Search

Sudan is a rich country in wild plants that play significant roles in securing food and medicine in rural areas, especially. This study explored Sarcocephalus latifolius (African peach) and Vitex doniana (black plum) for their fruits' proximate composition, minerals, total soluble phenols, phenolic acids, total carotenoids, lutein, β–carotene, α–tocopherol, δ–tocopherol and total antioxidant capacity. African peach fruit and black plum pulp showed total soluble phenols amounting to 16.89 mg gallic acid equivalents (GAE)/g of Dry Weight (DW) and 7.56 mg GAE/g DW, respectively. The paramount phenolic acids were cinnamic acid (895 mg/kg DW) in African peach fruit and protocatechuic acid (1200 mg/kg DW) in black plum pulp. Total antioxidant capacities reached 268 µmoles trolox equivalents (TE)/g DW in African peach and 214 µmoles TE/g DW in black plum, when measured from hydrophilic extracts (HPE) using 2, 2-DiPhenyl-1-PicrylHydrazyl (DPPH) assay. The contents of total carotenoid were 47 mg/kg DW and 22.6 mg/kg DW, lutein reached 18.50 mg/kg DW and 15 mg/kg DW whereas β–carotene showed 0.31 mg/kg DW and 0.23 mg/kg DW in African peach and black plum, respectively. African peach showed α–tocopherol (167 mg/kg DW) whereas black plum showed δ–tocopherol (398 mg/kg DW). From this study, we concluded that African peach fruit and black plum pulp could be good sources of nutrition and antioxidants and have high potential for human health. [ABSTRACT FROM AUTHOR]

A series of novel piperazine based cinnamic acid bearing coumarin derivatives were designed and synthesized by piperazine based cinnamic acids esterification with 4‐hydroxycoumarin and characterized by various spectral techniques like infrared, 1H nuclear magnetic resonance (NMR), 13C NMR, and mass. The novel bioactive compounds (7a‐7m) screen their potential against different bacterial and fungal strains. Compound 7g (minimum inhibitory concentration [MIC] = 12.5 µg/ml) exhibited potent antibacterial activity against Escherichia coli strain. Compounds 7d, 7f, 7g, 7k, 7l, and 7m showed potent antibacterial activity against all bacterial strains. Compounds 7a, 7g, 7h, 7k, 7l, and 7m exhibited potent antifungal activity against all fungal strains. Furthermore, a molecular docking study revealed that compounds 7d, 7f, 7g, and 7k could bind to the active site of E. coli DNA gyrase subunit B protein and form hydrogen bonding with crucial amino acid residues Arg136 in the active sites. Comprehensively, our study recommends that 7d, 7f, 7g, and 7k could be a promising lead for developing more efficient antimicrobial drug candidates and DNA gyrase inhibitors. [ABSTRACT FROM AUTHOR]

Here we report the design, synthesis and evaluation of dihydropyrimidinones (DHPMs)‐cinnamic acids hybrids as potential anti‐cancer compounds. The synthetic route was successfully performed and the products obtained in good to excellent yields. These compounds were tested against LNCaP and PC‐3 metastatic prostate cancer cells and RWPE‐1 prostate cells. The results indicate that hybridization was effective, since the hybrids were much more cytotoxic than DHPMs and cinnamic acids evaluated separately. Compound 3 a was the most potent hybrid against PC‐3 cells (IC50 of 15.7 μM) and LNCaP cells (IC50 of 11.5 μM) and was further optimized by bioisosterism and molecular simplification strategies leading to three new analogues (5, 7 and 8). Compounds 3 a, 7 and 8 showed an antiproliferative effect against PC‐3 cells without inducing cell death nor cell cycle arrest. The mechanism of action of compound 8 was further investigated. The results indicated that compound 8 inhibits autophagic flux, and this effect could be linked to the antiproliferative activity. Moreover, in silico prediction of some molecular properties related to pharmacokinetics showed that all the hybrids meet the criteria for a drug prototype to have a good absorption and permeation for oral administration. These results highlight the potential use of DHPMs‐cinnamic acids hybrids as antiproliferative agents for further evaluation of the antitumor activity in vivo. [ABSTRACT FROM AUTHOR]

A Hf(IV) metal‐organic framework (MOF) with di‐amino functionalized linker was obtained as a crystalline solid with UiO‐67 topology under solvothermal reaction conditions. The guest free form of Hf(IV) MOF (1′) was efficiently employed as a heterogeneous catalyst to synthesize cinnamic acid derivatives via Knoevenagel‐Doebner reaction for the first time. The catalyst (1′) was efficiently active to directly achieve cinnamic acid from benzaldehyde and malonic acid. The solid retained its activity up to 6th cycle with no decay in its activity. The noticeable advantages of the catalyst are its milder reaction conditions, high yield, high stability, recyclable nature towards catalysis and wide substrate scope as well as shape‐selective behaviour. The possible mechanism of the reaction was also studied thoroughly with suitable control experiments. [ABSTRACT FROM AUTHOR]

Two novel benzoylthioureas derived from gallic acid, (tri‐O‐acetyl)galloyl‐N,N‐diethylthiourea HL1, and cinnamic acid, cinnamoyl‐N,N‐diethylthiourea HL2 have been successfully prepared and characterized by means of elemental analysis, IR, NMR, high‐resolution MS, and X‐ray crystallography. The organic ligands react with Ni(AcO)2 and Cu(AcO)2 in MeOH under formation of bis‐complexes with the compositions of [M(L)2] (M=Ni2+, Cu2+; L=L1, L2). Similar reactions with Co(AcO)2, however, result in Co(III) tris‐complexes [Co(L)3] (L=L1, L2) with the metal ions oxidized presumably by atmospheric dioxygen. X‐ray crystallography and spectroscopic characterization reveal a cis square‐planar coordination in the bis‐complexes and facial octahedral geometry in the tris‐complexes. In all of metal complexes, the deprotonated organic compounds ({L1}− and {L2}−) serve as (S,O)‐bidentate ligands. The ligand HL1 and its Ni(II) and Cu(II) complexes exhibit weak antiproliferative effects on the human MCF7 breast and HepG2 liver cancer cells with IC50 values in the range of 60–115 μM. Surprisingly, the tris‐complex [Co(L1)3] exhibits high cytotoxicity with IC50 values of 22.23±1.58 μM for MCF7 and 28.30±3.09 μM for HepG2 cancer cells. The activity against MCF7 cells is even more than that of cisplatin under the same conditions. [ABSTRACT FROM AUTHOR]

Abstract: ((E)‐N‐salicylidene)‐hydrazide (HL) was synthesised from the condensation of cinnamic acid hydrazide with salicylaldehyde and it was utilised as a fluorescent and colorimetric sensor for dual detection of Zn(II) and Al(III) ions. The solid‐state structure of the ligand (HL) was stabilised by two‐dimensional supramolecular network as evident from single crystal X‐ray diffraction data. In solution the probe was found to have greater relative binding affinity and sensitivity towards Al(III) ion over Zn(II) ion. While the probe demonstrated very fast colorimetric response towards Zn(II) ion in solid state, it had superior fluorimetric sensitivity to Al(III) ion in solution by exhibiting distinct spectral changes. This unique phase dependent property of the probe has been exploited to easily detect Al(III) and Zn(II) ions. The above mentioned metal ions formed 2 : 1 (L : M) complexes with the probe which was supported by absorption and emission titration studies, Job′s Plot and ESI mass spectral analysis. Most of the experimental outcomes were well supported by theoretical calculations. [ABSTRACT FROM AUTHOR]

The great success of cinnamic acids was rooted in their multiple functional groups. Herein, reactions triggered by the radical addition, electrophilic addition, Michael addition and reactions of acids were thoroughly discussed and summarized. Multi‐component reactions, rearrangements, stereoselective synthesis, coupling, additions will be depicted in detail. This review focused on advances of cinnamic acids in the last decade (2010–2020). We hope this review will be good for a better understanding of these reagents and future research. [ABSTRACT FROM AUTHOR]

A facile and efficient methodology for the synthesis of cinnamides has been achieved under metal‐ and additive‐free conditions. This method allows the efficient C–N cross‐coupling of diverse cinnamic acids with tetraalkylthiuram disulfides through a simply mixing operation in 1,2‐dichloroethane at 100 °C. The protocol provides a direct approach to cinnamides and is featured with readily available starting materials and broad substrate scope, which shows its practical synthetic value in organic synthesis. [ABSTRACT FROM AUTHOR]

The aim of this study was to develop a validated high-performance thin-layer chromatography (HPTLC) procedure for resolution of chemical constituents and identification and quantification of two selected natural anticancer compounds, stigmasterol (PD-1) and cinnamic acid (PD-2), in Pluchea dioscoridis chloroform fraction (PDCF). The chromatographic estimations were conducted on normal HPTLC (20 cm × 10 cm glass-backed silica gel 60 F254) plates with chloroform methanol acetic acid (93:5:2, V/V) used as the mobile phase. para-Anisaldehyde was used for the derivatization of the developed plate, and compact spots were scanned at hmax = 513 nm. A well resolved, compact, and intense peaks of PD-1 and PD-2 were recorded at RF = 0.57 and 0.19, respectively. The proposed analytical method for both biomarker compounds was found to be handy, simple, precise, linear (%RSD = 1.03-1.45), accurate (98.91-99.14%), reliable, and sensitive for the analysis of both biomarkers. The LOD/LOQ (ng) for PD-1 and PD-2 were recorded as 38.73/117.37 and 42.58/129.04, respectively, in the linearity range of 200-1400 ng per spot. The obtained result showed maximum quantities of PD-1 and PD-2 (5.36 and 16.98 µg mg-1, respectively). The developed HPTLC was found to be suitable for the routine analysis of these 2 biomarkers in the chloroform fraction of Pluchea dioscoridis and can be further employed in the process quality control of herbal formulations containing the said biomarkers. [ABSTRACT FROM AUTHOR]

The first workable application of β-nitrostyrenes and CBr4 as coupling partners for a highly stereoselective synthesis of (E)-cinnamic acids under visible light photoredox catalysis is reported. The reaction involves a radical denitrative tribromomethylation/hydrolysis cascade to afford (E)-cinnamic acids in excellent yields at room temperature in a one-pot procedure. Moreover, the implementation of visible light as a clean and inexpensive energy source and CBr4 as the latent source of carboxylic groups makes the protocol reconcilable with the present day scenario of organic synthesis. [ABSTRACT FROM AUTHOR]

Photophysical properties and photochemistry of various substituted cinnamates and cinnamic acids for ultraviolet B blocking were investigated experimentally and theoretically. This series includes monohydroxy, -nitro, and -fluoro derivatives. The absorption spectra were satisfactorily reproduced by the direct SAC-CI method with respect to the peak position and intensity. The transition character of the low-lying two ππ* and σπ* states for these 18 derivatives was analyzed. The para derivatives have a different transition character of the ππ* transitions compared with those of the ortho and meta derivatives. To elucidate the relaxation mechanism, the emission spectra were observed with oxygen quenching and the photostability was examined experimentally. The calculated radiative lifetimes indicate that the ortho- and meta-substituted derivatives have longer lifetimes for emission than the para derivatives. The potential energy curves of the first and second singlet excited states of the hydroxy derivatives as well as the vertical singlet and triplet transitions were examined to investigate the relaxation qualitatively. The ortho and meta derivatives have an energy barrier or flat surface in S1 resulting in fluorescence, whereas the para derivatives show nonradiative decay without an energy barrier. The para-hydroxy derivative was found to be an excellent UV absorber based on its broad absorption in the UVB/UVA regions, less emission, and higher photostability. [ABSTRACT FROM AUTHOR]