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Total synthesis of 7- and 8-oxygenated pyrano[3,2-a]carbazole and pyrano[2,3-a]carbazole alkaloids via boronic acid-catalyzed annulation of the pyran ring
The boronic acid-catalyzed annulation of citral opens up a short route to oxygenated cyclized monoterpenoid pyranocarbazole alkaloids. Thus, murrayamine-D is available in only three steps and 55% overall yield from the corresponding carbazole precursor.
Julich-Gruner, Konstanze K.,Kataeva, Olga,Schmidt, Arndt W.,Knoelker, Hans-Joachim
p. 8536 - 8540
(2014)
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SULFONIMIDAMIDE COMPOUNDS AS NLRP3 MODULATORS
Described herein are compounds of Formula (I), Formula (I-A), and Formula (I-B), solvates thereof, tautomers thereof, and pharmaceutically acceptable salts of the foregoing, Further described herein are methods of inhibiting NLRP3 using said compounds, and methods of and compositions useful in treating NLRP3-dependent disorders.
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Paragraph 0797

(2021/07/31)

Template-Hopping Approach Leads to Potent, Selective, and Highly Soluble Bromo and Extraterminal Domain (BET) Second Bromodomain (BD2) Inhibitors
A number of reports have recently been published describing the discovery and optimization of bromo and extraterminal inhibitors which are selective for the second bromodomain (BD2); these include our own work toward GSK046 (3) and GSK620 (5). This paper describes our approach to mitigating the genotoxicity risk of GSK046 by replacement of the acetamide functionality with a heterocyclic ring. This was followed by a template-hopping and hybridization approach, guided by structure-based drug design, to incorporate learnings from other BD2-selective series, optimize the vector for the amide region, and explore the ZA cleft, leading to the identification of potent, selective, and bioavailable compounds 28 (GSK452), 39 (GSK737), and 36 (GSK217).
Aylott, Helen E.,Atkinson, Stephen J.,Bamborough, Paul,Bassil, Anna,Chung, Chun-Wa,Gordon, Laurie,Grandi, Paola,Gray, James R. J.,Harrison, Lee A.,Hayhow, Thomas G.,Messenger, Cassie,Mitchell, Darren,Phillipou, Alexander,Preston, Alex,Prinjha, Rab K.,Rianjongdee, Francesco,Rioja, Inmaculada,Seal, Jonathan T.,Wall, Ian D.,Watson, Robert J.,Woolven, James M.,Demont, Emmanuel H.
p. 3249 - 3281
(2021/04/06)

Improved Synthesis of MediPhos Ligands and Their Use in the Pd-Catalyzed Enantioselective N-Allylation of Glycine Esters
A new class of chiral C2-symmetric diphosphines (MediPhos) was recently shown to give superior results in the Pd-catalyzed asymmetric N-allylation of amino acid esters. We here describe a new, improved protocol for the preparation of such ligands through bidirectional SN2-coupling of a tartrate-derived ditosylate with 6-alkyl-2-bromophenols followed by double lithiation/phosphanylation. This method gave access to a series of nine ligands with branched alkyl substituents, which were benchmarked in the enantioselective Pd-catalyzed N-allylation of tert-butyl glycinate with racemic (E)-2,8-dimethylnona-5-en-4-yl methyl carbonate (up to 95 % ee). In addition, the analogous transformation of tert-butyl glycinate with methyl (E)-nona-5-en-4-yl carbonate was optimized. The obtained allylic amines were then used in the stereoselective synthesis of the conformationally restricted proline-derived dipeptide analogs ProM-17 and ProM-21.
Albat, Dominik,Neud?rfl, J?rg-Martin,Reiher, Martin,Schmalz, Hans-Günther
supporting information
p. 4237 - 4242
(2021/08/24)

Design, synthesis and biological evaluation of 2-substituted-6-[(4-substituted-1-piperidyl)methyl]-1H-benzimidazoles as inhibitors of ebola virus infection
Novel 2-substituted-6-[(4-substituted-1-piperidyl)methyl]-1H-benzimidazoles were designed and synthesized as Ebola virus inhibitors. The proposed structures of the new prepared benzimidazole-piperidine hybrids were confirmed based on their spectral data and CHN analyses. The target compounds were screened in vitro for their anti-Ebola activity. Among tested molecules, compounds 26a (EC50=0.93 μM, SI = 10) and 25a (EC50=0.64 μM, SI = 20) were as potent as and more selective than Toremifene reference drug (EC50 = 0.38 μM, SI = 7) against cell line. Data suggests that the mechanism by which 25a and 26a block EBOV infection is through the inhibition of viral entry at the level of NPC1. Furthermore, a docking study revealed that several of the NPC1 amino acids that participate in binding to GP are involved in the binding of the most active compounds 25a and 26a. Finally, in silico ADME prediction indicates that 26a is an idealy drug-like candidate. Our results could enable the development of small molecule drug capable of inhibiting Ebola virus, especially at the viral entry step.
Bessières, Maxime,Plebanek, El?bieta,Chatterjee, Payel,Shrivastava-Ranjan, Punya,Flint, Mike,Spiropoulou, Christina F.,Warszycki, Dawid,Bojarski, Andrzej J.,Roy, Vincent,Agrofoglio, Luigi A.
(2021/02/06)

Benzo four-ring derivative as well as preparation method and application thereof in medicine
The invention relates to a benzo tetracyclic derivative as well as a preparation method and medical application thereof, and particularly relates to a benzo tetracyclic derivative shown in a formula (I) or a stereisomer and a pharmaceutically acceptable salt or a predrug thereof, a preparation method thereof, a medicine composition containing the same, and application of a compound or a composition in the field of central nerve. (The formula (I) is shown in the description.).
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Paragraph 0050; 0054-0059

(2020/11/22)

COMPOUNDS HAVING EXCITED STATE INTRAMOLECULAR PROTON TRANSFER (ESIPT) CHARACTER FOR USE IN TREATING AND/OR PREVENTING SUNBURN AND/OR PREVENTING U.V. DAMAGE
This disclosure relates to use of cashew nut shell liquid (CNSL) phenolics in the manufacture of molecules having ESIPT character, wherein said molecules are UVA and/or UVB absorbers, and further wherein said molecules are formulated as protectants against UVA and/or UVB radiation. The disclosure extends to use of CNSL in the manufacture of compositions including molecules having ESIPT character for treating and/or preventing sunburn and/or preventing U.V. damage.
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Page/Page column 23

(2020/09/27)

4-(2,4-BIS(2-HYDROXYPHENYL)-1H-IMIDAZOL-1-YL)BENZOIC ACID DERIVATIVES AS NOVEL IRON CHELATORS
The invention relates to novel compounds of the general formula (I) pharmaceutical compositions comprising them and the use thereof as medicaments, in particular for the use as iron chelators, more particularly for the use in the prophylaxis and/or treatm
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Page/Page column 62

(2020/10/20)

Bimetal complex with aryloxy ether skeleton, and preparation method and application thereof
The invention provides a bimetallic complex with an aryloxy ether skeleton, and a preparation method and application of the bimetallic complex. The bimetallic complex has a structural expression as shown in the specification. A catalytic system of the bimetallic complex shows very good catalytic activity and thermal stability when being used for catalyzing olefin homopolymerization or olefin/alphaolefin copolymerization reactions, and a polymerization product generated by catalysis has relatively high molecular weight and a high alpha-olefin insertion rate and has a very good industrial application prospect.
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Paragraph 0129; 0136-0137

(2020/11/26)

Formation and Activation of Zr/Hf Bis(phenolate-ether) Precatalysts
Zr and Hf complexes of bis(phenolate-ether) (“O4”) ligands feature high activity, stereoselectivity and molecular weight capability for propene polymerization at high temperature. Here we report a simplified ligand synthesis and several new examples of O4
Cuthbert, Eric N. T.,Busico, Vincenzo,Herbert, David E.,Budzelaar, Peter H. M.
supporting information
p. 3396 - 3410
(2019/08/12)

Valorisation of Cashew Nut Shell Liquid Phenolics in the Synthesis of UV Absorbers
With current concerns over the use of fossil resources for chemical synthesis of functional molecules and the effect of current UV absorbers in sunscreens have on the ecosystem, we describe a xylochemical synthesis of different classes of aromatic UV absorbers utilizing cashew nut shell liquid as a non-edible bio-renewable carbon source. Hydroxybenzophenones, xanthones, triazines, and flavones were synthesized starting from cardanol or anacardic acid. Several compounds exhibited favorable UVA and UVB absorption characteristics.
Ngwira, Kennedy J.,Kühlborn, Jonas,Mgani, Quintino A.,de Koning, Charles B.,Opatz, Till
p. 4778 - 4790
(2019/08/07)

Control of tandem isomerizations: Flow-assisted reactions of: O -lithiated aryl benzyl ethers
Tandem chemical changes are often difficult to control at will, because they proceed rapidly through multiple unstable reactive intermediates. It is desirable to develop a novel method for controlling such tandem changes to obtain desired products with high selectivity. Herein, we report a flow microreactor platform for controlling tandem isomerizations of o-lithiated aryl benzyl ethers based on precise residence time control.
Lee, Hyune-Jea,Kim, Heejin,Yoshida, Jun-Ichi,Kim, Dong-Pyo
supporting information
p. 547 - 550
(2018/01/19)

NOVEL MODULATORS OF THE SIGMA-2 RECEPTOR AND THEIR METHOD OF USE
Pharmaceutical compositions of the invention comprise functionalized lactone derivatives having a disease-modifying action in the treatment of diseases associated with dysregulation of sigma- 2 receptor activity.
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Paragraph 0569

(2018/10/19)

5-HYDROXYTRYPTAMINE RECEPTOR 7 MODULATORS AND THEIR USE AS THERAPEUTIC AGENTS
Pharmaceutical compositions of the invention comprise functionalized lactone derivatives having a disease-modifying action in the treatment of diseases associated with dysregulation of 5-hydroxytryptamine receptor 7 activity.
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Paragraph 0515

(2018/10/19)

BENZIMIDAZOL DERIVATIVES FOR TREATING FILOVIRUS INFECTION
The present invention relates to compounds comprising a benzimidazole scaffold, and the use of such compounds for the treatment of viral diseases. The invention also relates to pharmaceutical compositions comprising said compounds as an active ingredient. In particular the compounds of the invention comprising a benzimidazole scaffold are used for the treatment of filoviruses or retroviruses, and preferably for the treatment of Ebola virus or HIV virus.
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Page/Page column 79

(2018/04/13)

Polycyclic aromatic compound serving as electroluminescence and luminescence apparatus thereof
The invention belongs to the technical field of organic photoelectric materials, and relates to a polycyclic aromatic compound serving as electroluminescence and a luminescence apparatus thereof. Thepolycyclic aromatic compound has a molecular structure as shown in formula (1): (shown in the description). According to the polycyclic aromatic compound provided by the invention, small conjugated aromatic rings are connected by virtue of elements or groups such as boron and phosphorus to form a polycyclic aromatic compound. The small conjugated ring system is connected by adopting a non-carbon bridge group, so that the strong conjugated interaction among multiple rings can be reduced, the delocalization degree of HOMO and LUMO can be inhibited, the energy difference of HOMO-LUMO cannot be reduced, and the T1 energy grade is not too low; and therefore, the compound has large HOMO-LUMO energy difference, and can emit high-quality blue, skyblue and dark-blue light.
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Paragraph 0047; 0049; 0050; 0058

(2019/01/07)

Design, Synthesis, and Evaluation of a Series of Novel Benzocyclobutene Derivatives as General Anesthetics
In the present work, a series of structurally novel benzocyclobutene derivatives were identified as general anesthetics through the loss of righting reflex (LORR) experiment on mice. Our initial efforts found compound 1a with a fused four-membered ring on the 2,3-position of the phenol ring could significantly improve the safety profile. Further SAR study revealed that small hydrogen bond acceptor (HBA) groups are optimal for good ED50 along with much broader therapeutic windows, such as compounds 16b and 17. Present work demonstrates the superiority of this novel benzocyclobutene scaffold.
Zhang, Chen,Li, Fangqiong,Yu, Yan,Huang, Anbang,He, Ping,Lei, Ming,Wang, Jianmin,Huang, Longbin,Liu, Zhenhong,Liu, Jianyu,Wei, Yonggang
supporting information
p. 3618 - 3625
(2017/05/19)

Method for preparing azoxystrobin on basis of Suzuki reaction
The invention relates to a method for preparing azoxystrobin on basis of a Suzuki reaction. The method comprises the following steps: dissolving a mixture composed of methyl (E)-2-[2-(6-chloropyrimidinyl-4-yloxo)phenyl]-3-methoxy acrylate, cesium carbonate and 2-cyanophenol according to a molar ratio of 1:2:2 in a solvent, stirring at 85DEG C under the protection of N2 for 7h, and separating and purifying the obtained mixture to prepare azoxystrobin. The novel green synthesis method provided by the invention has the advantages of low cost, high yield, simple process, and suitableness for mass production.
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Paragraph 0032; 0037; 0038

(2016/10/10)

Identification of Ligand Binding Hot Spots of the Histamine H1 Receptor following Structure-Based Fragment Optimization
Developments in G protein-coupled receptor (GPCR) structural biology provide insights into GPCR-ligand binding. Compound 1 (4-(2-benzylphenoxy)piperidine) with high ligand efficiency for the histamine H1 receptor (H1R) was used to design derivatives to investigate the roles of (i) the amine-binding region, (ii) the upper and lower aromatic region, and (iii) binding site solvation. SAR analysis showed that the amine-binding region serves as the primary binding hot spot, preferably binding small tertiary amines. In silico prediction of water network energetics and mutagenesis studies indicated that the displacement of a water molecule from the amine-binding region is most likely responsible for the increased affinity of the N-methylated analog of 1. Deconstruction of 1 showed that the lower aromatic region serves as a secondary binding hot spot. This study demonstrates that an X-ray structure in combination with tool compounds, assessment of water energetics, and mutagenesis studies enables SAR exploration to map GPCR-ligand binding hot spots.
Kuhne, Sebastiaan,Kooistra, Albert J.,Bosma, Reggie,Bortolato, Andrea,Wijtmans, Maikel,Vischer, Henry F.,Mason, Jonathan S.,De Graaf, Chris,De Esch, Iwan J.P.,Leurs, Rob
p. 9047 - 9061
(2016/10/22)

The intramolecular 5-: Exo, 7- endo -dig transition metal-free cyclization sequence of (2-alkynylphenyl) benzyl ethers: Synthesis of seven-membered fused benzo [b] furans
Base-promoted cyclization of (2-alkynylphenyl) benzyl ethers was studied in detail. The effects of the solvent, base, temperature, reaction time and amount of base on the efficacy of the cyclization reaction were analyzed and a new base-solvent system (tert-BuOK/DMSO) for effective cyclization of (2-alkynylphenyl) benzyl ethers was reported. The results showed that the cyclization reactions proceeded cleanly and smoothly under mild reaction conditions, employing tert-BuOK as a base, and DMSO as a solvent, at room temperature in a short reaction time (1 h). Under these conditions, a number of different substituted (2-alkynylphenyl) benzyl ethers were cyclized to the corresponding fused heterocycle cyclohepta[b]furans. This one-pot, two-step procedure occurred regioselectively giving only the cyclohepta[b]furans as the unique regioisomers via an initial intramolecular 5-exo-dig mode followed by an intramolecular 7-endo-dig mode. The cyclohepta[b]furan derivatives absorbed in the UV region (300-350 nm range) with molar absorptivity coefficient values attributed to spin and symmetry allowed π-π? electronic transitions. An emission located in the purple region (380-440 nm range), with a Stokes shift between 65-100 nm is probably associated with the charge transfer character of the excited state. The electrochemical analysis (CV) of the cyclohepta[b]furans showed an oxidation and reduction process, probably due to the presence of the selenium atom and π-anion radical species.
Gai, Rafaela,Do Carmo Pinheiro, Roberto,Neto, José S. S.,Iglesias, Bernardo A.,Acunha, Thiago V.,Back, Davi F.,Zeni, Gilson
p. 6648 - 6658
(2018/06/08)

A concise synthesis of azoxystrobin using a Suzuki cross-coupling reaction
A simple, efficient and eco-friendly process for the synthesis in good yield of azoxystrobin from 2-bromophenol has been developed using phenolic hydroxyl protection, Grignard reaction, Suzuki cross-coupling, hydrogenation and a nucleophilic reaction on a 2-chloropyrimidine.
Liu, Yong-Gan,Luo, Yan,Lu, Yao
p. 586 - 589
(2015/11/27)

Synthesis and biological evaluation of α-aryl-α-tetralone derivatives as hepatitis C virus inhibitors
The synthesis of a novel series of 1-carba-isoflavanones through the α-arylation of α-tetralones is described. Several of these compounds demonstrated potent activity and selectivity in-vitro against HCV replicon reporter cells. Compound 10 (LQB-314) exhibited the best profile being active and selective in both replicon reporter cells (IC50 1.8 μM, SI > 111 and IC50 4.3 μM, SI > 46 in Huh7/Rep-Feo1b and Huh7.5-FGR-JC1-Rluc2A, respectively). Compound 3 (LQB-307) was the more potent and selective for Huh7.5-FGR-JC1-Rluc2A replicon reporter cells (IC50 1.5 μM, SI > 101.4).
Manvar, Dinesh,Fernandes, Talita De A.,Domingos, Jorge L.O.,Baljinnyam, Erdenechimeg,Basu, Amartya,Junior, Eurides F.T.,Costa, Paulo R.R.,Kaushik-Basu, Neerja
p. 51 - 54
(2015/02/19)

Tetrabutyl ammonium bromide-mediated benzylation of phenols in water under mild condition
Benzylation of phenol was successfully achieved in water under room temperature mediated by tetrabutylammonium bromide (TBAB) for only 2 h affording the corresponding benzyl phenyl ether with good to excellent yields. This protocol is very efficient, simple, avoiding catalysts, easy to work-up after reaction, and especially 'green'.
Wang, Hailei,Ma, Yuping,Tian, Heng,Yu, Ajuan,Chang, Junbiao,Wu, Yangjie
p. 2669 - 2673
(2014/04/03)

NOVEL COMPOUNDS AS DIACYLGLYCEROL ACYLTRANSFERASE INHIBITORS
This invention relates to novel compounds which are inhibitors of acyl coenzyme A: diacylglycerol acyltransferase 1 (DGAT-1 ), to pharmaceutical compositions containing them, to processes for their preparation, and to their use in therapy, alone or in combination with weight management therapies or other triglyceride lowering therapy for the prevention or treatment of diseases related to DGAT-1 dysfunction or where modulation of DGAT-1 activity may have therapeutic benefit.
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Page/Page column 40

(2014/06/11)

NOVEL COMPOUNDS AS DIACYLGLYCEROL ACYLTRANSFERASE INHIBITORS
This invention relates to novel compounds which are inhibitors of acyl coenzyme A: diacylglycerol acyltransferase 1 (DGAT-1), to pharmaceutical compositions containing them, to processes for their preparation, and to their use in therapy, alone or in comb
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Paragraph 0203-0204

(2014/06/11)

Triarylphosphine ligands with hemilabile alkoxy groups: Ligands for nickel(II)-catalyzed olefin dimerization reactions. hydrovinylation of vinylarenes, 1,3-dienes, and cycloisomerization of 1,6-dienes
Substitution of one of the phenyl groups of triphenylphosphine with a 2-benzyloxy-, 2-benzyloxymethyl- or 2-benzyloxyethyl-phenyl moiety results in a set of simple ligands, which exhibit strikingly different behaviour in various nickel(II)-catalyzed olefin dimerization reactions. Complexes of ligands with 2-benzyloxyphenyl- and 2-benzyloxymethylphenyldiphenylphosphine (L5 and L6, respectively) are most active for hydrovinylation (HV) of vinylarenes, with the former leading to extensive isomerization of the primary 3-aryl-1-butenes into the conjugated 2-aryl-2-butenes even at -55 °C. However, 2-benzyloxymethyl-substituted ligand L6 is slightly less active, affording up to quantitative yields of the primary products of HV at ambient temperature with no trace of isomerization, thus providing the best option for a practical synthesis of these compounds. In sharp contrast, hydrovinylation of a variety of 1,3-dienes is best catalyzed by nickel(II) complexes of 2- benzyloxyphenyldiphenylphosphine, L5. The other two ligands, 2-benzyloxymethyl- (L6) and 2-benzyloxyethyldiphenylphosphine (L7) are much less effective in the HV of 1,3-dienes. Nickel(II)-catalyzed cycloisomerization of 1,6-dienes into methylenecyclopentanes, a reaction mechanistically related to the other hydrovinylation reactions, is also uniquely effected by nickel(II) complexes of L5, but not of L6 or L7. In an attempt to prepare authentic samples of the methylencyclohexane products, nickel(II) complexes of N-heterocyclic carbene ligands were examined. In sharp contrast to the phosphines, which give the methylenecyclopentanes, methylenecyclohexanes are the major products in the (N-heterocyclic carbene)nickel(II)-mediated reactions.
Biswas, Souvagya,Zhang, Aibin,Raya, Balaram,Rajanbabu
supporting information
p. 2281 - 2292
(2014/07/21)

Facile formation of imidazolinium salt by reaction of corresponding diamine and trimethyl orthoformate in 1,1,1,3,3,3-hexafluoroisopropanol
The preparation of imidazolinium salts, which can be used as precursors of pincer-type N-heterocyclic carbene ligands, is described. The formation of imidazolinium salts under standard conditions is difficult, but they have been successfully synthesized by reaction of the corresponding diamines and trimethyl orthoformate in 1,1,1,3,3,3-hexafluoroisopropanol. The synthesis of new chiral C2 symmetric imidazolinium salts is also described.
Usui, Kensuke,Nakada, Masahisa
p. 1539 - 1551
(2016/11/07)

COMPOUNDS AND METHODS FOR USE IN TREATING NEOPLASIA AND CANCER
The present invention relates to a novel method for the treatment of neoplasia, including cancer and other diseases and conditions in humans and mammals. More particularly, in preferred aspects, the present invention provides a method for the use of novel compounds for the treatment of neoplasia, hyperproliferative cell growth including psoriasis, restenosis following cardiovascular surgery, hyperplasia, including renal hyperplasia, chronic inflammatory diseases including rheumatoid and osteoarthritis, among others.
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Page/Page column 62

(2013/03/26)

Amide-modified prenylcysteine based Icmt inhibitors: Structure-activity relationships, kinetic analysis and cellular characterization
Human protein isoprenylcysteine carboxyl methyltransferase (hIcmt) is the enzyme responsible for the α-carboxyl methylation of the C-terminal isoprenylated cysteine of CaaX proteins, including Ras proteins. This specific posttranslational methylation event has been shown to be important for cellular transformation by oncogenic Ras isoforms. This finding led to interest in hIcmt inhibitors as potential anti-cancer agents. Previous analog studies based on N-acetyl-S-farnesylcysteine identified two prenylcysteine-based low micromolar inhibitors (1a and 1b) of hIcmt, each bearing a phenoxyphenyl amide modification. In this study, a focused library of analogs of 1a and 1b was synthesized and screened versus hIcmt, delineating structural features important for inhibition. Kinetic characterization of the most potent analogs 1a and 1b established that both inhibitors exhibited mixed-mode inhibition and that the competitive component predominated. Using the Cheng-Prusoff method, the K i values were determined from the IC50 values. Analog 1a has a KIC of 1.4 ± 0.2 μM and a KIU of 4.8 ± 0.5 μM while 1b has a KIC of 0.5 ± 0.07 μM and a KIU of 1.9 ± 0.2 μM. Cellular evaluation of 1b revealed that it alters the subcellular localization of GFP-KRas, and also inhibits both Ras activation and Erk phosphorylation in Jurkat cells.
Majmudar, Jaimeen D.,Hodges-Loaiza, Heather B.,Hahne, Kalub,Donelson, James L.,Song, Jiao,Shrestha, Liza,Harrison, Marietta L.,Hrycyna, Christine A.,Gibbs, Richard A.
experimental part
p. 283 - 295
(2012/02/17)

Synthesis of the C19 methyl ether of aspercyclide A via germyl-Stille macrocyclisation and ELISA evaluation of both enantiomers following optical resolution
Aspercyclide A (1) is a biaryl ether containing 11-membered macrocyclic natural product antagonist of the human IgE-FcεRI protein-protein interaction (PPI); a key interaction in the signal transduction pathway for allergic disorders such as asthma. Herein
Carr, James L.,Sejberg, Jimmy J. P.,Saab, Fabienne,Holdom, Mary D.,Davies, Anna M.,White, Andrew J. P.,Leatherbarrow, Robin J.,Beavil, Andrew J.,Sutton, Brian J.,Lindell, Stephen D.,Spivey, Alan C.
experimental part
p. 6814 - 6824
(2011/11/14)

Erratum: Straightforward synthesis of enantiopure 2,3-dihydrobenzofurans by a sequential stereoselective biotransformation and chemical intramolecular cyclization (Organic Letters (2010) 12)
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Mangas-Sanchez, Juan,Busto, Eduardo,Gotor-Fernandez, Vicente,Gotor, Vicente
scheme or table
p. 5711 - 5712
(2011/12/04)

Discovery of 3-aryl-5-acylpiperazinyl-pyrazoles as antagonists to the NK3 receptor
A series of 3-aryl-5-acylpiperazinyl-pyrazoles (e.g., 3a-b) initially identified through a high-throughput screening campaign using the aequorin Ca2+ bioluminescence assay as novel, potent small molecule antagonists of the G protein-coupled hum
Hoveyda, Hamid R.,Roy, Marie-Odile,Blanc, Sebastien,No?l, Sophie,Salvino, Joseph M.,Ator, Mark A.,Fraser, Graeme
scheme or table
p. 1991 - 1996
(2011/04/24)

THERAPEUTICALLY ACTIVE COMPOUNDS FOR USE IN THE TREATMENT OF CANCER CHARACTERIZED AS HAVING AN IDH MUTATION
Compounds and compositions comprising compounds useful in the treatment of cancer are described herein. The compounds and compositions can be used to modulate an isocitrate dehydrogenase (IDH) mutant (e.g., IDHIm or IDH2m) having alpha hydroxyl neoactivity
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Page/Page column 132

(2011/06/26)

AMINO HETEROARYL COMPOUNDS AS BETA-SECRETASE MODULATORS AND METHODS OF USE
The present invention comprises a new class of compounds useful for the modulation of Beta-secretase enzyme activity and for the treatment of Beta-secretase mediated diseases, including Alzheimer's disease (AD) and related conditions. In one embodiment, the compounds have a general Formula (I); wherein ring A, B1, B2, B3, L, R1, R2, ring Z, m and n of Formula I are defined herein. The invention also includes use of these compounds in pharmaceutical compositions for treatment, prophylactic or therapeutic, of disorders and conditions related to the activity of beta-secretase protein. Such disorders include, for example, Alzheimer's Disease (AD), cognitive deficits, cognitive impairment, schizophrenia and other central nervous system conditions related to and/or caused by the formation and/or deposition of plaque on the brain. The invention also comprises further embodiments of Formula (I), intermediates and processes useful for the preparation of compounds of Formula (I).
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Page/Page column 87

(2011/08/08)

Straightforward synthesis of enantiopure 2,3-dihydrobenzofurans by a sequential stereoselective biotransformation and chemical intramolecular cyclization
(Equation Presented). A new family of optically active 2,3- dihydrobenzofurans has been prepared by a simple chemoenzymatic asymmetric strategy. This synthetic approach is based on the combination of a lipase-mediated kinetic resolution of 1-aryl-2-propanols or bioreduction of the corresponding ketones followed by an intramolecular cyclization reaction. These novel compounds have been prepared in enantiopure form and in good overall yield through a straightforward route.
Mangas-Sanchez, Juan,Busto, Eduardo,Gotor-Fernandez, Vicente,Gotor, Vicente
supporting information; experimental part
p. 3498 - 3501
(2010/10/20)

The first total synthesis of the natural product angoluvarin
The total synthesis of angoluvarin, a member of the dihydrochalcone family of natural products, is reported. Starting with 2-bromophenol, the synthesis was accomplished in eight steps with an overall yield of 2%. This represents the first reported synthes
Nutaitis, Charles F.
supporting information; experimental part
p. 5497 - 5499
(2010/11/02)

Oligomeric benzylsulfonium salts: Facile benzylation via high-load ROMP reagents
(Chemical Equation Presented) The development of high-load, oligomeric benzylsulfonium salts, generated via ring-opening metathesis polymerization, and their utility in facile benzylations of various nucleophiles is reported. These oligomeric sulfonium salts exist as free-flowing powders and are stable at room temperature. After the benzylation event, purification is attained via simple dry load/filtration, followed by solvent removal to deliver products in excellent yield and purity.
Zhang, Mianji,Flynn, Daniel L.,Hanson, Paul R.
p. 3194 - 3198
(2008/02/04)

N,N-dimethylglycine-promoted ullmann-type coupling reactions of aryl iodides with aliphatic alcohols
The Ullmann-type coupling reactions of aryl iodides and aliphatic alcohols occur at 110°C with N,N-dimethylglycine as the ligand, giving aryl alkyl ethers in good to excellent yields. Georg Thieme Verlag Stuttgart.
Zhang, Hui,Ma, Dawei,Cao, Weiguo
p. 243 - 246
(2007/10/03)

Hydrovinylation of 1,3-dienes: A new protocol, an asymmetric variation, and a potential solution to the exocyclic side chain stereochemistry problem
Cyclic and acyclic 1,3-dienes undergo efficient (substrate/catalyst = 72) heterodimerization with ethylene in the presence of a Ni catalyst prepared from [o-(PhCH2O)]C6H4PPh2, [(allyl)2NiBr]2, and Na+ BAr4- (Ar = 3,5-bis-trifluromethylphenyl), giving 1,2-addition products. Yields up to 99% can be realized for several 1-vinylcycloalkenes and 1-substituted 1,3-butadienes. Phospholanes with suitably placed hemilabile ligating groups and phosphoramidites derived from binaphthol are excellent ligands for an asymmetric variation of this reaction, the latter giving 99% yield and >95% ee's for selected substrates. An example of how an exocyclic chiral center can be used to install other stereo-centers in the ring (e. g., the carbon to which the side chain is attached) is also provided. These discoveries open an expeditious entry into several biologically relevant classes of compounds, especially those carrying tetrahydronaphthalene and related heterocyclic moieties. Copyright
Zhang, Aibin,RajanBabu
p. 54 - 55
(2007/10/03)

Practical synthesis of aromatic ethers by SNAr of fluorobenzenes with alkoxides
Aromatic fluorines have been substituted by alkoxides in a variety of activated and unactivated aromatic systems.
Rodriguez, Juan R.,Agejas, Javier,Bueno, Ana B.
p. 5661 - 5663
(2007/10/03)

Substituted benzoic acid derivatives exhibiting nf-k b inhibiting activity
A substituted benzoic acid derivative which is represented by the following formula (I) and has an NF-κB inhibiting action (in the formula, R3, R4 and R5 each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon(s) or an alkoxy group having 1 to 6 carbon(s); R9 and R10 each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon(s) or an acyl group having 2 to 11 carbons); R2 represents an optionally-substituted aromatic hydrocarbon group or an optionally-substituted heterocyclic group; and X represents a carboxyl group which may be esterified or amidated).
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Page/Page column 9-10

(2008/06/13)

Stereoselective synthesis of (±)-rocaglaol analogues
(Chemical equation presented) An intramolecular hydroxy epoxide opening was used to access the cyclopenta[d]benzofuran ring system of the natural product rocaglaol (2). Our route allowed the stereocontrolled preparation of the rocaglaol derivative (±)-(1S*,3S*,3aR*,8bS*)-3b. The synthesis of the (±)-(3R*)-epimer of 3b was also achieved. Our strategy is well-suited for the production of analogues with variation of the western ring.
Thede, Kai,Diedrichs, Nicole,Ragot, Jacques P.
p. 4595 - 4597
(2007/10/03)

Copper-catalyzed formation of carbon-heteroatom and carbon-carbon bonds
The present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of an amide or amine moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In additional embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between a nitrogen atom of an acyl hydrazine and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In other embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of a nitrogen-containing heteroaromatic, e.g., indole, pyrazole, and indazole, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-oxygen bond between the oxygen atom of an alcohol and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. The present invention also relates to copper-catalyzed methods of forming a carbon-carbon bond between a reactant comprising a nucleophilic carbon atom, e.g., an enolate or malonate anion, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. Importantly, all the methods of the present invention are relatively inexpensive to practice due to the low cost of the copper comprised by the catalysts.
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(2015/03/06)

Arylsulfonamide ethers, and methods of use thereof
Novel arylsulfonamide ether compounds and pharmaceutical compositions thereof are described. The use of the novel arylsulfonamide ether compounds and pharmaceutical compositions thereof as inhibitors of interleukin-1β converting enzyme and other cysteine proteases in the ICE family is also decribed. In addition, methods of treating stroke, inflammatory diseases, septic shock, repurfusion injury, Alzheimer's disease, and shigellosis using a compound of the invention or a pharmaceutical composition thereof are described.
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(2008/06/13)

NF-KAPPA-B INHIBITOR CONTAINING SUBSTITUTED BENZOIC ACID DERIVATIVE AS ACTIVE INGREDIENT
A novel NF-κB inhibitor represented by the following formula (I) is provided.
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(2008/06/13)

Protease inhibitors
The present invention provides compounds of formula (I) which inhibit proteases, including cathepsin K, pharmaceutical compositions of such compounds, and methods for treating diseases of excessive bone loss or cartilage or matrix degradation, including osteoporosis; gingival disease including gingivitis and periodontitis; arthritis, more specifically, osteoarthritis and rheumatoid arthritis; Paget's disease; hypercalcemia or malignancy; and metabolic bone disease therewith.
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(2008/06/13)

On the Reactivity of o-Lithioaryl Ethers: Tandem Anion Translocation and Wittig Rearrangement
(matrix presented) Allyl and benzyl 2-lithioaryl ethers, generated by bromine-lithium exchange in THF, undergo a new tandem anion translocation-[1,2]-Wittig rearrangement allowing the isolation of the corresponding benzylic alcohols.
Barluenga, Jose,Fananas, Francisco J.,Sanz, Roberto,Marcos, Cesar,Trabada, Marta
p. 1587 - 1590
(2007/10/03)

Copper-catalyzed coupling of aryl iodides with aliphatic alcohols.
[reaction: see text] A simple and mild method for the coupling of aryl iodides and aliphatic alcohols that does not require the use of alkoxide bases is described. The reactions can be performed in neat alcohol. For more precious alcohols, the etherificat
Wolter, Martina,Nordmann, Gero,Job, Gabriel E,Buchwald, Stephen L
p. 973 - 976
(2007/10/03)

PROTEASE INHIBITORS
Disclosed herein is a compound of the formula STR1 known as 2-[N-(N-benzyloxycarbonyl-L-leucinyl)]-2'-[N'-[4-(N,N-dimethylaminomethyl) benzyloxy]carbonyl-L-leucinyl]carbohydrazide; and pharmaceutically acceptable salts, hydrates and solvates thereof.
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(2008/06/13)

Aryl substituted heterocycles
The present invention concerns the novel use of aryl substituted heterocycles of formula I, set out below, which antagonize the pharmacological actions of one of ent endogenous neuropeptide tachykinins an the neurokinin 2 (NK2) receptor making them useful whenever such antagonism is desired, such as in the treatment of asthma and related conditions. The invention also provides pharmaceutical compositions containing the aryl substituted heterocycles for use in such treatment. Certain novel aryl substituted heterocycles of formula I and novel intermediates for their manufacture are also provided. STR1
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(2008/06/13)