CsF–Celite catalyzed facile N-alkylation of 2(3H)-benzoxazolones and antimicrobial properties of 2-substituted benzoxazole and 3-substituted-2(3H)-benzoxazolone derivatives

Abstract

The synthesis and antimicrobial activity studies of a new series of cyclic amine containing benzoxazoles and benzoxazolone-2(3H)-ones derivatives were described. The alkylation of benzoxazolone was carried out using cesium fluoride-Celite. The newly synthesized compounds with the influence of the induction of the cyclic amine moiety in the benzoxazole scaffold have been evaluated with respect to the antibacterial and antifungal activity. The 2-cyclic amine-1,3-benzoxazoles (5a-l), 5-chloro-3-alkyl substituted-1,3-benzoxazol-2(3H)-ones (8a-f), and 3-[3-(cyclic amine)propyl]-1,3-benzoxazol-2(3H)-ones (9a-f) were synthesized. These derivatives were tested for antibacterial and antifungal activity. Among the compounds tested, 8c and 9f showed moderate to good antibacterial and antifungal activity. Compound 8a showed good antifungal activity.

Room-Temperature Amination of Chloroheteroarenes in Water by a Recyclable Copper(II)-Phosphaadamantanium Sulfonate System

“…for C 11 H 12 N 2 O 2 [M], found: 205 [M + H]. The compound exhibited identical 1 H and 13 C­{ 1 H} NMR data to previous reports …”

“…The compound exhibited identical 1 H and 13 C{ 1 H} NMR data to previous reports. 62 2-(4-Methylpiperazin-1-yl)benzo [d]thiazole (3w).…”

Importance of Fluorine in Benzazole Compounds

“…In addition, benzoxazole derivatives possess a variety of biological activities such as antitumor [ 112 , 113 , 114 , 115 ], antituberculosis [ 116 ], antifungal [ 117 ], antimicrobial [ 118 , 119 , 120 , 121 , 122 , 123 ], antihypertension [ 124 ], antiviral [ 97 , 125 ], antihormonal [ 126 ], and radioligand agents [ 127 , 128 , 129 ]. Because of the aforementioned properties of both fluorine and benzazoles, efforts have been done by Nosova et al to summarize several methods of synthesizing fluorinated benzazoles [ 130 ].…”

4‐Sulfonyloxy/alkoxy benzoxazolone derivatives with high anti‐inflammatory activities: Synthesis, biological evaluation, and mechanims of action via p38/ERK‐NF‐κB/iNOS pathway

“…Benzoxazole derivatives have occupied a prominent role in medicinal chemistry based on their diverse and significant biological properties, including anti‐inflammatory, anti‐arrhythmic, anti‐cancer, anti‐microbial, and anti‐HIV activities (Abdelazeem et al, 2015; Murty et al, 2011; Önkol et al, 2004; Tang et al, 2013). A series of 4‐phenylsulfonyl benzoxazolone derivatives was synthesized by our group, and the lead compound 4‐ o ‐methyl‐benzenesulfonyl benzoxazolone (MBB), with definitive anti‐inflammatory activity in vitro and in vivo, was obtained (Tang et al, 2018).…”