Phenylpropanoid amides and phenylethanols from Nanophyton erinaceum

Han, Jianxin; Li, Liya; Han, Li Hao; Huang, Xueshi; Yuan, Tao

doi:10.1016/j.bse.2015.07.012

Cited by 4 publications

(4 citation statements)

References 10 publications

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“…Additionally, the correlations of H-7′ ( δ 4.73)/H-8′ ( δ 3.45 and 3.54) in the COSY experiment further confirmed the position of the hydroxyl group at C-7′. 27…”

Section: Resultssupporting

confidence: 52%

Possible neuroprotective effects of amide alkaloids from Bassia indica and Agathophora alopecuroides: in vitro and in silico investigations

et al. 2022

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“…Additionally, the correlations of H-7′ ( δ 4.73)/H-8′ ( δ 3.45 and 3.54) in the COSY experiment further confirmed the position of the hydroxyl group at C-7′. 27…”

Section: Resultssupporting

confidence: 52%

Possible neuroprotective effects of amide alkaloids from Bassia indica and Agathophora alopecuroides: in vitro and in silico investigations

et al. 2022

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“…us, developing and testing of new compounds with leishmanicidal activity is of paramount importance to improve disease treatment and control. Several medicinal plant secondary metabolites have shown interesting antileishmanial activities, including alkaloids, steroids, terpenoids, phenolic acids, and phenylpropanoids [13][14][15].…”

Section: Anti-leishmania Activity Of Compounds 5-36mentioning

confidence: 99%

“…For this study, a series of 32 analogues of 1 (Scheme 1) were synthesized, preserving the (E)-3-(3,4,5-trimethoxyphenyl)-acryloyl moiety on cinnamic esters and amides and changing this moiety on benzoic esters by removing the ethylene group between carbons 2 and 3. Side-chain modi cations were also evaluated changing the radical R to methyl (5), ethyl (6), propyl (7), iPr (8), butyl (9), pentyl (10), decyl (11), 2-methoxyethyl (12), 4-methoxybenzyl (13), phenylethyl (14), 4-methylphenylethyl (15), carvacryl (16), CHPh 2 (17), furfuryl (18), eugenyl (19), (−)-bornyl (20) and piperonyl (21) on cinnamic esters, and butyl (22), N,N-diethyl (23), octyl (24), cyclohexyl (25) benzyl (26), pyrrolidyl (27), 4-methylbenzyl (28), 4-methoxybenzyl (29), 4-uorobenzyl (30), 4-chlorobenzyl (31), 4-bromobenzyl (32) 2,4-dimethoxybenzyl (33), and 3,4-dimethoxybenzyl (34) on amides. e benzoic esters synthetized were 2methoxyethyl-3,4,5-trimethoxybenzoate (35) and benzyl 3,4,5-trimethoxybenzoate (36) [8][9][10][11][12].…”

Section: Introductionmentioning

confidence: 99%

Design, Antileishmanial Activity, and QSAR Studies of a Series of Piplartine Analogues

Nóbrega

Silva

Filho

et al. 2019

Journal of Chemistry

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Piplartine is an alkamide found in different Piper species and possesses several biological activities, including antiparasitic properties. Thus, the aim of the present study was to evaluate a series of 32 synthetic piplartine analogues against the Leishmania amazonensis promastigote forms and establish the structure-activity relationship and 3D-QSAR of these compounds. The antileishmanial effect of the compounds was determined using the MTT method. Most compounds were found to be active against L. amazonensis. Among 32 assayed derivatives, compound (E)-(−)-bornyl 3-(3,4,5-trimethoxyphenyl)-acrylate exhibited the most potent antileishmanial activity (IC50 = 0.007 ± 0.008 μM, SI > 10), followed by benzyl 3,4,5-trimethoxybenzoate (IC50 = 0.025 ± 0.009 μM, SI > 3.205) and (E)-furfuryl 3-(3,4,5-trimethoxyphenyl)-acrylate (IC50 = 0.029 ± 0.007 μM, SI > 2.688). It was found that the rigid substituents contribute to increasing antiparasitic activity against L. amazonensis promastigotes. The presence of the unsaturated heterocyclic substituent in the phenylpropanoid chemical structure (furfuryl group) resulted in a bioactive derivative. Molecular simplification of benzyl 3,4,5-trimethoxybenzoate by omitting the spacer group contributed to the bioactivity of this compound. Furthermore, bornyl radical appears to be important for antileishmanial activity, since (E)-(−)-bornyl 3-(3,4,5-trimethoxyphenyl)-acrylate exhibited the most potent antileishmanial activity. These results show that some derivatives studied would be useful as prototype molecules for the planning of new derivatives with profile of antileishmanial drugs.

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“…The chemical structure of 2 was assigned with the aid of HSQC (Table 1) Figure 1. Compound 2 were previously isolated from various plant such as Tetrastigma hemsleyanum [13], Nanophyton erinaceum [14] and Laurus nobilis [12]. It was reported to have antioxidant and hepatoprotective effects [15].…”

Section: Resultsmentioning

confidence: 99%