- X-ray Structure-Guided Discovery of a Potent, Orally Bioavailable, Dual Human Indoleamine/Tryptophan 2,3-Dioxygenase (hIDO/hTDO) Inhibitor That Shows Activity in a Mouse Model of Parkinson’s Disease
-
Human indoleamine 2,3-dioxygenase 1 (hIDO1) and tryptophan 2,3-dioxygenase (hTDO) have been closely linked to the pathogenesis of Parkinson’s disease (PD); nevertheless, development of dual hIDO1 and hTDO inhibitors to evaluate their potential efficacy against PD is still lacking. Here, we report biochemical, biophysical, and computational analyses revealing that 1H-indazole-4-amines inhibit both hIDO1 and hTDO by a mechanism involving direct coordination with the heme ferrous and ferric states. Crystal structure-guided optimization led to23, which manifested IC50values of 0.64 and 0.04 μM to hIDO1 and hTDO, respectively, and had good pharmacokinetic properties and brain penetration in mice.23showed efficacy against the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced mouse motor coordination deficits, comparable to Madopar, an anti-PD medicine. Further studies revealed that different from Madopar,23likely has specific anti-PD mechanisms involving lowering IDO1 expression, alleviating dopaminergic neurodegeneration, reducing inflammatory cytokines and quinolinic acid in mouse brain, and increasing kynurenic acid in mouse blood.
- Ning, Xiang-Li,Li, Yu-Zhi,Huo, Cui,Deng, Ji,Gao, Cheng,Zhu, Kai-Rong,Wang, Miao,Wu, Yu-Xiang,Yu, Jun-Lin,Ren, Ya-Li,Luo, Zong-Yuan,Li, Gen,Chen, Yang,Wang, Si-Yao,Peng, Cheng,Yang, Ling-Ling,Wang, Zhou-Yu,Wu, Yong,Qian, Shan,Li, Guo-Bo
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supporting information
p. 8303 - 8332
(2021/06/30)
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- Zirconium-hydride-catalyzed site-selective hydroboration of amides for the synthesis of amines: Mechanism, scope, and application
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Developing mild and efficient catalytic methods for the selective synthesis of amines is a longstanding research objective. In this respect, catalytic deoxygenative amide reduction has proven to be promising but challenging, as this approach necessitates selective C–O bond cleavage. Herein, we report the selective hydroboration of primary, secondary, and tertiary amides at room temperature catalyzed by an earth-abundant-metal catalyst, Zr-H, for accessing diverse amines. Various readily reducible functional groups, such as esters, alkynes, and alkenes, were well tolerated. Furthermore, the methodology was extended to the synthesis of bio- and drug-derived amines. Detailed mechanistic studies revealed a reaction pathway entailing aldehyde and amido complex formation via an unusual C–N bond cleavage-reformation process, followed by C–O bond cleavage.
- Han, Bo,Jiao, Haijun,Wu, Lipeng,Zhang, Jiong
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p. 2059 - 2067
(2021/09/02)
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- Design and Synthesis of 56 Shape-Diverse 3D Fragments
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Fragment-based drug discovery is now widely adopted for lead generation in the pharmaceutical industry. However, fragment screening collections are often predominantly populated with flat, 2D molecules. Herein, we describe a workflow for the design and synthesis of 56 3D disubstituted pyrrolidine and piperidine fragments that occupy under-represented areas of fragment space (as demonstrated by a principal moments of inertia (PMI) analysis). A key, and unique, underpinning design feature of this fragment collection is that assessment of fragment shape and conformational diversity (by considering conformations up to 1.5 kcal mol?1 above the energy of the global minimum energy conformer) is carried out prior to synthesis and is also used to select targets for synthesis. The 3D fragments were designed to contain suitable synthetic handles for future fragment elaboration. Finally, by comparing our 3D fragments with six commercial libraries, it is clear that our collection has high three-dimensionality and shape diversity.
- Atobe, Masakazu,Blakemore, David C.,Bond, Paul S.,Chan, Ngai S.,De Fusco, Claudia,Downes, Thomas D.,Firth, James D.,Hubbard, Roderick E.,Jones, S. Paul,Klein, Hanna F.,O'Brien, Peter,Roughley, Stephen D.,Vidler, Lewis R.,Waddelove, Laura,Whatton, Maria Ann,Wheldon, Mary C.,Woolford, Alison J.-A.,Wrigley, Gail L.
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supporting information
(2020/07/13)
-
- Discovery of γ-Lactam alkaloid derivatives as potential fungicidal agents targeting steroid biosynthesis
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Biological control of plant pathogens is considered as one of the green and effective technologies using beneficial microorganisms or microbial secondary metabolites against plant diseases, and so microbial natural products have played important roles in the research and development of new and green agrochemicals. To explore the potential applications for natural γ-lactam alkaloids and their derivatives, 26 γ-lactams that have flexible substituent patterns were synthesized and characterized, and their in vitro antifungal activities against eight kinds of plant pathogens belonging to oomycetes, basidiomycetes, and deuteromycetes were fully evaluated. In addition, the high potential compounds were further tested using an in vivo assay against Phytophthora blight of pepper to verify a practical application for controlling oomycete diseases. The potential modes of action for compound D1 against Phytophthora capsici were also investigated using microscopic technology (optical microscopy, scanning electron microscopy, and transmission electron microscopy) and label-free quantitative proteomics analysis. The results demonstrated that compound D1 may be a potential novel fungicidal agent against oomycete diseases (EC50 = 4.9748 μg·mL-1 for P. capsici and EC50 = 5.1602 μg·mL-1 for Pythium aphanidermatum) that can act on steroid biosynthesis, which can provide a certain theoretical basis for the development of natural lactam derivatives as potential antifungal agents.
- Cao, Xiufang,Huang, Daye,Huang, Wenbo,Ke, Shaoyong,Song, Di,Wang, Shuangshuang
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p. 14438 - 14451
(2020/12/23)
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- Furan-Derived Chiral Bicycloaziridino Lactone Synthon: Collective Syntheses of Oseltamivir Phosphate (Tamiflu), (S)-Pipecolic acid and its 3-Hydroxy Derivatives
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A unified synthetic strategy for oseltamivir phosphate (tamiflu), (S)-pipecolic acid, and its 3-hydroxy derivatives from furan derived common chiral bicycloaziridino lactone synthon is described here. Key features are the short (4-steps), enantiopure, and decagram-scale synthesis of common chiral synthon from furan and its first-ever application in the total synthesis of biologically active compounds by taking the advantages of high functionalization ability of chiral synthon.
- Chavan, Subhash P.,Gonnade, Rajesh G.,Kadam, Appasaheb L.,Shinde, Shrikrishna S.
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- Selective conversion of primary amides to esters promoted by KHSO4
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Primary amides, either aliphatic or aromatic, are easily converted to the corresponding esters via reflux in lower primary alcohols in the presence of KHSO4. Secondary amides lead to complicated mixtures under analogous conditions, whereastertiary amides were inert. Use of isopropyl alcohol resulted inthe formation of product atslower rate and lower yieldalong withside products, whereas, use of tertiary alcoholsdid not give successful conversion andallyl and benzyl alcohol provided complex mixtures.
- Sattenapally, Narsimha,Sharma, Jhanvi,Hou, Yuqing
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p. 174 - 183
(2018/09/10)
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- Aryne-Mediated [2,3]-Sigmatropic Rearrangement of Tertiary Allylic Amines
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A new strategy has been established for the [2,3]-sigmatropic rearrangement of quaternary allylic ammonium ylides via in situ activation of tertiary allylic amines with arynes under mild conditions. Using 2-(trimethylsilyl)aryl triflates as aryne precurso
- Zhang, Juan,Chen, Zhi-Xiong,Du, Ting,Li, Bing,Gu, Yonghong,Tian, Shi-Kai
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supporting information
p. 4872 - 4875
(2016/10/18)
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- COMPOUNDS AND USE FOR TREATING CANCER
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The present invention relates to certain 2,4-disubstituted quinoline derivatives, to their therapy, as well as to pharmaceutical compositions comprising said compounds. More specifically the invention relates to certain 2,4-disubstituted quinoline derivatives or pharmaceutical compositions comprising said compounds for the treatment of cancers characterized by overactive Ras and/or Rac or signalling pathway.
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- Therapeutic use of isomeric forms of 2-(4-chlorophenyl)quinolin-4-yl)(piperidin-2-yl)methanol
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The present invention relates to certain isomeric forms of the 2,4-disubstituted quinoline derivative Vacquinol-1 (NSC13316, (2-(4-chlorophenyl)quinolin-4-yl)(piperidin-2-yl)methanol), for use the in treatment of systemic cancer, as well as pharmaceutical compositions comprising said isomeric forms of the 2,4-disubstituted quinoline derivative Vacquinol-1 for the intended use.
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-
Paragraph 0084; 0086
(2016/09/26)
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- SPIRO COMPOUNDS AS HEPATITIS C VIRUS INHIBITORS
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Disclosed are spiro compounds of formula (I), or stereomers, geometric isomers, tautomers, nitrogen oxides, hydrates, solvates, metabolites, pharmaceutically acceptable salts or prodrugs thereof. The compounds can be used to treat hepatitis C virus (HCV) infection or hepatitis C disease. Furthermore disclosed are pharmaceutical compositions containing the compounds and the method of using the compounds or pharmaceutical compositions in the treatment of HCV infection or hepatitis C disease.
- -
-
Paragraph 0657; 0658
(2015/11/09)
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- Development of quinoline-based disruptors of biofilm formation against Vibrio cholerae
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Biofilm formation is a major cause of bacterial persistence in nosocomial infections, leading to extended treatment times and increased rates of morbidity and mortality. Despite this, there are currently no biofilm inhibitors approved for clinical use. Th
- León, Brian,Fong, Jiunn C. N.,Peach, Kelly C.,Wong, Weng Ruh,Yildiz, Fitnat H.,Linington, Roger G.
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supporting information
p. 1234 - 1237
(2013/05/09)
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- Synthesis and anticonvulsant activity of novel 2,6-diketopiperazine derivatives. Part 2: Perhydropyrido[1,2-a]pyrazines
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A new series of chiral pyrido[1,2-a]pyrazine derivatives was synthesised and evaluated in in vivo animal models of epilepsy. A significant influence of the stereochemistry of the pyrido[1,2-a]pyrazine framework on the pharmacological activity was observed
- Dawidowski, MacIej,Herold, Franciszek,Chodkowski, Andrzej,Kleps, Jerzy
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scheme or table
p. 347 - 353
(2012/03/22)
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- Ceric ammonium nitrate-mediated detritylation of tritylated amines
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Efficient deprotection of tritylated amines to the corresponding amines mediated by 20 mol % ceric ammonium nitrate [Ce(NH4) 2(NO3)6, CAN], 10 equiv of acetic acid and 15 equiv of water in dichloromethane is presented. This method equally worked well in the case of morpholino nucleosides.
- Pattanayak, Sankha,Sinha, Surajit
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experimental part
p. 34 - 37
(2011/02/25)
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- An efficient synthesis of sulfamides
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Here we report an efficient synthesis of sulfamides. 3,5-Lutidine was found to be an optimal solvent and catalyst for the reaction. The method was developed during our efforts to synthesize a series of novel FKBP-12 inhibitors in which the known ketoamide linker was replaced with sulfamide.
- Guo, Chuangxing,Dong, Liming,Kephart, Susan,Hou, Xinjun
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scheme or table
p. 2909 - 2913
(2010/06/14)
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- NOVEL BENZODIAZEPINE DERIVATIVES
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The invention relates to novel benzodiazepine derivatives with antiproliferative activity and more specifically to novel benzodiazepines of formula (I) and (II), in which the diazepine ring (B) is fused with a heterocyclic ring (CD), wherein the heterocyclic ring is bicyclic or a compound of formula (III), in which the diazepine ring (B) is fused with a heterocyclic ring (C), wherein the heterocyclic ring is monocyclic. The invention provides cytotoxic dimers of these compounds. The invention also provides conjugates of the monomers and the dimers. The invention further provides compositions and methods useful for inhibiting abnormal cell growth or treating a proliferative disorder in a mammal using the compounds or conjugates of the invention. The invention further relates to methods of using the compounds or conjugates for in vitro, in situ, and in vivo diagnosis or treatment of mammalian cells, or associated pathological conditions.
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Page/Page column 162-163
(2010/08/18)
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- 1,2-DISUBSTITUTED-4-BENZYLAMINO-PYRROLIDINE DERIVATIVES AS CETP INHIBITORS USEFUL FOR THE TREATMENT OF DISEASES SUCH AS HYPERLI PIDEMIA OR ARTERIOSCLEROSIS
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The present invention provides a compound of formula (I): wherein the variants R1, R2, R3, R4, R6, R7 are as defined herein, and wherein said compound is an inhibitor of CETP, and thus can be employed for the treatment of a disorder or disease mediated by CETP or responsive to the inhibition of CETP.
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Page/Page column 130
(2009/07/17)
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- NEW BRADYKININ B1 ANTAGONISTS
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The invention relates to compounds of formula (I), wherein R1 to R5 and X1 to X4, n and m have the meaning as cited in the description and the claims. Said compounds are useful as Bradykinin B1 antagonists. The
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Page/Page column 53
(2008/12/08)
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- Small Molecules for Imaging Protein-Protein Interactions
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A tissue is imaged to detect the presence of amyloid deposits or other target proteins prior to their aggregation into plaques, with the assistance of the administration of a labeled bifunctional compound of which one functionality binds to the target pro
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Page/Page column 8-9
(2008/06/13)
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- The synthesis of functionalised chiral bicyclic lactam and lactone N-oxides using a tandem Cope elimination/reverse Cope elimination protocol
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Functionalised hydroxylamine derivatives of (S)-proline and (R)-pipecolic acid have been prepared using a Cope elimination. These undergo reverse Cope elimination onto a pendant double bond to give bicyclic lactam and lactone N-oxides containing three contiguous chiral centres, this extends the scope and applicability of the reverse Cope elimination in the synthesis of heterocyclic systems by incorporation of the lactone and lactam structural motifs.
- Ellis, Gemma L.,O'Neil, Ian A.,Elena Ramos,Cleator, Ed,Barret Kalindjian,Chorlton, Alan P.,Tapolczay, David J.
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p. 1683 - 1686
(2008/02/05)
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- Antitumor agents 251: Synthesis, cytotoxic evaluation, and structure-activity relationship studies of phenanthrene-based tylophorine derivatives (PBTs) as a new class of antitumor agents
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Polar phenanthrene-based tylophorine derivatives (PBTs) were designed, synthesized and evaluated as potential antitumor agents. These compounds contain a core phenanthrene structure and can be synthesized efficiently in excellent yield. The newly synthesized PBTs were evaluated for cytotoxic activity against the A549 human cancer cell line. Among them, N-(2,3-methylenedioxy-6-methoxy-phenanthr-9-ylmethyl)-l-2-piperidinemethanol (34) and N-(2,3-methylenedioxy-6-methoxy-phenanthr-9-ylmethyl)-5-aminopentanol (28) showed the highest potency with IC50 values of 0.16 and 0.27 μM, respectively, which are comparable to those of currently used antitumor drugs. A structure-activity relationship (SAR) study was also explored to facilitate the further development of this new compound class.
- Wei, Linyi,Brossi, Arnold,Kendall, Ross,Bastow, Kenneth F.,Morris-Natschke, Susan L.,Shi, Qian,Lee, Kuo-Hsiung
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p. 6560 - 6569
(2007/10/03)
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- Inhibitors of tripeptidyl peptidase II. 3. Derivation of butabindide by successive structure optimizations leading to a potential general approach to designing exopeptidase inhibitors
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The cholecystokinin-8 (CCK-8)-inactivating peptidase is a serine peptidase that has been shown to be a membrane-bound isoform of tripeptidyl peptidase II (EC 3.4.14.10). It cleaves the neurotransmitter CCK-8 sulfate at the Met-Gly bond to give Asp-Tyr(SO
- Ganellin, C. Robin,Bishop, Paul B.,Bambal, Ramesh B.,Chan, Suzanne M. T.,Leblond, Bertrand,Moore, Andrew N. J.,Zhao, Lihua,Bourgeat, Pierre,Rose, Christiane,Vargas, Froylan,Schwartz, Jean-Charles
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p. 7333 - 7342
(2007/10/03)
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- Aldehyde-based racemization in the dynamic kinetic resolution of N-heterocyclic α-amino esters using Candida antarctica lipase A
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The present research introduces approaches for the dynamic kinetic resolution of the methyl esters of proline and pipecolic acid. As the result, a method was developed which is based on the acylation of the secondary amino group of the amino esters with vinyl butanoate by Candida antarctica lipase A. In the optimized method, acetaldehyde as a racemizing agent is released in situ from vinyl butanoate in the presence of triethylamine, allowing ca. 90% of the racemic proline and 70% of the pipecolic acid methyl esters to be acylated in the forms of highly enantiopure (ee=97%) butanamides with the S-absolute configurations.
- Liljeblad, Arto,Kiviniemi, Anu,Kanerva, Liisa T.
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p. 671 - 677
(2007/10/03)
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- Enantioselective lipase-catalyzed reactions of methyl pipecolinate: Transesterification and N-acylation
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The present research introduces the highly (S)-selective (E?100) acylation at the secondary ring nitrogen of methyl pipecolinate as a novel resolution method with Candida antarctica lipase A. Catalysis by lipase B leads to reactions at the methyl ester function of the substrate in an almost non-enantioselective manner.
- Liljeblad, Arto,Lindborg, Jutta,Kanerva, Anu,Katajisto, Johanna,Kanerva, Liisa T.
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p. 2471 - 2474
(2007/10/03)
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- Optically active α-aminonitrile and process for producing α-amino acid
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An aldehyde compound is reacted with an amino compound and hydrogen cyanate in the presence of a chiral zirconium catalyst obtained by mixing a zirconium alkoxide with an optically active binaphthol compound.
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- Racemic and enantiopure 4-(piperidine-2′-yl)-pyridazines: Novel synthesis of anabasine-analogues with potential nicotinic acetylcholine receptor agonist activity - A new approach via Diels-Alder reaction with inverse electron demand
-
A novel multistep synthesis of anabasine analogues bearing a bioisosteric pyridazine moiety instead of a pyridine nucleus in 2-position of the piperidine ring of the alkaloid is described. Starting materials are racemic 2-hydroxymethyl-piperidine, racemic pipecolic acid or (S)-(-)-piperidine-1,2-dicarboxylic-acid-1-tert-butyl ester. Key step of this synthetic approach is a Diels-Alder cycloaddition process with inverse electron demand utilizing diverse 1,2,4,5-tetrazines as electron-deficient dienes and the new racemic or enantiopure 2-(2′-methoxyethenyl)-piperidine as electron-rich dienophile. In this [4+2]-cycloadditions 1,2,4,5-tetrazines serve as synthons for introducing the pyridazine ring in the 2-position of the piperidine moiety.
- Stehl, Astrid,Seitz, Gunther,Schulz, Karen
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p. 1343 - 1354
(2007/10/03)
-
- Synthesis and use of 2H-azirin-3-amines as dipeptide synthons
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The synthesis of the new 2H-azirin-3-amines ('3-amino-2H-azirines') 11, 20, 28, and 33 as dipeptide synthons is described. The reactions of the starting amides with Lawesson reagent gave the corresponding thioamides, and consecutive treatment with COCl2, 1,4-diazabicyclo[2.2.2]octane (DABCO), and NaN3 led to the desired products. It is shown that these 2H-azirin-3-amines can conveniently be used as building blocks of the dipeptides Aib-(Me)Axx (Axx=alanine, valine), Aib-Homoproline, and Iva-Pro in the synthesis of several model peptides. However, some limitations apply for the synthesis of such 2H-azirin-3-amines. The starting material for the azirine synthesis, the corresponding thioamides, cannot generally be synthesized, and the 2H-azirin-3-amines could not be obtained in all cases from the thioamides prepared.
- Breitenmoser, Roland A.,Heimgartner, Heinz
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p. 885 - 912
(2007/10/03)
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- Catalytic asymmetric Strecker synthesis. Preparation of enantiomerically pure α-amino acid derivatives from aldimines and tributyltin cyanide or achiral aldehydes, amines, and hydrogen cyanide using a chiral zirconium catalyst
-
Catalytic enantioselective Strecker-type reactions of aldimines with tributyltin cyanide (Bu3SnCN) proceeded smoothly in the presence of a novel chiral zirconium catalyst. High levels of enantioselectivities in the synthesis of α-amino nitrile
- Ishitani, Haruro,Komiyama, Susumu,Hasegawa, Yoshiki,Kobayashi, Shu
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p. 762 - 766
(2007/10/03)
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- Stereospecific synthesis of the anaesthetic levobupivacaine
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Enantiomerically pure (S)-bupivacaine is synthesized from the chiral pool using cheap and readily available (S)-lysine. The key steps in this efficient synthesis include an oxidative de-amination and stereospecific ring closure to form the pipecolamide core structure.
- Adger, Brian,Dyer, Ulrich,Hutton, Gordon,Woods, Martin
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p. 6399 - 6402
(2007/10/03)
-
- Synthesis of bridged azabicyclic compounds using radical translocation reactions of 1-(o-halogenobenzoyl)-2-(prop-2-enyl)-and -(prop-2-ynyl)-piperidines
-
Methyl 1-(o-bromobenzoyl)-2-(prop-2-enyl)piperidine-2-carboxylate 8a, upon treatment with tributyltin hydride in the presence of azoisobutyronitrile in boiling toluene gave regioselectively the 8-azabicyclo[3.2.1]octane 14a (a 5-exo cyclisation product) in quantitative yield as a diastereomeric mixture (66:34). 1-(o-Bromobenzoyl)-2-(prop-2-enyl)piperidine 13 also gave the 8-azabicyclo-[3.2.1]octane 16 (75% as a diastereomeric mixture), along with the pyrido[2,1-a]isoindolone 17 (10%) and the simple reduction product 18 (5%). 1-(o-Iodobenzoyl)-2-[3-(trimethylsilyl)prop-2-ynyl]piperidine 23 afforded, in addition to the pyrido[2,1-a]isoindolone 25 (18%), the 8-azabicyclo-[3.2.1]octane 24 (75%) which was converted into the 6-oxo derivative 27. For comparison, the behaviour of the azetidine congener 31 was also examined.
- Ikeda, Masazumi,Kugo, Yasuhiro,Sato, Tatsunori
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p. 1819 - 1824
(2007/10/03)
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- FeCl3-catalyzed conjugate addition of secondary amines, imidazole and pyrazole to methyl-2-acetamidoacrylate. Preparation of β-dialkylamino-α-alanine and β-(N-heteroaryl)-α-alanine derivatives
-
β-Dialkylamino-α-alanine and β-(N-heteroaryl)-α-alanine derivatives are obtained by conjugate addition of nitrogen based nucleophiles (cyclic and acyclic secondary amines, imidazole and pirazole) to methyl 2-acetamidoacrylate 1, under iron(III) chloride catalysis.
- Perez,Pleixats
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p. 8355 - 8362
(2007/10/02)
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- Stereoselective functionalisation of N-Boc pyroaminoadipic acid: Synthesis of 5-substituted aminoadipic and pipecolic acids
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5-Alkylsubstituted aminoadipic and pipecolic acids were diastereoselectively synthesized from methyl N-Boc pyroaminoadipate.
- Ezquerra,Ezquerra, Jesus,Pedregal,Pedregal, Concepcion,Escribano,Escribano, Ana,Carreno,Carreno, M. Carmen,Garcia Ruano,Garcia Ruano, Jose L.
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p. 3247 - 3250
(2007/10/02)
-
- Experimental Studies of the Anomeric Effect. Part VI. Ring Inversion Equilibria in Cyclohexane, Tetrahydropyran and Piperidine Rings Substituted by a Carbomethoxy or a Cyano Group.
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The ring inversion equilibrium in carbomethoxycyclohexane is compared with those in 2-carbomethoxytetrahydropyran and 2-carbomethoxypiperidine through a variable temperature nmr study of the positions of equilibria.The derived ΔH0ae values (kcal mol-1) of -1.24 (cyclohexane), -1.69 (tetrahydropyran) and -0.54 (piperidine) can be rationalised in terms of competition between steric effects and endo-anomeric effects of the ring heteroatom.Variable temperature studies have also given ΔH0ae values (kcal mol-1) for ring inversions in cyanocylohexane, 2-cyanotetrahydropyran and 2-cyanopiperidine as -0.18, +0.36 and +2.22.Steric effects are small for CN, and the trend in ΔH0 values is consistent with the expected increase in stabilising endo-anomeric effect along the series C, O, N.
- Booth, Harold,Dixon, J. Mark,Khedhair, Khedhair A.
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p. 6161 - 6174
(2007/10/02)
-
- Photocatalytic One-Step Syntheses of Cyclic Imino Acids by Aqueous Semiconductor Suspensions
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Optically active cyclic imino acids, pipecolinic acid and proline, are readily obtained from α,ω-diamino carboxylic acids and their Nω-substituted derivatives by the photoirradiation of aqueous suspensions of TiO2 or CdS loaded with platinum oxides under Ar at room temperature.
- Ohtani, Bunsho,Tsuru, Shigeto,Nishimoto, Sei-ichi,Kagiya, Tsutomu
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p. 5551 - 5553
(2007/10/02)
-
- An Asymmetric Synthesis of 2-Substituted Piperidines through Ozonolysis of Cyclopentenes and Reductive Aminocyclization
-
By the action of ozone, sodium cyanoborohydride and the optically active benzylic amines 2, the 1-substituted cyclopentenes 1, 5 and 9 were converted to a diastereometric mixture of 1,2-disubstituted piperidines (3, 6 and 10), respectively.Hydrogenation of these compounds and the following work-up yielded optically active 2-alkylpiperidines (4, up to 68percente.e.), pipecolic acid (7, 84percent e.e.) and 2-(hydroxymethyl)piperidine (11, up to 85percente.e.).Chromatographic separation of the major isomers of 3b and 6 enabled optically pure coniine (4b) and pipecolic acid (7) to be prepared, respectively.
- Kawaguchi, Mamoru,Hayashi, Osamu,Sakai, Noriyuki,Hamada, Masayuki,Yamamoto, Yukio,Oda, Jun'ichi
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p. 3107 - 3112
(2007/10/02)
-
- ASSYMMETRIC SYNTHESIS OF CYCLIC IMINO ACIDS VIA CHIRAL SCHIFF BASES
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A new method of synthesis of cyclic imino acids is reported.Diastereoselective alkylation of Schiff bases (derived from α-amino esters and (+) or (-) 2-hydroxypinan-3-one) with dihalogeno compounds, followed by hydrolytic cleavage and cyclization affords the imino esters.Reactions are highly enantioselective, with one exception corresponding to steric crowding.
- Bajgrowicz, Jerzy,Achquar, Abdelrhani El,Roumestant, Marie-Louise,Pigiere, Christian,Viallefont, Philippe
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p. 2165 - 2167
(2007/10/02)
-
- REACTION OF SCHIFF BASES ANIONS WITH α,ω-DIHALOALKENES : SYNTHETIC ROUTE TO CYCLIC α-AMINOACID DERIVATIVES.
-
Imine anions of α-aminoesters, obtained from LDA/THF, undergo copper-catalyzed substitution reactions with α,ω-dihaloalkanes to lead to ω-haloalkylimines which are converted to cyclic α-aminoacid derivatives under anionic and thermal conditions.
- Joucla, M.,Goumzili El, M.
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p. 1681 - 1684
(2007/10/02)
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- Perhydrofluorenetetrol and perhydro-phenanthrenetetrol derivatives
-
Compounds are provided having the structure SPC1 Wherein n is 1 or 2, n1 is 0, 1 or 2 and n2 is 0, 1, 2 or 3, R1, R2, R3 and R4 may be the same or different and can be hydrogen, lower alkyl, halolower alkyl, acyl, lower alkoxy-carbonyl EQU1 amido EQU2 or lower alkoxyalkylene, R can be lower alkoxy, lower alkyl or cycloalkyl, R8 can be hydrogen, lower alkyl, cycloalkyl, hydroxy, dialkylaminoalkyl or R9 O(CH2)q--. X is a single bond or a straight or branched bivalent aliphatic radical and Y is EQU3 These compounds are useful in the treatment of hypertension.
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