127956-28-9

Basic information

• Product Name: TERT-BUTYL 6-FORMYL-1H-INDOLE-1-CARBOXYLATE
• Synonyms: TERT-BUTYL 6-FORMYL-1H-INDOLE-1-CARBOXYLATE
• CAS NO: 127956-28-9
• Molecular Formula: C₁₄H₁₅NO₃
• Molecular Weight: 245.277
• Mol File: 127956-28-9.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 380.0±34.0 °C(Predicted)
• Appearance: /
• Density: 1.13±0.1 g/cm3(Predicted)
• CAS DataBase Reference: TERT-BUTYL 6-FORMYL-1H-INDOLE-1-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL 6-FORMYL-1H-INDOLE-1-CARBOXYLATE(127956-28-9)
• EPA Substance Registry System: TERT-BUTYL 6-FORMYL-1H-INDOLE-1-CARBOXYLATE(127956-28-9)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 127956-28-9(Hazardous Substances Data)

Usage

General Description

TERT-BUTYL 6-FORMYL-1H-INDOLE-1-CARBOXYLATE is a chemical compound with the molecular formula C15H17NO3. It is a formylated derivative of indole carboxylic acid, with a tert-butyl group attached to the indole nitrogen and a formyl group attached to the 6-position of the indole ring. TERT-BUTYL 6-FORMYL-1H-INDOLE-1-CARBOXYLATE is commonly used in the field of organic synthesis and medicinal chemistry for the preparation of various indole derivatives and as a building block for pharmaceutical compounds. Its unique structure and properties make it a valuable tool for the development of new drugs and therapeutic agents. However, it is important to handle this compound with caution as it may have hazardous properties.

Upstream product

• 298-12-4 Glyoxilic acid 
• 127956-24-5 tert-butyl 6-methyl-1H-indole-1-carboxylate 
• 34619-03-9 tert-butyldicarbonate 
• 3420-02-8 6-methylindole 
• 1196-70-9 indole-6-carboxaldehyde 
• 24424-99-5 di-tert-butyl dicarbonate 
• 127956-25-6 6-(bromomethyl)-1-(tert-butoxycarbonyl)indole 

Downstream Products

• 1196-70-9 indole-6-carboxaldehyde 
• 127956-27-8 6-(difluoromethyl)indole 
• 39689-57-1 2-(1H-indol-6-yl)acetonitrile 
• 39689-58-2 2-(indol-6-yl)acetic acid 
• 1298129-85-7 3-[6-(4',5'-difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-indol-1-yl]-propionic acid ethyl ester 
• 1298129-79-9 6-(4',5'-difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-indole-1-carboxylic acid tert-butyl ester 
• 1298129-83-5 3-[6-(4',5'-difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-indol-1-yl]-propionic acid 
• 1298129-74-4 6-(4',5'-difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-1H-indole 
• 354587-72-7 tert-butyl 6-(hydroxymethyl)-1H-indole-1-carboxylate 
• 460096-23-5 6-(2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-indole-1-carboxylic acid tert-butyl ester 
• 460096-33-7 6-(2-benzyloxycarbonylamino-2-methoxycarbonyl-vinyl)-indole-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

POLYHETEROCYCLIC COMPOUNDS AS METTL3 INHIBITORS

The present invention relates to compounds of formula (I) that function as inhibitors of METTL3 (N6-adenosine-methyltransferase 70 kDa subunit) enzyme activity: X-Y-Z (I) wherein X, Y and Z are each as defined herein. The present invention also relates to processes for the preparation of these compounds, to pharmaceutical compositions comprising them, and to their use in the treatment of proliferative disorders, such as cancer, and autoimmune diseases, as well as other diseases or conditions in which METTL3 activity is implicated.

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.