Straightforward Synthesis of Novel 4-Styrylquinolines/4-Styrylquinolin-2-ones and 9-Styryldihydroacridin-1(2H)-ones from Substituted 2′-Aminochalcones

Angie Meléndez; Esteban Plata; Diego Rodríguez; Diana Ardila; Sergio A. Guerrero; Lina M. Acosta; Justo Cobo; Manuel Nogueras; Alirio Palma

doi:10.1055/s-0039-1707985

Synthesis, Inhaltsverzeichnis

Synthesis 2020; 52(12): 1804-1822
DOI: 10.1055/s-0039-1707985

paper

Straightforward Synthesis of Novel 4-Styrylquinolines/4-Styrylquinolin-2-ones and 9-Styryldihydroacridin-1(2H)-ones from Substituted 2′-Aminochalcones

Authors

Angie Meléndez

^aLaboratorio de Síntesis Orgánica, Escuela de Química, Universidad Industrial de Santander, Carrera 27, Calle 9, A.A 678, 680002 Bucaramanga, Colombia eMail: apalma@uis.edu.co
Esteban Plata

^aLaboratorio de Síntesis Orgánica, Escuela de Química, Universidad Industrial de Santander, Carrera 27, Calle 9, A.A 678, 680002 Bucaramanga, Colombia eMail: apalma@uis.edu.co
Diego Rodríguez

^aLaboratorio de Síntesis Orgánica, Escuela de Química, Universidad Industrial de Santander, Carrera 27, Calle 9, A.A 678, 680002 Bucaramanga, Colombia eMail: apalma@uis.edu.co
Diana Ardila

^aLaboratorio de Síntesis Orgánica, Escuela de Química, Universidad Industrial de Santander, Carrera 27, Calle 9, A.A 678, 680002 Bucaramanga, Colombia eMail: apalma@uis.edu.co
Sergio A. Guerrero

^aLaboratorio de Síntesis Orgánica, Escuela de Química, Universidad Industrial de Santander, Carrera 27, Calle 9, A.A 678, 680002 Bucaramanga, Colombia eMail: apalma@uis.edu.co
Lina M. Acosta

^aLaboratorio de Síntesis Orgánica, Escuela de Química, Universidad Industrial de Santander, Carrera 27, Calle 9, A.A 678, 680002 Bucaramanga, Colombia eMail: apalma@uis.edu.co
Justo Cobo

^bInorganic and Organic Department, University of Jaén, Campus Las Lagunillas s/n, 23071 Jaén, Spain
Manuel Nogueras

^bInorganic and Organic Department, University of Jaén, Campus Las Lagunillas s/n, 23071 Jaén, Spain
Alirio Palma∗

^aLaboratorio de Síntesis Orgánica, Escuela de Química, Universidad Industrial de Santander, Carrera 27, Calle 9, A.A 678, 680002 Bucaramanga, Colombia eMail: apalma@uis.edu.co

Abstract

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Abstract

An alternative and efficient one-step approach to develop small libraries of polysubstituted 4-styrylquinolines/4-styrylquinolin-2-ones and 9-styryldihydroacridin-1-ones is described. According to this approach, new series of these compounds were straightforwardly synthesized in high yields starting from synthetically available 2′-aminochalcones and 1,3-dicarbonyl compounds in glacial acetic acid as a catalyst via the Friedländer reaction. Our approach also offers an expeditious way to access novel molecular hybrids in whose structures styryl and chalcone fragments are attached at the C4 and C3 positions, respectively, of the quinoline ring. All synthesized compounds were fully characterized by means of IR, HRMS and NMR techniques, and most were screened at the National Cancer Institute, USA, for their antitumor activity.

Key words

4-styrylquinolines - Friedländer reaction - 2′-aminochalcones - quinoline–chalcone hybrids - Claisen–Schmidt condensation

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References

1a Michael JP. Nat. Prod. Rep. 2007; 24: 223
1b Michael JP. Nat. Prod. Rep. 2008; 25: 166
1c Salomon VR, Lee H. Curr. Med. Chem. 2011; 18: 1488

2a Upadhayaya RS, Vandavasi JK, Vasireddy NR, Sharma V, Dixit SS, Chattopadhyaya J. Bioorg. Med. Chem. 2009; 17: 2830
2b Souza MV. N. D, Pais KC, Kaiser CR, Peralta MA, Ferreira MD. L, Lourenco MC. S. Bioorg. Med. Chem. 2009; 17: 1474
2c Eswaran S, Adhikari AV, Chowdhury IH, Pal NK, Thomas KD. Eur. J. Med. Chem. 2010; 45: 3374
2d Lam K.-H, Gambari R, Lee KK.-H, Chen Y.-X, Kok SH.-L, Wong RS.-M, Lau F.-Y, Cheng C.-H, Wong W.-Y, Bian Z.-X, Chan AS.-C, Tang JC.-O, Chui C.-H. Bioorg. Med. Chem. Lett. 2014; 24: 367
2e Zhang G.-F, Liu X, Zhang S, Pan B, Liu M.-L. Eur. J. Med. Chem. 2018; 146: 599

3a Raynes K, Foley M, Tilley L, Deady LW. Biochem. Pharmacol. 1996; 52: 551
3b Kumar S, Bawa S, Gupta H. Mini-Rev. Med. Chem. 2009; 9: 1648
3c Kaur K, Jain M, Reddy RP, Jain R. Eur. J. Med. Chem. 2010; 45: 3245
3d Modapa S, Tusi Z, Sridhar D, Kumar A, Siddiqi MI, Srivastava K, Rizvi A, Tripathi R, Puri SK, Keshava GB. S, Shukla PK, Batra S. Bioorg. Med. Chem. 2009; 17: 203
3e Ekoue-Kovi K, Yearick K, Iwaniuk DP, Natarajan JK, Alumasa J, de Dios AC, Roepe PD, Wolf C. Bioorg. Med. Chem. 2009; 17: 270
3f Okombo J, Chibale K. MedChemComm 2018; 9: 437

4a Meléndez Gómez CM, Kouznetsov VV, Sortino MA, Álvarez SL, Zacchino SA. Bioorg. Med. Chem. 2008; 16: 7908
4b Musiol R, Serda M, Hensel-Bielowka S, Polanski J. Curr. Med. Chem. 2010; 17: 1960
4c Kumar S, Bawa S, Drabu S, Panda BP. Med. Chem. Res. 2011; 20: 1340

5a Baba A, Kawamura N, Makino H, Ohta Y, Taketomi S, Sohda T. J. Med. Chem. 1996; 39: 5176
5b Chen Y, Zhao Y, Lu C, Tzeng C, Wang JP. Bioorg. Med. Chem. 2006; 14: 4373
5c Gilbert AM, Bursavich MG, Lombardi S, Georgiadis KE, Reifenberg E, Flannery C, Morris EA. Bioorg. Med. Chem. Lett. 2008; 18: 6454

6a Fakhfakh MA, Fournet A, Prina E, Mouscadet J.-F, Franck X, Hocquemiller R, Figadère B. Bioorg. Med. Chem. 2003; 11: 5013
6b Ghosh J, Swarup V, Saxena A, Das S, Hazra A, Paira P, Banerjee S, Mondal NB, Basu A. Int. J. Antimicrob. Agents 2008; 32: 349

7a Fournet A, Barrios AA, Muñoz V, Hocquemiller R, Cavé A, Bruneton J. Antimicrob. Agents Chemother. 1993; 37: 859
7b Franck X, Fournet A, Prina E, Mahieux R, Hocquemiller R, Figadère B. Bioorg. Med. Chem. Lett. 2004; 14: 3635

8a Hu B, Jetter J, Kaufman D, Singhaus R, Bernotas R, Unwalla R, Quinet E, Savio D, Halpern A, Basso M, Keith J, Clerin V, Chen L, Liu QY, Feingold I, Huselton C, Azam F, Nilsson AG, Wilhelmsson A, Nambi P, Wrobel J. Bioorg. Med. Chem. 2007; 15: 3321
8b Cai Z, Zhou W, Sun L. Bioorg. Med. Chem. 2007; 15: 7809
8c Bernotas RC, Singhaus RR, Kaufman DH, Ullrich J, Fletcher HIII, Quinet E, Nambi P, Unwalla R, Wilhelmsson A, Goos-Nilsson A, Farnegardh M, Wrobel J. Bioorg. Med. Chem. 2009; 17: 1663

9a Xia Y, Yang Z.-Y, Xia P, Bastow KF, Tachibana Y, Kuo S.-C, Hamel E, Hackl T, Lee K.-H. J. Med. Chem. 1998; 41: 1155
9b Srivastava V, Negi AS, Kumar JK, Gupta MM, Khanuja SP. S. Bioorg. Med. Chem. 2005; 13: 5892
9c Burnett AK, Kell J. Drugs Today 2007; 43: 795
9d Scott DA, Balliet CL, Cook DJ, Davies AM, Gero TW, Omer CA, Poondru S, Theoclitou ME, Tyurin B, Zinda MJ. Bioorg. Med. Chem. Lett. 2009; 19: 697
9e Mai A, Rotili D, Tarantino D, Nebbioso A, Castellano S, Sbardella G, Tini M, Altucci L. Bioorg. Med. Chem. Lett. 2009; 19: 1132
9f Miller LM, Mayer SC, Berger DM, Boschelli DH, Boschelli F, Di L, Du X, Dutia M, Floyd MB, Johnson M, Kenny CH, Krishnamurthy G, Moy F, Petusky S, Tkach D, Torres N, Wu B, Xu W. Bioorg. Med. Chem. Lett. 2009; 19: 62
9g Solomon VR, Lee H. Eur. J. Pharmacol. 2009; 625: 220
9h Marganakop SB, Kamble RR, Taj T, Kariduraganvar MY. Med. Chem. Res. 2012; 21: 185
9i Insuasty B, Becerra D, Quiroga J, Abonia R, Nogueras M, Cobo J. Eur. J. Med. Chem. 2013; 60: 1
9j Afzal O, Kumar S, Haider R, Ali R, Kumar R, Jaggi M, Bawa S. Eur. J. Med. Chem. 2015; 97: 871
9k Cortes JE, Apperley JF, DeAngelo DJ, Deininger MW, Kota VK, Rousselot P, Gambacorti-Passerini C. J. Hematol. Oncol. 2018; 11: 143

10a Mekouar K, Mouscadet JF, Desmaële D, Subra F, Leh H, Savouré D, Auclair C, d’Angelo J. J. Med. Chem. 1998; 41: 2846
10b Zouhiri F, Mouscadet JF, Mekouar K, Desmaële D, Savouré D, Leh H, Subra F, Le Bret M, Auclair C, d’Angelo J. J. Med. Chem. 2000; 43: 1533
10c Polanski J, Zouhiri F, Jeanson L, Desmaële D, d’Angelo J, Mouscadet JF, Gieleciak R, Gasteiger J, Le Bret M. J. Med. Chem. 2002; 45: 4647

11 Cieslik W, Musiol R, Nycz JE, Jampilek J, Vejsova M, Wolff M, Machura B, Polanski J. Bioorg. Med. Chem. 2012; 20: 6960
12 Roberts BF, Zheng Y, Cleaveleand J, Lee S, Lee E, Ayong L, Yuan Y, Chakrabarti D. Int. J. Parasitol.: Drugs Drug Resist. 2017; 7: 120
13 Wang XQ, Xia CL, Chen SB, Tan JH, Ou TM, Huang SL, Li D, Gu LQ, Huang ZS. Eur. J. Med. Chem. 2015; 89: 349

14a Podeszwa B, Niedbala H, Polanski J, Musiol R, Tabak D, Finster J, Serafin K, Milczarek M, Wietrzyk J, Boryczka S, Mol W, Jampilek J, Dohnal J, Kalinowski DS, Richardson DR. Bioorg. Med. Chem. Lett. 2007; 17: 6138
14b Chang F.-S, Chen W, Wang C, Tzeng C.-C, Chen Y.-L. Bioorg. Med. Chem. 2010; 18: 124
14c Mrozek-Wilczkiewicz A, Spaczynska E, Malarz K, Cieslik W, Rams-Baron M, Krystof V, Musiol R. PLoS One 2015; 10: e0142678
14d El-Sayed MA.-A, El-Husseiny WM, Abdel-Aziz NI, El-Azab AS, Abuelizz HA, Abdel-Aziz AA.-M. J. Enzyme Inhib. Med. Chem. 2018; 33: 199

15a Gauthier JY, Jones T, Champion E, Charette L, DeHaven R, Ford-Hutchinson AW, Hoogsteen K, Lord A, Masson P, Piechuta H, Pong SS, Springer JP, Thérien M, Zamboni R, Young RN. J. Med. Chem. 1990; 33: 2841
15b Zamboni R, Belley M, Champion E, Charette L, DeHaven R, Frenette R, Gauthier JY, Jones TR, Leger S, Masson P, McFarlane CS, Metters K, Pong SS, Piechuta H, Rokach J, Thérien M, Williams HW. R, Young RN. J. Med. Chem. 1992; 35: 3832
15c Musiol R, Jampilek J, Buchta V, Silva L, Niedbala H, Podeszwa B, Palka A, Majerz-Maniecka K, Oleksyn B, Polanski J. Bioorg. Med. Chem. 2006; 14: 3592

16a Zeni G, Larock RC. Chem. Rev. 2006; 106: 4644
16b Dabiri M, Salehi P, Baghbanzadeh M, Nikcheh MS. Tetrahedron Lett. 2008; 49: 5366
16c Wu J, Cui X, Chen L, Jiang G, Wu Y. J. Am. Chem. Soc. 2009; 131: 13888
16d Cinar R, Nordmann J, Dirksen E, Müller TJ. J. Org. Biomol. Chem. 2013; 11: 2597
16e Gong L, Xing L.-J, Xu T, Zhu X.-P, Zhou W, Kang N, Wang B. Org. Biomol. Chem. 2014; 12: 6557
16f Jamal Z, Teo Y.-C. Synlett 2014; 25: 2049
16g Mao D, Hong G, Wu S, Liu X, Yu J, Wang L. Eur. J. Org. Chem. 2014; 3009
16h Kumar D, Kumar A, Qadri MM, Ansari MI, Gautam A, Chakraborti AK. RSC Adv. 2015; 5: 2920
16i Bering L, Antonchick AP. Org. Lett. 2015; 17: 3134
16j Jamal Z, Teo Y.-C, Lim GS. Tetrahedron 2016; 72: 2132
16k Xia H, Liu Y, Zhao P, Gou S, Wang J. Org. Lett. 2016; 18: 1796
16l Crisenza GE. M, Dauncey EM, Bower JF. Org. Biomol. Chem. 2016; 14: 5820
16m Zhang Z, Pi C, Tong H, Cui X, Wu Y. Org. Lett. 2017; 19: 440

17a Chen M.-Y, Hsu M.-A, Liu C.-Y, Chow TJ. J. Chin. Chem. Soc. 2004; 51: 735
17b Martirosyan AR, Rahim-Bata R, Freeman AB, Clarke CD, Howard RL, Strobl JS. Biochem. Pharmacol. 2004; 68: 1729
17c Gao W, Li Z, Xu Q, Li Y. RSC Adv. 2018; 8: 38844

18 Omar WA. E, Hormi OE. O. Tetrahedron 2009; 65: 4422
19 Phillips JP, Breese R, Barrall EM. J. Org. Chem. 1959; 24: 1104

20a Abonia R, Cuervo P, Insuasty B, Quiroga J, Nogueras M, Cobo J, Meier H, Lotero E. Open Org. Chem. J. 2008; 2: 26
20b Bhattacharya RN, Kundu P, Maiti G. Synth. Commun. 2010; 40: 476
20c Lad UP, Kulkarni MA, Desai UV, Wadgaonkar PP. C. R. Chim. 2011; 14: 1059
20d Rueping M, Moreth SA, Bolte M. Z. Naturforsch., B 2012; 67: 1021
20e Zheng X, Jiang H, Xie J, Yin Z, Zhang H. Synth. Commun. 2013; 43: 1023
20f Cheng S, Zhao L, Yu S. Adv. Synth. Catal. 2014; 356: 982

21 Satish G, Ashok P, Kota L, Ilangovan A. ChemistrySelect 2019; 4: 1346

22a Conrad M, Limpach L. Ber. Dtsch. Chem. Ges. 1891; 24: 2990
22b Cheng CC, Yan SJ. Org. React. (N. Y.) 1982; 28: 37
22c Marco-Contelles J, Pérez-Mayoral E, Samadi A, Carreiras MC, Soriano E. Chem. Rev. 2009; 109: 2652

23a Domínguez JN, Charris JE, Lobo G, Gamboa-Domínguez N, Moreno MM, Riggione F, Sánchez E, Olson J, Rosenthal PJ. Eur. J. Med. Chem. 2001; 36: 555
23b Charris JE, Domínguez JN, Gamboa N, Rodrigues JR, Angel JE. Eur. J. Med. Chem. 2005; 40: 875
23c Tseng CH, Chen YL, Hsu CY, Chen TC, Cheng CM, Tso HC, Lu YJ, Tzeng CC. Eur. J. Med. Chem. 2013; 59: 274
23d Rao NS, Shaik AB, Routhu SR, Hussaini SM. A, Sunkari S, Rao AV. S, Reddy AM, Alarifi A, Kamal A. ChemistrySelect 2017; 2: 2989

24a Paull KP, Shoemaker RH, Hodes L, Monks A, Scudiero DA, Rubinstein L, Plowman J, Boyd MR. J. Natl. Cancer Inst. 1989; 81: 1088
24b Monks A, Scudiero D, Skehan P, Shoemaker R, Paull K, Vistica D, Hose C, Jangley J, Cronisie P, Viagro-Wolff A, Gray-Goodrich M, Campell H, Boyd M. J. Natl. Cancer Inst. 1991; 83: 757
24c Grever MR, Schepartz SA, Chabner BA. Semin. Oncol. 1992; 19: 622
24d Boyd MR, Paull KD. Drug Dev. Res. 1995; 34: 91
24e Weinstein JN, Myers TG, O’Connor PM, Friend SH, Fornace AJ, Kohn KW. Jr, Fojo T, Bates SE, Rubinstein LV, Anderson NL, Buolamwini JK, van Osdol WW, Monks AP, Scudiero DA, Sausville EA, Zaharevitz DW, Bunow B, Viswanadhan VN, Johnson GS, Wittes RE, Paull KD. Science 1997; 275: 343
24f Acton EM, Narayanan VL, Risbood PA, Shoemaker RH, Vistica DT, Boyd MR. J. Med. Chem. 1994; 37: 2185

25 APEX3 v2018.1-0. Bruker AXS Inc; Madison, Wisconsin: 2018
26 SAINT V8.38A. Bruker AXS Inc; Madison, Wisconsin: 2016
27 Sheldrick GM. Acta Crystallogr., Sect. A 2015; 71: 3
28 Sheldrick GM, Usón I. Acta Crystallogr., Sect. D 2018; 74: 106
29 Dolomanov OV, Bourhis LJ, Gildea RJ, Howard JA. K, Puschmann H. J. Appl. Crystallogr. 2009; 42: 339

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