... While oxidative metabolism of low molecular weight primary alcohols is generally ... catalyzed by alcohol dehydrogenase, propargyl alcohol is a relatively poor substrate for this enzyme ... The catalase alternative pathway /was studied/. Bovine liver catalase was used, to measure the rate of oxidative bioactivation of propargyl alcohol to 2-propyn-l-al ... /It was/ found the rate to be higher than predicted ... and hypothesized that the oxidative biotransformation of propargyl alcohol to the more reactive alpha, beta-unsaturated aldehyde by liver catalase might be the initial step in propargyl alcohol induced liver injury.
Chromatographic analysis indicated that propargyl alcohol is extensively metabolized and one metabolite was identified as a glutathione conjugate. It was assumed that there are multiple glutathione conjugates across the triple bond ...
... Inactivation of catalase in isolated hepatocytes only partially inhibited the toxicity of propargyl alcohol /was shown/ ... Propargyl alcohol-induced cytotoxicity, rapid GSH depletion and reactive oxygen species (ROS) formation involves metabolic activation by cytochrome P450 rather than catalase or alcohol dehydrogenase /was demonstrated/. Using specific induction and depletion ... /it was shown/ that CYP 2E1 was the enzyme responsible for activation of propargyl alcohol to its aldehyde, 2-propyn-I-al ... /A model was proposed that/ propargyl alcohol is oxidized primarily by CYP 2E1, with a minor contribution by alcohol dehydrogenase, to 2-propyn-l-al. The aldehyde is a chemically active species that can attack vital cellular macromolecules but reacts preferentially with glutathione to form conjugates that undergo urinary excretion. An alternative pathway for the aldehyde is further enzymatic oxidation via aldehyde dehydrogenase to propiolic acid, which could be further, oxidized, conjugated and excreted, or be converted back into the aldehyde ... Depletion of glutathione and formation of ROS (reactive oxygen species), which lends support to the proposed mechanism, /was demonstrated/ ...
Male Sprague-Dawley rats were dosed orally with 40 mg/kg mixture of (1,2,3-(13)C)propargyl alcohol and (1,2-(14)C)propargyl alcohol. Approximately 60% of the dose was excreted in the urine by 96 hr. Major metabolites were identified in the urine by 1- and 2-D NMR and confirmed by isolation and purification of the individual metabolites followed by (13)C FT-NMR and mass spectometry. The proposed pathway involves oxidation of propargyl alcohol to 2-propynoic acid and glutathione conjugation, the first example of multiple glutathione additions to a triple bond. The following final products were identified: 3-((2-(acetylamino)-2-carboxyethyl)thio)-2-propenoic acid, S-S-(3-hydroxypropylidene)-bis(N-acetylcysteine), and 3-((2-(acetylamino)-2-carboxyethyl)-sulfinyl)-3-((2-(acetylamino)-2-carboxyethyl)thio)1-propanol.
来源:Hazardous Substances Data Bank (HSDB)
毒理性
暴露途径
该物质可以通过吸入其蒸汽、通过皮肤接触以及摄入进入人体。
The substance can be absorbed into the body by inhalation of its vapour, through the skin and by ingestion.
来源:ILO-WHO International Chemical Safety Cards (ICSCs)
Propargyl alcohol is quickly distributed and excreted following an iv dose. The majority of the radioactivity ((14)C-labeled test material) was excreted in the urine and as carbon dioxide in the breath of both rats and mice. Oral dosing resulted in a similar rapid (but slower than after iv dosing) excretion pattern, with the bulk of radioactivity being excreted in the urine and exhaled carbon dioxide. Dermal absorption was low due to the volatility of propargyl alcohol. Inhalation exposure resulted in 55 to 63% absorption of inhaled propargyl alcohol at 1 or 10 ppm and only 23 to 33% absorption at 100 ppm. Both species eliminated the majority of the inhaled dose in urine.
来源:Hazardous Substances Data Bank (HSDB)
吸收、分配和排泄
丙烯醇可以通过吸入其蒸汽、透过皮肤和摄入的方式被人体吸收。
... /Propargyl alcohol/ can be absorbed into the body by inhalation of its vapor, through the skin and by ingestion.
Male Sprague-Dawley rats were dosed orally with 40 mg/kg mixture of (1,2,3-(13)C)propargyl alcohol and (1,2-(14)C)propargyl alcohol. Approximately 60% of the dose was excreted in the urine by 96 hr ...
Some Aspects of the Azide-Alkyne 1,3-Dipolar Cycloaddition Reaction
作者：N. T. Pokhodylo、M. A. Tupychak、O. Ya. Shyyka、M. D. Obushak
DOI：10.1134/s1070428019090082
日期：2019.9
Some peculiar features of two most commonly used catalytic systems (Cul and CuSOVsodium ascorbate) controlling the regioselectivity of 1,3-dipolar cycloaddition of azides to terminal alkynes have been studied. Their potentialities, main disadvantages, and limitations have been demonstrated by a number of examples, including reactions of low-molecular-weight azides and alkynes containing heterocyclic
coupling of ω‐allenyl‐substituted carboxylicacids. The use of a modified diop ligand, chiral DTBM‐diop, led to high enantioselectivity (up to 93 % ee). The reaction tolerated a large variety of functionalities, including α,β‐unsaturated carboxylicacids and depsipeptides, and provided the desired macrocycles with very high enantio‐ and diastereoselectivity.
LC50 values of 7.744, 5.634, 6.809, 7.939 and 52.234 μM, respectively. Furthermore, QSAR analysis showed that the molecular shape, size, connectivity degree and electronic distribution of avermectin analogues had substantial effects on insecticidal potency. These preliminary results provided useful insight in guiding further modifications of avermectin in the development of potential new insecticides.
作者：L. Yu. Ukhin、K. Yu. Suponitsky、L. V. Belousova、Zh. I. Orlova
DOI：10.1007/s11172-009-0347-1
日期：2009.12
A new synthesis of phthalimidines is described. 3-Acyloxy-2-aryl- and 2-acylamino-3-acyloxyphthalimidines were prepared by the reaction of 3-arylaminophthalides or o-formylbenzoic acid acylhydrazones with acetic or propionic anhydrides. Their reactions with O-, N-, S-, and C-nucleophiles were studied. The structure of 2-acetyl(cyanoacetyl)amino-3-acetoxyindolin-1-one was confirmed by X-ray diffraction
描述了邻苯二甲酰亚胺的新合成。3-酰氧基-2-芳基-和2-酰氨基-3-酰氧基邻苯二甲酰亚胺通过3-芳基氨基苯酞或邻甲酰基苯甲酸酰腙与乙酸或丙酸酐反应制备。研究了它们与 O-、N-、S-和 C-亲核试剂的反应。2-乙酰（氰基乙酰）氨基-3-乙酰氧基吲哚-1-one 的结构通过 X 射线衍射分析得到证实。
