- Triphenylphosphine-mediated serendipitous synthesis of alkyl cinnamates through the reaction of 3-hydroxy-4-methoxybenzaldehyde and dialkyl acetylenedicarboxylates
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Alkyl cinnamates are formed in fairly good yields from the reaction of dialkyl acetylenedicarboxylates and 3-hydroxy-4-methoxybenzaldehyde in the presence of triphenylphosphine. Copyright Taylor & Francis Inc.
- Yavari, Issa,Djahaniani, Hoorieh,Moradi, Logman,Nasiri, Farough
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- Synthetic Guaiacol Derivatives as Promising Myeloperoxidase Inhibitors Targeting Atherosclerotic Cardiovascular Disease
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Myeloperoxidase (MPO) is known to cause oxidative stress and inflammation leading to cardiovascular disease (CVD) complications. MPO-mediated oxidation of lipoproteins leads to dysfunctional entities altering the landscape of lipoprotein functionality. The specificity of guaiacol derivatives toward preventing MPO-mediated oxidation to limit MPO's harmful effects is unknown. Diligent in silico studies were accomplished for a portfolio of compounds with guaiacol as a building block. The compounds’ activity toward MPO inhibition was also validated. The role of these chemical entities in controlling MPO-mediated oxidation of lipoproteins (LDL and HDL) was shown to agree with our approach of developing powerful MPO inhibitors. The mechanism of MPO inhibition was demonstrated to be reversible in nature. This study reveals that there is great potential for guaiacol derivatives as therapeutics for CVD by modulating lipid profiles, reducing atherosclerotic plaque burden, and subsequently optimizing cardiovascular functions.
- Premkumar, Jayaraj,Sampath, Parthasarathy,Sanjay, Rajagopalan,Chandrakala, Aluganti,Rajagopal, Desikan
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supporting information
p. 1187 - 1199
(2020/05/25)
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- Search for novel histone deacetylase inhibitors. Part II: Design and synthesis of novel isoferulic acid derivatives
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Previously, we described the discovery of potent ferulic acid-based histone deacetylase inhibitors (HDACIs) with halogeno-acetanilide as novel surface recognition moiety (SRM). In order to improve the affinity and activity of these HDACIs, twenty seven isoferulic acid derivatives were described herein. The majority of title compounds displayed potent HDAC inhibitory activity. In particular, IF5 and IF6 exhibited significant enzymatic inhibitory activities, with IC50 values of 0.73 ± 0.08 and 0.57 ± 0.16 μM, respectively. Furthermore, these compounds showed moderate antiproliferative activity against human cancer cells. Especially, IF6 displayed promising profile as an antitumor candidate with IC50 value of 3.91 ± 0.97 μM against HeLa cells. The results indicated that these isoferulic acid derivatives could serve as promising lead compounds for further optimization.
- Lu, Wen,Wang, Fang,Zhang, Tao,Dong, Jinyun,Gao, Hongping,Su, Ping,Shi, Yaling,Zhang, Jie
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p. 2707 - 2713
(2014/05/06)
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- Optical control of TRPV1 channels
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Controlling pain with light: TRPV1 channels mediate the response to noxious heat and can be activated by capsaicin, the major ingredient of chili pepper. Novel azobenzene photoswitches can be used for the optical control of TRPV1. One of these compounds antagonizes capsaicin in a light-dependent fashion, demonstrating that a photoswitchable antagonist and an agonist can be applied in concert to modulate ion channel activity. Copyright
- Stein, Marco,Breit, Andreas,Fehrentz, Timm,Gudermann, Thomas,Trauner, Dirk
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supporting information
p. 9845 - 9848
(2013/09/23)
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- Inhibitory effects of substituted cinnamic acid esters on mushroom tyrosinase
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A series of substituted cinnamic acid esters were synthesized and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were evaluated. Compound 8 was found to be the most potent inhibitor with IC 50 value of 5.60μM. Preliminary structure activity relationships (SARs) were concluded. The inhibition kinetics analyzed by Lineweaver-Burk plots revealed that compound 8 was anti-competitive inhibitor.
- Zhang, Zhenghua,Liu, Jinbing,Wu, Fengyan,Zhao, Liangzhong
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p. 529 - 534
(2013/07/26)
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- Zn(OTf)2-promoted chemoselective esterification of hydroxyl group bearing carboxylic acids
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Selective esterification of aliphatic and aromatic carboxylic acids with various alcohols is studied using triphenylphosphine, I2, and a catalytic amount of Zn(OTf)2. Use of this catalyst allows the formation of esters at a faster rate with good to excellent yield by activating the in situ generated acyloxyphosphonium ion intermediate. During the esterification process, both their aromatic and aliphatic hydroxyl groups are fully preserved from transesterification. The results show that the bulkiness and the reactivity of this doubly activated intermediate III control the selectivity and the rate of the reaction, respectively. The method is also useful for direct amidation reactions.
- Mamidi, Narsimha,Manna, Debasis
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p. 2386 - 2396
(2013/05/21)
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- Very short and efficient syntheses of the spermine alkaloid kukoamine A and analogs using isolable succinimidyl cinnamates
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Direct selective acylation of the primary amino functions of spermine and spermidine with a variety of isolable succinimidyl cinnamates, followed by catalytic hydrogenation, gave high yields of the spermine alkaloid kukoamine A and analogs suitable for structure-activity relationship studies. Suitable succinimidyl cinnamates were readily obtained through Wittig reaction of aromatic aldehydes with the ylides Ph3P=CRCO2Me, followed by saponification and activation with N-hydroxysuccinimide in the presence of N,N'-dicyclohexylcarbodiimide. Copyright
- Garnelis, Thomas,Athanassopoulos, Constantinos M.,Papaioannou, Dionissios,Eggleston, Ian M.,Fairlamb, Alan H.
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p. 264 - 265
(2007/10/03)
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- Synthesis and HIV-1 integrase inhibitory activities of caffeic acid dimers derived from Salvia officinalis
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The synthesis of two caffeoyl-coumarin conjugates, derived from sagecoumarin, has been accomplished, starting from ferulic acid, isoferulic acid and sesamol. Both compounds exhibited potent inhibitory activities at micromolar concentrations against HIV-1 integrase in 3′-end processing reaction but were less effective against HIV-1 replication in a single-round infection assay of HeLa-β-gal-CD4+ cells.
- Bailly, Fabrice,Queffelec, Clemence,Mbemba, Gladys,Mouscadet, Jean-Francois,Cotelle, Philippe
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p. 5053 - 5056
(2007/10/03)
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- HYDROXAMID ACID DERIVATIVES AS HISTONE DEACETYLASE (HDAC) INHIBITORS
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A compound having the following formula (I): wherein R?1? is N-containing heterocyclic ring optionally substituted with one or more suitable substituent(s), R?2? is hydroxyamino, R?3? is hydrogen or a suitable substituent, L?1? is -(CH?2#191)?n#191- (wherein n is an integer of 0 to 6) optionally substituted with one or more suitable substituent(s), wherein one or more methylene(s) may be replaced with suitable heteroatom(s), and L?2? is lower alkenylene, or a salt thereof. The compound is useful as a histone deacetylase inhibitor.
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- HDAC inhibitor
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A compound having the following formula (I): wherein R1 is N-containing heterocyclic ring optionally substituted with one or more suitable substituent(s), R2 is hydroxyamino, R3 is hydrogen or a suitable substituent, L1 is —(CH2)n— (wherein n is an integer of 0 to 6) optionally substituted with one or more suitable substituent(s), wherein one or more methylene(s) may be replaced with suitable heteroatom(s), and L2 is lower alkenylene, or a salt thereof. The compound is useful as a histone deacetylase inhibitor.
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- Syntheses of certain 3-aryl-2-propenoates and evaluation of their cytotoxicity
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A series of 3-aryl-2-propenoates including cinnamates, (E)-methyl/ethyl 3-[2-(1,4-dimethoxy-5,8-dione)naphthalenyl]-2-propenoates (8ba, 8bb) and (E)-methyl/ethyl 3-[2-(1,4-dihydroxy-9,10-dione)anthracenyl]-2-propenoates (9aa, 9ab) was synthesized and eval
- Nam, Nguyen-Hai,You, Young-Jae,Kim, Yong,Hong, Dong-Ho,Kim, Hwan-Mook,Ahn, Byung Zun
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p. 1173 - 1176
(2007/10/03)
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- Spectromagnetic investigation of the active species in the oxidation of propenoidic phenols catalysed by [N,N′-bis(salicylidene)-ethane-1,2-diaminato]cobalt(II)
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The oxidation of propenoidic phenols by molecular oxygen, catalysed by [N,N′-bis(salicylidene)ethane-1,2-diaminato]cobalt(II) [Co(salen)], was studied in different solvents and for variously substituted phenols to find processes alternative to those reported for the removal of polyphenols from waste waters in the paper industry. The reaction of methyl E-4-hydroxy-3-methoxycinnamate (E-methyl ferulate) selectively gave the corresponding 4-hydroxybenzoic acid and 4-hydroxybenzaldehyde; yields are highest in chloroform, good in methanol and very low in pyridine. Conversion was high with E-methyl ferulate, lower with methyl E-4-hydroxycinnamate, while the other phenols, methyl E-3-hydroxy-4-methoxycinnamate (E-methyl isoferulate) and methyl E-3-chloro-4-hydroxycinnamate, did not react. An EPR investigation of the reaction mixtures, performed on samples taken at different reaction times, demonstrated that the most probable mechanism involves reactions (i)-(iii). The [CoII(salen)] + ROH + O2 ? [CoIII(salen)(ROH)(O2)]- (i) [CoIII(salen)(ROH)(O2)- + ROH ?[CoIII(salen)(ROH)(RO?)] + HO2- (ii) [CoIII(salen)(ROH)(RO?)] + HO2- = [CoIII(salen)(RO-)(RO?)] + H2O2 (iii) superoxocobalt radical, [CoIII(salen)(ROH)(O2)]-, and the phenoxy cobalt radical, [CoIII(salen)(RO-)(RO?)], are the EPR-active species; RO? is suggested easily to dissociate from [CoIII(salen)(RO-)(RO?)] and, reacting with O2 at the β-carbon of the allyl substituent, probably gives a dioxethane. This decomposes to aldehyde and acid. The phenol electron-donor properties promote the formation of the superoxocobalt derivative and consequently favour the formation of the phenoxy cobalt radical; a too high stability of this radical does not favour its evolution into oxidation products.
- Bolzacchini, Ezio,Canevali, Carmen,Morazzoni, Franca,Orlandi, Marco,Rindone, Bruno,Scotti, Roberto
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p. 4695 - 4699
(2007/10/03)
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- An Ullmann ether reaction involving an alkynyl substrate: A convergent route to a combretastatin intermediate
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We found that we could employ a disubstituted alkynyl halide in an Ullmann ether reaction to produce the cis-alkene intermediate 3 of the combretastatin natural products.
- Blase,Banerjee
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p. 3187 - 3197
(2007/10/02)
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- 6-O-α-L-(2''-O- AND 3''-O-ISOFERULOYL)RHAMNOPYRANOSYLCATALPOLS FROM PREMNA JAPONICA
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From the methanol extract of the leaves of Premna japonica, two new monoacyl 6-O-α-L-rhamnopyranosylcatalpols were isolated.The structures of these compounds were determined to be 6-O-α-L-(2''-O-isoferuloyl and 3''-O-isoferuloyl)rhamnopyranosylcatalpols by NMR spectroscopy and chemical conversions.Key Word Index - Premna japonica; Verbenaceae; iridoid; 6-O-α-L-(rhamnopyranosylcatalpol; 6-O-α-L-(2''-O-isoferuloyl) rhamnopyranosylcatalpol; 6-O-α-L-(3''-O-isoferuloyl) rhamnopyranosylcatalpol.
- Otsuka, Hideaki,Sasaki, Yukari,Yamasaki, Kazuo,Takeda, Yoshio,Seki, Tarow
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p. 3069 - 3072
(2007/10/02)
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- Studies on the Constituents of Cistanchis Herba. III. Isolation and Structures of New Phenylpropanoid Glycosides, Cistanosides A and B
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Two new phenylpropanoid glycosides, named cistanoside A (III) and cistanoside B (IV), were isolated from the whole plant of Cistanche salsa (C.A.Mey.) G.Beck (Orobanchaceae), together with acteoside (I) and echinacoside (II).The structures of III and IV were determined to be 2-(4-hydroxy-3-methoxyphenyl)ethyl O-α-L-rhamnopyranosyl-(1->3)-O-6)>-(4-O-caffeoyl)-β-D-glucopyranoside and 2-(4-hydroxy-3-methoxyphenyl)ethyl O-α-L-rhamnopyranosyl-(1->3)-O-6)>-(4-O-feruloyl)-β-D-glucopyranoside, respectively, on the basis of chemical and spectral data.Keywords - Cistanche salsa; Cistanchis Herba; Orobanchaceae; phenylpropanoid glycoside; cystanoside A; cistanoside B; echinacoside; acteoside.
- Kobayashi, Hiromi,Karasawa, Hiroko,Miyase, Toshio,Fukushima, Seigo
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p. 3009 - 3014
(2007/10/02)
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