Spiro indolinone beta-lactams, inhibitors of poliovirus and rhinovlrus 3C-proteinases

Synthesis of spiro-1,2,4-triazole-3-thiones from cycloalkanone thiosemicarbazones, and formation of a cyclic 1,2-dithione

“…A series of spiro-cycloalkylidene [1,2,4]triazole-3-thione derivatives was synthesized via oxidative cyclization of cyclic-ylidene-N-substituted hydrazinecarbothioamides by using benzoand naphthoquinone derivatives. The simple reactivity of cycloalkylidene-N-substituted hydrazinecarbothioamides required the availability of cyclic-C=N and the nucleophilic sites thioamide-NH , s. It was found that solvent, temperature and the molar ratio of reactants may all play a critical role in the reaction efficiency.…”

“…1 Also, heterocyclic 1,2,4-triazoline-5-thione derivatives exhibited various biological properties such as analgesic, 2 anti-inflammatory, 3 bacteriostatic 4 and antimitotic 5 activities.…”

Crystal structure of 2-spiro-3′-(2-oxindole)-3-benzoyl-4-phenyl-5- hydroxymethylpyrrolidine, C25H22N2O3

“…Spiro[pyrrolidine-2,3'-oxindole] ring system is as tructural feature found in aw ide variety of oxindole alkaloids, such as horsfiline 1 [1] and spirotryprostatin B [2], which have been reported to behave as aldose reductase, poliovirus, and rhinovirus 3C-proteinase inhibitors [3]. The 1,3-dipolar cycloaddition reaction has also been employed for the construction of spiro-[pyrrolidine-2,3'-oxindoline] derivatives.…”

Synthesis of novel spiro fused polycyclic β-lactam derivatives

“…Numerous heterocycle-fused β-lactam derivatives have been synthesized and assayed for biological activities. 1,4,5 Recently, spiro-β-lactams became particularly interesting compounds because their antiviral 7 and antibacterial properties 8 as well as their inhibition of cholesterol absorption 9 make them potentially useful candidates for drug development. They can also be used as β-turn mimetics in peptide chemistry [10][11][12] and, particularly 4-spiro-β-lactams, are synthetic precursors for cyclic α,α-disubstituted β-amino acids and peptide derivatives.…”

“…Several synthetic methods for spiro-β-lactams have been developed. [7][8][9][10][11] Among these, the cyclic ketene-participating Staudinger reaction is one of important strategies. derivatives of benzothiazepines, benzodiazepines, and dibenzo[b,f]oxazepines because of their potential biological and pharmaceutical importance.…”