298-06-6Relevant academic research and scientific papers
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.
A convenient route to novel fluorinated 1, 2, 4, 3-triazaphospholo[1, 5-a]pyridines and pyrido[1, 2-b][1, 2, 4, 5]triazaphosphinines
Assiri, Mohammed A.,Abdel-Kariem, Somaia M.,Ali, Tarik E.,Yahia
, p. 240 - 253 (2018)
A simple synthetic approach to the construction of novel fluorinated 5-oxo(thioxo)-2-oxido(sulfido)-1, 2, 4, 3-triazaphospholo[1, 5-a]pyridines 2-14 and pyrido[1, 2-b][1, 2, 4, 5]triazaphosphinines 16, 19 and 22, was achieved. The method depends on the treatment of 1, 6-diamino-4-(4-fluorophenyl)-2-oxo-1, 2-dihydropyridine-3, 5-dicarbonitrile (1) with some different types of phosphorus reagents such as phosphorus acid, and their esters, phosphorus halides as well as phosphorus sulfides. Structures of all the synthesized 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).
Synthesis of novel 3-phenyl-2-oxido/sulfido-1,3,4,2-benzoxadiazaphosphepines
Ali, Tarik E.,Assiri, Mohammed A.,Yahia
, p. 1828 - 1837 (2018)
An efficient and facile synthetic approach towards a series of novel 3-phenyl-2-oxido/sulfido-2,3-dihydro-1,3,4,2-benzoxadiazaphosphepines 2–7 was described. The method depended on the cyclocondensation of equimolar ratios of salicylaldehyde phenylhydrazone (1) with different examples of phosphorus halides and phosphorus sulfides in toluene containing triethylamine as a catalyst. In the same manner, the fusion of salicylaldehyde phenylhydrazone (1) with triethyl phosphate in the presence of DBU afforded the 2-ethoxy-1,3,4,2-benzoxa-diazaphosphepine 8, while a fusion of compound 1 with diethyl phosphite and tris(2-chloroethyl)phosphite led to the formation of new examples of 1,2-benzoxaphospholes 9 and 10, respectively. Interestingly, the reaction of compound 1 with diethyl ethoxycarbonyl phosphonate in ethanol containing DBU as a catalyst furnished the chromeno[3,4-d][1,2,3]diazaphosphole derivative 12 as a regioselective product.
Synthesis and in vitro antimicrobial, antioxidant, and antiproliferative activities of some new pyrano[2,3-c]pyrazoles containing 1,2-azaphospholes, 1,3,2-diazaphosphinines and phosphonate moieties
Ali, Tarik E.,Assiri, Mohammed A.,El-Shaaer, Hafez M.,Abdel-Kariem, Somaia M.,Abdel-Monem, Wafaa R.,El-Edfawy, Somaya M.,Hassanin, Noha M.,Shati, Ali A.,Alfaifi, Mohammad Y.,Elbehairi, Serag Eldin I.
supporting information, p. 2478 - 2497 (2021/06/30)
New 1,2-azaphosphole, 1,3,2-diazaphosphinine, and phosphonate derivatives containing pyrano[2,3-c]pyrazole moiety were achieved. The synthetic pathways depended on the reaction of 6-amino-3-methyl-1,4-diphenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile with some phosphorus reagents such as diethyl phosphite, phosphorus sulfides, and phenyl phosphorus halides under different conditions. Compounds 6 and 7 recorded potent antibacterial and antifungal activities with lower toxicity, while compounds 4 and 6 displayed promising antioxidative properties. Further, compounds 4 and 9 exhibited potent cytotoxic effects against MCF-7, HepG-2, and HCT-116 cancer cells. The early apoptotic cell death was observed by the compounds in all types of the treated cells. Compounds 3, 5, 7, 10, and 14 recorded low to moderate percentages of necrosis and late apoptosis toward all treated cells.
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.
Green synthesis technology of O,O-diethyl thiophosphoryl chloride
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Paragraph 0029; 0030; 0031; 0036; 0037; 0038; 0043; 0044, (2019/03/06)
The invention provides a green synthesis technology of O,O-diethyl thiophosphoryl chloride and relates to the field of chemical synthesis. The green synthesis technology comprises the following steps:taking O,O-diethyl dithiophosphate to react with chlorine gas at low temperature, so as to obtain a crude product of the O,O-diethyl thiophosphoryl chloride; then transferring the crude product to react at high temperature; enabling the residual O,O-diethyl dithiophosphate to further completely react with the chlorine gas. Meanwhile, in a high-temperature reaction process, a polymeric compound isprevented from being generated when a compound catalyst is used and sulfur monochloride impurities are completely removed through reaction, so that a byproduct sulfur has a crystalline state and a product more easily separated and purified. Moreover, HCl and sulfur-containing odorous gas are pumped away through applying negative pressure and the tail gas is absorbed to prevent air pollution. In awhole reaction process, technological water does not need to be added, so that wastewater is not generated and the treatment cost of sulfur-containing and phosphorus-containing wastewater is reduced.The technology has the advantages of simplicity in operation, easiness for obtaining raw materials, moderate reaction conditions, small pollution and environment friendliness.
Facile synthesis of novel 6-methyl-5-phenyl-2-sulfido-1,2,3,5-tetrahydro-4H[1,2] oxazolo[4′,5′:5,6]pyrano[2,3-d][1,3,2]diazaphosphinines
Ali, Tarik E.,Assiri, Mohamed A.,Abdel-Kariem, Somaia M.,Yahia, Ibrahim S.
, p. 472 - 482 (2018/04/02)
A number of 6-methyl-5-phenyl-2-sulfido-1,2,3,5-tetrahydro-4H[1,2]oxazolo[4′,5′: 5,6]pyrano[2,3-d][1,3,2]diazaphosphinines 4–11 were synthesized via an interaction of tetraphosphorus decasulfide and Lawesson’s reagent under different conditions with 6-amino-3-methyl-4-phenyl-4H-pyrano[3,2-d][1,2]oxazole-5-carbonitrile (3). The reaction mechanisms for these products were discussed. Structures of the newly synthesized products were established on the basis of elemental analysis and spectral data.
Synthesis, spectral characterization and antibacterial activity of O, O’-dialkyl and alkylene dithiophosphatogold (III)dichloride; crystal structure of [S2POCMe2CMe2O]AuCl2
Elkhaldy, Adnan A. S.,Gaikwad, Dnyaneshwar,Staples, Richard J.,Janen, Afef,Boni, Yannic
, p. 871 - 876 (2019/02/05)
O, O’-Dialkyl and alkylene dithiophosphatogold (III)dichloride complexes of the type [(RO)2PS2]AuCl2 and [S2POGO]AuCl2, where R = Et, nPr, iPr, iBu, Ph, cyclohexyl and cyclopentyl, where G = CMe2CMe2-, have been synthesized in 80-90% yields by reaction of the corresponding acid or sodium salts of the appropriate dithiophosphoric acids in 1:1 ratio with gold (III) chloride in dry dichloromethane at room temperature. The compounds have been characterized by elemental analyses, IR and (1H, l3C, and 31P) NMR. The crystal structure of [S2POCMe2CMe2O]AuCl2, was determined. These new complexes have shown their growth inhibiting potential against various bacterial strains with moderate to good activity.
Free-metal dicarboxylic acid derivatives and antiwear additives and lubricant compositions comprising the same
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Paragraph 0264; 0265, (2018/02/27)
The present invention relates to heavy-metal-free dicarboxylic acid derivatives and to a wear-resistant and lubricant composition comprising the same. The lubricant composition comprising a dicarboxylic acid derivative compound according to the present invention has superior abrasion resistance performance to abrasion resistance performance of a conventional lubricant oil composition, and even when used at a lower content than the conventional lubricant oil composition, more excellent effects are exhibited, wherein heavy metals are not used to be environment-friendly, thereby being usefully used as engine oil, lubricating oil for a transmission, gear-oil, turbine oil, operation oil, refrigerator oil, compressor oil, vacuum pump oil, bearing oil, sliding surface oil, crude oil, metal cutting oil, plastic working oil, heat-treated oil, lubricating oil or processed oil additives.COPYRIGHT KIPO 2017
