- POTENT HUMAN NEURONAL NITRIC OXIDE SYNTHASE INHIBITORS
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Disclosed are 2-aminopyridine derivative compounds for use as inhibitors of nitric oxide synthase (NOS). In particular, the field of the invention relates to 2-aminopyridine derivative compounds for use as inhibitors of neuronal nitric oxide synthase (nNOS), which are formulated as pharmaceutical compositions for treating diseases and disorders associated with nNOS such as Alzheimer's, Parkinson's, and Huntington's diseases, and amytrophic lateral sclerosis, cerebral palsy, stroke/ischemic brain damage, and migraine headaches.
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Paragraph 00340-00342
(2021/09/04)
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- From Oxadiazole to Triazole Analogues: Optimization toward a Dual Orexin Receptor Antagonist with Improved in vivo Efficacy in Dogs
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The orexin system is responsible for regulating the sleep-wake cycle. Suvorexant, a dual orexin receptor antagonist (DORA) is approved by the FDA for the treatment of insomnia disorders. Herein, we report the optimization efforts toward a DORA, where our starting point was (5-methoxy-4-methyl-2-[1,2,3]triazol-2-yl-phenyl)-{(S)-2-[5-(2-trifluoromethoxy-phenyl)-[1,2,4]oxadiazol-3-yl]-pyrrolidin-1-yl}methanone (6), a compound which emerged from our in-house research program. Compound 6 was shown to be a potent, brain-penetrating DORA with in vivo efficacy similar to suvorexant in rats. However, shortcomings from low metabolic stability, high plasma protein binding (PPB), low brain free fraction (fu brain), and low aqueous solubility, were identified and hence, compound 6 was not an ideal candidate for further development. Our optimization efforts addressing the above-mentioned shortcomings resulted in the identification of (4-chloro-2-[1,2,3]triazol-2-yl-phenyl)-{(S)-2-methyl-2-[5-(2-trifluoromethoxy-phenyl)-4H-[1,2,4]triazol-3-yl]-pyrrolidin-1-yl}l-methanone (42), a DORA with improved in vivo efficacy compared to 6.
- Bolli, Martin H.,Boss, Christoph,Brotschi, Christine,Gatfield, John,Heidmann, Bibia,Jenck, Francois,Roch, Catherine,Sifferlen, Thierry,Treiber, Alexander,Williams, Jodi T.
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- Optimization of Blood-Brain Barrier Permeability with Potent and Selective Human Neuronal Nitric Oxide Synthase Inhibitors Having a 2-Aminopyridine Scaffold
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Effective delivery of therapeutic drugs into the human brain is one of the most challenging tasks in central nervous system drug development because of the blood-brain barrier (BBB). To overcome the BBB, both passive permeability and efflux transporter liability of a compound must be addressed. Herein, we report our optimization related to BBB penetration of neuronal nitric oxide synthase (nNOS) inhibitors toward the development of new drugs for neurodegenerative diseases. Various approaches, including enhancing lipophilicity and rigidity of new inhibitors and modulating the pKa of amino groups, have been employed. In addition to determining inhibitor potency and selectivity, crystal structures of most newly designed compounds complexed to various nitric oxide synthase isoforms have been determined. We have discovered a new analogue (21), which exhibits not only excellent potency (Ki 30 nM) in nNOS inhibition but also a significantly low P-glycoprotein and breast-cancer-resistant protein substrate liability as indicated by an efflux ratio of 0.8 in the Caco-2 bidirectional assay.
- Do, Ha T.,Li, Huiying,Chreifi, Georges,Poulos, Thomas L.,Silverman, Richard B.
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supporting information
p. 2690 - 2707
(2019/03/11)
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- Synthesis and thermo-responsive behavior of helical polyacetylenes derived from proline
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A series of optically active helical poly[(S)-2-ethynyl-N-aliphatic acylpyrrolidine] were efficiently synthesized from a commercially available biomass-based starting material, and that bearing a short propionyl substituent exhibited an unexpected lower critical solution temperature in an aqueous solution with a narrow phase-transition window and a small hysteresis.
- Shi, Ge,Wang, Sheng,Guan, Xiaoyan,Zhang, Jie,Wan, Xinhua
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supporting information
p. 12081 - 12084
(2018/11/21)
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- Series of Alkynyl-Substituted Thienopyrimidines as Inhibitors of Protozoan Parasite Proliferation
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Discovery of new chemotherapeutic lead agents can be accelerated by optimizing chemotypes proven to be effective in other diseases to act against parasites. One such medicinal chemistry campaign has focused on optimizing the anilinoquinazoline drug lapatinib (1) and the alkynyl thieno[3,2-d]pyrimidine hit GW837016X (NEU-391, 3) into leads for antitrypanosome drugs. We now report the structure-activity relationship studies of 3 and its analogs against Trypanosoma brucei, which causes human African trypanosomiasis (HAT). The series was also tested against Trypanosoma cruzi, Leishmania major, and Plasmodium falciparum. In each case, potent antiparasitic hits with acceptable toxicity margins over mammalian HepG2 and NIH3T3 cell lines were identified. In a mouse model of HAT, 3 extended life of treated mice by 50%, compared to untreated controls. At the cellular level, 3 inhibited mitosis and cytokinesis in T. brucei. Thus, the alkynylthieno[3,2-d]pyrimidine chemotype is an advanced hit worthy of further optimization as a potential chemotherapeutic agent for HAT.
- Woodring, Jennifer L.,Behera, Ranjan,Sharma, Amrita,Wiedeman, Justin,Patel, Gautam,Singh, Baljinder,Guyett, Paul,Amata, Emanuele,Erath, Jessey,Roncal, Norma,Penn, Erica,Leed, Susan E.,Rodriguez, Ana,Sciotti, Richard J.,Mensa-Wilmot, Kojo,Pollastri, Michael P.
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supporting information
p. 996 - 1001
(2018/09/21)
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- PYRROLOBENZODIAZEPINE ANTIBODY DRUG CONJUGATES AND METHODS OF USE
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The invention provides antibody-drug conjugates comprising an antibody conjugated to a pyrrolobenzodiazepine drug moiety via a disulfide linker, pyrrolobenzodiazepine linker-drug intermediates, and methods of using the antibody-drug conjugates.
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Paragraph 0581; 0583; 0688; 0691
(2017/04/23)
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- The design of 8-hydroxyquinoline tetracyclic lactams as HIV-1 integrase strand transfer inhibitors
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A novel series of HIV-1 integrase strand transfer inhibitors were designed using the venerable two-metal binding pharmacophore model and incorporating structural elements from two different literature scaffolds. This manuscript describes a number of 8-hyd
- Velthuisen, Emile J.,Johns, Brian A.,Temelkoff, David P.,Brown, Kevin W.,Danehower, Susan C.
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- As cell necrosis inhibitors of the indole compounds (by machine translation)
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The invention relates to chemical formula (1) indole compounds, or its pharmaceutically acceptable salt or isomer, and in containing the same as the characteristic, as an active ingredient for the prevention or treatment of cell necrosis and its associated disease composition and method of manufacturing. (by machine translation)
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Paragraph 0223; 0224; 0225; 0226; 0227
(2016/10/09)
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- INDOLE COMPOUND AS INHIBITOR OF NECROSIS
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The present invention relates to an indole compound represented by formula (1), a pharmaceutically acceptable salt or isomer thereof, a composition for prevention or treatment of necrosis and necrosis-associated diseases, and a method for preparing the composition, the composition comprising the indole compound or the pharmaceutically acceptable salt or isomer thereof as an active ingredient.
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-
Paragraph 0191; 0192; 0193; 0194; 0195
(2016/08/17)
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- 1,2,3-Triazole Stabilized Neurotensin-Based Radiopeptidomimetics for Improved Tumor Targeting
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Neurotensin (NT) is a regulatory peptide with nanomolar affinity toward NT receptors, which are overexpressed by different clinically relevant tumors. Its binding sequence, NT(8-13), represents a promising vector for the development of peptidic radiotracers for tumor imaging and therapy. The main drawback of the peptide is its short biological half-life due to rapid proteolysis in vivo. Herein, we present an innovative strategy for the stabilization of peptides using nonhydrolizable 1,4-disubstituted, 1,2,3-triazoles as amide bond surrogates. A triazole scan?of the peptide sequence yielded novel NT(8-13) analogues with enhanced stability, retained receptor affinity, and improved tumor targeting properties in vivo. The synthesis of libraries of triazole-based peptidomimetics was achieved efficiently on solid support by a combination of Fmoc-peptide chemistry, diazo transfer reactions, and the Cu(I)-catalyzed alkyne azide cycloaddition (CuAAC) employing methods that are fully compatible with standard solid phase peptide synthesis (SPPS) chemistry. Thus, the amide-to-triazole substitution strategy may represent a general methodology for the metabolic stabilization of biologically active peptides.
- Mascarin, Alba,Valverde, Ibai E.,Vomstein, Sandra,Mindt, Thomas L.
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p. 2143 - 2152
(2015/11/09)
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- OREXIN RECEPTOR ANTAGONISTS WHICH ARE [ORTHO BI (HETERO )ARYL]-[2-(META BI (HETERO )ARYL)-PYRROLIDIN-1-YL]-METHANONE DERIVATIVES
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The present invention relates to [ortho bi-(hetero-)aryl]-[2-(meta bi-(hetero-)aryl)-pyrrolidin-1-yl]- methanone derivatives of formula (I) wherein R, and the rings A1 A2 and A3 are as described in the description, to pharmaceutically acceptable salts thereof, to their preparation, to pharmaceutical compositions containing one or more compounds of formula (I), and to their use as pharmaceuticals, especially to their use as orexin receptor antagonists.
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Page/Page column 120
(2014/05/07)
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- In situ generation of the Ohira-Bestmann reagent from stable sulfonyl azide: Scalable synthesis of alkynes from aldehydes
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We report an improved method for in situ generation of the Ohira-Bestmann reagent. Using the recently reported bench-stable imidazole-1-sulfonyl azide as diazotransfer reagent, this new method represents a scalable and convenient approach for the transformation of aldehydes into terminal alkynes. The method features an easier workup compared to the existing in situ protocol due to increased aqueous solubility of waste products.
- Jepsen, Tue Heesgaard,Kristensen, Jesper Langgaard
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p. 9423 - 9426
(2015/02/19)
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- Gold-catalyzed oxycyclization of allenic carbamates: Expeditious synthesis of 1,3-oxazin-2-ones
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A combined experimental and computational study on regioselective gold-catalyzed synthetic routes to 1,3-oxazinan-2-ones (kinetically controlled products) and 1,3-oxazin-2-one derivatives (thermodynamically favored) from easily accessible allenic carbamates has been carried out.
- Alcaide, Benito,Almendros, Pedro,Quiros, M. Teresa,Fernandez, Israel
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p. 818 - 826
(2013/06/05)
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- NOVEL HEPATITIS C VIRUS INHIBITORS
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The invention provides compounds of formula (I): wherein Rings A and A' are independently 5-membered optionally substituted aromatic heterocycles; Q is C(=O)NR1R1' or formula U is C(R4)2, O, S, S(=O)2, C(R4)2C(R4)2, CH2O, OCH2, CH2S, SCH2, CH2S(=O)2, S(=O)CH2 or C=C(Ru )2; X is CH2, CHR12, CR12R12, O, S, S(=O)2 or NRx; m is 0, 1, 2 or 3; n is 0, 1, 2 or 3; the other variables are as defined in the claims, which are of use in the treatment or prophylaxis of hepatitis C virus infection, and related aspects.
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Page/Page column 41; 42
(2013/07/05)
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- Total synthesis of (+)-antofine and (-)-cryptopleurine
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The tylophorine alkaloid anticancer compounds antofine and cryptopleurine have been synthesized in optically active form. Both syntheses use optically pure α-amino acids as the starting materials, require only seven steps from known 2-ethynylpyrrolidine or 2-ethynylpiperidine derivatives, and are free of protecting groups. The key steps include an alkyne hydration and a chromium-carbene-complex-based net [5 + 5]-cycloaddition step. The alkyne hydration was accompanied by racemization of the β-amino ketone product under most of the conditions examined, and minimization of this side-reaction was achieved through careful pH control and choice of metal additive. The final ring closure involved a Bischler-Napieralski reaction using a carbamate (antofine) or urea (cryptopleurine) precursor. Single enantiomers of the tylophorine alkaloids antofine and cryptopleurine have been prepared by using a short synthesis that involves regioselective alkyne hydration of a chiral propargylic amide, Fischer carbene complex mediated net [5+5] cycloaddition, and urea-based Friedel-Crafts acylation as key steps. Copyright
- Ying, Weijiang,Herndon, James W.
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supporting information
p. 3112 - 3122
(2013/06/26)
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- Braces for the peptide backbone: Insights into structure-activity relationships of protease inhibitor mimics with locked amide conformations
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Flower power: Potent protease inhibitors containing triazolyl mimics of cis and trans backbone amides were engineered based on the structure of the sunflower trypsin inhibitor 1. The biologically relevant cis-Pro motif was successfully replaced with a non
- Tischler, Marco,Nasu, Daichi,Empting, Martin,Schmelz, Stefan,Heinz, Dirk W.,Rottmann, Philipp,Kolmar, Harald,Buntkowsky, Gerd,Tietze, Daniel,Avrutina, Olga
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supporting information; experimental part
p. 3708 - 3712
(2012/06/05)
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- Proline-derived aminotriazole ligands: Preparation and use in the ruthenium-catalyzed asymmetric transfer hydrogenation
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The preparation of 2-triazolyl- and 2-triazolylmethylpyrrolidines from L-proline and L-trans-4-hydroxyproline is described, along with their evaluation as chiral ligands in ruthenium-catalyzed asymmetric transfer hydrogenation. Modular evolution of the ligands by introduction of remote substituents is also presented, showing a surprisingly important effect on the performance of the ligands.
- Cambeiro, Xacobe C.,Pericas, Miquel A.
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supporting information; experimental part
p. 113 - 124
(2011/04/12)
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- The preparation of (-)-grandisine B from (+)-grandisine D; A biomimetic total synthesis or formation of an isolation artefact?
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An efficient new alkyne-acetal cyclization procedure has been developed to prepare enantiopure indolizidine building blocks from l-proline and then applied to prepare the Elaeocarpus-derived alkaloids grandisine B and grandisine D in an efficient manner.
- Cuthbertson, James D.,Godfrey, Andrew A.,Taylor, Richard J. K.
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supporting information; scheme or table
p. 3976 - 3979
(2011/10/09)
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- AZAINDOLE INHIBITORS OF IAP
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The invention provides novel inhibitors of IAP that are useful as therapeutic agents for treating malignancies where the compounds have the general formula I: I wherein X1, X2, Y, Z1, Z2, Z3, Z4, R1, R2, R3, R3', R4, R4', R5, R6, R6' and R9 are as described herein.
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Page/Page column 45-46
(2010/04/03)
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- The design of potent and selective inhibitors of DPP-4: Optimization of ADME properties by amide replacements
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For a series of β-homophenylalanine based inhibitors of dipeptidyl peptidase IV ADME properties were improved by the incorporation of amide replacements. These efforts led to a novel series of potent and selective inhibitors of DPP-4 that exhibit an attractive pharmacokinetic profile and show excellent efficacy in an animal model of diabetes.
- Nordhoff, Sonja,Bulat, Stephan,Cerezo-Galvez, Silvia,Hill, Oliver,Hoffmann-Enger, Barbara,Lopez-Canet, Meritxell,Rosenbaum, Claudia,Rummey, Christian,Thiemann, Meinolf,Matassa, Victor G.,Edwards, Paul J.,Feurer, Achim
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scheme or table
p. 6340 - 6345
(2010/06/11)
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- FUSED THIOPHENE DERIVATIVES AS KINASE INHIBITORS
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A series of 5,6-dihydro-1-benzothiophen-7(4H)-one derivatives, and analogues thereof, which are substituted in the 2-position by an optionally substituted morpholin-4-yl moiety, being selective inhibitors of PI3 kinase enzymes, are accordingly of benefit in medicine, for example in the treatment of inflammatory, autoimmune, cardiovascular, neurodegenerative, metabolic, oncological, nociceptive or ophthalmic conditions.
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Page/Page column 57
(2008/06/13)
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- Triazolopeptides: chirospecific synthesis and cis/trans prolyl ratios of structural isomers
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As cis/trans prolyl isomerization plays a crucial role in various biological processes, peptide mimics capable of modifying the cis/trans Xaa-Pro ratio are of particular interest. A practical approach toward proline derived triazolopeptides employing [3+2] azide-alkyne cycloadditions as the key reaction step and the analysis of their cis/trans prolyl ratios are reported. Structural investigations indicated the adjustability of both the cis-percentage and the conformational stability toward intramolecular H-bonding effects.
- Paul, Andreas,Bittermann, Holger,Gmeiner, Peter
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p. 8919 - 8927
(2007/10/03)
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- 4-(PYRID-2-YL) AMINO SUBSTITUTED PYRIMIDINE AS PROTEIN KINASE INHIBITORS
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A compound of formula (I): wherein the substituents are as defined in the text for use in inhibiting insulin-like growth factor 1 receptor activity in a warm-blooded animal such as man.
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Page/Page column 81; 84; 86; 88; 90-91
(2008/06/13)
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- A convenient scalable one-pot conversion of esters and Weinreb amides to terminal alkynes
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Esters and amides undergo reduction to the corresponding aldehydes using DIBAL-H followed by same pot conversion to terminal alkynes utilizing the Bestmann-Ohira reagent in good to excellent yields. Additionally chiral nonracemic substrates undergo this transformation with complete preservation of stereochemical integrity.
- Dickson, Hamilton D.,Smith, Stephon C.,Hinkle, Kevin W.
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p. 5597 - 5599
(2007/10/03)
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- Parallel synthesis of terminal alkynes using a ROMPgel-supported ethyl 1-diazo-2-oxopropylphosphonate
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ROMPgel-supported ethyl 1-diazo-2-oxopropylphosphonate has been prepared, and the supported reagent has been effectively employed in the conversion of a variety of aldehydes into terminal alkynes under mild reaction conditions. The influence of cross-link structure, comonomers, and polymer structure on reaction efficiency has been examined.
- Barrett, Anthony G. M.,Hopkins, Brian T.,Love, Andrew C.,Tedeschi, Livio
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p. 835 - 837
(2007/10/03)
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- Pharmaceutical compositions and methods for use
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The present invention relates to aryl olefinic azacyclic compounds and aryl acetylenic azacyclic compounds, including pyridyl olefinic cycloalkylamines and pyridyl acetylenic cycloalkylamines. The present invention also relates to prodrug derivatives of the compounds of the present invention.
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- Natural product derived inhibitors of lipoprotein associated phospholipase a2, synthesis and activity of analogues of sb-253514
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The synthesis of analogues of SB-253514, a novel natural product derived inhibitor of lipoprotein associated phospholipase A2 (Lp-PLA2), is described together with their ability to inhibit Lp-PLA2. (C) 2000 Elsevier Science Ltd.
- Pinto, Ivan L.,Boyd, Helen F.,Hickey, Deirdre M.B.
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p. 2015 - 2017
(2007/10/03)
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- Furopyridine, thienopyridine pyrrolopyridine useful in controlling chemical synaptic transmission
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Novel heterocyclic ether compounds having the formula: STR1 wherein A, m, R, X, Y1, Y2 and Y3 are specifically defined, which are useful in selectively controlling chemical synaptic transmission; therapeutically-effective pharmaceutical compositions thereof; and use of said compositions to selectively control synaptic transmission in mammals.
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- A short enantioselective access to pumiliotoxin 251D from L-proline
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The indolizidine framework of pumiliotoxin 251D with the appropriate functionalities for incorporation of the tertiary hydroxyl at the C-8 and the alkylidene side chain at C-6 has been accessed from L-proline by using a 6-exo-dig radical cyclization. - Keywords: pumiliotoxin 251D; L-proline; radical cyclization
- Cossy, Janine,Cases, Manuel,Pardo, Domingo Gomez
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p. 141 - 144
(2007/10/03)
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- A new stereoselective synthesis of chiral γ-functionalized (E)-allylic amines
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Chiral t-Boc protected propargylic amines have been obtained starting from aminoaldehydes derived from natural aminoacids. Stannylcupration of these substrates affords an easy regio- and stereocontrolled route to the corresponding γ-stannylated (E)-allylamines which are useful intermediates for the synthesis of the corresponding γ-functionalized allylic systems.
- Reginato, Gianna,Mordini, Alessandro,Messina, Flavia,Degl'Innocenti, Alessandro,Poli, Giovanni
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p. 10985 - 10996
(2007/10/03)
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- Synthesis and 11C-labelling of two selective high affinity nicotinic cholinergic agonists for evaluation as radioligands for PET studies
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ABT-418 ((S)-3-methyl-5-[1-methyl-2-pyrrolidinyl]isoxazole) and N-methylcytisine (N-methyl- 1,2,3,4,5,6-hexahydro-1,5-methano-8H-pyrido-[1,2-a][1,5]diazocin-8-one) are two high affinity nicotinic cholinergic agonists. ABT-418 was synthesized in 7 steps from commercially available (S)-Boc- proline in 35% overall yield. Methylation of commercial cytisine cleanly gave N-methyl-cytisine. ABT-418 and N-methylcytisine were labelled using [11C]methyl iodide by methylation of the corresponding nor-precursors for their in vivo evaluation as positron emission tomography (PET) probes of the nicotinic cholinergic receptors in baboon brain. As for [11C]nicotine, specific binding in vivo could not be demonstrated for ABT-418. Therefore, further experiments are needed to determine the full PET pharmacological profile and the subsequent potential clinical applications of ABT-418 as a tracer for PET experiments. For labelled N-methyl-cytisine, radioactivity in the cerebral cortex and in tile blood were similar. Thus, 11C-labelled N-methylcytisine does not appear to be a suitable ligand for mapping brain nAChR.
- Dolle, Frederic,Dolci, Lilian,Valette, Heric,Bottlaender, Michel,Fournier, Denis,Fuseau, Chantai,Vaufrey, Francoise,Crouzel, Christian
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p. 1099 - 1112
(2007/10/03)
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- Ligands for brain cholinergic channel receptors: Synthesis and in vitro characterization of novel isoxazoles and isothiazoles as bioisosteric replacements for the pyridine ring in nicotine
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Ligands which activate neuronal nicotinic acetylcholine receptors (nAChRs) represent a potential approach for the palliative treatment for the symptoms of memory loss associated with Alzheimer's disease (AD). Based upon this approach, a series of novel 3,
- Garvey,Wasicak,Elliott,Lebold,Hettinger,Carrera,Lin,He,Holladay,Anderson,Cadman,Raszkiewicz,Sullivan,Arneric
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p. 4455 - 4463
(2007/10/02)
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- 1-substituted-2-(3-amino-1-propynyl)pyrrolidine derivatives
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Compounds of the formula: STR1 pharmaceutical compositions containing the compounds and methods of using the compounds in the treatment of central cholinergic disfunction in a mammal are disclosed.
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- Chemical and biochemical studies of 2-propynylpyrrolidine derivatives. Restricted-rotation analogues of N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide (BM-5)
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A series of optically pure 2-[substituted-3-aminopropynyl]pyrrolidine derivatives, which are restricted-rotation analogues of the muscarinic agent N-methyl-N-(1-methyl-4-pyrrolidino-2-butynyl)acetamide (BM-5, compound 1), have been prepared from d- and l-proline. The compounds when tested in a series of in vitro muscarinic assays [[3H]CD (cortex), [3H]QNB (cortex), [3H]PZ (cortex), [3H]QNB (heart), [3H]QNB + GppNHp (heart)] were found to have weaker muscarinic properties than compound 1. The decrease in affinity was attributed to the increased size of the molecule resulting from the addition of a methylene group to form the pyrrolidine ring. The use of optically active compounds provided a more detailed examination of the complex pharmacological effects of the flexible muscarinic agent 1. The R enantiomers in the acetamide derivatives 12b, 12d, and 12f had a 5-10-fold greater affinity for the muscarinic receptor than the corresponding S enantiomers. A 5-fold difference or less found in the (R)- and (S)-carbamate derivatives 9, 15, and 16 suggested close overlap of the two enantiomers in the receptor binding domain. The affinity differences found in the enantiomeric acetamido derivatives when compared to those of the carbamate analogues may be the result of limited rotation of the acetamido group.
- Trybulski,Kramss,Mangano,Rusinko III
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p. 3190 - 3198
(2007/10/02)
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- Synthesis of chiral α-acetylenic cyclic amines from α-amino acids: Applications to differentially constrained oxotremorine analogues as muscarinic agents
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Application of the Cory-Fuchs reaction on Boc-prolinal, Boc-4-hydroxyprolinal, Boc-piperidinal and Boc-serinal derivatives to give chiral 2-pyrrolidinyl-, 2-piperidinyl- and 4-oxazolidinyl-acetylene derivatives provided rapid access to a number of differentially constrained oxotremorine analogues as muscarinic agents.
- Chung,Wasicak
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p. 3957 - 3960
(2007/10/02)
-