Approach to the library of 3-hydroxy-1,5-dihydro-2H-pyrrol-2-ones through a three-component condensation

ACS Combinatorial Science

Volumn 14, Issue 12, 2012, Pages 631-635

  Ryabukhin, Sergey V ^a   Panov, Dmitriy M ^a,b   Plaskon, Andrey S ^b   Grygorenko, Oleksandr O ^a,b  

^a TARAS SHEVCHENKO NATIONAL UNIVERSITY OF KYIV   (Ukraine)

^b ENAMINE LTD   (Ukraine)

Author keywords

aldehyde; amine; chlorotrimethylsilane; condensation; multicomponent reaction; pyrrole

Indexed keywords

ALDEHYDE; AMINE; ESTER; PYRROLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; MOLECULAR LIBRARY; SYNTHESIS;

ALDEHYDES; AMINES; ESTERS; MOLECULAR STRUCTURE; PYRROLES; SMALL MOLECULE LIBRARIES;

EID: 84870865088     PISSN: 21568952     EISSN: None     Source Type: Journal    
DOI: 10.1021/co300082t     Document Type: Article

References (62)

1. Bannwarth, W. and Hinzen, B., Eds. Combinatorial Chemistry: From Theory to Application; Wiley-VCH: Weinheim, Germany, 2006.
2. Zhu, J. and Bienaymé, H., Eds. Multicomponent Reactions; Wiley-VCH: Weinheim, Germany, 2005.
3. Armstrong, R. W.; Combs, A. P.; Tempest, P. A.; Brown, S. D.; Keating, T. Multiple-component condensation strategies for combinatorial library synthesis Acc. Chem. Res. 1996, 29, 123-131
4. Tietze, L. F.; Lieb, M. E. Domino reactions for library synthesis of small molecules in combinatorial chemistry Curr. Opin. Chem. Biol. 1998, 2, 363-371 (Pubitemid 128423240)
5. Dömling, A. Isocyanide-based multi component reactions in combinatorial chemistry Comb. Chem. High Throughput Screening 1998, 1, 1-22 (Pubitemid 128541765)
6. Dax, S. L.; McNally, J. J.; Youngman, M. A. Multi-component methodologies in solid-phase organic synthesis Curr. Med. Chem. 1999, 6, 255-270 (Pubitemid 29159606)
7. Tietze, L. F.; Modi, A. Multicomponent domino reactions for the synthesis of biologically active natural products and drugs Med. Res. Rev. 2000, 20, 304-322 (Pubitemid 30430010)
8. Bienayme, H.; Hulme, C.; Oddon, G.; Schmitt, P. Maximizing synthetic efficiency: multi-component transformations lead the way Chem.î- ̧Eur. J. 2000, 6, 3321-3329
9. Ugi, I.; Heck, S. The multicomponent reactions and their libraries for natural and preparative chemistry Comb. Chem. High Throughput Screening 2001, 4, 1-34 (Pubitemid 32405667)
10. Weber, L. Multi-component reactions and evolutionary chemistry Drug Discovery Today 2002, 7, 143-147
11. Domling, A. Recent advances in isocyanide-based multicomponent chemistry Curr. Opin. Chem. Biol. 2002, 6, 306-313 (Pubitemid 34522055)
12. Mohammat, M. F.; Shaameri, Z.; Hamzah, A. S. Synthesis of 2,3-dioxo-5-(substituted)arylpyrroles and their 2-oxo-5-aryl-3-hydrazone pyrrolidine derivatives Molecules 2009, 14, 250-256
13. Henkel, B.; Lis, M.; Illgen, K.; Eckl, R. Macrocycles via Doebner reaction followed by macrolactonization Synlett 2006, 1315-1318 (Pubitemid 43944598)
14. Kocharyan, S. T.; Churkina, N. P.; Razina, T. L.; Karapetyan, V. E.; Ogandzanyan, S. M.; Voskanyan, V. S.; Babayan, A. T. New method for synthesis of 3-pyrrolin-2-one derivatives Chem. Heterocycl. Compd. 1994, 30, 1165-1169
15. Gein, V. L.; Popov, A. V.; Andreichikov, Yu. S. Formation of 1,5-diaryl-3-arylamino-4-carboxy-methyl-2,5-dihydropyrrol-2-ones by reaction between 2-ketoglutaric acid and Schiff bases J. Gen. Chem. USSR 1992, 62, 1378
16. Milyutin, A. V.; Gein, V. L.; Andreichikov, Yu. S. Formation of 1-aryl-4-benzoyl-5-phenyltetrahydro-pyrrole-2,3-diones in the reactions of N -(2-pyridyl)-amide of benzoylpyruvic acid with Schiff bases J. Gen. Chem. USSR 1992, 62, 2172
17. Gein, V. L.; Popov, A. V.; Andreichikov, Yu. S. Reaction of α-ketoglutaric acid with Schiff bases J. Gen. Chem. USSR 1992, 62, 2291-2295
18. Andreichikov, Yu. S.; Gein, V. L.; Konâshina, L. O.; Shapetâko, N. N. Five-membered 2,3-dioxoheterocycles. XVI. Synthesis of 1,4-disubstituted 5-aryltetrahydropyrrole-2,3-diones based on the reaction of diethoxalylacetone with azomethines J. Org. Chem. USSR 1989, 25, 2238-2243
19. Taylor, W. C.; Vadasz, A. The reactions of aromatic Schiff bases with dimethyl acetylenedicarboxylate. II. Reaction in the presence of water Aust. J. Chem. 1982, 35, 1227-1230
20. Reddy, T. R. K.; Li, C.; Guo, X.; Myrvang, H. K.; Fischer, P. M.; Dekker, L. V. Design, synthesis, and structureâ"activity relationship exploration of 1-substituted 4-aroyl-3-hydroxy-5-phenyl-1 H -pyrrol-2(5 H)-one analogues as inhibitors of the annexin A2â"S100A10 protein interaction J. Med. Chem. 2011, 54, 2080-2094
21. Ma, K.; Wang, P.; Fu, W.; Zhou, L.; Chu, Y.; Ye, D.; Wan, X. Rational design of 2-pyrrolinones as inhibitors of HIV-1 integrase Bioorg. Med. Chem. Lett. 2011, 21, 6724-6727
22. Pace, P.; Spieser, S. A. H.; Summa, V. 4-Hydroxy-5-pyrrolinone-3- carboxamide HIV-1 integrase inhibitors Bioorg. Med. Chem. Lett. 2008, 18, 3865-3869
23. Yangthara, B.; Mills, A.; Chatsudthipong, V.; Tradtrantip, L.; Verkman, A. S. Small-molecule vasopressin-2 receptor antagonist identified by a G-protein coupled receptor "pathway" screen Mol. Pharmacol. 2007, 72, 86-94 (Pubitemid 46998527)
24. Kozâminykh, V. O.; Igidov, N. M.; Zykova, S. S.; Kolla, V. E.; Shuklina, N. S.; Odegova, T. F. Synthesis and pharmacological activity of 3-hydroxy-1,5-diaryl-4-pivaloyl-2,5-dihydro-2-pyrrolones Pharm. Chem. J. 2002, 36, 188-191 (Pubitemid 35256054)
25. Gein, V. L.; Popov, A. V.; Kolla, W. E.; Popova, N. A. Synthesis and biological activity of 1,5-diaryl-3-alkylamino-4-carboxymethyl-2,5- dihydropyrrol-2-ones and 1,5-diaryl-4-carboxy-methyltetrahydropyrrol-2,3-diones Pharmazie 1993, 48, 107-109 (Pubitemid 23122686)
26. Vydzhak, R. N.; Panchishyn, S. Ya. Synthesis of 1-aryl-2-[2- (dimethylamino)ethyl]-1,2-dihydrochromeno[2,3- c ]pyrrole-3,9-diones and their analogs Russ. J. Gen. Chem. 2010, 80, 323-329
27. Gein, V. L.; Kasimova, N. N.; Vakhrin, M. I.; Aliev, Z. G. Three-component reaction of methyl 2,4-dioxo-4-phenylbutanoate and methyl 2,4-dioxopentanoate with aromatic aldehydes and propane-1,2-diamine and chemical properties of the products Russ. J. Org. Chem. 2010, 46, 875-883
28. Sakhno, Y. I.; Desenko, S. M.; Shishkina, S. V.; Shishkin, O. V.; Chebanov, V. A.; Kappe, O. C.; Sysoyev, D. O.; Groth, U. Multicomponent cyclocondensation reactions of aminoazoles, arylpyruvic acids and aldehydes with controlled chemoselectivity Tetrahedron 2008, 64, 11041-11049
29. Guseinov, F. N.; Burangulova, R. N.; Mukhamedzyanova, E. F.; Strunin, B. P.; Sinyashin, O. G.; Litvinov, I. A.; Gubaidullin, A. T. Synthesis and molecular structure of 3,7-dimethyl-2-[ N -(4-methylpyridyl-2)-4-hydroxy-3- methyl-5-oxopyrrolen-3-yl-2]imidazo[1,2- a ]pyridine Chem. Het. Comp. 2006, 42, 943-947
30. Gein, V. L.; Kasimova, N. N.; Potemkin, K. D. Simple three-component synthesis of 4-acyl-1-(2-aminoethyl)-5-aryl-3-hydroxy-2,5-dihydropyrrol-2(1 H)-ones Russ. J. Gen. Chem. 2002, 72, 1150-1151 (Pubitemid 37116391)
31. Bagrov, F. V. Reaction of 5-aryl-4-acetyl-1-methyltetrahydropyrrole-2,3- diones with primary amines and nitrophenyl-, diphenylphosphinyl-, and diphenoxyphosphinoylhydrazines Russ. J. Gen. Chem. 1998, 68, 1217-1220 (Pubitemid 128447545)
32. Gein, V. L.; Kasimova, N. N.; Voronina, E. V.; Gein, L. F. Synthesis and antimicrobial activity of 5-aryl-4-acyl-1-(N, N -dimethylaminoethyl)-3-hydroxy- 3-pyrrolin-2-ones Pharm. Chem. J. 2001, 35, 151-154 (Pubitemid 33048748)
33. Mohammat, M. F.; Najim, N.; Mansor, N. S.; Sarman, S.; Shaameri, Z.; Zain, M. M.; Hamzah, A. S. Synthesis and bioactivity of some 2-oxo-5-aryl-3-hydrazone and 2-oxo-5-aryl-4-hydrazone pyrrolidine derivatives Arkivoc 2011, 429-438
34. Gein, V. L.; Tsyplyakova, E. P.; Stashina, G. A.; Bakulev, V. A. Reactions of methyl 4-hetaryl-2,4-dioxobutanoates with a mixture of aminoazole and aromatic (heteroaromatic) aldehyde Russ. J. Org. Chem. 2008, 44, 478-480
35. Vydzhak, R. N.; Panchishin, S. Ya. Synthesis of 2-phenyl-5,6- dihydropyrano[2,3- c ]pyrrole-4,7-dione derivatives Russ. J. Gen. Chem. 2008, 78, 1641-1642
36. Metten, B.; Kostermans, M.; Baelen, G.; Van; Smet, M.; Dehaen, W. Synthesis of 5-aryl-2-oxopyrrole derivatives as synthons for highly substituted pyrroles Tetrahedron 2006, 62, 6018-6028 (Pubitemid 43728081)
37. Silina, T. A.; Pulina, N. A.; Gein, L. F.; Gein, V. L. Simple three-component synthesis of 4-acyl-5-phenyl-1-(2-heteryl)-3-hydroxy-3-pyrrolin- 2-ones Chem. Heterocycl. Compd. 1998, 34, 739-739
38. Gein, V. L.; Gein, L. F.; Porseva, N. Yu.; Voronina, E. V.; Vakhrin, M. I.; Potemkin, K. D.; Kolla, V. E.; Drovosekova, L. P.; Milyutin, A. V.; Shchuklina, N. S.; Veikhman, G. A. Synthesis and pharmacological activity of 1-substituted 5-aryl-4-acyl-3-hydroxy-3-pyrrolin-2-ones Pharm. Chem. J. 1998, 32, 477-479 (Pubitemid 128699226)
39. Andreichikov, Yu. S.; Gein, V. L.; Shumilovskikh, E. V. Five-membered 2,3-dioxoheterocycles 15. Synthesis and [1,3]-sigmatropic rearrangement of 1,5-diaryl-3-diphenylmethoxy-4-ethoxycarbonyl-2,5-dihydropyrrol-2-ones Chem. Heterocycl. Compd. 1990, 26, 627-630
40. Gein, V. L.; Kasimova, N. N.; Panina, M. A.; Voronina, E. V. Synthesis and antibacterial activity of 1-(5-aryl-4-benzoyl-3-hydroxy-2-oxo-3-pyrrolin-1- yl)-2-(3-benzoylmethylene-2-oxopiperazin-1-yl)ethanes Pharm. Chem. J. 2006, 40, 410-412
41. Gein, V. L.; Pitirimova, S. G.; Voronina, E. V.; Porseva, N. Yu.; Pantsurkin, V. I. Synthesis and antibacterial activity of 1-substituted 5-aryl-4-aroyl-3-hydroxy-3-pyrrolin-2-ones Pharm. Chem. J 1997, 31, 603-605
42. Gein, V. L.; Shumilovskikh, E. V.; Andreichikov, Yu. S.; Saraeva, R. F.; Korobchenko, L. V.; Vladyko, G. V.; Boreko, E. I. Synthesis of 4-substituted 1-methyl-5-aryl- and 1,5-diaryltetrahydropyrrole-2,3-diones and their antiviral action Pharm. Chem. J. 1991, 25, 884-887
43. Feng, Z.; Li, X.; Zheng, G.; Huang, L. Synthesis and activity in enhancing long-term potentiation (LTP) of Clausenamide stereoisomers Bioorg. Med. Chem. Lett. 2009, 19, 2112-2115
44. Thormann, M. Peptide deformylase (Pdf) inhibitors 4. PCT Int. Pat. Appl. WO 2006131303, 2006.
45. Berecibar, A.; Guedat, P.; Mohamed-Arab, C. 1-(6-Member azo-heterocyclic)-pyrrolin-2-one compounds as inhibitors of hepatitis c ns5b polymerase, the pharmaceutical composition thereof and their therapeutic use. PCT Int. Pat. Appl. WO 2011004017, 2011.
46. Zou, D.; Dasse, O.; Evans, J.; Higgins, P.; Kintigh, J.; Knerr, L.; Kondru, R.; Schwartz, E.; Zhai, H.-X. Pyrrolidinone Derivatives. PCT Int. Pat. Appl. WO 2003030897, 2003.
47. Thormann, M. Pyrrolones that act as peptide deformylase (Pdf) inhibitors. PCT. Int. Pat. Appl. WO 2006131340, 2006.
48. Nadin, A.; Hattotuwagama, C.; Churcher, I. Lead-oriented synthesis: a new opportunity for synthetic chemistry Angew. Chem., Int. Ed. 2012, 51, 1114-1122
49. Gleeson, M. P. Generation of a set of simple, interpretable ADMET rules of thumb J. Med. Chem. 2008, 51, 817-834 (Pubitemid 351304691)
50. Oprea, T. I.; Davis, A. M.; Teague, S. J.; Leeson, P. D. Is there a difference between leads and drugs? A historical perspective J. Chem. Inf. Comp. Sci. 2001, 41, 1308-1315
51. Leeson, P. D.; Springthorpe, B. The influence of drug-like concepts on decision-making in medicinal chemistry Nat. Rev. Drug Discovery 2007, 6, 881-890 and references therein (Pubitemid 350042396)
52. Polinsky, A. In Practice of Medicinal Chemistry, 3 rd ed.; Wermuth, C. G., Ed.; Academic Press/Elsevier: Amsterdam, 2008; pp 244-254.
53. Volochnyuk, D. M.; Ryabukhin, S. V.; Plaskon, A. S.; Grygorenko, O. O. Organosilicon compounds as water scavengers in reactions of carbonyl compounds Synthesis 2009, 3719-3743 and references therein
54. Ryabukhin, S. V.; Plaskon, A. S.; Bondarenko, S. S.; Ostapchuk, E. N.; Grygorenko, O. O.; Shishkin, O. V.; Tolmachev, A. A. Acyl pyruvates as synthons in the Biginelli reaction Tetrahedron Lett. 2010, 51, 4229-4232
55. Ryabukhin, S. V.; Plaskon, A. S.; Boron, S. Yu.; Volochnyuk, D. M.; Tolmachev, A. A. Aminoheterocycles as synthons for combinatorial Biginelli reactions Mol. Diversity 2011, 15, 181-195
56. Ryabukhin, S. V.; Naumchik, V. S.; Plaskon, A. S.; Grygorenko, O. O.; Tolmachev, A. A. 3-haloquinolines by friedlander reaction of α-haloketones J. Org. Chem. 2011, 76, 5774-5781
57. Plaskon, A. S.; Grygorenko, O. O.; Ryabukhin, S. V. Recyclizations of 3-formylchromones with binucleophiles Tetrahedron 2012, 68, 2743-2757
58. Ryabukhin, S. V.; Plaskon, A. S.; Volochnyuk, D. M.; Tolmachev, A. A. Synthesis of fused imidazoles and benzothiazoles from (hetero)aromatic ortho -diamines or ortho -aminothiophenole and aldehydes promoted by chlorotrimethylsilane Synthesis 2006, 3715-3726 (Pubitemid 44810836)
59. Ryabukhin, S. V.; Plaskon, A. S.; Volochnyuk, D. M.; Pipko, S. E.; Shivanyuk, A. N.; Tolmachev, A. A. Combinatorial Knoevenagel reactions J. Comb. Chem. 2007, 9, 1073-1078
60. Ryabukhin, S. V.; Plaskon, A. S.; Ostapchuk, E. N.; Volochnyuk, D. M.; Tolmachev, A. A. N -substituted ureas and thioureas in Biginelli reaction promoted by chlorotrimethylsilane: convenient synthesis of N1 -alkyl, N1 -aryl- and N1, N3 -dialkyl-3,4-Dihydropyrimidin-2(1 H)-(thio)ones Synthesis 2007, 417-427
61. 3-substituted 1,3-dicarbonyl compounds in the Biginelli reaction promoted by chlorotrimethylsilane J. Fluorine Chem. 2008, 129, 625-631
62. Instant JChem was used for prediction of the physicochemical properties of the library members: Instant JChem, version 3.0; ChemAxon: Budapest, Hungary, 2009; http://www.chemaxon.com.