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1.
Om P. Mishra Nicholas Simmons Sonia Tyagi Ralph Pietrofesa Vladimir V. Shuvaev Roman A. Valiulin Philipp Heretsch K.C. Nicolaou Melpo Christofidou-Solomidou 《Bioorganic & medicinal chemistry letters》2013,23(19):5325-5328
Secoisolariciresinol diglucosides (SDGs) (S,S)-SDG-1 (major isomer in flaxseed) and (R,R)-SDG-2 (minor isomer in flaxseed) were synthesized from vanillin via secoisolariciresinol (6) and glucosyl donor 7 through a concise route that involved chromatographic separation of diastereomeric diglucoside derivatives (S,S)-8 and (R,R)-9. Synthetic (S,S)-SDG-1 and (R,R)-SDG-2 exhibited potent antioxidant properties (EC50 = 292.17 ± 27.71 μM and 331.94 ± 21.21 μM, respectively), which compared well with that of natural (S,S)-SDG-1 (EC50 = 275.24 ± 13.15 μM). These values are significantly lower than those of ascorbic acid (EC50 = 1129.32 ± 88.79 μM) and α-tocopherol (EC50 = 944.62 ± 148.00 μM). Compounds (S,S)-SDG-1 and (R,R)-SDG-2 also demonstrated powerful scavenging activities against hydroxyl [natural (S,S)-SDG-1: 3.68 ± 0.27; synthetic (S,S)-SDG-1: 2.09 ± 0.16; synthetic (R,R)-SDG-2: 1.96 ± 0.27], peroxyl [natural (S,S)-SDG-1: 2.55 ± 0.11; synthetic (S,S)-SDG-1: 2.20 ± 0.10; synthetic (R,R)-SDG-2: 3.03 ± 0.04] and DPPH [natural (S,S)-SDG-1: EC50 = 83.94 ± 2.80 μM; synthetic (S,S)-SDG-1: EC50 = 157.54 ± 21.30 μM; synthetic (R,R)-SDG-2: EC50 = 123.63 ± 8.67 μM] radicals. These results confirm previous studies with naturally occurring (S,S)-SDG-1 and establish both (S,S)-SDG-1 and (R,R)-SDG-2 as potent antioxidants and free radical scavengers for potential in vivo use. 相似文献
2.
Two new protostemonine-type alkaloids, javastemonine A and B (3 and 4) have been isolated from the root extracts of Stemona javanica together with four known Stemona alkaloids, 13-demethoxy-11(S*),12(R*)-dihydroprotostemonine (1), isoprotostemonine (2), protostemonine and isomaistemonine. The structures and relative configurations of the new alkaloids were determined by spectroscopic analysis. The alkaloids 1 and 2 and protostemonine showed moderated antiplasmodial activities against the Plasmodium falciparum strains, TM4 (IC50 values of 17.7 ± 3.7, 16.8 ± 5.4, 16.0 ± 4.2 μg/mL, respectively) and K1 (IC50 values of 16.8 ± 3.1, 14.1 ± 3.7, 11.9 ± 3.3 μg/mL, respectively). These compounds showed no significant cytotoxicities against KB or Vero cells or acetylcholinesterase inhibitory activities. 相似文献
3.
《Phytochemistry letters》2008,1(1):44-48
A flavonoid glycoside, kaempferol 3-O-β-d-glucopyranosyl (1 → 2)-O-β-d-glucopyranosyl (1 → 2)-O-[α-l-rhamnopyranosyl-(1 → 6)]-β-d-glucopyranoside (1), along with two known C- and O-flavonoid glycosides (2 and 3, respectively), were isolated from carnation (Dianthus caryophyllus). The structures of the isolated compounds have been elucidated unambiguously by UV, MS, and a series of 1D and 2D NMR analyses. The isolated compounds and other flavonoid glycoside analogues exhibited antifungal activity against different Fusarium oxysporum f.sp. dianthi pathotypes. 相似文献
4.
《Inorganica chimica acta》2006,359(4):1275-1281
Two new complexes of composition [Cu(2-NO2bz)2(3-pyme)2(H2O)2] (1) and/or [Cu{3,5-(NO2)2bz}2(3-pyme)2] (2) (3-pyme = 3-pyridylmethanol, ronicol or 3-pyridylcarbinol, 2-NO2bz = 2-nitrobenzoate and 3,5-(NO2)2bz = 3,5-dinitrobenzoate) have been prepared and studied by elemental analysis, electronic, infrared and EPR spectroscopy, magnetic susceptibility measurements and the structure of both complexes has been solved. Complex (1) shows an unusual molecular type of structure consisting of the [Cu(2-NO2bz)2(3-pyme)2(H2O)2] molecules held together by hydrogen bonds and van der Waals interactions. Complex (2) exhibits a polymeric chain-like structure [Cu{3,5-(NO2)2bz}2(3-pyme)2]n with copper atoms doubly bridged by two 3-pyridylmethanol molecules and the polymeric molecules are held together by van der Waals interactions. Complex (1) exhibits a magnetic moment μeff = 1.84 B.M. at 300 K that remains nearly constant within the temperature region (5–300 K). Further cooling results in lowering the magnetic moment to μeff = 1.82 B.M. at 1.8 K. The magnetic susceptibility temperature dependence obeys Curie–Weiss law with Curie constant of 0.423 cm3 K mol−1 and with Weiss constant of −0.06 K. The magnetic moment of (2) exhibits a small increase with a decrease in the temperature (μeff = 1.80 B.M. at 300 K and μeff = 1.85 B.M. at 1.8 K) with Curie constant of 0.409 cm3 K mol−1 and with Weiss constant of +1.1 K, which can indicate a very weak ferromagnetic interaction between the copper atoms within the chain. Applying the molecular field model resulted in obtaining zJ′ values −0.08 cm−1 for complex (1), and −0.07 cm−1 for complex (2), respectively, that could characterize intermolecular and interchain interactions transmitted through π–π stacking. 相似文献
5.
To date, there have been reports mostly about research results of the peony root in comparison to the aerial parts. According to our study, the aerial parts of P.lactiflora showed superior anti-oxidative and pancreatic lipase inhibitory activities than its root. Especially, the water extract and the ethyl acetate fraction of the ethanol extract exhibited potent pancreatic lipase inhibitory activity by 53.11 ± 1.22% and 46.16 ± 1.55% at the same dose of orlistat (62.5 ± 1.27%). The ethanol extract exhibited the best anti-oxidative activity with IC50 of 17.08 ± 0.9 μg/mL, and the ethyl acetate fraction 19.75 ± 0.02 μg/mL, respectively, comparing to the positive control rutin (IC50, 22.66 ± 0.29 μg/mL). From the anti-oxidative and pancreatic lipase inhibitory active fractions three new compounds, monplacphloroside (1), monplachydroxyquinoside (2) and herbacetin-7-O-β-d-sophoroside (3) were isolated along with 19 (4-22) known ones.Compounds, PGG (14), 1-O-methyl-2,3,4,6-tetra-O-galloyl-β-d-glucopyranose (17) and ethylgallate (9) were found to be the strongest antioxidants and pancreatic lipase inhibitors. Monoterpenes, albiflorin R2 (19) and albiflorin (20) were determined for the first time as strong pancreatic lipase inhibitors. The presence of the esterified galloyl moiety, with its increasing numbers or the β-lactone cycle within the molecular structure plays an essential role for the enhancement of the pancreatic lipase enzyme inhibitory activity. 相似文献
6.
《Inorganica chimica acta》2006,359(11):3549-3556
A series of cationic trispyrazolylmethane complexes of the general form [TmRM(CH3CN)3]2+ (Tm = tris(pyrazolyl)methane, 1, R = 3,5-Me2, M = Fe(II); 2, R = 3-Ph, M = Fe(II); 3, R = 3,5-Me2, M = Co(II); 4, R = 3-Ph, M = Co(II)) with ‘piano-stool’ structures was prepared by the reaction of the N3tripodal ligands (TmR)with [(CH3CN)6M](BF4)2 in a 1:1 stoichiometric ratio. Magnetic susceptibility measurements indicate that all four complexes with BF4− counter anions are paramagnetic, high-spin systems in the solid state with μeff at high temperatures of 5.2 (1, S = 2), 5.4 (2, S = 2), 4.9 (3, S = 3/2) and 4.6 (4, S = 3/2) BM, respectively. Comparisons of bond lengths from the metal centre to the TmR nitrogen donors, and from the metal centre to the acetonitrile nitrogen donors indicate that the neutral tripodal ligands appear to be more weakly coordinated to the metal centre than are the acetonitrile ligands. Reactions of these tripodal complexes with bidentate phosphine ligands, such as 1,2-diphosphinoethane or 1,2-bis(diallylphosphino)ethane leads to displacement of the tripodal ligand, or to the formation of more thermally stable bis-ligand complexes M(TmR)2 (R = 3,5-dimethyl). 相似文献
7.
《Bioorganic & medicinal chemistry letters》2014,24(17):4166-4170
In search of potential therapeutics for tuberculosis, we describe here the synthesis and in vitro antitubercular activity of a novel series of thiazolone piperazine tetrazole derivatives. Among all the synthesized derivatives, four compounds (10, 14, 20 and 33) exhibited more potent activity (MIC = 3.08, 3.01, 2.62 and 2.51 μM) than ethambutol (MIC = 9.78 μM) and pyrazinamide (MIC = 101.53 μM) against Mycobacterium tuberculosis. Furthermore, they displayed no toxicity against Vero cells (C1008) and mouse bone marrow derived macrophages (MBMDMϕ). These investigated analogues have emerged as possible lead molecule to enlarge the scope of the study. 相似文献
8.
Narsimha Reddy Penthala Purushothama Rao Ponugoti Vinod Kasam Peter A. Crooks 《Bioorganic & medicinal chemistry letters》2013,23(5):1442-1446
A series of novel 5-((1-aroyl-1H-indol-3-yl)methylene)-2-thioxodihydropyrimidine-4,6(1H,5H)-diones (3a–z) have been evaluated for in vitro cytotoxicity against a panel of 60 human tumor cell lines. Compound 3k exhibited the most potent growth inhibition against melanoma MDA-MB-435 cells (GI50 = 850 nM), against leukemia SR cancer cells (GI50 = 1.45 μM), and OVCAR-3 (GI50 = 1.26 μM) ovarian cancer cell lines. The structurally related compound 3s had a GI50 value of 1.77 μM against MDA-MB-435 cells. The N-naphthoyl analogue 3t had GI50 values of 1.30 and 1.91 μM against HOP-92 non-small cell lung cancer and MDA-MB-435 melanoma cell lines, respectively. The related analogue 3w had GI50 values of 1.09 μM against HOP-92 non-small cell lung cancer cell lines. Interestingly, docking of the two active molecules 3k and 3w into the active site of COX-2 indicates that these compounds are COX-2 ligands with strong hydrophobic and hydrogen bonding interactions. Thus, compounds 3k, 3t, 3s, and 3w constitute a new class of anticancer/anti-inflammatory agents that may have unique potential for cancer therapy. 相似文献
9.
The present study was undertaken to gain insight into the associations of mercury(II) with dicysteinyl tripeptides in buffered media at pH 7.4. We investigated the effects of increasing the distance between cysteinyl residues on mercury(II) associations and complex formations. The peptide–mercury(II) formation constants and their associated thermodynamic parameters in 3-(N-morpholino)propanesulfonic acid (MOPS) buffered solutions were evaluated by isothermal titration calorimetry. Complexes formed in different relative ratios of mercury(II) to cysteinyl peptides in ammonium formate buffered solutions were characterized by LTQ Orbitrap mass spectrometry. The results from these studies show that n-alkyl dicysteinyl peptides (CP 1–4), and an aryl dicysteinyl peptide (CP 5) can serve as effective “double anchors” to accommodate the coordination sites of mercury(II) to form predominantly one-to-one Hg(peptide) complexes. The aryl dicysteinyl peptide (CP 5) also forms the two-to-two Hg2(peptide)2 complex. In the presence of excess peptide, Hg(peptide)2 complexes are also detected. Notably, increasing the distance between the ligating groups or “anchor points” in CP 1–5 does not significantly affect their affinity for mercury(II). However, the enthalpy change (ΔH) values (ΔH1 ∼ −91 kJ mol−1 and ΔH2 ∼ −66 kJ mol−1) for complex formation between CP 4 and 5 with mercury(II) are about one and a half times larger than the related values for CP 1, 2 and 3 (ΔH1 ∼ −66 kJ mol−1 and ΔH2 ∼ 46 kJ mol−1). The corresponding entropy change (ΔS) values (ΔS1 ∼ −129 J K−1 mol−1 and ΔS2 ∼ −116 J K−1 mol−1) of the structurally larger dicysteinyl peptides CP 4 and 5 are less entropically favorable than for CP 1, 2 and 3 (ΔS1 ∼ −48 J K−1 mol−1 and ΔS2 ∼ −44 J K−1 mol−1). Generally, these associations result in a decrease in entropy, indicating that these peptide–mercury complexes potentially form highly ordered structures. The results from this study show that dicysteinyl tripeptides are effective in binding mercury(II) and they are promising motifs for the design of multi-cysteinyl peptides for binding more than one mercury(II) ion per peptide. 相似文献
10.
《Inorganica chimica acta》2006,359(11):3639-3648
A series of alkynylgold(I) bis(diphenylphosphino)alkyl- and aryl-amine complexes, [{Ph2PN(R)PPh2}Au2(CCR′)2] [R = nPr, R′ = Ph (1), C6H4OMe-p (2), C6H4Me-p (3), C6H4Cl-p (4); R = C6H4OMe-p, R′ = Ph (5)], has been synthesized. The X-ray crystal structures of 1 and 2 revealed the presence of short intramolecular Au⋯Au contacts with the distances of 2.8404(8) and 3.0708(7) Å. The luminescence behavior of the complexes were studied. 相似文献
11.
Ronald C. Bernotas Schuyler Antane Rajesh Shenoy Van-Duc Le Ping Chen Boyd L. Harrison Albert J. Robichaud Guo Ming Zhang Deborah Smith Lee E. Schechter 《Bioorganic & medicinal chemistry letters》2010,20(5):1657-1660
Novel 3-(arylsulfonyl)-1-(azacyclyl)-1H-indoles 6 were synthesized as potential 5-HT6 receptor ligands, based on constraining a basic side chain as either a piperidine or a pyrrolidine. Many of these compounds had good 5-HT6 binding affinity with Ki values <10 nM. Depending on substitution, both agonists (e.g., 6o: EC50 = 60 nM, Emax = 70%) and antagonists (6y: IC50 = 17 nM, Imax = 86%) were identified in a 5-HT6 adenylyl cyclase assay. 相似文献
12.
2-Pyrazolins 14a–l and pyrazoles 15a–l were designed as celecoxib analogs for the evaluation of their in vitro COX-1/COX-2 inhibitory activity and the in vivo anti-inflammatory activity. Compounds 14i, 15a, 15d and 15f were the most COX-2 selective derivatives (S.I. = 5.93, 6.08, 5.03 and 5.27 respectively) while the pyrazoline derivatives 14g and 14i exhibited the highest AI activity (ED50 = 190.5 and 160.1 μmol/kg po, respectively). 相似文献
13.
《Bioorganic & medicinal chemistry letters》2014,24(16):3974-3978
Neurotensin (NT) is an endogenous tridecapeptide found in the central nervous system (CNS) and in peripheral tissues. Neurotensin exerts a wide range of physiological effects and it has been found to play a critical role in a number of human diseases, such as schizophrenia, Parkinson’s disease and drug addiction. The discovery of small-molecule non-peptide neurotensin receptor (NTSR) modulators would represent an important breakthrough as such compounds could be used as pharmacological tools, to further decipher the cellular functions of neurotensin, and potentially as therapeutic agents to treat human disease. Herein, we report the identification of non-peptide low-micromolar neurotensin receptor 1 (NTSR1) full agonists, discovered through structural optimization of the known NTSR1 partial agonist 1. In vitro cellular screenings, based on an intracellular Ca2+ mobilization assay, revealed our best hit molecule 8 (SR-12062) to have an EC50 of 2 μM at NTSR1 with full agonist behaviour (Emax = 100%), showing a higher efficacy and ∼90-fold potency improvement compared to parent compound 1 (EC50 = 178 μM; Emax = 17%). 相似文献
14.
Iis Siti Jahro Djulia Onggo Susanto Imam Rahayu M. Carmen Muñoz Ana B. Gaspar Maksym Seredyuk Philipp Gütlich José Antonio Real 《Inorganica chimica acta》2008,361(14-15):4047-4054
Three new compounds formulated (ClO4)2[Fe(pq)3] (1), (BF4)2[Fe(pq)3] · EtOH (2) and {(ClO4)[MnCr(C2O4)3][Fe(pq)2(H2O)2]} (3), where pq is 2,2′-pyridylquinoline, have been synthesised and characterised. Despite the different crystal packing exhibited by 1 and 2, the cationic species [Fe(pq)3]2+ are structurally quite similar. At 293 K, the Fe–N bond lengths are characteristic of the iron(II) in the high-spin state. In contrast to 1, 2 undergoes a continuous spin transition. Indeed, at 95 K its structure experiences a noticeable change in the Fe–N bonds and angles, i.e. the Fe–N bonds shorten by 0.194 Å on the average. The magnetic behaviour confirms that 1 is fully high-spin in the 4–300 K temperature range while 2 shows a spin transition centred at T1/2 = 150 K. The corresponding enthalpy, entropy and interaction parameter are ΔH = 7.49 kJ mol?1, ΔS = 50 J K?1 mol?1and Γ = 1.35 kJ mol?1. Compound 3 has been obtained as a microcrystalline powder. The magnetic properties of 3 point at the occurrence of ferromagnetic coupling below 100 K and the onset of a ferromagnetic ordering below 10 K (Weiss constant equal to 6.8 K). The Mössbauer spectra of 3 show the occurrence of a magnetic order at T ? 4.2 K. 相似文献
15.
《Inorganica chimica acta》2006,359(7):2015-2022
The reaction of [Cu(tren)(OH2)](ClO4)2 with KCN gave a mononuclear complex [Cu(tren)(CN)](ClO4) (1) (tren = tris(2-aminoethyl)amine). Using 1 as a building block, one pentanuclear compound, [{Cu(tren)(NC)}4Ni](ClO4)6 (2) and two trinuclear complexes, [{Cu(tren)NC}2Co(tren)](ClO4)5 · 2H2O (3), [{Cu(tren)CN}2NiL](ClO4)4 (4) (L = 3,10-bis(2-hydroxyethyl)-1,3,5,8,10,12-hexaazacyclotetradecane) were prepared and characterized by single crystal X-ray analysis. In 1, Cu(II) atom adopts a distorted trigonal bipyramidal (TBP) geometry. In 2, the Ni(II) atom occupies the center of the pentanuclear compound with a square-planar coordination geometry. In 3, the six-coordinated Co(III) atom presents a distorted octahedral geometry with four nitrogen atoms from tren and two carbon atoms of bridged cyano groups in cis-positions. In 4, the nickel atom is located in an inversion center and coordinated with two [(tren)CuCN]+ moieties through cyano-bridging ligands. Magnetic susceptibility measurements of 2–4 show that the magnetic interactions between the heterometallic ions are antiferromagnetical coupling through the cyano bridges with g = 2.25, J = −0.142 cm−1 and J′ = −0.167 cm−1 for 2, g = 2.06, J = −0.094 cm−1 for 3, and g = 2.20, J = −33.133 cm−1 for 4. The correlations between the structures and the J values are discussed. 相似文献
16.
Y. Thirupathi Reddy P. Narsimha Reddy Srinivas Koduru Chendil Damodaran Peter A. Crooks 《Bioorganic & medicinal chemistry》2010,18(10):3570-3574
A series of substituted (Z)-5-(N-benzylindol-3-ylmethylene)imidazolidine-2,4-dione (3) analogs structurally related to aplysinopsin, and that incorporate a variety of substituents in both the indole and N-benzyl moieties have been synthesized under microwave irradiation and conventional heating methods These analogs were evaluated for their anti-proliferative activity against MCF-7 and MDA-231 breast cancer cell lines, and A549 and H460 lung cancer cell lines. Two analogs, 3f and 3j had IC50 values of 4.4 and 5.2 μM, respectively, compared to 5-fluorouracil (IC50 = 15.2 μM) against MCF-7 cells. 相似文献
17.
《Bioorganic & medicinal chemistry》2016,24(7):1513-1519
Negative allosteric modulators (NAMs) of GluN2B-containing NMDARs provide pharmacological tools for the treatment of chronic neurodegenerative diseases. Novel NAMs have been designed on the basis of computational studies focused on the ‘hit compound’ 3. This series of indoles has been tested in competition assay. Compounds 16 and 17 were the most active ligands (IC50 values of 83 nM and 71 nM, respectively) and they showed a potency close to that of reference compounds ifenprodil (1, IC50 = 47 nM) and 3 (IC50 = 25 nM). Furthermore, docking studies have been performed for active ligand 16 and the results were in a good agreement with biological data. 相似文献
18.
Chemical investigation of leaves and heartwood of Dalbergia boehmii resulted in the isolation of two new phenolic compounds, designated dalbergestan (1) and dalbergichromone (2), along with eleven known compounds, carpachromene (3), proanthocyanidin A-2 (4); piceatannol (5); biochanin A (6); macckiain (7); homopterocarpin (8); angolensin (9); medicarpin (10); 2′,7-dihydroxy-4′,5′-dimethoxyisoflavone (11); 2′-methoxyformononetin (12); and genistein (13). The structures of the new compounds were elucidated on the basis of extensive spectroscopic analyses including, IR, UV, 1D and 2D – NMR as well as HRMS data. Some of the isolated compounds were evaluated for their in vitro insulin secretion activity on isolated mice islets, leishmanicidal activity against L. major (DESTO) promastigotes and in vitro cytotoxicity on MCF-7 cell lines. All tested compounds were inactive on glucose-stimulated insulin secretion at stimulatory glucose (20.0 mM) from MIN6 cells. Compounds 3 (IC50, 70.0 μg/ml), 6 (IC50, 60.3 μg/ml), 7 (IC50, 86.5 μg/ml) and 13 (IC50, 62.6 μg/ml) exhibited low leishmanicidal activity while compound 12 (IC50, 56.8 μg/ml) displayed a moderate activity. Compounds 3 and 5 were found to be active against MCF-7 at 50 μM with IC50 value 33.2 ± 3.79 μg/ml and 42.64 ± 5.05 μg/ml respectively. 相似文献
19.
《Inorganica chimica acta》2006,359(9):2924-2932
We report here the syntheses of two new metal complexes (M = Co, 2; M = Ru, 3) of the chiral porphyrin TmyrtP (1) (TmyrtP = dianion of the meso-tetrakis[(1R)-apopinen-2-yl]porphyrin). Both complexes exist as a mixture of atropisomers. Complexes 2 and 3 activate aromatic azides for the amination under mild conditions of unsaturated hydrocarbons. Even though the observed ee values are low, this is the first asymmetric transfer of the nitrene residue of aryl azides to a prochiral olefin catalyzed by a transition metal complex to be reported in the literature. Complex 3 also showed a good catalytic activity in cyclopropanation reactions with ethyldiazoacetate even at low temperatures (−30 °C) but a poor diastereo- and enantioselectivity were observed. 相似文献
20.
《Inorganica chimica acta》2006,359(5):1659-1665
The solvento calcium bromide CaBr2(DME) has been prepared by reacting anhydrous calcium acetate with acetyl bromide in dimethoxyethane (DME), while refluxing a suspension of CaCl2 in DME/SOCl2 gave CaCl2(DME), high yields being secured in both cases. Crystals of the ionic [CaBr(DME)2(H2O)2]Br (1), were shown to contain heptacoordinated calcium(II) with bidentate DME. Two polymorphs of the mononuclear, CaBr2(DME)2(MeCOOH) (2), differing for their packing efficiency, have been studied by X-ray diffractometry. Compound 2 loses one DME and the coordinated acetic acid under vacuum at 30 °C, yielding CaBr2(DME). Coordinated DME in CaX2(DME) was found to be substituted by nitrogen bases in toluene, the adducts CaX2py2 (X = Cl, Br), CaBr2(DMEDA)2, (DMEDA = N,N′-dimethylethylenediammine) and CaBr2(L–L–L) [L–L–L = 2,6-bis(3,5-dimethyl-N-pyrazolyl)pyridine)] being obtained in good yields. 相似文献