Improved Procedure for Conversion of Penicillin V Into Monocyclic β-Lactams

1987 ◽  
Vol 40 (1) ◽  
pp. 223 ◽  
Author(s):  
M Davis ◽  
WY Wu

Improved procedures for the preparation of the Kamiya compound (3 R,4R)-4-(benzothiazol-2′-yldithio)-3-phenoxyacetamidoazetidin-2-0 (6) from penicillin V (1) are described. A novel feature is ozonolysis, near room temperature, in aqueous methanol in the presence of pyridine or a trace of manganese dioxide.

2018 ◽  
Vol 14 ◽  
pp. 547-552 ◽  
Author(s):  
Ernesto Emmanuel López-López ◽  
José Alvano Pérez-Bautista ◽  
Fernando Sartillo-Piscil ◽  
Bernardo A Frontana-Uribe

An electrochemical version of the Corey–Winter reaction was developed giving excellent results in aqueous methanol media (MeOH/H2O (80:20) with AcOH/AcONa buffer 0.5 M as supporting electrolyte), using a reticulated vitreous carbon as cathode in a divided cell. The electrochemical version is much more environmentally friendly than the classical reaction, where a large excess of trialkyl phosphite as reducing agent and high temperatures are required. Thus, cathodic reduction at room temperature of two cyclic thiocarbonates (−1.2 to −1.4 V vs Ag/AgCl) afforded the corresponding alkenes, trans-6-(pent-1-enyl)-α-pyrone and trans-6-(pent-1,4-dienyl)-α-pyrone, which are naturally occurring metabolites isolated from Trichoderma viride and Penicillium, in high chemical yield and with excellent stereo selectivity.


2020 ◽  
Vol 605 ◽  
pp. 118094 ◽  
Author(s):  
Min Hu ◽  
Linghui Yin ◽  
Huixian Zhou ◽  
Lvxiong Wu ◽  
Kai Yuan ◽  
...  

2019 ◽  
Vol 92 (2) ◽  
pp. 269-277
Author(s):  
Hamit Ismaili ◽  
Josipa Matić ◽  
Biserka Žinić ◽  
Ljubica Glavaš-Obrovac ◽  
Marijana Jukić ◽  
...  

Efficient synthesis of 5-aminosulfonyl uracil derivatives 2-9 and results of their antiproliferative activity are provided. Sulfonylation of the amino group in 5-aminouracil 1 with selected arylsulfonyl chlorides occurs regioselectively when the reaction is carried out in pyridine at room temperature. Simple isolation of the products by recrystallization of the crude product mixture from aqueous methanol provides good to excellent yields. The prepared 5-aminosulfonyl uracil derivatives 2-9 were tested for the antiproliferative activity on a panel of seven tumor cell lines of different histological origin (HeLa, Caco-2, NCI-H358, Raji, HuT78, Jurkat, K562) and normal MDCK I cells. Derivatives 2-9 were found more efficient to lymphoma and leukemia cells compared to solid tumor and normal cells.


2013 ◽  
Vol 183 ◽  
pp. 641-647 ◽  
Author(s):  
Hideki Koyanaka ◽  
Yoshikatsu Ueda ◽  
Ken Takeuchi ◽  
Alexander I. Kolesnikov

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