Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Download PDF
Synthesis 2020; 52(18): 2698-2704
DOI: 10.1055/s-0040-1707148
DOI: 10.1055/s-0040-1707148
paper
Bio-inspired Functionalized Pyrrole-Pyridone Ensembles: Synthesis on the Platform of Acylethynylpyrroles
Authors
This work was supported by the Russian Science Foundation (Project 19-73-10063).
Further Information
Publication History
Received: 06 April 2020
Accepted after revision: 18 May 2020
Publication Date:
16 June 2020 (online)
Abstract
An efficient synthesis of pharmacologically oriented, functionalized pyrrole-pyridone ensembles by the reaction of available acylethynylpyrroles with methylene active amides in almost quantitative yields has been implemented. The cyclocondensation proceeds smoothly at room temperature in a KOH/DMSO superbase suspension.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707148.
- Supporting Information (PDF)
-
References
- 1a Lo Presti E, Boggia R, Feltrin A, Menozzi G, Dorigo P, Mosti L. Farmaco 1999; 54: 465
- 1b Fleming FF, Yao L, Ravikumar PC, Funk L, Shook BC. J. Med. Chem. 2010; 53: 7902
- 1c Hui-li G. Cardiovasc. Ther. 2011; 29: 153
- 2 Adcock AF, Trivedi G, Edmondson R, Spearman C, Yang L. J. Anal. Bioanal. Tech. 2015; 6: 249
- 3 Saari WS, Wai JS, Fisher TE, Thomas CM, Hoffman JM, Rooney CS, Smith AM, Jones JH, Bamberger DL. J. Med. Chem. 1992; 35: 3792
- 4 Rogawski MA. Epilepsy Curr. 2011; 11: 56
- 5a Imamura Y, Yukawa M, Kimura K.-I, Takahashi H, Suzuki Y, Ojika M, Sakagami Y, Tsuchiya E. Biosci., Biotechnol., Biochem. 2005; 69: 2213
- 5b Turner CD, Ciufolini MA. Beilstein J. Org. Chem. 2011; 7: 1475
- 6 Ratnavel RC, Squire RA, Boorman GC. J. Dermatol. Treat. 2007; 18: 88
- 7a Cocco MT, Congiu C, Onnis V. Eur. J. Med. Chem. 2000; 35: 545
- 7b Cheney IW, Yan S, Appleby T, Walker H, Vo T, Yao N, Hamatake R, Hong Z, Wu JZ. Bioorg. Med. Chem. Lett. 2007; 17: 1679
- 7c Abadi AH, Ibrahim TM, Abouzid KM, Lehmann J, Tinsley HN, Gary BD, Piazza GA. Bioorg. Med. Chem. 2009; 17: 5974
- 7d Abdel Motaal EA, Salem MA, Helal MH, El-Gaby MS. A. Orient. J. Chem. 2015; 31: 875
- 7e Badr MH, Rostom SA. F, Radwan MF. Chem. Pharm. Bull. 2017; 65: 442
- 8 Dragovich PS, Prins TJ, Zhou R, Brown EL, Maldonado FC, Fuhrman SA, Zalman LS, Tuntland T, Lee CA, Patick AK, Matthews DA, Hendrickson TF, Kosa MB, Liu B, Batugo MR, Gleeson J.-PR, Sakata SK, Chen L, Guzman MC, Meador JW, Ferre RA, Worland ST. J. Med. Chem. 2002; 45: 1607
- 9 Semple G, Andersson B.-M, Chhajlani V, Georgsson J, Johansson MJ, Rosenquist Å, Swanson L. Bioorg. Med. Chem. Lett. 2003; 13: 1141
- 10a Breinholt J, Ludvigsen S, Rassing BR, Rosendahl CN, Nielsen SE, Olsen CE. J. Nat. Prod. 1997; 60: 33
- 10b Li Q, Mitscher LA, Shen LL. Med. Res. Rev. 2000; 20: 231
- 10c Fujita Y, Oguri H, Oikawa H. Tetrahedron Lett. 2005; 46: 5885
- 11 Sośnicki JG, Idzik TJ. Synthesis 2019; 51: 3369
- 12a Mijin D, Ušćumlić G, Perišić-Janjić N, Trkulja I, Radetić M, Jovančić P. J. Serb. Chem. Soc. 2006; 71: 435
- 12b Karcı F, Karcı F. Dyes Pigm. 2008; 76: 147
- 13a Sellstedt M, Nyberg A, Rosenbaum E, Engström P, Wickström M, Gullbo J, Bergström S, Johansson LB. Å, Almqvist F. Eur. J. Org. Chem. 2010; 6171
- 13b Ershov OV, Fedoseev SV, Belikov MY, Ievlev MY. RSC Adv. 2015; 5: 34191
- 14 Litvinov VP, Krivokolysko SG, Dyachenko VD. Chem. Heterocycl. Compd. 1999; 35: 509
- 15a Torres M, Gil S, Parra M. Curr. Org. Chem. 2005; 9: 1757
- 15b Li S, Wang S. J. Heterocycl. Chem. 2008; 45: 1875
- 15c Kibou Z, Cheikh N, Villemin D, Choukchou-Braham N, Mostefa-Kara B, Benabdallah M. Int. J. Org. Chem. 2011; 1: 242
- 15d Hyster TK, Rovis T. Chem. Sci. 2011; 2: 1606
- 15e Ackermann L, Lygin AV, Hofmann N. Org. Lett. 2011; 13: 3278
- 15f Heravi MM, Hamidi H. J. Iran. Chem. Soc. 2013; 10: 265
- 15g Fujii M, Nishimura T, Koshiba T, Yokoshima S, Fukuyama T. Org. Lett. 2013; 15: 232
- 15h Chong Q, Xin X, Wang C, Wu F, Wan B. RSC Adv. 2013; 3: 21222
- 15i Mijin DŽ, Marković JM, Brković DV, Marinković AD. Hem. Ind. 2014; 68: 1
- 15j Hamama WS, Waly M, El-Hawary I, Zoorob HH. Synth. Commun. 2014; 44: 1730
- 15k Zhao X.-L, Yang K.-f, Zhang Y.-P, Fu X.-H, Xu L.-W. Tetrahedron Lett. 2016; 57: 321
- 15l Hirano K, Miura M. Chem. Sci. 2018; 9: 22
- 15m Hosseini H, Bayat M. RSC Adv. 2018; 8: 27131
- 15n El-Hashash MA, Shaban SS. Synth. Commun. 2019; 49: 2073
- 15o Liao C, Li J, Chen X, Lu J, Liu Q, Chen L, Huang Y, Li Y. Org. Biomol. Chem. 2020; 18: 1185
- 16a Rostom SA. F, Faidallah HM, Al-Saadi MS. Med. Chem. Res. 2011; 20: 1260
- 16b Rostom SA. F, Bekhit AA. Eur. J. Med. Chem. 2015; 92: 712
- 17 Trofimov BA, Mikhaleva AI, Ivanov AV, Skital’tseva EV, Ushakov IA, Vasil’tsov AV. Synthesis 2009; 587
- 18a Trofimov BA, Stepanova ZV, Sobenina LN, Mikhaleva AI, Ushakov IA. Tetrahedron Lett. 2004; 45: 6513
- 18b
Trofimov BA,
Sobenina LN.
Targets Heterocycl. Syst. 2009; 13: 92
Reference Ris Wihthout Link
- 19 Trofimov BA, Mikhaleva AI, Schmidt EY, Sobenina LN. Chemistry of Pyrroles . CRC Press; Boca Raton: 2014
- 20a Sobenina LN, Tomilin DN, Petrova OV, Mikhaleva AI, Trofimov BA. Russ. J. Org. Chem. 2013; 49: 356
- 20b Tomilin DN, Petrova OV, Sobenina LN, Mikhaleva AI, Trofimov BA. Chem. Heterocycl. Compd. 2013; 49: 341
- 21 Edwards MP, Kumpf RA, Kung P.-P, McAlpine IJ, Ninkovic S, Rui EY, Sutton SC, Tatlock JH, Wythes MJ, Zehnder LR. (Pfizer) WO2014097041A1, 2014 .
- 22 Shatsauskas AL, Abramov AA, Chernenko SA, Kostyuchenko AS, Fisyuk AS. Synthesis 2020; 52: 227
- 23 Nájera C, Sydnes LK, Yus M. Chem. Rev. 2019; 119: 11110
- 24 Buryi DS, Dotsenko VV, Levashov AS, Lukina DY, Strelkov VD, Aksenov NA, Aksenova IV, Netreba EE. Russ. J. Gen. Chem. 2019; 89: 886
- 25a Clarke PA, Santos S, Martin WH. C. Green Chem. 2007; 9: 438
- 25b Xiang H, Chen Y, He Q, Xie Y, Yang C. RSC Adv. 2013; 3: 5807
- 26 Wang K, Nguyen K, Huang Y, Dömling A. J. Comb. Chem. 2009; 11: 920