Synthesis of Novel Hybrid 4H-Pyran-lipoic and 4H-Pyran-azetidine Derivatives

Abstract

In this study, a molecular hybridization strategy was used to design and synthesize two novel series of hybrid compounds: 4H-pyran-lipoic and 4H-pyran-azetidine, employing ammonium hydroxide and involving the participation of aldehydes, malononitrile, and compounds derived from β-ketoesters to obtain the products with good yields.

Key words

molecular hybridization - multicomponent reaction - 4H-pyran-lipoic - 4H-pyran-azetidine core

• References

• 1 Viegas-Junior C. Danuello A. da Silva Bolzani V. Barreiro EJ. Fraga CA. M. Curr. Med. Chem. 2007; 14: 1829
• 2 Chen W. Zhan P. Rai D. De Clercq E. Pannecouque C. Balzarini J. Zhou Z. Liu H. Liu X. Bioorg. Med. Chem. 2014; 22: 1863
• 3 Song W.-J. Yang X.-D. Zeng X.-H. Xu X.-L. Zhang G.-L. Zhang H.-B. RSC Adv. 2012; 2: 4612
• 4 Fershtat LL. Makhova NN. ChemMedChem 2017; 12: 622
• 5 Liu X.-L. Feng T.-T. Jiang W.-D. Yang C. Tian M.-Y. Jiang Y. Lin B. Zhao Z. Zhou Y. Tetrahedron Lett. 2016; 57: 4411
• 6 Taha M. Ismail NH. Ali M. Rashid U. Imran S. Uddin N. Khan KM. Bioorg. Chem. 2017; 71: 192
• 7 Rosini M. Andrisano V. Bartolini M. Bolognesi ML. Hrelia P. Minarini A. Tarozzi A. Melchiorre C. J. Med. Chem. 2005; 48: 360
• 8 Koufaki M. Detsi A. Theodorou E. Kiziridi C. Calogeropoulou T. Vassilopoulos A. Kourounakis AP. Rekka E. Kourounakis PN. Gaitanaki C. Papazafiri P. Bioorg. Med. Chem. 2004; 12: 4835
• 9 Sozio P. D’Aurizio E. Iannitelli A. Cataldi A. Zara S. Cantalamessa F. Nasuti C. Di Stefano A. Arch. Pharm. (Weinheim) 2010; 343: 133
• 10 Woo YJ. Lee BH. Yeun GH. Kim HJ. Ko JM. Won M. Bull. Korean Chem. Soc. 2011; 32: 2997
• 11 López FI. de la Cruz FN. López J. Martínez JM. Alcaraz Y. Delgado F. Sánchez-Recillas A. Estrada-Soto S. Vázquez MA. Med. Chem. Res. 2017; 26: 1325
• 12 Barnes DM. Christesen AC. Engstrom KM. Haight AR. Hsu MC. Lee EC. Peterson MJ. Plata DJ. Raje PS. Stoner EJ. Tedrow JS. Wagaw S. Org. Process Res. Dev. 2006; 10: 803
• 13 Oizumi K. Nishino H. Koike H. Sada T. Miyamoto M. Kimura T. Jpn. J. Pharmacol. 1989; 51: 57
• 14 Kumar D. Reddy VB. Sharad S. Dube U. Kapur S. Eur. J. Med. Chem. 2009; 44: 3805
• 15 Mar’yasov MA. Sheverdov VP. Davydova VV. Nasakin OE. Pharm. Chem. J. 2017; 50: 798
• 16 Mar’yasov MA. Davydova VV. Sheverdov VP. Nasakin OE. Gein VL. Pharm. Chem. J. 2016; 50: 519
• 17 Khodairy A. Ali AM. Aboelez MO. El-Wassimy MT. J. Heterocycl. Chem. 2017; 54: 1442
• 18 Rendón-Vallejo P. Estrada-Soto S. Vázquez MA. Hernández-Borja F. Villalobos-Molina R. Ibarra-Barajas M. Lett. Drug Des. Discovery 2016; 13: 353
• 19 Hernández F. Sánchez A. Rendón-Vallejo P. Millán-Pacheco C. Alcaraz Y. Delgado F. Vázquez MA. Estrada-Soto S. Eur. J. Med. Chem. 2013; 70: 669
• 20 Alemán-Pantitlán S. Millán-Pacheco C. Vázquez MA. Hernández-Borja F. Villalobos-Molina R. Bazán-Perkins B. Est S. J. Appl. Pharm. Sci. 2016; 6: 29
• 21 Antoszczak M. Popiel K. Stefańska J. Wietrzyk J. Maj E. Janczak J. Michalska G. Brzezinski B. Huczyński A. Eur. J. Med. Chem. 2014; 76: 435
• 22 Fiuza SM. Gomes C. Teixeira LJ. Girão da Cruz MT. Cordeiro MN. D. S. Milhazes N. Borges F. Marques MP. M. Bioorg. Med. Chem. 2004; 12: 3581
• 23 Jordan CG. M. J. Pharm. Sci. 2017; 87: 880
• 24 Sánchez A. Hernández F. Cruz PC. Alcaraz Y. Tamariz J. Delgado F. Vázquez MA. J. Mex. Chem. Soc. 2012; 56: 121
• 25 Jiang B. Yi M.-S. Shi F. Tu S.-J. Pindi S. McDowell P. Li G. Chem. Commun. 2012; 808
• 26 Yao C. Wang Y. Li T. Yu C. Li L. Wang C. Tetrahedron 2013; 69: 10593
• 27 Ameta KL. Dandia A. Multicomponent Reactions (Synthesis of Bioactive Heterocycles) . 1st ed. CRC Press - Taylor & Francis Group; Baco Raton, FL: 2017
• 28 Algar WR. Krull UJ. Langmuir 2008; 24: 5514
• 29 Reddy VV. R. M. K. Babu KK. Ganesh A. Srinivasulu P. Madhusudhan G. Mukkanti K. Org. Process Res. Dev. 2010; 14: 931
• 30 Chavan SP. Kale RR. Shivasankar K. Chandake SI. Benjamin SB. Synthesis 2003; 2695