- A short and versatile route to chiral spiroketal skeletons
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Different chiral spiroketal skeletons are obtained, in a versatile manner, by iterative alkylations of acetone N,N-dimethylhydrazone with iodides 2 followed by a one-pot deprotection/spirocyclization sequence. This methodology has been applied successfull
- Tursun, Ahmatjan,Canet, Isabelle,Aboab, Bettina,Sinibaldi, Marie-Eve
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- SYNTHESES OF 1-OXAQUINOLIZIDINES VIA REDUCTIVE CYCLIZATION OF HYDROXY-LACTAMS
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The synthesis of the 1-oxaquinolizidine moiety of xestospongin A via reductive iminium ion formation from a lactam is described. Key Words: 1-oxaquinolizidine; iminium ion; "ate" complex from DIBAL and n-BuLi; xestospongin A; iminium ion-enamine tautomeri
- Ahn, Kyo Han,Lee, Seok Jong
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- 6,7-DIHYDRO-5H-PYRIDO[2,3-C]PYRIDAZINE DERIVATIVES AND RELATED COMPOUNDS AS BCL-XL PROTEIN INHIBITORS AND PRO-APOPTOTIC AGENTS FOR TREATING CANCER
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The present invention discloses 6,7-dihydro-5H-pyrido[2,3- c]pyridazine, 1,2,3,4-tetrahydroquinoline, 1H-indole, 3,4- dihydro-2H-1,4-benzoxazine, 1H-pyrrolo[2,3-b]pyridin-1-yl, 7H- pyrrolo[2,3-c]pyridazine, 5H,6H,7H,8H,9H-pyridazino[3,4-b]azepine derivatives and related compounds of formula (I) as Bcl-xL protein inhibitors for use as pro-apoptotic agents for treating cancer, autoimmune diseases or immune system diseases. Formula (I). The description discloses the preparation of exemplary compounds (e.g. pages 113 to 354 examples 1 to 221) as well as pharmacological studies with relevant data (e.g. pages 355 to 367; examples A to E; tables 1 to 5). Exemplary compounds are e.g. 2-{6-[(1,3-benzothiazol-2-yl) amino]-1,2,3,4-tetrahydroquinolin-1-yl}-1,3-thiazole-4-carboxylic acid (example 1) or e.g. 3-{1-[(adamantan-1-yl)methyl]-5- methyl-1H-pyrazol-4-yl}-6-{3-[(1,3-benzothiazol-2-yl)amino]-4- methyl-5H,6H,7H,8H-pyrido[2,3-c]pyridazin-8-yl]pyridine-2-carboxylic acid (example 24).
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Page/Page column 296
(2021/02/05)
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- Toward an Asymmetric Synthesis of Bistramide K
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The bistramides family has shown antitumoral activity. More specifically bistramide K exhibits lower toxicity than its congeners. In this work, we describe a highly stereoselective and convergent synthesis of two building blocks of the marine metabolite b
- Bauder, Claude
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p. 4874 - 4899
(2018/09/10)
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- Synthesis of non-hydrolysable mimics of glycosylphosphatidylinositol (GPI) anchors
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Synthesis of first generation non-hydrolysable C-phosphonate GPI analogs, viz., 6-O-(2-amino-2-deoxy-α-d-glucopyranosyl)-d-myo-inositol-1-O-(sn-3,4- bis(palmitoyloxy)butyl-1-phosphonate) 23a and 6-O-(2-amino-2-deoxy-α-d- glucopyranosyl)-d-myo-inositol-1-O-(sn-2,3-bis(palmitoyloxy)propyl-1- phosphonate) 23b, is reported. The target compounds were synthesized by the coupling of α-pseudodisaccharide 21 with phosphonic acids 18a and 18b respectively in quantitative yield followed by de-protection. These synthetic C-phosphonate GPI-probes were resistant to phosphatidylinositol specific phospholipase C (PI-PLC) and also showed moderate inhibition of the enzyme activity. The Royal Society of Chemistry.
- Yadav, Mahipal,Raghupathy, Riya,Saikam, Varma,Dara, Saidulu,Singh, Parvinder Pal,Sawant, Sanghapal D.,Mayor, Satyajit,Vishwakarma, Ram A.
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p. 1163 - 1172
(2014/02/14)
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- AMINO GROUP-CONTAINING PYRROLIDINONE DERIVATIVE
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[Problems to be Solved by the Invention] To provide a drug having excellent antibacterial activity against Gram-positive bacteria and Gram-negative bacteria and also being excellent in terms of safety. [Means for Solving the Problems] A compound represented by the following formula (I) or a salt thereof: wherein R represents a hydrogen atom, a hydroxy group, or a halogen atom m represents an integer 0, 1, or 2, n represents an integer 0 or 1 Ar1 represents a bicyclic heterocyclic group represented by the following formula: wherein Aa represents a nitrogen atom or C-Ra, Ab represents a nitrogen atom or C-Rb, and Ac represents a nitrogen atom or C-Rc, Ra, Rb, and Rc independently represent a hydrogen atom or an alkyl group containing 1 to 6 carbon atoms, R1 and R2 independently represent a hydrogen atom, an alkoxy group containing 1 to 6 carbon atoms, a halogenoalkoxy group containing 1 to 6 carbon atoms, a halogen atom, or a cyano group, Ar2 represents a bicyclic heterocyclic group represented by the following formulae:
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Paragraph 0179
(2014/01/08)
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- The first total synthesis of cytopiloyne, an anti-diabetic, polyacetylenic glucoside
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The first total synthesis of cytopiloyne 1, a novel bioactive polyacetylenic glucoside isolated from the extract of Bidens pilosa, is described. The structure of cytopiloyne was determined to be 2-β-D-glucopyranosyloxy-1-hydroxytrideca-5,7,9,11-tetrayne by using various spectroscopic methods, but the chirality of the polyyne moiety was unknown. Herein, the convergent synthesis of two diastereomers of cytopiloyne by starting from commercially available 4-(2-hydroxyethyl)-2,2-dimethyl-1,3-diozolane is described. The synthetic sequence involved two key steps: stereoselective glycosylation of the glucosyl trichloroacetimidate with 1-[(4-methoxybenzyl)oxy] hex-5-yn-2-ol to give the desired β-glycoside and the construction of the glucosyl tetrayne skeleton by using a palladium/silver-catalyzed cross-coupling reaction to form the alkyne-alkyne bond, the first such use of this reaction. Comparison between the observed and published characterization data showed the 2R isomer to be the natural product cytopiloyne.
- Kumar, Chidambaram Ramesh,Tsai, Chi-Hui,Chao, Yu-Sheng,Lee, Jinq-Chyi
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experimental part
p. 8696 - 8703
(2011/10/04)
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- OXIM DERIVATIVES AS HSP90 INHIBITORS
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The invention relates to HSP90 inhibiting compounds consisting of the formula: (I) wherein the variables are as defined herein. The invention also relates to pharmaceutical compositions, kits and articles of manufacture comprising such compounds; methods and intermediates useful for making the compounds; and methods of using said compounds.
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Page/Page column 235
(2009/09/05)
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- Synthetic studies towards the marine natural product palmerolide A: Synthesis of the C3-C15 and C16-C23 fragments
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The synthesis of the C3-C15 and C16-C23 fragments of the marine natural product palmerolide A has been achieved. Georg Thieme Verlag Stuttgart.
- Cantagrel, Guillaume,Meyer, Christophe,Cossy, Janine
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p. 2983 - 2986
(2008/03/12)
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- Synthesis and applications of C2-symmetric guanidine bases
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The preparation of tetracyclic C2-symmetric guanidinium salts is reported together with their application to enantioselective transformations.
- Allingham, Matthew T.,Howard-Jones, Andrew,Murphy, Patrick J.,Thomas, Dafydd A.,Caulkett, Peter W. R.
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p. 8677 - 8680
(2007/10/03)
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- Synthesis of the ABCD ring system of azaspiracid
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Previously attempted spirocyclizations to form the ABCD ring system of azapiracid (1) have proven unsuccessful owing to the anomeric effects that favor the formation of the undesired 13S diastereomer. By the use of a hydrogen bond donor as an auxiliary gr
- Nicolaou,Qian, Wenyuan,Bernal, Federico,Uesaka, Noriaki,Pihko, Petri M.,Hinrichs, Jrgen
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p. 4068 - 4071
(2007/10/03)
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- Synthesis of (-)-bullatacin: The enantiomer of a potent, antitumor, 4-hydroxylated, Annonaceous acetogenin
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Synthesis of the title compound represents the first construction of any of these potent, antitumor Annonaceous acetogenins with the entire relative stereochemistry in place. Palladium(0)-mediated crossed diyne coupling and the use of three, natural, α-hy
- Hoye,Hanson
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p. 5043 - 5046
(2007/10/02)
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- Stereocontrolled Formation of Functionalized erythro-1,2-Diols via Hydroboration of 2-Alkyl-4,5-dihydrofurans
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trans-2-Alkyl-3-hydroxytetrahydrofurans, prepared by the stereospecific hydroboration / oxidation reaction of 2-alkyl-4,5-dihydrofurans, were regioselectively cleaved with (CH3)3SiCl/NaI to afford 1-iodo-erythro-3,4-diols in CH3CN or the corresponding acetonide derivatives in CH3COCH3.
- Amouroux, Roger,Slassi, Abdelmalik,Saluzzo, Christine
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p. 1965 - 1970
(2007/10/02)
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- Synthesis of phoracantholide I based on stereospecific fragmentation reactions
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Phoracantholide I was synthesized on the basis of silica gel-catalyzed fragmentation to the ring-enlarged lactones.
- Nagumo,Suemune,Sakai
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p. 5585 - 5588
(2007/10/02)
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- A new practical enantiospecific synthesis of unlabelled and tritium labelled 12-HETEs
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The oxidative metabolism of arachidonic acid AA is known to yield a variety of biologically active substances.Among them, both enantiomers of 12-hydroxyeicosatetraenoic acid (12-HETE) have been the subject of much interest.In order to extend their biologi
- Mosset, P.,Pointeau, P.,Aubert, F.,Lellouche, J. P.,Beaucourt, J. P.,Gree, R.
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p. 298 - 315
(2007/10/02)
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- ENHANCEMENT OF OPTICAL PURITY OF A PRODUCT BY REMOVING UNWANTED DIASTEREOMERS IN THE COURSE OF A CHIRAL SYNTHESIS: NEW SYNTHESIS OF THE STEREOISOMERS OF 2,8-DIMETHYL-1,7-DIOXASPIROUNDECANE, THE PHEROMONE OF ANDRENA WILKELLA
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(2R,6S,8R)-, (2S,6R,8S)- and (2R,6R,8S)-2,8-dimethyl-1,7-dioxaspiroundecanes were synthesized, and their specific rotations and optical purities were discussed.
- Mori, Kenji,Watanabe, Hidenori
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p. 295 - 304
(2007/10/02)
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