Design of a versatile multicomponent reaction leading to 2-amino-5-ketoaryl pyrroles

Chemical Biology and Drug Design

Volumn 75, Issue 3, 2010, Pages 277-283

  Wang, Kan ^a   Dömling, Alexander ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

2 aminopyrrole; Aminoacetophenone sulfonamides; Cyanoacetamides; Multicomponent reaction

Indexed keywords

(5 AMINO 3 (4 CHLOROPHENYL) 4 (PYRROLIDINE 1 CARBONYL) 1H PYRROL 2 YL)(PHENYL)METHANONE; 2 AMINO 5 BENZOYL 4 (4 CHLOROPHENYL) 1H PYRROLE 3 CARBONITRILE; 2 AMINO 5 BENZOYL 4 (4 CHLOROPHENYL) N (PROP 2 YNYL) 1H PYRROLE 3 CARBOXAMIDE; 2 AMINO 5 BENZOYL N BENZYL 4 (4 CHLOROPHENYL) 1H PYRROLE 3 CARBOXAMIDE; 2 AMINO 5 BENZOYL N BENZYL 4 (4 FLUOROPHENYL) 1H PYRROLE 3 CARBOXAMIDE; 2 AMINO 5 BENZOYL N BENZYL 4 (NAPHTHALEN 1 YL) 1H PYRROLE 3 CARBOXAMIDE; 2 AMINO 5 BENZOYL N BUTYL 4 (4 CHLOROPHENYL) 1H PYRROLE 3 CARBOXAMIDE; 2 AMINO 5 BENZOYL N BUTYL 4 (PYRIDIN 2 YL) 1H PYRROLE 3 CARBOXAMIDE; 2 AMINO 5 BENZOYL N CYCLOHEXYL 4 (PYRIDIN 3 YL) 1H PYRROLE 3 CARBOXAMIDE; 2 AMINO 5 BENZOYL N CYCLOPROPYL 4 (PYRIDIN 4 YL) 1H PYRROLE 3 CARBOXAMIDE; 2 AMINO N BENZYL 5 (4 BROMOBENZOYL) 4 (4 CHLORO 2 HYDROXYPHENYL) 1H PYRROLE 3 CARBOXAMIDE; ACETOPHENONE DERIVATIVE; ALDEHYDE DERIVATIVE; METHYL 2 AMINO 5 BENZOYL 4 (4 CHLOROPHENYL) 1H PYRROLE 3 CARBOXYLATE; N [2 (1H INDOL 3 YL)ETHYL] 2 AMINO 5 BENZOYL 4 PHENYL 1H PYRROLE 3 CARBOXAMIDE; PYRROLE DERIVATIVE; SULFONAMIDE; TRIETHYLAMMONIUM 2 AMINO 5 BENZOYL 4 (4 CHLOROPHENYL) 1H PYRROLE 3 CARBOXYLATE; UNCLASSIFIED DRUG; ACETIC ACID DERIVATIVE; ALDEHYDE; CYANOACETIC ACID; DICYANMETHANE; NITRILE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG DESIGN; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; CHEMISTRY; SYNTHESIS;

ACETATES; ALDEHYDES; DRUG DESIGN; NITRILES; PYRROLES; SULFONAMIDES;

EID: 76049119539     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2009.00942.x     Document Type: Article

References (20)

1. Kawashima K., Enomoto H., Ishizaka N., Yamamoto M., Kudou K., Murai M., Inaba T., Okamoto K. (2008) Preparation of pyrrole derivatives containing ureido and aminocarbonyl moiety as IL-6 production inhibitors. WO 2008105408. Chem Absrt 149 : 332196.
2. Enomoto H., Kawashima K., Kudou K., Yamamoto M., Murai M., Inaba T., Ishizaka N. (2008) Preparation of novel indole derivatives having inhibitory activity on I.kappa.b kinase beta. WO 2008087933. Chem Absrt 149 : 176178.
3. Dominguez C., Chen G.Q., Xi N., Xu S.M., Han N.H., Liu Q.Y., Huang Q., Siegmund A., Handley M., Liu L.B., Kiselyov A.S. (2001) 1-(Aminophenyl)-2- pyrrolidones as integrin inhibitors. WO 2001044230. Chem Absrt 135 : 61230.
4. Tang P.C., Ramphal J.Y., Harris G.D. Jr., Nematalla A.S. (1998) Preparation of 2-(1,2,4-triazol-3-ylthio)-, 2-(5-tetrazolylthio)-, 2-(1,3,4-thiadiazol-2-ylthio)thiazole compounds and methods of modulating signal transduction. WO9827092. Chem Absrt 129 : 95500.
5. Menta E., Conti M., Pescalli N. (2000) Preparation of furanones, thiophenones and pyranones having antitumor activity. WO2000053581. Chem Absrt 133 : 222576.
6. Nishitani Y., Yamano Y. (2003) Preparation of broad-spectrum cephem compounds. WO 2003078440. Chem Absrt 139 : 261088.
7. Hendlich M., Rippmann F., Barnickel G., Hemm K., Aberer K. (1996) RELIBase - an object-oriented comprehensive receptor-ligand database. Fold Des 1 (Suppl. S30.
8. Piloty O. (1910) Synthese von Pyrrolderivaten: Pyrrole aus Succinylobernsteinsäureester, Pyrrole aus Azinen. Chem Ber 43 : 489 498.
9. Robinson G.M., Robinson R. (1918) LIV. - a new synthesis of tetraphenylpyrrole. J Chem Soc Trans 113 : 639 644.
10. Braun R.U., Müller T.J.J. (2004) Coupling-Isomerization-Stetter and coupling-Isomerization -Stetter-Paal-Knorr sequences - a multicomponent approach to furans and pyrroles. Synthesis 2391 2406.
11. Yavari I., Kowsari E. (2008) Task-specific basic ionic liquid: a reusable and green catalyst for one-pot synthesis of highly functionalized pyrroles in aqueous media. Synlett 897 899.
12. Nair V., Vinod A.U., Rajesh C. (2001) A novel synthesis of 2-aminopyrroles using a three-component reaction. J Org Chem 66 : 4427 4429.
13. Paal C. (1885) Synthese von Thiophen- und Pyrrolderivaten. Ber Dtsch Chem Ges 18 : 367 371.
14. Knorr L. (1885) Action of ethylic diacetosuccinate on ammonia and primary amines. Ber Dtsch Chem Ges 18 : 299 311.
15. Pichler H., Folkers G., Roth H.J., EgePa K. (1986) Synthese von 7-unsubstituierten 7H-Pyrrolo[2,3-d] - pyrimidinen. Liebigs Ann Chem 1485 1505.
16. Wang K., Nguyen K., Huang Y.J., Doemling A. (2009) Cyanoacetamide MCR (I): parallel synthesis of arrays of cyanoacetamides. J Comb Chem 11 : 920 927.
17. Shestopalov A.M., Shestopalov A.A., Rodinovskayaa L.A. (2008) Multicomponent reactions of carbonyl compounds and derivatives of cyanoacetic acid: synthesis of carbo- and heterocycles. Synthesis 1 25.
18. Griffiths-Jones C.M., Hopkin M.D., Jonsson D., Ley S.V., Tapolczay D.J., Vickerstaffe E., Ladlow M. (2007) Fully automated flow-through synthesis of secondary sulfonamides in a binary reactor system. J Comb Chem 9 : 422 430.
19. Evans M.A., Smith D.C., Holub J.M., Argenti A., Hoff M., Dalglish G.A., Wilson D.L., Taylor B.M., Berkowitz J.D., Burnham B.S., Krumpe K., Gupton J.T., Scarlett T.C., Durham R.W. Jr., Hall I.H. (2003) Synthesis and cytotoxicity of substituted ethyl 2-phenacyl-3-phenylpyrrole-4-carboxylates. Arch Pharm 336 : 181 190.
20. Magedov I.V., Luchetti G., Evdokimov N.M., Manpadi M., Steelant W.F.A., Van slambrouck S., Tongwa P., Antipin M.Y., Kornienko A. (2008) Novel three-component synthesis and antiproliferative properties of diversely functionalized pyrrolines. Bioorg Med Chem Lett 18 : 1392 1396.