675606-20-9

Usage

Uses

Used in Pharmaceutical Industry:
1-(TERT-BUTOXYCARBONYL)-1H-INDOLE-3-CARBOXYLIC ACID is used as a key building block for the synthesis of various pharmaceuticals due to its reactivity and compatibility in a wide range of chemical reactions. Its protected structure ensures stability during the synthesis process, facilitating the development of new drugs with improved properties.
Used in Organic Chemistry Research:
In the field of organic chemistry, 1-(TERT-BUTOXYCARBONYL)-1H-INDOLE-3-CARBOXYLIC ACID is employed as a versatile reagent for conducting numerous chemical reactions. Its unique structure allows researchers to explore new synthetic pathways and develop innovative organic compounds with potential applications in various industries.
Used in Drug Development:
1-(TERT-BUTOXYCARBONYL)-1H-INDOLE-3-CARBOXYLIC ACID is utilized as a starting material in drug development, enabling the creation of novel therapeutic agents with enhanced efficacy and selectivity. Its protected nature allows for controlled deprotection and functionalization, facilitating the synthesis of complex drug molecules with desired pharmacological properties.

Upstream product

• 771-50-6 1H-indole-3-carboxylic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 57476-50-3 1-tert-butoxycarbonyl-3-formylindole 
• 34619-03-9 tert-butyldicarbonate 

Downstream Products

• 1213775-74-6 tert-butyl 3-(phenylcarbamoyl)-1H-indole-1-carboxylate 
• 1213775-75-7 tert-butyl 3-(3-nitrophenylcarbamoyl)-1H-indole-1-carboxylate 
• 1213775-73-5 tert-butyl 3-(2,4-dimethoxyphenylcarbamoyl)-1H-indole-1-carboxylate 
• 448906-42-1 ITE 
• 214759-95-2 N-methoxy-N-methyl-1H-indole-3-carboxamide 
• 57476-50-3 1-tert-butoxycarbonyl-3-formylindole 

Relevant academic research and scientific papers

PROCESSES FOR THE PREPARATION OF ARYL HYDROCARBON RECEPTOR LIGANDS

The present disclosure relates to the preparation of methyl 2-(1H-indole-3-carbonyl)thiazole-4-carboxylate (ITE) and related compounds with high yield, purity, and scalability. The processes apply the use of a Weinreb amide intermediate as a scaffold for the preparation of ITE and structural analogs.

Site Selective Chlorination of C(sp3)?H Bonds Suitable for Late-Stage Functionalization

C(sp3)?Cl bonds are present in numerous biologically active small molecules, and an ideal route for their preparation is by the chlorination of a C(sp3)?H bond. However, most current methods for the chlorination of C(sp3)?H bonds are insufficiently site selective and tolerant of functional groups to be applicable to the late-stage functionalization of complex molecules. We report a method for the highly selective chlorination of tertiary and benzylic C(sp3)?H bonds to produce the corresponding chlorides, generally in high yields. The reaction occurs with a mixture of an azidoiodinane, which generates a selective H-atom abstractor under mild conditions, and a readily-accessible and inexpensive copper(II) chloride complex, which efficiently transfers a chlorine atom. The reaction's exceptional functional group tolerance is demonstrated by the chlorination of >30 diversely functionalized substrates and the late-stage chlorination of a dozen derivatives of natural products and active pharmaceutical ingredients.

Synthesis, and evaluation of in vitro and in vivo anticancer activity of 14-substituted oridonin analogs: A novel and potent cell cycle arrest and apoptosis inducer through the p53-MDM2 pathway

A series of novel oridonin derivatives bearing various substituents on the 14-OH position were designed and synthesised. Their antitumour activity was evaluated in vitro against three human cancer cell lines (HCT116, BEL7402, and MCF7). Most tested derivatives showed improved anti-proliferative activity compared to the lead compound oridonin and the positive control drug 5-fluorouracil (5-Fu). Among them, compound C7 (IC50 = 0.16 μM) exhibited the most potent anti-proliferative activity against HCT116 cells; it was about 43- and 155-fold more efficacious than that of oridonin (IC50 = 6.84 μM) and 5-Fu (IC50 = 24.80 μM) in HCT116 cancer cells. Interestingly, the IC50 value of compound C7 in L02 normal cells was 23.6-fold higher than that in HCT116 cells; it exhibited better selective anti-proliferative activity and specificity than oridonin and 5-Fu. Furthermore, compound C7 possibly induced cell cycle arrest and apoptosis by regulating the p53-MDM2 signalling pathway. Notably, C7 displayed more significant suppression of tumour growth than oridonin in colon tumour xenograft models where the tumour growth inhibition rate was 85.82%. Therefore, compound C7 could be a potential lead compound for the development of a novel antitumour agent.

A Highly Efficient NHC-Catalyzed Aerobic Oxidation of Aldehydes to Carboxylic Acids

An N-heterocyclic carbene (NHC) organocatalytic aerobic oxidation of aldehydes to the corresponding carboxylic acids is explored. Remarkably, this method allows for efficient conversion of different classes of aldehydes including highly challenging electron-rich aryl aldehydes, ortho -substituted aryl aldehydes, various heteroaromatic aldehydes and α,β-unsaturated aldehydes under mild reaction conditions. These substrates, under previously reported NHC-catalyzed methods, are typically unreactive or give poor yields, require high reaction temperatures and reaction times of several days.