- Dynamic covalent approach to [2]- and [3]rotaxanes by utilizing a reversible thiol-disulfide interchange reaction
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A dynamic covalent approach to disulfide-containing [2]- and [3]rotaxanes is described. Symmetrical dumbbell-shaped compounds with two secondary ammonium centers and a central located disulfide bond were synthesized as components of rotaxanes. The rotaxan
- Furusho, Yoshio,Oku, Tomoya,Hasegawa, Toshihide,Tsuboi, Akiyoshi,Kihara, Nobuhiro,Takata, Toshikazu
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- Synthesis and Band Gap Analysis of Designed Porphyrin Derivatives Containing Electron Donating and Accepting Group
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Symmetric (DD, AA1–AA5) and non-symmetric (DA1) porphyrin derivatives were synthesized through McDonald coupling of bispyrrole 2D, 2A1–2A5 with the corresponding aldehyde 3 or diol 6 as a key step. The UV–Vis spectrum and CV of those porphyrins were measu
- Chang, In-Jung,Jeon, Yea-Sel,Hwang, Kwang-Jin
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p. 173 - 179
(2019/02/14)
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- Synthesis and antimicrobial activity of small cationic amphipathic aminobenzamide marine natural product mimics and evaluation of relevance against clinical isolates including ESBL–CARBA producing multi-resistant bacteria
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A library of small aminobenzamide derivatives was synthesised to explore a cationic amphipathic motif found in marine natural antimicrobials. The most potent compound E23 displayed minimal inhibitory concentrations (MICs) of 0.5–2 μg/ml against several Gr
- Igumnova, Elizaveta M.,Mishchenko, Ekaterina,Haug, Tor,Blencke, Hans-Matti,Sollid, Johanna U. Ericson,Fredheim, Elizabeth G. Aarag,Lauksund, Silje,Stensv?g, Klara,Str?m, Morten B.
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p. 5884 - 5894
(2016/11/09)
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- Catalytic ship-in-a-bottle assembly within hollow porous nanocapusles
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Large molecules can be assembled from small components exclusively inside hollow nanocapsules with the help of entrapped catalysts. Phenyl isocyanates enter the capsules through nanopores in the capsule shells and form cyclic trimers that remain entrapped
- Ehterami, Nasim,Dergunov, Sergey A.,Ussipbekova, Yenlik,Birman, Vladimir B.,Pinkhassik, Eugene
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supporting information
p. 481 - 485
(2014/02/14)
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- Facile route to an all-organic, triply threaded, interlocked structure by templated dynamic clipping
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[2]Rotaxanes are a class of mechanically interlocked molecules which are generally depicted by an "axle-in-wheel" model, in which a dumbbell-shaped linear component is threaded through a macrocyclic component (Scheme 1 a). Functionalization of the rotaxan
- Pun, Andrew,Hanifi, David A.,Kiel, Gavin,O'Brien, Evan,Liu, Yi
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supporting information
p. 13119 - 13122
(2013/03/13)
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- Identification of a foldaxane kinetic byproduct during guest-induced single to double helix conversion
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An aromatic oligoamide sequence was designed and synthesized to fold in a single helix having a large cavity and to behave as a host for a dumbbell-shaped guest derived from tartaric acid. NMR, molecular modeling, and circular dichroism (CD) evidence demo
- Gan, Quan,Ferrand, Yann,Chandramouli, Nagula,Huc, Ivan,Kauffmann, Brice,Aube, Christophe,Dubreuil, Didier
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supporting information
p. 15656 - 15659,4
(2020/08/24)
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- 2-ARYLTHIAZOLE DERIVATIVES AS CXCR3 RECEPTOR MODULATORS
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The invention encompasses compounds of Formula I or pharmaceutically acceptable salts thereof, which are modulators of the CXCR3 chemokine receptor function useful for the treatment or prevention of pathogenic inflammatory processes, autoimmune diseases or graft rejection processes. Methods of use and pharmaceutical compositions are also encompassed.
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Page/Page column 64
(2010/11/28)
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- Structural Studies on Hydrogen-Bonding Receptors for Barbiturate Guests that Use Metal Ions as Allosteric Inhibitors
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Receptor 1 was designed to bind barbiturate substrates through a six-point hydrogen-bonding motif only in the absence of metal allosteric cofactors. It was predicted that the binding of metal ions by bipyridine ligands in 1 would result in a geometric change in the receptor to inhibit substrate recognition. However, receptor 1 showed minimal affinity for the barbiturate quests even in the absence of the metal. Binding studies on model compounds 2, 3, 5, and 6 revealed that the inactivity of 1 is due to an intramolecular hydrogen bond between the N-H donor groups and the nitrogen atoms on the first heterocycle of the bipyridine ligands. This intramolecular hydrogen-bonding was eliminated by altering the position of the tether between the bipyridine ligands and the active site to produce receptor 7. Consequently, the high affinity exhibited by 7 for the barbiturate substrate (Ka = 2.8 +/- 0.7*103 M-1 in 9 : 1 CD2Cl2/CD3CN) was significantly reduced by the addition of ZnII ions as a negative allosteric co-factor.
- Al-Sayah, Mohammed H.,McDonald, Robert,Brand, Neil R.
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p. 173 - 182
(2007/10/03)
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- LIGANDS AND CATALYSTS FOR PRODUCING ELASTOMERIC PROPYLENE POLYMERS
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A ligand useful to form a metallocene olefin polymerization catalyst comprises:wherein at least R3 and R4 are substituents having at least a bulk of a t-butyl group and, optionally, wherein R1 or R2 may be a bulky substituent group.
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- Synthesis of [2]rotaxanes by tritylative endcapping of in situ formed pseudorotaxanes having thiol or hydroxyl functionality on the axle termini
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Tritylative endcapping of an in situ formed pseudorotaxane consisting of dibenzo-24-crown-8 and an axle having a thiol group at the end by treatment with trityl hexafluorophosphate at room temperature gave the corresponding sulfide-type [2]rotaxane in hig
- Furusho, Yoshio,Rajkumar, G.Abraham,Oku, Tomoya,Takata, Toshikazu
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p. 6609 - 6613
(2007/10/03)
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- Retinoidal pyrimidinecarboxylic acids. Unexpected diaza-substituent effects in retinobenzoic acids
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Several pyridine- and pyrimidine-carboxylic acids were synthesized as ligand candidates for retinoid nuclear receptors, retinoic acid receptors (RARs) and retinoic X receptors (RXRs). Although the pyridine derivatives, 6-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbamoyl]pyridine- 3-carboxylic acid (2b) and 6-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carboxamido]pyridin e-3-carboxylic acid (5b) are more potent than the corresponding benzoic acid-type retinoids, Am80 (2a) and Am580 (5a), the replacement of the benzene ring of Am580 (5a), Am555 (6a), or Am55 (7a) with a pyrimidine ring caused loss of the retinoidal activity both in HL-60 cell differentiation assay and in RAR transactivation assay using COS-1 cells. On the other hand, pyrimidine analogs (PA series, 10 and 11) of potent RXR agonists (retinoid synergists) with a diphenylamine skeleton (DA series, 8 and 9) exhibited potent retinoid synergistic activity in HL-60 cell differentiation assay and activated RXRs. Among the synthesized compounds, 2-[N-n-propyl-N-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)amino] pyrimidine-5-carboxylic acid (PA013, 10e) is most active retinoid synergist in HL-60 assay.
- Ohta, Kiminori,Kawachi, Emiko,Inoue, Noriko,Fukasawa, Hiroshi,Hashimoto, Yuichi,Itai, Akiko,Kagechika, Hiroyuki
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p. 1504 - 1513
(2007/10/03)
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- Asymmetric catalysis, 131([≠]) - Naproxen derivatives by enantioselective decarboxylation
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A new catalytic method to synthesize the important anti-inflammatory agent naproxen [(S)-1] which has to be used as the (S) enantiomer, involves the enantioselective decarboxylation of the 6-methoxynaphth-2-yl derivative 2 of 2-cyanopropionic acid. Compound 2 was stirred in THF at 15 °C with catalytic amounts of chiral bases, which abstracted the carboxyl proton. After decarboxylation, reprotonation of the anion of 6 afforded the enantiomerically enriched naproxen nitrile 6, which may be hydrolyzed to naproxen. A variety of bases were screened, and cinchona alkaloids were found to give the best enantioselectivities. Thus, with quinidine 10, up to 34% ee was obtained for (S)-6. The enantiomeric excess could be increased by turning to amides of 9-amino-9-deoxyepicinchona alkaloids. The most successful 2- ethoxybenzantide 31a of 9-amino-9-deoxyepicinchonine 11 gave up to 71.9% ee (S)-6. Cyclic ethers like THF were suitable solvents, and at a temperature of 15 °C, conversion was quantitative within 24 h in most cases. For high enantioselectivities, 5-10 mol-% of chiral base was sufficient, and the catalyst could be fully recycled after decarboxylation. The model compound 2- cyano-2-phenylpropionic acid (40) was decarboxylated with base 31a to the (S) enantiomer of the corresponding nitrile 41 with 60% ee.
- Brunner, Henri,Schmidt, Peter
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p. 2119 - 2133
(2007/10/03)
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- Synthesis and characterization of a highly potent and selective isotopically labeled retinoic acid receptor ligand, ALRT1550
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The syntheses of two labeled homologues of (2E,4E,6E)-7-(3,5-di-tert- butylphenyl)-3-methylocta-2,4,6-trienoic acid (ALRT1550, 2), [13CD3]ALRT1550 (3) and [3H]ALRT1550 (4), are described in this report. ALRT1550 is an exceptionally potent antiproliferative agent which is currently in phase I/II clinical trials for acute chemotherapy. Both homologues were prepared from commercially available 3,5-di-tert-butylbenzoic acid. Homologue [13CD3]ALRT1550 was labeled at the 7-position of the trienoic acid chain via addition of [13CD3]MgI to a Weinreb amide precursor. The preparation of [3H]ALRT1550 utilized novel methodology to synthesize a sterically hindered and site-specific tritium-labeled tert- butyl group. Saturation binding and Scatchard analysis of this ligand at the retinoic acid receptors are also described, along with competition binding (K(i)) values for a series of known retinoids using [3H]ALRT1550 or [3H]ATRA as the labeled probes.
- Bennani, Youssef L.,Marron, Kristin S.,Mais, Dale E.,Flatten, Karen,Nadzan, Alex M.,Boehm, Marcus F.
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p. 543 - 550
(2007/10/03)
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- Analogues of capsaicin with agonist activity as novel analgesic agents: Structure-activity studies. 4. Potent, orally active analgesics
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Structural features of three regions of the capsaicin molecule necessary for agonist properties were delineated by a previously reported modular approach. These in vitro agonist effects were shown to correlate with analgesic potency in rodent models. Comb
- Wrigglesworth, Roger,Walpole, Christopher S. J.,Bevan, Stuart,Campbell, Elizabeth A.,Dray, Andy,Hughes, Glyn A.,James, Iain,Masdin, Kay J.,Winter, Janet
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p. 4942 - 4951
(2007/10/03)
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- 3,5-Di-tert-butylthiobenzoyltriphenylsilane: a versatile spin trapping agent
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3,5-Di-tert-butylthiobenzoyltriphenylsilane (DBTBTPS) has been synthesized and tested as a spin trapping agent for electron spin resonance studies.Upon reaction with a variety of radicals of different nature inside the cavity of the ESR spectrometer.DBTBTPS leads to the observation of rather persistent spectra which in nearly all cases allow the unambiguous identification of the trapped species, DBTBTPS is somewhat less stable than thiobenzoyltriphenylsilane (TBTPS), the unsubstituted thiobenzoyltriphenylsilane; yet, as it affords spin adducts whose spectra are characterized by a smaller number of lines, it may prove more useful than TBTPS itself when dealing with radicals leading to species with a large number of magnetically active nuclei interacting with the unpaired electron.
- Alberti, Angelo,Benaglia, Massimo
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p. 151 - 158
(2007/10/02)
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- The synthesis of aldehydes by means of a modified Rosenmund reduction of acid chlorides
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Aliphatic as well as aromatic acid chlorides are reduced smoothly into aldehydes at room temperature and atmospheric pressure by hydrogenation, using palladium on carbon as the catalyst, acetone or ethyl acetate as solvent and ethyldiisopropylamine as hydrogen chloride acceptor.The reaction has a high selectivity and under the conditions used, no over-reduction nor reduction of aromatic rings, of nitro and chloro substituents in benzoyl chlorides, or double bonds in cinnamoyl chlorides, was observed.The selectivity is probably the result of a combination of factors, such as selective adsorption of the acid chloride on the catalyst (with respect to the aldehyde) and partial poisoning of the catalyst surface by co-adsorption of ethyldiisopropylamine and its hydrochloride.
- Peters, J. A.,Bekkum, H. van
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