메뉴 건너뛰기




Volumn 12, Issue 3, 2007, Pages 543-551

Microwave-promoted facile and efficient preparation of N- (alkoxycarbonylmethyl) nucleobases - Building blocks for peptide nucleic acids

Author keywords

Microwave irradiation; Modified nucleoside analogues; Peptide nucleic acids

Indexed keywords

CYTOSINE; DRUG DERIVATIVE; N,N DIMETHYLFORMAMIDE; PEPTIDE NUCLEIC ACID; PURINE DERIVATIVE; THYMINE; URACIL;

EID: 34147127364     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/12030543     Document Type: Article
Times cited : (12)

References (34)
  • 1
    • 0023248316 scopus 로고
    • Synthesis and biological activity of unsaturated carboacyclic purine nucleoside analogs
    • Haines, D. R.; Tseng, C. K. H.; Marquez, V. E. Synthesis and biological activity of unsaturated carboacyclic purine nucleoside analogs. J. Med. Chem. 1987, 30, 943-947.
    • (1987) J. Med. Chem , vol.30 , pp. 943-947
    • Haines, D.R.1    Tseng, C.K.H.2    Marquez, V.E.3
  • 2
    • 0029052190 scopus 로고
    • Regioselective Coupling of Tetraalkylammonium Salts of 6-Iodo-2-aminopurine to a Cyclobutyl Triflate: Efficient Preparation of Homochiral BMS-180,194, a Potent Antiviral Carbocyclic Nucleoside
    • Bisacchi, G. S.; Singh, J.; Godfrey, J. D. Jr.; Kissick, T. P.; Mitt, T.; Malley, M. F.; Di Marco, J. D.; Gougoutas, J. Z.; Mueller, R. H.; Zahler, R. Regioselective Coupling of Tetraalkylammonium Salts of 6-Iodo-2-aminopurine to a Cyclobutyl Triflate: Efficient Preparation of Homochiral BMS-180,194, a Potent Antiviral Carbocyclic Nucleoside. J. Org. Chem. 1995, 60, 2902-2905.
    • (1995) J. Org. Chem , vol.60 , pp. 2902-2905
    • Bisacchi, G.S.1    Singh, J.2    Godfrey Jr., J.D.3    Kissick, T.P.4    Mitt, T.5    Malley, M.F.6    Di Marco, J.D.7    Gougoutas, J.Z.8    Mueller, R.H.9    Zahler, R.10
  • 3
    • 1842638305 scopus 로고    scopus 로고
    • Sensible Improvements Induced by Ionic Liquids in the Reaction of Modified Carbasugars with Bases for the Building of Constrained Carbanucleosides
    • Paoli, M.L.; Piccini, S.; Rodriquez, M.; Sega, A. Sensible Improvements Induced by Ionic Liquids in the Reaction of Modified Carbasugars with Bases for the Building of Constrained Carbanucleosides. J. Org. Chem. 2004, 69, 2881-2883.
    • (2004) J. Org. Chem , vol.69 , pp. 2881-2883
    • Paoli, M.L.1    Piccini, S.2    Rodriquez, M.3    Sega, A.4
  • 5
    • 18244402648 scopus 로고    scopus 로고
    • Microwave-Assisted Amination of a Chloropurine Derivative in the Synthesis of Acyclic Nucleoside Analogues
    • Lanver, A.; Schmalz, H.-G. Microwave-Assisted Amination of a Chloropurine Derivative in the Synthesis of Acyclic Nucleoside Analogues. Molecules 2005, 10, 508-515.
    • (2005) Molecules , vol.10 , pp. 508-515
    • Lanver, A.1    Schmalz, H.-G.2
  • 6
    • 0001707601 scopus 로고
    • 3′-Azido-3′- deoxythymidine (BW A509U): An antiviral agent that inhibits the infectivity and cytopathic effect of human T-lymphotropic virus type III/lymphadenopathy- associated virus in vitro
    • Mitsuya, H.; Weinhold, K.J.; Furman, P.A. 3′-Azido-3′- deoxythymidine (BW A509U): An antiviral agent that inhibits the infectivity and cytopathic effect of human T-lymphotropic virus type III/lymphadenopathy- associated virus in vitro. Pro. Natl. Acad. Sci. USA. 1985, 82, 7096-7100.
    • (1985) Pro. Natl. Acad. Sci. USA , vol.82 , pp. 7096-7100
    • Mitsuya, H.1    Weinhold, K.J.2    Furman, P.A.3
  • 7
    • 0026747732 scopus 로고
    • Synthesis and antiviral activity of acyclic nucleosides with a 3(S),5-dihydroxypentyl or 4(R)-methoxy-3 (S),5- dihydroxypentyl side chain
    • Vandenriessche, F.; Snoeck, R.; Janssen, G.; Hoogmartens, J.; Aerschot, A. V.; De Clercq, E.; Herdewijn, P. Synthesis and antiviral activity of acyclic nucleosides with a 3(S),5-dihydroxypentyl or 4(R)-methoxy-3 (S),5- dihydroxypentyl side chain. J. Med. Chem. 1992, 35, 1458-1465.
    • (1992) J. Med. Chem , vol.35 , pp. 1458-1465
    • Vandenriessche, F.1    Snoeck, R.2    Janssen, G.3    Hoogmartens, J.4    Aerschot, A.V.5    De Clercq, E.6    Herdewijn, P.7
  • 8
    • 0017811137 scopus 로고
    • 9-(2-Hydroxyethoxymethyl) guanine activity against viruses of the herpes group
    • Schaeffer, H.J.; Beauchamp, L.; De Miranda, P. 9-(2-Hydroxyethoxymethyl) guanine activity against viruses of the herpes group. Nature 1978, 272, 583-585.
    • (1978) Nature , vol.272 , pp. 583-585
    • Schaeffer, H.J.1    Beauchamp, L.2    De Miranda, P.3
  • 9
    • 0035977244 scopus 로고    scopus 로고
    • Total Synthesis of (-)-Neplanocin A by Using Lithium Thiolate-Initiated Michael-Aldol Tandem Cyclization Reaction
    • Ono, M.; Nishimura, K.; Tsubouchi, H.; Nagaoka, Y.; Tomioka, K. Total Synthesis of (-)-Neplanocin A by Using Lithium Thiolate-Initiated Michael-Aldol Tandem Cyclization Reaction. J. Org. Chem. 2001, 66, 8199-8203.
    • (2001) J. Org. Chem , vol.66 , pp. 8199-8203
    • Ono, M.1    Nishimura, K.2    Tsubouchi, H.3    Nagaoka, Y.4    Tomioka, K.5
  • 10
    • 0026341239 scopus 로고
    • Sequence-selective recognition of DNA by strand displacement with thymine-substituted polyamide
    • Nielsen, P.E.; Egholm, M.; Berg, R.H.; Buchardt, O. Sequence-selective recognition of DNA by strand displacement with thymine-substituted polyamide. Science 1991, 254, 1497-1500.
    • (1991) Science , vol.254 , pp. 1497-1500
    • Nielsen, P.E.1    Egholm, M.2    Berg, R.H.3    Buchardt, O.4
  • 12
    • 0032766821 scopus 로고    scopus 로고
    • Peptide Nucleic Acid. A Molecule with Two Identities
    • Nielsen, P. E. Peptide Nucleic Acid. A Molecule with Two Identities. Acc. Chem. Res. 1999, 32, 624-630.
    • (1999) Acc. Chem. Res , vol.32 , pp. 624-630
    • Nielsen, P.E.1
  • 13
    • 15944379583 scopus 로고    scopus 로고
    • Microwave assisted solid-phase synthesis of trisubstituted 2-(2,6-purin-9-yl) acetamides
    • Austin, R. E.; Waldraff, C.; Al-Obeidi, F. Microwave assisted solid-phase synthesis of trisubstituted 2-(2,6-purin-9-yl) acetamides. Tetrahedron Lett. 2005, 46, 2873-2875.
    • (2005) Tetrahedron Lett , vol.46 , pp. 2873-2875
    • Austin, R.E.1    Waldraff, C.2    Al-Obeidi, F.3
  • 16
    • 84990238662 scopus 로고
    • Peptide nucleic acids (PNA). Oligonucleotide analogs with an achiral peptide backbone
    • Egholm, M.; Buchardt, O.; Nielsen, P.E.; Berg, R.H. Peptide nucleic acids (PNA). Oligonucleotide analogs with an achiral peptide backbone. J. Am. Chem. Soc. 1992, 114, 1895-1897.
    • (1992) J. Am. Chem. Soc , vol.114 , pp. 1895-1897
    • Egholm, M.1    Buchardt, O.2    Nielsen, P.E.3    Berg, R.H.4
  • 17
    • 0028866843 scopus 로고
    • The synthesis of polyamide nucleic acids using a novel monomethoxytrityl protecting-group strategy
    • Will, D.W.; Breipohl, G.; Langner, D.; Knolle, J.; Uhlmann, E. The synthesis of polyamide nucleic acids using a novel monomethoxytrityl protecting-group strategy. Tetrahedron 1995, 51, 12069-12082.
    • (1995) Tetrahedron , vol.51 , pp. 12069-12082
    • Will, D.W.1    Breipohl, G.2    Langner, D.3    Knolle, J.4    Uhlmann, E.5
  • 18
    • 19744380074 scopus 로고    scopus 로고
    • Microwave assisted synthesis of N-(ethoxycarbonylmethyl) nucleobases: Building blocks for PNAs
    • Qu, G.-R.; Li, Y.; Han, S.-H. Microwave assisted synthesis of N-(ethoxycarbonylmethyl) nucleobases: Building blocks for PNAs. J. Chem. Res. 2005, 167-168.
    • (2005) J. Chem. Res , pp. 167-168
    • Qu, G.-R.1    Li, Y.2    Han, S.-H.3
  • 19
    • 33749557154 scopus 로고    scopus 로고
    • Microwave assisted synthesis of 6-substituted aminopurine analogs in water
    • Qu, G.-R.; Han, S.-H; Zhang, Z.; Geng, M.; Xue, F. Microwave assisted synthesis of 6-substituted aminopurine analogs in water. J. Braz. Chem. Soc. 2006, 17, 915-922.
    • (2006) J. Braz. Chem. Soc , vol.17 , pp. 915-922
    • Qu, G.-R.1    Han, S.-H.2    Zhang, Z.3    Geng, M.4    Xue, F.5
  • 20
    • 33747066349 scopus 로고    scopus 로고
    • Microwave-assisted regioselective synthesis of acyclic nucleosides through an alkylating reaction with 2-oxa-1,4-butanediol diacetate
    • Qu, G.-R.; Han, S.-H; Zhang, Z.; Geng, M.; Xue, F. Microwave-assisted regioselective synthesis of acyclic nucleosides through an alkylating reaction with 2-oxa-1,4-butanediol diacetate. Can. J. Chem. 2006, 84, 819-824.
    • (2006) Can. J. Chem , vol.84 , pp. 819-824
    • Qu, G.-R.1    Han, S.-H.2    Zhang, Z.3    Geng, M.4    Xue, F.5
  • 21
    • 11144325118 scopus 로고    scopus 로고
    • Controlled microwave heating in modern organic synthesis
    • Kappe, C.O. Controlled microwave heating in modern organic synthesis. Angew. Chem., Int. Ed. 2004, 43, 6250-6284.
    • (2004) Angew. Chem., Int. Ed , vol.43 , pp. 6250-6284
    • Kappe, C.O.1
  • 23
    • 33750461647 scopus 로고    scopus 로고
    • A Handy and Solventless Direct Route to Primary 3-[3-Aryl)-1,2,4-oxadiazol-5-yl]propionamides Using Microwave Irradiation
    • Ricardo, A.W.; Neves, F.; Rajendra, M.S. A Handy and Solventless Direct Route to Primary 3-[3-Aryl)-1,2,4-oxadiazol-5-yl]propionamides Using Microwave Irradiation. Molecules 2006, 11, 318-324.
    • (2006) Molecules , vol.11 , pp. 318-324
    • Ricardo, A.W.1    Neves, F.2    Rajendra, M.S.3
  • 24
    • 0033444261 scopus 로고    scopus 로고
    • Solvent-free organic syntheses: Using supported reagents and microwave irradiation
    • Varma, R.S. Solvent-free organic syntheses: Using supported reagents and microwave irradiation. Green Chem. 1999, 1, 43-55.
    • (1999) Green Chem , vol.1 , pp. 43-55
    • Varma, R.S.1
  • 25
    • 33646403467 scopus 로고    scopus 로고
    • Microwave Assisted Synthesis of N-Arylheterocyclic Substituted-4-aminoquinazoline Derivatives
    • Liu, G.; Yang, S.; Song, B.; Xue, W.; Hu, D.; Jin, L.; Lu, P. Microwave Assisted Synthesis of N-Arylheterocyclic Substituted-4-aminoquinazoline Derivatives. Molecules 2006, 11, 272-278.
    • (2006) Molecules , vol.11 , pp. 272-278
    • Liu, G.1    Yang, S.2    Song, B.3    Xue, W.4    Hu, D.5    Jin, L.6    Lu, P.7
  • 27
    • 33750703251 scopus 로고    scopus 로고
    • Rapid Microwave-assisted Fluorination Yielding novel 5′-deoxy-5′-Fluorouridine Derivatives
    • Le, H.P.; Muller, C.E. Rapid Microwave-assisted Fluorination Yielding novel 5′-deoxy-5′-Fluorouridine Derivatives. Bioorg. Med. Chem. Lett. 2006, 16, 6139-6142.
    • (2006) Bioorg. Med. Chem. Lett , vol.16 , pp. 6139-6142
    • Le, H.P.1    Muller, C.E.2
  • 28
    • 0038356872 scopus 로고    scopus 로고
    • Microwave-Assisted C-5 Iodination of Substituted Pyrimidinones and Pyrimidine Nucleosides
    • Paolini, L.; Petricci, E.; Corelli, F.; Botta, M. Microwave-Assisted C-5 Iodination of Substituted Pyrimidinones and Pyrimidine Nucleosides. Synthesis 2003, 1039-1042.
    • (2003) Synthesis , pp. 1039-1042
    • Paolini, L.1    Petricci, E.2    Corelli, F.3    Botta, M.4
  • 29
    • 14644435161 scopus 로고    scopus 로고
    • Microwave-Assisted Michael Addition of Some Pyrimidine and Purine Nucleobases with α, β-Unsaturated Esters: A Rapid Entry into Carboacyclic Nucleoside Synthesis
    • Khalafi-Nezhad, A.; Zarea, A.; Soltani Rad, M.N.; Mokhtari, B.; Parhami, A. Microwave-Assisted Michael Addition of Some Pyrimidine and Purine Nucleobases with α, β-Unsaturated Esters: A Rapid Entry into Carboacyclic Nucleoside Synthesis. Synthesis 2005, 419-424.
    • (2005) Synthesis , pp. 419-424
    • Khalafi-Nezhad, A.1    Zarea, A.2    Soltani Rad, M.N.3    Mokhtari, B.4    Parhami, A.5
  • 30
    • 1542709743 scopus 로고    scopus 로고
    • An electron-impact mass spectral (EIMS) study of N-1 and C-6 carboxyalkyl- and alkoxycarbonylalkyl-substituted derivatives of uracil
    • Wyrzykiewicz, E.; Kazimierczuk, Z. An electron-impact mass spectral (EIMS) study of N-1 and C-6 carboxyalkyl- and alkoxycarbonylalkyl-substituted derivatives of uracil. J. Heterocycl. Chem. 1998, 35, 349-358.
    • (1998) J. Heterocycl. Chem , vol.35 , pp. 349-358
    • Wyrzykiewicz, E.1    Kazimierczuk, Z.2
  • 31
    • 0032084927 scopus 로고    scopus 로고
    • Solid-phase Synthesis of Peptide Nucleic Acid (PNA) Monomers and Their Oligomerization Using Disulphide Anchoring Linkers
    • Aldrian-Herrada, G.; Rabie, A.; Wintersteiger, R.; Brugidou, J. Solid-phase Synthesis of Peptide Nucleic Acid (PNA) Monomers and Their Oligomerization Using Disulphide Anchoring Linkers. J. Peptide Sci. 1998, 4, 266-281.
    • (1998) J. Peptide Sci , vol.4 , pp. 266-281
    • Aldrian-Herrada, G.1    Rabie, A.2    Wintersteiger, R.3    Brugidou, J.4
  • 32
    • 34147130980 scopus 로고    scopus 로고
    • Novel monomer elements for marking peptidic nucleic acids.
    • WO Patent 9842735
    • Bergmann, F.; Herrmann, R.; Seidel, C.; Koch, T. Novel monomer elements for marking peptidic nucleic acids. WO Patent 9842735 (1998).
    • (1998)
    • Bergmann, F.1    Herrmann, R.2    Seidel, C.3    Koch, T.4
  • 33
    • 1942455433 scopus 로고    scopus 로고
    • Synthesis and biological activity of novel substituted pyridines and purines containing 2,4-thiazolidinedione
    • Kim, B. Y.; Ahn, J. B.; Lee, H. W.; Kang, S. K.; Lee, J. H.; Shin, J. S.; Ahn, S. K.; Hong, C. I.; Yoon, S. S. Synthesis and biological activity of novel substituted pyridines and purines containing 2,4-thiazolidinedione. Eur. J. Med. Chem. 2004, 39, 433-447.
    • (2004) Eur. J. Med. Chem , vol.39 , pp. 433-447
    • Kim, B.Y.1    Ahn, J.B.2    Lee, H.W.3    Kang, S.K.4    Lee, J.H.5    Shin, J.S.6    Ahn, S.K.7    Hong, C.I.8    Yoon, S.S.9
  • 34
    • 20544464406 scopus 로고    scopus 로고
    • Tetrabutylammonium fluoride-assisted rapid N9-alkylation on purine ring: Application to combinatorial reactions in microtiter plates for the discovery of potent sulfotransferase inhibitors in situ
    • Brik, A.; Wu, C-Y; Best, M. D.; Wong, C-H. Tetrabutylammonium fluoride-assisted rapid N9-alkylation on purine ring: Application to combinatorial reactions in microtiter plates for the discovery of potent sulfotransferase inhibitors in situ. Bioorg. & Med. Chem. 2005, 13, 4622-4626.
    • (2005) Bioorg. & Med. Chem , vol.13 , pp. 4622-4626
    • Brik, A.1    Wu, C.-Y.2    Best, M.D.3    Wong, C.-H.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.