- Enantioselective synthesis and antiproliferative properties of an ilmofosine analog, 2'-(trimethylammonio)ethyl 3-(hexadecyloxy)-2- (methoxymethyl)propyl phosphate, on epithelial cancer cell growth
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An asymmetric synthesis of the 1-alkyloxy analog of the thioether phosphocholine ilmofesine (BM 41.440, rac-1), 2'-(trimethylammonio)ethyl 3- (hexadecyloxy)-2-(methoxymethyl)propyl phosphate (2), is described. Stereoselectivity was obtained in an asymmetric hydroborationoxidation sequence carried out on a 2,2-disubstituted 1-alkene, 3-(hexadecyloxy)-2- (methoxymethyl)-1-propene (9), which was prepared by starting with either ethyl acrylate or ethyl α-(hydroxymethyl)acrylate (3). (R)- and (S)-2 and rac-1 were highly effective in inhibiting the proliferation of the breast adenocarcinoma cell line MCF-7 (IC50, 2 μM), moderately effective against A549 (non-small-cell lung adenocarcinoma) (IC50, 8-10 μM), and less effective against A427 (large cell lung carcinoma) (IC50, ~20 μM). The in vitro cytotoxicity against the three epithelial cancer cell lines was independent of the configuration about C-2 of the glycerol backbone of 2 and was also not altered by substitution of oxygen for sulfur in the sn-1 ether linkage of ilmofosine.
- Bittman,Byun,Reddy,Samadder,Arthur
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- Diastereoselective synthesis of 2,6-disubstituted 4-(Dimethoxymethyl)tetra- hydropyrans using TMSOTf-promoted prins-pinacol cyclization
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We have described a highly diastereoselective synthesis of 2,6-disubstituted 4-(dimethoxymethyl)tetrahydropyrans via TMSOTf-promoted Prins-pinacol reaction of methylene diol with acetals. This reaction provides an efficient procedure to synthesize functionalized tetrahydropyrans containing an acetal group at the C4 position with all-cis 2,4,6 relative configuration.
- Kim, Youngseub,Lee, Jaekyun,Pae, Aenim,Cho, Yongseo,Min, Sun-Joon
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- THE SYNTHESIS OF VOLATILE STREPTOMYCES LACTONES
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A synthetic pathway to the volatile streptomyces lactones has been developed using as a key step sequential addition / alkylation to anions generated from 2,2-dimethyl-5-methylene-1,3-dioxane.
- Kan-Yin, Zhang,Borgerding, Anthony J.,Carlson, Robert M.
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- Method for preparing 2-methyl-1, 3-propylene glycol from isobutene
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The invention discloses a method for preparing 2-methyl-1, 3-propylene glycol from isobutene. The method comprises the following steps: mixing isobutene with acetic acid and oxygen, and carrying out an oxyacetylation reaction under the action of a supported palladium-molybdenum catalyst to obtain 2-methylene propane-1, 3-diacetoxy, namely a compound (C); carrying out transesterification on the compound (C) under the action of a basic catalyst to obtain 2-methylene-1, 3-propylene glycol, namely a compound (D); and carrying out hydrogenation reaction on the compound (D) to obtain the 2-methyl-1,3-propylene glycol. According to the method, the 2-methyl-1, 3-propylene glycol can be generated with high selectivity, and the whole process is high in atom utilization rate, environmentally friendly and suitable for large-scale industrial application.
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Paragraph 0054-0055; 0059-0060; 0064; 0067; 0069-0070; 0072-
(2021/02/10)
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- METHODS AND COMPOSITIONS FOR TERPENOID SYNTHESIS
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In one aspect, the disclosure relates to methods for preparation of terpene and terpene-like molecules. In a further aspect, the disclosure relates to the products of the disclosed methods, i.e., terpene and terpene-like molecules prepared using the disclosed methods. Intermediates for the synthesis of a wide variety of terpenoids are γ-allyl Knoevenagel adducts or quasi γ-allyl Knoevenagel adducts are disclosed. In various aspects, methods of preparing terpenoids through these intermediates are disclosed. The methods can comprise α-alkylation of an allylic electrophile followed by ring-closure metathesis to a polycyclic terpenoid structure. In a further aspect, the disclosure pertains to terpenoid frameworks, and compounds prepared via disclosed oxidation and substitution reactions on the disclosed terpenoid frameworks. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present disclosure.
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Paragraph 0090; 00143
(2018/04/13)
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- Synthesis of isofagomine and a new C6 pyrrolidine azasugar with potential biological activity
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An efficient asymmetric synthesis of isofagomine, based on a precursor containing three differentiated hydroxyl functions, is described. The side product in the key alkylation step is converted into (2S,3R,4R)-2,4- bis(hydroxymethyl)-3-hydroxypyrrolidine, a new C6 pyrrolidine azasugar, which inhibits α-glucosidase from yeast. Georg Thieme Verlag Stuttgart.
- Espeel, Pieter E. R.,Piens, Kathleen,Callewaert, Nico,Van Der Eycken, Johan
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p. 2321 - 2325
(2009/05/07)
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- Tethered α-boryl radical cyclizations of haloalkyl boronates
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Boroalkyl radicals readily cyclize onto alkenyl and alkynyl traps tethered via a C-B-O linkage. Oxidative cleavage of the C-B bond of the temporary connection following cyclization affords 1,3-diols in good yields.
- Batey, Robert A.,Smil, David V.
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p. 9183 - 9187
(2007/10/03)
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- Palladium-catalysed carbonyl allylation by 2-methylenepropane-1,3-diol
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2-Methylenepropane-1,3-diol first allylates an aldehyde exclusively at the allylic alcohol moiety at room temperature and then, at 50°C, allylates another aldehyde also at the allylic alcohol moiety, in the presence of a catalytic amount of PdCl2(PhCN)2 with tin(II) chloride.
- Masuyama, Yoshiro,Kagawa, Masaaki,Kurusu, Yasuhiko
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p. 1585 - 1586
(2007/10/03)
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- Improved syntheses of ethyl α-(bromomethyl)acrylate and 2-methylene-1,3- propanediol via ethyl α-(hydroxymethyl)acrylate
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Ethyl α-(bromomethyl)acrylate (1) and 2-methylene-1,3-propanediol (2) have been prepared via formalhedyde addition to ethyl acrylate in the presence of DABCO, giving α, β-unsaturated ester 3. Reduction of hydroxy ester 3 with one equivalent of alane, then borohydride reduction of the resulting aldehyde 4 gives 2.
- Byun,Reddy,Bittman
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p. 1371 - 1374
(2007/10/02)
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- Derivatives of 2-methylenepropane-1,3-diol as new antagonists of platelet activating factor
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Two new achiral platelet activating factor (PAF) antagonists, N-[5-[[2-methylene-3-[[(octadecylamino)carbonyl]oxy]propoxy]carbonyl]p2 entyl]pyridinium bromide (9) and 3-[6-[[2-methylene-3-[[(octadecylamino)carbonyl]oxy]propoxy]carbonyl]h2 exyl]thiazolium bromide (10) were synthesized from 2-methylenepropane-1,3-diol (5). Platelet aggregation in platelet-rich plasma from rabbits, induced by racemic C16-PAF, was competitively antagonized by 9 or 10. At concentrations ≤ 10-4 M, neither compound 9 nor compound 10 caused platelet aggregation, nor did they inhibit platelet aggregation induced by collagen or adenosine diphosphate. Bronchoconstriction in the guinea pig and hypotension in the rat, induced by racemic C16-PAF, were also effectively antagonized by 9 and 10. Both appear to be more potent as PAF antagonists than Takeda's CV-3988.
- Grue-Sorensen,Mann Nielsen,Kaergaard Nielsen
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p. 1174 - 1178
(2007/10/02)
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- Stereospecific process for production of c-5-aralkoxy-r-2-substituted-5-alkyl-1,3-dioxanes and intermediates
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Production of c-5-aralkoxy-r-2-substituted-5-alkyl-1,3-dioxanes by epoxidizing the double bond of a 2-substituted-5-alkylidene-1,3-dioxane to form a cis epoxide, hydrogenolyzing said epoxide to form a 2-substituted-5-alkyl-5-hydroxy-1,3-dioxane in which there is a cis relationship between the 5-hydroxy and the 2-substituent, and etherifying said hydroxydioxane with an aralkyl halide.
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