77795-21-2Relevant academic research and scientific papers
Ferulic acid amide derivatives with varying inhibition of amyloid-β oligomerization and fibrillization
Kolaj, Igri,Wang, Yanfei,Ye, Kailin,Meek, Autumn,Liyanage, S. Imindu,Santos, Clarissa,Weaver, Donald F.
, (2021/07/07)
Alzheimer's disease (AD) is a progressive neurodegenerative disorder characterized, in part, by the misfolding, oligomerization and fibrillization of amyloid-β (Aβ). Evidence suggests that the mechanisms underpinning Aβ oligomerization and subsequent fibrillization are distinct, and may therefore require equally distinct therapeutic approaches. Prior studies have suggested that amide derivatives of ferulic acid, a natural polyphenol, may combat multiple AD pathologies, though its impact on Aβ aggregation is controversial. We designed and synthesized a systematic library of amide derivatives of ferulic acid and evaluated their anti-oligomeric and anti-fibrillary capacities independently. Azetidine tethered, triphenyl derivatives were the most potent anti-oligomeric agents (compound 2i: IC50 = 1.8 μM ± 0.73 μM); notably these were only modest anti-fibrillary agents (20.57% inhibition of fibrillization), and exemplify the poor correlation between anti-oligomeric/fibrillary activities. These data were subsequently codified in an in silico QSAR model, which yielded a strong predictive model of anti-Aβ oligomeric activity (κ = 0.919 for test set; κ = 0.737 for validation set).
Palladium hydroxide catalyzed transformation of primary propargylic alcohols into aldehydes: Application to the synthesis of the tetrahydrofuran core
Sabitha, Gowravaram,Reddy, A.Yagundar,Nayak, Sambit,Yadav, Jhillu S.
experimental part, p. 1657 - 1662 (2012/07/03)
A palladium-catalyzed one-pot, two-step sequence involving redox isomerization/reduction of primary propargylic alcohols into the corresponding aldehydes has been achieved at room temperature for the first time in good to excellent yields under mild conditions. The functional group compatibility in this reaction is studied and this new methodology has been successfully applied in the synthesis of the 2,5-trans-tetrahydrofuran ring system of amphidinolides. It is noteworthy that aromatic substituted propargylic alcohols gave a mixture of unsaturated and saturated aldehydes, whereas aliphatic propargylic alcohols gave only saturated aldehydes. Georg Thieme Verlag Stuttgart · New York.
Structure-activity relationship of piperine and its synthetic analogues for their inhibitory potentials of rat hepatic microsomal constitutive and inducible cytochrome P450 activities
Koul, Surrinder,Koul, Jawahir L.,Taneja, Subhash C.,Dhar, Kanaya L.,Jamwal, Deshvir S.,Singh, Kuldeep,Reen, Rashmeet K.,Singh, Jaswant
, p. 251 - 268 (2007/10/03)
Inhibitors of drug metabolism have important implications in pharmaco- toxicology and agriculture. We have reported earlier that piperine, a major alkaloid of black and long peppers inhibits both constitutive and inducible cytochrome P450 (CYP)-dependent drug metabolising enzymes. In the present study, an attempt has been made to prepare several novel synthetic analogues so as to relate various modifications in the parent molecule to the inhibition of CYP activities. Two types of mono-oxygenase reactions arylhydrocarbon hydroxylase (AHH) and 7-methoxycoumarin-O-demethylase (MOCD) have been studied. Inhibition studies were investigated in rat microsomal fraction prepared from untreated, 3MC- and PB- treated rat liver in vitro. Modifications were introduced into the piperine molecule: (i) in the phenyl nucleus, (ii) in the side chain and (iii) in the basic moiety. Thus, 38 compounds have been subjected to such studies, and simultaneously an attempt has also been made to arrive at the structure-activity relationship of synthetic analogues. In general, most of the inhibitory potential of the parent molecule is lost with modification in either of the three components of piperine. Saturation of the side chain resulted in significantly enhanced inhibition of CYP while modifications in the phenyl and basic moieties in few analogues offered maximal selectivity in inhibiting either constitutive or inducible CYP activities. Thus few novel analogues as CYP inactivators have been synthesized which may have important consequences in pharmacokinetics and bioavailability of drugs. (C) 2000 Elsevier Science Ltd.
Structure and Synthesis of New Phenolic Amides from Piper nigrum L.
Inatani, Reiko,Nakatani, Nobuji,Fuwa, Hidetsugu
, p. 667 - 674 (2007/10/02)
New phenolic amides, N-trans-feruloyl piperidine (4a), N-5-(4-hydroxy-3-methoxyphenyl)-2E,4E-pentadienoyl piperidine (5a) and N-5-(4-hydroxy-3-methoxyphenyl)-2E-pentenoyl piperidine (6a) were isolated from the fruit of white pepper (Piper nigrum L.).The f
