- A concise synthesis of (±)-methoxyfumimycin ethyl ester
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The protecting-group-free synthesis of (±)-methoxyfumimycin ethyl ester, a potential bacterial peptide deformylase (PDF) inhibitor, is reported. The synthetic approach features a tandem Friedel-Crafts alkylation/lactonisation access as a key reaction to g
- Zhou, Zhiwang,Hu, Yu,Wang, Bin,He, Xiaoru,Ren, Gang,Feng, Lihua
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Read Online
- Synthesis and structural characterization of novel O-substituted phenolic and chalcone derivatives with antioxidant activity
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A series of novel 4-O-alkyltriazolylphenolic derivatives is first synthesized with good to excellent yields via the click reaction of 3-methoxy-4-O-propargylbenzaldehyde or 3-allyl-4-O-propargylacetophenone and aromatic azide derivatives. Next, the chalco
- Ngameni, Bathélémy,Erdo?an, Musa,Kuete, Victor,Dalk?l??, Erdin,Ngadjui, Bonaventure T,Da?tan, Arif
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- Design, synthesis, characterization, and anticancer activity of a novel series of O-substituted chalcone derivatives
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A new series of O-substituted chalcone derivatives bearing an/a allyl-, prenyl- or propargyl-substituent at different positions of rings A and B and their derivatives as drug leads, was designed, synthesized, and characterized. The chalcone derivatives we
- Ngameni, Bathélémy,Cedric, Kamdoum,Mbaveng, Armelle T.,Erdo?an, Musa,Simo, Ingrid,Kuete, Victor,Da?tan, Arif
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- Concise and Convergent Enantioselective Total Syntheses of (+)-and (-)-Fumimycin
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The concise and convergent total syntheses of (+)-and (-)-Fumimycin have been achieved by taking advantage of strategies for the asymmetric aza-Friedel-Crafts reaction of a highly substituted hydroquinone and N-fumaryl ketimine generated from the correspo
- Retini, Michele,Bartolucci, Silvia,Bartoccini, Francesca,Mari, Michele,Piersanti, Giovanni
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- Introducing the Tishchenko reaction into sustainable polymer chemistry
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Taking advantage of the structural characteristics of lignin-derived phenolic compounds, a combination of the Williamson and Tishchenko reactions produced a series of new α,ω-diene functionalized carboxylic ester monomers from both petrochemical and renewable resources, which were applicable in subsequent thiol-ene click and acyclic diene metathesis (ADMET) polymerizations, providing a series of poly(thioether esters) and unsaturated aromatic-aliphatic polyesters with high molecular weights.
- Ren, Tianhua,Chen, Qin,Zhao, Changbo,Zheng, Qiang,Xie, Haibo,North, Michael
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- Synthesis of a Novel calix[4]resorcinarene-Chitosan hybrid
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Synthesis of a novel calix[4]resorcinarene-chitosan hybrid using vanillin as raw material has been conducted. The synthesis was carried out in four steps i.e. (1) allylation of vanillin, (2) HCl-catalyzed condensation allyl vanillin with resorcinol, (3) c
- Santoso, Prio,Anwar, Chairil,Jumina,Siswanta, Dwi,Suharso,Ohto, Keisuke
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- Synthesis of the intermediate for fumimycin: A natural peptide deformylase inhibitor
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Synthetic efforts toward the potential bacterial peptide deformylase inhibitor fumimycin are reported. The synthetic approach features a tandem Friedel-Crafts alkylation/lactonization access as key reaction to the α, α-disubstituted amino acid unit, and r
- Zhou, Zhi-Wang,Li, Wei-Chao,Hu, Yu,Wang, Bin,Ren, Gang,Feng, Li-Hua
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Read Online
- Chemoselective and ligand-free aerobic oxidation of benzylic alcohols to carbonyl compounds using alumina-supported mesoporous nickel nanoparticle as an efficient recyclable heterogeneous catalyst
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An economically efficient and operationally simple ligand-free protocol for the chemoselective oxidation of benzylic alcohols to carbonyl compounds has been developed using alumina-supported nickel nanoparticles as a stable recyclable heterogeneous catalyst along with potassium tert-butoxide in the presence of aerial oxygen as an eco-friendly oxidant. The aliphatic alcohols remained unaffected under the present condition. Excellent chemoselectivity has also been demonstrated through intermolecular and intramolecular competition experiments. This protocol accommodates a diverse range of substituents with the tolerance of various sensitive moieties during the reaction. The catalyst could be recovered by filtration and reused consecutively without any significant loss in the catalytic activity. Moreover, the heterogeneity of the catalyst has also been established by the “hot filtration method (Sheldon's test)”.
- Das, Asit Kumar,Nandy, Sneha,Bhar, Sanjay
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- Iodine-DMSO catalyzed chemoselective oxidative aromatization and deallylation, nondeallylation of aryl allyl ether of tetrahydro-β-carboline
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We have developed a simple method for the chemoselective aromatization of tetrahydro-β-carboline with selective nondeallylation O-allyl groups in the presence of iodine (100 mol %) in dimethyl sulfoxide/H2O2. A convergent approach toward the oxidative aromatization with selective deallylation (deprotection) of O-allyl-tetrahydro-β-carboline using iodine in dimethyl sulfoxide/HCl has been described. The present protocol contains cheap catalyst, easy work up, normal reaction conditions, and high selectivity.
- Gaikwad, Sunil V.,Gaikwad, Milind V.,Lokhande, Pradeep D.
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supporting information
p. 1408 - 1414
(2021/04/26)
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- Novel vanillin derivatives containing a 1,3,4-thiadiazole moiety as potential antibacterial agents
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In this study, thirty-four novel vanillin derivatives containing a 1,3,4-thiadiazole structure were obtained and their antibacterial activities were evaluated. The results indicate that most of the title compounds displayed inhibitory effects on Xanthomonas oryzae pv. oryzae (Xoo) and Xanthomonas oryzae pv. oryzicola (Xoc). Among them, compound 29 exhibited excellent antibacterial activities against Xoo and Xoc in vitro, with the EC50 values of 3.14 and 8.83 μg/mL, respectively, much superior to thiodiazole copper (87.03 and 108.99 μg/mL) and bismerthiazol (67.64 and 79.26 μg/mL). Under greenhouse condition, the protective efficiency of compound 29 against rice bacterial leaf blight was 49.34%, and curative efficiency was 40.96%. In addition, compound 29 can reduce the exopolysaccharides production of Xoo, increase the permeability of cell membrane and damage cell membrane.
- Cai, Hui,Gan, Xiuhai,Li, Shaoyuan,Song, Baoan,Wu, Qiong,Yuan, Ting
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supporting information
(2020/03/24)
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- Preparation, characterization, antioxidant evaluation of new curcumin derivatives and effects of forming HSA-bound nanoparticles on the stability and activity
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Curcumin (CCM) is a well-known active component, which has been studied extensively in food and medicine field since it showed various activities. However, some serious issues limit its application, for example, the extremely low solubility, stability and
- Gao, Feng,Guo, Na,Hao, Tiantian,Wang, Kai,Wang, Pingxi,Yang, Shuyan,Yu, Peng,Zhang, Shutong,Zhao, Yufan
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- Novel curcumin analogue, preparation method and application thereof
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The invention relates to a novel curcumin analogue. The analogue is obtained by modifying curcumin with a substituent common in natural products. Specifically, the general structural formula of the analogue is shown as the specification, wherein R1 and R2
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Paragraph 0101-0103
(2019/10/01)
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- Enantiopure C1-Cyclotriveratrylene with a Reversed Spatial Arrangement of the Substituents
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Cyclotriveratrylene (CTV) is a macrocyclic cyclophane presenting a bowl-shaped conformation, used as building block to construct cryptophane and hemicryptophane capsules. A method to synthesize new enantiopure CTV derivatives with an unprecedented spatial
- Long, Augustin,Colomban, Cedric,Jean, Marion,Albalat, Muriel,Vanthuyne, Nicolas,Giorgi, Michel,Di Bari, Lorenzo,Górecki, Marcin,Dutasta, Jean-Pierre,Martinez, Alexandre
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supporting information
p. 160 - 165
(2019/01/04)
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- Diester monomer containing carboxylic ester structure, polyester thereof and sulfur-containing polyester (by machine translation)
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The invention discloses a diester monomer containing a carboxylic ester structure, a polyester thereof and a sulfur-containing polyester. The monomer is prepared from vanillin, butyraldehyde, p-hydroxybenzaldehyde, 3 - fluorine -4 - hydroxybenzaldehyde, 3 - bromo -4 - hydroxybenzaldehyde and 3 - methyl -4 - hydroxybenzaldehyde, and the reaction product is recrystallized or separated to obtain an enal monomer; 2) is reacted, with an enal monomer as a raw material, without a solvent or dissolved in an organic solvent. After the reaction product is recrystallized or separated from the chromatographic column, a dicarboxylic monomer containing a carboxylic acid ester structure is obtained. The polyester is prepared under the action of Hoveveveda-Grubrubbs catalyst and p-benzoquinone. The sulfur-containing polyester is prepared by reacting with a dithiol compound. The novel monomer and the polymer, provided by the invention, have the advantages of abundant raw material sources, simple preparation process, no generation of inflammable and explosive low boiling volatile matters, environmental protection, universality and the like. (by machine translation)
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Paragraph 0084-0088
(2019/10/01)
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- Facile synthesis of vanillin-based novel bischalcones identifies one that induces apoptosis and displays synergy with Artemisinin in killing chloroquine resistant Plasmodium falciparum
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The inherent affinity of natural compounds for biological receptors has been comprehensively exploited with great success for the development of many drugs, including antimalarials. Here the natural flavoring compound vanillin has been used as an economical precursor for the synthesis of a series of novel bischalcones whose in vitro antiplasmodial activities have been evaluated against erythrocytic stages of Plasmodium falciparum. Bischalcones 9, 11 and 13 showed promising antiplasmodial activity {Chloroquine (CQ) sensitive Pf3D7 IC50 (μM): 2.0, 1.5 and 2.5 respectively}but only 13 displayed potent activities also against CQ resistant PfDd2 and PfIndo strains exhibiting resistance indices of 1.4 and 1.5 respectively. IC90 (8 μM) of 13 showed killing activity against ring, trophozoite and schizont stages. Further, 13 initiated the cascade of reactions that culminates in programmed cell death of parasites including translocation of phosphatidylserine from inner to outer membrane leaflet, loss of mitochondrial membrane potential, activation of caspase like enzyme, DNA fragmentation and chromatin condensation. The combinations of 13 + Artemisinin (ART) exhibited strong synergy (ΣFIC50:0.46 to 0.58) while 13 + CQ exhibited mild synergy (ΣFIC50: 0.7 to 0.98) to mild antagonism (ΣFIC50: 1.08 to 1.23) against PfIndo. In contrast, both combinations showed marked antagonism against Pf3D7(ΣFIC50: 1.33 to 3.34). These features of apoptosis and strong synergy with Artemisinin suggest that bischalcones possess promising antimalarial drug-like properties and may also act as a good partner drugs for artemisinin based combination therapies (ACTs) against Chloroquine resistant P. falciparum.
- Sharma, Upendra K.,Mohanakrishnan, Dinesh,Sharma, Nandini,Equbal, Danish,Sahal, Dinkar,Sinha, Arun K.
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p. 623 - 638
(2018/06/26)
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- Efficient synthesis of α-substituted-α-arylmethyl phosphonates using trichloroacetimidate C–C coupling method
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A simple convenient protocol for the synthesis of diethyl α,α-diaryl methylphosphonate derivatives 5a-f, 6b-f, 7a-f and 8a-f, diethyl α-alkenyl α-aryl methylphosphonates 9a-d and 10a-d and α-(oxoalkyl) α-aryl methylphosphonate 11a-d and 12a-d is described. Trichloroacetimidates 3a-d were treated with activated arenes, styrene, allyltrimethylsilane or silylenol ethers C-nucleophiles in the presence TMSOTf to afford the desired products in good yields and short reaction time.
- Fathalla, Walid,Pazdera, Pavel,El-Rayes, Samir,Ali, Ibrahim.A.I.
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p. 1681 - 1691
(2018/03/01)
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- Concise total synthesis of acylated phenolic glycosides vitexnegheteroin A and ovatoside D
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Starting from readily available vanillin and α-D-acetobromo glucose, two natural acylated phenolic glycosides vitexnegheteroin A and ovatoside D were synthesized for the first time in 4 steps with overall yields of 54% and 65%, respectively. The key steps involve the directly regioselective O-6 acylation of vanillin β-D-glucopyranoside with acyl chlorides, and simultaneous removal of the allyl protecting groups on the phenolic acid moiety and reduction of the aldehyde in the aglycon moiety by using Pd(PPh)3-NaBH4 system in one pot.
- Yan, Shiqiang,Ren, Sumei,Ding, Ning,Li, Yingxia
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- Facile one-pot synthesis of aliphatic bridged diaryloxy compounds, cyclic and crown ethers under mild conditions
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We report here the facile, room temperature, catalyst free, one pot synthesis of aliphatic bridged diaryloxy compounds, cyclic and crown ethers. Anhydrous potassium carbonate (K2CO3) as a mild base along with dimethyl sulfoxide gener
- Sakate, Sachin,Kamble, Sumit,Chikate, Rajiv,Rode, Chandrashekhar
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p. 462 - 470
(2017/03/27)
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- Synthesis and pharmacological properties of naturally occurring prenylated and pyranochalcones as potent anti-inflammatory agents
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An efficient approach has been developed for the synthesis of naturally occurring prenylated chalcones viz. kanzonol C (1), stipulin (2), crotaorixin (3), medicagenin (4), licoagrochalcone A (5) and abyssinone D (6) along with the pyranochalcones paratocarpin C (7), anthyllisone (8) and 3-O-methylabyssinone A (9). The key step of the synthesis is a Claisen-Schmidt condensation. Subsequently, their anti-inflammatory effects were investigated in lipopolysaccharides (LPSs)-induced RAW-264.7 macrophages. Of the synthesized chalcones, compounds 5 (IC50 = 10.41 μmol/L), 6 (IC50 = 9.65 μmol/L) and 8 (IC50 = 15.34 μmol/L) show remarkable activity with no cytotoxicity. Compound 9 (IC50 = 4.5 μmol/L) exhibits maximum (83.6%) nitric oxide (NO) inhibition, but shows slight cytotoxicity. The results reveal that the chalcones bearing the prenyl group at 3- and/or 5-position on ring A (acetophenone moiety), i.e., 1-4 and 7 show weak, or no inhibition activity, whereas chalcones having the prenyl group only on ring B (aldehyde part), i.e., 5, 6 and 8 show significant activity on the production of inflammatory mediated NO with no cytotoxicity.
- Damodar, Kongara,Kim, Jin-Kyung,Jun, Jong-Gab
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supporting information
p. 698 - 702
(2016/05/19)
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- Synthesis of C-4-Allyloxy-3 Methoxyphenylcalix[4] resorcinarene from Vanillin and Its application as adsorbent of Pb(II) metal cation
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C-4-allyloxy-3-methoxyphenylcalix[4]resorcinarene had been synthesized from vanillin and its application as adsorbent for Pb(II) metal ion had been carried out. The synthesis was conducted in three steps to obtain the product as pink solid in 78.17% yield. The structure elucidation of the product was performed by IR,1H-NMR and 13C-NMR. Adsorption experiments were carried out in a batch system under variation of medium acidity, interaction time and initial metal concentration. Adsorption kinetics was studied using Lagergren and Ho model, while adsorption isotherm was analyzed by Langmuir and Freundlich equations. The result showed that the Pb(II) adsorption was optimum at pH 4 and at interaction time of 30 minutes. The kinetic study showed that the adsorption of Pb(II) followed pseudo-second order of Ho model with adsorption rate (k) of 1.176 g mg-1 minute-1 . The adsorption followed the Langmuir isotherm model with equilibrium constant (K) was 7.28?10-5 L mol-1 , adsorption capacity (qm) was 1.538 mmol g-1 (318.67 mg/g) and adsorption energy was 33.67 kJ mol-1 .
- Kesuma, Endhy Putra,Ohto, Keisuke,Siswanta, Dwi
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p. 769 - 775
(2016/07/06)
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- Synthesis of cyclic peptides through ring-closing metathesis of photolabile protecting groups
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The new photolabile protecting groups 4-allyl-5-methoxy-3-nitrobenzyl (AMNB) and 4-allyl-5-methoxy-3-nitrobenzyloxycarbonyl (AMNBOC) with an allylic side chain can easily be obtained from vanillin. These protecting groups can be introduced on the C- as well as on the N-terminus of peptides, and subsequent ring-closing metatheses provides a straightforward protocol for the synthesis of cyclic peptides. The protecting groups can be removed under UVA irradiation (365 nm).
- Hoffmann, Judith,Kazmaier, Uli
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p. 411 - 420
(2015/02/19)
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- A Straightforward Approach towards Cyclic Photoactivatable Tubulysin Derivatives
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The development of a new photolabile protecting group containing an additional allyl functionality allows the synthesis of cyclic photoactivatable natural products. Cyclization occurs between the allyl moiety in the protecting group and a second double bond in the target molecule by means of ring-closing metathesis. Cyclization should increase the metabolic stability towards proteases. On the other hand, the conformational change should cause diminished biological activity. As illustrated for tubulysin derivatives, cyclic and photoactivatable drug candidates can easily be obtained in only two steps from simple building blocks through Ugi reaction and ring-closing metathesis. The photolabile protecting group is introduced by means of the isocyanide component during the Ugi reaction.
- Hoffmann, Judith,Kazmaier, Uli
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supporting information
p. 11356 - 11360
(2016/02/18)
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- Design, economical synthesis and antiplasmodial evaluation of vanillin derived allylated chalcones and their marked synergism with artemisinin against chloroquine resistant strains of Plasmodium falciparum
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The in vitro blood stage antiplasmodial activity of a series of allylated chalcones based on the licochalcone A as lead molecule was investigated against chloroquine (CQ) sensitive Pf3D7 and CQ resistant PfINDO strains of Plasmodium falciparum using SYBR Green I assay. Of the forty two chalcones tested, eight showed IC50 ≥ 5 μM. Structure-activity relationship (SAR) studies revealed 9 {1-(4-Chlorophenyl)-3-[3-methoxy-4-(prop-2-en-1-yloxy)phenyl] -prop-2-en-1-one} as the most potent (IC∑: 2.5 μM) against Pf3D7 with resistance indices of 1.2 and 6.6 against PfDd2 and PfINDO strains, respectively. Later on, the synergistic effects 9 with standard antimalarials {artemisinin (ART) and chloroquine (CQ)} were studied in order to provide the basis for the selection of the best partner drug. In vitro combinations of 9 with ART showed strong synergy against PfINDO (ΣFIC∑: 0.31-0.72) but additive to slight antagonistic effects (ΣFIC∑: 1.97-2.64) against Pf3D7. ΣFIC∑ 0.31 of ART+9 combination corresponded to a 320 fold and 3 fold reduction in IC∑ of 9 and ART, respectively. Similar combinations of 9 with CQ showed synergy to additivity to mild antagonism against the two strains {ΣFIC∑: 0.668-2.269 (PfINDO); 1.45-2.83 (Pf3D7)}. Drug exposure followed by drug withdrawal indicated that 9 taken alone at IC∑ killed rings, trophozoites and schizonts of P. falciparum. The combination of ART and 9 (1X ΣFIC∑) selectively inhibited the growth of rings while the 2X ΣFIC∑ combination of the same caused killing of rings without affecting trophozoites and schizonts. In contrast, the 1X combination of CQ and 9 (ΣFIC ∑: 0.5) killed rings and trophozoites. DNA fragmentation and loss of mitochondrial membrane potential (ΔΨm) in the 9 treated P. falciparum culture indicated apoptotic death in malaria parasites. Prediction of ADME properties revealed that most of the molecules did not violate Lipinski's parameters and have low TPSA value suggesting good absorption. The results suggest the promising drug-like properties of 9 against CQ resistant Pf and propensity for synergy with classical antimalarial drugs together with easy and economical synthesis.
- Sharma, Nandini,Mohanakrishnan, Dinesh,Sharma, Upendra Kumar,Kumar, Rajesh,Richa,Sinha, Arun Kumar,Sahal, Dinkar
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p. 350 - 368
(2014/05/06)
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- Vanillin and o-vanillin oligomers as models for dendrimer disassembly
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Linear analogs have been synthesized to model disassembling dendrimers. These linear analogs provide a facile synthesis to molecules that can be used to test new trigger groups and cleavage vectors. Vanillin and o-vanillin were used as the monomer units of these analogs and two trigger groups, allyl and o-nitrobenzyl, were chosen to test the disassembly process. Allyl triggered analogs 1a-d and 3a-d and o-nitrobenzyl triggered analogs 2a-c and 4a-c showed good to excellent disassembly as followed by the evolution of p-nitrophenoxide reporter ion by UV-Visible spectroscopy. The rate and yield of disassembly was shown to depend on experimental conditions as well as length of the cleavage vector.
- Kevwitch, Robert M.,Shanahan, Charles S.,McGrath, Dominic V.
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experimental part
p. 492 - 505
(2012/03/22)
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- Synthesis, characterization and antimicrobial screening of some novel chalcones and their derivatives
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Synthesis of some novel 2-(4-(allyloxy)-3-methoxyphenyl)-4H-chromen-4-ones 5a-f and 2-(4-(allyloxy)-3-methoxyphenyl)- 3-chloro-4H-chromen-4-ones 6a-f by oxidative cyclisation of (E)-3-(4-allyloxy)-3-methoxyphenyl)-1-(2-hydroxyphenyl) prop-2-en-1-ones usin
- Chate, Asha V.,Joshi, Ratnadeep S.,Mandhane, Priyanka G.,Gill, Charansingh H.
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p. 1642 - 1648
(2013/01/15)
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- Synthesis, in vitro antimicrobial and antioxidant activities of chalcone and flavone derivatives holding allylic substitutions
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In a wide search program towards new and efficient biological active agents, a series of chalcone and flavone derivatives holding allylic substitutions have been synthesized and tested for their in vitro antibacterial and antifungal activities. The synthe
- Adibi, Hadi,Mojarrad, Javid Shahbazi,Asgharloo, Hadi,Zarrini, Gholamreza
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scheme or table
p. 1318 - 1324
(2012/06/04)
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- Synthesis of methoxyfumimycin with 1,2-addition to ketimines
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(Chemical Equation Presented) The synthesis of (±)-methoxyfumimycin, a potential new bacterial peptide deformylase (PDF) inhibitor, is reported. To generate the stereogenic fully substituted carbon, the key step is a 1,2-addition of amethylGrignard reagent to a ketimine. The overall synthetic strategy involves a Dakin oxidation of a vanillin derivative, Friedel-Crafts acylation, Claisen rearrangement, lactonization, and rhodium-catalyzed olefin isomerization.
- Gross, Patrick J.,Hartmann, Caroline E.,Nieger, Martin,Braese, Stefan
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supporting information; experimental part
p. 229 - 232
(2010/04/24)
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- The total synthesis of (±)-fumimycin
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The antibiotic agent fumimycin has been synthesized for the first time. This natural product was found to inhibit the bacterial peptide deformylase and may represent a lead structure to a class of novel antibacterials. Our synthetic strategy towards fumimycin involved the following steps: Dakin oxidation of an aldehyde functionality, conversion of an oxime through radical fragmentation to form an N-diphenylphosphoryl group, construction of an α-trisubstituted amine by 1,2-addition to a ketimine, a Claisen rearrangement with subsequent transition-metal-catalyzed olefin isomerization to install a propenyl chain and final amidation. Peptide deformylase (PDF)-inhibitor synthesis: A strategy involving amine formation through addition to a ketimine has been successfully employed for the first total synthesis of the antibiotic agent fumimycin (see scheme).
- Gross, Patrick J.,Braese, Stefan
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supporting information; experimental part
p. 12660 - 12667
(2011/02/22)
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- Improved iterative synthesis of linearly disassembling dendrons
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Figure presented. We report a significant improvement in the synthesis of disassembling dendritic structures by using 4-hydroxy-3-nitrobenzoic acid as the building block. We have prepared multigram quantities of first- through third-generation linearly disassembling dendrons containing a [3-N,4-O]-benzylaryl ether disassembly pathway, capped by a vanillin-derived phenyl allyl ether trigger, and a p-nitrophenoxy (PNP) reporter group. The disassembly process of these materials was initiated by allyl deprotection and monitored by the absorbance of the PNP reporter unit in the UV-vis. Modification of the disassembly conditions for the allyl trigger resulted in decreased disassembly times, decreased incubation time for onset of disassembly from minutes to seconds, and allowed observation of indicative rate differences between generations not seen with the previously reported conditions.
- Ortiz, Adrian,Shanahan, Charles S.,Sisk, David T.,Perera, Sujeewa C.,Rao, Pallavi,McGrath, Dominic V.
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experimental part
p. 6154 - 6162
(2010/11/04)
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- A chemoselective aerobic oxidation of benzylic azides catalyzed by molybdenum xanthate in an aqueous medium
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A mild molybdenum-catalyzed, aerobic, chemoselective oxidation of benzylic azides to the corresponding aldehydes in an aqueous medium that tolerates a variety of functional groups including alcohols, esters, ketones, halides and olefins is described.
- Maddani, Mahagundappa,Prabhu, Kandikere Ramaiah
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p. 4526 - 4530
(2008/09/21)
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- A combined RCM-Bischler-Napieralski strategy towards the synthesis of the carbon skeleton of excentricine and related stephaoxocanes
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A convenient synthetic approach to a cyclodeca[ij]isoquinoline derivative, which embodies the carbon skeleton of excentricine and related stephaoxocanes, is described. The synthesis involves the combined use of ring closing metathesis and Bischler-Napiera
- Larghi, Enrique L.,Kaufman, Teodoro S.
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experimental part
p. 9921 - 9927
(2009/04/11)
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- Synthesis and anti-bacterial properties of mono-carbonyl analogues of curcumin
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The synthesis of three series of curcumin analogues with mono-carbonyl is described. Their in vitro antibacterial activities against seven Gram-positive and Gram-negative bacteria were tested and the effect of substituents on the aryl ring and the space structure of the linking strain were discussed. It was observed that part of the derivatives displayed significant activity when compared with curcumin and most of them exhibited activity against the ampicillin-resisted Enterobacter cloacae. Compounds A12, B09, B13, B14 and C09 show remarkable antibacterial activity in vitro. The result showed that heterocycle or long-chain substituents may enhance the activity of curcumin analogues.
- Liang, Guang,Yang, Shulin,Jiang, Lijuan,Zhao, Yu,Shao, Lili,Xiao, Jian,Ye, Faqing,Li, Yueru,Li, Xiaokun
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p. 162 - 167
(2008/09/19)
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- Synthesis and anti-inflammatory activities of mono-carbonyl analogues of curcumin
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Curcumin has been extensively studied for its anti-inflammatory activities. However, its potential beneficial effects on various disease preventions and treatments are limited by its unstable structure. The β-diketone moiety renders curcumin to be rapidly metabolized by aldo-keto reductase in liver. In the present study, a series of curcumin analogues with more stable chemical structures were synthesized and several compounds showed an enhanced ability to inhibit lipopolysaccharide (LPS)-induced TNF-α and IL-6 synthesis in macrophages.
- Liang, Guang,Li, Xiaokun,Chen, Li,Yang, Shulin,Wu, Xudong,Studer, Elaine,Gurley, Emily,Hylemon, Phillip B.,Ye, Faqing,Li, Yueru,Zhou, Huiping
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p. 1525 - 1529
(2008/09/19)
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- Synthesis of (±)-12-methoxyherbertenediol dimethyl ether
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Efficient total synthesis of (±)-12-methoxyherbertenediol dimethyl ether and 12-homoherbertenediol was accomplished starting from vanillin employing a Claisen rearrangement-RCM reaction-based approach. Copyright Taylor & Francis Group, LLC.
- Srikrishna,Kumar, S. Ratna,Ravikumar
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p. 4123 - 4140
(2008/04/12)
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- Solid-supported acids as mild and versatile reagents for the deprotection of aromatic ethers
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Equation Presented p-Toluene sulfonic acid (p-TsOH) immobilized either on polystyrene (PS) or silica (Si) was found to be effective in cleaving aromatic ethers containing isopropyl, tert-butyl, allyl, and benzyl groups, as well as mono-, di-, and trimethoxylated benzyl groups, in moderate to excellent yields (54-95%). These protecting groups could be selectively deprotected when they were simultaneously present on the same or different aromatic rings in a substrate.
- Ploypradith, Poonsakdi,Cheryklin, Pannarin,Niyomtham, Nattisa,Bertoni, Daniel R.,Ruchirawat, Somsak
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p. 2637 - 2640
(2008/02/08)
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- Investigation of selective mono-deallylation of O,O′-diallylcatechols and 3-methylene-1,5-benzodioxepanes
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Selective mono-deallylation of O,O′-diallylcatechols using 10% Pd/C was investigated to give the corresponding allylphenols. A similar reaction of 3-methylene-1,5-benzodioxepanes afforded O-methacryl catecohols. When substrates bearing various substituents on the benzene ring were subjected to the reaction, regioselective cleavage of an ether bond occurred at the side of para position to an electron-withdrawing group on the aromatic ring. On the other hand, an electron-donating group did not cause any selectivity.
- Hayashida, Maiko,Ishizaki, Miyuki,Hara, Hiroshi
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p. 1299 - 1303
(2008/09/20)
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- Surfactant-mediated solvent-free dealkylative cleavage of ethers and esters and trans-alkylation under neutral conditions
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A simple, surfactant-mediated, one-pot, solvent-free dealkylative cleavage of aryl ethers and esters followed by subsequent optional trans-alkylation under essentially neutral conditions has been developed.
- Bhattacharya, Apurba,Patel, Nitin C.,Vasques, Tomas,Tichkule, Ritesh,Parmar, Gaurang,Wu, Jiejun
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p. 565 - 567
(2007/10/03)
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- Total synthesis and stereochemical confirmation of manassantin A, B, and B1
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Stereocontrolled total syntheses of manassantins A, B, and B1 and saucerneol are described for the first time based on a novel cycloetherification of end-differentiated benzylic alcohols as a common intermediate.
- Hanessian, Stephen,Reddy, Gone Jayapal,Chahal, Navjot
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p. 5477 - 5480
(2007/10/03)
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- Convenient synthesis of (E)-methyl O-alkylferulates: Formal synthesis of O-geranylconiferyl alcohol, a metabolite of Fagara rhetza
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A convenient two step stereoselective synthesis of (E)-methyl O-alkylferulate 5a-c is described from vanillin 1. Reaction of vanillin 1 with allyl-, prenyl- or geranyl- bromide 2a-c has afforded alkyl ethers 3a-c which on reaction with phosphorane 4, under microwave irradiation, gives (E)-methyl O-alkylferulates 5a-c in high yield. In an alternative approach vanillin 1 on reaction with phosphorane 4 provides (E)-methyl ferulate 6 which on reaction with the corresponding bromides 2a-c gives (E)-methyl O-alkylferulates 5a-c.
- Mahajan, Rajesh P.,Patil, Shamkant L.,Mali, Raghao S.
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p. 328 - 331
(2007/10/03)
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- An improved and versatile method for the rapid synthesis of aryldihydrobenzofuran systems by a boron tribromide-mediated cyclization reaction
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Boron tribromide is presented as a highly reactive reagent that simultaneously allows the demethylation and fully diastereoselective cyclization of different precursor molecules, obtained by an aldol-type reaction, to a series of hydroxylated aryldihydrobenzofuran systems in racemic form. The latter are often found as key structures in natural compounds of different classes. Syntheses of educts, which mainly took advantage of a versatile Rieche formylation, are also described.
- Detterbeck, Richard,Hesse, Manfred
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p. 343 - 360
(2007/10/03)
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- Regioselective protection of the 4-hydroxyl of 3,4-dihydroxy-benzaldehyde
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The regioselective protection of the 4-hydroxyl group of 3,4-dihydroxy-benzaldehyde was accomplished with seven different protecting groups (benzyl, p-methoxybenzyl, o-nitrobenzyl, 2,6-dichlorobenzyl, 3,4-dichlorobenzyl, vinyl and propargyl) in yields ranging between 67-75percent.
- Plourde, Guy L.,Spaetzel, Randy R.
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p. 697 - 705
(2007/10/03)
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- An efficient biomimetic cleavage of gem-diacetates to aldehydes by β-cyclodextrin under neutral conditions in aqueous medium
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The cleavage of gem-diacetates to aldehydes, a widely used protecting group in organic synthesis, has been achieved for the first time under neutral conditions in aqueous medium using β-cyclodextrin as catalyst. The main advantage of the present methodology is that it can be used with compounds having a variety of functional groups since the cleavage is carriedout under neutral conditions in aqueous medium.
- Arjun Reddy,Rajender Reddy,Bhanumathi,Rama Rao
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p. 273 - 277
(2007/10/03)
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- The synthesis of new polyheterocyclic compounds
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The synthesis of new polyheterocyclic compounds are reported. All synthons and final products have been described and established structure by spectroscopic methods.
- Hassikou, Amina,Benabdallah, Ghita Amine,Dinia, Mohammed Naceur,Bougrin, Khalid,Soufiaoui, Mohamed
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p. 5857 - 5861
(2007/10/03)
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- Syntheses of isochromane analogues of the michellamines and korupensamines
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Syntheses of the oxygen analogues 6, 7 and 8 of the michellamines 1 and korupensamines 2 are described. Racemic 5-iodo-6,8-dimethoxy-trans-1,3-dimethylisochromane 10 was synthesised in eleven steps from 2,4-dimethoxybenzaldehyde in an overall yield of 51%
- De Koning, Charles B.,Michael, Joseph P.,Van Otterlo, Willem A.L.
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p. 799 - 811
(2007/10/03)
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- Feeding-deterrent activity of α-asarone isomers against some stored Coleoptera
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All isomers of α-asarone [(E)-4-prop-1-enyl-1,2,5-trimethoxybenzene] were tested for their feeding deterrent activity against adults of Sitophilus granarius and Tribolium confusum and larvae of Trogoderma granarium and Tribolium confusum. (E)-2-prop-1-eny
- Poplewski, Janusz,Lozowicka, Bozena,Dubis, Alina T.,Lachowska, Barbara,Winiecki, Zbigiew,Nawrot, Jan
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p. 560 - 564
(2007/10/03)
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- Synthesis and hypolipidemic and antiplatelet activities of α-asarone isomers in humans (in vitro), mice (in vivo), and rats (in vivo)
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A series of α-asarone isomers was synthesized and investigated for their hypolipidemic and antiplatelet activity. Considering the hypolipidemic activity in rats at a dose of 80 mg/kg/day, some isomers were more potent than clofibrate at 150 mg/kg. Compoun
- Poplawski,Lozowicka,Dubis,Lachowska,Witkowski,Siluk,Petrusewicz,Kaliszan,Cybulski,Strzalkowska,Chilmonczyk
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p. 3671 - 3676
(2007/10/03)
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- An investigation into the electronic effects of substituents at the 6-position on the biological activity of isochromanquinones
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Three isochromanquinones 10, 11 and 12 were synthesised in order to determine the effect of electronic effects of groups at the 6-position on the biological activity of these compounds.
- Green, Ivan R.,De Koning, Charles B.,Hugo, Victor I.
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p. 112 - 119
(2007/10/03)
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- Crystal structures of 1,2,5-trimethoxy-3-(1-propenyl)benzene and 1,3,5-trimethoxy-2-(1-propenyl)benzene
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The crystal structures of 1,2,5-trimethoxy-3-(1-propenyl)benzene (D) and 1,3,5-trimethoxy-2-(1-propenyl)benzene (F) have been determined by X-ray diffraction methods. The compounds crystallize in the monoclinic system, space group P21/c for (D)
- Wolska,Poplawski,Lozowicka
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p. 2331 - 2341
(2007/10/03)
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- Synthesis of (+/-)-arthrographol
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A total synthesis of (+/-)-arthrographol (1) in seven steps from vanillin is reported.Key steps in the synthesis are a single-step conversion of 5-allylvanillin (2) into the benzofuranmethanol 6, alkylation of the chloride 25 with the lithium anion of cro
- Ayer, William A.,Craw, Peter A.
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p. 1909 - 1916
(2007/10/02)
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