Rapid assembly of molecular diversity via exploitation of isocyanide-based multi-component reactions

Current Opinion in Drug Discovery and Development

Volumn 6, Issue 6, 2003, Pages 921-929

  Hulme, Christopher ^a   Nixey, Thomas ^a  

^a AMGEN INC   (United States)

Author keywords

Isocyanides; Passerini reaction; Ugi reaction

Indexed keywords

ACETAMIDE DERIVATIVE; AGRICULTURAL CHEMICAL; AZEPINE DERIVATIVE; BENZODIAZEPINE DERIVATIVE; BETA LACTAM ANTIBIOTIC; CYANIDE; HETEROCYCLIC COMPOUND; MACROCYCLIC COMPOUND; NATURAL PRODUCT; PROTEINASE INHIBITOR; PYRROLE DERIVATIVE;

AUTOMATION; BIOTRANSFORMATION; CHEMICAL REACTION; CHIRALITY; COMBINATORIAL LIBRARY; CYCLIZATION; CYCLOADDITION; DIELS ALDER REACTION; HIGH THROUGHPUT SCREENING; LIPOPHILICITY; POLYMERIZATION; REACTION ANALYSIS; REVIEW; SOLID STATE; SYNTHESIS; TECHNIQUE; TECHNOLOGY;

COMBINATORIAL CHEMISTRY TECHNIQUES; CYANIDES; HETEROCYCLIC COMPOUNDS; PHARMACEUTICAL PREPARATIONS;

EID: 0347719501     PISSN: 13676733     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (41)

1. Weber L: High diversity combinatorial libraries. Curr Opin Chem Biol (2000) 4(3):295-302. An excellent review describing developments that enable the synthesis of compound libraries exhibiting structural diversities similar to those of natural products.
2. Passerini M: Isonitriles. I. Compound of p-isonitrileazobenzene with acetone and acetic acid. Gazz Chim Ital (1921) 51:126.
3. Ugi I: The α-addition of immonium ions and anions to isonitriles accompanied by secondary reactions. Angew Chem Int Ed (1962) (1):8.
4. Rossen K, Pye PJ, DiMichele LM, Volante RP, Reider PJ: An efficient asymmetric hydrogenation approach to the synthesis of the Crixivan piperazine intermediate. Tetrahedron Lett (1998) 39(38):6823-6826.
5. Schreiber SL: Chemical genetics resulting from a passion for organic chemistry. Bioorg Med Chem (1998) 6(8):1127-1152. The original paper describing the concept of chemical genetics and its applications for finding small and selective inhibitors that enable knockout of protein function and elucidation of their biological role.
6. Moran EJ, Tellew JE, Zhao Z, Armstrong RW: Dehydroamino acid derivatives from D-arabinose and L-serine: Synthesis of models for the azinomycin antitumor antibiotics. J Org Chem (1993) 58(27):7848-7859.
7. Dunn BM (Ed): Structure and Function of the Aspartic Proteases: Genetics, Structures, and Mechanisms. Plenum Press, New York, NY, USA (1991) 306(xviii):585.
8. Jones W, Tadesse S, Chenera B, Viswanadhan V, Hulme C: A facile, three step, one pot synthesis of norstatines using the Passerini reaction. 223rd American Chemical Society Meeting, Orlando, FL, USA (2002).
9. Vassar R, Bennett BD, Babu-Khan S, Kahn S, Mendiaz EA, Denis P, Teplow DB, Ross S, Amarante P, Loeloff R, Luo Y et al. β-Secretase cleavage of Alzheimer's amyloid precursor protein by the transmembrane aspartic protease BACE. Science (1999) 286(5440):735-741.
10. Banfi L, Guanti G, Riva R, Basso A, Calcagno E: Short synthesis of protease inhibitors via modified Passerini condensation of N-Boc-α -aminoaldehydes. Tetrahedron Lett (2002) 43(22):4067-4069.
11. Tsuda M, Muraoka Y, Nagai M, Aoyagi T, Takeuchi T: Poststatin, a new inhibitor of prolyl endopeptidase. VII. N-Cycloalkylamide analogues. J Antibiot (1996) 49(9):909-920.
12. Ogilvie W, Baliey M, Poupart MA, Abraham A, Bhavsar A, Bonneau P Bordeleau J, Bousquet Y, Chabot C, Duceppe JS et al: Peptidomimetic inhibitors of the human cytomegalovirus protease. J Med Chem (1997) 40(25):4113-4135.
13. Yehia AM, Antuch W, Hess S, Schauer-Vukasinovic V, Beck B, Furer P, Almstetter M, Thormann M, Dale G, Oefner C, D'Arcy A et al: HIV protease inhibitors by a novel MCR. 2nd International MultiComponent Reaction Symposium, Genoa, Italy (2003):P56.
14. 3-modified Passerini MCC/N-capping strategy. Tetrahedron Lett (2002) 43(38):6833-6835.
15. Abell AD, Foulds GJ: Synthesis of a cis-conformationally restricted peptide bond isostere and its application to the inhibition of the HIV-1 protease. J Chem Soc Perkin 1 (1997) 17:2475-2482.
16. Denmark SE, Fan Y: The first catalytic, asymmetric α-additions of isocyanides. Lewis-base-catalyzed, enantioselective Passerini-type reactions. J Am Chem Soc (2003) 125(26):7825-7827.
17. Marcaccini S, Pepino R, Torroba T, Miguel D, García-Valverde M: Synthesis of thiomorpholines by an intramolecular Ugi reaction. Tetrahedron Lett (2002) 43(47):8591-8593.
18. Marcaccini S, Miguel D, Torroba T, Garcia-Valverde M: 1,4-Thiazepines, 1,4-benzothiazepin-5-ones, and 1,4-benzothioxepin orthoamides via multicomponent reactions of isocyanides. J Org Chem (2003) 68(8):3315-3318.
19. Ugi I, Wischofer E: The synthesis of simple penicillin derivatives. Chem Ber (1962) (95):136.
20. Gedey S, Van der Eycken J, Fulop F: Liquid-phase combinatorial synthesis of alicyclic β-lactams via Ugi four-component reaction. Org Lett (2002) 4(11):1967-1969.
21. Kolb J, Beck B, Dömling A: Simultaneous assembly of the β-lactam and thiazole moiety by a new multicomponent reaction. Tetrahedron Lett (2002) 43(39):6897-6901.
22. Behnke D, Taube R: A novel three component reaction leading to substituted 2-(cyanomethylamino)-acetamides. 2nd International MultiComponent Reaction Symposium, Genoa, Italy (2003): P6.
23. Kennedy AL, Fryer AM, Josey JA: A new resin-bound universal isonitrile for the Ugi 4CC reaction: Preparation and applications to the synthesis of 2,5-diketopiperazines and 1,4-benzodiazepine-2,5-diones. Org Lett (2002) 4(7):1167-1170.
24. Lindhorst T, Bock H, Ugi I: A new class of convertible isocyanides in the Ugi four-component reaction. Tetrahedron (1999) 55(24):7411-7420.
25. Chen JJ, Golebiowski A, Klopfenstein SR, West L: The universal Rink-isonitrile resin: Applications in Ugi reactions. Tetrahedron Lett (2002) 43(22):4083-4085.
26. Nixey T, Kelly M, Semin D, Hulme C: Short solution phase preparation of fused azepine-tetrazoles via a UDC (Ugi/de-Boc/cyclize) strategy. Tetrahedron Lett (2002) 43(20):3681-3684.
27. Hulme C, Gore V: Multi-component reactions: Emerging chemistry in drug discovery: From Xylocain to Crixivan. Curr Med Chem (2003) 10(1):51-80. A comprehensive review detailing the emerging utility of MCRs throughout the drug discovery process.
28. Paulvannan K: Preparation of tricyclic nitrogen heterocycles via tandem four-component condensation/intramolecular Diels-Alder reaction. Tetrahedron Lett (1999) 40(10):1851-1854.
29. Abell AD, Foulds GJ: Synthesis of a cis-conformationally restricted peptide bond isostere and its application to the inhibition of the HIV-1 protease. J Chem Soc Perkin Trans 1 (1997) (17):2475-2482.
30. Wright DL, Robotham CV, Aboud K: Studies on the sequential multi-component coupling/Diels-Alder cycloaddition reaction. Tetrahedron Lett (2002) 439(6):943-946.
31. Sung K, Wu SH, Chen PI: Facile two-pot syntheses of novel alternating benzene/imidazole systems. Tetrahedron (2002) 58(28):5599-5602.
32. 5-2-oxopiperazines via N-acyliminium ion cyclization. Tetrahedron Lett (2002) 43(36):6293-6295.
33. Beck B, Picard A, Mejat B, Magnin-Lachaux M, Domling A: Towards new chemistry spaces: Union of isocyanide based multicomponent reactions (MCR) with the Horner-Wadsworth-Emmons Reaction (HWE). 2nd International MultiComponent Reaction Symposium, Genoa, Italy (2003):P57.
34. NAr methodology. Part 2: Novel three-step solution phase access to libraries of benzodiazepines. Tetrahedron Lett (2003) 44(9):1947-1950.
35. NAr-based cycloetherification. Tetrahedron Lett (2003) 44(30):5575-5578.
36. 2) synthesis of macrocycles. Angew Chem Int Ed (2003) 42(7):811-814.
37. Beck B, Larbig G, Mejat B, Magnin-Lachaux M, Picard A, Herdtweck E, Dömling A: Short and diverse route toward complex natural product-like macrocycles. Org Lett (2003) 5(7):1047-1050.
38. Fayol A, Zhu J: Synthesis of furoquinolines by a multicomponent domino process. Angew Chem Int Ed (2002) 41(19):3633-3635. An excellent example of the complexity generating power of multi-component reactions approaching the structural complexity observed in natural products.
39. Montaño RG, Zhu J: Rapid access to tetracyclic ring system of lennoxamine type natural product by combined use of a novel three-component reaction and Pummerer cyclization. Chem Commun (2002) (20):2448-2449.
40. McDowell RS, Blackburn BK, Gadek TR, McGee LR, Rawson T, Reynolds ME, Robarge KD, Somers TC, Thorsett ED, Tischler M, Webb RR et al: From peptide to non-peptide. 2. The de novo design of potent, non-peptidal inhibitors of platelet aggregation based on a benzodiazepinedione scaffold. J Am Chem Soc (1994) 116(12):5077-5083.
41. Lack O, Weber L: New reactions for combinatorial chemistry. Chimia (1996) (50):445.