylaminomalonate 
• 5355-42-0 3-(piperidin-1-ylmethyl)-1H-indole 
• 87-52-5 3-(Dimethylaminomethyl)indole 
• 77-78-1 dimethyl sulfate 
• 6829-41-0 diethyl oximinomalonate 

Downstream Products

• 54-12-6 Trp 
• 26988-72-7 2-amino-3-(1-methyl-1H-indol-3-yl)-propanoic acid 
• 119695-02-2 2-benzoyl-3,3-dicarbethoxy-1,2,3,4-tetrahydro-β-carboline 
• 119695-03-3 2-Benzoylamino-2-(2-formyl-1H-indol-3-ylmethyl)-malonic acid diethyl ester 

Relevant academic research and scientific papers

Structure-activity relationship study of novel necroptosis inhibitors

Necroptosis is a regulated caspase-independent cell death mechanism that results in morphological features resembling necrosis. It can be induced in a FADD-deficient variant of human Jurkat T cells treated with TNF-α. 5-(1H-Indol-3-ylmethyl)-2-thiohydantoins and 5-(1H-indol-3-ylmethyl)hydantoins were found to be potent necroptosis inhibitors (called necrostatins). A SAR study revealed that several positions of the indole were intolerant of substitution, while small substituents at the 7-position resulted in increased inhibitory activity. The hydantoin ring was also quite sensitive to structural modifications. A representative member of this compound class demonstrated moderate pharmacokinetic characteristics and readily entered the central nervous system upon intravenous administration.

Model studies related to the total synthesis of the fumitremorgins; the Pictet-Spengler cyclisation and the formation and intramolecular acylation of a 1,2-dihydro-β-carboline derivative

The preparations of the tetrahydro-β-carbolines 8, 9b, and 9d are described. The Pictet-Spengler reaction of L-tryptophyl-L-proline methyl ester with 3-methylbutanal gave the tetrahydro-β-carbolines 20 and 21; subsequent acid-catalysed cyclisation afforded the fumitremorgin analogues 22 and 23. The 2-(p-toluenesulphonyl)tetrahydro-β-carboline 27a furnished the unsaturated pentacycle 28a upon treatment with alkali.

DDQ Oxidations in the Indole Area. Synthesis of 4-Alkoxy-β-carbolines Including the Natural Products Crenatine and 1-Methoxycanthin-6-one

The seven-step synthesis of the cytotoxic, antileukemic alkaloid 1-methoxycanthin-6-one (2b) is described.The pivotal steps are represented by the oxidation (DDQ, aqueous THF, room temperature) of 1-(methoxycarbonyl)-1,2,3,4-tetrahydro-β-carboline (10) to provide the 4-oxo-substituted derivative 14 in 78percent yield, and conversion of the 4-oxo analogue 7 into 4-methoxy-1-alkyl-β-carboline (23) via a methoxylation-oxidation process .This four-step, one-pot reaction has been shown to be general; 4-oxo-1,2,3,4-tetrahydro-β-carboline (18) was converted into the corresponding 4-methoxy-, 4-ethoxy-, 4-(allyloxy)-, and 4-(benzyloxy)-β-carbolines (19a-d, respectively) on heating in the appropriate alcohol in the presence of pTSA and a trialkyl orthoformate (Table II).The proposed mechanism for this intriguing transformation is outlined in Scheme IV.Execution of this process has also resulted in a four-step preparation of crenatine (1a), a 4-methoxy-1-ethyl-β-carboline alkaloid.Finally, steric and electronic parameters have also been successfully manipulated to direct the DDQ oxidation of 1,2,3,4-tetrahydro-β-carbolines to position 1, regiospecifically.The conversion of tetrahydro-β-carboline 25 into 2-acylindole 38 and benzamide 26 into 1-oxotetrahydro-β-carboline 27 (Table I), respectively, is in agreement with the proposed mechanism for this process.

Synthesis of tryptophans

The preparation of racemic and optically pure tryptophans is described. The D-enantiomers of the 6-substituted compounds possess a potent sweetening capability. Novel intermediates are also disclosed.