Aristoxazole Analogues. Conversion of 8-Nitro-1-naphthoic Acid to 2-Methylnaphtho[1,2-d]oxazole-9-carboxylic Acid: Comments on the Chemical Mechanism of Formation of DNA Adducts by the Aristolochic Acids

2012 ◽  
Vol 75 (7) ◽  
pp. 1414-1418 ◽  
Author(s):  
Horacio A. Priestap ◽  
Manuel A. Barbieri ◽  
Francis Johnson
Keyword(s):  
Carboxylic Acid ◽  
Dna Adducts ◽  
Chemical Mechanism ◽  
Mechanism Of Formation ◽  
Aristolochic Acids ◽  
Naphthoic Acid

Pulse polarographic study of the behaviour of some o,o'-dihydroxyazo-compounds

1989 ◽  
Vol 54 (5) ◽  
pp. 1219-1226 ◽  
Author(s):  
Enric Casassas ◽  
Miquel Esteban ◽  
Santiago Alier
Keyword(s):  
Carboxylic Acid ◽  
Reaction Mechanisms ◽  
Sulphonic Acid ◽  
Base Catalysis ◽  
Polarographic Study ◽  
Acid Base ◽  
Eriochrome Black T ◽  
Naphthoic Acid ◽  
Calcon Carboxylic Acid

The reduction of several o,o'-dihydroxyazo-compounds is studied by means of pulse polarographic techniques (DPP, NPP and RPP). The compounds studied are the following: 2-(2'-hydroxyphenylazo)-phenol (o,o'-dihydroxyazobenzene), 1-(2'-hydroxy-1'-naphthylazo)-2-naphthol-4-sulphonic acid (calcon or Eriochrome Blue Black R), 1-(2'-hydroxy-4'-sulpho-1'-naphthylazo)-2-hydroxy-3-naphthoic acid (calcon carboxylic acid), and 1-(1'-hydroxy-2'-naphthylazo)-6-nitro-2-naphthol-4-sulphonic acid (Eriochrome Black T). Correlations between Ip and Epand experimental variables (pH, T, conc.) and instrumental parameters (dropping time, t, and pulse magnitude, ΔE) are established. Reaction mechanisms formerly proposed are discussed on the basis of the new obtained results, and the ranges are defined where adsorption and/or acid-base catalysis are operative.

scholarly journals Crystal structures of two 6-(2-hydroxybenzoyl)-5H-thiazolo[3,2-a]pyrimidin-5-ones

2015 ◽  
Vol 71 (7) ◽  
pp. 766-771
Author(s):  
Ligia R. Gomes ◽  
John Nicolson Low ◽  
Fernando Cagide ◽  
Fernanda Borges
Keyword(s):  
Hydrogen Bond ◽  
Carboxylic Acid ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Dihedral Angles ◽  
Stacking Interactions ◽  
Mechanism Of Formation ◽  
Π Stacking ◽  
Heterocyclic Moiety

The title compounds, 6-(2-hydroxybenzyl)-5H-thiazolo[3,2-a]pyrimidin-5-one, C13H8N2O3S, (1), and 6-(2-hydroxybenzyl)-3-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one, C14H10N2O3S, (2), were synthesized when a chromone-3-carboxylic acid, activated with (benzotriazol-1-yloxy)tripyrrolidinylphosphonium hexafluoridophosphate (PyBOP), was reacted with a primary heteromamine. Instead of the expected amidation, the unusual title thiazolopyrimidine-5-one derivatives were obtained serendipitously and a mechanism of formation is proposed. Both compounds present an intramolecular O—H...O hydrogen bond, which generates anS(6) ring. The dihedral angles between the heterocyclic moiety and the 2-hydroxybenzoyl ring are 55.22 (5) and 46.83 (6)° for (1) and (2), respectively. In the crystals, the molecules are linked by weak C—H...O hydrogen bonds and π–π stacking interactions.

Mechanism of formation and 32P-postlabeling of DNA adducts derived from peroxidative activation of carcinogenic non-aminoazo dye 1-phenylazo-2-hydroxynaphthalene (Sudan I)

1990 ◽  
Vol 11 (10) ◽  
pp. 1843-1848 ◽  
Author(s):  
M. Stiborová ◽  
E. Frei ◽  
H.H. Schmeiser ◽  
J. Hradec
Keyword(s):  
Dna Adducts ◽  
Mechanism Of Formation ◽  
Sudan I

Exhaustive C-methylation of carboxylic acids by trimethylaluminium: A new route to t-butyl compounds

1974 ◽  
Vol 27 (8) ◽  
pp. 1665 ◽  
Author(s):  
A Meisters ◽  
T Mole
Keyword(s):  
Carboxylic Acid ◽  
Benzoic Acid ◽  
Carboxylic Acids ◽  
Cinnamic Acid ◽  
Benzoic Acids ◽  
Naphthoic Acid ◽  
Triphenylacetic Acid

Carboxylic acids are exhaustively C-methylated to t-butyl compounds by excess trimethylaluminium at c. 120�. Benzoic acid for example, gives t-butylbenzene. Similarly methylated are o-fluoro-, o-bromo-, and m-chloro-benzoic acids, 5-chloro-3-phenylsalicylic acid, 1-naphthoic acid, palmitic, oleic and undec-10-enoic acids. Adamantane-1-carboxylic acid gives mostly l-isopropenyladaman- tane, along with some 1-t-butyladamantane. Cinnamic acid gives mainly the allylically rearranged 2-methyl-4-phenylpent-2-ene. Triphenylacetic acid behaves atypically; 1,1,1-triphenylpropan-2-one and 3,3,3-triphenylpropyne result.

Cytochrome P-450 and Peroxidase Oxidize Detoxication Products of Carcinogenic Aristolochic Acids (Aristolactams) to Reactive Metabolites Binding to DNA in vitro

1995 ◽  
Vol 60 (12) ◽  
pp. 2189-2199 ◽  
Author(s):  
Marie Stiborová ◽  
Eva Frei ◽  
Heinz H. Schmeiser ◽  
Manfred Wiessler
Keyword(s):  
Dna Adducts ◽  
Microsomal Cytochrome ◽  
Aristolochic Acids ◽  
Nuclease P1 ◽  
Order Of Magnitude ◽  
Prostaglandin H ◽  
Cytochrome P 450

We report the analysis of DNA adducts formed from aristolactams I and II, which are the final metabolites derived from carcinogenic aristolochic acids in vivo, after their oxidation by microsomal cytochrome P-450 and horseradish peroxidase in vitro. DNA adducts were detected and quantified using the nuclease P1-enhanced variation of the 32P-postlabeling assay. Quantitative analysis revelead that the extent of modification of DNA by aristolactams activated by peroxidase was more than one order of magnitude higher than for activation by microsomal cytochrome P-450. Peroxidase catalyzes the formation of active oxygen in the presence of NADH, H2O2 and aristolactams. Aristolactams are also oxidized by mammalian peroxidase prostaglandin H synthase. The possible role of aristolactams in carcinogenesis induced by aristolochic acid is discussed.

scholarly journals Adenine versus guanine DNA adducts of aristolochic acids: role of the carcinogen–purine linkage in the differential global genomic repair propensity

2015 ◽  
Vol 43 (15) ◽  
pp. 7388-7397 ◽  
Author(s):  
Preetleen Kathuria ◽  
Purshotam Sharma ◽  
Stacey D. Wetmore
Keyword(s):  
Dna Adducts ◽  
Aristolochic Acids

THE SYNTHESIS OF POSSIBLE DEGRADATION PRODUCTS OF METATHEBAINONE. I.

1944 ◽  
Vol 22b (3) ◽  
pp. 56-65 ◽  
Author(s):  
H. L. Holmes ◽  
L. W. Trevoy
Keyword(s):  
Carboxylic Acid ◽  
Ethyl Ester ◽  
Degradation Products ◽  
Aldehyde Group ◽  
Carboxyl Group ◽  
Unsuccessful Attempt ◽  
Naphthoic Acid ◽  
Relationship Of ◽  
The Relationship ◽  
General Method

The method of Crowley and Robinson (5) for the synthesis of 6-methoxy-3,4-dihydro-2-naphthoic acid has been modified to provide an improved and general method for the synthesis of 3,4-dihydro-2-naphthoic acids. The 7-methoxy-3,4-dihydro-2-naphthoic acid and its ethyl ester have been shown to react with butadiene and 2,3-dimethylbutadiene to give 3-methoxy-5,8,9,10,13,14-hexahydrophenanthrene-14-carboxylic acid and its 6,7-dimethyl derivative. The relationship of these hydrophenanthrenes to possible degradation products of morphine and metathebainone has been discussed. An unsuccessful attempt was made to lengthen the C14-chain by converting the carboxyl group to an aldehyde group by the Rosenmund method followed by condensation with malonic acid. The projected conversion failed in the first stage.

125. 1 : 9-Benzanthrone-8-carboxylic acid and dibenzanthronedicarboxylic acid from 8-bromo-1-naphthoic acid

1935 ◽  
pp. 571 ◽  
Author(s):  
H. Gordon Rule ◽  
William Pursell ◽  
A. John G. Barnett
Keyword(s):  
Carboxylic Acid ◽  
Naphthoic Acid

Quantitation of DNA Adducts of Aristolochic Acids in Repair-Deficient Cells: A Mechanistic Study of the DNA Repair Mechanism

2020 ◽  
Vol 33 (6) ◽  
pp. 1323-1327 ◽  
Author(s):  
Chun-Kit Au ◽  
Chi-Kong Chan ◽  
Ka-Ki Tung ◽  
Jiayin Zhang ◽  
Wan Chan
Keyword(s):  
Dna Repair ◽  
Dna Adducts ◽  
Mechanistic Study ◽  
Repair Mechanism ◽  
Aristolochic Acids
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