¹H and ¹³C NMR studies of 2‐functionalized 5‐(methylsulfonyl)‐1‐phenyl‐1H‐indoles

Abstract

The 1H and 13C NMR resonances of thirty 2-functionalized 5-(methylsulfonyl)-1-phenyl-1H-indoles were assigned completely and unequivocally using the concerted application of one- and two-dimensional experiments (DEPT, gs-HMQC and gs-HMBC). Finally, the influence of the 2-substituent of 5-(methylsufonyl)-1-phenyl-1H-indoles on the carbon atoms of the indole moiety was estimated.

Structure-based predictions of 13C-NMR chemical shifts for a series of 2-functionalized 5-(methylsulfonyl)-1-phenyl-1H-indoles derivatives using GA-based MLR method

“…[13][14][15][16][17][18][19]; and (iv) 5-(methylsulfonyl)-1-phenyl-1H-indole-2-carboxamides (Nos. [20][21][22][23][24][25][26][27][28][29][30], where each containing 14 carbon atoms and consequently a total of 420 chemically non-equivalent carbon centers were obtained from the literature [9]. The chemical structures, numbering and experimental carbon-13 NMR chemical shift values of all 420 atoms in the thirty indole derivatives examined are scheduled in Table 1 and Table S1 …”

“…At the moment, there are approximately 1500 indole alkaloids described [6,7]. In 2003, Cruz-López and coworkers prepared a series of 1-substituted 5-(methylsulfonyl)-1H-indole-2-carboxylic acid esters, -2-nitriles-, and -2-carboxamides by replacing the benzoyl group of indomethacin with a substituted phenyl group [8] and after that, they synthesized some derivatives of this group with different substituents [9]. They found that substitution on the indole nitrogen atom with the pmethylthiophenyl group on N-butyl and N-pentyl-2-carboxamides provided active and selective COX-2 enzyme inhibitors.…”