cas 141410-06-2, 1H-Indole-2-carboxylicacid,2,3-dihydro-,methylester,(2S)-(9CI)

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Promoting the Furan Ring-Opening Reaction to Access New Donor–Acceptor Stenhouse Adducts with Hexafluoroisopropanol
Donor–acceptor Stenhouse adducts (DASAs) are visible-light-responsive photoswitches with a variety of emerging applications in photoresponsive materials. Their two-step modular synthesis, centered on the nucleophilic ring opening of an activated furan, ma
Clerc, Michèle,Stricker, Friedrich,Ulrich, Sebastian,Sroda, Miranda,Bruns, Nico,Boesel, Luciano F.,Read de Alaniz, Javier
supporting information
p. 10219 - 10227
(2021/03/22)

Chiral Arylated Amines via C?N Coupling of Chiral Amines with Aryl Bromides Promoted by Light
The Buchwald-Hartwig C-N coupling reaction has found widespread applications in organic synthesis. Over the past two decades or so, many improved catalysts have been introduced, allowing various amines and aryl electrophiles to be readily used nowadays. However, there lacks a protocol that could be used to couple a wide range of chiral amines and aryl halides, without erosion of the enantiomeric excess (ee). Reported in this article is a method based on molecular Ni catalysis driven by light, which enables stereoretentive C-N coupling of optically active amines, amino alcohols, and amino acid esters with aryl bromides, with no need for any external photosensitizer. The method is effective for a wide variety of coupling partners, including those bearing functional groups sensitive to bases and nucleophiles, thus providing a viable alternative to accessing synthetically important chiral N-aryl amines, amino alcohols, and amino acids esters. Its viability is demonstrated by 92 examples with up to 99 % ee.
Song, Geyang,Yang, Liu,Li, Jing-Sheng,Tang, Wei-Jun,Zhang, Wei,Cao, Rui,Wang, Chao,Xiao, Jianliang,Xue, Dong
supporting information
p. 21536 - 21542
(2021/08/23)

Asymmetric Counteranion Directed Catalytic Heck/Tsuji-Trost Annulation of Aryl Iodides and 1,3-Dienes
A chiral anion-mediated asymmetric Heck/Tsuji-Trost reaction of aryl iodides and 1,3-dienes is presented. Chiral indoline derivatives could be afforded with remarkably higher yields and enantioselectivities than our previous chiral ligand-based method. Silver carbonate is employed as both base and halide scavenger to ensure fast and recyclable exchange of the catalytic amount of chiral anions. Fast salt metathesis, as well as the acceleration effect of the chiral anion, could both benefit the stereocontrol of the reaction.
Xu, Jia-Cheng,Yin, Yi-Zhuo,Han, Zhi-Yong
supporting information
p. 3834 - 3838
(2021/05/26)

A Proline Mimetic for the Design of New Stable Secondary Structures: Solvent-Dependent Amide Bond Isomerization of (S)-Indoline-2-carboxylic Acid Derivatives
A thorough experimental and computational study on the conformational properties of (S)-indoline-2-carboxylic acid derivatives has been conducted. Methyl (S)-1-acetylindoline-2-carboxylate, both a mimetic of proline and phenylalanine, shows a remarkable tendency toward the cis amide isomer when dissolved in polar solvents. This behavior is opposite to the general preference of proline for the trans isomer, making indoline-2-carboxylic acid a good candidate for the design of different secondary structures and new materials.
Pollastrini, Matteo,Lipparini, Filippo,Pasquinelli, Luca,Balzano, Federica,Barretta, Gloria Uccello,Pescitelli, Gennaro,Angelici, Gaetano
p. 7946 - 7954
(2021/06/28)

N-ALKYLSULFONYL INDOLINE COMPOUND, AGRICULTURAL AND HORTICULTURAL INSECTICIDE COMPRISING THE COMPOUND, AND METHOD FOR USING THE INSECTICIDE
In crop production in the fields of agriculture, horticulture and the like, the damage caused by insect pests etc. is still immense, and insect pests resistant to existing insecticides have emerged. Under such circumstances, the development of novel agricultural and horticultural insecticides is desired. The present invention provides an agricultural and horticultural insecticide comprising the indoline compound represented by the general formula (1): (wherein R1 and R4 are hydrogen atoms, R2 and R3 are halogen atoms, R5 is a haloalkyl group, Ra, Rb and Rc are hydrogen atoms, A1 is a CH group, A2 is a nitrogen atom, A3 is N-Me, m is 2, and n is 1), or a salt thereof as an active ingredient; and a method for using the insecticide.
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Paragraph 0172; 0173

(2020/04/09)

Base-assisted intramolecular c-n coupling reaction from nh2-bound cyclopalladated l -phenylalanine to indoline-2-carboxylic acid
The deprotonative intramolecular-amination reaction of phenylalanine-derived palladacycles has been investigated to highlight a facile carbonate-assisted N-H activation before the C-N bond formation. A major counterion effect led to divergent pathways whereby the SPhos-Pd complexes with iodine, triflate, or trifluoroacetate anions were key intermediates to afford access to (S)-2-indolinecarboxylic acid derivatives.
Afonso, Carlos,Brière, Jean-Fran?ois,Coufourier, Sébastien,Gandon, Vincent,Hoarau, Christophe,Jacquin-Labarre, Aurélien,Journot, Guillaume,Le Foll, Alexandra,Levacher, Vincent,Tamion, Rodolphe
supporting information
p. 767 - 773
(2020/03/25)

Enantioselective Reformatsky Reaction of Ketones Catalyzed by Chiral Indolinylmethanol
A reliable and practical Reformatsky reaction of ethyl iodide acetate with ketones for the synthesis of chiral β-hydroxyl carbonyl compounds in good yields and excellent enantioselectivities is presented. A readily available dihydroindole derivative was u
Luo, Renshi,Chen, Miao-Miao,Ouyang, Lu,Chan, Albert S. C.,Lu, Gui
supporting information
p. 4805 - 4811
(2020/07/14)

Organocatalyzed regioselective and enantioselective synthesis of 1,4- and 1,2-dihydropyridines
Herein, we introduce one of the first examples of asymmetric organocatalyzed synthesis of 1,2-dihydropyridines, affording enantioselective access to and partially solving regioselectivity challenges in the synthesis of dihydropyridines. We demonstrate that through modification of organocatalysts both 1,2- and 1,4-dihydropyridines (1,2- and 1,4-DHPs) can be obtained with high regioselectivity (ratio of 1,2-DHP/1,4-DHP from 95/5 to 0/100) and enantioselectivity (33% ee for 1,2-DHPs and up to 98% ee for 1,4-DHPs) in good yields (up to 87%).
Le, Truong-Giang,Pham, Hoai-Thu,Martin, James P.,Chataigner, Isabelle,Renaud, Jean-Luc
supporting information
p. 2673 - 2684
(2020/08/07)

Design and synthesis of novel indoline-(thio)urea hybrids
A series of novel indoline-(thio)urea were designed and prepared using indoline(s) as a new platform and tested as organocatalysts in the Michael and Morita–Baylis–Hillman reactions. Most of the compounds were found to be very active catalysts although they did not promote the enantioselectivity. As agents for the conversion of thiocarbonyl compounds into carbonyl compounds, potentials of PIFA and DDQ were also displayed. Furthermore, DFT calculations rationalized the experimentally observed non-enantioselectivity of the catalysts.
Lafzi, Ferruh,Kilic, Haydar,Tanriver, Gamze,Avc?, ?yküm Naz,Catak, Saron,Saracoglu, Nurullah
supporting information
p. 3510 - 3527
(2019/11/14)

GRANZYME B DIRECTED IMAGING AND THERAPY
Provided herein are heterocyclic compounds useful for imaging Granzyme B. Methods of imaging Granzyme B, combination therapies, and kits comprising the Granzyme B imaging agents are also provided.
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(2019/09/04)

Synthesis and evaluation of spumigin analogues library with thrombin inhibitory activity
Spumigins are marine natural products derived from cyanobacteria Nodularia spumigena, which mimics the structure of the D-Phe-Pro-Arg sequence and is crucial for binding to the active site of serine proteases thrombin and factor Xa. Biological evaluation of spumigins showed that spumigins with a (2S,4S)-4-methylproline central core represent potential lead compounds for the development of a new structural type of direct thrombin inhibitors. Herein, we represent synthesis and thrombin inhibitory activity of a focused library of spumigins analogues with indoline ring or L-proline as a central core. Novel compounds show additional insight into the structure and biological effects of spumigins. The most active analogue was found to be a derivative containing L-proline central core with low micromolar thrombin inhibitory activity.
?ula, Ale?,B?dziak, Izabela,Kikelj, Danijel,Ila?, Janez
(2018/11/23)

Kinetic Resolution of 2-Substituted Indolines by N-Sulfonylation using an Atropisomeric 4-DMAP-N-oxide Organocatalyst
The first catalytic kinetic resolution by N-sulfonylation is described. 2-Substituted indolines are resolved (s=2.6–19) using an atropisomeric 4-dimethylaminopyridine-N-oxide (4-DMAP-N-oxide) organocatalyst. Use of 2-isopropyl-4-nitrophenylsulfonyl chloride is critical to the stereodiscrimination and enables facile deprotection of the sulfonamide products with thioglycolic acid. A qualitative model that accounts for the stereodiscrimination is proposed.
Murray, James I.,Flodén, Nils J.,Bauer, Adriano,Fessner, Nico D.,Dunklemann, Daniel L.,Bob-Egbe, Opetoritse,Rzepa, Henry S.,Bürgi, Thomas,Richardson, Jeffery,Spivey, Alan C.
supporting information
p. 5760 - 5764
(2017/05/12)

Palladium-Catalyzed Enantioselective Heteroannulation of 1,3-Dienes by Functionally Substituted Aryl Iodides
The first enantioselective heteroannulation of 1,3-dienes by 2-iodoanilines and 2-iodobenzylic alcohols is described. The application of a BINOL-derived phosphoramidite ligand bearing electron-withdrawing substituents is the key to obtaining high enantios
Chen, Shu-Sen,Meng, Jing,Li, Yu-Hui,Han, Zhi-Yong
supporting information
p. 9402 - 9408
(2016/10/14)

Aldolase-catalyzed synthesis of conformationally constrained iminocyclitols: Preparation of polyhydroxylated benzopyrrolizidines and cyclohexapyrrolizidines
A straightforward chemo-enzymatic synthesis of new polyhydroxylated benzopyrrolizidines and cyclohexapyrrolizidines is developed. The two-step strategy consists of l-fuculose-1-phosphate aldolase variant F131A-catalyzed aldol addition of dihydroxyacetone phosphate to rac-N-benzyloxycarbonylindoline- 2-carbaldehyde as well as (2S*,3aS*,7aS*)- and (2S*,3aR*,7aR*)-N-benzyloxycarbonyloctahydroindole-2- carbaldehydes and a subsequent one-step catalytic deprotection-reductive amination.
Laborda, Pedro,Sayago, Francisco J.,Cativiela, Carlos,Parella, Teodor,Joglar, Jesus,Clapes, Pere
supporting information
p. 1422 - 1425
(2014/04/03)

Synthesis of indolines via Pd(II)-catalyzed amination of C-H bonds using PhI(OAc)2 as the bystanding oxidant
The Pd(II)-catalyzed intramolecular C-H amination of 2-pyridinesulfonyl- protected phenethylamine derivatives has been achieved using PhI(OAc) 2 as a bystanding oxidant, providing access to a variety of substituted indoline derivatives in good yields. The use of the 2-pyridinesulfonyl protecting group allows for facile deprotection following C-H functionalization.
Mei, Tian-Sheng,Leow, Dasheng,Xiao, Han,Laforteza, Brian N.,Yu, Jin-Quan
supporting information
p. 3058 - 3061
(2013/07/26)

Ring expansion of cyclic β-amino alcohols induced by diethylaminosulfur trifluoride: Synthesis of cyclic amines with a tertiary fluorine at C3
As the replacement of a hydrogen atom by a fluorine atom in a compound can have an important impact on its biological properties, the development of methods allowing the introduction of a fluorine atom is of great importance. The scope and limitations of
Anxionnat, Bruno,Robert, Benoit,George, Pascal,Ricci, Gino,Perrin, Marc-Antoine,Gomez Pardo, Domingo,Cossy, Janine
experimental part
p. 6087 - 6099
(2012/09/11)

Stereoselective synthesis of optically active cyclic α- And β-amino esters through lipase-catalyzed transesterification or interesterification processes
A series of cyclic α- and β-amino esters belonging to a family of indolines and quinolines have been efficiently synthesized to study their behavior in lipase-mediated kinetic resolution reactions. The influence of the fused ring structure to the benzene ring and the position of the ester functionality relative to the amino group have been demonstrated, finding excellent values of enantiodiscrimination in the transesterification reaction of methyl indoline-3-carboxylate with n-butanol catalyzed by Candida antarctica lipase B being observed. On the other hand, low to moderate selectivities have been found when using a wide panel of lipases toward methyl indoline-2- carboxylate or 1,2,3,4-tetrahydroquinoline derivatives in alkoxycarbonylation, transesterification or interesterification reactions.
Alatorre-Santamaria, Sergio,Gotor-Fernandez, Vicente,Gotor, Vicente
experimental part
p. 2307 - 2313
(2010/11/05)

Highly efficient asymmetric michael reaction of aldehydes to nitroalkenes with diphenylperhydroindolinol silyl ethers as organocatalysts
New dihydroindole and perhydroindole derivatives were synthesized in good yields and evaluated as chiral catalysts in the asymmetric Michael reaction of aldehydes to nitroalkenes. (2S,3aS,7aS)Diphenylperhydroindolinol silyl ether 10 facilitated the reacti
Luo, Ren-Shi,Weng, Jiang,Ai, Hui-Bing,Lu, Gui,Chan, Albert S. C.
supporting information; experimental part
p. 2449 - 2459
(2009/12/27)

Efficient access to enantiomerically pure cyclic α-amino esters through a lipase-catalyzed kinetic resolution
A series of α-amino acid derivatives containing the 2,3-dihydroindole or octahydroindole core have been chemoenzymatically synthesized in good overall yields and high enantiomeric purity under mild reaction conditions using lipases for the introduction of chirality. Candida antarctica lipase type A has shown excellent activity and high enantiodiscrimination ability toward the two cyclic amino esters used as substrates. The selectivity of the process proved to be greatly dependent on the alkoxycarbonylating agent. Thus, the enzymatic kinetic resolution of methyl indoline-2-carboxylate has been successfully achieved using 3-methoxyphenyl allyl carbonate, whereas (2R,3aR,7aR)-benzyl octahydroindole-2-carboxylate required the less reactive diallyl carbonate.
Alatorre-Santamaria, Sergio,Rodriguez-Mata, Maria,Gotor-Fernandez, Vicente,de Mattos, Marcos Carlos,Sayago, Francisco J.,Jimenez, Ana I.,Cativiela, Carlos,Gotor, Vicente
p. 1714 - 1719
(2008/12/20)

Synthesis and pharmacological evaluation of pentacyclic 6a,7-dihydrodiindole and 2,3-dihydrodiindole derivatives as novel melatoninergic ligands
The synthesis of novel melatonin analogues 3a and 4a-c designed as melatonin receptor ligands is described. Among the newly synthesized ligands, 2-((S)-2-hydroxymethylindolin-1-ylmethyl)-melatonin 4b displayed the highest affinity for MT1 recep
Attia, Mohamed I.,Witt-Enderby, Paula A.,Julius, Justin
p. 7654 - 7661
(2008/12/23)

Substituted Sulfonamide Compounds
Substituted sulfonamide compounds with bradykinin receptor (B1R) modulating activity; processes for the preparation thereof, pharmaceutical compositions comprising such compounds, and methods of using such compounds to treat or inhibit pain and/or other disorders and/or disease states.
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(2008/12/08)

Substituted Sulfonamide Compounds
Substituted sulfonamide compounds corresponding to formula I pharmaceutical compositions comprising them, a process for preparing them, and the use of such compounds to treat or inhibit pain and other disorders or disease states.
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Page/Page column 38-39

(2009/01/24)

Fused bicyclic carboxamide derivatives and methods of their use
Fused bicyclic carboxamide derivatives are disclosed. Pharmaceutical compositions containing the compounds and methods for their use are also disclosed.
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Page/Page column 48

(2010/02/11)

METHOD FOR PREPARING (S)-INDOLINE-2-CARBOXYLIC ACID AND (S)-INDOLINE-2-CARBOXYLIC ACID METHYL ESTER USING HYDROLYTIC ENZYME
Disclosed is a method for preparing (S)-indoline-2-carboxylic acid and (S)-indoline-2-carboxylic acid methyl ester using an inexpensive industrially available enzyme capable of assuring superior optical purity and yield. At this time, the hydrolytic enzyme is selected from the group consisting of Savinase, Alcalase, Novozym 243, Everlase, Esperase, Protease 7 and Acylase, whereby (S)-indoline-2-carboxylic acid and methyl ester thereof having an optical purity of at least 99%e.e. can be obtained through a simplified preparation process, thus generating economic benefits.
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(2008/06/13)

Synthesis and pharmacological evaluation of Tic-hydantoin derivatives as selective σ1 ligands. Part 1
Herein is described a new class of selective σ1 ligands consisting of tetrahydroisoquinoline-hydantoin (Tic-hydantoin) derivatives. Compound 3a has high affinity (IC50 = 16 nM) for the σ1 receptor and is selective in a large panel of therapeutic targets. This first study presents structural changes around the Tic-hydantoin core, leading to a Tic-hydantoin analogue with a higher σ1 affinity (IC50 ≈ 1 nM).
Charton, Julie,Gassiot, Amaury Cazenave,Girault-Mizzi, Sophie,Debreu-Fontaine, Marie-Ange,Melnyk, Patricia,Sergheraert, Christian
p. 4833 - 4837
(2007/10/03)

Stereospecific synthesis of 2,2,3-trisubstituted tetrahydroquinolines: Application to the total syntheses of benzastatin E and natural virantmycin
An efficient methodology for the synthesis of 2,2,3-trisubstituted tetrahydroquinolines has been developed, which involves the triphenylphosphine- CCl4-mediated stereospecific rearrangement of α,α- disubstituted indoline-2-methanols 15 to 2,2,3-trisubstituted tetrahydroquinolines 26. The rearrangement precursors 15 are readily prepared by the diastereoselective Grignard addition to 2-acylindolines 13. The total syntheses of (+)-benzastatin E (1) and natural virantmycin (2a) were accomplished utilizing this methodology. This rearrangement reaction might afford some chemical precedent for the biogenetic pathway of the benzastatin family.
Ori, Mayuko,Toda, Narihiro,Takami, Kazuko,Tago, Keiko,Kogen, Hiroshi
p. 2075 - 2104
(2007/10/03)

The effects of conformational constraints and steric bulk in the amino acid moiety of philanthotoxins on AMPAR antagonism
Philanthotoxin-343 (PhTX-343), a synthetic analogue of wasp toxin PhTX-433, is a noncompetitive antagonist at ionotropic receptors (e.g., AChR or iGluR). To determine possible effects of variations of the amino acid side chain, a library consisting of seventeen PhTX-343 analogues was prepared. Thus, tyrosine was replaced by either apolar, conformationally constrained, or bulky amino acids, whereas the acyl unit and the polyamine moiety were kept unchanged. Analogues with tertiary amide groups were prepared for the first time. Pentafluorophenyl esters were employed for amide bond formation, establishing general protocols for philanthotoxin solution- and solid-phase synthesis (39-90% and 42-54% overall yields, respectively). The analogues were tested for their ability to antagonize kainate-induced currents of 2-amino-3-(3-hydroxy-5-methyl- 4-isoxazoyl)propanoic acid receptors (AMPAR) expressed in Xenopus oocytes from rat brain mRNA. This showed that steric bulk in the amino acid moiety is well tolerated and suggests that binding to AMPAR does not involve the α-NHCO group as a donor in hydrogen bonding.
J?rgensen, Malene R.,Olsen, Christian A.,Mellor, Ian R.,Usherwood, Peter N. R.,Witt, Matthias,Franzyk, Henrik,Jaroszewski, Jerzy W.
p. 56 - 70
(2007/10/03)

Dual enantioselective Diels-Alder process in the cyclization of chiral acrylamide with dienes
Diels-Alder cycloadditions of chiral acrylamides with cyclopentadiene or 2, 3-dimethyl butadiene proceed with high diastereofacial selectivity. Either endo-R or endo-S products have been obtained depending upon the structures of acrylamides and Lewis acids used. The endo form was exclusively obtained over the exo form. The dependence of the mechanism of formation of opposite configurations of endo-R or endo-S products on the Lewis acids is discussed. Copyright 2004 John Wiley & Sons, Ltd.
Jung, Doo Young,Park, Doo Han,Kim, Sung Han,Kim, Yong Hae
p. 1017 - 1022
(2007/10/03)

Chiral aminophosphine-oxazoline auxiliaries applied to copper-catalysed enantioselective 1,4-additions to enones
A series of chiral aminophosphine-oxazoline auxiliaries has been prepared and applied in the copper-catalysed 1,4-addition of diethylzinc to enones. The addition products are obtained quantitatively in up to 67% ee. The most efficient ligand of the series is based on L-indoline carboxylic acid and L-valinol.
Blanc, Catherine,Agbossou-Niedercorn, Francine
p. 757 - 761
(2007/10/03)

Cardioselective anti-ischemic ATP-sensitive potassium channel (KATP) openers: Benzopyranyl indoline and indole analogues
This paper describes the design, syntheses, and biological evaluations of novel ATP-sensitive potassium channel (KATP) openers, benzopyranyl indoline and indole derivatives. Among those, two enantiomers of indoline-2-carboxylic ethyl esters (14, 18) showed the best cardioprotective activities both in vitro and in vivo, while their vasorelaxation potencies were very low (concentration for 50% inhibition of vasorelaxation >30 μM). The cardioprotective effect of 14 was completely reversed by 5-hydroxydecanoate, a selective mitochondrial KATP blocker, indicating its provable protective mechanism through the mitochondrial KATP opening. In addition, we performed conformational analyses using 2D-NMR, X-ray crystallography and molecular modeling to study the structure-activity relationships in this series of compounds.
Lee, Sunkyung,Yi, Kyu Yang,Kim, Soo-Kyung,Suh, Jeehee,Kim, Nak Jeong,Yoo, Sung-Eun,Lee, Byung Ho,Seo, Ho Won,Kim, Sun-Ok,Lim, Hong
p. 459 - 471
(2007/10/03)

Total synthesis of (+)-benzastatin E via diastereoselective Grignard addition to 2-acylindoline.
[reaction: see text] A stereoselective total synthesis of (+)-benzastatin E (1) is described. The synthesis involves a diastereoselective Grignard addition to 2-acylindoline 2, which is derived from commercially available (S)-2-indolinecarboxylic acid (3). The unknown absolute configuration of (+)-1 is determined as (9S,10R).
Toda, Narihiro,Ori, Mayuko,Takami, Kazuko,Tago, Keiko,Kogen, Hiroshi
p. 269 - 271
(2007/10/03)

Design, synthesis, and tripeptidyl peptidase II inhibitory activity of a novel series of (S)-2,3-dihydro-2-(4-alkyl-1H-imidazol-2-yl)-1H-indoles
Butabindide, 1, was previously reported as a potent inhibitor (IC50 = 7 nM) of the serine protease enzyme tripeptidyl peptidase II (TPPII), an endogenous protease that degrades cholecystokinin-8 (CCK-8). We found that 1 has some inherent chemical instability, yielding diketopiperazine 2 fairly readily under mimicked physiological conditions. We therefore prepared imidazoles 3, which are void of 1's inherent instability, and have found that our novel analogues maintained comparable TPPII inhibitory activity (e.g., for 3c, IC50 = 4 nM) as 1.
Breslin, Henry J.,Miskowski, Tamara A.,Kukla, Michael J.,Leister, William H.,De Winter, Hans L.,Gauthier, Diane A.,Somers, Maria V. F.,Peeters, Dani?lle C. G.,Roevens, Peter W. M.
p. 5303 - 5310
(2007/10/03)

Tripeptidylpeptidase inhibitors
A compound of formula wherein the substituents are defined as in the specification and salts or hydrates thereof is disclosed as well as a method of treating disorders associated with the inactivation or excessive degradation of cholecystokinin.
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(2008/06/13)

Benzimidazoles/Imidazoles Linked to a Fibrinogen Receptor Antagonist Template Having Vitronectin Receptor Antagonist Activity
Vitronectin receptor antagonists having the formula: STR1 which are useful for the treatment of inflammation, cancer and cardiovascular disorders, such as atherosclerosis and restenosis, and diseases wherein bone resorption is a factor, such as osteoporsis.
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(2008/06/13)

HETEROCYCLIC BETA-ADRENERGIC AGONISTS
The present invention relates to certain compounds of the formula (I) the racemic-enantiomeric mixtures and optical isomers of said compounds and the pharmaceutically acceptable salts or prodrugs thereof, depicted below, which are β-adrenergic receptor agonists and accordingly have utility as, inter alia, hypoglycemic and antiobesity agents. More specifically, the compounds of the instant invention are selective agonists of β 3-adrenergic receptor. The invention also relates to methods of use for the compounds and to pharmaceutical compositions containing them. The compounds of the present invention also possess utility for increasing lean meat deposition and/or improving the lean meat to fat ratio in animals, e.g., ungulate animals, companion animals and poultry. The compounds have the formula STR1 wherein R. sup.1, R. sup.2, R 3, R 4, R 5, Y and Z are as defined in the specification.
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(2008/06/13)

On the origins of enantioselectivity in oxazaborolidine mediated carbonyl reductions
A series of tricyclic oxazaborolidine catalysts have been prepared from readily available (S)-indoline-2-carboxylic acid. In each case, an arene chromium(0) carbonyl group was introduced on one face of the catalyst. Results obtained in the borane mediated
Jones, Graham B.,Heaton, Steven B.,Chapman, Brant J.,Guzel, Mustafa
p. 3625 - 3636
(2007/10/03)

Tricyclic [6.5.51]-fused oxazolidinone antibacterial agents
The present invention involves tricyclic-fused 6-member ring oxazolidinones STR1 and tricyclic-fused 5-member ring oxazolidinones STR2 which are useful as antibacterial agents.
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(2008/06/13)

ENANTIOSELECTIVE CATALYTIC BORANE REDUCTIONS OF ACHIRAL KETONES: SYNTHESES AND APPLICATION OF TWO CHIRAL β-AMINO ALCOHOLS FROM (S)-2-INDOLINE CARBOXYLIC ACID
The synthesis of (S)-α,α-diphenyl-(indolin-2-yl)methanol 1 makes available the chiral oxazaborolidine 2 which is an excellent catalyst for borane reduction of prochiral ketones to chiral secondary alcohols, e.g. acetophenone, in high optical purity.The ne
Martens, Juergen,Dauelsberg, Ch.,Behnen, W.,Wallbaum, S.
p. 347 - 350
(2007/10/02)

SYNTHETIC APPROACHES TO BREVIANAMIDES A AND B I. PREPARATION OF 4-p-METHOXYBENZYL-5-(1'-CARBOMETHOXY-2'-METHYLIDENE)-1,2-L-PYROLIDINOPIPERAZINE-3,6-DIONE VIA AN IRELAND ESTER ENOLATE CLAISEN REARRANGEMENT.
Using an ester enolate Claisen rearrangement to prepare 1-carbomethoxy-2-(1',1'-dimethylallyl)-2,3-dihydroindole-2-carboxylic acid followed by condensation with N-p-methoxybenzyl-glycyl-L-proline anhydride gave the title compound, a key intermediate in a synthetic approach to brevianamides A and B.
Dunkerton, Lois V.,Chen, Hao,McKillican, Bruce P.
p. 2539 - 2542
(2007/10/02)

MAGNESIUM-METHANOL AS A SIMPLE CONVENIENT REDUCING AGENT FOR Α,Β-UNSATURATED ESTERS
Various α,β-unsaturated esters undergo double bond reduction by magnesium in methanol to give the corresponding saturated ones in almost quantitative yields.
Youn, In Kwon,Yon, Gyu Hwan,Pak, Chwang Siek
p. 2409 - 2410
(2007/10/02)