cas 17131-52-1, 3-(4-METHOXYPHENOXY)-1,2-PROPANEDIOL

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Effective synthesis of non-racemic prenalterol based on spontaneous resolution of 3-(4-hydroxyphenoxy)propane-1,2-diol
Spontaneous resolution of rac-3-(4-hydroxyphenoxy)propane-1,2-diol has been successfully used in the synthesis of both enantiomers of chiral drug prenalterol.
Bredikhina, Zemfira A.,Kurenkov, Alexey V.,Bredikhin, Alexander A.
p. 198 - 199
(2019/04/25)

Asymmetric Hydrolytic and Aminolytic Kinetic Resolution of Racemic Epoxides using Recyclable Macrocyclic Chiral Cobalt(III) Salen Complexes
New chiral macrocyclic cobalt(III) salen complexes were synthesized and used as catalyst for the asymmetric kinetic resolution (AKR) of terminal epoxides and glycidyl ethers with aromatic/aliphatic amines and water as nucleophiles. This is the first occasion where a Co(III) salen complex demonstrated its ability to catalyze AKR as well as hydrolytic kinetic resolution (HKR) reactions. Excellent enantiomeric excesses of the epoxides, the corresponding amino alcohols and diols (upto 99%) with quantitative yields were achieved by using the chiral Co(III) salen complexes in dichloromethane at room temperature. This protocol was further extended for the synthesis of two important drug molecules, i.e., (S)-propranolol and (R)-naftopidil. The catalytic system was also explored for the synthesis of chirally pure diols and chiral cyclic carbonates using carbon dioxide as a greener renewable C1 source. The catalyst was recycled for upto 5 catalytic cycles with retention of enantioselectivity. (Figure presented.).
Tak, Rajkumar,Kumar, Manish,Menapara, Tusharkumar,Gupta, Naveen,Kureshy, Rukhsana I.,Khan, Noor-ul H.,Suresh
supporting information
p. 3990 - 4001
(2017/11/22)

Structure-activity relationships of lysophosphatidylserine analogs as agonists of G-protein-coupled receptors GPR34, P2Y10, and GPR174
Lysophosphatidylserine (LysoPS) is an endogenous lipid mediator generated by hydrolysis of membrane phospholipid phosphatidylserine. Recent ligand screening of orphan G-protein-coupled receptors (GPCRs) identified two LysoPS-specific human GPCRs, namely, P2Y10 (LPS2) and GPR174 (LPS3), which, together with previously reported GPR34 (LPS1), comprise a LysoPS receptor family. Herein, we examined the structure-activity relationships of a series of synthetic LysoPS analogues toward these recently deorphanized LysoPS receptors, based on the idea that LysoPS can be regarded as consisting of distinct modules (fatty acid, glycerol, and l-serine) connected by phosphodiester and ester linkages. Starting from the endogenous ligand (1-oleoyl-LysoPS, 1), we optimized the structure of each module and the ester linkage. Accordingly, we identified some structural requirements of each module for potency and for receptor subtype selectivity. Further assembly of individually structure-optimized modules yielded a series of potent and LysoPS receptor subtype-selective agonists, particularly for P2Y10 and GPR174.
Ikubo, Masaya,Inoue, Asuka,Nakamura, Sho,Jung, Sejin,Sayama, Misa,Otani, Yuko,Uwamizu, Akiharu,Suzuki, Keisuke,Kishi, Takayuki,Shuto, Akira,Ishiguro, Jun,Okudaira, Michiyo,Kano, Kuniyuki,Makide, Kumiko,Aoki, Junken,Ohwada, Tomohiko
supporting information
p. 4204 - 4219
(2015/06/08)

Synthesis and some features of phase behavior of chiral p-alkoxyphenyl glycerol ethers
A series of (S)-3-(4-alkoxyphenoxy)propane-1,2-diols was prepared with the enantiomeric excess 86-92% by Sharpless asymmetric dihydroxylation of 1-alkoxy-4-allyloxybenzenes with an AD-mix-β mixture. R-Enantiomers with enantiomeric excess 97-99% and racemic samples were obtained by reaction of sodium p-substituted phenolates with (R)- and rac-3-chloropropane-1,2-diol. The phase behavior of racemates and scalemates in the produced homolog series of glycerol aryl ethers with hydrocarbon substituents of various length was examined by means of thermomicroscopy. The higher memberes of the homolog series of both racemic and scalemic diols undergo at heating an enantiotropic phase transition to a smectic liquid crystal phase.
Fayzullin,Antonovich,Zakharychev,Bredikhina,Kurenkov,Bredikhin
p. 202 - 209
(2015/04/14)

Asymmetric hydrolytic kinetic resolution with recyclable polymeric Co(iii)-salen complexes: A practical strategy in the preparation of (S)-metoprolol, (S)-toliprolol and (S)-alprenolol: Computational rationale for enantioselectivity
A series of chiral polymeric Co(iii)-salen complexes based on a number of achiral and chiral linkers were synthesized and their catalytic performances were assessed in the asymmetric hydrolytic kinetic resolution of terminal epoxides. The effects of the linker were judiciously studied and it was found that in the case of the chiral BINOL-based polymeric salen complex 1, there was an enrichment in catalyst reactivity and enantioselectivity of the unreacted epoxide, particularly in the case of short as well as long chain aliphatic epoxides. Good isolated yields of the unreacted epoxide (up to 46% compared to 50% theoretical yield) along with high enantioselectivity (up to 99%) were obtained in most cases using catalyst 1. Further studies showed that catalyst 1 could retain its catalytic activity for six cycles under the present reaction conditions without any significant loss in activity or enantioselectivity. To show the practical applicability of the above synthesized catalyst we have synthesised some potent chiral β-blockers in moderate yield and high enantioselectivity using complex 1. The DFT (M06-L/6-31+G??//ONIOM(B3LYP/6-31G?:STO-3G)) calculations revealed that the chiral BINOL linker influences the enantioselectivity achieved with Co(iii)-salen complexes. Further, the transition state calculations show that the R-BINOL linker with the (S,S)-Co(iii)-salen complex is energetically preferred over the corresponding S-BINOL linker with the (S,S)-Co(iii)-salen complex for the HKR of 1,2-epoxyhexane. The role of non-covalent C-H?π interactions and steric effects has been discussed to control the HKR reaction of 1,2-epoxyhexane.
Roy, Tamal,Barik, Sunirmal,Kumar, Manish,Kureshy, Rukhsana I.,Ganguly, Bishwajit,Khan, Noor-Ul H.,Abdi, Sayed H. R.,Bajaj, Hari C.
p. 3899 - 3908
(2015/02/19)

One-pot synthesis of aryloxypropanediols from glycerol: Towards valuable chemicals from renewable sources
Glycerol offers an easy and green route for the synthesis of aryloxypropanediols of known pharmacological activity. Glycerol is selectively converted to aryloxypropanediols in a one-pot reaction, through in situ formed glycerol carbonate, under benign and solvent-free conditions. Catalyst and unreacted reagent can be recycled.
Truscello, Ada M.,Gambarotti, Cristian,Lauria, Mirvana,Auricchio, Sergio,Leonardi, Gabriella,Shisodia, Suresh U.,Citterio, Attilio
supporting information
p. 625 - 628
(2013/03/29)

Catalysis through temporary intramolecularity: Mechanistic investigations on aldehyde-catalyzed cope-type hydroamination lead to the discovery of a more efficient tethering catalyst
Mechanistic investigations on the aldehyde-catalyzed intermolecular hydroamination of allylic amines using N-alkylhydroxylamines are presented. Under the reaction conditions, the presence of a specific aldehyde catalyst allows formation of a mixed aminal intermediate, which permits intramolecular Cope-type hydroamination. The reaction was determined to be first-order in both the aldehyde catalyst (α-benzyloxyacetaldehyde) and the allylic amine. However, the reaction displays an inverse order behavior in benzylhydroxylamine, which reveals a significant off-cycle pathway and highlights the importance of an aldehyde catalyst that promotes a reversible aminal formation. Kinetic isotope effect experiments suggest that hydroamination is the rate-limiting step of this catalytic cycle. Overall, these results enabled the elaboration of a more accurate catalytic cycle and led to the development of a more efficient catalytic system for alkene hydroamination. The use of 5-10 mol % of paraformaldehyde proved more effective than the use of 20 mol % of α-benzyloxyacetaldehyde, leading to high yields of intermolecular hydroamination products within 24 h at 30 °C.
Guimond, Nicolas,MacDonald, Melissa J.,Lemieux, Valerie,Beauchemin, Andre M.
supporting information
p. 16571 - 16577,7
(2020/09/15)

Asymmetric organocatalytic efficiency of synthesized chiral β-amino alcohols in ring-opening of glycidol with phenols
A series of novel chiral β-amino alcohols 3-5 and 7-10 were synthesized by regioselective ring opening of epoxides and chiral amines with a straightforward method in high yields (up to 99 %). Kinetic resolution of racemic glycidol with phenols was achieved by using chiral amino alcohols as organocatalysts. Amino alcohols 5, 8 and 10 exhibited the highest enantioselectivities with p-cresol, phenol, and p-methoxyphenol by 63, 65, 58 % ee, respectively. The moderate enantioselectivities were observed with catalyst 9b towards all the nucleophiles (34-48 % ee). The ee values of the desired 3-aryloxy-1, 2-diols were determined by HPLC. This study presents an attractive tool for the synthesis of β-blockers and structurally complex molecules.
Aral, Tarik,Karakaplan, Mehmet,Hosgoeren, Halil
experimental part
p. 794 - 802
(2012/08/28)

Chiral nanoporous metal-metallosalen frameworks for hydrolytic kinetic resolution of epoxides
Chiral nanoporous metal-organic frameworks are constructed by using dicarboxyl-functionalized chiral Ni(salen) and Co(salen) ligands. The Co(salen)-based framework is shown to be an efficient and recyclable heterogeneous catalyst for hydrolytic kinetic resolution (HKR) of racemic epoxides with up to 99.5% ee. The MOF structure brings Co(salen) units into a highly dense arrangement and close proximity that enhances bimetallic cooperative interactions, leading to improved catalytic activity and enantioselectivity in HKR compared with its homogeneous analogues, especially at low catalyst/substrate ratios.
Zhu, Chengfeng,Yuan, Guozan,Chen, Xu,Yang, Zhiwei,Cui, Yong
supporting information; experimental part
p. 8058 - 8061
(2012/07/14)

Enantioselective complexation of chiral lariat crown ethers and chiral primary alkylammonium perchlorates
In order to investigate the enantiomeric recognition abilities toward 2 chiral alkylammonium perchlorates (AmI, AmII) by 1 H-NMR titration method in CDCl3, 4 chiral lariat ethers 8-11 with a (p-methoxyphenoxy) methyl flexible side arm were used. The most effective enantiomeric recognition was obtained by LCEs 9 and 11 toward AmII, by K R/KS 6.58 and KS/KR 6.63, respectively. The effect of macroring size, subunit of macroring, and side arm appeared to have strong influence on the binding ability of these alkylammonium ions. TUeBITAK.
Koeylue, M. Zafer,Aral, Tarik,Karakaplan, Mehmet,Kocakaya, Safak Oezhan,Hosgoeren, Halil
scheme or table
p. 174 - 179
(2012/05/05)

Synthesis of C2-symmetric chiral amino alcohols: Their usage as organocatalysts for enantioselective opening of epoxide ring
A series of -amino alcohols derivatives were synthesized from (R)-2-amino-1-butanol and (S)-1,2-propanediol, and they have been used as organocatalaysts in the racemic ring opening of epoxide in good yields with high enantiomeric excess (up to 97%). Copyright
Turgut, Yilmaz,Aral, Tarik,Karakaplan, Mehmet,Deniz, Pinar,Hosgoren, Halil
scheme or table
p. 3365 - 3377
(2011/01/04)

Directed evolution of an enantioselective epoxide hydrolase: Uncovering the source of enantioselectivity at each evolutionary stage
Directed evolution of enzymes as enantioselective catalysts in organic chemistry is an alternative to traditional asymmetric catalysis using chiral transition-metal complexes or organocatalysts, the different approaches often being complementary. Moreover, directed evolution studies allow us to learn more about how enzymes perform mechanistically. The present study concerns a previously evolved highly enantioselective mutant of the epoxide hydrolase from Aspergillus niger in the hydrolytic kinetic resolution of racemic glycidyl phenyl ether. Kinetic data, molecular dynamics calculations, molecular modeling, inhibition experiments, and X-raystructural work for the wild-type (WT) enzyme and the best mutant revea l the basis of the large increase in enantioselectivity (E = 4.6 versus E = 115). The overall structures of the WT and the mutant are essentially identical, but dramatic differences are observed in the active site asrevealed by the X-ray structures. All of the experimental and computati onal results support a model in which productive positioning of the preferred (S)-glycidyl phenyl ether, but not the (R)-enantiomer, forms the basis of enhanced enantioselectivity. Predictions regarding substrate scope and enantioselectivity of the best mutant are shown to be possible.
Reetz, Manfred T.,Bocola, Marco,Wang, Li-Wen,Sanchis, Joaquin,Cronin, Annette,et al.
supporting information; experimental part
p. 7334 - 7343
(2009/10/17)

Chiral lariat ethers as membrane carriers for chiral amino acids and their sodium and potassium salts
Four chiral lariat ethers 8-11 containing a (p-methoxyphenoxy) methyl side arm were used for chiral discrimination of amino acids in their zwitterionic form or as potassium and sodium salts in transport across a bulk chloroform membrane with satisfactory selectivity. The carriers that were employed exhibited different transport selectivity relative to the amino acids and their salts under study. The d/l selectivity strongly depends on the amino acids or their salts, and in some cases reverse selectivity has been obtained. The best selectivity was obtained in the case of tyrosine and its potassium salts for all carriers. The transport rates of amino acids and their salts were found to be controlled by factors such as the structure of the carriers and amino acids or their salts. Among these factors, it was also found that the side arm of the lariat ethers plays an important role in the transport process. As a consequence, the main goal of our investigation was to separate the chiral amino acids through liquid membranes.
Aydin, Isil,Aral, Tarik,Karakaplan, Mehmet,Hosgoeren, Halil
scheme or table
p. 179 - 183
(2009/05/30)

Synthesis and evaluation of lysophosphatidylserine analogues as inducers of mast cell degranulation. Potent activities of lysophosphatidylthreonine and its 2-deoxy derivative
In response to various exogenous stimuli, mast cells (MCs) release a wide variety of inflammatory mediators stored in their cytoplasmic granules and this release initiates subsequent allergic reactions. Lysophosphatidylserine (lysoPS) has been known as an exogenous inducer to potentiate histamine release from MCs, though even at submicromolar concentrations. In this study, through SAR studies on lysoPS against MC degranulation, we identified lysoPT, a threonine-containing lysophospholipid and its 2-deoxy derivative as novel strong agonists. LysoPT and its 2-deoxy derivative induced histamine release from MCs both in vitro and in vivo at a concentration less than one-tenth that of lysoPS. Notably, lysoPT did not activate a recently proposed lysoPS receptor on MCs, GPR34, demonstrating the presence of another undefined receptor reactive to both lysoPS and lysoPT that is involved in MC degranulation. Thus, the present strong agonists, lysoPT and its 2-deoxy derivative, will be useful tools to understand the mechanisms of lysoPS-induced activation of degranulation of MCs. 2009 American Chemical Society.
Iwashita, Masazumi,Makide, Kumiko,Nonomura, Taro,Misumi, Yoshimasa,Otani, Yuko,Ishida, Mayuko,Taguchi, Ryo,Tsujimoto, Masafumi,Aoki, Junken,Arai, Hiroyuki,Ohwada, Tomohiko
experimental part
p. 5837 - 5863
(2010/03/24)

Synthesis and crystal structure of chiral substituted (S)-2-[(4- methoxyphenoxy) methyl]-15-crown-5 ether with sodium perchlorate complex
The crystal and molecular structure of chiral crown ether, (S)-2-[(4-methoxyphenoxy)methyl]-15-crown-5...NaClO4, has been determined by single-crystal X-ray diffraction. The complex crystallizes in the orthorombic space group Pbca with Z = 8. Lattice parameters are a = 11.451(2), b = 12.842(3), c = 31.330(7) A. The structure was refined to R factor of 0.0547. The Na ion is heptacoordinated. The Na-Oether distances range from 2.363(4) to 2.433(4) A and average 2.404(5) A. Perchlorate anion is bounded to sodium ion asymmetrically; the Na-O8 and Na-O9 distances are 2.444(5) A and 2.607(5) A. The C-O and C-C distances of the 15-membered ring average 1.419(9) and 1.478(12) A while the O-C-C and C-O-C angles average 108.2(6°) and 115.4(6°).
Dogan, Nermin,Oezbey, Sueheyla,Karakaplan, Mehmet,Aral, Tarik
experimental part
p. 943 - 947
(2009/05/07)

4(2)-Methoxyphenyl glycerol ethers in the synthesis of nonracemic di-O,O-acylglycerols
Effective methods for the synthesis of nonracemic 4-and 2-methoxyphenyl glycerol ethers from nonracemic 3-chloropropanediols and by direct resolution of the racemate, respectively, were developed. Some existing discrepancies related to the to chiroptical properties of their derivatives were eliminated. Both ethers were used to synthesize nonracemic 3-O-aryloxy-1,2-di-O',O'-palmitoyl glycerols.
Bredikhina,Novikova,Efremov,Sharafutdinova,Bredikhin
experimental part
p. 2320 - 2323
(2010/02/15)

GLYCERO-COMPOUND HAVING TRIPLE BOND AND MEMBRANE MATERIAL CONTAINING THE SAME
The present invention provides a chemically stable and novel glycero-compound having one or two triple bonds, one molecule of a glycerol and one or two molecules of a fatty alcohol having a triple bond being linked through an ether bond, an organic group being linked to residual hydroxyl groups of the glycerol, which can be used as a membrane material for forming a vesicle membrane due to its high intermolecular cohesive force, and also provides a membrane forming material containing the same. The glycero-compound has a triple bond represented by the following general formula (1): wherein n and m each represents a number of 1 to 17 and the total (n+m) is a number of 4 to 18, n and m may be the same or different, and R represents a hydrogen atom, a metal atom, a phosphoric acid group, or an organic group which may be linked through a phosphoric acid group.
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Page/Page column 4-5

(2008/06/13)

Synthesis of phospholipids containing perfluorooctyl group and their interfacial properties
Highly fluorinated single-chained and/or double-chained phospholipids containing the perfluorooctyl group as the terminal segment of hydrophobic chains and a phosphocholine moiety as the hydrophilic headgroup were synthesized in order to investigate the effect of fluorinated segments on the stability of phospholipid monolayers formed at the air-water interface. Judging from the equilibrium spreading pressures (πes) of their monolayers at the air-water interface, all of the fluorinated phospholipids formed more stable monolayers than the corresponding non-fluorinated counterparts. In addition, the fluorinated double-chained phosphatidylcholine containing C-C triple bond (monoyne group) formed stable and fluid vesicle membranes in water, although the single-chained phospholipids did not form vesicle membranes but micellar solutions under the present conditions.
Takagi, Toshiyuki,Takai, Katsuki,Baba, Teruhiko,Kanamori, Toshiyuki
p. 133 - 138
(2008/03/13)

A practical synthesis of chiral 3-aryloxy-1,2-propanediols
Chiral 3-aryloxy-1,2-propanediols (1-5) of >96% ee were obtained in high yield by the nucleophilic addition of substituted phenols to chiral glycidol in the presence of piperidine hydrochloride as catalyst.
Karakaplan, Mehmet,Turgut, Yilmaz,Hosgoeren, Halil
p. 41 - 42
(2007/10/03)

Convenient synthesis of oxazolidinones by the use of halomethyloxirane, primary amine, and carbonate salt
Primary amines reacted with carbonate salts (Na2CO3, K2CO3, Cs2CO3, and Ag 2CO3) and halomethyloxiranes in the presence of a base such as DBU or TEA to give oxazolidinones in high yields. The use of K 2CO3 among these carbonate gave the best yield in this synthesis. A reaction mechanism was proposed that the oxazolidinone was obtained from an oxazinanone intermediate via a bicyclo[2.2.1] intermediate. The present reaction can be widely applied to convenient synthesis of useful N-substituted oxazolidinones and chiral oxazolidinones.
Osa, Yumiko,Hikima, Yuka,Sato, Yoko,Takino, Kouichi,Ida, Yoshihiro,Hirono, Shuichi,Nagase, Hiroshi
p. 5737 - 5740
(2007/10/03)

A facile and convenient chemoenzymatic synthesis of optically active O-(4-methoxyphenyl)-glycidol and 1,2-diacyl-sn-glycerol
A convenient preparation of the (R)- and (S)-enantiomers of O-(4-methoxyphenyl)-glycidol by a one-pot reduction of ketone 3 and in situ lipase mediated resolution is described. Activated moist aluminium oxide in the presence of Pseudomonas cepacia lipase immobilized on ceramic particles (PS-C) has been found effective for the transesterification leading to a high degree of enantioselectivity. These chiral glycidols were further used as a chiral precursor for the synthesis of biologically important 1,2-O-diacyl-sn-glycerol under mild reaction conditions. The present method is facile for the synthesis of chiral glycidols in high enantioselectivity when compared to the previously reported methods.
Kamal, Ahmed,Sandbhor, Mahendra,Shaik, Ahmad Ali,Malik, M. Shaheer
p. 1855 - 1859
(2007/10/03)

Jacobsen-type enantioselective hydrolysis of aryl glycidyl ethers. 31P NMR analysis of the enantiomeric composition of oxiranes
The enantioselective partial hydrolysis of a number of racemic aryl glycidyl ethers in the presence of chiral Co(salen)-catalyst was studied. The enantiomeric composition of the isolated (R)-aryl glycidyl ethers was analyzed by 31P NMR using optically active substituted 2-chloro-1,3,2- dioxaphospholanes. A synthesis of β-adrenoblocking agents (S)-toliprolol and (S)-moprolol based on the simultaneously obtained (S)-3-aryloxypropane-1,2- diols was proposed.
Bredikhin,Strunskaya,Novikova,Azancheev,Sharafutdinova,Bredikhina
p. 213 - 218
(2007/10/03)

Systematic search for conglomerates among glycerol aromatic monoethers: Guaifenesin and mephenesin are the cases
Within the family of biologically active 3-aryloxy-1,2-propanediols, three new conglomerate-forming compounds have been found and resolved into enantiomers using the entrainment procedure.
Bredikhin, Alexander A.,Bredikhina, Zemfira A.,Lazarev, Sergey N.,Savel'ev, Dmitry V.
p. 104 - 105
(2007/10/03)

Inhibitors of phosphatidyl myo-inositol cycle
The present invention relates to the preparation and biological activity of 3-deoxy-Dmyo-inositol ether lipid analogs as inhibitors of phosphatidylinositol-3-kinase signaling and cancer cell growth. The compounds of the present invention are useful as anti-tumor 5 agents which effectively inhibit the growth of mammalian cells.
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Figure 8

(2008/06/13)

Cyclic sulfites, key intermediates in synthesis of 1-alkylamino-3-aryloxy-2-propanols from glycidol
A number of 3-aryloxypropanedioles were obtained by treating glycidol with phenols. The latter with thionyl chloride afforded 4-aryloxymethyl-1,3,2-dioxathiolane 2-oxides. These compounds were also obtained from 4-chloromethyl-1,3,2-dioxathiolane 2-oxides by substitution aryloxy group for chlorine. The cyclic sulfides synthesized are universal intermediates in the synthesis of chiral aryloxypropanolamines among which are known β-adrenoblockaders, cardiovascular drugs. From (S)-glycidol, (S)-alprenolol, (S)-propanolol, and (S)-thymolol were synthesized.
Bredikhina,Savel'ev,Bredikhin
p. 213 - 219
(2007/10/03)

Naphthyloxy acetic acid derivatives and a pharmaceutical composition comprising them as an active ingredient
The naphthyloxyacetic acid derivatives of the formula (I) wherein A is H, -(alkylene)COOR1, -(alkylene)CONR2R3, -(alkylene)OH, -(alkylene)tetrazole, -(alkylene)CN; E is single bond or alkylene; G is —S—, —SO—, —SO2—, —O— or —NR4—; L is alkylene, —(CH2)m—CH═CH—(CH2)n— or —(CH2)x—CH(OH)—(CH2)y—; M is phenyl, phenyl(thio, oxy, amino), diphenylmethyl, diphenylmethyl(thio, oxy, amino), and pharmaceutical composition comprising them as an active ingradient. The compounds of the formula (I) can combine PGE2receptor and exhibit the activity to antagonize or agonize for PGE2receptor. Therefore, they are useful as anti-hyperlipemia, for the prevention of abortion, for analgesics, as antidiarrheals, sleep inducer, diuretic, anti-diabetes, abortient, cathartics, antiulcer, anti-gastritis or antihypertensive etc.
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Example 6(2)

(2010/11/29)

Ring opening of epoxides with carboxylates and phenoxides in micellar media catalyzed with Ce(OTf)4
Efficient ring opening reaction of epoxides with carboxylates and phenoxide anions catalyzed with ceric triflate is performed in micellar media. This new method is a useful procedure for the preparation of β-carboxy and phenoxy alcohols from epoxides under mild reaction conditions.
Iranpoor,Firouzabadi,Safavi,Shekarriz
p. 2287 - 2293
(2007/10/03)

Opening of glycidol with phenols in water using catalytic amounts of sodium hydroxide: A practical synthesis of 3-aryloxy-1,2-propanediols
A practical synthesis of enantiopure 3-aryloxy-1,2-propanediols by opening of (S)-glycidol with phenols under aqueous conditions using catalytic amounts of sodium hydroxide is described.
Palermo, Stephen,Waykole, Liladhar,Chen, Kau-Ming,Prashad, Mahavir,Prasad, Kapa,Repic, Oljan,Blacklock, Thomas J.
p. 1757 - 1761
(2007/10/03)

3'-modified oligonucleotide derivatives
Novel oligonucleotide analogs of the formulae I and II STR1 in which A, B, D, R1, R2, T, U, V, W, X, Y, Z, a, b, m, m', n and n' have the meanings stated in the description, with valuable physical, biological and pharmacological properties, and a process for the preparation thereof are described. Application thereof relates to the use as inhibitors of gene expression (antisense oligonucleotides, ribozymes, sense oligonucleotides and triplex forming oligonucleotides), as probes for detecting nucleic acids and as aids in molecular biology.
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(2008/06/13)

Synthesis and growth inhibitory properties of glycosides of 1-O- hexadecyl-2-O-methyl-sn-glycerol, analogs of the antitumor ether lipid ET- 18-OCH3 (edelfosine)
Glycosylated antitumor ether lipids (GAELs), analogs of 1-O-octadecyl- 2-O-methyl-sn-glycero-3-phosphocholine (1, ET-18-OCH3, edelfosine), were synthesized in good overall yields by glycosylation of 1-O-alkyl-2-O- methyl-sn-glycerol and tested for in vitro antineoplastic activity against a variety of murine and human tumor cell lines. Stereospecific glycosylation was achieved by the use of 2-O-acetyl-3,4,6-tri-O-benzylglucopyranosyl and - mannopyranosyl trichloroacetimidates as donors, with trimethylsilyl trifluoromethanesulfonate as catalyst in the presence of molecular sieves at -78 °C. The GAELs differ from 1 in having the sn-3-phosphocholine residue replaced by one of the following monosaccharide residues: β- and α-2- deoxy-D-arabino-hexopyranosyl, α-D-mannopyranosyl, 2-O-methyl-β-D- glucopyranosyl, and 2-O-methyl-α-D-mannopyranosyl. 1-O-Hexadecyl-2-O- methyl-3-O-(2'-deoxy-β-D-arabino-hexopyranosyl)-sn-glycerol (2) was more effective than 1 in inhibiting the growth of MCF-7 (human breast cancer) and its adriamycin-resistant form MCF-7/adriamycin, and murine Lewis lung cancer cells. 2-Deoxy-β-D-arabino-hexopyranoside 2 was also an effective growth inhibitor of two drug-resistant leukemic cell lines, P388/Adr and L1210/vmdr.
Marino-Albernas, José R.,Bittman, Robert,Peters, Andrew,Mayhew, Eric
p. 3241 - 3247
(2007/10/03)

N-Acyl-2-substituted-1,3-thiazolidines, a New Class of Non-narcotic Antitussive Agents: Studies Leading to the Discovery of Ethyl 2--β-oxothiazolidine-3-propanoate
The synthesis of a novel class of antitussive agents is described.The compounds were examined for antitussive activity in guinea pig after cough induction by electrical or chemical stimulation.Ethyl 2--β-oxothiazolidine-3-propanoate (BBR 2173, moguisteine, 7) and other structurally related compounds showed a significant level of activity, comparable to that of codeine and dextromethorphan.The compounds presented in this paper are characterized by the N-acyl-2-substituted-1,3-thiazolidine moiety, which is a novel entry in the field of antitussive agents.The serendipitous discovery of the role played by the thiazolidine moiety in the determining the antitussive effect promoted extensive investigations on these structures.This optimization process on N-acyl-2-substituted-1,3-thiazolidines led to the initial identification of 2--3--1,3-thiazolidine (18a) as an interesting lead compound.The careful study of the rapid and very complicated metabolism of 18a provided further insights for the design of newer related derivatives.The observation that the metabolic oxidation on the lateral chain's sulfur of 18a to sulfoxide maintained the antitussive properties suggested the introduction of isosteric functional groups with respect to the sulfoxide moiety.Subsequent structural modifications showed that hydrolyzable malonic residues in the 3-position of the thiazolidine ring were able to assure high antitussive activity.This optimization ultimately led to the selection of moguisteine (7) as the most effective and safest representative of the series.Moguisteine is completely devoid of unwanted side effects (such as sedation and addiction), and its activity was demonstrated also in clinical studies.
Gandolfi, Carmelo A.,Domenico, Roberto Di,Spinelli, Silvano,Gallico, Licia,Fiocchi, Luigi,et al.
p. 508 - 525
(2007/10/02)

A Practical Synthetic Route to Enantiopure 3-Aryloxy-1,2-propanediols from Chiral Glycidol
Chiral 3-aryloxy-1,2-propanediols of >98percent ee can be obtained in high yield by the nucleophilic addition of substituted phenols to chiral glycidol in the presence of triethylamine catalyst followed by recrystallization in absolute ethanol.Several enantiopure compounds of pharmaceutical significance are presented as examples.
Chen, Jian,Shum, Wilfred
p. 2379 - 2380
(2007/10/02)

Kinetic resolution of acyclic 1,2-diols using a sequential lipase- catalyzed transesterification in organic solvents
A method for the kinetic resolution of 3-(aryloxy)-1,2-propanediols rac- 1a-n without additional protection-deprotection steps using a lipase- catalyzed sequential transesterification with lipase amano PS has been developed. In the first step of this one-pot procedure the racemic 1,2-diols are acylated regioselectively at the primary hydroxy group without enantioselection. The subsequent acylation at the secondary hydroxy group of the formed primary monoacetate is responsible for high enantioselection. The enantioselectivity of this transformation depends significantly on the substitution pattern of the aryl ring and the organic solvent used. 3- (Aryloxy)-1,2-propanediols with substituents in the para-position show a much higher enantioselectivity than the corresponding derivatives with ortho- substituents. Among other substrates, the pharmaceuticals Mephenesin, Guaifenesin, and Chlorphenesin have been resolved. The replacement of the aryloxy by an alkyl substituent causes a dramatic decrease of enantioselectivity.
Theil,Weidner,Ballschuh,Kunath,Schick
p. 388 - 393
(2007/10/02)

Enantioselective Syntheses of 1-O-Benzyl-sn-glycerol and 1-O-Hexadecyl-2-O-methyl-sn-glycerol via Asymmetric Dihydroxylation of Allyl 4-Methoxyphenyl Ether. Use of AD-Mix Supplemented wih Potassium Persulfate
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Byun, Hoe-Sup,Kumar, Erukulla Ravi,Bittman, Robert
p. 2630 - 2633
(2007/10/02)

Asymmetric dihydroxylation of aryl allyl ethers
Asymmetric dihydroxylation of substituted aryl allyl ethers is described. Para-substituents are shown to favor high enantioselectivity (89-95%ee), while ortho-groups have a deleterious effect (28-63%ee). Four medicinal agents were prepared: guaifenesin (expectorant), mephenesin (muscle relaxant), chlorphenesin (antifungal) and propanolol (β-blocker).
Wang,Zhang,Sharpless
p. 2267 - 2270
(2007/10/02)

PRACTICAL ROUTE TO BOTH (S)- AND (R)-ENANTIOMERS OF O-(4-METHOXYPHENYL)GLYCIDOL USING (S)-1,2-O-ISOPROPYLIDENEGLYCEROL AS A COMMON PRECURSOR
Practical route to both (R)- and (S)-enantiomers of O-(4-methoxyphenyl)glycidol is devised using (S)-1,2-O-isopropylideneglycerol as a common chiral starting material.
Takano, Seiichi,Moriya, Minoru,Suzuki, Mahito,Iwabuchi, Yoshiharu,Sugihara, Takumichi,Ogasawara, Kunio
p. 1555 - 1563
(2007/10/02)

Ethers and thioethers having therapeutical activity, their preparation and pharmaceutical compositions containing them
Compounds of formula I wherein Ar is an optionally substituted phenyl ring; B is a single bond, a group -(CH2OCH2)nbeing n = 1 or 2, a a 2,4-disubstituted-1,3-dioxolane ring or a 2,4-disubstituted-1,3-thioxolane ring, R is a single bond, an optionally substituted methylene or ethylene group and T is 2-, 3- or 4-pyridyl, an optionally salified or esterified carboxy group or a carboxyamide group. Said compounds are useful in treatment of respiratory diseases.
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(2008/06/13)

Ouverture d'epoxydes par le N-hydroxycarbamates de methyle; syntheses de tetrahydrodioxazine-1,4,2 ones-3 et de carbomethoxy-2 tetrahydrodioxazines-1,4,2
The ring opening of epoxides in a basic medium by methyl N-hydroxycarbamate reacting as an N-protected hydroxylamine by its oxanion CH3O-CO-NHO(-) gives the corresponding carbomethoxyaminoxyalcohols 2.These compounds can react further to give: N,O-di(hydroxy-2' alkyl)hydroxylamines 3 by opening of a second epoxide molecule; diols RCH(OH)CH2OH 4 by rupture in basic medium of the N-O linkage of 2; 1,4,2-tetrahydrodioxazine-3 ones 5 by intramolecular cyclisation of 2.The oxanion CH3O-CO-NHO(-) attacks the primary carbon of the epoxide except in the case of epoxystyrene where as minor attack on the secondary carbon is also observed.The cyclization of carbomethoxyaminoxyalcohols 2 with aldehydes or their corresponding acetals in the presence of paratoluene sulfonic acid is a rapid and easy two step synthesis of 2-carbomethoxy-tetrahydrodioxazines-1,4,2 8.
Fruchier, Alain,Moragues, Veronique,Petrus, Clement,Petrus, Francoise
p. 173 - 182
(2007/10/02)

Crown ether compositions with sidearms affording enhanced cation binding
This invention relates to novel crown ether compositions which have been given the cognomen "lariat ethers". They have been designed with one or more arms bearing neutral donor groups capable of interacting with a complexed metal ion and thereby affording enhanced cation binding compared to simple crown ethers. Evidence of enhanced cation binding has been obtained and the compounds have also shown utility as phase transfer catalysts.
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(2008/06/13)

Crown Cation Complex Effects. 20. Syntheses and Cation Binding Properties of Carbon-Pivot Lariat Ethers
In an effort devise synthetic cation binders that will mimic the behavior of naturally occuring ionophores such as valinomycin, we have prepared approximately 30 macrocyclic (crown) polyethers bearing flexible side chains attached to the macro ring at carbon.In many of these "carbon-pivot" compounds, the side chain contains one or more neutral donor groups that, if in a suitable geometrical arrangement, may provide additional solvation to the macro-ring-bound cation.Although such donors often enhanced the cation binding ability, overall, the increases in stability constants were modest.The physical resemblance and concept of "roping and tying" the cation suggest the name "lariat ethers".Syntheses of these molecules and binding by them of Na+ and K+ cations are reported and conclusions drawn about the structural requirements and cation binding efficacy of these materials.
Dishong, Dennis M.,Diamond, Craig J.,Cinoman, Michael I.,Gokel, Geoge W.
p. 586 - 593
(2007/10/02)