Home / Articles / Diazocarbonyl derivatives of amino acids: unique chiral building blocks for the synthesis of biologically active compounds

Diazocarbonyl derivatives of amino acids: unique chiral building blocks for the synthesis of biologically active compounds

Danil Petrovich Zarezin 1
Danil Petrovich Zarezin
, 
Valentin Georgievich Nenajdenko 1
Valentin Georgievich Nenajdenko
1 Lomonosov Moscow State University, Faculty of Chemistry
10.1070/RCR4852
Published 30 November 2018
Review , RCR4852, Volume 88, Issue 3, 248-279
13
Share
Cite this
GOST
 | 
Cite this
GOST
Copy cite
Zarezin D. P., Nenajdenko V. G. Diazocarbonyl derivatives of amino acids: unique chiral building blocks for the synthesis of biologically active compounds // Russian Chemical Reviews. 2018. Vol. 88. No. 3. pp. 248-279.
GOST all authors (up to 50)
Copy cite
Zarezin D. P., Nenajdenko V. G. Diazocarbonyl derivatives of amino acids: unique chiral building blocks for the synthesis of biologically active compounds // Russian Chemical Reviews. 2018. Vol. 88. No. 3. pp. 248-279.
RIS
 | 
Cite this
RIS
Copy cite
TY - JOUR
DO - 10.1070/RCR4852
UR - https://rcr.colab.ws/publications/10.1070/RCR4852
TI - Diazocarbonyl derivatives of amino acids: unique chiral building blocks for the synthesis of biologically active compounds
T2 - Russian Chemical Reviews
AU - Zarezin, Danil Petrovich
AU - Nenajdenko, Valentin Georgievich
PY - 2018
DA - 2018/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 248-279
IS - 3
VL - 88
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors)
Copy cite
@article{2018_Zarezin,
author = {Danil Petrovich Zarezin and Valentin Georgievich Nenajdenko},
title = {Diazocarbonyl derivatives of amino acids: unique chiral building blocks for the synthesis of biologically active compounds},
journal = {Russian Chemical Reviews},
year = {2018},
volume = {88},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RCR4852},
number = {3},
pages = {248--279},
doi = {10.1070/RCR4852}
}
MLA
Cite this
MLA
Copy cite
Zarezin, Danil Petrovich, and Valentin Georgievich Nenajdenko. “Diazocarbonyl derivatives of amino acids: unique chiral building blocks for the synthesis of biologically active compounds.” Russian Chemical Reviews, vol. 88, no. 3, Nov. 2018, pp. 248-279. https://rcr.colab.ws/publications/10.1070/RCR4852.
Views / Visits / Downloads
31 / 30 / 6

Keywords

aminodiazoketones
depsipeptides
lactams
peptides

Abstract

This review deals with applications of chiral $\alpha$-amino diazoketones, $\alpha$-amino acid derivatives, in the synthesis of various biologically active compounds. General approaches to the synthesis of chiral $\alpha$-amino diazoketones, including the Arndt--Eistert reaction, acylation of trimethylsilyldiazomethanes, \textit{etc}., are discussed. Due to the presence of three functional groups, these building blocks can be used to produce a wide range of organic compounds with potential physiological activity, ranging from various heterocyclic compounds to peptidomimetics. Methods for the synthesis of $\beta$-amino acid-containing peptides and depsipeptides, amino acid derivatives and heterocyclic compounds with three- to seven-membered rings are considered.

The bibliography includes 226 references.

Funders

Ministry of Education and Science of the Russian Federation
НШ-4687.2018.3

References

1.
Modern Organic Synthesis with α-Diazocarbonyl Compounds
Ford A., Miel H., Ring A., Slattery C.N., Maguire A.R., McKervey M.A.
Chemical Reviews , 2015
3.
rcr_88_3_248_bib3
Seebach
1997
5.
Ein Verfahren zur berfhrung von Carbonsuren in ihre hheren Homologen bzw. deren Derivate
Arndt F., Eistert B.
Berichte der deutschen chemischen Gesellschaft (A and B Series) , 1935
6.
N-Methyl-N-nosyl-β3-amino Acids
Belsito E., Di Gioia M.L., Greco A., Leggio A., Liguori A., Perri F., Siciliano C., Viscomi M.C.
Journal of Organic Chemistry , 2007
7.
N-Methyl Scan of Somatostatin Octapeptide Agonists Produces Interesting Effects on Receptor Subtype Specificity
Rajeswaran W.G., Hocart S.J., Murphy W.A., Taylor J.E., Coy D.H.
Journal of Medicinal Chemistry , 2001
9.
A One-Pot Procedure for the Preparation ofN-9-Fluorenylmethyloxycarbonyl-α-amino Diazoketones from α-Amino Acids
Siciliano C., De Marco R., Guidi L.E., Spinella M., Liguori A.
Journal of Organic Chemistry , 2012
10.
rcr_88_3_248_bib10
Wang
1998
11.
rcr_88_3_248_bib11
Villani
J. Labelled Compd. Radiopharm. , 1996
14.
Polypeptides and 100 Years of Chemistry of α-Amino AcidN-Carboxyanhydrides
Kricheldorf H.R.
Angewandte Chemie - International Edition , 2006
15.
rcr_88_3_248_bib15
Leggio
1997
18.
Use of Mixed Carboxylic-Carbonic Anhydrides for Acylations on Carbon and Oxygen1
TARBELL D.S., PRICE J.A.
Journal of Organic Chemistry , 1957
21.
Synthesis of glycosylated β3-homo-threonine conjugates for mucin-like glycopeptide antigen analogues
Karch F., Hoffmann-Röder A.
Beilstein Journal of Organic Chemistry , 2010
22.
rcr_88_3_248_bib22
Kantharaju
Indian J. Chem., Sect. B , 2004
23.
rcr_88_3_248_bib23
Vasanthakumar
2002
24.
rcr_88_3_248_bib24
Suresh Babu
Lett. Pept. Sci. , 1999
27.
rcr_88_3_248_bib27
Bodanszky
1984
28.
rcr_88_3_248_bib28
Ananda
Indian J. Chem., Sect. B , 1999
29.
rcr_88_3_248_bib29
Vasanthakumar
Indian J. Chem., Sect. B , 2003
31.
rcr_88_3_248_bib31
de Boer
Org. Synth. , 1963
33.
Synthesis of enantiomerically pure δ-benzylproline derivatives
Rodríguez I., Calaza M.I., Jiménez A.I., Cativiela C.
New Journal of Chemistry , 2015
35.
Cyclopropanones. V. Inhibition of Polymerization and Addition of Acids
Turro N.J., Hammond W.B.
Journal of the American Chemical Society , 1967
38.
β2‐ and β3‐Peptides with Proteinaceous Side Chains: Synthesis and solution structures of constitutional isomers, a novel helical secondary structure and the influence of solvation and hydrophobic interactions on folding
Seebach D., Abele S., Gademann K., Guichard G., Hintermann T., Jaun B., Matthews J.L., Schreiber J.V., Oberer L., Hommel U., Widmer H.
Helvetica Chimica Acta , 1998
39.
Probing the Helical Secondary Structure of Short‐Chain β‐Peptides
Seebach D., Ciceri P.E., Overhand M., Jaun B., Rigo D., Oberer L., Hommel U., Amstutz R., Widmer H.
Helvetica Chimica Acta , 1996
40.
rcr_88_3_248_bib40
Drey
1982
42.
Synthesis of gastrin antagonists, analogs of the C-terminal tetrapeptide of gastrin, by introduction of a .beta.-homo residue
Rodriguez M., Fulcrand P., Laur J., Aumelas A., Bali J.P., Martinez J.
Journal of Medicinal Chemistry , 1989
43.
SAR studies on dihydropyrimidinone antibiotics
Xu L., Zhang L., Jones R., Bryant C., Boddeker N., Mabery E., Bahador G., Watson J., Clough J., Arimilli M., Gillette W., Colagiovanni D., Wang K., Gibbs C., Kim C.U., et. al.
Bioorganic and Medicinal Chemistry Letters , 2011
44.
rcr_88_3_248_bib44
Sokolov
1998
45.
First enantioselective synthesis of the novel antiinfective TAN-1057A via its aminomethyl-substituted dihydropyrimidinone heterocycle
Belov V.N., Brands M., Raddatz S., Krüger J., Nikolskaya S., Sokolov V., de Meijere A.
Tetrahedron , 2004
48.
A new and convergent synthesis for 2,5-diamino-tetrahydropyrimidones
Xu L., Zhang L., Bryant C.M., Kim C.U.
Tetrahedron Letters , 2003
49.
rcr_88_3_248_bib49
Yuan
J. Am. Chem. Soc. , 1997
50.
Efforts toward broadening the spectrum of arylomycin antibiotic activity.
Liu J., Smith P.A., Steed D.B., Romesberg F.
Bioorganic and Medicinal Chemistry Letters , 2013
51.
Differential Cardiorespiratory Effects of Endomorphin 1, Endomorphin 2, DAMGO, and Morphine
CZAPLA M., GOZAL D., ALEA O., BECKERMAN R., ZADINA J.
American Journal of Respiratory and Critical Care Medicine , 2000
52.
Endomorphin-1 Analogues Containing β-Proline Are μ-Opioid Receptor Agonists and Display Enhanced Enzymatic Hydrolysis Resistance
Cardillo G., Gentilucci L., Qasem A.R., Sgarzi F., Spampinato S.
Journal of Medicinal Chemistry , 2002
53.
TAPP analogs containing β3-homo-amino acids: synthesis and receptor binding
Podwysocka D., Kosson P., Lipkowski A.W., Olma A.
Journal of Peptide Science , 2012
56.
48000-fold Acceleration of Hybridization by Chemically Modified Oligonucleotides
Corey D.R.
Journal of the American Chemical Society , 1995
58.
Design of novel inhibitors of aminopeptidases. Synthesis of peptide-derived diamino thiols and sulfur replacement analogs of bestatin
Gordon E.M., Godfrey J.D., Delaney N.G., Asaad M.M., Von Langen D., Cushman D.W.
Journal of Medicinal Chemistry , 1988
59.
Metallopeptidase Inhibitors of Tetanus Toxin:  A Combinatorial Approach
Martin L., Cornille F., Turcaud S., Meudal H., Roques B.P., Fournié-Zaluski M.
Journal of Medicinal Chemistry , 1999
62.
rcr_88_3_248_bib62
May
2002
65.
A facile conversion of arginine into β-homoarginine dipeptides
Bastiaans H.M., Alewijnse A.E., van der Baan J.L., Ottenheijm H.C.
Tetrahedron Letters , 1994
67.
rcr_88_3_248_bib67
Matthews
1998
69.
Conformationally Homogeneous Cyclic Tetrapeptides:  Useful New Three-Dimensional Scaffolds
Glenn M.P., Kelso M.J., Tyndall J.D., Fairlie D.P.
Journal of the American Chemical Society , 2002
71.
rcr_88_3_248_bib71
Mattews
1997
72.
Small Multivalent Architectures Mimicking Homotrimers of the TNF Superfamily Member CD40L:  Delineating the Relationship between Structure and Effector Function
Trouche N., Wieckowski S., Sun W., Chaloin O., Hoebeke J., Fournel S., Guichard G.
Journal of the American Chemical Society , 2007
76.
Peptide Folding Induces High and Selective Affinity of a Linear and Small β-Peptide to the Human Somatostatin Receptor 4
Gademann K., Kimmerlin T., Hoyer D., Seebach D.
Journal of Medicinal Chemistry , 2001
78.
Antimicrobial Peptides from Marine Proteobacteria
Desriac F., Jégou C., Balnois E., Brillet B., Chevalier P., Fleury Y.
Marine Drugs , 2013
79.
Jasplakinolide, a cyclodepsipeptide from the marine sponge, Jaspis SP.
Crews P., Manes L.V., Boehler M.
Tetrahedron Letters , 1986
80.
Stereostructures of geodiamolides A and B, novel cyclodepsipeptides from the marine sponge Geodia sp
Chan W.R., Tinto W.F., Manchand P.S., Todaro L.J.
Journal of Organic Chemistry , 1987
82.
rcr_88_3_248_bib82
Becker
2015
84.
Nonracemizable Isocyanoacetates for Multicomponent Reactions
Zhdanko A.G., Nenajdenko V.G.
Journal of Organic Chemistry , 2008
85.
Isocyanoacetate Derivatives: Synthesis, Reactivity, and Application
Gulevich A.V., Zhdanko A.G., Orru R.V., Nenajdenko V.G.
Chemical Reviews , 2010
86.
rcr_88_3_248_bib86
Zarezin
2018
87.
Total Synthesis and Biological Evaluation of Grassypeptolide A
Liu H., Liu Y., Wang Z., Xing X., Maguire A.R., Luesch H., Zhang H., Xu Z., Ye T.
Chemistry - A European Journal , 2013
88.
Stereocontrolled Synthesis of Onchidins
Peng Y., Pang H.W., Ye T.
Organic Letters , 2004
89.
Nicotinyl aspartyl ketones as inhibitors of caspase-3
Isabel E., Black W.C., Bayly C.I., Grimm E.L., Janes M.K., McKay D.J., Nicholson D.W., Rasper D.M., Renaud J., Roy S., Tam J., Thornberry N.A., Vaillancourt J.P., Xanthoudakis S., Zamboni R., et. al.
Bioorganic and Medicinal Chemistry Letters , 2003
90.
Novel pyrazinone mono-amides as potent and reversible caspase-3 inhibitors
Han Y., Giroux A., Colucci J., Bayly C.I., Mckay D.J., Roy S., Xanthoudakis S., Vaillancourt J., Rasper D.M., Tam J., Tawa P., Nicholson D.W., Zamboni R.J.
Bioorganic and Medicinal Chemistry Letters , 2005
91.
Structure–activity relationships within a series of caspase inhibitors. Part 2: Heterocyclic warheads
Ullman B.R., Aja T., Chen N., Diaz J., Gu X., Herrmann J., Kalish V.J., Karanewsky D.S., Kodandapani L., Krebs J.J., Linton S.D., Meduna S.P., Nalley K., Robinson E.D., Roggo S.P., et. al.
Bioorganic and Medicinal Chemistry Letters , 2005
92.
Lipophilic versus hydrogen-bonding effect in P3 on potency and selectivity of valine aspartyl ketones as caspase 3 inhibitors
Mellon C., Aspiotis R., Black C.W., Bayly C.I., Grimm E.L., Giroux A., Han Y., Isabel E., McKay D.J., Nicholson D.W., Rasper D.M., Roy S., Tam J., Thornberry N.A., Vaillancourt J.P., et. al.
Bioorganic and Medicinal Chemistry Letters , 2005
93.
Activity-Based Probes for Detection of Active MALT1 Paracaspase in Immune Cells and Lymphomas
Eitelhuber A., Vosyka O., Nagel D., Bognar M., Lenze D., Lammens K., Schlauderer F., Hlahla D., Hopfner K., Lenz G., Hummel M., Verhelst S.L., Krappmann D.
Chemistry & Biology , 2015
94.
Oxamyl dipeptide caspase inhibitors developed for the treatment of stroke
Linton S.D., Aja T., Allegrini P.R., Deckwerth T.L., Diaz J., Hengerer B., Herrmann J., Jahangiri K.G., Kallen J., Karanewsky D.S., Meduna S.P., Nalley K., Robinson E.D., Roggo S., Rovelli G., et. al.
Bioorganic and Medicinal Chemistry Letters , 2004
95.
Modulation of the inhibitor properties of dipeptidyl (acyloxy)methyl ketones toward the CaaX proteases
Dechert A.R., MacNamara J.P., Breevoort S.R., Hildebrandt E.R., Hembree N.W., Rea A.C., McLain D.E., Porter S.B., Schmidt W.K., Dore T.M.
Bioorganic and Medicinal Chemistry , 2010
96.
The design and synthesis of inhibitors of the cysteinyl protease, Der p I
Billson J., Clark J., Conway S.P., Hart T., Johnson T., Langston S.P., Ramjee M., Quibell M., Scott R.K.
Bioorganic and Medicinal Chemistry Letters , 1998
97.
Design, Synthesis, and Evaluation of Inhibitors for Severe Acute Respiratory Syndrome 3C-Like Protease Based on Phthalhydrazide Ketones or Heteroaromatic Esters
Zhang J., Pettersson H.I., Huitema C., Niu C., Yin J., James M.N., Eltis L.D., Vederas J.C.
Journal of Medicinal Chemistry , 2007
99.
New Acyloxymethyl Ketones: Useful Probes for Cysteine Protease Profiling
Matache M., Coman A., Paraschivescu C., Hadade N., Juncu A., Vlaicu O., Popescu C.
Synthesis , 2016
100.
PYRIDONE-BASED PEPTIDOMIMETIC INHIBITORS OF INTERLEUKIN-1β-CONVERTING ENZYME (ICE)
Semple G., Ashworth D.M., Baker G.R., Batt A.R., Baxter A.J., Benzies D.W., Elliot L.H., Evans D.M., Franklin R.J., Hudson P., Jenkins P.D., Pitt G.R., Rooker D.P., Sheppard A., Szelke M., et. al.
Bioorganic and Medicinal Chemistry Letters , 1997
102.
Selectivity profiling of DegP substrates and inhibitors
Hauske P., Meltzer M., Ottmann C., Krojer T., Clausen T., Ehrmann M., Kaiser M.
Bioorganic and Medicinal Chemistry , 2009
104.
Peptidyl carbamates incorporating amino acid isosteres as novel elastase inhibitors
Digenis G.A., Agha B.J., Tsuji K., Kato M., Shinogi M.
Journal of Medicinal Chemistry , 1986
106.
Cytotoxic Simplified Tubulysin Analogues
Raghavan B., Balasubramanian R., Steele J.C., Sackett D.L., Fecik R.A.
Journal of Medicinal Chemistry , 2008
107.
Regioselective structural and functional mimicry of peptides. Design of hydrolytically-stable cyclic peptidomimetic inhibitors of HIV-1 protease.
Abbenante G., March D.R., Bergman D.A., Hunt P.A., Garnham B., Dancer R.J., Martin J.L., Fairlie D.P.
Journal of the American Chemical Society , 1995
108.
Synthesis and activity of HIV protease inhibitors
Garrouste P., Pawlowski M., Tonnaire T., Sicsic S., Dumy P., de Rosny E., Reboud-Ravaux M., Fulcrand P., Martinez J.
European Journal of Medicinal Chemistry , 1998
109.
Use of Papain as a Model for the Structure-Based Design of Cathepsin K Inhibitors:  Crystal Structures of Two Papain−Inhibitor Complexes Demonstrate Binding to S‘-Subsites
LaLonde J.M., Zhao B., Smith W.W., Janson C.A., DesJarlais R.L., Tomaszek T.A., Carr T.J., Thompson S.K., Oh H., Yamashita D.S., Veber D.F., Abdel-Meguid S.S.
Journal of Medicinal Chemistry , 1998
110.
Design and Synthesis of Sulfur Based Inhibitors of Matrix Metalloproteinase-1.
Fujisawa T., Odake S., Ogawa Y., Yasuda J., Morita Y., Morikawa T.
Chemical and Pharmaceutical Bulletin , 2002
111.
Synthesis, biological evaluation, hydration site thermodynamics, and chemical reactivity analysis of α-keto substituted peptidomimetics for the inhibition of Plasmodium falciparum
Weldon D.J., Shah F., Chittiboyina A.G., Sheri A., Chada R.R., Gut J., Rosenthal P.J., Shivakumar D., Sherman W., Desai P., Jung J., Avery M.A.
Bioorganic and Medicinal Chemistry Letters , 2014
112.
rcr_88_3_248_bib112
Tarnowska
Eur. Biophys. J. , 1992
115.
Renin inhibitors containing isosteric replacements of the amide bond connecting the P3 and P2 sites
Kaltenbronn J.S., Hudspeth J.P., Lunney E.A., Michniewicz B.M., Nicolaides E.D., Repine J.T., Roark W.H., Stier M.A., Tinney F.J.
Journal of Medicinal Chemistry , 1990
116.
Stabilized Analogs of Thymopentin. 2. 1,2- and 3,4-Ketomethylene Pseudopeptides
DeGraw J.I., Almquist R.G., Hiebert C.K., Judd A.K., Dousman L., Smith R.L., Waud W.R., Uchida I.
Journal of Medicinal Chemistry , 1997
117.
Substrate analog renin inhibitors containing replacements of histidine in P2 or isosteres of the amide bond between P3 and P2 sites
Raddatz P., Jonczyk A., Minck K.O., Schmitges C.J., Sombroek J.
Journal of Medicinal Chemistry , 1991
118.
Development of the First Potential Covalent Inhibitors of Anandamide Cellular Uptake
Schiano Moriello A., Balas L., Ligresti A., Cascio M.G., Durand T., Morera E., Ortar G., Di Marzo V.
Journal of Medicinal Chemistry , 2006
119.
Exploring the Sn Binding Pockets in Gingipains by Newly Developed Inhibitors:  Structure-Based Design, Chemistry, and Activity
Białas A., Grembecka J., Krowarsch D., Otlewski J., Potempa J., Mucha A.
Journal of Medicinal Chemistry , 2006
120.
Synthesis of EF24−Tripeptide Chloromethyl Ketone:  A Novel Curcumin-Related Anticancer Drug Delivery System
Sun A., Shoji M., Lu Y.J., Liotta D.C., Snyder J.P.
Journal of Medicinal Chemistry , 2006
122.
α-Aminoketone – Ein Beitrag zur Synthese optisch aktiver Derivate von Aminosäuren und Peptiden
Fittkau S., Jahreis G., Peters K., Baláspiri L.
Journal für praktische Chemie , 1986
123.
Synthesis of ketomethylene amino pseudopeptide analogues via reductive amination of glyoxals derived from α-amino acids
Groarke M., Hartzoulakis B., McKervey M.A., Walker B., Williams C.H.
Bioorganic and Medicinal Chemistry Letters , 2000
125.
Inhibitors of the chymotrypsin-like activity of proteasome based on di- and tri-peptidyl α-keto aldehydes (glyoxals)
Lynas J.F., Harriott P., Healy A., McKervey M.A., Walker B.
Bioorganic and Medicinal Chemistry Letters , 1998
127.
Peptidyl β-homo-aspartals: Specific inhibitors of interleukin-1β converting enzyme and its homologues (caspases)
Bajusz S., Fauszt I., Németh K., Barabás É., Juhász A., Patthy M.
Bioorganic and Medicinal Chemistry Letters , 1998
128.
Tripeptidyl pyridinium methyl ketones as potent active site inhibitors of thrombin
Steinmetzer T., Konishi Y.
Bioorganic and Medicinal Chemistry Letters , 1996
130.
4-Phenylbutanoyl-2( S )-acylpyrrolidines and 4-phenylbutanoyl- l -prolyl-2( S )-acylpyrrolidines as prolyl oligopeptidase inhibitors
Wallén E.A., Christiaans J.A., Saario S.M., Forsberg M.M., Venäläinen J.I., Paso H.M., Männistö P.T., Gynther J.
Bioorganic and Medicinal Chemistry , 2002
131.
rcr_88_3_248_bib131
McKervey
1993
133.
(2R)-4-Oxo-4-[3-(Trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin- 7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine:  A Potent, Orally Active Dipeptidyl Peptidase IV Inhibitor for the Treatment of Type 2 Diabetes
Kim D., Wang L., Beconi M., Eiermann G.J., Fisher M.H., He H., Hickey G.J., Kowalchick J.E., Leiting B., Lyons K., Marsilio F., McCann M.E., Patel R.A., Petrov A., Scapin G., et. al.
Journal of Medicinal Chemistry , 2004
134.
Antiplasmodial activity of new 4-aminoquinoline derivatives against chloroquine resistant strain
Sinha M., Dola V.R., Agarwal P., Srivastava K., Haq W., Puri S.K., Katti S.B.
Bioorganic and Medicinal Chemistry , 2014
135.
Cysteine proteinase inhibitors decrease articular cartilage and bone destruction in chronic inflammatory arthritis.
Esser R.E., Angelo R.A., Murphey M.D., Watts L.M., Thornburg L.P., Palmer J.T., Talhouk J.W., Smith R.E.
Arthritis & Rheumatism , 1994
136.
A general solid phase method for the synthesis of sequence independent peptidyl-fluoromethyl ketones
Roiban G., Matache M., Hădade N.D., Funeriu D.P.
Organic and Biomolecular Chemistry , 2012
137.
First-in-Class Pan Caspase Inhibitor Developed for the Treatment of Liver Disease
Linton S.D., Aja T., Armstrong R.A., Bai X., Chen L., Chen N., Ching B., Contreras P., Diaz J., Fisher C.D., Fritz L.C., Gladstone P., Groessl T., Gu X., Herrmann J., et. al.
Journal of Medicinal Chemistry , 2005
138.
In vitro and ex vivo inhibition of hepatitis A virus 3C proteinase by a peptidyl monofluoromethyl ketone.
Morris T.S., Frormann S., Shechosky S., Lowe C., Lall M.S., Gauss-Müller V., Purcell R.H., Emerson S.U., Vederas J.C., Malcolm B.A.
Bioorganic and Medicinal Chemistry , 1997
141.
Design and Preparation of a Potent Series of Hydroxyethylamine Containing β-Secretase Inhibitors That Demonstrate Robust Reduction of Central β-Amyloid
Weiss M.M., Williamson T., Babu-Khan S., Bartberger M.D., Brown J., Chen K., Cheng Y., Citron M., Croghan M.D., Dineen T.A., Esmay J., Graceffa R.F., Harried S.S., Hickman D., Hitchcock S.A., et. al.
Journal of Medicinal Chemistry , 2012
142.
P1 Aspartate-Based Peptide .alpha.-((2,6-Dichlorobenzoyl)oxy)methyl Ketones as Potent Time-Dependent Inhibitors of Interleukin-1.beta.-Converting Enzyme
Dolle R.E., Hoyer D., Prasad C.V., Schmidt S.J., Helaszek C.T., Miller R.E., Ator M.A.
Journal of Medicinal Chemistry , 1994
144.
Synthesis of N-protected erythro-phenylalanylepoxides
Heinsoo A., Raidaru G., Linask K., Järv J., Zetterström M., Langel Ü.
Tetrahedron Asymmetry , 1995
145.
Countering Cooperative Effects in Protease Inhibitors Using Constrained β-Strand-Mimicking Templates in Focused Combinatorial Libraries
Reid R.C., Pattenden L.K., Tyndall J.D., Martin J.L., Walsh T., Fairlie D.P.
Journal of Medicinal Chemistry , 2004
146.
β-Strand Mimicking Macrocyclic Amino Acids:  Templates for Protease Inhibitors with Antiviral Activity
Glenn M.P., Pattenden L.K., Reid R.C., Tyssen D.P., Tyndall J.D., Birch C.J., Fairlie D.P.
Journal of Medicinal Chemistry , 2001
147.
New hydroxyethylamine HIV protease inhibitors that suppress viral replication
Rich D.H., Prasad J.V., Sun C.Q., Green J., Mueller R., Houseman K., MacKenzie D., Malkovsky M.
Journal of Medicinal Chemistry , 1992
149.
Aminodiol HIV Protease Inhibitors. Synthesis And Structure−Activity Relationships Of P1/P1‘ Compounds:  Correlation between Lipophilicity and Cytotoxicity
Chen P., Cheng P.T., Alam M., Beyer B.D., Bisacchi G.S., Dejneka T., Evans A.J., Greytok J.A., Hermsmeier M.A., Humphreys W.G., Jacobs G.A., Kocy O., Lin P., Lis K.A., Marella M.A., et. al.
Journal of Medicinal Chemistry , 1996
150.
Viracept (Nelfinavir Mesylate, AG1343):  A Potent, Orally Bioavailable Inhibitor of HIV-1 Protease
Kaldor S.W., Kalish V.J., Davies J.F., Shetty B.V., Fritz J.E., Appelt K., Burgess J.A., Campanale K.M., Chirgadze N.Y., Clawson D.K., Dressman B.A., Hatch S.D., Khalil D.A., Kosa M.B., Lubbehusen P.P., et. al.
Journal of Medicinal Chemistry , 1997
151.
Amino Diol HIV Protease Inhibitors. 1. Design, Synthesis, and Preliminary SAR
Barrish J.C., Gordon E., Alam M., Lin P., Bisacchi G.S., Chen P., Cheng P.T., Fritz A.W., Greytok J.A.
Journal of Medicinal Chemistry , 1994
152.
rcr_88_3_248_bib152
Gante
1989
153.
Azetidinones as vasopressin V1a antagonists
Guillon C.D., Koppel G.A., Brownstein M.J., Chaney M.O., Ferris C.F., Lu S., Fabio K.M., Miller M.J., Heindel N.D., Hunden D.C., Cooper R.D., Kaldor S.W., Skelton J.J., Dressman B.A., Clay M.P., et. al.
Bioorganic and Medicinal Chemistry , 2007
154.
β-Lactam Cholesterol Absorption Inhibitors
Burnett D.
Current Medicinal Chemistry , 2004
158.
rcr_88_3_248_bib158
Linder
2001
160.
rcr_88_3_248_bib160
Podlech
1999
161.
rcr_88_3_248_bib161
Maier
2002
162.
rcr_88_3_248_bib162
Maier
2004
164.
10.1021/ol015891+
165.
The development of hydrazide γ-turn mimetics
Ferguson M.D., Meara J.P., Nakanishi H., Lee M.S., Kahn M.
Tetrahedron Letters , 1997
166.
Synthesis and antiviral activity of monobactams inhibiting the human cytomegalovirus protease.
Ogilvie W.W., Yoakim C., Dô F., Haché B., Lagacé L., Naud J., O'Meara J.A., Déziel R.
Bioorganic and Medicinal Chemistry , 1999
167.
β-Lactam Derivatives as Inhibitors of Human Cytomegalovirus Protease
Yoakim C., Ogilvie W.W., Cameron D.R., Chabot C., Guse I., Haché B., Naud J., O'Meara J.A., Plante R., Déziel R.
Journal of Medicinal Chemistry , 1998
169.
rcr_88_3_248_bib169
Burtoloso
2005
172.
Stereocontrolled synthesis of 5-azaspiro[2.3]hexane derivatives as conformationally “frozen” analogues of L-glutamic acid
Bechi B., Amantini D., Tintori C., Botta M., Fabio R.D.
Beilstein Journal of Organic Chemistry , 2014
173.
Synthesis and Evaluation of Keto-Glutamine Analogues as Inhibitors of Hepatitis A Virus 3C Proteinase
Ramtohul Y.K., James M.N., Vederas J.C.
Journal of Organic Chemistry , 2001
174.
rcr_88_3_248_bib174
Wang
1999
176.
Total synthesis of polyoximic acid
Hanessian S., Fu J.
Canadian Journal of Chemistry , 2001
177.
Total synthesis of (+)-polyoximic acid - cis-3-ethylidene-L-azetidine-2-carboxylic acid
Hanessian S., Fu J., Chiara J., Fabio R.D.
Tetrahedron Letters , 1993
179.
Facile Synthesis of Optically Active Imidazole Derivatives
Marek A., Kulhanek J., Ludwig M., Bures F.
Molecules , 2007
181.
Synthesis of amino acid-derived imidazoles from enantiopure N-protected α-amino glyoxals
Groarke M., McKervey M.A., Nieuwenhuyzen M.
Tetrahedron Letters , 2000
182.
rcr_88_3_248_bib182
Darkins
1993
183.
SAR exploration at the C-3 position of tetrahydro-β-carboline sstr3 antagonists
He S., Dobbelaar P.H., Guo L., Ye Z., Liu J., Jian T., Truong Q., Shah S.K., Du W., Qi H., Bakshi R.K., Hong Q., Dellureficio J.D., Sherer E., Pasternak A., et. al.
Bioorganic and Medicinal Chemistry Letters , 2016
184.
Thiazole and oxazole peptides: biosynthesis and molecular machinery
Roy R.S., Gehring A.M., Milne J.C., Belshaw P.J., Walsh C.T., Roy R.S., Gehring A.M., Milne J.C., Belshaw P.J., Walsh C.T.
Natural Product Reports , 1999
185.
Synthesis of amino acid-derived thiazoles from enantiopure N-protected α-amino glyoxals
Groarke M., McKervey M.A., Moncrieff H., Nieuwenhuyzen M.
Tetrahedron Letters , 2000
186.
Non-Nucleoside Benzimidazole-Based Allosteric Inhibitors of the Hepatitis C Virus NS5B Polymerase:  Inhibition of Subgenomic Hepatitis C Virus RNA Replicons in Huh-7 Cells
Beaulieu P.L., Bousquet Y., Gauthier J., Gillard J., Marquis M., McKercher G., Pellerin C., Valois S., Kukolj G.
Journal of Medicinal Chemistry , 2004
187.
Synthesis and anti-Candida activity of novel 2-hydrazino-1,3-thiazole derivatives
Maillard L.T., Bertout S., Quinonéro O., Akalin G., Turan-Zitouni G., Fulcrand P., Demirci F., Martinez J., Masurier N.
Bioorganic and Medicinal Chemistry Letters , 2013
188.
Synthesis and evaluation of lysine derived sulfamides as histone deacetylase inhibitors
Manku S., Allan M., Nguyen N., Ajamian A., Rodrigue J., Therrien E., Wang J., Guo T., Rahil J., Petschner A.J., Nicolescu A., Lefebvre S., Li Z., Fournel M., Besterman J.M., et. al.
Bioorganic and Medicinal Chemistry Letters , 2009
189.
Pyrimidinone antibiotics—heterocyclic analogues with improved antibacterial spectrum
Brands M., Grande Y.C., Endermann R., Gahlmann R., Krüger J., Raddatz S.
Bioorganic and Medicinal Chemistry Letters , 2003
190.
Conformationally restricted analogs of deoxynegamycin
Raju B., Anandan S., Gu S., Herradura P., O’Dowd H., Kim B., Gomez M., Hackbarth C., Wu C., Wang W., Yuan Z., White R., Trias J., Patel D.V.
Bioorganic and Medicinal Chemistry Letters , 2004
192.
rcr_88_3_248_bib192
Boynton
2000
193.
1,3-Dipole cascade. A new method for azomethine ylide formation
Padwa A., Dean D.C., Zhi L.
Journal of the American Chemical Society , 1989
195.
Trifluoroacetic acid-mediated intramolecular formal N-H insertion reactions with amino-α-diazoketones: a facile and efficient synthesis of optically pure pyrrolidinones and piperidinones
Yang H., Jurkauskas V., Mackintosh N., Mogren T., Stephenson C.R., Foster K., Brown W., Roberts E.
Canadian Journal of Chemistry , 2000
196.
Synthesis and evaluation of cis-hexahydropyrrolo[3,2-b]pyrrol-3-one peptidomimetic inhibitors of CAC1 cysteinyl proteinases
Quibell M., Benn A., Flinn N., Monk T., Ramjee M., Ray P., Wang Y., Watts J.
Bioorganic and Medicinal Chemistry , 2005
197.
rcr_88_3_248_bib197
Fetter
1986
199.
rcr_88_3_248_bib199
Gharpure
2017
201.
rcr_88_3_248_bib201
Lalithamba
2010
204.
rcr_88_3_248_bib204
Dufour
1986
205.
5-(2-Pyrrolidinyl)oxazolidinones and 2-(2-pyrrolidinyl)benzodioxanes: Synthesis of all the stereoisomers and α4β2 nicotinic affinity
Pallavicini M., Bolchi C., Binda M., Cilia A., Clementi F., Ferrara R., Fumagalli L., Gotti C., Moretti M., Pedretti A., Vistoli G., Valoti E.
Bioorganic and Medicinal Chemistry Letters , 2009
206.
Short, enantiogenic syntheses of (-)-indolizidine 167B and (+)-monomorine
Jefford C.W., Tang Q., Zaslona A.
Journal of the American Chemical Society , 1991
207.
Sedum alkaloids II: sedacryptine, a new minor base from sedum acre.
Hootelé C., Colau B., Halin F., Declercq J.P., Germain G., Van Meerssche M.
Tetrahedron Letters , 1980
210.
rcr_88_3_248_bib210
Clark
2001
211.
rcr_88_3_248_bib211
Clark
2001
213.
Synthesis of Optically Active β-Amino Acid N-Carboxyanhydrides
Cheng J., Ziller J.W., Deming T.J.
Organic Letters , 2000
214.
rcr_88_3_248_bib214
Kricheldorf
1987
215.
rcr_88_3_248_bib215
Darkins
2000
216.
Amino acids and peptides. LVI. Synthesis of pyrazinone ring-containing opioid mimetics and examination of their opioid receptor binding activity
Okada Y., Fukumizu A., Takahashi M., Yamazaki J., Yokoi T., Tsuda Y., Bryant S.D., Lazarus L.H.
Tetrahedron , 1999
217.
Potent Dmt-Tic Pharmacophoric δ- and μ-Opioid Receptor Antagonists
Li T., Fujita Y., Shiotani K., Miyazaki A., Tsuda Y., Ambo A., Sasaki Y., Jinsmaa Y., Marczak E., Bryant S.D., Salvadori S., Lazarus L.H., Okada Y.
Journal of Medicinal Chemistry , 2005
218.
rcr_88_3_248_bib218
Ishida
J. Am. Chem. Soc. , 2013
220.
rcr_88_3_248_bib220
Harrison
1999
221.
Sedative but not anxiolytic properties of benzodiazepines are mediated by the GABAA receptor α1 subtype
McKernan R.M., Rosahl T.W., Reynolds D.S., Sur C., Wafford K.A., Atack J.R., Farrar S., Myers J., Cook G., Ferris P., Garrett L., Bristow L., Marshall G., Macaulay A., Brown N., et. al.
Nature Neuroscience , 2000
224.
Exploring the Chemistry of Epoxy Amides for the Synthesis of the 2′′-epi-Diazepanone Core of Liposidomycins and Caprazamycins
Sarabia F., Vivar-García C., García-Ruiz C., Martín-Ortiz L., Romero-Carrasco A.
Journal of Organic Chemistry , 2012
225.
Modern Trends of Organic Chemistry in Russian Universities
Konovalov A.I., Antipin I.S., Burilov V.A., Madzhidov T.I., Kurbangalieva A.R., Nemtarev A.V., Solovieva S.E., Stoikov I.I., Mamedov V.A., Zakharova L.Y., Gavrilova E.L., Sinyashin O.G., Balova I.A., Vasilyev A.V., Zenkevich I.G., et. al.
Russian Journal of Organic Chemistry , 2018
226.
Development of new methods in modern selective organic synthesis: Preparation of functionalized molecules with atomic precision
Ananikov V.P., Khemchyan L.L., Ivanova Y.V., Bukhtiyarov V.I., Sorokin A.M., Prosvirin I.P., Vatsadze S.Z., Medved'ko A.V., Nuriev V.N., Dilman A.D., Levin V.V., Koptyug I.V., Kovtunov K.V., Zhivonitko V.V., Likholobov V.A., et. al.
Russian Chemical Reviews , 2014