Design, Synthesis and Antiviral Potential of 14-Aryl/Heteroaryl-14H-dibenzo[a,j]xanthenes Using an Efficient Polymer-Supported Catalyst
Abstract
:1. Introduction
2. Results and Discussion
2.1. Chemistry
2.2. Biology
3. Experimental
3.1. General
3.2. Catalyst Preparation
3.3. General Procedure for the Synthesis of 14-(4-Chloro-3-nitrophenyl)-14H-dibenxo[a,j]xanthenes 3a–i
3.4. Procedure for the Synthesis of 4-(14H-Dibenzo[a,j]xanthen-14-yl)piperazine-1-carbaldehyde (5)
3.5. Procedure for the Synthesis of 7-(1-(14H-dibenzo[a,j]xanthen-14-yl)piperidin-4-yl)-7H-dibenzo-[c,h]phenoxazine (6)
3.6. Procedure for the Synthesis of 9,9-Dimethyl-12-(pyridin-2-yl)-9,10-dihydro-8H-benzo[a]xanthen-11(12H)-one (9)
3.7. Antiviral Activity
3.7.1. Purification of Tobacco Mosaic Virus (TMV)
3.7.2. Curative Effect of Compounds against TMV in Vivo
4. Conclusions
Acknowledgments
References and Notes
- Ritzenthaler, C. Resistance to plant viruses: Old issue, new answer. Curr. Opin. Biotechnol. 2005, 16, 118–122. [Google Scholar] [CrossRef] [PubMed]
- Tu, S.J.; Zhou, J.F.; Lu, Z.S.; Deng, X.; Shi, D.Q.; Wang, S.H. Condensation of Aromatic Aldehydes with 5,5-dimethyl-1,3-cyclohexanedione without catalyst. Synth. Commun. 2002, 32, 3063–3067. [Google Scholar] [CrossRef]
- Bailey, D.C.; Langer, S.H. Immobilized transition-metal carbonyls and related Catalysts. Chem. Rev. 1981, 81, 109–148. [Google Scholar] [CrossRef]
- Thompson, L.A.; Ellman, J.A. Synthesis and Applications of Small Molecule Libraries. Chem. Rev. 1996, 96, 555–600. [Google Scholar] [CrossRef] [PubMed]
- Wang, X.; Quan, Z.; Wang, F.; Wang, M.; Zhang, Z.; Li, Z. PEG-SO3H as Catalyst for 3,4-Dihydropyrimidones via Biginelli Reaction Under Microwave and Solvent-Free Conditions. Synth. Commun. 2006, 36, 451–456. [Google Scholar] [CrossRef]
- Kiasat, A.; Mehrjardi, M.F. PEG-SO3H as eco-friendly polymeric catalyst for regioselective ring opening of epoxides using thiocyanate anion in water: An efficient route to synthesis of β-hydroxy thiocyanate. Catal.Commun. 2008, 9, 1497–1500. [Google Scholar] [CrossRef]
- Wang, X.C.; Li, L.; Quan, Z.J.; Gong, H.P.; Ye, H.L.; Cao, X.F. PEG-SO3H as catalyst for the Beckmann rearrangement and dehydration of oximes. Chin.Chem. Lett. 2009, 20, 651–655. [Google Scholar] [CrossRef]
- Hasaninejada, A.; Shekouhya, M.; Zareb, A.; Hoseini Ghattalia, S.M.S.; Golzara, N. PEG-SO3H as a New, Highly Efficient and Homogeneous Polymeric Catalyst for the Synthesis of Bis(indolyl)methanes and 4,4′-(Arylmethylene)-bis(3-methyl-1-phenyl-1H-pyrazol-5-ol)s in Water. J. Iran. Chem. Soc. 2011, 8, 411–423. [Google Scholar] [CrossRef]
- Bacci, J.P.; Kearney, A.M.; van Vranken, D.L. Efficient two-step synthesis of 9-aryl-6-hydroxy-3H-xanthen-3-one fluorophores. J. Org. Chem. 2005, 70, 9051–9053. [Google Scholar] [CrossRef] [PubMed]
- Knight, C.G.; Stephenes, T. Xanthene-dye-labelled phosphatidylethanolamines as probes of interfacial pH: Studies in phospholipid vesicles. J. Biochem. 1989, 258, 683–687. [Google Scholar] [CrossRef]
- Chibale, K.; Visser, M.R.; van Schalkwyk, D.; Smith, P.J.; Saravanamuthu, A.; Fairlamb, A.H. Exploring the potential of xanthene derivatives as trypanothione reductase inhibitors and chloroquine potentiating agents. Tetrahedron 2003, 59, 2289–2296. [Google Scholar] [CrossRef]
- Banerjee, A.; Mukherjee, A.K. Chemical aspects of santalin as a histological stain. Stain Technol. 1981, 56, 83–85. [Google Scholar] [CrossRef] [PubMed]
- Singh, K.; Arora, D.; Singh, S. Dowex-promoted general synthesis of N,N′-disubstituted-4-aryl-3,4-dihydropyrimidinones using a solvent-free Biginelli condensation protocol. Tetrahedron Lett. 2006, 47, 4205–4207. [Google Scholar] [CrossRef]
- Ko, S.; Yao, C.-F. Heterogeneous catalyst: Amberlyst-15 catalyzes the synthesis of 14-substituted-14H-dibenzo[a,j]xanthenes under solvent-free conditions. Tetrahedron Lett. 2006, 47, 8827–8829. [Google Scholar] [CrossRef]
- Sarma, R.J.; Baruah, J.B. One step synthesis of dibenzoxanthenes. Dyes Pigments 2005, 64, 91–92. [Google Scholar] [CrossRef]
- Papini, P.; Cimmarusti, R. Action of formamide and formanilide on naphthols and on barbituric acid. Gazz. Chim. Ital. 1947, 77, 142. [Google Scholar]
- Sen, R.N.; Sarkar, N. The condensation of primary alcohols with resorcinol and other hydroxy aromatic compounds. J. Am. Chem. Soc. 1925, 47, 1079–1091. [Google Scholar] [CrossRef]
- Ota, K.; Kito, T. An improved synthesis of dibenzoxanthene. Bull. Chem. Soc. Jpn. 1976, 49, 1167–1168. [Google Scholar] [CrossRef]
- Khosropour, A.R.; Khodaei, M.M.; Moghannian, H. A facile, simple, and convenient method for the synthesis of 14-alkyl or aryl-14H-dibenzo[a,j]xanthenes catalyzed by p-TSA in solution and solvent free conditions. Synlett 2005, 2005, 955–958. [Google Scholar] [CrossRef]
- Rajitha, B.; Kumar, B.S.; Reddy, Y.T.; Reddy, P.; Sreenivasulu, N. Sulfamic acid: A novel and efficient catalyst for the synthesis of aryl-14H-dibenzo[a,j]xanthenes under conventional heating and microwave irradiation. Tetrahedron Lett. 2005, 46, 8691–8693. [Google Scholar] [CrossRef]
- Das, B.; Ravikanth, B.; Ramu, R.; Laxminarayana, K.; Rao, B.V. Iodine-catalyzed simple and efficient synthesis of 14-aryl or alkyl-14H-dibenzo[a,j]xanthenes. J. Mol. Catal. A Chem. 2006, 255, 74–77. [Google Scholar] [CrossRef]
- Pasha, M.A.; Jayashankara, V.P. Molecular iodine catalyzed synthesis of aryl-14H-dibenzo[a,j]xanthenes under solvent-free condition. Bioorg. Med.Chem. Lett. 2007, 17, 621–623. [Google Scholar] [CrossRef] [PubMed]
- Nagarapu, L.; Kantevari, S.; Mahankhali, V.C.; Apuri, S. Potassium dodecatungstocobaltate trihydrate (K5CoW12O40·3H2O): A mild and efficient reusable catalyst for the synthesis of aryl-14H-dibenzo[a.j]xanthenes under conventional heating and microwave irradiation. Catal. Commun. 2007, 8, 1173–1177. [Google Scholar] [CrossRef]
- Bigdeli, M.A.; Heravi, M.M.; Mahdavinia, G.H. Wet cyanuric chloride catalyzed simple and efficient synthesis of 14-aryl or alkyl-14H-dibenzo[a,j]xanthenes. Catal. Commun. 2007, 8, 1595–1598. [Google Scholar] [CrossRef]
- Saini, A.; Kumar, S.; Sandhu, J.S. A New LiBr-Catalyzed, Facile and Efficient Method for the Synthesis of 14-Alkyl or Aryl-14H-dibenzo[a,j]xanthenes and Tetrahydrobenzo[b]pyrans under Solvent-Free Conventional and Microwave Heating. Synlett 2006, 2006, 1928–1932. [Google Scholar] [CrossRef]
- Bigdeli, M.A.; Heravi, M.M.; Mahdavinia, G.H. Silica-supported perchloric acid (HClO4-SiO2): A mild, reusable, and highly efficient heterogeneous catalyst for the synthesis of 14-aryl or alkyl-14H-dibenzo[a,j]xanthenes. J. Mol. Catal. A Chem. 2007, 275, 25–29. [Google Scholar] [CrossRef]
- Dabiri, M.; Baghbanzadeh, M.; Nikcheh, M.S.; Arzroomchilar, E. Ecofriendly and efficient one-pot synthesis of alkyl-or aryl-14H-dibenzo[a,j]xanthenes in water. Bioorg. Med. Chem. Lett. 2008, 18, 436–438. [Google Scholar] [CrossRef] [PubMed]
- Seyyedhamzeh, M.; Mirzaei, P.; Bazgir, A. Solvent-free synthesis of aryl-14H-dibenzo[a,j]xanthenes and 1,8-dioxo-octahydroxanthenes using silica sulfuric acid as catalyst. Dyes Pigments 2008, 76, 836–839. [Google Scholar] [CrossRef]
- Su, W.K.; Yang, D.; Jin, C.; Zhang, B. Yb(OTf)3-catalyzed condensation reaction of β-naphthol and aldehyde in ionic liquids: A green synthesis of aryl-14H-dibenzo[a,j]xanthenes. Tetrahedron Lett. 2008, 49, 3391–3394. [Google Scholar] [CrossRef]
- Fu, G.Y.; Huang, Y.X.; Chen, X.G.; Liu, X.L. An Efficient Synthesis of 14-Aryl or Alkyl-14H-dibenzo[a,j]xanthenes Using Reusable HBF4-SiO2 Catalyst Under Thermal and Solvent-Free Conditions. J. Chin. Chem. Soc. 2009, 56, 381–385. [Google Scholar] [CrossRef]
- Nazeruddin, G.M.; Abdulkarim, M.A.A.K. Ultrasound assisted one-pot synthesis of 12-aryl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one derivatives using chlorosulphonic acid as a catalyst under solvent-free conditions. Res. J. Pharm. Biol. Chem. Sci. 2011, 2, 71–76. [Google Scholar]
- Bhattacharya, A.K.; Rana, K.C. Microwave-assisted synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes catalysed by methanesulfonic acid under solvent-free conditions. Mendeleev Commun. 2007, 17, 247–248. [Google Scholar] [CrossRef]
- Hu, D.Y.; Wang, Q.Q.; Yang, S.; Song, B.A.; Bhadury, P.S.; Jin, L.H.; Yan, K.; Liu, F.; Chen, Z.; Xue, W. Synthesis and antiviral activities of amide derivatives containing the α-aminophosphonate moiety. J. Agric. Food Chem. 2008, 56, 998–1001. [Google Scholar] [CrossRef] [PubMed]
- Chen, M.H.; Chen, Z.; Song, B.A.; Bhadury, P.S.; Yang, S.; Cai, X.J.; Hu, D.Y.; Xue, W.; Zeng, S. Synthesis and antiviral activities of chiral thiourea derivatives containing an α-aminophosphonate moiety. J. Agric. Food Chem. 2009, 57, 1383–1388. [Google Scholar] [CrossRef] [PubMed]
- Hasaninejad, A.; Zare, A.; Shekouhy, M.; Rad, J.A. Sulfuric acid-modified PEG-6000 (PEG–OSO3H): An efficient, bio-degradable and reusable polymeric catalyst for the solvent-free synthesis of poly-substituted quinolines under microwave irradiation. Green Chem. 2011, 13, 958–964. [Google Scholar] [CrossRef]
- Gooding, G.V.; Hebert, T.T. A simple technique for purification of tobacco mosaic virus in large quantities. Phytopathology 1967, 57, 1285. [Google Scholar] [PubMed]
- Li, S.Z.; Wang, D.M.; Jiao, S.M. Pesticide Experiment Methods-Fungicide Sector; Press of China: Beijing, China, 1991; pp. 93–94. [Google Scholar]
Sample Availability: Samples of thecompounds 3a–3i, 5, 6 and 9 are available from the authors. |
Entry | Product | R | Time (min) | Yield (%) a | Melting Point (°C) | |
---|---|---|---|---|---|---|
Found | Literature [Ref.] | |||||
1 | 3a | 20 | 96 | 181–182 | 182–183 [30] | |
2 | 3b | 15 | 92 | 310–312 | 311–313 [30] | |
3 | 3c | 22 | 96 | 290–291 | 292–293 [30] | |
4 | 3d | 18 | 91 | 203–205 | 204–205 [30] | |
5 | 3e | 24 | 95 | 163–164 | 163–165 [31] | |
6 | 3f | 21 | 90 | 286–287 | 287–288 [30] | |
7 | 3g | 25 | 93 | 173–174 | 172–173 [30] | |
8 | 3h | 30 | 85 | 206–207 | 208–210 [32] | |
9 | 3i | 20 | 97 | 178–179 | - | |
10 | 5 | 25 | 90 | 183–184 | - | |
11 | 6 | 30 | 94 | 185–187 | - | |
12 | 9 | 32 | 92 | 179–181 | - |
Entry | Recovery | Time/min | Yields a (%) |
---|---|---|---|
1 | 0 | 20 | 96 |
2 | 1 | 20 | 95 |
3 | 2 | 20 | 93 |
4 | 3 | 20 | 92 |
© 2012 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
Share and Cite
Reddi Mohan Naidu, K.; Satheesh Krishna, B.; Anil Kumar, M.; Arulselvan, P.; Ibrahim Khalivulla, S.; Lasekan, O. Design, Synthesis and Antiviral Potential of 14-Aryl/Heteroaryl-14H-dibenzo[a,j]xanthenes Using an Efficient Polymer-Supported Catalyst. Molecules 2012, 17, 7543-7555. https://doi.org/10.3390/molecules17067543
Reddi Mohan Naidu K, Satheesh Krishna B, Anil Kumar M, Arulselvan P, Ibrahim Khalivulla S, Lasekan O. Design, Synthesis and Antiviral Potential of 14-Aryl/Heteroaryl-14H-dibenzo[a,j]xanthenes Using an Efficient Polymer-Supported Catalyst. Molecules. 2012; 17(6):7543-7555. https://doi.org/10.3390/molecules17067543
Chicago/Turabian StyleReddi Mohan Naidu, Kalla, Balam Satheesh Krishna, Mungara Anil Kumar, Palanisamy Arulselvan, Shaik Ibrahim Khalivulla, and Ola Lasekan. 2012. "Design, Synthesis and Antiviral Potential of 14-Aryl/Heteroaryl-14H-dibenzo[a,j]xanthenes Using an Efficient Polymer-Supported Catalyst" Molecules 17, no. 6: 7543-7555. https://doi.org/10.3390/molecules17067543