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Benzoic acid

About: Benzoic acid is a research topic. Over the lifetime, 11832 publications have been published within this topic receiving 167127 citations. The topic is also known as: Retardex & E210.


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Journal ArticleDOI
TL;DR: The above described structure activity relationship renders it likely that these chloride channel blockers possess several sites of interaction: The negatively charged carboxylate group, the secondary amine group which probably carries a positive partial charge, and for the very potent agents an additional negative partial charge at the respective-Cl or-NO2 substituent.
Abstract: On the basis of our findings with diphenylamine-2-carboxylate [5] we have searched for compounds which possess an even higher affinity for the Cl−-channels in the basolateral membrane of the thick ascending limb of the loop of Henle. To quantitiy the inhibitory potency, we performed measurements of the equivalent short circuit current, corresponding to the secondary active transport of Cl− [8] and measurements of the voltage across the basolateral membrane. A survey of 219 compounds reveals that relatively simple modifications in the structure of diphenylamine-2-carboxylate led to very potent blockers such as 5-nitro-2-(3-phenylpropylamino)-benzoate which inhibits the short circuit current half maximally (IC50) at 8·10−8 mol/l. A comparison of the structural formula and the respective IC50 values leads to several empirical conclusions: 1. The potent compounds are lipophilic due to the apolar residue (e.g. phenyl- or cycloalkyl group). Replacing this part of the molecule by an aliphatic chain (up to 4 C-atoms) leads to inactive compounds. 2. Most of the inhibitors are secondary amines. Linking other than with-NH- between the phenyl ring and the benzoic acid results in inactive compounds. Tertiary amines, such as in case of 2-(N,N-diphenylamine) benzoic acid or N-methylphenylaminebenzoic acid are poorly active. 3. The carboxylate group of the benzoate moiety must be in ortho position to the amino group. 4. Introduction of substituents into the benzoate moiety e.g.-NO2 (in meta position to the carboxylate group), or by-Cl (in para position to the carboxylate group) results in an increase of inhibitory potency. 5. A-CH2-,-C2H4-,-C3H6-) spacer between the amino bridge and the phenyl ring increases the affinity for the Cl−-channel by several orders of magnitude. The above described structure activity relationship renders it likely that these chloride channel blockers possess several sites of interaction: The negatively charged carboxylate group, the secondary amine group which probably carries a positive partial charge, and for the very potent agents (nos. 130, 143, 144, and 145) an additional negative partial charge at the respective-Cl or-NO2 substituent. Finally, also an apolar interaction with an cycloalkyl or cycloaryl residue seems to be required, and this site of interaction has a defined spacing from the secondary amino nitrogen.

369 citations

Journal ArticleDOI
TL;DR: There is a relationship between intracellular pH, phosphofructokinase inhibition and CO2 production, suggesting that the antifungal action of Benzoate is caused by an accumulation of benzoate at low external pH, which lowers the intrace cellular pH into the range where phosphofructureokinase is sensitive.
Abstract: A method is described for the determination of the pH of intracellular water based on the distribution of [14C]benzoate (0.01 mM) between intra- and extra-cellular water. Benzoate at higher concentrations (2-10mM) enters the yeast cell in the undissociated form, and its neutralization within the cell can cause a shift of the pH of the intracellular water by more than 1 pH unit. Benzoate causes an accumulation of the two hexose monophosphates of yeast glucose fermentation and a decrease in intermediates beyond phosphofructokinase, suggesting inhibition at this stage. Benzoate also causes a concomitant fall in [ATP]. Phosphofructokinase is inhibited to a greater extent than hexokinase at acid pH. There is a relationship between intracellular pH, phosphofructokinase inhibition and CO2 production, suggesting that the antifungal action of benzoate is caused by an accumulation of benzoate at low external pH, which lowers the intracellular pH into the range where phosphofructokinase is sensitive. The subsequent inhibition of glycolysis causes a fall in [ATP] and thus restricts growth.

364 citations

Journal ArticleDOI
TL;DR: It is concluded that in healthy and virus-inoculated tobacco, SA is formed from cinnamic acid via benzoic acid, the immediate precursor of SA.
Abstract: Salicylic acid (SA) is a likely endogenous regulator of localized and systemic disease resistance in plants. During the hypersensitive response of Nicotiana tabacum L. cv Xanthi-nc to tobacco mosaic virus (TMV), SA levels rise dramatically. We studied SA biosynthesis in healthy and TMV-inoculated tobacco by monitoring the levels of SA and its likely precursors in extracts of leaves and cell suspensions. In TMV-inoculated leaves, stimulation of SA accumulation is accompanied by a corresponding increase in the levels of benzoic acid. 14C-Tracer studies with cell suspensions and mock-or TMV-inoculated leaves indicate that the label moves from trans-cinnamic acid to SA via benzoic acid. In healthy and TMV-inoculated tobacco leaves, benzoic acid induced SA accumulation. o-Coumaric acid, which was previously reported as a possible precursor of SA in other species, did not increase SA levels in tobacco. In healthy tobacco tissue, the specific activity of newly formed SA was equal to that of the supplied [14C]benzoic acid, whereas in TMV-inoculated leaves some isotope dilution was observed, presumably because of the increase in the pool of endogenous benzoic acid. We observed accumulation of pathogen-esis-related-1 proteins and increased resistance to TMV in benzoic acid- but not in o-coumaric acid-treated tobacco leaves. This is consistent with benzoic acid being the immediate precursor of SA. We conclude that in healthy and virus-inoculated tobacco, SA is formed from cinnamic acid via benzoic acid.

343 citations

Journal ArticleDOI
TL;DR: In this paper, the synthesis of acrolein by catalytic gas-phase dehydration of biomass-derivate glycerol was studied over various solid catalysts with a wide range of acid base properties.

326 citations

Journal ArticleDOI
TL;DR: In this paper, the C−H bond at their 2'-position was cleaved in the presence of a catalyst system of Pd(OAc)2 and Cu(OAC)2 with a base under air.
Abstract: N-(2‘-Phenylphenyl)benzenesulfonamides react with acrylate esters accompanied via cleavage of the C−H bond at their 2‘-position in the presence of a catalyst system of Pd(OAc)2 and Cu(OAc)2 and a base under air to produce 5,6-dihydro-5-(benzenesulfonyl)phenanthridine-6-acetate derivatives in high yields. The reactions of benzoic acid with butyl acrylate and styrene can also give 3-[(butoxycarbonyl)methyl]phthalide and 3-phenylisocoumarin, respectively.

322 citations


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Performance
Metrics
No. of papers in the topic in previous years
YearPapers
2023207
2022519
2021217
2020279
2019315
2018332