60376-48-9

Basic information

• Product Name: METHYL 1-(PHENYLSULFONYL)-1H-INDOLE-2-CARBOXYLATE
• Synonyms: METHYL 1-(PHENYLSULFONYL)-1H-INDOLE-2-CARBOXYLATE;RARECHEM AL BF 1292
• CAS NO: 60376-48-9
• Molecular Formula: C₁₆H₁₃NO₄S
• Molecular Weight: 315.34
• Mol File: 60376-48-9.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: METHYL 1-(PHENYLSULFONYL)-1H-INDOLE-2-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 1-(PHENYLSULFONYL)-1H-INDOLE-2-CARBOXYLATE(60376-48-9)
• EPA Substance Registry System: METHYL 1-(PHENYLSULFONYL)-1H-INDOLE-2-CARBOXYLATE(60376-48-9)

Safety Data

• Hazardous Substances Data: 60376-48-9(Hazardous Substances Data)

Upstream product

• 1202-04-6 indole-2-carboxylic acid methyl ester 
• 98-09-9 benzenesulfonyl chloride 
• 186581-53-3 diazomethane 
• 40899-93-2 1-(phenylsulfonyl)-1H-indole-2-carboxylic acid 
• 40899-71-6 1-benzenesulfonylindole 
• 1477-50-5 Indole-2-carboxylic acid 

Downstream Products

• 1202-04-6 indole-2-carboxylic acid methyl ester 
• 1239864-83-5 1-methyl-4-(phenyl-sulfonyl)-1H-furo[3,4-b]indol-3(4H)-one 
• 1352536-81-2 C₁₉H₂₁N₃O₄S 
• 1352536-84-5 C₂₂H₂₇N₃O₄S 
• 1352536-86-7 C₂₀H₁₉NO₄S 
• 1352536-91-4 C₂₁H₂₁NO₃S 
• 1239864-88-0 N-benzenesulfonyl-2-(N',N'-dimethylhydrazinecarbonyl)indole 
• 89241-38-3 1,3-dimethyl-4-(phenylsulfonyl)-4H-furo[3,4-b]indole 
• 342405-28-1 1-phenylsulfonyl-1H-2-indolecarboxylic acid chloride 
• 1620064-65-4 methyl 3-(diphenylphosphoryl)-1H-indole-2-carboxylate 

Relevant articles and documents

Fragment-Based Design, Synthesis, and Biological Evaluation of 1-Substituted-indole-2-carboxylic Acids as Selective Mcl-1 Inhibitors

Based on a known selective Mcl-1 inhibitor, 6-chloro-3-(3-(4-chloro-3,5-dimethylphenoxy)propyl)-1H-indole-2-carboxylic acid, we applied a fragment-based approach to obtain new molecules that extended into the p1 pocket of the BH3 groove and then exhibited binding selectivity for the Mcl-1 over the Bcl-2 protein. After we deconstructed the 1H-indole-2-carboxylic acid from the parental molecule, a benzenesulfonyl was substituted at the 1-position to adopt a geometry preferred for accessing the p1 pocket according to the binding mode of the parental molecule identified by X-ray crystallography. A linear relationship between the free energy of ligand binding (ΔG) and the count of non-hydrogen heavy atoms (HAC) was maintained during the molecular growing to occupy the p1 pocket. Finally, we not only obtained compound 12 with a 7.5-fold selectivity to Mcl-1 (Ki = 0.48 μM by fluorescence polarization) over Bcl-2 (Ki = 3.6 μM), but also provided evidence that additional occupation of the p1 pocket is more favorable for Mcl-1 than for Bcl-2 binding, and contributes more to Mcl-1 inhibition than occupation of the p2 pocket. Compound 12 exhibited a selective killing ability on Mcl-1-dependent cancer cells.

A convenient access to 1,3-disubstituted furo[3,4-b]indoles by acid ion-exchange resin-catalyzed furan formation

Efficient synthesis of furo[3,4-b]indoles starting from the corresponding indole is reported. The first route involves derivatization, protection, and deprotection steps, which stretch the syntheses. The second method provides a shorter and more efficient strategy to accessing the furoindole. The innovation starts with alkylation at C-2 of the indole presenting at the C-3 position a ketone-acetal, followed by the cycloaromatization catalyzed by polymeric ion-exchange resins. The second route represents a significant improvement over other methods previously described.