메뉴 건너뛰기




Volumn 17, Issue 6, 2012, Pages 7543-7555

Design, synthesis and antiviral potential of 14-aryl/heteroaryl-14H- dibenzo[a, j]xanthenes using an efficient polymer-supported catalyst

Author keywords

2 Naphthol; Aryl aldehydes; Neat reaction; PEG OSO 3H; Tobacco mosaic virus; Xanthenes

Indexed keywords

2 NAPHTHOL; 2-NAPHTHOL; ALDEHYDE; ANTIVIRUS AGENT; MACROGOL DERIVATIVE; NAPHTHOL DERIVATIVE; POLYMER; XANTHENE DERIVATIVE;

EID: 84863001177     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17067543     Document Type: Article
Times cited : (75)

References (37)
  • 1
    • 17044424644 scopus 로고    scopus 로고
    • Resistance to plant viruses: Old issue, new answer
    • Ritzenthaler, C. Resistance to plant viruses: Old issue, new answer. Curr. Opin. Biotechnol. 2005, 16, 118-122.
    • (2005) Curr. Opin. Biotechnol. , vol.16 , pp. 118-122
    • Ritzenthaler, C.1
  • 2
    • 0036385304 scopus 로고    scopus 로고
    • Condensation of aromatic aldehydes with 5, 5-dimethyl-1, 3-cyclohexanedione without catalyst
    • 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.
    • (2002) Synth. Commun. , vol.32 , pp. 3063-3067
    • Tu, S.J.1    Zhou, J.F.2    Lu, Z.S.3    Deng, X.4    Shi, D.Q.5    Wang, S.H.6
  • 3
    • 33845556450 scopus 로고
    • Immobilized transition-metal carbonyls and related Catalysts
    • Bailey, D. C.; Langer, S. H. Immobilized transition-metal carbonyls and related Catalysts. Chem. Rev. 1981, 81, 109-148.
    • (1981) Chem. Rev. , vol.81 , pp. 109-148
    • Bailey, D.C.1    Langer, S.H.2
  • 4
    • 7044263277 scopus 로고    scopus 로고
    • Synthesis and applications of small molecule libraries
    • Thompson, L. A.; Ellman, J. A. Synthesis and Applications of Small Molecule Libraries. Chem. Rev. 1996, 96, 555-600. (Pubitemid 126637733)
    • (1996) Chemical Reviews , vol.96 , Issue.1 , pp. 555-600
    • Thompson, L.A.1    Ellman, J.A.2
  • 5
    • 31744432111 scopus 로고    scopus 로고
    • 3H as catalyst for 3,4-dihydropyrimidones via Biginelli reaction under microwave and solvent-free conditions
    • DOI 10.1080/00397910500383519, PII RH466368L7M22442
    • 3H as Catalyst for 3, 4-Dihydropyrimidones via Biginelli Reaction Under Microwave and Solvent-Free Conditions. Synth. Commun. 2006, 36, 451-456. (Pubitemid 43175901)
    • (2006) Synthetic Communications , vol.36 , Issue.4 , pp. 451-456
    • Wang, X.1    Quan, Z.2    Wang, F.3    Wang, M.4    Zhang, Z.5    Li, Z.6
  • 6
    • 39549111678 scopus 로고    scopus 로고
    • 3H 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
    • 3H 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.
    • (2008) Catal. Commun. , vol.9 , pp. 1497-1500
    • Kiasat, A.1    Mehrjardi, M.F.2
  • 8
    • 79957718370 scopus 로고    scopus 로고
    • 3H 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
    • 3H 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.
    • (2011) J. Iran. Chem. Soc. , vol.8 , pp. 411-423
    • Hasaninejada, A.1    Shekouhya, M.2    Zareb, A.3    Hoseini Ghattalia, S.M.S.4    Golzara, N.5
  • 9
    • 27444446650 scopus 로고    scopus 로고
    • Efficient two-step synthesis of 9-aryl-6-hydroxy-3H-xanthen-3-one fluorophores
    • DOI 10.1021/jo051243i
    • 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. (Pubitemid 41532847)
    • (2005) Journal of Organic Chemistry , vol.70 , Issue.22 , pp. 9051-9053
    • Bacci, J.P.1    Kearney, A.M.2    Van Vranken, D.L.3
  • 10
    • 0024559378 scopus 로고
    • Xanthene-dye-labelled phosphatidylethanolamines as probes of interfacial pH: Studies in phospholipid vesicles
    • Knight, C. G.; Stephenes, T. Xanthene-dye-labelled phosphatidylethanolamines as probes of interfacial pH: Studies in phospholipid vesicles. J. Biochem. 1989, 258, 683-687.
    • (1989) J. Biochem. , vol.258 , pp. 683-687
    • Knight, C.G.1    Stephenes, T.2
  • 11
    • 0037463811 scopus 로고    scopus 로고
    • Exploring the potential of xanthene derivatives as trypanothione reductase inhibitors and chloroquine potentiating agents
    • DOI 10.1016/S0040-4020(03)00240-0
    • 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. (Pubitemid 36331903)
    • (2003) Tetrahedron , vol.59 , Issue.13 , pp. 2289-2296
    • Chibale, K.1    Visser, M.2    Van Schalkwyk, D.3    Smith, P.J.4    Saravanamuthu, A.5    Fairlamb, A.H.6
  • 12
    • 84859109802 scopus 로고
    • Chemical aspects of santalin as a histological stain
    • Banerjee, A.; Mukherjee, A. K. Chemical aspects of santalin as a histological stain. Stain Technol. 1981, 56, 83-85. (Pubitemid 11084561)
    • (1981) Stain Technology , vol.56 , Issue.2 , pp. 83-85
    • Banerjee, A.1    Mukherjee, A.K.2
  • 13
    • 33646502807 scopus 로고    scopus 로고
    • Dowex-promoted general synthesis of N, N'-disubstituted-4-aryl-3, 4-dihydropyrimidinones using a solvent-free Biginelli condensation protocol
    • 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.
    • (2006) Tetrahedron Lett. , vol.47 , pp. 4205-4207
    • Singh, K.1    Arora, D.2    Singh, S.3
  • 14
    • 33751080407 scopus 로고    scopus 로고
    • Heterogeneous catalyst: Amberlyst-15 catalyzes the synthesis of 14-substituted-14H-dibenzo[a,j]xanthenes under solvent-free conditions
    • DOI 10.1016/j.tetlet.2006.10.072, PII S0040403906020776
    • 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. (Pubitemid 44767856)
    • (2006) Tetrahedron Letters , vol.47 , Issue.50 , pp. 8827-8829
    • Ko, S.1    Yao, C.-F.2
  • 15
    • 3543109146 scopus 로고    scopus 로고
    • One step synthesis of dibenzoxanthenes
    • DOI 10.1016/j.dyepig.2004.03.010, PII S0143720804000555
    • Sarma, R. J.; Baruah, J. B. One step synthesis of dibenzoxanthenes. Dyes Pigments 2005, 64, 91-92. (Pubitemid 39033198)
    • (2005) Dyes and Pigments , vol.64 , Issue.1 , pp. 91-92
    • Sarma, R.J.1    Baruah, J.B.2
  • 16
    • 8644251516 scopus 로고
    • Action of formamide and formanilide on naphthols and on barbituric acid
    • Papini, P.; Cimmarusti, R. Action of formamide and formanilide on naphthols and on barbituric acid. Gazz. Chim. Ital. 1947, 77, 142.
    • (1947) Gazz. Chim. Ital. , vol.77 , pp. 142
    • Papini, P.1    Cimmarusti, R.2
  • 17
    • 2142661170 scopus 로고
    • The condensation of primary alcohols with resorcinol and other hydroxy aromatic compounds
    • 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.
    • (1925) J. Am. Chem. Soc. , vol.47 , pp. 1079-1091
    • Sen, R.N.1    Sarkar, N.2
  • 18
    • 8644274912 scopus 로고
    • An improved synthesis of dibenzoxanthene
    • Ota, K.; Kito, T. An improved synthesis of dibenzoxanthene. Bull. Chem. Soc. Jpn. 1976, 49, 1167-1168.
    • (1976) Bull. Chem. Soc. Jpn. , vol.49 , pp. 1167-1168
    • Ota, K.1    Kito, T.2
  • 19
    • 17144400729 scopus 로고    scopus 로고
    • A facile, simple and convenient method for the synthesis of 14-alkyl or aryl-14-H-dibenzo[a,j]xanthenes catalyzed by pTSA in solution and solvent-free conditions
    • DOI 10.1055/s-2005-864837, D38204ST
    • 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. (Pubitemid 40524265)
    • (2005) Synlett , Issue.6 , pp. 955-958
    • Khosropour, A.R.1    Khodaei, M.M.2    Moghannian, H.3
  • 20
    • 27744468959 scopus 로고    scopus 로고
    • Sulfamic acid: A novel and efficient catalyst for the synthesis of aryl-14H-dibenzo[a.j]xanthenes under conventional heating and microwave irradiation
    • DOI 10.1016/j.tetlet.2005.10.057, PII S0040403905022756
    • 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. (Pubitemid 41617355)
    • (2005) Tetrahedron Letters , vol.46 , Issue.50 , pp. 8691-8693
    • Rajitha, B.1    Sunil Kumar, B.2    Thirupathi Reddy, Y.3    Narsimha Reddy, P.4    Sreenivasulu, N.5
  • 21
    • 33746025668 scopus 로고    scopus 로고
    • Iodine catalyzed simple and efficient synthesis of 14-aryl or alkyl-14-H-dibenzo[a,j]xanthenes
    • DOI 10.1016/j.molcata.2006.04.007, PII S1381116906007412
    • 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. (Pubitemid 44067554)
    • (2006) Journal of Molecular Catalysis A: Chemical , vol.255 , Issue.1-2 , pp. 74-77
    • Das, B.1    Ravikanth, B.2    Ramu, R.3    Laxminarayana, K.4    Rao, B.V.5
  • 22
    • 33846240529 scopus 로고    scopus 로고
    • Molecular iodine catalyzed synthesis of aryl-14H-dibenzo[a, j]xanthenes under solvent-free condition
    • DOI 10.1016/j.bmcl.2006.11.009, PII S0960894X06012972
    • Pasha, M. A.; Jayashankara, V. P. Molecular iodine catalyzed synthesis of aryl-14Hdibenzo[a, j]xanthenes under solvent-free condition. Bioorg. Med. Chem. Lett. 2007, 17, 621-623. (Pubitemid 46108575)
    • (2007) Bioorganic and Medicinal Chemistry Letters , vol.17 , Issue.3 , pp. 621-623
    • Pasha, M.A.1    Jayashankara, V.P.2
  • 23
    • 34249329620 scopus 로고    scopus 로고
    • 2O): A mild and efficient reusable catalyst for the synthesis of aryl-14H-dibenzo[a.j]xanthenes under conventional heating and microwave irradiation
    • DOI 10.1016/j.catcom.2006.11.003, PII S1566736706004110
    • 2O): 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. (Pubitemid 46810360)
    • (2007) Catalysis Communications , vol.8 , Issue.8 , pp. 1173-1177
    • Nagarapu, L.1    Kantevari, S.2    Mahankhali, V.C.3    Apuri, S.4
  • 24
    • 34548314184 scopus 로고    scopus 로고
    • Wet cyanuric chloride catalyzed simple and efficient synthesis of 14-aryl or alkyl-14-H-dibenzo[a,j]xanthenes
    • DOI 10.1016/j.catcom.2007.01.007, PII S1566736707000179
    • 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. (Pubitemid 47432861)
    • (2007) Catalysis Communications , vol.8 , Issue.11 , pp. 1595-1598
    • Bigdeli, M.A.1    Heravi, M.M.2    Hossein Mahdavinia, G.3
  • 25
    • 33747074632 scopus 로고    scopus 로고
    • 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
    • DOI 10.1055/s-2006-947339
    • 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. (Pubitemid 44214825)
    • (2006) Synlett , Issue.12 , pp. 1928-1932
    • Saini, A.1    Kumar, S.2    Sandhu, J.S.3
  • 26
    • 34548361835 scopus 로고    scopus 로고
    • 2): A mild, reusable and highly efficient heterogeneous catalyst for the synthesis of 14-aryl or alkyl-14-H-dibenzo[a,j]xanthenes
    • DOI 10.1016/j.molcata.2007.05.007, PII S1381116907003251
    • 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. (Pubitemid 47337065)
    • (2007) Journal of Molecular Catalysis A: Chemical , vol.275 , Issue.1-2 , pp. 25-29
    • Bigdeli, M.A.1    Heravi, M.M.2    Mahdavinia, G.H.3
  • 27
    • 37649004405 scopus 로고    scopus 로고
    • Ecofriendly and efficient one-pot synthesis of alkyl-or aryl-14H-dibenzo[a, j]xanthenes in water
    • 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.
    • (2008) Bioorg. Med. Chem. Lett. , vol.18 , pp. 436-438
    • Dabiri, M.1    Baghbanzadeh, M.2    Nikcheh, M.S.3    Arzroomchilar, E.4
  • 28
    • 34548661513 scopus 로고    scopus 로고
    • Solvent-free synthesis of aryl-14H-dibenzo[a,j]xanthenes and 1,8-dioxo-octahydro-xanthenes using silica sulfuric acid as catalyst
    • DOI 10.1016/j.dyepig.2007.02.001, PII S0143720807000344
    • 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. (Pubitemid 47412973)
    • (2008) Dyes and Pigments , vol.76 , Issue.3 , pp. 836-839
    • Seyyedhamzeh, M.1    Mirzaei, P.2    Bazgir, A.3
  • 29
    • 42649087436 scopus 로고    scopus 로고
    • 3-catalyzed condensation reaction of β-naphthol and aldehyde in ionic liquids: A green synthesis of aryl-14H-dibenzo[a, j]xanthenes
    • 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.
    • (2008) Tetrahedron Lett. , vol.49 , pp. 3391-3394
    • Su, W.K.1    Yang, D.2    Jin, C.3    Zhang, B.4
  • 31
    • 79952180055 scopus 로고    scopus 로고
    • 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
    • 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.
    • (2011) Res. J. Pharm. Biol. Chem. Sci. , vol.2 , pp. 71-76
    • Nazeruddin, G.M.1    Abdulkarim, M.A.A.K.2
  • 32
    • 34447254761 scopus 로고    scopus 로고
    • Microwave-assisted synthesis of 14-aryl-14H-dibenzo[a, j]xanthenes catalysed by methanesulfonic acid under solvent-free conditions
    • 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.
    • (2007) Mendeleev Commun. , vol.17 , pp. 247-248
    • Bhattacharya, A.K.1    Rana, K.C.2
  • 34
    • 64549109038 scopus 로고    scopus 로고
    • Synthesis and antiviral activities of chiral thiourea derivatives containing an α-aminophosphonate moiety
    • 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.
    • (2009) J. Agric. Food Chem. , vol.57 , pp. 1383-1388
    • Chen, M.H.1    Chen, Z.2    Song, B.A.3    Bhadury, P.S.4    Yang, S.5    Cai, X.J.6    Hu, D.Y.7    Xue, W.8    Zeng, S.9
  • 35
    • 79953833571 scopus 로고    scopus 로고
    • 3H): An efficient, bio-degradable and reusable polymeric catalyst for the solvent-free synthesis of poly-substituted quinolines under microwave irradiation
    • 3H): 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.
    • (2011) Green Chem. , vol.13 , pp. 958-964
    • Hasaninejad, A.1    Zare, A.2    Shekouhy, M.3    Rad, J.A.4
  • 36
    • 0014152185 scopus 로고
    • A simple technique for purification of tobacco mosaic virus in large quantities
    • Gooding, G. V.; Hebert, T. T. A simple technique for purification of tobacco mosaic virus in large quantities. Phytopathology 1967, 57, 1285.
    • (1967) Phytopathology , vol.57 , pp. 1285
    • Gooding, G.V.1    Hebert, T.T.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.