18371-72-7Relevant articles and documents
Rational design 2-hydroxypropylphosphonium salts as cancer cell mitochondria-targeted vectors: Synthesis, structure, and biological properties
Amerhanova, Syumbelya K.,Dimukhametov, Mudaris N.,Gubaidullin, Aidar T.,Islamov, Daut R.,Litvinov, Igor A.,Lyubina, Anna P.,Mironov, Vladimir F.,Nemtarev, Andrey V.,Pashirova, Tatiana N.,Titov, Eugenii A.,Tsepaeva, Olga V.,Voloshina, Alexandra D.
, (2021/11/01)
It has been shown for a wide range of epoxy compounds that their interaction with triphenylphosphonium triflate occurs with a high chemoselectivity and leads to the formation of (2-hydroxypropyl)triphenylphosphonium triflates 3 substituted in the 3-position with an alkoxy, alkylcarboxyl group, or halogen, which were isolated in a high yield. Using the methodology for the disclosure of epichlorohydrin with alcohols in the presence of boron trifluoride ether-ate, followed by the substitution of iodine for chlorine and treatment with triphenylphosphine, 2-hydroxypropyltriphenylphosphonium iodides 4 were also obtained. The molecular and supramolec-ular structure of the obtained phosphonium salts was established, and their high antitumor activity was revealed in relation to duodenal adenocarcinoma. The formation of liposomal systems based on phosphonium salt 3 and L-α-phosphatidylcholine (PC) was employed for improving the bioavailabil-ity and reducing the toxicity. They were produced by the thin film rehydration method and exhibited cytotoxic properties. This rational design of phosphonium salts 3 and 4 has promising potential of new vectors for targeted delivery into mitochondria of tumor cells.
Preparation and properties of phosphate surfactants containing ether and hydroxy groups
Osanai, Shuichi,Yamada, Go,Hidano, Ruri,Beppu, Koji,Namiwa, Kimiyoshi
supporting information; experimental part, p. 41 - 49 (2011/12/05)
Phosphate surfactants containing ether and hydroxyl groups were prepared by a simple reaction between the corresponding epoxide and the diethyl phosphate. The relationships between the structure and colloidal properties were evaluated in terms of the critical micelle concentration (CMC), γCMC, foaming ability, and water absorbing and holding abilities. Based on these results, it was concluded that the ether and hydroxy groups synergistically worked together to decrease the CMC and increase the foaming ability. The degree of neutralization remarkably affected the colloidal properties. The highly neutralized states showed a more positive effect on water holding power but an opposite effect on the foaming ability. Copyright
The kinetics of chloromethyloxirane reaction with alcohols and their adducts in the presence of stannic chloride
Chlebicki,Pozniak
, p. 79 - 88 (2007/10/03)
Rate constants of the reaction of chloromethyloxirane (epichlorohydrin) with methyl, n-propyl, isopropyl, n-, sec-, tert-butyl, n-hexyl, n-octyl, and n-decyl alcohols in the presence of stannic chloride were studied at 30, 40, and 50°C. Reaction is not first order in respect to epichlorohydrine and is particularly fast at the beginning and its rate constants are proportional to the concentration of the catalyst. The rate constants increase in the homologous series of C1-C10 alcohols. The reaction rates of 2-chloromethyloxirane with 1-chloromethyl-2-alkoxyethanols are ca. 2.5-times larger than that with corresponding alcohols.