97966-29-5Relevant academic research and scientific papers
Triphenylphosphine-mediated serendipitous synthesis of alkyl cinnamates through the reaction of 3-hydroxy-4-methoxybenzaldehyde and dialkyl acetylenedicarboxylates
Yavari, Issa,Djahaniani, Hoorieh,Moradi, Logman,Nasiri, Farough
, p. 2149 - 2153 (2005)
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.
Synthetic Guaiacol Derivatives as Promising Myeloperoxidase Inhibitors Targeting Atherosclerotic Cardiovascular Disease
Premkumar, Jayaraj,Sampath, Parthasarathy,Sanjay, Rajagopalan,Chandrakala, Aluganti,Rajagopal, Desikan
supporting information, p. 1187 - 1199 (2020/05/25)
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.
Search for novel histone deacetylase inhibitors. Part II: Design and synthesis of novel isoferulic acid derivatives
Lu, Wen,Wang, Fang,Zhang, Tao,Dong, Jinyun,Gao, Hongping,Su, Ping,Shi, Yaling,Zhang, Jie
, p. 2707 - 2713 (2014/05/06)
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.
Zn(OTf)2-promoted chemoselective esterification of hydroxyl group bearing carboxylic acids
Mamidi, Narsimha,Manna, Debasis
, p. 2386 - 2396 (2013/05/21)
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.
Optical control of TRPV1 channels
Stein, Marco,Breit, Andreas,Fehrentz, Timm,Gudermann, Thomas,Trauner, Dirk
supporting information, p. 9845 - 9848 (2013/09/23)
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
Inhibitory effects of substituted cinnamic acid esters on mushroom tyrosinase
Zhang, Zhenghua,Liu, Jinbing,Wu, Fengyan,Zhao, Liangzhong
, p. 529 - 534 (2013/07/26)
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.
Very short and efficient syntheses of the spermine alkaloid kukoamine A and analogs using isolable succinimidyl cinnamates
Garnelis, Thomas,Athanassopoulos, Constantinos M.,Papaioannou, Dionissios,Eggleston, Ian M.,Fairlamb, Alan H.
, p. 264 - 265 (2007/10/03)
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
Synthesis and HIV-1 integrase inhibitory activities of caffeic acid dimers derived from Salvia officinalis
Bailly, Fabrice,Queffelec, Clemence,Mbemba, Gladys,Mouscadet, Jean-Francois,Cotelle, Philippe
, p. 5053 - 5056 (2007/10/03)
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.
HYDROXAMID ACID DERIVATIVES AS HISTONE DEACETYLASE (HDAC) INHIBITORS
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Page 81, (2010/02/07)
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.
