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UC on ChemSpider
Alicia's Masters Thesis
Open Web Drug Dev.
To Do List
Ugi NMR Analysis
Reviews of the Anti-malarial agents
Buchholz, Mailu, Boniface (2007; 3; 225-255) Frontiers in drug design and discovery (Book Series); Structure-Based Drug Development Against Malaria (
Doron Greenbaum (2002) A Funtional Proteomics Approach To Understand The Role Of Cysteine Proteases (Dissertation); Diss. Abstr. Int., B 2002, 63(4), 1699 (
Ramjee, Flynn, et.al
; Substrate mapping and inhibitor profiling of falcipain-2, falcipain-3 and berghepain-2: implications for peptidase anti-malarial drug discovery; Biochem. J. (2006) 399, 47–57.
Drahl, Carmen et. al.
Protein Reactive Natural Products Angew. Chem. Int. Ed. (2005) 44, 5788. - a review of suicide inhibitors, including E-64.
Chansuda W, Amy L P, et. al
Epidemiology of drug-resistant malaria; The Lancets Infectious Diseases; 2,(4), 2002, p 209-218
Reviews of the Ugi reaction
Great starting point with many reviews listed
Domling and Ugi (2000) Multicomponent Reactions with Isocyanides
Mechanism of Ugi reaction
Marcaccini & Torroba; Nature Protocols (2007)
Demartino presentation (2003)
Bu & Kjoniksen 2004 Biomacromolecules
General scheme where isocyanide is added before acid.
Bu & Kjoniksen 2005 European Polymer Journal
General scheme where isocyanide is added before acid.
A Plausible Mechanism- Ugi Reaction
Keating and Armstrong 1996
although tetrahedral intermediate is not shown in their mechanism).
General Ugi reaction mechanism
Use of the Ugi reaction in Virtual Libraries
Rarey & Lengauer 2007 Book
The Hydrophobic Effect 2. Relative Importance of the Hydrophobic Effect on the Solubility of Hydrophobes and Pharmaceuticals in H-bonded solvents. Journal of Pharmaceutical Sciences. 1998 (87), Iss. 8, pgs. 998-1014
Quantitative Solubility-Structure Relationships for some meta- and para- substitutued Benzoic Acids in p-doixane and in Tetrahydrofuran.
Acid-catalyzed Ring opening/polymerization of furans
hydrolysis is one example - find refs
Macromolecular Chemistry and Physics, Polymerization of furfuryl alcohol with TFA
Malaria Inhibition Assays
PfENR UV assay (Perozzo 2002)>
2003 JBC Kuo
Targeting Tuberculosis and Malaria through inhibition of enoyl reductase.
Reviews on the synthesis of diketopiperazines
2006 Chem. Rev. Doemling
see p. 32 Ref 103 looks interesting
2003 Hulme Methods in Enzymology
1996 Ellman Chem.
Rev. Solid Support DKP synthesis (see p. 571)
J. Zhu, H. Beinayme (Wiley)
Examples of the synthesis of diketopiperazines with required
1998 Hulme Tet. Lett.
Uses cyclohexenyl isocyanide and benzyl isocycanide but limited experimental data.
1995 Steele Solid Support strategy
- does not use Ugi reaction
Relevant but not perfect for our Ugi reaction/cyclization
Sollis 2005 J. Org. Chem.
This one has the right substitution pattern and has lots of good info on cyclizing and characterizing DKPs but has an extra amide group
2004 Thomas Godet
Titanium Catalysis in the Ugi Reaction of
-Amino Acids with Aromatic Aldehydes - aromatic aldehydes are sluggish and can be accelerated with TiCl4
Marcaccini 2001 Tetrahedron Letters
(chloroacetic acid route) Wrong substitution pattern but an example of the synthesis of DKPs using UDC.
1996 Armstrong J. Am. Chem. Soc.
Full description of the use of cyclohexenyl isocyanide as a convertible isonitrile.
Hiromu Habashita et al. 2006 J Med. Chem
A spirodiketopiperazine synthesis using an isonitrile resin through the Ugi reaction, sequential transformation and cyclative cleavage.
Harriman 1997 Tet. Lett.
Use of the morpholinoethyl isocyanide in an intramolecular Ugi reaction with good yields in methanol 48 hours.
Bothwick 2005 J. Med. Chem.
Contains NMR data of products, describes use of t-butyl and isopropyl isocyanides in a Ugi synthesis with slightly different reagents.
Zhu,D; Chem, R; et.al
; An Efficient Procedure for the synthesis of Morpholino-2-one-3-carboxamide Derivatives in Good Diastereoselectivity by the Ugi Reaction (
Buchanan and Dawson, Organic Magnetic Resonance
, Vol 13 Iss 4 293-298 1980- NMR characterization of certain Imines.(
Li, Rerr Yu; Bei, Feng Li, Wang, Xin; et.al. (
Chinese Journal of Organic Chemistry
, Vol. 23 No. 9, 984-987) The article deals with the solid-phase reaction of furfurylamine and vanillin at room temperature. The product is characterized by proton NMR and other techniques including crystal structure analysis. (
2003 Moonkwon Lee; Jaebum Choo
Gives a rate of a similar imine monitored by Raman spectroscopy which is very close to the rates we have been getting - about
in CDCl3 for acetophenone and aniline derivatives
Jack Hine, Michael S. Cholod, and Walter K. Chess
: (Journal of American Chemical Society Vol-95, Iss-13 pp 4270 - 4276) Kinetics of the formation of imines from acetone and primary amines. Evidence for internal acid-catalyzed dehydration of certain intermediate carbinolamines - about
in water for n-butylamine and acetone
Stephany et al.
A 13C- NMR and IR Study of Isocyanides and Some of Their Complexes
Organic Magnetic Resonance 1974 Vol 6 pp 45-47. (
I. D. Kuntz, Jr., Paul von Ragué Schleyer, and A. Allerhand. J.;
Long- Range N14-H1 Nuclear-Resonance Coupling in Isonitriles
; I. D. J. Chem. Phys. 1961, 35, 1533-1534. (
É. Ya. Lukevits, et.al
Chemistry of Heterocyclic Compounds; Vol. 22, Iss. 6 pp 678-679.
Kosei Ohno and Minoru Machida
Tet.Lett. Vol. 22, Iss. 45 pp 4487-4488; 1981 (
JCAMP-DX for NMR
:DAVIES and LAMPEN Applied Spectroscopy , Vol 47, Iss 8 1093-1099, Aug 1993
Removal of t-butoxycarbonyl protecting groups with trifluoroacetic acid. (Lundt, Johansen, Volund, Markussen)
Int J Pept Protein Res. 1978 Nov;12(5):258-68
General Isonitrile syntheses
Microwave assisted Isonitrile synthesis
J. Org Chem. 2005, 70, 2361-2363
Synthesis of Cyclohexen-1-yl-isocyanide and N-Cylcohex-1-enyl-formamide
Bioorganic & Medicinal Chemistry Volume 8, Issue 6 , June 2000, Pages 1343-1360
Rapid deprotection of
-Boc amines by TFA combined with freebase generation using basic ion-exchange resins :Molecular Diversity,
Volume 9, Number 4 / November, 2005
NMR Chemical Shifts of Common Laboratory Solvents as Trace Impurities
; J. Org. Chem. 1997, 62, 7512-7515
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