A facile chemo-, regio- and stereoselective synthesis and cholinesterase inhibitory activity of spirooxindole–pyrrolizine–piperidine hybrids

Kia, Yalda; Osman, Hasnah; Kumar, Raju Suresh; Murugaiyah, Vikneswaran; Basiri, Alireza; Perumal, S.; Razak, Ibrahim Abdul

doi:10.1016/j.bmcl.2013.03.027

Cited by 70 publications

(32 citation statements)

References 25 publications

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“…3,5-Bis(arylidene)-4-piperidone derivatives constitute an important class of therapeutic agents exhibiting anticancer 12 , antioxidant 13 and anticholinesterase 14 properties as well. Prompted by the above findings and in continuation of our interest in the biological activities of 3,5-bis(arylidene)-4-piperidone 15 , we thought it worthwhile to incorporate the bioactive heterocycle piperidone moiety into α,β -unsaturated ketone mimics with the hope that the piperidone residue may serve as both the donor and acceptor in hydrogen-bonding interactions to improve binding affinity and also to verify its importance for the DEN2 serine protease inhibitory activity (Fig. 1).…”

Section: Introductionmentioning

confidence: 76%

3,5-Bis(arylidene)-4-piperidones as potential dengue protease inhibitors

Osman

Idris

Kamarulzaman

et al. 2017

Acta Pharmaceutica Sinica B

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Dengue is a severe mosquito-borne viral infection causing half a million deaths annually. Dengue virus NS2B/NS3 protease is a validated target for anti-dengue drug design. A series of hitherto unreported 3,5-bis(arylidene)-4-piperidones analogues 4a—4j were synthesized and screened in silico against DENV2 NS2B/NS3 protease to elucidate their binding mechanism and orientation around the active sites. Results were validated through an in vitro DENV2 NS2B/NS3 protease assay using a fluorogenic Boc-Gly-Arg-Arg-AMC substrate. Nitro derivatives of 3,5-bis(arylidene)-4-piperidones (4e and 4j) emerged as promising lead molecules for novel protease inhibitors with an IC50 of 15.22 and 16.23 µmol/L, respectively, compared to the standard, panduratin A, having IC50 of 57.28 µmol/L.

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Section: Introductionmentioning

confidence: 76%

3,5-Bis(arylidene)-4-piperidones as potential dengue protease inhibitors

Osman

Idris

Kamarulzaman

et al. 2017

Acta Pharmaceutica Sinica B

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“…Nitrogen‐containing heterocycles and carbocycles are important structural motifs due to their frequent presence in many biologically active natural products and pharmaceutically relevant molecules . In particular, multifunctional polycyclic spiropyrrolidine represents a privileged heterocyclic skeleton that exists in a large family of naturally occurring alkaloids and synthetic products exhibiting a plethora of biological activities such as antimicrobial , antimycobacterial , anticancer , local anesthetic , anti‐inflammatory, analgesic , and acetylcholinesterase (AChE) inhibition activities . On the other hand, indanone subunits are important core structures of numerous natural and synthetic products endowed with diverse bioactivities .…”

Section: Introductionmentioning

confidence: 99%

Straightforward and Highly Diastereoselective Synthesis of a New Set of Functionalized Dispiropyrrolidines Involving Multicomponent 1,3‐Dipolar Cycloaddition with Azomethine Ylides

Boudriga

Elmhawech

Askri

2019

Journal of Heterocyclic Chem

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The diastereoselective synthesis of novel series of dispiropyrrolidines has been achieved by a one‐pot three‐component [3 + 2] cycloaddition reaction of (E)‐2‐arylideneindanones, glycine ethyl ester, and the cyclic diketones 1H‐indole‐2,3‐dione (isatin) or acenaphthenequinone. Moreover, we disclose an unprecedented epimerization of spiroadducts leading to a new family of dispiropyrrolidines with an unusual relative stereochemistry.

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“…It has reported that the equimolar amounts of isatins 1 , sarcosine and 4‐aryl‐4‐oxo‐2‐butenoic acids 2 or chalcones 3 in boiling aqueous methanol (1:3) afforded exclusively the spirooxindoles via The multicomponent 1,3‐dipolar cycloaddition (MCDC). The authors wanted to prepare the new spirooxindoline derivatives having a high HOMO energy value to increase the efficiency as antioxidant reagents.…”

Section: Resultsmentioning

confidence: 99%

One‐pot Synthesis of Novel Spirooxindoles as Antibacterial and Antioxidant Agents

El‐Hashash

Rizk

2016

Journal of Heterocyclic Chem

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The regioselective spiroindoline derivatives were afforded via multi‐componant reaction. Its process was one of the green chemistry (simplicity, mild conditions, and atomic economy). The electron repelling and attracting groups affected on reactivity of the azomethine ylides (increase EHOMO value). All compound structures were confirmed by spectroscopic data and elemental analysis. The antibacterial and antioxidant activities for these synthesized compounds could be investigated; the highly antioxidant activity was observed with compounds, which proved to possess high HOMO values, and the highly antibacterial activity was observed against S. aureus, B. cereus, S. marcesens, and P. mirabilis, which proved to possess low HOMO values.

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A facile chemo-, regio- and stereoselective synthesis and cholinesterase inhibitory activity of spirooxindole–pyrrolizine–piperidine hybrids

Cited by 70 publications

References 25 publications

3,5-Bis(arylidene)-4-piperidones as potential dengue protease inhibitors

3,5-Bis(arylidene)-4-piperidones as potential dengue protease inhibitors

Straightforward and Highly Diastereoselective Synthesis of a New Set of Functionalized Dispiropyrrolidines Involving Multicomponent 1,3‐Dipolar Cycloaddition with Azomethine Ylides

One‐pot Synthesis of Novel Spirooxindoles as Antibacterial and Antioxidant Agents

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