2019
DOI: 10.1039/c9ra05661k
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Synthesis, human topoisomerase IIα inhibitory properties and molecular modeling studies of anti-proliferative curcumin mimics

Abstract: Piperidinecarboxamides (curcumin mimics) show promising anti-proliferative properties against HCT116 (colon), MCF7 (breast) and A431 (squamous skin) carcinoma cell lines with potency higher than that of 5-fluorouracil.

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Cited by 14 publications
(18 citation statements)
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“…The acid chlorides 3a,b [74] , [75] were obtained from the corresponding acetylsalicylic acids 2a,b [76] by the reported procedure [oxalyl chloride in dichloromethane containing a catalytic amount of N - N -dimethylformamide (DMF)]. Reaction of the 3 E , 5 E -bis(arylidene)-4-piperidones 4a–i [15] , [16] , [77] , [19] , [78] with the appropriate 3a,b in DMF in presence of sufficient amount of triethylamine in an ice-cold water bath afforded the targeted conjugates 5a–p in acceptable yields (60–88 %) ( Scheme 1 ). IR spectrum of 5a (an example of the targeted family) reveals the piperidinyl ketonic and salicylate amidic carbonyls at ν = 1767, 1643 cm -1 , respectively.…”
Section: Resultsmentioning
confidence: 99%
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“…The acid chlorides 3a,b [74] , [75] were obtained from the corresponding acetylsalicylic acids 2a,b [76] by the reported procedure [oxalyl chloride in dichloromethane containing a catalytic amount of N - N -dimethylformamide (DMF)]. Reaction of the 3 E , 5 E -bis(arylidene)-4-piperidones 4a–i [15] , [16] , [77] , [19] , [78] with the appropriate 3a,b in DMF in presence of sufficient amount of triethylamine in an ice-cold water bath afforded the targeted conjugates 5a–p in acceptable yields (60–88 %) ( Scheme 1 ). IR spectrum of 5a (an example of the targeted family) reveals the piperidinyl ketonic and salicylate amidic carbonyls at ν = 1767, 1643 cm -1 , respectively.…”
Section: Resultsmentioning
confidence: 99%
“…The diene connected through a carbonyl group forming a five-carbon system seems an acceptable approach for developing a biologically enhanced scaffold [12] , [13] , [14] . 3,5-Diylidene-4-piperidones are curcumin mimics with broad promising biological properties of which antitumor against diverse cancer cell lines [15] , [16] , [17] , [18] and anti-inflammatory [19] . The present study deals with synthesis of 3,5-bis(arylidene)-4-piperidones as curcumin mimics conjugated with acetylsalicylic acid (aspirin) ( Fig.…”
Section: Introductionmentioning
confidence: 99%
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“…Computational structural optimization study [DFT, B3LYP/6-31G (d,p)] was considered in the present study. [32,33] This is very useful for identifying the effect(s) of solid/crystalline state on the chemical structure identified relative to the free/gaseous state (supplementary material Figure S1, Tables S1, S2). Comparing the values of bond lengths and angles of the optimized molecules with those obtained experimentally, they are in very good agreement only with minor differences.…”
Section: Computational Structural Optimization Studymentioning
confidence: 99%
“…In our pursuit to develop novel antitumor agents [11] , [12] , [13] , the present study describes the synthesis of 3-alkenyl-2-oxindoles conjugated with sulfonamide function. This fragment is an important component in many clinically approved antitumor drugs {e.g.…”
Section: Introductionmentioning
confidence: 99%