- An irreversible inhibitor of peptidyl-prolyl cis/trans isomerase Pin1 and evaluation of cytotoxicity
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Pin1 (protein interacting with never in mitosis A-1) is a member of the peptidyl prolyl isomerase (PPIase) family, and catalyzes cis-trans isomerization of pThr/Ser-Pro amide bonds. Because Pin1 is overexpressed in various cancer cell lines and promotes c
- Ieda, Naoya,Itoh, Kaoru,Inoue, Yasumichi,Izumiya, Yusuke,Kawaguchi, Mitusyasu,Miyata, Naoki,Nakagawa, Hidehiko
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Read Online
- Visible-Light Photoredox Synthesis of Chiral α-Selenoamino Acids
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N-Acetoxyphthalimide derivatives of two genetically coded proteinogenic amino acids, l-aspartic acid and glutamic acid, were used as visible light photoredox chiral sources and radical precursors, diorganyl diselenides were used as the radical acceptors,
- Jiang, Min,Yang, Haijun,Fu, Hua
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Read Online
- Synthesis of l -Kynurenine and Homo- l -Kynurenine via an Aza-Fries Rearrangement
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l -Kynurenine, a non-proteinogenic amino acid, is the primary metabolite of tryptophan via the kynurenine pathway. Kynurenine is involved in a variety of biological processes occurring in the human body, notably in the central nervous system. Thus, the st
- Bonilla-Reyes, Edgar,Sánchez-Carrillo, Adrian,Vázquez, Alfredo
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p. 3473 - 3479
(2020/09/15)
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- Dearomatization of 3-Nitroindoles with Highly γ-Functionalized Allenoates in Formal (3+2) Cycloadditions
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3-Nitroindoles are easily reacted with highly substituted γ-allenoates in the presence of a commercially available phosphine catalyst. For instance, allenoates derived from biomolecules such as amino and deoxycholic acids are combined for the first time w
- Birbaum, Léo,Gillard, Laurent,Gérard, Hélène,Oulyadi, Hassan,Vincent, Guillaume,Moreau, Xavier,De Paolis, Michael,Chataigner, Isabelle
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supporting information
p. 13688 - 13693
(2019/11/03)
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- Oxadiazole-Based Cell Permeable Macrocyclic Transition State Inhibitors of Norovirus 3CL Protease
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Human noroviruses are the primary causative agents of acute gastroenteritis and a pressing public health burden worldwide. There are currently no vaccines or small molecule therapeutics available for the treatment or prophylaxis of norovirus infections. Norovirus 3CL protease plays a vital role in viral replication by generating structural and nonstructural proteins via the cleavage of the viral polyprotein. Thus, molecules that inhibit the viral protease may have potential therapeutic value. We describe herein the structure-based design, synthesis, and in vitro and cell-based evaluation of the first class of oxadiazole-based, permeable macrocyclic inhibitors of norovirus 3CL protease.
- Damalanka, Vishnu C.,Kim, Yunjeong,Alliston, Kevin R.,Weerawarna, Pathum M.,Galasiti Kankanamalage, Anushka C.,Lushington, Gerald H.,Mehzabeen, Nurjahan,Battaile, Kevin P.,Lovell, Scott,Chang, Kyeong-Ok,Groutas, William C.
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p. 1899 - 1913
(2016/03/22)
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- Synthesis of rhodotorulic acid and its 1,4-dimethylated derivative
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Facile syntheses of rhodotorulic acid, isolated from Rhodotorula pilimanae as a siderophore, and its 1,4-dimethylated derivative have been achieved by microwave-assisted cyclization of the corresponding dipeptide precursors.
- Nakao, Michiyasu,Fukayama, Shintaro,Kitaike, Syuji,Sano, Shigeki
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p. 1309 - 1316
(2015/03/04)
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- Synthesis of triazole cages containing C3-symmetric α-cyclic tripeptide scaffold
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Two water-soluble C3-symmetric 1,2,3-triazole cages containing α-cyclic tripeptide were efficiently synthesized. The key steps include a click reaction to incorporate l-glutamic or l-aspartic acids to a tripodal linker and a unique one-pot cyclotrimerization.
- Chakraborty, Subrata,Tai, Dar-Fu
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supporting information
p. 2274 - 2276
(2014/04/17)
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- BORON CONTAINING POLYBASIC BACTERIAL EFFLUX PUMP INHIBITORS AND THERAPEUTICS USES THEREOF
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Disclosed herein are polybasic bacterial efflux pump inhibitors containing boronic acid functionality and theft methods of synthesis, methods of use, and pharmaceutical compositions. Some embodiments include methods of treating or preventing a bacterial infection by co-administering to a subject infected with bacteria or at risk of infection with bacteria the efflux pump inhibitor with another anti-bacterial agent
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Page/Page column 39
(2012/08/28)
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- PYRIDINE DERIVATIVES SUBSTITUTED WITH HETEROCYCLIC RING AND gamma-GLUTAMYLAMINO GROUP, AND ANTIFUNGAL AGENTS CONTAINING SAME
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The present invention provides an antifungal agent which has excellent antifungal action, and which is also excellent in terms of its properties, and in particular its solubility in water and safety. The present invention discloses a compound represented
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Page/Page column 32
(2010/05/13)
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- POLYBASIC BACTERIAL EFFLUX PUMP INHIBITORS AND THERAPEUTIC USES THEREOF
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Disclosed are compounds having polybasic functionalities. The compounds inhibit bacterial efflux pump inhibitors and are used in combination with an anti-bacterial agent to treat or prevent bacterial infections. These combinations can be effective against bacterial infections that have developed resistance to anti-bacterial agents through an efflux pump mechanism.
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Page/Page column 41-42
(2009/01/24)
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- Design and synthesis of all diastereomers of cyclic pseudo-dipeptides as mimics of cyclic CXCR4 pentapeptide antagonists
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The four diastereomers of 2,5-bis[(3-guanidino)propyl]-1-[3-(4- hydroxyphenyl)propionyl]-7-(2-naphthylacetyl)-1,4,7-triazacycloundec-9-en-3-one (54-57) and of 2,5-bis[(3-guanidino)propyl]-1-(4-hydroxyphenylacetyl)-7-(2- naphthylacetyl)-1,4,7-triazacycloundec-9-en-3-one (58-61) were synthesized by a divergent methodology from l- and d-glutamic acids. The 11-membered ring core was made by ring closing metathesis of linear bis(allylamines), and the guanidyl functions were introduced by a simultaneous double Mitsunobu reaction using bis(Boc)guanidine. These compounds were designed to mimic cyclic pentapeptide FC131 (c[Gly-d-Tyr-Arg-Arg-Nal]). The Royal Society of Chemistry.
- Cluzeau, Jerome,Oishi, Shinya,Ohno, Hiroaki,Wang, Zixuan,Evans, Barry,Peiper, Stephen C.,Fujii, Nobutaka
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p. 1915 - 1923
(2008/02/10)
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- Synthesis, characterization and cytolytic activity of α-helical amphiphilic peptide nanostructures containing crown ethers
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Many natural α-helical amphiphilic peptides are known to have lytic activity toward different cells. Herein, we describe the synthesis and the characterization of synthetic α-helical amphiphilic peptide nanostructures containing crown ethers, as well as t
- Boudreault, Pierre-Luc,Voyer, Normand
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p. 1459 - 1465
(2008/02/08)
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- Synthesis of cationic porphyrin modified amino acids
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Derivatives of amino acids bearing a porphyrin moiety on a side chain were synthesized by coupling a porphyrin to a glutamic acid side chain; the utility of these compounds was demonstrated by their use in solid-phase synthesis of a peptide bearing a cati
- Biron, Eric,Voyer, Normand
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p. 4652 - 4654
(2007/10/03)
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- Photolysis of diacyl peroxides: A radical-based approach for the synthesis of functionalized amino acids
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(Matrix presented) Photolysis of the amino acid derived symmetrical and unsymmetrical diacyl peroxides at 254 nm at low temperature (-78 to -196°C) generates various bis(amino acids) in a concise manner and with orthogonal protection. The methodology was
- Spantulescu, M. Daniel,Jain, Rajendra P.,Derksen, Darren J.,Vederas, John C.
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p. 2963 - 2965
(2007/10/03)
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- Effective gelation of water using a series of bis-urea dicarboxylic acids
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At concentrations as low as 0. 3 wt % a novel family of bis-urea dicarboxylic acids gel water (see picture). The aggregation state (vesicles, gel, or fibers) depends on the pH, the ionic strength, and the molecular weight of the gelator. In this way, the gelation properties of an aqueous system are controlled by the molecular design.
- Estroff, Lara A.,Hamilton, Andrew D.
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p. 3447 - 3450
(2007/10/03)
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- Synthesis of new perhydro-(1,4)-diazepin-2-ones as constrained peptidomimetics
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New access to substituted perhydro-(1,4)-diazepin-2-ones has been developed through either a Mitsunobu reaction or an amide bond formation for the cyclisation key step.
- Nouvet, Andre,Lamaty, Frederic,Lazaro, Rene
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p. 2099 - 2102
(2007/10/03)
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- Rational design, synthesis, and serine protease inhibitory activity of a novel P1-argininal derivative featuring a conformationally constrained P2-P3 bicyclic lactam moiety
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Based on molecular modeling and judicious combination of the salient topographic features of the recently discovered P3-lactam derivative 1 with the P2-prolyl derivatives 2a,b, the novel thrombin inhibitor 3a was designed. Inhibitor 3a incorporates a fused bicyclic lactam as a novel type of P2-P3 dipeptide surrogate. The synthesis and biological activity of this potent serine protease inhibitor is presented.
- Tamura, Susan Y.,Goldman, Erick A.,Brunck, Terence K.,Ripka, William C.,Semple, J. Edward
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p. 331 - 336
(2007/10/03)
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- Non-glutamate type pyrrolo[2,3-d]pyrimidine antifolates. II. Synthesis and antitumor activity of N5-substituted glutamine analogs
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The glutamic acid moiety of N-[4-[3-(2,4-diamino-7H-pyrrolo[2,3- d]pyrimidin-5-yl)propyl]benzoyl]-L-glutamic acid (1b, TNP-351) and related compounds was replaced with some N5-substituted glutamines. Antifolates (4A-S) were effectively prepared
- Itoh, Fumio,Yoshioka, Yoshio,Yukishige, Koichi,Yoshida, Sei,Wajima, Megumi,Ootsu, Koichiro,Akimoto, Hiroshi
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p. 1498 - 1509
(2007/10/03)
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- Synthesis of a Novel Class of Peptides: Dilactam-Bridged Tetrapeptides
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As model compounds for the study of constrained peptides, the following lactam-bridged derivatives were synthesized: Ac-L--D--NHMe (I), Ac-L--L--NHMe (II), Ac-L--NHMe (III), Ac-L--D--NHMe (IV), Ac-L--L--NHMe (V), and Ac-L--NHMe (VI).Benzyloxycarbonyl and tert-butyloxycarbonyl groups were employed for amine protection and the benzyl and methyl esters for carboxyl protection.Coupling reactions were carried out by the use of active esters or through azide activation.Cyclization reactions were carried out by adding the active ester hydrochlorides into large volumes of pyridine at elevated temperatures.The cyclic intermediates were obtained in yields of 45-50percent.Fragment condensation of the cyclic dipeptides yielded the corresponding dilactam-bridged tetrapeptides.
- Manesis, Nick J.,Goodman, Murray
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p. 5331 - 5341
(2007/10/02)
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