298-06-6Relevant articles and documents
Unusual behavior of 3-(dimethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-one towards some phosphorus reagents: Synthesis of novel diethyl 2-phosphonochromone, diethyl 3-phosphonopyrone and 1,3,2-oxathiaphosphinines
Ali, Tarik E.,Assiri, Mohammed A.,Yahia, Ibrahim S.,Zahran, Heba Y.
, p. 550 - 557 (2019)
The chemical reactivity of 3-(dimethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-one (1) towards some phosphorus reagents was studied. The enaminone 1 was cyclized into diethyl 2-phosphonochromone 2 via its treatment with diethyl phosphite in basic medium. However, its reaction with triethoxy phosphonoacetate gave the substituted pyrone phosphonate 3. In addition, two novel examples of 4-(dimethylamino)-6-(2-hydroxyphenyl)-2-sulfido-4H-1,3,2-oxathia-phosphinines 6 and 7 were obtained from treatment of enaminone 1 with O,O-diethyl dithiophosphoric acid and Lawesson’s reagent. When enaminone 1 was also treated with phosphorus decasulfide, it was turned into 4H-thiochromene-4-thione while its treatment with phosphorus tribromide, phosphorus oxychloride, or phenylphosphonic dichloride, 4H-4-oxo-chromene was isolated in all cases. The possible reaction mechanisms of the formation of these products were discussed. The structures of newly isolated products were established by elemental analysis and spectral tools.
Synthesis and cytotoxicity evaluation of some novel chromone annulated phosphorus heterocycles
Ali, Tarik E.,Ibrahim, Magdy A.,El-Edfawy, Somaya M.
, p. 819 - 826 (2017)
Novel chromono[2,3-e][1,2,4,3]triazaphosphepines 3?7, chromono[2,3-d][1,3,2]diazaphosphinine 8, chro-monyl α-hydrazinophosphonic acid 10, chromono[3,2-d][1,2]azaphosphole 11 and diethyl N-chromony-lphosphonoacetamide 12 were synthesized from treatment of 2-amino-3-[(2-phenylhydrazinylidene)methyl]chromone (2) with some phosphorus reagents such as phosphorus halides, phosphorus sulfides, and phosphonic acid and its diesters, in dry dioxane. The cytotoxic effects of the synthesized compounds were evaluated in vitro in relation to hepatocellular Hep-G2, breast MCF-7 and colon HCT-116 human cancer cell lines, using a crystal violet viability assay. Compounds 6, 7, 8, and 10 had significant cytotoxic effects against the three cancer cell lines. Their IC50 values ranged between 1.56 and 12.4?μg/mL in comparison to doxorubicin (IC50 = 0.426-0.469?μg/mL).
Pischtschimuka
, (1925)
Characterization of Dialkyldithiophosphates as Slow Hydrogen Sulfide Releasing Chemicals and Their Effect on the Growth of Maize
Carter, Justin M.,Brown, Eric M.,Irish, Erin E.,Bowden, Ned B.
, (2019/11/03)
Hydrogen sulfide is a key gasotransmitter for plants and has been shown to greatly increase their growth and survival in the presence of environmental stressors. Current methods for slowly releasing hydrogen sulfide use chemicals, such as GYY-4137, but these result in the release of chemicals not found in the environment, and chemicals used may lack structures that can be readily tuned to affect the rate of release of hydrogen sulfide. In this article, we describe the synthesis and slow release of hydrogen sulfide from dialkyldithiophosphates, which are a new set of hydrogen sulfide releasing chemicals that can be used in agriculture. The rates of hydrolysis of dibutyldithiophosphate and GYY-4137 were measured in water at 85 °C and compared with each other to investigate their differences. GYY-4137 is widely used as a chemical that slowly releases H2S, but its rate of release was not previously quantified. The release of hydrogen sulfide in water at room temperature was measured for a series of dialkyldithiophosphates using a hydrogen sulfide electrode. It was shown that the structure of the dialkyldithiophosphate affected the amount of hydrogen sulfide released. The final degradation products of dibutyldithiophosphate were shown to be phosphoric acid and butanol, which are chemicals found in the environment. This result was notable because it demonstrated that dialkyldithiophosphates degrade to safe, natural chemicals that will not pollute the environment. To demonstrate that dialkyldithiophosphates have potential applications in agriculture, maize was grown for 4.5 weeks after exposure to 1-200 mg of dibutyldithiophosphate, and the weight of corn plants increased by up to 39% at low loadings of dibutyldithiophosphate.
