- A NEW METHOD FOR THE STEREOPECIFIC SYNTHESIS OF ETHER PHOSPHOLIPIDS. PREPARATION OF THE AMIDE ANALOG OF PLATELET ACTIVATING FACTOR AND RELATED DERIVATIVES
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A nowel stereopecific synthesis of biologically active ether-phospholipids is reported.
- Chandrakumar, Nizal S.,Hajdu Joseph
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Read Online
- C10-ALKYLENE SUBSTITUTED 13-MEMBERED MACROLIDES AND USES THEREOF
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Provided are 13-membered macrolides for the treatment of infectious diseases. The 13-membered macrolides described herein are azaketolides. Also provided are methods for preparing the 13- membered macrolides, pharmaceutical compositions comprising the 13-membered macrolides, and methods of treating infectious diseases, and in particular, disease resulting from Gram negative bacteria using the disclosed macrolides. Formula (I)
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Paragraph 00603
(2020/06/10)
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- Benzoxaborole Antimalarial Agents. Part 5. Lead Optimization of Novel Amide Pyrazinyloxy Benzoxaboroles and Identification of a Preclinical Candidate
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Carboxamide pyrazinyloxy benzoxaboroles were investigated with the goal to identify a molecule with satisfactory antimalarial activity, physicochemical properties, pharmacokinetic profile, in vivo efficacy, and safety profile. This optimization effort discovered 46, which met our target candidate profile. Compound 46 had excellent activity against cultured Plasmodium falciparum, and in vivo against P. falciparum and P. berghei in infected mice. It exhibited good PK properties in mice, rats, and dogs. It was highly active against the other 11 P. falciparum strains, which are mostly resistant to chloroquine and pyrimethamine. The rapid parasite in vitro reduction and in vivo parasite clearance profile of 46 were similar to those of artemisinin and chloroquine, two rapid-acting antimalarials. It was nongenotoxic in an Ames assay, an in vitro micronucleus assay, and an in vivo rat micronucleus assay when dosed orally up to 2000 mg/kg. The combined properties of this novel benzoxaborole support its progression to preclinical development.
- Zhang, Yong-Kang,Plattner, Jacob J.,Easom, Eric E.,Jacobs, Robert T.,Guo, Denghui,Freund, Yvonne R.,Berry, Pamela,Ciaravino, Vic,Erve, John C. L.,Rosenthal, Philip J.,Campo, Brice,Gamo, Francisco-Javier,Sanz, Laura M.,Cao, Jianxin
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p. 5889 - 5908
(2017/07/22)
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- Cu(i)-Catalyzed oxidative homo-coupling of thiazoline-4-carboxylates: Synthesis of 4,4′-bithiazoline derivatives
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Cu(i)-Catalyzed oxidative homo-coupling of thiazoline-4-carboxylates with good functional group tolerance has been developed. The methodology presented an efficient method to directly construct vicinal carbon-hetero quaternary centers existing in numerous functional molecules and could be applied to the synthesis of 4,4′-bithiazoles which are difficult to prepare by direct C-H activation.
- Fang, Xinxin,Zhang, Kaifan,Yao, Hequan,Huang, Yue
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supporting information
p. 8030 - 8034
(2016/09/09)
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- Incorporation and visualization of azido-functionalized: N -oleoyl serinol in Jurkat cells, mouse brain astrocytes, 3T3 fibroblasts and human brain microvascular endothelial cells
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The synthesis and biological evaluation of azido-N-oleoyl serinol is reported. It mimicks biofunctional lipid ceramides and has shown to be capable of click reactions for cell membrane imaging in Jurkat and human brain microvascular endothelial cells.
- Walter,Collenburg,Japtok,Kleuser,Schneider-Schaulies,Müller,Becam,Schubert-Unkmeir,Kong,Bieberich,Seibel
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supporting information
p. 8612 - 8614
(2016/07/13)
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- The rapid synthesis of oxazolines and their heterogeneous oxidation to oxazoles under flow conditions
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A rapid flow synthesis of oxazolines and their oxidation to the corresponding oxazoles is reported. The oxazolines are prepared at room temperature in a stereospecific manner, with inversion of stereochemistry, from β-hydroxy amides using Deoxo-Fluor. The
- Gl?ckner, Steffen,Tran, Duc N.,Ingham, Richard J.,Fenner, Sabine,Wilson, Zoe E.,Battilocchio, Claudio,Ley, Steven V.
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supporting information
p. 207 - 214
(2015/02/02)
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- Synthesis of 2-oxazolines by in situ desilylation and cyclodehydration of β-hydroxyamides
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A powerful method for the synthesis of 2-oxazolines from silyl-protected β-hydroxyamides is reported. Using diethylaminosulfur trifluoride (DAST) or its tetrafluoroborate salt (XtalFluor-E), silyl-protected β-amidoalcohols can be in situ deprotected and d
- Brandst?tter, Marco,Roth, Fabian,Luedtke, Nathan W.
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- Synthesis and antibacterial activities of Yanglingmycin analogues
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The synthesis of Yanglingmycin and its enantiomer, along with eighteen Yanglingmycin analogues is reported. The structures were confirmed mainly by analyses of NMR spectral data. Antibacterial activity assays showed that Yanglingmycin and some of its analogues exhibited significant antibacterial activities against two important agricultural pathogenic bacteria, Ralstonia solanacearum and Pseudomonas syringae pv. actinidiae, with minimum inhibitory concentration (MIC) values ranging from 3.91 to 15.62 μg/mL. The antibacterial activities exhibited by Yanglingmycin and its analogues are promising, suggesting potential in the development of compounds for novel bactericides.
- Li, Long-Bo,Dan, Wen-Jia,Tan, Fang-Fang,Cui, Li-Hui,Yuan, Zhi-Peng,Wu, Wen-Jun,Zhang, Ji-Wen
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- I2-Catalyzed C-O Bond Formation and Dehydrogenation: Facile Synthesis of Oxazolines and Oxazoles Controlled by Bases
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A general method for the synthesis of oxazolines and oxazoles was developed through I2-catalyzed C-O bond formation and dehydrogenation with the same oxidant, TBHP. By simply tuning reaction bases, either oxazolines or oxazoles were selectively
- Gao, Wen-Chao,Hu, Fei,Huo, Yu-Ming,Chang, Hong-Hong,Li, Xing,Wei, Wen-Long
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supporting information
p. 3914 - 3917
(2015/08/18)
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- Enantioselective synthesis of monofluorinated allylic compounds: Pd-catalyzed asymmetric allylations of dimethyl 2-fluoromalonate using new N-sulfinyl-based ligands
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New chiral S,N- and S,P-ligands starting from tert-butanesulfinamide were synthesized in four steps, applying Pd-catalyzed asymmetric allylic substitutions of dimethyl 2-fluoromalonate. The induced effect of the Pd/S,N-ligand catalyst on the enantioselectivity depends on the steric demand of the substituent at the o-position of the pyridine ring. This method produced monofluorinated allylation products in up to high yield with high enantioselectivity.
- Gao, Ning,Zhao, Xiao-Ming,Cai, Cheng-Si,Cai, Jue-Wang
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p. 9551 - 9558
(2015/09/28)
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- Synthesis of protected α-alkyl lanthionine derivatives
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Protected α-alkyl lanthionine derivatives were synthesized in five steps starting from a known phenyloxazoline precursor. This approach involved the synthesis of a family of substituted cyclic sulfamidates and their regioselective opening by nucleophilic attack with a protected cysteine. This efficient multistep strategy affords various α-alkylated lanthionine derivatives in high yields.
- Deno?l, Thibaut,Zervosen, Astrid,Lemaire, Christian,Plenevaux, Alain,Luxen, André
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p. 4526 - 4533
(2014/06/10)
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- Pd(ii)-catalyzed direct C5-arylation of azole-4-carboxylates through double C-H bond cleavage
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The first palladium-catalyzed direct C5-arylation of azole-4-carboxylates with simple unactivated arenes through double C-H bond cleavage is realized. This protocol provided a straightforward access to diverse 5-arylsubstituted azole-4-carboxylic derivatives with good functional group tolerance. The Royal Society of Chemistry 2012.
- Li, Ziyuan,Ma, Ling,Xu, Jinyi,Kong, Lingyi,Wu, Xiaoming,Yao, Hequan
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p. 3763 - 3765
(2012/06/15)
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- Synthesis of 2-oxazolines and related N-containing heterocycles using [Et2NSF2]BF4 as a cyclodehydration agent
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The preparation of 2-oxazolines and related N-containing heterocycles from the corresponding hydroxyamides using XtalFluor-E ([Et2NSF 2s]BF4) as a cyclodehydration agent is described. A wide range of heterocycles are obtai
- Pouliot, Marie-France,Angers, Laetitia,Hamel, Jean-Denys,Paquin, Jean-Fran?ois
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p. 4121 - 4123
(2012/08/28)
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- Design, synthesis, and SAR studies of 4-substituted methoxylbenzoyl-aryl- thiazoles analogues as potent and orally bioavailable anticancer agents
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In a continued effort to improve upon the previously published 4-substituted methoxybenzoyl-aryl-thiazole (SMART) template, we explored chemodiverse "B" rings and "B" to "C" ring linkage. Further, to overcome the poor aqueous solubility of this series of agents, we introduced polar and ionizable hydrophilic groups to obtain water-soluble compounds. For instance, based on in vivo pharmacokinetic (PK) studies, an orally bioavailable phenyl-amino-thiazole (PAT) template was designed and synthesized in which an amino linkage was inserted between "A" and "B" rings of compound 1. The PAT template maintained nanomolar (nM) range potency against cancer cell lines via inhibiting tubulin polymerization and was not susceptible to P-glycoprotein mediated multidrug resistance in vitro, and markedly improved solubility and bioavailability compared with the SMART template (45a-c (PAT) vs 1 (SMART)).
- Lu, Yan,Li, Chien-Ming,Wang, Zhao,Chen, Jianjun,Mohler, Michael L.,Li, Wei,Dalton, James T.,Miller, Duane D.
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supporting information; experimental part
p. 4678 - 4693
(2011/09/14)
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- Catalytic asymmetric hydrogenation of N-Boc-imidazoles and oxazoles
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Substituted imidazoles and oxazoles were respectively hydrogenated into the corresponding chiral imidazolines and oxazolines (up to 99% ee). The highly enantioselective hydrogenation was achieved by using the chiral ruthenium catalyst, which is generated
- Kuwano, Ryoichi,Kameyama, Nao,Ikeda, Ryuhei
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supporting information; experimental part
p. 7312 - 7315
(2011/06/24)
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- COMPOUNDS FOR TREATMENT OF CANCER
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The present invention relates to novel compounds having anti-cancer activity, methods of making these compounds, and their use for treating cancer and drug-resistant tumors, e.g. melanoma, metastatic melanoma, drug resistant melanoma, prostate cancer and drug resistant prostate cancer.
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Paragraph 0034; 00263
(2011/10/03)
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- Expanded scope for the iridium-catalyzed asymmetric isomerization of primary allylic alcohols using readily accessible second-generation catalysts
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A second generation of chiral (P,N)-iridium catalysts - readily accessible from inexpensive l-serine - displays expanded scope for the asymmetric isomerization of primary allylic alcohols.
- Mantilli, Luca,Mazet, Clement
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supporting information; scheme or table
p. 445 - 447
(2010/04/04)
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- SYNTHESIS OF OXAZOLINE COMPOUNDS
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The present invention provides an improved process for preparing an oxazoline compound of the formula: (I) wherein R1 and R2 are independently hydrogen, sulfide, sulfoxide, sulfonyl, optionally substituted lower alkyl, optionally sub
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Page/Page column 12
(2010/04/03)
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- The use of phosphonium anhydrides for the synthesis of 2-oxazolines, 2-thiazolines and 2-dihydrooxazine under mild conditions
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β-Hydroxy amides 6 and 7 were treated with triphenylphosphonium anhydride trifluoromethane sulfonate (3), or the cyclic analogue 4, to generate 2-oxazolines 5 and 8 under mild conditions. The reaction was optimised by examining the number of equivalents of reagents 3 or 4, or diisopropylethyl amine required to best effect cyclisation. The effects of altering the reaction temperature, reaction time, concentration, solvent, and addition rate also were investigated. However, it was found that use of a trityl group to block reaction at the hydroxyl or thiol group of the starting amides, and subsequent in situ detritylation, in the absence of base, led to greatly improved yields. Reagent 4 offered significant advantages in the purification of products and was used to dehydrate a range of trityl derivatives to form simple oxazolines, thiazolines, and a dihydro-1,3-oxazine, in high yield (85-99%), as well as a tetrahydro-1,3-oxazepine (31%).
- Petersson, Maria J.,Jenkins, Ian D.,Loughlin, Wendy A.
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experimental part
p. 739 - 746
(2009/06/20)
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- Solid-phase synthesis of α-alkylserines via phase-transfer catalytic alkylation of polymer-supported 2-phenyl-2-oxazoline-4-carboxylate
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Described is the development of a new solid-phase synthetic method for α-alkylserines in which phase-transfer catalytic alkylation of polymer-supported 2-phenyl-2-oxazoline-4-carboxylate (12) is the key step. The easy preparation of the polymer-supported
- Lee, Jihye,Ha, Min Woo,Kim, Taek-Soo,Kim, Mi-Jeong,Ku, Jin-Mo,Jew, Sang-sup,Park, Hyeung-geun,Jeong, Byeong-Seon
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experimental part
p. 8839 - 8843
(2009/12/26)
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- Modular phosphite-oxazoline/oxazine ligand library for asymmetrie Pd-catalyzed allylic substitution reactions: scope and limitations - origin of enantioselectivity
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A library of phosphite-oxazoline/oxazine ligands L1-L15a-h has been synthesized and screened in the Pd-catalyzed allylic substitution reactions of several substrate types. These series of ligands can be prepared efficiently from easily accessible hydroxyl amino acid derivatives. Their modular nature enables the substituents/configurations in the oxazoline/oxazine moiety, alkyl backbone chain and in the biaryl phosphite moiety to be easily and systematically varied. By carefully selecting the ligand components, therefore, high regio- and enantioselectivities (ee values up to 99%) and good activities have been achieved in a broad range of mono- and disubstituted linear hindered and unhindered liner and cyclic substrates. The NMR studies on the Pd-π-allyl intermediates provide a deeper understanding about the effect of the ligand parameters on the origin of enantioselectivity. It also indicates that the nucleophilic attack takes place predominantly at the allylic terminal carbon atom located trans to the phosphite moiety.
- Dieguez, Montserrat,Pamies, Oscar
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experimental part
p. 3653 - 3669
(2009/04/23)
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- A flexible synthetic approach to the hennoxazoles
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Three advanced intermediates corresponding to the carbon skeleton of the hennoxazoles have been prepared. Central to the strategy is the synthesis of the oxazoles prior to coupling with the other fragments and a dithiane addition to allow for the generati
- Zylstra, Eric J.,She, Miles W.-L.,Salamant, Walter A.,Leahy, James W.
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p. 623 - 627
(2007/10/03)
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- A facile synthesis of oxazolines, thiazolines, and imidazolines using α,α-difluoroalkylamines
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β-Amino alcohols, β-amino thiols, and β-diamines can be converted to the corresponding oxazoline, thiazoline, and imidazoline derivatives, respectively, by reaction with α,α-difluoroalkylamines under mild conditions. The reaction is applicable for the synthesis of optically active heterocyclic compounds. Georg Thieme Verlag Stuttgart.
- Fukuhara, Tsuyoshi,Hasegawa, Chihiro,Hara, Shoji
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p. 1528 - 1534
(2008/02/05)
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- Synthesis and application of chiral N-heterocyclic carbene-oxazoline ligands: Iridium-catalyzed enantioselective hydrogenation
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Two libraries of enantiomerically pure imidazolium salts bearing an oxazoline unit were synthesized. Deprotonation of the imidazolium salts and complexation of the resulting oxazoline-carbene ligands to iridium(i) was achieved in one step by mixing the im
- Nanchen, Steve,Pfaltz, Andreas
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p. 4550 - 4558
(2008/02/07)
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- Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis
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The subject invention provides pharmaceutical compounds useful in the treatment of Type II diabetes. These compounds are advantageous because they are readily metabolized by the metabolic drug detoxification systems. Particularly, thiazolidinedione analogs that have been designed to include esters within the structure of the compounds are provided. This invention is also drawn to methods of treating disorders, such as diabetes, comprising the administration of therapeutically effective compositions comprising compounds that have been designed to be metabolized by serum or intracellular hydrolases and esterases. Pharmaceutical compositions of the ester-containing thiazolidinedione analogs are also taught.
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- Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis
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The subject invention provides pharmaceutical compounds useful in the treatment of Type II diabetes. These compounds are advantageous because they are readily metabolized by the metabolic drug detoxification systems. Particularly, thiazolidinedione analogs that have been designed to include esters within the structure of the compounds are provided. This invention is also drawn to methods of treating disorders, such as diabetes, comprising the administration of therapeutically effective compositions comprising compounds that have been designed to be metabolized by serum or intracellular hydrolases and esterases. Pharmaceutical compositions of the ester-containing thiazolidinedione analogs are also taught.
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- (S)-Serine derived N-O and N-P oxazoline ligands for asymmetric catalysis
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(S)-Serine methyl ester and a range of carboxylic acids RCO2H (a R=(η5-C5H4)Fe(η5-C 5Ph5), b (η5-C5H 4)Co(η4-C4Ph4/su
- Jones, Geraint,Richards, Christopher J.
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p. 653 - 664
(2007/10/03)
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- MATERIALS AND METHODS FOR THE TREATMENT OF DIABETES, HYPERLIPIDEMIA, HYPERCHOLESTEROLEMIA, AND ATHEROSCLEROSIS
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The subject invention provides pharmaceutical compounds useful in the treatment of Type II diabetes. These compounds are advantageous because they are readily metabolized by the metabolic drug detoxification systems. Particularly, thiazolidinedione analogs that have been designed to include esters within the structure of the compounds are provided. This invention is also drawn to methods of treating disorders, such as diabetes, comprising the administration of therapeutically effective compositions comprising compounds that have been designed to be metabolized by serum or intracellular hydrolases and esterases. Pharmaceutical compositions of the ester-containing thiazolidinedione analogs are also taught.
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Page column 43
(2010/02/07)
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- New Dihydroxy Bis(Oxazoline) Ligands for the Palladium-Catalyzed Asymmetric Allylic Alkylation: Experimental Investigations of the Origin of the Reversal of the Enantioselectivity
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The origin of the reversal of the enantioselectivity in the palladium-catalyzed allylic alkylation of rac-1,3-diphenyl-2-propenyl acetate with dimethyl malonate anion using chiral dihydroxy bis(oxazoline) "BO" ligands derived from (1S,2S)-(+)-2-amino-1-ph
- Ait-Haddou, Hassan,Hoarau, Olivier,Cramailere, Dimitri,Pezet, Frederic,Daran, Jean-Claude,Balavoine, Gilbert G. A.
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p. 699 - 707
(2007/10/03)
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- Predetermined helical chirality in octahedral complexes with a novel pentadentate C2-symmetrical chiral bis(oxazoline) ligand
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The first example of the pentadentate bis(oxazolines) has been synthesized using a modular approach that readily provides access to this ligand class. This ligand allows the controlled transfer of carbon-centered to octahedral, metal-centered chirality, a
- Seitz, Michael,Kaiser, Anja,Powell, Douglas R.,Borovik, Andrew S.,Reiser, Oliver
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p. 737 - 741
(2007/10/03)
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- Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis
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The subject invention provides pharmaceutical compounds useful in the treatment of Type II diabetes. These compounds are advantageous because they are readily metabolized by the metabolic drug detoxification systems. Particularly, thiazolidinedione analogs that have been designed to include esters within the structure of the compounds are provided. This invention is also drawn to methods of treating disorders, such as diabetes, comprising the administration of therapeutically effective compositions comprising compounds that have been designed to be metabolized by serum or intracellular hydrolases and esterases. Pharmaceutical compositions of the ester-containing thiazolidinedione analogs are also taught.
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- Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis
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The subject invention provides pharmaceutical compounds useful in the treatment of Type II diabetes. These compounds are advantageous because they are readily metabolized by the metabolic drug detoxification systems. Particularly, thiazolidinedione analogs that have been designed to include esters within the structure of the compounds are provided. This invention is also drawn to methods of treating disorders, such as diabetes, comprising the administration of therapeutically effective compositions comprising compounds that have been designed to be metabolized by serum or intracellular hydrolases and esterases. Pharmaceutical compositions of the ester-containing thiazolidinedione analogs are also taught.
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- Efficient synthesis of β-halogeno protected L-alanines and their β-phosphonium derivatives
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Ring opening of oxazolines, prepared from L-serinates, with trimethylsilyl halides (TMSX) led to β-halogeno-N-benzoyl-α-amino esters in good to excellent yields. Quaternization of triphenylphosphine by the β-bromo or -iodo amino esters gave the corresponding β-phosphonium salts in overall yields of up to 93% and with e.e. >96%. Hydrolysis of the ester function afforded the phosphonium salt bearing an N-benzoyl-α-amino acid substituent, with partial racemization. However, the reaction of the TMSX with the carboxylic salt, prepared by saponification of the starting oxazoline ester, furnished the corresponding β-halogeno-N-benzoyl-α-amino acids in 70-95% yields. Quaternization of triphenylphosphine by the bromo or iodo derivatives led to the phosphonium salts bearing a free acid function in 95% yield, without racemization. The efficiency of this synthesis was demonstrated by the preparation of these phosphonium salts in excellent overall yields, by a one-pot procedure starting from the oxazoline.
- Meyer, Franck,Laaziri, Abdelhamid,Papini, Anna Maria,Uziel, Jacques,Juge, Sylvain
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p. 2229 - 2238
(2007/10/03)
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- IMMUNOMODULATORY COMPOUNDS AND METHODS OF USE THEREOF
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The present invention is directed to methods of treating diseases and disorders related to immune responses by administering one or more immunomodulatory compounds. In particular, the invention is directed to methods of stimulating and reducing immune responses, treating autoimmune conditions, treating allergic reactions and asthma, and preventing ischemic damage and asthma by administering one or more immunomodulatory compounds.
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- Simple phosphinite-oxazoline ligands for asymmetric catalysis
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4-(Hydroxymethyl)oxazolines, derived from (S)-serine methyl ester and a variety of acid chlorides (RCOCl), were reacted with Ph2PCl to give new phosphinite-oxazoline P-N ligands. These mediate the palladium catalysed asymmetric alkylation with
- Jones, Geraint,Richards, Christopher J.
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p. 5553 - 5555
(2007/10/03)
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- Benzamide bioisosteres incorporating dihydroheteroazole substructures: EPC synthesis and SAR leading to a selective dopamine D4 receptor partial agonist (FAUC 179)
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Conformationally restricted benzamide bioisosteres were investigated when the chiral phenyldihydroimidazole derivative 4e (FAUC 179) showed strong and highly selective dopamine D4 receptor binding (Kihigh = 0.95 nM). Mitogenesis experiments indicated partial agonist properties (42%). EPC syntheses of the target compounds of type 4 were performed starting from α-amino acids.
- Einsiedel, Juergen,Huebner, Harald,Gmeiner, Peter
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p. 2533 - 2536
(2007/10/03)
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- Highly enantio- and regioselective allylic alkylations catalyzed by chiral [bis(dihydrooxazole)]molybdenum complexes
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A series of chiral C2-symmetric bis[dihydrooxazoles] with a trans-1,2-diaminocyclohexane backbone was synthesized. In view of the promising results obtained by Trost et al. with related bis[pyridine] ligands, we tested these new ligands in the enantioselective molybdenum-catalyzed allylic alkylation of 1- and 3-monosubstituted allylic substrates. Enantiomer excesses of up to 98% and branched/linear ratios of up to 11:1 were obtained with (E)-3-(alkyl)allyl carbonates. (E)-3-Phenoxyallyl acetate gave a branched/linear ratio of > 20:1 and an ee of 98%. Crystal structures of the free ligand 7a and of its tricarbonylmolybdenum(0) complex 28 are reported.
- Glorius, Frank,Neuburger, Markus,Pfaltz, Andreas
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p. 3178 - 3196
(2007/10/03)
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- Triphenylphosphonium salts bearing an L-alanyl substituent: Short synthesis and enantiomeric analysis by NMR
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A short, practical stereospecific synthesis of triphenylphosphonium salts bearing an L-(N-benzoyl)-alanyl substituent from L-serine is described. The key step is the ring opening of an oxazoline salt derived from serine with trimethylsilyl halide, giving
- Meyer, Franck,Uziel, Jacques,Papini, Anne Marie,Jugé, Sylvain
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p. 3981 - 3984
(2007/10/03)
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- Synthesis of functionalized oxazolines and oxazoles with DAST and Deoxo-Fluor.
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[formula: see text] A mild and highly efficient cyclization of beta-hydroxy amides to oxazolines is described using DAST and Deoxo-Fluor reagents. A one-pot protocol for the synthesis of oxazoles from beta-hydroxy amides is also presented.
- Phillips,Uto,Wipf,Reno,Williams
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p. 1165 - 1168
(2007/10/03)
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- Enantioselective molybdenum-catalyzed allylic alkylation using chiral bisoxazoline ligands
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(equation presented) 54-86% yield R = Ph, Pr, CH3, OCH3, OPh 76 to 99% ee of A A : B = 8 : 1 up to >20 : 1 A series of chiral C2-symmetric bisoxazolines with trans-1,2-diaminocyclohexane backbones was synthesized. In view
- Glorius, Frank,Pfaltz, Andreas
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p. 141 - 144
(2008/02/12)
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- Electrophilic ring opening of oxazolines derived from serine and threonine: A practical entry to N(N)-protected β-halogeno α-aminoesters
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Treatment of oxazolines 4a-c derived from serine or threonine with chloroformates, leads to the oxazoline ring opening and to the formation of N,N-protected β-chloro-α-aminoesters la-e in 30-88% isolated yields. In the presence of NaI (0.9 equiv), oxazolines 4a,b,d react with ethyl chloroformate to afford the N,N-protected β-iodo α-amino esters 1f-h (67-89% yields), whereas the reaction of 4a,b with trimethylsilyl halide gives the analogous N-benzoyl β-halogeno derivatives 1i,k with 30-86% yields.
- Laaziri, Abdelhamid,Uziel, Jacques,Juge, Sylvain
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p. 437 - 447
(2007/10/03)
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- The efficient, enantioselective synthesis of aza sugars from amino acids. 1. The polyhydroxylated pyrrolidines
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Beginning with (+)-serine or (-)-serine, as appropriate, convenient, high-yield, enantioselective synthesis of all eight stereoisomeric 2-hydroxymethyl-3,4-dihydroxypyrrolidines (the enantiomeric pairs of iminoribitol, -arabinitol, -xylitol, and -lyxitol) can be effected. The absolute configuration of the starting amino acid defines the set of azasugars produced.
- Huang, Yifang,Dalton, David R.,Carroll, Patrick J.
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p. 372 - 376
(2007/10/03)
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- Oxidation of oxazolines and thiazolines to oxazoles and thiazoles. Application of the Kharasch-Sosnovsky reaction
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Using a modification of the Kharasch-Sosnovsky reaction, the oxidation of oxazolines and thiazolines bearing a variety of 2-alkyl substituents (chiral and achiral) were smoothly oxidized to their corresponding oxazoles and thiazoles, respectively. The key feature involved in the successful implementation of this important oxidation was the use of a mixture of Cu(I) and Cu(II) salts to enhance the oxidation of the intermediate captodative radical, 24. The main limitation of this method was shown when the oxidation failed with oxazolines/thiazolines lacking the carboalkoxy group at C-4.
- Meyers,Tavares, Francis X.
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p. 8207 - 8215
(2007/10/03)
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- Stereoselective Cycloaddition of Nitrile Oxides to 4-Vinyl-Oxazolines and -Oxazolidines
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Cycloaddition of nitrile oxides to 4-vinyl-2-oxazoline 1 and to 4-vinyloxazolidine 2 afford diastereomeric mixtures of 2-isoxazolines in which the erythro product predominates (32-64percent d.e.).In contrast, the corresponding reactions with acyclic analogue 3 favoured the threo-adducts and were less selective (8-20percent d.e.).Key Words: 1,3-dipolar cycloaddition; nitrile oxides; isoxazolines
- Boyd, Ewan C.,Paton, R. Michael
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p. 3169 - 3172
(2007/10/02)
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- Asymmetric addition to chiral aromatic and unsaturated oxazolines using a novel chiral auxillary
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By utilizing S-serine, both enantiomers of the reduced methoxyamino alcohol (12) were efficiently prepared. The corresponding oxazolines, prepared from these auxiliaries, showed favorable properties toward additions to naphthalenes 22 and cyclohexene, 27.
- Meyers,Schmidt,McKennon
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p. 250 - 262
(2007/10/02)
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- SYNTHESIS OF FLUORINE-CONTAINING ISOSTERES OF SPHINGOSINE AS INACTIVATORS OF PROTEIN KINASE C
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Syntheses of isosteres of D-sphingosine in which either the primary or the secondary hydroxyl group of the parent compound has been replaced by a fluorine substituent are described.
- Kozikowski, Alan P.,Wu, Jiang-Ping
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p. 4309 - 4312
(2007/10/02)
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- A MILD PROCEDURE FOR THE PREPARATION OF 2-OXAZOLINES
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A general procedure using triphenylphosphine and diethylazodicarboxylate to prepare 2-oxazolines is described.
- Roush, David M.,Patel, Manorama M.
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p. 675 - 680
(2007/10/02)
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- SYNTHESIS OF (4E,8E,2S,3R,2'R)-N-2'-HYDROXYHEXADECANOYL-1-O-β-D-GLUCOPYRANOSYL-9-METHYL-4,8-SPHINGADIENINE, THE FRUITING-INDUCING CEREBROSIDE IN A BASIDIOMYCETE SCHIZOPHYLLUM COMMUNE
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The title compound was synthesized by employing (R)-2-aminohexadecanoic acid, D-glucose and (S)-serine as the chiral sources, and the synthetic sample was found to be chemically and biologically identical with the fruiting-inducing cerebroside isolated fr
- Mori, Kenji,Funaki, Yuji
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p. 2379 - 2386
(2007/10/02)
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