Chemical synthesis of the 17-propanamide derivatives of stereoisomeric Δ14-17α- and 17β-estradiols: potential 17β-hydroxysteroid dehydrogenase inhibitors.


:The 17-propanamide derivatives of diastereomeric Δ(14)-17α- and 17β-estradiols, the potential candidates of a 17β-hydroxysteroid dehydrogenase (17β-HSD) inhibitor, were synthesized in 11 steps from estrone. The principal reactions employed involved in (1) conversion of estrone to the corresponding Δ(14)-estrone, (2) Grignard reaction of Δ(14)-estrone with allylmagnesium bromide followed by regioselective hydroboration of the resulting stereoisomeric 17ξ-allyl-Δ(14)-17ξ-ols with 9-borabicyclo[3.3.1]nonane (9-BBN), and (3) direct amidation of the 17ξ-O-/17ξ-C-spiro-γ-lactones with NH(3) under positive pressure of H(2).


Chem Phys Lipids


Iida T,Ogawa S,Tamegai H,Adachi Y,Saito H,Ikegawa S,Konishi H,Takagi A,Matsuzaki T




Has Abstract


2011-02-01 00:00:00














  • Interaction of the interdigitated DPPG or DPPG/DMPC bilayer with human erythrocyte band 3: differential scanning calorimetry and fluorescence studies.

    abstract::Human erythrocyte band 3 reconstituted into phospholipid vesicles has been used for studying the interaction of interdigitated lipid bilayer with an integral membrane protein. The interdigitated gel phase in DPPG/band 3 or DPPG/DMPC/band 3 systems was induced with polymyxin B (PMB) or Tris+. The phase transitions of t...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Wang PY,Lu JZ,Chen JW,Hwang F

    更新日期:1994-03-01 00:00:00

  • Measurement of phospholipase A2 and 1-alkylglycerophosphocholine acetyltransferase activities in stimulated alveolar macrophages by HPLC analysis of NBD-labeled ether lipids.

    abstract::The importance of phospholipases in cellular signaling and 1-alkylglycerophosphocholine acetyltransferase in the formation of platelet-activating factor (PAF) has stimulated demand for methods to measure these enzyme activities in inflammatory cells. Most of the assays currently used rely on radiolabeled substrates. W...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Kleuser B,Meister A,Sternfeld L,Gercken G

    更新日期:1996-01-25 00:00:00

  • Membrane specificity of non-monotonic trends in cation-mediated injury to rapidly frozen phospholipid vesicles.

    abstract::Phospholipid vesicles like erythrocyte ghosts [1] have been shown to display trends in freeze-thaw injury with Group I ions which are non-monotonic in nature. That is to say, the relative extent of injury with such ions, measured as calcein release, does not follow a lyotropic series related solely to the hydrated ion...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Brearley CA,Hodges NA,Oliff CJ

    更新日期:1991-09-01 00:00:00

  • Antioxidant activity of quercetin and myricetin in liposomes.

    abstract::The antioxidant activity during storage at 30 degrees C of quercetin, myricetin and alpha-tocopherol in small unilamellar liposomes has been investigated. Myricetin was more effective than alpha-tocopherol as an antioxidant in liposomes under all conditions studied. At pH 5.4 with a concentration of 10(-2) mol/mol pho...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Gordon MH,Roedig-Penman A

    更新日期:1998-12-01 00:00:00

  • Infrared and time-resolved fluorescence spectroscopic studies of the polymorphic phase behavior of phosphatidylethanolamine/diacylglycerol lipid mixtures.

    abstract::Fourier transform infrared (FTIR) and time-resolved fluorescence spectroscopy have been employed to examine the structural dynamics of lipid fatty acyl chains and lipid/water interfacial region of a binary lipid mixture containing unsaturated phosphatidylethanolamine (PE) and diacylglycerol (DG). Infrared vibrational ...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Chen SY,Cheng KH

    更新日期:1990-12-01 00:00:00

  • Calcium-induced aggregation of phosphatidylcholine vesicles containing free oleic acid.

    abstract::Small unilamellar vesicles (SUV) formed by egg yolk phosphatidylcholine (PC) and free oleic acid (OA) undergo aggregation induced by Ca2+ at pH greater than 7.0. The rate of the process, as monitored by turbidity changes, presents a linear dependence on phospholipid concentration and a hyperbolic dependence on Ca2+ co...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Ortiz A,Gomez-Fernandez JC

    更新日期:1988-04-01 00:00:00

  • Development of pH-sensitive self-nanoemulsifying drug delivery systems for acid-labile lipophilic drugs.

    abstract::Oral administration is the most convenient way of all the drug delivery routes. Orally administered bioactive compounds must resist the harsh acidic fluids or enzyme digestion in stomach, to reach their absorbed destination in small intestine. This is the case for silibinin, a drug used to protect liver cells against ...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Zhao T,Maniglio D,Chen J,Chen B,Migliaresi C

    更新日期:2016-03-01 00:00:00

  • Molecular interactions of active constituents of essential oils in zwitterionic lipid bilayers.

    abstract::Eugenol and its related compounds are major active constituents of essential oils and have been extensively used as food flavoring agents with significant lipid peroxidation inhibition activity, highlighting the importance of understanding detailed molecular mechanisms behind their interactions with lipid bilayer. For...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Saha S,Verma RJ

    更新日期:2018-07-01 00:00:00

  • Diffusion of hydrophilic probes in bicontinuous lipidic cubic phase.

    abstract::The lipidic cubic phase was prepared by mixing monoolein (monooleoyl-rac-glycerol, MO) with water in 64:36% ratio and applied to the solid support-glassy carbon or platinum electrodes. Highly viscous, homogeneous and transparent cubic phase film remained stable and firmly attached to the electrode surface. In order to...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Rowiński P,Korytkowska A,Bilewicz R

    更新日期:2003-07-01 00:00:00

  • pH responsive delivery of lumefantrine with calcium phosphate nanoparticles loaded lipidic cubosomes for the site specific treatment of lung cancer.

    abstract::The present work aim to develop pH responsive nanosystem comprising lumefantrine with calcium phosphate nanoparticles loaded lipidic cubosomes for the effective treatment of lung cancer. FTIR results showed that, compatibility nature of selected excipients for the synthesis of LF-CaP-Cs. The XRD results showed develop...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Sethuraman V,Janakiraman K,Krishnaswami V,Natesan S,Kandasamy R

    更新日期:2019-11-01 00:00:00

  • Poly (vinyl pyrrolidone)-lipid based hybrid nanoparticles for anti viral drug delivery.

    abstract::Zidovudine (AZT) is an antiviral drug with moderate solubility in water. It has limited application due to its short half life in vivo and consequent requirement for frequent administrations. To solve this problem, zidovudine loaded polyvinylpyrrolidone (PVP)/stearic acid (SA)-polyethylene glycol (PEG) nanoparticles (...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Joshy KS,Snigdha S,Anne G,Nandakumar K,Laly A P,Sabu T

    更新日期:2018-01-01 00:00:00

  • Interaction of photosensitizers with liposomes containing unsaturated lipid.

    abstract::Small unilamellar liposomes were made of dipalmitoyl-phosphatidylcholine and dioleoyl-phosphatidylcholine, and photosensitized by a symmetrically or an asymmetrically substituted glycosilated tetraphenyl-porphyrin derivative. As differential scanning calorimetry and electron paramagnetic resonance spectroscopy (EPR) r...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Voszka I,Budai M,Szabó Z,Maillard P,Csík G,Gróf P

    更新日期:2007-02-01 00:00:00

  • Diffusion of hydrogen peroxide across DPPC large unilamellar liposomes.

    abstract::The decomposition of hydrogen peroxide catalyzed by catalase entrapped in the pool of dipalmitoylphosphatidyl choline unilamellar liposomes has been studied. The rate of the process was evaluated by following the production of oxygen as a function of time. Under the experimental conditions employed the rate of oxygen ...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Abuin E,Lissi E,Ahumada M

    更新日期:2012-09-01 00:00:00

  • A second generation global analysis program for the recovery of complex inhomogeneous fluorescence decay kinetics.

    abstract::A fluorescence spectroscopy global data analysis environment is described. Within this analysis environment, multidimensional fluorescence decay data (time and frequency domains) can be analyzed in terms of a wide variety of photophysical models. A generalized compartmental analysis structure is utilized, where one ca...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Beechem JM

    更新日期:1989-06-01 00:00:00

  • In vitro determination of the solubility limit of cholesterol in phospholipid bilayers.

    abstract::Cholesterol has limited solubility in phospholipid bilayers. The solubility limit is strongly dependent on the nature of the lipid with which the cholesterol is mixed while properties of the crystals formed can be modified by phospholipid-cholesterol interactions. In this review we summarize the various methods that h...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章,评审


    authors: Epand RM,Bach D,Wachtel E

    更新日期:2016-09-01 00:00:00

  • Liposome-cell interactions: in vitro discrimination of uptake mechanism and in vivo targeting strategies to mononuclear phagocytes.

    abstract::The interactions of liposomes with cells have been extensively studied to determine their potential use as vehicles for the delivery of drugs in vivo. Since intravenously administered liposomes are, for the most part, cleared by cells of the reticuloendothelial system (RES), considerable effort has been made to take a...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Schroit AJ,Madsen J,Nayar R

    更新日期:1986-06-01 00:00:00

  • Polyprenyl phosphates: synthesis and structure-activity relationship for a biosynthetic system of Salmonella anatum O-specific polysaccharide.

    abstract::A series of polyprenyl phosphates with modified structure of polyprenyl residue was prepared through phosphorylation of polyprenyl trichloroacetimidates with phosphoric acid. Interaction of polyprenols with tetra-n-butylammonium dihydrogen phosphate and trichloroacetonitrile was found to represent a very efficient, si...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Danilov LL,Druzhinina TN,Kalinchuk NA,Maltsev SD,Shibaev VN

    更新日期:1989-11-01 00:00:00

  • Structural studies on branched fucosphingolipids of hog gastric mucosa.

    abstract::A structural studies have been performed on new complex glycolipids extracted from hog gastric mucosa by 0.4 M sodium acetate in methanol-chloroform-water, and which were purified to homogeneity by DEAE-Sephadex and Florisil column chromatography and by preparative thin-layer chromatography in three solvent systems. F...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Slomiany BL,Slomiany A

    更新日期:1977-09-01 00:00:00

  • Influence of temperature on dynamic surface properties of spread DPPC monolayers in a broad range of surface pressures.

    abstract::This work is focused on the study of the dynamic surface properties of spread monolayers of 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC), which is the main component of the pulmonary surfactant (PS), in the region of high surface pressures and at different temperatures. The increase of temperature from 25 to 35 ...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Bykov AG,Guzmán E,Rubio RG,Krycki MM,Milyaeva OY,Noskov BA

    更新日期:2019-12-01 00:00:00

  • Lipid transfer proteins and the tuning of compartmental identity in the Golgi apparatus.

    abstract::The Golgi complex constitutes a central way station of the eukaryotic endomembrane system, an intricate network of organelles engaged in control of membrane trafficking and the processing of various cellular components. Previous ideas of compartmental stability within this network are gradually being reshaped by conce...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章,评审


    authors: McDermott MI,Mousley CJ

    更新日期:2016-10-01 00:00:00

  • Lipid polymorphism and the roles of lipids in membranes.

    abstract::The reasons for lipid diversity in membranes are not understood. Here we review evidence supporting the proposal that factors related to the polymorphic capabilities of lipids provide a rationale for lipid diversity. In particular, the ability of lipids to adopt different polymorphic phases appears to be related to a ...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Cullis PR,Hope MJ,Tilcock CP

    更新日期:1986-06-01 00:00:00

  • Self-assembled systems based on novel hydroxyethylated imidazolium-containing amphiphiles: Interaction with DNA decamer, protein and lipid.

    abstract::The study on aggregation capacity of novel imidazolium-containing amphiphiles of 1-(2-hydroxyethyl)alkylimidazolium bromide series and their interaction with bio-objects (DNA decamer, bovine serum albumin, phospholipid) was performed. It was revealed that introduction of hydroxyethyl moiety into the surfactant molecul...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Kuznetsova DA,Gabdrakhmanov DR,Lukashenko SS,Voloshina AD,Sapunova AS,Kashapov RR,Zakharova LY

    更新日期:2019-09-01 00:00:00

  • Chemical stability of liposomes: implications for their physical stability.

    abstract::In the first part of this article, chemical and physical stability of aqueous liposome dispersions have been addressed. Chemical stability of phospholipids has been considered in two parts: oxidation and hydrolysis. Major attention has been paid to hydrolysis kinetics of phospholipids as a function of pH, temperature,...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章,评审


    authors: Grit M,Crommelin DJ

    更新日期:1993-09-01 00:00:00

  • Carbohydrate liquid crystals: synthesis and characterisation of the methyl-6-O-(n-acyl)-α-D-glucopyranosides.

    abstract::Seven members of the methyl-6-O-(n-acyl)-α-D-glucopyranosides have been synthesised and their transitional properties determined. The undecanoyl and octadecanoyl members do not exhibit liquid crystallinity while the members having chain lengths between dodecanoyl and hexadecanoyl exhibit a monotropic smectic A phase. ...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Cook AG,Wardell JL,Imrie CT

    更新日期:2011-02-01 00:00:00

  • Rapid tin-mediated access to a lysophosphatidylethanolamine (LPE) library: Application to positional LC/MS analysis for hepatic LPEs in non-alcoholic steatohepatitis model mice.

    abstract::Even though lysophospholipids have attracted much interest in recent years on account of their unique bioactivity, research related to lysophospholipids is usually hampered by problems associated with standard sample preparation and discrimination of regioisomers. Herein, we demonstrate a quick tin-chemistry-based syn...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Furukawa T,Fuda H,Miyanaga S,Watanabe C,Chiba H,Hui SP

    更新日期:2016-10-01 00:00:00

  • Sphingomyelin ability to act as chiral selector using nanodisc electrokinetic chromatography.

    abstract::Understanding how stereochemistry affects interactions with cell membranes is important for effective drug development. Chirality has been shown to greatly effect pharmaceutical distribution and metabolism within the cell. However it has been thought that interactions with, and passive diffusion through, the membrane ...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Penny WM,Palmer CP

    更新日期:2018-08-01 00:00:00

  • Oxidative modification of skin lipids by cold atmospheric plasma (CAP): A standardizable approach using RP-LC/MS2 and DI-ESI/MS2.

    abstract::Cold atmospheric plasma (CAP) is an emerging source for the locally defined delivery of reactive species, and its clinical potential has been identified in the control of inflammatory processes, such as acute and chronic wounds, or cancerous lesions. Lipids, due to their localization and chemical structure as ideal ta...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Striesow J,Lackmann JW,Ni Z,Wenske S,Weltmann KD,Fedorova M,von Woedtke T,Wende K

    更新日期:2020-01-01 00:00:00

  • Further studies on the inhibition of sterol biosynthesis in animal cells by 15-oxygenated sterols.

    abstract::The chemical syntheses of a number of C27 15-oxygenated sterols and their derivatives have been pursued to permit evaluation of their activity in the inhibition of sterol biosynthesis in animal cells in culture. Described herein are chemical syntheses of 3 alpha-benzoyloxy-5 alpha-cholest-8(14)-en-15-one, 5 alpha-chol...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Schroepfer GJ Jr,Parish EJ,Kandutsch AA

    更新日期:1979-11-01 00:00:00

  • Lipid chain mobility and packing in DOPC bilayers at cryogenic temperatures.

    abstract::Low-temperature molecular mobility and packing in biological tissues are important for their survival upon cryopreservation. Electron paramagnetic resonance (EPR) in its pulsed version of electron spin echo (ESE) allows studying stochastic librations of spin-labeled molecules, the type of motion which dominates at low...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: Golysheva EA,Dzuba SA

    更新日期:2020-01-01 00:00:00

  • Structure, supramolecular organization and thermotropic phase behavior of N-acyl tris homologs (n = 9-18): Structural analogs of apoptosis inducing ceramides.

    abstract::N-Acyl tris(hydroxymethyl)aminomethanes (N-acyl tris, NATs) are structural analogs of ceramides, which were reported to induce apoptosis either by elevation of ceramide levels or by activation of pro-apoptotic effectors that are physiological targets of ceramide. In this study, we synthesized and characterized a homol...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章


    authors: D S,Ravindar C,Swamy MJ

    更新日期:2018-12-01 00:00:00