- Synthesis of benzylidenecycloalkan-1-ones and 1,5-diketones under Claisen–Schmidt reaction: Influence of the temperature and electronic nature of arylaldehydes
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Herein, we present the results of the influence of reaction temperature and the electronic nature of arylaldehydes in the reactions of benzocycloalkan-1-ones and arylaldehydes under classical Claisen–Schmidt condensation conditions. The products obtained, 2-arylidene derivatives of benzocycloalkan-1-ones and/or spiropolycyclic-1,5-diketones through multicomponent reactions, depended on the electronic nature of arylaldehyde and the reaction temperature. Besides, under identical conditions, 2-arylideneindan-1-ones afforded bis-indane-1,5-diketones through a process that involves Michael addition reaction, which is also dependent on the temperature. Theoretical studies using density-functional theory allowed understanding the chemical reactivity and the site selectivity of α,β-enones used in this work through the calculation of global and local electrophilicity on C–β. Both the electrophilicity of C-β and the temperature led the course of reaction toward the formation of aldol condensation, aldol condensation/Michael addition, and aldol condensation/dimerization products. This work is the first to perform the structural and configurational assignments of bis-indane-1,5-diketones.
- Lanta?o, Beatriz,Aguirre, José M.,Drago, Eleonora V.,Bollini, Mariela,de la Faba, Diego J.,Mufato, Jorge D.
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- Regiodivergent synthesis of vinyl trifluoromethansulfonates γ/δ lactones: Via 1,6 addition/intramolecular one-pot annulation of 1,4-dihidropyridines derivated from pyridinyl propenones
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We report a novel intramolecular 1,6 oxa-Michael addition on substituted dihydropyridines to obtain 5 and 6 member ring lactones in an one-pot reaction starting from activated pyridinyl propenones, without organic catalysis or presence of bulky groups in
- álvarez-Toledano, Cecilio,Ballinas-Indili, Ricardo,Carmona-Reyes, Genaro,Sánchez-Vergara, María Elena,Toscano, R. Alfredo
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supporting information
(2021/12/29)
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- In vitro Anti-Trypanosomal Activities of Indanone-Based Chalcones
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Human African trypanosomiasis is a neglected infectious disease that affects mostly people living in the rural areas of Africa. Current treatment options are limited to just four drugs that have been in use of four to nine decades. The life-threatening to
- Beteck, Richard M.,Legoabe, Lesetje J.,Isaacs, Michelle,Hoppe, Heinrich C.
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p. 337 - 341
(2019/06/10)
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- Discovery and structure-activity relationship studies of 2-benzylidene-2,3-dihydro-1H-inden-1-one and benzofuran-3(2H)-one derivatives as a novel class of potential therapeutics for inflammatory bowel disease
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To develop effective therapeutics for inflammatory bowel disease (IBD), 2-benzylidene-2,3-dihydro-1H-inden-1-one and benzofuran-3(2H)-one derivatives, were designed and synthesized and their structure-activity relationships (SAR) were investigated. Compounds 7, 25, 26, 32, 39, 41, 52, 54, and 55 showed potent inhibitory effect (>70%) on the TNF-α-induced adhesion of monocytes to colon epithelial cells, which is one of the hallmark events leading to IBD. Such inhibitory activity of the compounds correlated with their suppressive activities against the TNF-α-induced production of ROS; ICAM-1 and MCP-1 expression, critical molecules involved in monocyte-epithelial adhesion; and NF-κB transcriptional activity. In addition, compounds 41 and 55 significantly suppressed the lipopolysaccharide (LPS)-induced expression of the TNF-α gene, with compound 55 showing better efficacy. This inhibition of TNF-α expression by compounds 41 and 55 corresponded to their additional inhibitory activity against AP-1 transcriptional activity, which is another transcription factor required for high level TNF-α expression. The strong inhibitory activity of compound 55 against an in vivo colitis model was confirmed by its dose-dependent inhibitory activity in a rat model of 2,4,6-trinitrobenzenesulfonic acid (TNBS)-induced colitis, demonstrating compound 55 as a new potential candidate for the development of therapeutics against IBD.
- Kadayat, Tara Man,Banskota, Suhrid,Gurung, Pallavi,Bist, Ganesh,Thapa Magar, Til Bahadur,Shrestha, Aarajana,Kim, Jung-Ae,Lee, Eung-Seok
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supporting information
p. 575 - 597
(2017/06/23)
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- 2-Heteroarylidene-1-indanone derivatives as inhibitors of monoamine oxidase
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In the present study a series of fifteen 2-heteroarylidene-1-indanone derivatives were synthesised and evaluated as inhibitors of recombinant human monoamine oxidase (MAO) A and B. These compounds are structurally related to series of heterocyclic chalcone derivatives which have previously been shown to act as MAO-B specific inhibitors. The results document that the 2-heteroarylidene-1-indanones are in vitro inhibitors of MAO-B, displaying IC50 values of 0.0044–1.53?μM. Although with lower potencies, the derivatives also inhibit the MAO-A isoform with IC50 values as low as 0.061?μM. An analysis of the structure-activity relationships for MAO-B inhibition indicates that substitution with the methoxy group on the A-ring leads to a significant enhancement in MAO-B inhibition compared to the unsubstituted homologues while the effect of the heteroaromatic substituent on activity, in decreasing order is: 5-bromo-2-furan?>?5-methyl-2-furan?>?2-pyridine?≈?2-thiophene?>?cyclohexyl?>?3-pyridine?≈?2-furan. It may therefore be concluded that 2-heteroarylidene-1-indanone derivatives are promising leads for the design of MAO inhibitors for the treatment of Parkinson's disease and possibly other neurodegenerative disorders.
- Nel, Magdalena S.,Petzer, Anél,Petzer, Jacobus P.,Legoabe, Lesetja J.
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- Synthesis, topoisomerase I and II inhibitory activity, cytotoxicity, and structure-activity relationship study of 2-phenyl- or hydroxylated 2-phenyl-4-aryl-5H-indeno[1,2-b]pyridines
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Abstract A series of novel twenty-eight rigid 2-phenyl- or hydroxylated 2-phenyl-4-aryl-5H-indeno[1,2-b]pyridines were synthesized and evaluated for their topoisomerase inhibitory activity as well as their cytotoxicity against several human cancer cell li
- Kadayat, Tara Man,Song, Chanju,Shin, Somin,Magar, Til Bahadur Thapa,Bist, Ganesh,Shrestha, Aarajana,Thapa, Pritam,Na, Younghwa,Kwon, Youngjoo,Lee, Eung-Seok
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p. 3499 - 3512
(2015/08/03)
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