675606-20-9

Basic information

• Product Name: 1-(TERT-BUTOXYCARBONYL)-1H-INDOLE-3-CARBOXYLIC ACID
• Synonyms: 1-(TERT-BUTOXYCARBONYL)-1H-INDOLE-3-CARBOXYLIC ACID;1H-INDOLE-1,3-DICARBOXYLIC ACID,1-(1,1-DIMETHYLETHYL)ESTER
• CAS NO: 675606-20-9
• Molecular Formula: C₁₄H₁₅NO₄
• Molecular Weight: 261.27
• Mol File: 675606-20-9.mol
• Article Data: 4

Chemical Properties

• Melting Point: 240-241 °C
• Boiling Point: 431.9±37.0 °C(Predicted)
• Appearance: /
• Density: 1.22±0.1 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 3.43±0.10(Predicted)
• CAS DataBase Reference: 1-(TERT-BUTOXYCARBONYL)-1H-INDOLE-3-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(TERT-BUTOXYCARBONYL)-1H-INDOLE-3-CARBOXYLIC ACID(675606-20-9)
• EPA Substance Registry System: 1-(TERT-BUTOXYCARBONYL)-1H-INDOLE-3-CARBOXYLIC ACID(675606-20-9)

Safety Data

• Hazardous Substances Data: 675606-20-9(Hazardous Substances Data)

Usage

General Description

1-(tert-butoxycarbonyl)-1H-indole-3-carboxylic acid is a chemical compound with the molecular formula C16H17NO4. It is a tert-butoxycarbonyl-protected derivative of 1H-indole-3-carboxylic acid, which is commonly used in the synthesis of pharmaceuticals and other organic compounds. 1-(TERT-BUTOXYCARBONYL)-1H-INDOLE-3-CARBOXYLIC ACID is often used as a building block in the production of various drugs and pharmaceuticals due to its versatility and reactivity. Its structure makes it suitable for use in a wide range of chemical reactions, making it a valuable tool for organic chemists and pharmaceutical researchers.

Upstream product

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

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 articles and documents

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.

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.