79302-77-5Relevant academic research and scientific papers
Substitution of terminal amide with 1H-1,2,3-triazole: Identification of unexpected class of potent antibacterial agents
Bi, Fangchao,Ji, Shengli,Venter, Henrietta,Liu, Jingru,Semple, Susan J.,Ma, Shutao
supporting information, p. 884 - 891 (2018/02/15)
3-Methoxybenzamide (3-MBA) derivatives have been identified as novel class of potent antibacterial agents targeting the bacterial cell division protein FtsZ. As one of isosteres for the amide group, 1,2,3-triazole can mimic the topological and electronic features of the amide, which has gained increasing attention in drug discovery. Based on these considerations, we prepared a series of 1H-1,2,3-triazole-containing 3-MBA analogues via isosteric replacement of the terminal amide with triazole, which had increased antibacterial activity. This study demonstrated the possibility of developing the 1H-1,2,3-triazole group as a terminal amide-mimetic element which was capable of both keeping and modulating amide-related bioactivity. Surprisingly, a different action mode of these new 1H-1,2,3-triazole-containing analogues was observed, which could open new opportunities for the development of antibacterial agents.
Syntheses and Reactions of (Trimethylsiloxy)benzoyl Chlorides
Schwarz, Gerd,Alberts, Heinrich,Kricheldorf, Hans R.
, p. 1257 - 1270 (2007/10/02)
The (trimethylsiloxy)benzoyl chlorides 1-7 are easily to obtain under mild conditions from silylated hydroxybenzoic acids by means of thionyl chloride.Whereas these acid chlorides are stable at room temperature, they undergo condensation polymerisation at temperatures above 100 deg C.Reactions with various nucleophils, such as thioalcohols, phenols, amines, N,O-bis(silylated)amino acids and N-silylated lactams were investigated.With hexamethyldisilazane and thionyl chloride the (trimethylsiloxy)benzonitriles 21, 22 are accessible, and by means of trimethylsilylazide the (trimethylsiloxy)phenyl isocyanates 23-25 were obtained.Conversion with phenyl carbazate and subsequent silylation lead to the 2-(trimethylsiloxy)phenyl-1,3,4-oxadiazol-5-ones 27a-c.
