Stereoselective synthesis of novel C-3 functionalized 3-sulfonyl-β-lactams: Promising biologically active heterocyclic scaffolds

Recent synthetic strategies of spiro-azetidin-2-one, -pyrrolidine, -indol(one) and -pyran derivatives-a review

“…2), supported on superparamagnetic Fe 3 O 4 @-SiO 2 nano-particles, enhanced the antibacterial activity in comparison with the corresponding spirocyclic b-lactam, which was supposed to be due to the synergic effect of the Fe 3 O 4 @-SiO 2 /b-lactam combination. 12,13 A number of spiro-azetidinedione derivatives have been tested for anti-breast cancer activity, however, only 3-chloro-1-(o-tolyl)spiro[azetidine-2,3 ′indoline]-2 ′ ,4-dione (VI) (Fig. 2) displayed a signicant cytotoxicity (IC 50 = 22.75-25.18 mM) for breast cancer cell lines, which was comparable to the standard control drug doxorubicin.…”

An update on the synthesis and reactivity of spiro-fused β-lactams

“…14 The spirocyclic β-lactam 157 (Figure 2), supported on superparamagnetic Fe 3 O 4 @SiO 2 nanoparticles, enhanced the antibacterial activity in comparison with the corresponding spirocyclic β-lactam, which was supposed to be due to the synergic effect of the Fe 3 O 4 @SiO 2 /β-lactam combination. 102,103 A number of novel spiro[azetidine-2,3 ' -indole]-2 ' ,4(1 ' H)-dione derivatives have been tested for anti-breast cancer activity, however, only 3-chloro-1-(o-tolyl)spiro[azetidine-2,3'-indoline]-2',4-dione 158 (Figure 2) displayed a significant cytotoxicity (IC 50 = 22.75-25.18 μM) for breast cancer cell lines after 48 h, which is comparable to the standard control drug doxorubicin. 104 Recently, ((2S,3R)-3-hydroxy-2-((R)-5-isobutyryl-1-oxo-2,5-diazaspiro [3.4]octan-2-yl)butanamide) 159 (Figure 2) has been examined for in vitro and in vivo pharmalogical properties.…”

Synthesis of Novel 4-Halomethyl-1,3-oxaselenolane Substituted Spirocyclic Azetidin-2-ones from cis-3-Allyloxy-3-benzylselenoazetidin-2-ones

“…Due to our continuing interest in the design of methods for the synthesis of novel C-3 functionalized azetidin-2-ones [19], we present here the application of cis-3-chloro-3-benzylseleno-β-lactams for the synthesis of novel selenospiro-β-lactams. Studies of the chalcogen (selenium) in which its nucleophilic character has been utilized in the halogen-mediated (I 2 , Br 2 ) intraselenyl cyclization reactions leading to 4-halomethyl-1,3-oxaselenolane substituted spiro-β-lactams from cis-3-allyloxy-3-benzylseleno-β-lactams is investigated.…”