Synthesis and Antibacterial Activity of Pyrroloaryl‐Substituted Oxazolidinones.

Abstract

Synthesis and Antibacterial Activity of Pyrroloaryl-Substituted Oxazolidinones. -A series of pyrroloaryl-substituted oxazolidinones are prepared and screened against a panel of susceptible and resistant Gram-positive bacteria. (VII), (XI) and (XII) show superior or comparable in vitro antibacterial activity as compared to linezolid. -(PAGET*, S. D.; FOLENO, B. D.; BOGGS, C. M.; GOLDSCHMIDT, R. M.; HLASTA, D. J.; WEIDNER-WELLS, M. A.; WERBLOOD, H. M.; WIRA, E.; BUSH, K.; MACIELAG, M. J.; Bioorg. Med. Chem. Lett. 13 (2003) 23, 4173-4177; Johnson and Johnson Pharm. Res. Dev., Raritan, NJ 08869, USA; Eng.) -M. Bohle 13-093

Synthesis, crystal structure, molecular docking and antimicrobial evaluation of new pyrrolo[3,2-c]pyridine derivatives

“…8 General experimental procedure for the synthesis of 7a-f 4-Chloro-2-(cyclohexylmethyl)-3-(morpholinomethyl)-1H-pyrrolo[3,2-c]pyridine (7d) as an example: In an oven-dried RB flask, compound 6c (250 mg, 1.01 mmol) and formaldehyde solution, 37-41 wt.% in water (0.15 mL, 2.02 mmol) were mixed in glacial acetic acid (5 mL). Morpholine (220.4 mg, 2.53 mmol) was added drop wise at 0°C.…”

“…Other examples include the synthetic pyrrolopyridine derivative diazarebeccamycin 2 is a potent anticancer agent [2], pyrrolo [2,3-c]pyridine 3 which has demonstrated activity as an inhibitor of HIV-1 attachment to CD4 + T cells [3] and pyrrolo [2,3-b]pyridine 4 is a potent p38 kinase inhibitor [4]. Pyrrolopyridines also posses significant biological applications such as antimicrobial [5][6][7][8][9], analgesic [10], antimalarial [11], antiproliferative [12], antihypertensive [13], cannabinoid activity [14,15] and Factor VIIa inhibitors [16]. As a result of our considerable interest in the synthesis of pyridine-containing compounds and their antimicrobial activity [17], we initiated a programme directed towards the synthesis of new pyrrolopyridine compounds.…”

“…Therefore, there is an increasing need to design and synthesize new antimicrobial agents with a broad spectrum of activities. On the basis of potential antimicrobial properties of pyrrolopyridine compounds [5][6][7][8][9], we earmarked to design new pyrrolopyridine derivatives anticipating enhanced antimicrobial activity. The new pyrrolopyridines were designed based on the assumptions of Lipinski rule to fulfil the drug likeness properties of the molecules.…”

Synthesis and Antibacterial Properties of Oxazolidinones and Oxazinanones

“…In another recent study using the pyrrolo[3,4-b]pyridinyl oxazolidinone core structure as the template, compounds 74 and 75 were found to exhibit 2 to 4-fold better antibacterial activities than Linezolid [81]. Various modifications of the C-5 acetamido group have been carried out but failed to produce a suitable isosteric replacement.…”

Synthesis and Antibacterial Activity of Novel 2-Oxo-pyrrolidinyl Oxazolidinones

“…Oxazolidinones containing a lactam substituent represented not only antibacterial agents 28,29 but also antithrombotic agents. Rivaroxaban, a lactam substituted oxazolidinone marketed as Xarelto, is orally active and highly potent coagulation factor Xa inhibitors and has been approved in United States recently for the prophylaxis of venous thromboembolism (VTE).…”