- Anti-inflammatory glycosides from the roots of Paeonia intermedia C. A. Meyer
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Three new phenolic glycosides, intermedia A–C (1–3), one new acyclic alcohol glycoside, intermedia D (4), together with 3 known glycosides (5–7), were isolated from the dried roots of Paeonia intermedia C. A. Meyer. Their structures were established by means of extensive spectroscopic analysis (HRESIMS, NMR). Compound 1 have a rare benzo[1,5]dioxepine skeleton. The bioassay results showed that compound 3 exhibited inhibitory activity against proinflammatory cytokines nitric oxide (NO) secretion in LPS-activated RAW264.7 cells with an IC50 value of 85.76 ± 1.36 μM.
- Yu, Liang,Zhu, Ling-Juan,Wang, An-Hua,Qin, Yu,Zhang, Xue,Jia, Jing-Ming,Yao, Xin-Sheng
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Read Online
- Convergent Protein Phosphatase Inhibitor Design for PTP1B and TCPTP: Exchangeable Vanadium Coordination Complexes on Graphene Quantum Dots
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Development of potent and specific inhibitors of protein tyrosine phosphatase 1B (PTP1B) with desired drug-like properties is still a challenge. Based on the crystal structures of PTP1B transition state analog consisting of a vanadate peptide, a novel approach is proposed to design PTP1B inhibitors, in which the tyrosyl vanadate ester of a PTP1B peptide mimic (PL1) is stably integrated on the membrane permeable graphene quantum dots (GQDs). The vanadate complexes (GQD-PL1-VV) prepared exhibit high potency (Ki?= 6?± 1?× 10?9 m) and selectivity (selectivity index SI >200?for PTP1B versus the T-cell protein tyrosine phosphatase, TCPTP) in solution and in HepG2 cells. Oral administration of GQD-PL1-VV in db/db model mice shows selective PTP1B inhibition in liver and fat tissues and exhibits improved anti-diabetic activity compared to bis(maltolato)oxovanadium(IV). Moreover, exchange of PL1 to a TCPTP-specific ligand (PL2) results in potent TCPTP inhibition (Ki?= 59?± 12?× 10?9 m) as expected with SI ≈23 versus PTP1B. Overall, the present results provide a paradigm shift and a general design of phosphatase inhibitors consisting of GQDs, a complexing targeting ligand and vanadium (V) for selective regulation of PTP1B both in vitro and vivo.
- Crans, Debbie C.,Dong, Yaqiong,Feng, Bo,Shang, Bing,Yang, Xiaoda,Zhang, Bowen
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- Synthesis, photochemical isomerization and photophysical properties of hydrazide-hydrazone derivatives
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Hydrazide-hydrazone derivatives have been utilized in molecular switches, sensing, metallo assemblies, drugs and other applications. The hydrazide-hydrazone functional group contains the -CO-NH-NCH- moiety that yields the hydrazide-hydrazone group its physical, chemical and biochemical properties; however, the application in security protection has not been explored before. Herein, the 2-(ortho-), 3-(meta-), 4-(para-) substituted pyridine conjugated to 2,6-dihydroxybenzoic acid, which containing hydrazide-hydrazone as photoswitch linker were designed and synthesized (3a-3c). Interestingly, when irradiating the ortho-substituted pyridine of molecule 3a with a light of 365 nm, obvious emission intensity enhancements were detected. However, 3a-3c before irradiation and 3b-3c after irradiation show no fluorescence. UV-vis, fluorescence, 1H NMR and Fourier transform infrared spectra and density functional theory calculations were carried out, which revealed that the hydrazide-hydrazone derivative of 3a could undergo a characteristic E to Z photoisomerization after light irradiation for 365 nm. The Z isomer of 3a may have additional intramolecular hydrogen bonds to restrict the motions of the molecule, thus increasing the fluorescence intensity of 3a. The experimental and molecular calculation results agreed and thus demonstrated the first example of invisible ink based on the hydrazide-hydrazone motif.
- Wu, Bao-Xing,Chang, Hsin-Yueh,Liao, Yi-Shun,Yeh, Mei-Yu
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p. 1651 - 1657
(2021/02/06)
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- Yicathins B and C and Analogues: Total Synthesis, Lipophilicity and Biological Activities
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Natural products have always been an important source of new hits and leads in drug discovery, with the marine environment being regarded as a significant source of novel and exquisite bioactive compounds. Yicathins B and C are two marine-derived xanthones that have shown antibacterial and antifungal activity. Herein, the total synthesis of these yicathins and six novel analogues is reported for the first time. As marine natural products tend to have very lipophilic scaffolds, the lipophilicity of yicathins and their analogues was evaluated in the classical octanol/water system and a biomimetic model-based system. As the xanthonic nucleus is a “privileged structure”, other biological activities were evaluated, namely antitumor and anti-inflammatory activities. An interesting anti-inflammatory activity was identified for yicathin analogues that paves the way for the design of dual activity (anti-infective and anti-inflammatory) marine-inspired xanthone derivatives.
- Afonso, Carlos M. M.,Azevedo, Carlos M. G.,Bousbaa, Hassan,Ferreira, Helena,Henriques, Ana,Loureiro, Daniela R. P.,Magalh?es, álvaro F.,Neves, Nuno,Pinto, Joana,Pinto, Madalena M. M.,Reis, Salette,Soares, José X.,Vieira, Sara
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supporting information
(2020/04/17)
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- Pyrimidine salicylic acid derivative as well as preparation method and application thereof
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The invention provides a pyrimidine salicylic acid derivative as well as a preparation method and application thereof. The chemical structural formula of the pyrimidine salicylic acid derivative is represented by a formula (I) (shown in the description). The preparation method comprises the step of reacting by virtue of acid of bispyribac-sodium and trifluoroethanol or 4-butenol in an organic solvent in the presence of triethylamine and 1-hydroxybenzotriazole, so as to obtain the compound of the formula (I). The preparation method is simple in operation and relatively high in yield, the prepared pyrimidine salicylic acid derivative is low in dose and high in activity, has herbicidal activities to agricultural weeds such as dicotyledon weeds and monocotyledon weeds at 15g/hm, particularly has relatively prevention effects to the after-treatment of seedlings of goosefoots and crab grass and can be taken as a candidate compound of herbicides, a new choice is provided for the new species of the herbicides, and the pyrimidine salicylic acid derivative has potential industrial application prospects.
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Paragraph 0020; 0029
(2018/10/19)
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- Bispyribac derivative, and preparation method and application of bispyribac derivative
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The invention discloses a bispyribac derivative, and a preparation method and an application of the bispyribac derivative. The bispyribac derivative has the following structure as shown in the specification. The preparation method particularly comprises the following steps of: taking 2,6-dihydroxy-benzoic acid as a raw material for multi-step reactions to synthesize bispyribac (acid), then preparing bispyribac acyl chloride, further performing esterification reaction with 2-pyridyl ethanol to synthesize the bispyribac derivative, namely 2-(pyridine-2-yl) ethyl-2,6-bi((4,6-dimethoxy pyridine-2-yl) oxy) benzoate. The compound has better weeding activity and especially has better removal activity on a dicotyledonous weed, namely sisymbrium sophia, and the preparation method is simple to operate and higher in yield.
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Paragraph 0013; 0023; 0024
(2017/11/30)
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- Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV
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Using hydroxy-/dihydroxybenzoic acids as leads, a series of methyl, ethyl and iso-propyl esters of 4-hydroxy-benzoic acid, 2,4-, 2,5-, 2,6-, 3,4-, and 3,5-dihydroxybenzoic acids and of coumaric acid, were obtained and investigated for the inhibition of six mammalian carbonic anhydrase (CA, EC 4.2.1.1) isoforms, that is, the cytosolic CA I, II and VII, and the transmembrane CA IX, XII and XIV, many of which are established drug targets. Other compounds incorporating phenol/catechol moieties were obtained from dopamine by reaction with fluorescein isothiocyanate or with 2,4,6-trisubstituted pyrylium salts. Some aminophenols were also derivatized in a similar manner, by using pyrylium salts. Many of these compounds showed increased inhibitory action compared to the lead compounds from which they were obtained, with efficacy in the submicromolar range against most investigated CA isoforms. As phenols are a class of less investigated CA inhibitors (CAIs) compared to the sulfonamides, and their mechanism of inhibition is less well understood, compounds of the type designed here may be helpful in gaining more insights into these phenomena.
- Carta, Fabrizio,Vullo, Daniela,Maresca, Alfonso,Scozzafava, Andrea,Supuran, Claudiu T.
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supporting information
p. 1564 - 1569
(2013/04/10)
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- Efficient macrocyclization achieved via conformational control using intermolecular noncovalent π-cation/arene interactions
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Quinolinium salt 3 is an effective additive that acts as a conformation control element (CCE) to promote macrocyclization to form rigid cyclophanes via olefin metathesis or Glaser-Hay coupling, which do not cyclize in the absence of the additive. The additives are easily synthesized and highly modifiable and have solubility profiles which allow for simple recovery via filtration.
- Bolduc, Philippe,Jacques, Alexandre,Collins, Shawn K.
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supporting information; experimental part
p. 12790 - 12791
(2010/11/04)
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- Bone selective effect of an estradiol conjugate with a novel tetracycline-derived bone-targeting agent
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In this study a novel bone-targeting agent containing elements of the tricarbonylmethane system of ring A of tetracycline was developed and was shown to bind to the mineral constituent of bone, hydroxyapatite. Conjugation of this bone-targeting agent to estradiol resulted in a bone-targeted estrogen (BTE2-A1) with an enhanced ability to bind to hydroxyapatite. In an ovariectomized rat model of osteoporosis a partial separation of the skeletal effects of estradiol from the uterine effects was observed following subcutaneous administration of BTE2-A1. This novel bone-targeting estradiol delivery system has the potential to improve the safety profile of estradiol in the treatment of osteoporosis.
- Neale, Jason R.,Richter, Natali B.,Merten, Kevyn E.,Grant Taylor,Singh, Sujan,Waite, Leonard C.,Emery, Nicole K.,Smith, Ned B.,Cai, Jian,Pierce Jr., William M.
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supporting information; experimental part
p. 680 - 683
(2009/09/06)
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- Compounds for diagnosis, treatment and prevention of bone injury and metabolic disorders
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The present invention relates to compounds of the formula or pharmaceutically acceptable salts thereof useful for the prophylaxis and treatment of degenerative bone disorders and for the acceleration of bone healing.
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Page/Page column 13
(2010/02/12)
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- Hydroxy-methoxybenzoic methyl esters: Synthesis and antifeedant activity on the pine weevil, Hylobius abietis
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The pine weevil Hylobius abietis (L.) (Coleoptera: Curculionidae) feeds on the bark of coniferous seedlings and is the economically most important forestry restocking pest in large parts of Europe. Substances with an antifeedant effect may offer an environmentally friendly alternative to insecticides for the protection of planted seedlings. Bioassays were performed on commercial and synthetic methyl hydroxy-methoxybenzoates in order to determine their possible antifeedant activity. Two methyl hydroxy-methoxybenzoates were synthesized by esterification and mono-O-methylation of two dihydroxybenzoic acids. A regioselective protection-deprotection strategy was used in the synthetic pathway of the other non-commercial esters, esterification and selective pivaloylation of the less-hindered hydroxyl group of other commercial dihydroxybenzoic acids gave diester intermediates, which then were O-methylated before methanolysis of the pivaloyl group which yielded the desired non-commercial methyl hydroxy-methoxybenzoates. The five synthesized methyl hydroxy-methoxybenzoic esters were complemented with commercial samples of the five other isomers of methyl hydroxy-methoxybenzoate and spectrometric data were collected for the complete set of isomers. All ten isomers were tested for their antifeedant effect on the pine weevil. The effect varied considerably among the hydroxy-methoxybenzoic esters. Methyl 2-hydroxy-3-methoxybenzoate showed the highest effect and may thus be a candidate for practical use in pine weevil pest management.
- Legrand, Sacha,Nordlander, G?ran,Nordenhem, Henrik,Borg-Karlson, Anna-Karin,Unelius, C. Rikard
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p. 829 - 835
(2007/10/03)
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- Synthesis and absolute configuration of (-)-3-butyl-7-hydroxyphthalide, a cytotoxic metabolite of Penicillium vulpinum.
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Both the enantiomers as well as the racemate of 3-butyl-7-hydroxyphthalide (1) were synthesized, and the absolute configuration of the naturally occurring (-)-1 (a weakly cytotoxic metabolite of Penicillium vulpinum) was identified as S.
- Ohzeki, Tomoya,Mori, Kenji
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p. 2240 - 2244
(2007/10/03)
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- IL-8 receptor antagonists
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This invention relates to novel compounds of Formula (1), pharmaceutical compositions and their use in the treatment of disease states mediated by the chemokine, Interleukins-8 (IL-8).
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- Pyrimidin derivatives
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The invention relates to new pharmaceutically active compounds which are are P2-purinoceptor 7-transmembrane (TM) G-protein coupled receptor antagonists, compositions containing them and processes for their preparation.
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- Enantiopure dendrimers derived from the 1,1'-binaphthyl moiety: A correlation between chiroptical properties and conformation of the 1,1'- binaphthyl template
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The absorption and CD spectra of a series of Frechet (compounds 7-10) and backfolding (compounds 11-12) dendrimers derived from enantiopure (S)- 2,2'-dihydroxy-1,1'-binaphthalene have been recorded (THF) in the range 200- 350 nm. All the compounds examined show a positive couplet between 200 and 240 nm (1B transition of the 2-naphthol chromophore), the intensity of which (Δε(max) of the low-energy branch) ranges between 100 and 40. By means of the DeVoe polarizability model the intensity of the 1B couplet has been calculated vs. the dihedral angle θ. This analysis provides θ angles of 95- 110° for the Frechet dendrimers and 100-110°for the backfolding compounds. These values clearly indicate that the torsional angle θ, defined by the two naphthalene planes, never exceeds the critical value of 110°. This investigation confirms the wide utility of CD spectroscopy to provide geometrical information that cannot be obtained by other types of structural analysis.
- Rosini, Carlo,Superchi, Stefano,Peerlings,Meijer
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- 6-Oxa isosteres of anacardic acids as potent inhibitors of bacterial histidine protein kinase (HPK)-mediated two-component regulatory systems
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A series of 6-oxa isosteres of anacardic acids (6-higher alkyl/alkenyl-2-hydroxybenzoic acids) was synthesised and several members were discovered to be among the most potent inhibitors (IC50 values ≤ 5 μM) of the bacterial two-component regulatory systems, KinA/SpoOF and NRII/NRI, reported to date. The Gram-positive antibacterial activity in selected strains is also presented.
- Kanojia, Ramesh M.,Murray, William,Bernstein, Jeffrey,Fernandez, Jeffrey,Foleno, Barbara D.,Krause, Heather,Lawrence, Laura,Webb, Glenda,Barrett, John F.
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p. 2947 - 2952
(2007/10/03)
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- Chiral dendrimers with backfolding wedges
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Dendritic wedges with a substitution pattern that forces the growth inwards are introduced and the use of this new building strategy is exemplified in the synthesis and chiroptical properties of a chiral dendrimer.
- Peerlings,Trimbach,Meijer
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p. 497 - 498
(2007/10/03)
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- Asymmetric Hetero Diels-Alder Reaction Catalyzed by Stable and Easily Prepared CAB Catalyst
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A stable chiral (acyloxy)borane (CAB) complex is prepared in situ by mixing a tartaric acid derivative and arylboronic acids at room temperature.A solution of the catalyst is effective in catalyzing hetero Diels-Alder reactions to produce dihydropyrone derivatives of high optical purities.
- Gao, Quingzhi,Ishihara, Kazuaki,Maruyama, Tohru,Mouri, Makoto,Yamamoto, Hisashi
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p. 979 - 988
(2007/10/02)
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- 2-(Alkylamino)nicotinic Acid and Analogs. Potent Angiotensin II Antagonists
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A series of pyridines and other six-membered ring heterocycles connected to a biphenyltetrazole with a-CH2-NR'-link (1) were discovered to be potent angiotensin II antagonists.In the pyrimidine carboxylic acid series (W = CR, X = N, Y = CH, Z = COOH), compounds with an alkyl group (R') on the exocyclic nitrogen were much more potent than compounds with an alkyl group (R) on the heterocyclic ring.The corresponding pyridine, pyridazine, pyrazine, and 1,2,4-triazine carboxylic acids also showed potent in vitro angiotensin II antagonism.The pyridine (W, X, Y = CH, Z = COOH, R' = n-C3H7) demonstrated potent in vitro activity (pA2 = 10.10, rabbit aorta, and Ki = 0.61 nM, receptor binding in rat liver) as well as exceptional oral antihypertensive activity and bioavailability.Any nonacidic replacement for the carboxylic acid was detrimental for activity.
- Winn, Martin,De, Biswanath,Zydowsky, Thomas M.,Altenbach, Robert J.,Basha, Fatima Z.,et al.
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p. 2676 - 2688
(2007/10/02)
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- Analogues of Platelet Activating Factor. 6. Mono- and Bis-Aryl Phosphate Antagonists of Platelet Activating Factor
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A series of aryl phosphoglyceride (3, 19-61) and bis-aryl phosphate (67-135) antagonists of platelet activating factor (PAF) were prepared.A group of four bifunctional phosphorus reagents (5a-c and 7) were developed that allowed the preparation of these aryl phosphates in which the position of aromatic substitution can be varied.These compounds were examined for their ability to inhibit PAF-induced platelet aggregation of rabbit platelets.Selected compounds were also evaluated for their ability to displace PAF from its receptor on rabbit platelets.These in vitro data were compared to similar data obtained for a number of known PAF antagonists.The compounds were evaluated in vivo, in both the mouse and rabbit, for their ability to prevent death induced by a lethal challenge of PAF.The relationships between the biological activity and the nature, lipophilicity, and position of substituents of the aromatic rings were studied.Compound 105 (CL 184005) has been selected to undergo further development as a potential therapeutic agent for the treatment of septic shock in man.
- Wissner, A.,Carroll, M. L.,Green, K. E.,Kerwar, S. S.,Pickett, W. C.,et al.
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p. 1650 - 1662
(2007/10/02)
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- Synthesis and Fluorescence Properties of Selectively Metallated Diporphyrins with Electron-Accepting Moieties
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Synthesis of selectively metallated diporphyrins with electron-accepting moieties is described.Steady-state fluorescence spectra of these compounds showed substantial quenching of the fluorescence of the free-base porphyrin.A possible "superexchange" mechanism of long-range electron transfer is discussed.
- Nagata, Toshi
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p. 3005 - 3016
(2007/10/02)
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- PEPTIDE BOND FORMATION USING AN ENZYME MIMICKING APPROACH
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A man-made enzyme-model based on a concerted proton transfer step (bifunctional catalysis) which mimics the corresponding step in non-ribosomal peptide synthesis was developed.Important features of the model are the following: (a) a bifunctional acid-base catalyst for the thiolester aminolysis rate acceleration, (b) two thiol-containing arms mimicking the "swinging arms" of the enzyme, and (c) symmetry elements so that the process can be iterated with consequent formation of the polypeptide chain.Peptide bond formation was obtained by intramolecularly catalyzed thiolester aminolysis to give 5 in 80percent isolated yield (Scheme IV, V) and with at least a 103-fold rate acceleration in comparison with the corresponding non catalyzed process (4 -> 6)(Scheme IV, Table 1).The reaction is also 4-20 times faster than the analogous process 4 -> 6 run in the presence of 0.1M external catalyst (Et3N-ButCOOH or 2-Pyridone).Important structural and reaction parameters are discussed.A second intramolecular aminolysis reaction gave tripeptide 8 in lower yield (35percent) because of higher steric congestion in the transition state.
- Gennari, Cesare,Molinari, Francesco,Piarulli, Umberto,Bartoletti, Marcella
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p. 7289 - 7300
(2007/10/02)
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- A Selective Hydrolysis of Aryl Acetates
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Aryl and naphthyl acetates are efficiently hydrolyzed by reaction with toluene saturated with water and p-toluenesulfonic acid adsorbed on silica gel.The procedure allows the selective hydrolysis of aryl acetates in the presence of other ester groups.
- Blay, Gonzalo,Cardona, M. Luz,Garcia, M. Begona,Pedro, Jose R.
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p. 438 - 439
(2007/10/02)
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- Anti-inflammatory and analgesic 3-hydroxybenzo[b]thiophene derivatives, compositions, and method of use therefor
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3-Hydroxybenzo[b]thiophene derivatives, such as 2-aralkyl, 2-alkyl and 2-alkenyl-3-hydroxybenzo[b]-thiophenes, were prepared by, among other methods, ring closure of 2-(2-carboxy-phenylthio)-α-substituted acetic acids. These compounds are found to be useful in the treatment of pain, fever, inflammation, arthritic conditions, asthma, allergic disorders, skin diseases, cardiovascular disorders, psoriasis, inflammatory diseases and other prostaglandin and/or leukotriene mediated diseases.
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- REGULATION OF ENZYMIC OXIDATION OF INDOLE-3-ACETIC ACID BY PHENOLS: STRUCTURE-ACTIVITY RELATIONSHIPS
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Mono- and diphenols were tested for their effects on the decarboxylation of IAA catalysed by purified horseradish peroxidase (EC 1.11.1.7) in the presence or absence of 2,4-dichlorophenol (DCP).The number of hydroxyl groups and their position relative to each other and the nature and position of other substituents on the aromatic ring were found to affect the activity.Although the effects were complex, the following generalizations may be made. (1) Monophenols produce activation when no other cofactor is present. p-Substituted monophenols are more active than o- or m compounds.In the presence of DCP, the activity varies from slight activation to strong inhibition. (2) m-Diphenols also produce activation in the absence of other cofactors while o- and p-diphenols, with the exception of 3,4-dihydroxyacetophenone and 3,4-dihydroxypropiophenone, produce strong inhibition in the presence or absence of DCP.The o-diphenols are degraded in the IAA-oxidizing enzyme system and thus produce only a temporary inhibition. (3) m-Diphenols and 3,4-dihydroxyacetophenone produce a sustained inhibition in the presence of DCP. (4) Substitution at position 2 significantly alters the activity of m-diphenols. (5) o-Methylation alters the activity of most o-diphenols.In the absence DCP, o-methoxyphenols and certain other phenols such as 3,4-dihydroxyacetophenone and 2,6-dihydroxyacetophenone either promote or inhibit IAA oxidation depending on concentration.Key Word Index-Phenols; indole-3-acetic acid; IAA-oxidase; peroxidase.
- Lee, Tsung T.,Starratt, Alvin N.,Jevnikar, John J.
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p. 517 - 524
(2007/10/02)
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- Pyoluteorin Derivatives. II. Synthetic Approaches to Pyrrole Ring Substituted Pyoluteorins (1)
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A method for the regiospecific synthesis of 3-substituted 2-aroylpyrroles is described.These pyrroles, which are structurally related to the naturally occuring antibiotic pyoluteorin, are prepared by a Friedel-Crafts aroylation of 4-substituted pyrrole-3-carboxylic acid esters with 2,6-dimethoxybenzoyl chloride.The carboalkoxy group is then removed by hydrolysis and decarboxylation to produce isomerically pure 3-substituted-2-(2',6'-dimethoxybenzoyl)pyrroles (5 and 13).Conversion of these pyrroles into pyoluteorin-like coumpounds led to some unexpected products which arise from facile cleavage of the dihydroxybenzoyl portion of the molecules during chlorination.
- Cue, Berkeley W.,Chamberlain, Nancy
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p. 667 - 670
(2007/10/02)
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- Synthesis of hydroxy- and amino-substituted benzohydroxamic acids: Inhibition of ribonucleotide reductase and antitumor activity
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Benzohydroxamic acids inhibit mammalian ribonucleotide reductase and exhibit antineoplastic activity in L1210 leukemic mice. Five new hydroxy- and amino-substituted benzohydroxamic acids (3,4- and 3,5-OH,3,4-NH2, 2,3,4-, and 3,4,5-OH) were prepared and tested along with 12 previously reported benzohydroxamic acids (BHA) for enzyme inhibition and antitumor activity. The most potent enzyme inhibitor in this series was 2,3,4-OH-BHA (ID50=3.5 μM), which is 140 times more potent than hydroxyurea, but its toxicity limited the antitumor activity to a 30% increase in life span of L1210 bearing mice at 125 (mg/kg) day ip for 8 days. The most effective antitumor agent in this series was 3,4-OH-BHA which prolonged the life span of L1210 bearing mice 103% at 600 (mg/kg)/day ip for 8 days.
- van't Riet,Wampler,Elford
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p. 589 - 592
(2007/10/05)
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