Chemistry of Phosphorus Ylides: Part 41 Synthesis of Antimicrobial Agents from the Reaction of Aminoantipyrine, Coumarin- and Quinoline-carbaldehyde with Phosphacumulene and Phosphaallene Ylides

Abstract

Pyrrolo-pyrazoles were obtained from the reaction between phosphacumulenes and aminoantipyrine, while the reaction with the phosphaallene (hexaphenylcarbodiphosphorane ylide) afforded the azaphosphole and pyrazolo-phosphanylidene. The aminocoumarin carbaldehyde gave the chromeno-phosphanylidene and the chromeno-pyridinone, when it was allowed to react with phosphacumulenes. The reaction of chloroquinoline carbaldehyde with the phosphacumulenes, gave chloroquinoline phosphanylidenecyclobutane, while the reaction with phosphaallene resulted in the formation of oxaphosphetane, phosphanylidene ethenyl-and oxaphosphetyl-quinoline. The structure of cyclobutanedione was confirmed by X-ray crystallography. The antimicrobial activity of the new compounds is also reported.

Synthesis, Molecular Docking, and Biofilm Formation Inhibitory Activity of Bis(Indolyl)Pyridines Analogues of the Marine Alkaloid Nortopsentin

“…The plates were incubated at 37 °C for 24 h for bacteria, and at 30 °C for 48 h in an upright position to prevent the scattering of liquid samples and allow maximum growth of the organisms. The antimicrobial activity of the tested samples was investigated by measuring the diameter of the inhibition zones expressed in millimeters (mm) [ 40 ]. The experiment was carried out twice and the mean of the reading was recorded.…”

Chemistry of Phosphorus Ylides: Part 46—Efficient Synthesis and Biological Evaluation of New Phosphorus, Sulfur, and Selenium Pyrazole Derivatives

“…In our continuing studies, we have described the development of new biomolecules of therapeutic interest from the reaction of active and stabilized phosphonium ylides with bioactive natural and unnatural products with potential applications in medicinal chemistry [14][15][16][17][18][19][20][21]. By reacting 1,5-dimethyl-3-oxo-2-phenyl-2,3dihydro-1H-pyrazole-4-carbaldehyde (1) with (Nphenyliminovinylidene)-triphenylphosphorane (2a) in tetrahydrofuran (THF), compound 1,7a-dimethyl-2phenyl-6-(phenylimino)-7-(triphenylphosphoranylidene)-1, 6,7,7a-tetrahydropyrano [4,3-c]pyrazol-3(2H)-one (3a) was obtained.…”

Chemistry of Phosphorus Ylides Part 42: Reaction of Dipyridyl Ethanedione with Phosphorus Reagents. Cytotoxic Activity of Phosphanylidene-Cyclobutane, Oxaphosphetane, and Pyridazinone

“…9 On the other hand, we have been working on active phosphacumulenes, phosphallenes, and stabilized phosphonium ylides with a view to obtain new carbocyclic and heterocyclic biologically active phosphorus compounds. [10][11][12][13][14][15] Moreover, Lawesson's and Japanese reagents have been shown to be good starting materials for the construction of cyclic systems containing phosphorus and sulphur. [16][17][18][19][20][21] Herein, we report on the synthesis, structural and antitumor activity of pyridinephosphanylidenecyclobutane, oxaphosphetane, butenoate, pyridazinone and oxathiaphosphetane, from the reaction of the above mentioned phosphorus reagents with 1,2-bis(2-pyridyl)ethane-1,2-dione.…”