Synthesis of osteotropic hydroxybisphosphonate derivatives of fluoroquinolone antibacterials

Design, Synthesis and in vitro Antimycobacterial Activities of Isatin‐1,2,3‐triazole‐moxifloxacin Hybrids

“…Isatin, 5-bromoisatin, and MXFX were alkylated with 1,2-dibromoethane and propargyl bromide, respectively, in the presence of anhydrous potassium carbonate to provide the corresponding N-(2-bromoethyl)isatins 2a,b (yield: 56% and 62%) and propargyl MXFX 4 (yield: 69%) via literature methods [18][19][20][21][22]. Treatment of N-(2-bromoethyl)isatins 2a,b with sodium azide at 60°C yielded the desired azido precursors 3a,b, which was used together with 4 for the synthesis of desired 1,2,3-triazole-tethered hybrids 5a,b (yield: 46% and 48%) in the presence of Cu(OAc) 2 in DMF [18].…”

Physiologic Activity of Bisphosphonates – Recent Advances

“…Preparation of hydroxyphosphonate derivatives of ciprofloxacin and moxifloxacin (representative structure is shown in Scheme 9) represents a similar concept of combining bone-targeting and antibacterial properties in one molecule [189]. In summary, the application of bisphosphonates as potential antibacterial agents has been considered very recently, but the number of reports is limited.…”

“…The most common treatments are antibiotics and surgery to remove portions of bone that are infected or dead. Thus, selective targeting of antibiotics to bone seems to be profitable, and some preliminary attempts to design and obtain osteotropic systems with fluoroquinones, [113,114] vancomycin [115] and rifamycin [116] as active components have been undertaken.…”

Design, Synthesis and In Vitro Anti‐mycobacterial Activities of 8‐OMe Ciprofloxacin‐1H‐1,2,3‐triazole‐isatin‐(thio) Semicarbazide/Oxime Hybrids

“…Various C-5 substituted isatins and 8-OMe CPFX were alkylated with 1,2-dibromoethane and propargyl bromide, respectively, in the presence of anhydrous potassium carbonate to give the corresponding N-(2-bromoethyl) isatins 2a-d (yield: 51-67%) and propargyl 8-OMe CPFX 4 (yield: 61%) via literature methods [17][18][19]. The subsequent treatment of C-5 substituted N-(2-bromoethyl) isatins 2a-d with sodium azide at 60°C to provide the desired azido precursors 3a-d [11].…”

“…The subsequent treatment of C-5 substituted N-(2-bromoethyl) isatins 2a-d with sodium azide at 60°C to provide the desired azido precursors 3a-d [11]. The precursors 3a-d and 4 were used for the synthesis of desired 1,2,3-triazole-tethered hybrids via Cu-promoted azide-alkyne cycloaddition reaction in the presence of Cu(OAc) 2 in DMF gave compounds 5a-d (yield: 21-39%) [18]. Subsequent condensations of compounds 5a-d with requisite substituted amine hydrochlorides in the presence of sodium bicarbonate to provide the desired hybrids 6a-l (10-63%) [19].…”