cas 77119-85-8, (R)-(+)-2-(TERT-BUTOXYCARBONYLAMINO)-3-PHENYLPROPANAL

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Potent Anti-SARS-CoV-2 Activity by the Natural Product Gallinamide A and Analogues via Inhibition of Cathepsin L
Cathepsin L is a key host cysteine protease utilized by coronaviruses for cell entry and is a promising drug target for novel antivirals against SARS-CoV-2. The marine natural product gallinamide A and several synthetic analogues were identified as potent inhibitors of cathepsin L with IC50 values in the picomolar range. Lead molecules possessed selectivity over other cathepsins and alternative host proteases involved in viral entry. Gallinamide A directly interacted with cathepsin L in cells and, together with two lead analogues, potently inhibited SARS-CoV-2 infection in vitro, with EC50 values in the nanomolar range. Reduced antiviral activity was observed in cells overexpressing transmembrane protease, serine 2 (TMPRSS2); however, a synergistic improvement in antiviral activity was achieved when combined with a TMPRSS2 inhibitor. These data highlight the potential of cathepsin L as a COVID-19 drug target as well as the likely need to inhibit multiple routes of viral entry to achieve efficacy.
Aggarwal, Anupriya,Ashhurst, Anneliese S.,Bedding, Max J.,Beretta, Laura,Drelich, Aleksandra,Gerwick, William H.,Hook, Vivian,Larance, Mark,Li, Linfeng,McKerrow, James H.,Meek, Thomas D.,O'Donoghue, Anthony J.,Payne, Richard J.,Pwee, Dustin,Skinner, Danielle,Stoye, Alexander,Tang, Arthur H.,Tseng, Chien-Te,Turville, Stuart,Yoon, Michael C.,Fajtová, Pavla
(2021/11/18)

Synthesis of α-Ketoamide-Based Stereoselective Calpain-1 Inhibitors as Neuroprotective Agents
Calpain inhibitors have been proposed as drug candidates for neurodegenerative disorders, with ABT-957 entering clinical trials for Alzheimer's disease and mild cognitive impairment. The structure of ABT-957 was very recently disclosed, and trials were te
Jastaniah, Ammar,Gaisina, Irina N.,Knopp, Rachel C.,Thatcher, Gregory R. J.
p. 2280 - 2285
(2020/09/23)

Pyridone [1, 2-b] [1,5] triazepine derivatives as well as preparation and application thereof (by machine translation)
The invention discloses a hydroxypyridone [1, a-b] [1,5] triazepine derivatives as well as preparation and application thereof. Experiments prove that the hydroxypyridinone [1, 2-b] [1,triazepine derivatives (general formula I) have a good inhibition effect on the RNA polymerase activity of influenza A virus RNA, and can be used as an influenza virus RNA polymerase inhibitor to treat influenza caused by influenza virus. General Formula I is as follows. (by machine translation)
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(2020/12/30)

Design of Gallinamide A Analogs as Potent Inhibitors of the Cysteine Proteases Human Cathepsin L and Trypanosoma cruzi Cruzain
Gallinamide A, originally isolated with a modest antimalarial activity, was subsequently reisolated and characterized as a potent, selective, and irreversible inhibitor of the human cysteine protease cathepsin L. Molecular docking identified potential modifications to improve binding, which were synthesized as a suite of analogs. Resultingly, this current study produced the most potent gallinamide analog yet tested against cathepsin L (10, Ki = 0.0937 ± 0.01 nM and kinact/Ki = 8 730 000). From a protein structure and substrate preference perspective, cruzain, an essential Trypanosoma cruzi cysteine protease, is highly homologous. Our investigations revealed that gallinamide and its analogs potently inhibit cruzain and are exquisitely toxic toward T. cruzi in the intracellular amastigote stage. The most active compound, 5, had an IC50 = 5.1 ± 1.4 nM, but was relatively inactive to both the epimastigote (insect stage) and the host cell, and thus represents a new candidate for the treatment of Chagas disease.
Boudreau, Paul D.,Miller, Bailey W.,McCall, Laura-Isobel,Almaliti, Jehad,Reher, Raphael,Hirata, Ken,Le, Thu,Siqueira-Neto, Jair L.,Hook, Vivian,Gerwick, William H.
p. 9026 - 9044
(2019/10/16)

Synthesis of Enantiomerically Pure 3-Substituted Piperazine-2-acetic Acid Esters as Intermediates for Library Production
The piperazine heterocycle is broadly exploited in FDA-approved drugs and biologically active compounds, but its chemical diversity is usually limited to ring nitrogen substitutions, leaving the four carbon atoms underutilized. Using an efficient six-step synthesis, chiral amino acids were transformed into 3-substituted piperazine-2-acetic acid esters as diastereomeric mixtures whose cis and trans products (dr 0.56 a? 2.2:1, respectively) could be chromatographically separated. From five amino acids (both antipodes) was obtained a complete matrix of 20 monoprotected chiral 2,3-disubstituted piperazines, each as a single absolute stereoisomer, all but one in multigram quantities. In keeping with our overall purpose of constructing more Csp3-enriched compound libraries for drug discovery, these diverse and versatile piperazines can be functionalized on either nitrogen atom, allowing them to be used as scaffolds for parallel library synthesis and as intermediates for the production of novel piperazine compounds.
Reddy Guduru, Shiva Krishna,Chamakuri, Srinivas,Raji, Idris O.,MacKenzie, Kevin R.,Santini, Conrad,Young, Damian W.
p. 11777 - 11793
(2018/09/27)

A practical diastereoselective synthesis of (?)-bestatin
Diastereoselective addition of nitromethane to Boc-D-Phe-H in the presence of sodium hydride in diethyl ether/hexane containing 15-crown-5 and subsequent N,O-protection with 2,2-dimethoxypropane gave trans-oxazolidine in a diastereomeric ratio of >16:1. T
Shang, Suisheng,Willems, Andreas V.,Chauhan, Satendra S.
(2018/02/16)

Triazole Ureas Act as Diacylglycerol Lipase Inhibitors and Prevent Fasting-Induced Refeeding
Triazole ureas constitute a versatile class of irreversible inhibitors that target serine hydrolases in both cells and animal models. We have previously reported that triazole ureas can act as selective and CNS-active inhibitors for diacylglycerol lipases (DAGLs), enzymes responsible for the biosynthesis of 2-arachidonoylglycerol (2-AG) that activates cannabinoid CB1 receptor. Here, we report the enantio- and diastereoselective synthesis and structure-activity relationship studies. We found that 2,4-substituted triazole ureas with a biphenylmethanol group provided the most optimal scaffold. Introduction of a chiral ether substituent on the 5-position of the piperidine ring provided ultrapotent inhibitor 38 (DH376) with picomolar activity. Compound 38 temporarily reduces fasting-induced refeeding of mice, thereby emulating the effect of cannabinoid CB1-receptor inverse agonists. This was mirrored by 39 (DO34) but also by the negative control compound 40 (DO53) (which does not inhibit DAGL), which indicates the triazole ureas may affect the energy balance in mice through multiple molecular targets.
Deng, Hui,Kooijman, Sander,Van Den Nieuwendijk, Adrianus M. C. H.,Ogasawara, Daisuke,Van der Wel, Tom,Van Dalen, Floris,Baggelaar, Marc P.,Janssen, Freek J.,Van Den Berg, Richard J. B. H. N.,Den Dulk, Hans,Cravatt, Benjamin F.,Overkleeft, Herman S.,Rensen, Patrick C. N.,Van der Stelt, Mario
p. 428 - 440
(2017/04/26)

As cell necrosis inhibitors of the indole compounds (by machine translation)
The invention relates to chemical formula (1) indole compounds, or its pharmaceutically acceptable salt or isomer, and in containing the same as the characteristic, as an active ingredient for the prevention or treatment of cell necrosis and its associated disease composition and method of manufacturing. (by machine translation)
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Paragraph 0218; 0219; 0220

(2016/10/09)

INDOLE COMPOUND AS INHIBITOR OF NECROSIS
The present invention relates to an indole compound represented by formula (1), a pharmaceutically acceptable salt or isomer thereof, a composition for prevention or treatment of necrosis and necrosis-associated diseases, and a method for preparing the composition, the composition comprising the indole compound or the pharmaceutically acceptable salt or isomer thereof as an active ingredient.
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Paragraph 0189; 0190

(2016/08/17)

Highly enantioselective hydrogenation of α-oxy functionalized α,β-unsaturated acids catalyzed by a ChenPhos-Rh complex in CF3CH2OH
Rhodium complexes coordinated by Chenphos are very effective catalysts for the enantioselective hydrogenation of α-aryloxy- and α-alkoxy-substituted α,β-unsaturated carboxylic acids under mild conditions in CF3CH2OH. The catalytic system could be successfully employed in building the core structure of a new FDA approved drug LCZ 696.
Yao, Lin,Wen, Jialin,Liu, Shaodong,Tan, Renchang,Wood, Noel Marie,Chen, Weiping,Zhang, Shengyong,Zhang, Xumu
supporting information
p. 2273 - 2276
(2016/02/18)

Binding cooperativity between a ligand carbonyl group and a hydrophobic side chain can be enhanced by additional H-bonds in a distance dependent manner: A case study with thrombin inhibitors
One of the underappreciated non-covalent binding factors, which can significantly affect ligand-protein binding affinity, is the cooperativity between ligand functional groups. Using four different series of thrombin inhibitors, we reveal a strong positiv
Said, Ahmed M.,Hangauer, David G.
p. 405 - 424
(2015/05/05)

Rational construction of triazole/urea based peptidomimetic macrocycles as pseudocyclo-β-peptides and studies on their chirality controlled self-assembly
A tandem macro-dimerization reaction via a Cu(I) catalyzed azide/alkyne cycloaddition reaction has been employed to construct triazole/urea based peptidomimetic macrocycles considered as pseudocyclo-β-peptides. Introduction of one particular chirality in
Ghorai, Abhijit,Reddy K, Samanth,Achari, Basudeb,Chattopadhyay, Partha
p. 3196 - 3199
(2014/07/08)

Nonpeptidic lysosomal modulators derived from Z-Phe-Ala-diazomethylketone for treating protein accumulation diseases
Lysosomes are involved in protein turnover and removing misfolded species, and their enzymes have the potential to offset the defect in proteolytic clearance that contributes to the age-related dementia Alzheimer's disease (AD). The weak cathepsin B and L
Viswanathan, Kishore,Hoover, Dennis J.,Hwang, Jeannie,Wisniewski, Meagan L.,Ikonne, Uzoma S.,Bahr, Ben A.,Wright, Dennis L.
p. 920 - 924
(2013/01/15)

NOVEL COMPOUNDS FOR MODULATION OF ORPHAN NUCLEAR RECEPTOR RAR-RELATED ORPHAN RECEPTOR-GAMMA (RORγ GAMMA, NR1F3) ACTIVITY AND FOR THE TREATMENT OF CHRONIC INFLAMMATORY AND AUTOIMMUNE DISEASE
The invention provides modulators for the orphan nuclear receptor RORγ and methods for treating RORγ mediated diseases by administrating these novel RORγ modulators to a human or a mammal in need thereof. Specifically, the present invention provides compounds of Formula (1) and the enantiomers, diastereomers, tautomers, solvates and pharmaceutically acceptable salts thereof.
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Page/Page column 68; 69

(2011/10/03)

Synthesis of new (-)-bestatin-based inhibitor libraries reveals a novel binding mode in the S1 pocket of the essential malaria M1 metalloaminopeptidase
The malarial PfA-M1 metallo-aminopeptidase is considered a putative drug target. The natural product dipeptide mimetic, bestatin, is a potent inhibitor of PfA-M1. Herein we present a new, efficient, and high-yielding protocol for the synthesis of bestatin derivatives from natural and unnatural N-Boc-d-amino acids. A diverse library of bestatin derivatives was synthesized with variants at the side chain of either the α-hydroxyβ-amino acid (P1) or the adjacent naturalα-amino acid (P1′). Surprisingly, we found that extended aromatic side chains at the P1 position resulted in potent inhibition against PfA-M1. To understand these data, we determined the X-ray cocrystal structures of PfA-M1 with two derivatives having either a Tyr(OMe) 15 or Tyr(OBzl) 16 at the P1 position and observed substantial inhibitor-induced rearrangement of the primary loop within the PfA-M1 pocket that interacts with the P1 side chain. Our data provide important insights for the rational design of more potent and selective inhibitors of this enzyme that may eventually lead to new therapies for malaria.
Velmourougane, Geetha,Harbut, Michael B.,Dalal, Seema,McGowan, Sheena,Oellig, Christine A.,Meinhardt, Nataline,Whisstock, James C.,Klemba, Michael,Greenbaum, Doron C.
p. 1655 - 1666
(2011/05/16)

Deglycobleomycin A6 analogues modified in the methylvalerate moiety
Previous studies have indicated that the methylvalerate subunit of bleomycin (BLM) plays an important role in facilitating DNA cleavage by BLM and deglycoBLM. Eleven methylvalerate analogues have been synthesized and incorporated into deglycoBLM congeners by the use of solid-phase synthesis. The effect of the valerate moiety in the deglycoBLM analogues has been studied by comparison with the parent deglycoBLM A5 using supercoiled DNA relaxation and sequence-selective DNA cleavage assays. All of the deglycoBLM analogues were found to effect the relaxation of the plasmid DNA. Those analogues having aromatic C4-substituents exhibited cleavage efficiency comparable to that of deglycoBLM A5. Some, but not all, of the deglycoBLM analogues were also capable of mediating sequence-selective DNA cleavage.
Cai, Xiaoqing,Zaleski, Paul A.,Cagir, Ali,Hecht, Sidney M.
p. 3831 - 3844
(2011/08/02)

Preparation of α-hydroxy-β-Fmoc amino acids from N-Boc amino acids
A general method for the conversion of N-Boc amino acids into their homologated α-hydroxy-β-Fmoc amino acids is described. The protocol involved preparation of the amino aldehyde by reduction of the corresponding Weinreb amides, hydrocyanation, and hydrol
Johnson, Erik P.,Hubieki, M. Patricia,Combs, Andrew P.,Teleha, Christopher A.
p. 4023 - 4026
(2012/01/12)

Synthesis and evaluation of inhibitors of cytochrome P450 3A (CYP3A) for pharmacokinetic enhancement of drugs
The HIV protease inhibitor ritonavir (RTV) is also a potent inhibitor of the metabolizing enzyme cytochrome P450 3A (CYP3A) and is clinically useful in HIV therapy in its ability to enhance human plasma levels of other HIV protease inhibitors (PIs). A nov
Flentge, Charles A.,Randolph, John T.,Huang, Peggy P.,Klein, Larry L.,Marsh, Kennan C.,Harlan, John E.,Kempf, Dale J.
supporting information; experimental part
p. 5444 - 5448
(2010/05/02)

Structure-activity relationship of 2-oxoamide inhibition of group IVA cytosolic phospholipase A2 and group V secreted phospholipase A 2
The Group IVA cytosolic phospholipase A2 (GIVA cPLA2) is a key provider of substrates for the production of eicosanoids and platelet-activating factor. We explored the structure-activity relationship of 2-oxoamide-based compounds and
Six, David A.,Barbayianni, Efrosini,Loukas, Vassilios,Constantinou-Kokotou, Violetta,Hadjipavlou-Litina, Dimitra,Stephens, Daren,Wong, Alan C.,Magrioti, Victoria,Moutevelis-Minakakis, Panagiota,Baker, Sharon F.,Dennis, Edward A.,Kokotos, George
p. 4222 - 4235
(2008/02/11)

Synthesis and dipeptidyl peptidase inhibition of N-(4-substituted-2,4-diaminobutanoyl)piperidines
In this paper, we report the synthesis of diastereomerically pure N-(4-substituted-2,4-diaminobutanoyl)piperidines. These compounds were prepared to investigate the influence of the 4-substitution on the dipeptidyl peptidase II (DPP II) activity and selectivity of the parent N-(2,4-diaminobutanoyl)piperidine. The (4S)-methyl compound showed subnanomolar inhibition, comparable with the parent compound. The (4R)-methyl group or bigger substituents decreased the activity.
Soroka, Anna,der Veken, Pieter Van,Meester, Ingrid De,Lambeir, Anne-Marie,Maes, Marie-Berthe,Scharpe, Simon,Haemers, Achiel,Augustyns, Koen
p. 4777 - 4779
(2007/10/03)

NK-2 ANTAGONIST BASIC LINEAR COMPOUNDS AND FORMULATIONS CONTAINING THEM
The present invention describes compounds with formula (I) having linear structure basic properties useful as NK-2 antagonists; pharmaceutical compositions containing said compounds are also described and processes for their preparation.
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Page 10

(2010/02/09)

Stereochemical analysis of (hydroxyethyl)urea peptidomimetic inhibitors of γ-secretase
(Hydroxyethyl)urea peptidomimetics systematically altered at positions P2-P3′ with hydrophobic D-amino acids were synthesized. An all D-amino acid containing analogue was identified that effectively blocked γ-secretase activity in a cell-free system (IC50 = 30 nM). Systematic alteration of the stereocenters of a potent compound revealed interdependence between the various positions. Although typically less potent than their L-peptidomimetic counterparts, selected all D-amino acid containing analogues were equipotent to their counterparts in a cell-based assay when incubated for extended times.
Bakshi, Pancham,Wolfe, Michael S.
p. 6485 - 6489
(2007/10/03)

Diastereoselective Synthesis of ψ[(E)-CH=CMe]- and ψ[(Z)-CH=CMe]-Type Dipeptide Isosteres by Organocopper-mediated anti-SN2′ Reaction
matrix presented Acyclic ψ[(E)-CH=CMe]- and ψ[(Z)-CH=CMe]-type dipeptide isosteres were efficiently synthesized. In a key reaction, α-alkylation of γ-mesyloxy-β-methyl-α,β-unsaturated esters with organocyanocuprates in diethyl ether or tetrahydrofuran preferentially afforded the ψ[(E)-CH=CMe]- or ψ[(Z)-CH=CMe]-isomer, respectively, via anti-SN2′ mechanism.
Oishi, Shinya,Kamano, Takae,Niida, Ayumu,Odagaki, Yoshihiko,Tamamura, Hirokazu,Otaka, Akira,Hamanaka, Nobuyuki,Fujii, Nobutaka
p. 1051 - 1054
(2007/10/03)

Diastereoselective synthesis of new psi[(E)-CH=CMe]- and psi[(Z)-CH=CMe]-type alkene dipeptide isosteres by organocopper reagents and application to conformationally restricted cyclic RGD peptidomimetics.
Diastereoselective synthesis of new psi[(E)-CH=CMe]- and psi[(Z)-CH=CMe]-type alkene dipeptide isosteres corresponding to dipeptides having one N-methylamino acid, and application to bioactive peptides, are described. In a key reaction introducing the chiral alpha-alkyl group of the isosteres, organocopper-mediated alkylation of syn-beta-methylated gamma-mesyloxy-alpha,beta-enoate 26a afforded E- and Z-isomers of anti-S(N)2' products in a solvent-dependent manner. The resulting two isosteres, D-Phe-psi[(E)-CH=CMe]-L-Val 27a and D-Phe-psi[(Z)-CH=CMe]-L-Val 28b, which corresponded to trans- and cis-conformers of D-Phe-L-MeVal, respectively, were utilized in a structure-activity relationship study on cyclic RGD peptides 1 and 2, in company with a psi[(E)-CH=CH]-type alkene dipeptide isostere, D-Phe-psi[(E)-CH=CH]-L-Val. The cyclic isostere-containing pseudopeptides 3, 4, and 40 were synthesized and biological activity against integrin alpha(V)beta(3) and alpha(IIb)beta(3) receptors were also evaluated.
Oishi, Shinya,Kamano, Takae,Niida, Ayumu,Odagaki, Yoshihiko,Hamanaka, Nobuyuki,Yamamoto, Mikio,Ajito, Keiichi,Tamamura, Hirokazu,Otaka, Akira,Fujii, Nobutaka
p. 6162 - 6173
(2007/10/03)

Regiospecific ring-opening reactions of β-aziridinyl ct, β-enoates with acids: Application to the stereoselective synthesis of a couple of diastereoisomeric (Zi)-alkene dipeptide isosteres from a single β-aziridinyl a, β-enoate and to the convenient preparation of amino alcohols bearing a, β-unsaturated ester groups
Regio- and stereo-selective ring-opening reactions of N-(2, 4, 6-trimethylphenylsulfonyl)-γ, δ-cis- or trans-γ, δ-epimino (E)-α, β-enoates with acids such as methanesulfonic acid (MSA) or trifluoroacetic acid (TFA) have been found. These ring-opening reactions are useful for the stereoselective synthesis of a couple of diastereomeric (￡)-alkene dipeptide isosteres from a single substrate of γ, δ-epimino (E)-α, β-enoate, and for the convenient preparation of δ-aminated γ-hydroxy α, β-enoates. The Royal Society of Chemistry 1999.
Tamamura, Hirokazu,Yamashita, Masaki,Nakajima, Yutaka,Sakano, Kyoko,Otaka, Akira,Ohno, Hiroaki,Ibuka, Toshiro,Fujii, Nobutaka
p. 2983 - 2996
(2007/10/03)

Amino acids and peptides. LIII. Synthesis and biological activities of some pseudo-peptide analogs of PKSI-527, a plasma kallikrein selective inhibitor: The importance of the peptide backbone
Pseudo-peptide analogs of trans-4-aminomethylcyclohexanecarbonyl-L- phenylalanyl-4-aminophenyl acetic acid (PKSI-527, plasma kallikrein selective inhibitor), in which an amide bond (peptide bond) has been replaced by a CH2-NH bond, i.e. trans-4
Fukumizu, Atsuko,Tsuda, Yuko
p. 1141 - 1144
(2007/10/03)

Synthesis of chiral vinylogous sulfonamidopeptides (vs-peptides)
Chiral vinylogous amino sulfonic acids (vs-amino acids) were synthesized starting from either L- or D-α-amino acids via N-Boc-α-amino aldehydes. Wittig-Horner reaction with methyl (or ethyl) diethylphosphoryl methanesulfonate and nBuLi gave the corresponding α,β-unsaturated sulfonates in high yield and complete (E) stereoselectivity. Cleavage of the methyl (ethyl) ester was effected by treatment of the sulfonates with nBu4NI in refluxing acetone. Treatment of the nBu4N+ sulfonate salts with SO2Cl2/PPh3/CH2Cl2 gave the corresponding sulfonyl chlorides as stable chromatographable compounds. The synthetic sequence proved successful not only starting from α-amino acids carrying unfunctionalized side-chains (Ala, Val, Phe, Leu, Pro), but also with functionalized α-amino acids (Ser, Tyr, Gln) provided that the side chains were suitably protected. The sulfonyl chlorides were coupled with the amine salts to give vs-dipeptides. Amine hydrochlorides were prepared from N-Boc derivatives by treatment with HCl in methanol or ethyl acetate. The process was further iterated to give vstripeptides and vs-tetrapeptides. The above procedure was also used to synthesize "mixed" peptides, which incorporate both proteinogenic α-amino acids and vs-amino acids. Proteinogenic α-amino acids were incorporated at both the C-terminal and the N-terminal position.
Gennari, Cesare,Longari, Chiara,Ressel, Stefano,Salom, Barbara,Mielgo, Antonia
p. 945 - 959
(2007/10/03)

A novel synthesis of 1,3-benzodiazepin-2-ones using intramolecular heck reaction
The formation of the skeleton of 1,3-benzodiazepin-2-one could be efficiently achieved by intramolecular Heck reaction. This methodology was well applicable to the preparation of optically pure 4-substituted 1,3-benzodiazepin-2-ones starting from easily available α-amino acids.
Hayashi, Masahito,Sai, Hiroshi,Horikawa, Hiroshi
p. 1331 - 1335
(2007/10/03)

Stereoselective synthesis of 2-amino-1-hydroxy-3-phenylpropylphosphonic acid
A highly stereoselective synthesis of 2-amino-1-hydroxy-3-phenylpropylphosphonic acid was achieved by simple addition of diethyl phosphite to enantiomeric N-blocked phenylalaninals. These compounds exhibit significant herbicidal activity.
Zygmunt, Jan,Gancarz, Roman,Lejczak, Barbara,Wieczorek, Piotr,Kafarski, Pawel
p. 2989 - 2992
(2007/10/03)

Alkylation of camphor and pinanone imines of 2-(aminomethyl)thiazole. Enantioselective synthesis of 2-(1-aminoalkyl)thiazoles
A method is described for the enantioselective synthesis of 2-(1-aminoalkyl)thiazoles 6 via stereoselective alkylation of the carbanions of (+)-(R)-camphor and (-)-(1S, 2S, 5S)-2-hydroxypinan-3-one imines 2 and 3 derived from 2-(aminomethyl)thiazole (2-AMT, 1). Compounds 6 serve as α-amino aldehyde precursors via thiazolyl-to-formyl conversion.
Dondoni, Alessandro,Merchan, Francisco L.,Merino, Pedro,Rojo, Isabel,Tejero, Tomas
p. 641 - 646
(2007/10/03)

The Influence of Protecting Group Character on the Diastereoselectivity of Thiazolidine Ring Formation from Amino Aldehydes and Cysteine
A series of 2-(1'-aminoalkyl)-thiazolidine-4-carboxylic acid derivatives was synthesized by condensation of (R)- or (S)-Cys with the amino aldehydes obtained from N-Boc-protected (S)-Ile, (S)-Leu, O-Bzl-(S)-Tyr, (S)- and (R)-Phe, and N-Z-(S)-Phe, N-Pht-(S)-Phe and N-(Pht)-(R)-Phe. All compounds were studied by 1H NMR and CD. The 2D NOESY experiments were carried out to determine the configuration of the newly formed stereogenic centre in position 2 of the thiazolidine ring. It was found that the configuration on the thiazolidine C2 atom is R or S when N-Boc- and N-Z-(S)-amino aldehydes or N-Boc- and N-Z-(R)-amino aldehydes are used in the reaction, respectively. The situation is opposite in the case of N-Pht-Phe derived amino aldehydes. The relation between the C2 atom configuration and the shape of CD spectra is discussed. Key words: 2-(1'-aminoalkyl)-thiazolidine-4-carboxylic acids, amino aldehydes, cysteine, stereoselectivity, absolute configuration, NMR, CD.
Wyslouch, Aleksandra,Lisowski, Marek,Siemion, Ignacy Z.
p. 117 - 130
(2007/10/02)

Stereospecific Synthesis of Peptidyl α-Keto Amides as Inhibitors of Calpain
Peptidyl α-keto amides have been synthesized and tested as inhibitors of the cysteine protease calpain.A stereospecific synthesis was devised in which Cbz-dipeptidyl-α-hydroxy amides were oxidized with TEMPO/hypochlorite to the corresponding α-keto amides
Harbeson, Scott L.,Abelleira, Susan M.,Akiyama, Alan,Barrett, Robert,Carroll, Renee M.,et al.
p. 2918 - 2929
(2007/10/02)

Development of selective tight-binding inhibitors of leukotriene A4 hydrolase
Leukotriene A4 hydrolase is a zinc-containing enzyme which exhibits both epoxide hydrolase and aminopeptidase activities. Since the enzyme product leukotriene B4 is an inflammatory mediator, it is of interest to develop selective inh
Yuan,Munoz,Wong,Haeggstrom,Wetterholm,Samuelsson
p. 211 - 220
(2007/10/02)

Development of methodology for the synthesis of stereochemically pure PheΨ[CH2N]Pro linkages in HIV protease inhibitors
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Cushman,Oh,Copeland,Oroszlan,Snyder
p. 4161 - 4167
(2007/10/02)