refs

Reviews of the Anti-malarial agents

 * 1) Buchholz, Mailu, Boniface (2007; 3; 225-255) Frontiers in drug design and discovery (Book Series); Structure-Based Drug Development Against Malaria ([|Private Access])
 * 2) Doron Greenbaum (2002) A Funtional Proteomics Approach To Understand The Role Of Cysteine Proteases (Dissertation); Diss. Abstr. Int., B 2002, 63(4), 1699 ([|Private Access])
 * 3) [|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.
 * 4) [|Drahl, Carmen et. al.] Protein Reactive Natural Products Angew. Chem. Int. Ed. (2005) 44, 5788. - a review of suicide inhibitors, including E-64.
 * 5) [|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

 * 1) [|Wikipedia] Great starting point with many reviews listed
 * 2) [|Domling and Ugi (2000) Multicomponent Reactions with Isocyanides]

Mechanism of Ugi reaction

 * 1) [|Marcaccini & Torroba; Nature Protocols (2007)] ([|Private Access])
 * 2) [|Demartino presentation (2003)]
 * 3) [|Bu & Kjoniksen 2004 Biomacromolecules] General scheme where isocyanide is added before acid.
 * 4) [|Bu & Kjoniksen 2005 European Polymer Journal] General scheme where isocyanide is added before acid.
 * 5) [|A Plausible Mechanism- Ugi Reaction] (ref: [|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

 * 1) [|Rarey & Lengauer 2007 Book]

Solubilities
1. [|Private Access] 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 2. [|Private Access] 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

 * 1) hydrolysis is one example - find refs
 * 2) [|Gonzalez 1992] Macromolecular Chemistry and Physics, Polymerization of furfuryl alcohol with TFA

Malaria Inhibition Assays

 * 1) [|PfENR UV assay (Perozzo 2002)>]
 * 2) [|2003 JBC Kuo] Targeting Tuberculosis and Malaria through inhibition of enoyl reductase.

Reviews on the synthesis of diketopiperazines

 * 1) [|2006 Chem. Rev. Doemling] see p. 32 Ref 103 looks interesting
 * 2) [|2005 Doemling]
 * 3) [|2003 Hulme Methods in Enzymology]
 * 4) [|1996 Ellman Chem.] Rev. Solid Support DKP synthesis (see p. 571)
 * 5) [|Multicomponent Reaction] J. Zhu, H. Beinayme (Wiley)

Examples of the synthesis of diketopiperazines with required [|substitution pattern]

 * 1) [|1998 Hulme Tet. Lett.] Uses cyclohexenyl isocyanide and benzyl isocycanide but limited experimental data.
 * 2) [|1995 Steele Solid Support strategy] - does not use Ugi reaction

Relevant but not perfect for our Ugi reaction/cyclization

 * 1) [|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
 * 2) [|2004 Thomas Godet] Titanium Catalysis in the Ugi Reaction of [[image:http://pubs.acs.org/images/gifchars/alpha.gif]]-Amino Acids with Aromatic Aldehydes - aromatic aldehydes are sluggish and can be accelerated with TiCl4
 * 3) [|Marcaccini 2001 Tetrahedron Letters] (chloroacetic acid route) Wrong substitution pattern but an example of the synthesis of DKPs using UDC.
 * 4) [|1996 Armstrong J. Am. Chem. Soc.] Full description of the use of cyclohexenyl isocyanide as a convertible isonitrile.
 * 5) [|Hiromu Habashita et al. 2006 J Med. Chem] A spirodiketopiperazine synthesis using an isonitrile resin through the Ugi reaction, sequential transformation and cyclative cleavage.
 * 6) [|Harriman 1997 Tet. Lett.] Use of the morpholinoethyl isocyanide in an intramolecular Ugi reaction with good yields in methanol 48 hours.
 * 7) [|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.
 * 8) [|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 ([|Private Access])

Imine formation

 * 1) Phenylacetaldehyde
 * 2) [|Buchanan and Dawson, Organic Magnetic Resonance], Vol 13 Iss 4 293-298 1980- NMR characterization of certain Imines.([|Private Access])
 * 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. ([|Private Access]).

Imine Rates

 * 1) [|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 **0.01 /M*min** in CDCl3 for acetophenone and aniline derivatives
 * 2) [|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 **0.1 /M*min** in water for n-butylamine and acetone


 * Isocyanides NMR:**
 * 1) 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. ([|Private access])
 * 2) 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. ([|Private Access])


 * Furan Alkylation**
 * 1) [|É. Ya. Lukevits, et.al] Chemistry of Heterocyclic Compounds; Vol. 22, Iss. 6 pp 678-679.
 * 2) [|Kosei Ohno and Minoru Machida] Tet.Lett. Vol. 22, Iss. 45 pp 4487-4488; 1981 ([|Private Access])


 * Miscellaneous**
 * 1) [|JCAMP-DX for NMR] :DAVIES and LAMPEN Applied Spectroscopy, Vol 47, Iss 8 1093-1099, Aug 1993
 * 2) Removal of t-butoxycarbonyl protecting groups with trifluoroacetic acid. (Lundt, Johansen, Volund, Markussen) [|Int J Pept Protein Res. 1978 Nov;12(5):258-68]
 * 3) [|General Isonitrile syntheses] (Private Access)
 * 4) [|Microwave assisted Isonitrile synthesis] J. Org Chem. 2005, 70, 2361-2363
 * 5) [|Synthesis of Cyclohexen-1-yl-isocyanide and N-Cylcohex-1-enyl-formamide] Bioorganic & Medicinal Chemistry Volume 8, Issue 6, June 2000, Pages 1343-1360
 * 6) Rapid deprotection of **//N//**-Boc amines by TFA combined with freebase generation using basic ion-exchange resins :Molecular Diversity, [|Volume 9, Number 4 / November, 2005]
 * 7) [|NMR Chemical Shifts of Common Laboratory Solvents as Trace Impurities] ; J. Org. Chem. 1997, 62, 7512-7515

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