Articolul precedent |
Articolul urmator |
120 2 |
Ultima descărcare din IBN: 2023-12-10 04:57 |
Căutarea după subiecte similare conform CZU |
547:581.19 (1) |
Chimie organică (484) |
Fiziologia plantelor (526) |
SM ISO690:2012 COJOCARI, Sergiu, MAKAEV, Fliur. Synthesis and characterization of the (1s,3r,4s,6r)-3,4-aza-3,7,7-trimethylbicyclo-[4.1.0]-heptane. In: Natural sciences in the dialogue of generations, 14-15 septembrie 2023, Chişinău. Chişinău: Centrul Editorial-Poligrafic al USM, 2023, p. 206. ISBN 978-9975-3430-9-1. |
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Natural sciences in the dialogue of generations 2023 | |||||||
Conferința "Natural sciences in the dialogue of generations" Chişinău, Moldova, 14-15 septembrie 2023 | |||||||
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CZU: 547:581.19 | |||||||
Pag. 206-206 | |||||||
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In an attempt to develop new antibacterial agents targeted at human dihydrofolate reductase (DHFR) and tymidylate synthase (TS) (two specific enzymes involved in the biosynthesis of the nucleic acids), we designed and synthesized aziredine derivatives. In this context for the synthesis of aziridine with potential biological activity, it appears desirable to combine the aziredine ring with 3,7,7-trimethylbicyclo[4.1.0]heptane moiety e.g. compound 2 starting from (1R,3R,4R,6S)-4-azido-4,7,7-trimethylbicyclo[4.1.0]heptan-3-ol 1. The synthetic route to the target compound formation is depicted in Figure. Cyclization of 1 with Ph3P in refluxing 1,4-dioxane under nitrogen atmosphere afforded the desired aziredine compound 2 in good yield. The aziridine 2 showed in its IR data absorption bands for NH and methyl, respectively. The C(4')-H and NH protons appeared at σ 2.01 and 2.3 ppm, respectively, in its 1H NMR data.Synthesis of (1S,3R,4S,6R)-3,4-aza-3,7,7-trimethylbicyclo-[4.1.0]-heptane A mixture of azidoheptanol 1, Ph3P in 1,4-dioxane was heated gently at 100oC 24 hours. After cooling, it was poured onto ice-water mixture, extracted by EtOAc. The organic layer was washed with water, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography (chloroform) and afforded the target compound 2 with 75%. 1H NMR (400 MHz, CDCl3) δ (ppm) 2.30 (ddd, J = 18.0, 10.6, 8.0 Hz, 1H, H-N), 2.01 (ddd, J = 15.2, 7.3, 1.2 Hz, 1H), 1.94 (dd, J = 7.7 , 4.5 Hz, 1H), 1.32 (s, 3H, H-C9), 1.30 – 1.12 (m, 1H), 0.99 (s, 3H, H-C10), 1.08 – 0.88 (m, 1H), 0.84 (s , 3H, H-C8), 0.88 – 0.56 (m, 4H HC2 and H-C5). 13C NMR (101 MHz, CDCl3) δ 38.17(С10), 35.86(С3), 29.81(С1), 28.70(С6), 27.20(С4), 26.61(С2), 21.89(С5), 21.05(C7), 19.99 (C8), 14.85(C9). |
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Cuvinte-cheie cyclization, (1R,3R,4R,6S)-4-azido-4, 7, 7-trimethylbicyclo[4.1.0]heptan-3-ol, triphenylphosphine |
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