4016-11-9Relevant academic research and scientific papers
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.
Diastereoselective Desymmetrization of p-Quinamines through Regioselective Ring Opening of Epoxides and Aziridines
Jadhav, Sandip B.,Chegondi, Rambabu
supporting information, p. 10115 - 10119 (2019/12/24)
A highly diastereoselective desymmetrization of p-quinamines via regioselective ring opening of epoxides and aziridines under mild conditions has been developed. A chairlike six-membered transition state with minimized 1,3-diaxial interactions explains the relative stereoselectivity of the cyclization reaction. This transition-metal free [3 + 3] annulation reaction provides rapid access to fused bicyclic morpholines and piperazines with a tetrasubstituted carbon center in high yields. In addition, it also allows the synthesis of enantioenriched products by using easily accessible chiral nonracemic epoxides and aziridines.
hybrid-fluorinated non-ionic surfactant with short perfluoroalkyl chains and preparation method thereof
-
Paragraph 0178-0181; 0189-0192, (2018/07/03)
The present invention relates to a hybrid fluorine-based nonionic surfactant containing a short fluorinated alkyl group, and a preparing method thereof, and more particularly, to a hybrid fluorine-based nonionic surfactant having one low fluorinated alkyl group and one hydrocarbon group, and a preparing method thereof. According to the present invention, the hybrid fluorine-based nonionic surfactant realizes a low surface tension and CMC even though a short fluorinated alkyl group is included in one molecule, and has high solubility in water and excellent emulsification stability, and thus has excellent physical properties as a surfactant. In addition, the hybrid fluorine-based nonionic surfactant is less harmful to the human body and the environment compared to a conventional surfactant due to low fluorinated alkyl group, and requires low manufacturing costs and thus can be beneficially used as an eco-friendly and economical fluorine-based nonionic surfactant having competitiveness in terms of price. In particular, the hybrid fluorine-based nonionic surfactant of the present invention can be beneficially used as a surfactant replacing a conventional fluorine-based nonionic surfactant containing a long perfluorinated alkyl group such as PFOA or PFOS known to be harmful to the environment and the human body.COPYRIGHT KIPO 2018
Mechanism of preferential enrichment, an unusual enantiomeric resolution phenomenon caused by polymorphic transition during crystallization of mixed crystals composed of two enantiomers
Tamura, Rui,Fujimoto, Daisuke,Lepp, Zsolt,Misaki, Kentaro,Miura, Hideyuki,Takahashi, Hiroki,Ushio, Takanori,Nakai, Tadashi,Hirotsu, Ken
, p. 13139 - 13153 (2007/10/03)
The mechanism of Preferential Enrichment, an unusual enantiomeric resolution phenomenon observed upon recrystallization of a series of racemic crystals which are classified as a racemic mixed crystal with fairly ordered arrangement of the two enantiomers, has been studied. On the basis of the existence of polymorphs and the occurrence of the resulting polymorphic transition during crystallization from solution, the mechanism has been accounted for in terms of (1) a preferential homochiral molecular association to form one-dimensional chain structures in the supersaturated solution of the racemate or nonracemic sample with a low ee value, (2) a kinetic formation of a metastable crystalline phase retaining the homochiral chain structures in a process of nucleation, (3) a polymorphic transition from the metastable phase to a stable one followed by enantioselective liberation of the excess R (or S) enantiomers from the transformed crystal into solution at the beginning of crystal growth to result in a slight enrichment (up to 10% ee) of the opposite S (or R) enantiomer in the deposited crystals, together with an enantiomeric enrichment of the R (or S) enantiomer in the mother liquor, and (4) a chiral discrimination by the once formed S (or R)-rich stable crystalline phase in a process of the subsequent crystal growth, leading to a considerable enantiomeric enrichment of the R (or S) enantiomer up to 100% ee in the mother liquor. The processes (3) and (4) are considered to be directly responsible for an enrichment of one enantiomer in the mother liquor. The association mode of the two enantiomers in solution has been investigated by means of (i) the solubility measurement and (ii) the number-averaged molecular weight measurement in solution by vapor pressure osmometry, together with (iii) the molecular dynamics simulation of oligomer models. The polymorphic transition during crystallization has been observed visually and by means of the in situ FTIR technique and DSC measurement. Both metastable and stable crystals have been obtained, and their crystal structures have been elucidated by X-ray crystallographic analysis of their single crystals.
LE CHLOROALLYLLITHIUM COMME SYNTHON DE CHLOROALLYLATION OU COMME EQUIVALENT DU VINYLCARBENE: SYNTHESE REGIOSELECTIVE D'ALCOOLS γ-ETHYLENIQUES β-CHLORES ET DE VINYL-2 OXETANES A PARTIR D'EPOXYDES
Ongoka, P.,Mauze, B.,Miginiac, L.
, p. 139 - 148 (2007/10/02)
Chloroallyllithium reacts regioselectively with various epoxides in a "one-pot" reaction to produce either γ-ethylenic β-chloro alcohols or 2-vinyl oxetanes, depending on the experimental conditions used.
An Electron Spin Resonance Study of 3-Oxypropenoyl Radicals derived from Glycidols
Davies, Alwyn G.,Hawari, Jalal A.-A.,Muggleton, Brenda,Tse, Man-Wing
, p. 1132 - 1137 (2007/10/02)
Glycidols with blocked OH groups (A; M = alkyl or trialkylsilyl) react with t-butoxyl radicals to show the e.s.r. spectra of the corresponding 3-oxypropenoyl radicals (D), and 24 examples of these acyl radicals are reported.The reaction is thought to proceed through the formation of the allyloxyl radicals (B), which, in part, are converted into the aldehyde (C) which is very reactive towards loss of hydrogen to give the acyl radical (D).Glycidyl pivalate (A; M = COCMe3) reacts cleanly in this way, but glycidyl acetate (E; R = Me) also undergoes intramolecular 1,5-transfer of the acyl group to show the spectrum of the enoxyl radical (F).Glycidyl propionate and butyrate do not undergo this acyl transfer, but show the spectra of the radicals and (R' = Me or Et).
