메뉴 건너뛰기




Volumn 16, Issue 5, 2011, Pages 3985-3998

Synthesis of a novel benzoyl adenosine analog containing a 1, 4-dioxane sugar analog and the synthesis of a corresponding uracil adenine dinucleotide

Author keywords

1,4 dioxane; Adenosine; Heterocyclic; Nucleoside analogs; Uracil adenine

Indexed keywords


EID: 79957619755     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules16053985     Document Type: Article
Times cited : (2)

References (33)
  • 1
    • 0035038033 scopus 로고    scopus 로고
    • Sugar-modified nucleosides in past 10 years, a review
    • Ichikawa, E.; Kato, K. Sugar-modified nucleosides in past 10 years, a review. Curr. Med. Chem. 2001, 8, 385-423. (Pubitemid 32409787)
    • (2001) Current Medicinal Chemistry , vol.8 , Issue.4 , pp. 385-423
    • Ichikawa, E.1    Kato, K.2
  • 2
    • 0021849910 scopus 로고
    • Synthesis and biological activity of nucleoside analogs involving modification in the carbohydrate ring
    • Szarek, W.A.; Pinto, B.M.; Iwakawa, M. Synthesis and biological activity of nucleoside analogues involving modifications in the carbohydrate ring. Can. J. Chem. 1985, 63, 2149-2161. (Pubitemid 15023863)
    • (1985) Canadian Journal of Chemistry , vol.63 , Issue.8 , pp. 2149-2161
    • Szarek, W.A.1    Mario Pinto, B.2    Iwakawa, M.3
  • 3
    • 0019961274 scopus 로고
    • Synthesis and biological evaluation of novel pyrimidine nucleoside analogues of 1,4-oxathiane, 1,4-dithiane, and 1,4-dioxane
    • DOI 10.1021/jm00347a008
    • Hronowski, L.J.; Szarek, W.A. Synthesis and biological evaluation of novel pyrimidine nucleoside analogues of 1,4-oxathiane, 1,4-dithiane, and 1,4-dioxane. J. Med. Chem. 1982, 25, 522-526. (Pubitemid 12051975)
    • (1982) Journal of Medicinal Chemistry , vol.25 , Issue.5 , pp. 522-526
    • Hronowski, L.J.J.1    Szarek, W.A.2
  • 4
    • 0023036776 scopus 로고
    • Synthesis and antiviral evaluation of 1,4-dioxane nucleoside analogues related to nucleoside dialdehydes
    • DOI 10.1021/jm00162a005
    • Prisbe, E.J. Synthesis and antiviral evaluation of 1,4-dioxane nucleoside analogues related to nucleoside dialdehydes. J. Med. Chem. 1986, 29, 2445-2450. (Pubitemid 17211403)
    • (1986) Journal of Medicinal Chemistry , vol.29 , Issue.12 , pp. 2445-2450
    • Prisbe, E.J.1
  • 5
    • 0030771177 scopus 로고    scopus 로고
    • Synthesis of a novel dioxane nucleoside having two bases, 2(R)-(5-fluouracil-1-yl)-5(R)-hydroxymethyl-3(R)(-uracil-1-yl)-1,4-dioxane and its 2(S)-isomer, from uridine
    • DOI 10.1016/S0040-4039(97)01613-4, PII S0040403997016134
    • Mitsuaki, M.; Naoko, K.; Yamaizumi, Z.; Okamoto, Y.; Nagahara, K.; Takayanagi, H. Synthesis of a novel dioxane nucleoside having two bases, 2(R)-(5-fluorouracil-1-yl)-5(R)-hydroxymethyl- 3(R)-(uracil-1-yl)-1,4-dioxane and its 2(S)-isomer, from uridine. Tetrahedron Lett. 1997, 38, 6841-6844. (Pubitemid 27410281)
    • (1997) Tetrahedron Letters , vol.38 , Issue.39 , pp. 6841-6844
    • Maeda, M.1    Kajimoto, N.2    Yamaizumi, Z.3    Okamoto, Y.4    Nagahara, K.5    Takayanagi, H.6
  • 6
    • 84987377787 scopus 로고
    • Synthesis of nucleoside analogues of 1, 4-oxathiane 1,4-dothiane, and 1,4-dioxane
    • Szarek, W.A.; Vyas, D.M.; Achmatowicz, B. Synthesis of nucleoside analogues of 1,4-oxathiane, 1,4-dothiane, and 1,4-dioxane. J. Heteroc. Chem. 1975, 12, 123-127.
    • (1975) J. Heteroc. Chem. , vol.12 , pp. 123-127
    • Szarek, W.A.1    Vyas, D.M.2    Achmatowicz, B.3
  • 7
    • 67651215414 scopus 로고    scopus 로고
    • Synthesis of a novel, optically active uridine analog containing a 1,4- dioxane sugar moiety. Synthesis of the corresponding dinucleotide
    • Qiang, Y.; Carlsen, P. Synthesis of a Novel, Optically Active Uridine Analog Containing a 1,4- dioxane Sugar Moiety. Synthesis of the Corresponding Dinucleotide. Nucleos. Nucleot. Nucl. Acids 2009, 28, 165-174.
    • (2009) Nucleos. Nucleot. Nucl. Acids , vol.28 , pp. 165-174
    • Qiang, Y.1    Carlsen, P.2
  • 8
    • 0021760477 scopus 로고
    • Polymer support oligonucleotide synthesis. XVIII: Use of -cyanoethyl-N,N-dialkylamino-/N-morpholino phosphorami-dite of deoxynucleosides for the synthesis of DNA fragments simplifying deprotection and isolation of the final product
    • Sinha, N.D.; Biernat, J.; Mcmanus, J. Köster, H. Polymer support oligonucleotide synthesis. XVIII: use of -cyanoethyl-N,N-dialkylamino-/N- morpholino phosphorami-dite of deoxynucleosides for the synthesis of DNA fragments simplifying deprotection and isolation of the final product. Nucl. Acids Res. 1984, 12, 4539-4557.
    • (1984) Nucl. Acids Res. , vol.12 , pp. 4539-4557
    • Sinha, N.D.1    Biernat, J.2    Mcmanus, J.3    Köster, H.4
  • 9
    • 0025816110 scopus 로고
    • Selective monoalkylation of acyclic diols by means of dibutyltin oxide and fluoride salts
    • Nagashima, N.; Ohno, M. Selective monoalkylation of acyclic diols by means of dibutyltin oxide and fluoride salts. Chem. Pharm. Bull. 1991, 39, 1972-1982.
    • (1991) Chem. Pharm. Bull. , vol.39 , pp. 1972-1982
    • Nagashima, N.1    Ohno, M.2
  • 10
    • 0000655704 scopus 로고
    • An efficient O-monoalkylation of dimethyl L-tartrate via O-stannylene acetal with alkyl halides in the presence of caesium fluoride
    • Nagashima, N.; Ohno, M. An efficient O-monoalkylation of dimethyl L-tartrate via O-stannylene acetal with alkyl halides in the presence of caesium fluoride. Chem. Lett. 1987, 1, 141-144.
    • (1987) Chem. Lett. , vol.1 , pp. 141-144
    • Nagashima, N.1    Ohno, M.2
  • 11
    • 33748737594 scopus 로고    scopus 로고
    • Cycloadducts from highly functionalized nitrones and oximes as ligands in the enantioselective addition of diethylzinc to benzaldehyde
    • Baskaran, S.; Aurich, H.G.; Biesemeier, F.; Harms, K. Cycloadducts from highly functionalized nitrones and oximes as ligands in the enantioselective addition of diethylzinc to benzaldehyde. J. Chem. Soc. Perkin Trans. 1 1998, 22, 3717-3724. (Pubitemid 128761409)
    • (1998) Journal of the Chemical Society - Perkin Transactions 1 , Issue.22 , pp. 3717-3724
    • Baskaran, S.1    Aurich, H.G.2    Biesemeier, F.3    Harms, K.4
  • 12
    • 0002924344 scopus 로고
    • Reduction of malonic enolates with lithium aluminum hydride
    • Marshall, J.A.; Andersen, N.H.; Hochstetler, A. Reduction of malonic enolates with lithium aluminum hydride. J. Org. Chem. 1967, 32, 113-118.
    • (1967) J. Org. Chem. , vol.32 , pp. 113-118
    • Marshall, J.A.1    Andersen, N.H.2    Hochstetler, A.3
  • 13
    • 0034671050 scopus 로고    scopus 로고
    • 2-symmetric 2,3-disubstituted aziridine and 2,6-disubstituted piperidine as chiral ligands in the addition reaction of diethylzinc with arylaldehydes
    • DOI 10.1016/S0957-4166(00)00479-1, PII S0957416600004791
    • Shi, M.; Jiang, J.-K.; Feng, Y.-S. Chiral C2-symmetric 2,3-disubstituted aziridine and 2,6- disubstituted piperidine as chiral ligands in the addition reaction of diethylzinc with arylaldehydes. Tetrahedron Asymmetry 2000, 11, 4923-4933. (Pubitemid 32155303)
    • (2000) Tetrahedron Asymmetry , vol.11 , Issue.24 , pp. 4923-4933
    • Shi, M.1    Jiang, J.-K.2    Feng, Y.-S.3
  • 14
    • 0028052245 scopus 로고
    • Stereoselective synthesis of higher sugars by homologation of carbohydrate-derived enals with nonracemic γ-(silyloxy) allylic stannanes and substrate-directed hydroxylation
    • DOI 10.1021/jo00101a020
    • Marshall, J.A.; Beaudion, S. Stereoselective Synthesis of Higher Sugars by Homologation of Carbohydrate-Derived Enals with Nonracemic .-(Silyloxy) Allylic Stannanes and Substrate- Directed Hydroxylation. J. Org. Chem. 1994, 59, 6614-6619. (Pubitemid 24356821)
    • (1994) Journal of Organic Chemistry , vol.59 , Issue.22 , pp. 6614-6619
    • Marshall, J.A.1    Beaudoin, S.2
  • 17
    • 84982068675 scopus 로고
    • Nucleoside syntheses. XXII. Nucleoside synthesis with trimethylsilyl triflate and perchlorate as catalysts
    • Vorbrüggen, H.; Krolikiewicz, K. Nucleoside syntheses. XXII. Nucleoside synthesis with trimethylsilyl triflate and perchlorate as catalysts. Chem. Ber. 1981, 114, 1234-1255.
    • (1981) Chem. Ber. , vol.114 , pp. 1234-1255
    • Vorbrüggen, H.1    Krolikiewicz, K.2
  • 18
    • 84982058693 scopus 로고
    • Nucleoside syntheses. XXIII. On the mechanism of nucleoside synthesis
    • Vorbrüggen, H.; Höfle, G. Nucleoside syntheses. XXIII. On the mechanism of nucleoside synthesis. Chem. Ber. 1981, 114, 1256-1268.
    • (1981) Chem. Ber. , vol.114 , pp. 1256-1268
    • Vorbrüggen, H.1    Höfle, G.2
  • 20
    • 0036010560 scopus 로고    scopus 로고
    • Difficulties in the deprotection of 1,2-ketals in nucleosides containing alkylidencarbazoyl groups
    • DOI 10.1081/NCN-120006530
    • Magdalena, J.; Fernandez, S.; Ferrero, M.; Gotor, V. Difficulties in the deprotection of 1,2-ketals in nucleosides containing alkylidencarbazoyl groups. Nucleos. Nucleoti. Nucl. Acids 2002, 21, 55-64. (Pubitemid 34327063)
    • (2002) Nucleosides, Nucleotides and Nucleic Acids , vol.21 , Issue.1 , pp. 55-64
    • Magdalena, J.1    Fernandez, S.2    Ferrero, M.3    Gotor, V.4
  • 21
    • 13344254145 scopus 로고
    • Ethylidene derivatives of D-erythrose. I. 2,3-O-Ethylidene-β- Derythrofuranose
    • Van Cleve, J.W.; Rist, C.E. Ethylidene derivatives of D-erythrose. I. 2,3-O-Ethylidene-β-Derythrofuranose. Carbohydr. Res. 1967, 4, 82-92.
    • (1967) Carbohydr. Res. , vol.4 , pp. 82-92
    • Van Cleve, J.W.1    Rist, C.E.2
  • 22
    • 0343935632 scopus 로고
    • Conformational analysis in carbohydrate chemistry. Part IV. Intramolecular acetal formation by primary versus secondary hydroxyl groups
    • Angyal, S.J.; Beveridge, R.J. Conformational analysis in carbohydrate chemistry. Part IV. Intramolecular acetal formation by primary versus secondary hydroxyl groups. Carbohydr. Res. 1978, 65, 229-234.
    • (1978) Carbohydr. Res. , vol.65 , pp. 229-234
    • Angyal, S.J.1    Beveridge, R.J.2
  • 23
    • 0029950404 scopus 로고    scopus 로고
    • Facile Syntheses of Valiolamine and Its Diastereomers from (-)-Quinic Acid. Nucleophilic Substitution Reactions of 5-(Hydroxy-methyl)cyclohexane-1,2, 3,4,5-pentol
    • Shing, T.K.M.; Wan, L.H. Facile Syntheses of Valiolamine and Its Diastereomers from (-)-Quinic Acid. Nucleophilic Substitution Reactions of 5-(Hydroxy-methyl)cyclohexane-1,2,3,4,5-pentol. J. Org. Chem. 1996, 61, 8468-8479.
    • (1996) J. Org. Chem. , vol.61 , pp. 8468-8479
    • Shing, T.K.M.1    Wan, L.H.2
  • 24
    • 33845375399 scopus 로고
    • Efficient and selective cleavage of acetals and ketals using ferric chloride adsorbed on silica gel
    • Kim, K.S.; Song, Y.H.; Lee, B.H.; Hahn, C.S. Efficient and selective cleavage of acetals and ketals using ferric chloride adsorbed on silica gel. J. Org. Chem. 1986, 51, 404-406.
    • (1986) J. Org. Chem. , vol.51 , pp. 404-406
    • Kim, K.S.1    Song, Y.H.2    Lee, B.H.3    Hahn, C.S.4
  • 25
    • 0000774393 scopus 로고
    • A new, facile method for cleavage of acetals and dithioacetals
    • Szarek, W.A.; Zamojski, A. A new, facile method for cleavage of acetals and dithioacetals. Tetrahedron Lett. 1986, 27, 3827-3830.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 3827-3830
    • Szarek, W.A.1    Zamojski, A.2
  • 26
    • 0001754290 scopus 로고
    • A practical synthesis of 1,2,3,6-tetra-O-acetyl-a- and β-D-glucopyranose, and their use to prepare trisaccharides
    • Hall, D.M.; Lawler, T.E.; Childress, B.C. A practical synthesis of 1,2,3,6-tetra-O-acetyl-a- and β-D-glucopyranose, and their use to prepare trisaccharides. Carbohydr. Res. 1974, 38, 359-363.
    • (1974) Carbohydr. Res. , vol.38 , pp. 359-363
    • Hall, D.M.1    Lawler, T.E.2    Childress, B.C.3
  • 27
    • 0037131951 scopus 로고    scopus 로고
    • 13C labeled anti-HIV nucleosides as mass-internal standards
    • DOI 10.1016/S0040-4020(02)01246-2, PII S0040402002012462
    • Saito, Y.; Zevaco, T.A.; Agrofoglio, L.A. Chemical synthesis of 13C labeled anti-HIV nucleosides as mass-internal standards. Tetrahedron 2002, 58, 9593-9603. (Pubitemid 35356450)
    • (2002) Tetrahedron , vol.58 , Issue.47 , pp. 9593-9603
    • Saito, Y.1    Zevaco, T.A.2    Agrofoglio, L.A.3
  • 28
    • 33746190628 scopus 로고    scopus 로고
    • Facile and regioselective preparation of partly O-benzylated d-glucopyranose acetates via acid-mediated simultaneous debenzylation-acetolysis
    • DOI 10.1016/j.carres.2006.05.018, PII S0008621506002795
    • Cao, Y.; Okada, Y.; Yamada, H. Facile and regioselective preparation of partly O-benzylated D-glucopyranose acetates via acid-mediated simultaneous debenzylation-acetolysis. Carbohydr. Res. 2006, 341, 2219-2223. (Pubitemid 44092675)
    • (2006) Carbohydrate Research , vol.341 , Issue.13 , pp. 2219-2223
    • Cao, Y.1    Okada, Y.2    Yamada, H.3
  • 29
    • 0000596398 scopus 로고
    • Oligoribonucleotide synthesis. II. Preparation of 2'-Otetrahydropyranol derivatives of adenosine and cytidine necessary for insertion in stepwise synthesis
    • Neilson, T.; Werstiuk, E.S. Oligoribonucleotide synthesis. II. Preparation of 2'-Otetrahydropyranol derivatives of adenosine and cytidine necessary for insertion in stepwise synthesis. Can. J. Chem. 1971, 49, 493-499.
    • (1971) Can. J. Chem. , vol.49 , pp. 493-499
    • Neilson, T.1    Werstiuk, E.S.2
  • 30
    • 0021100730 scopus 로고
    • Color coded triarylmethyl protecting groups useful for deoxypolynucleotide synthesis
    • Fisher, E.F.; Caruthers, M.H. Color coded triarylmethyl protecting groups useful for deoxypolynucleotide synthesis. Nucl. Acids Res. 1983, 11, 1589-1599.
    • (1983) Nucl. Acids Res. , vol.11 , pp. 1589-1599
    • Fisher, E.F.1    Caruthers, M.H.2
  • 31
    • 0345732326 scopus 로고    scopus 로고
    • Synthesis of a formamidine-protected 5′-amino-2′,5′- dideoxyguanosine phosphoramidite and preparation of 5′- acylamidooligonucleotides
    • DOI 10.1016/j.tetlet.2003.11.003
    • Stütz, J.A.R.; Richert, C. Synthesis of a formamidine-protected 5'-amino-2',5'-dideoxy-guanosine phosphoramidite and preparation of 5'-acylamidooligonucleotides. Tetrahedron Lett. 2004, 45, 509-513. (Pubitemid 38016206)
    • (2004) Tetrahedron Letters , vol.45 , Issue.3 , pp. 509-513
    • Rojas Stutz, J.A.1    Richert, C.2
  • 33
    • 0028271891 scopus 로고
    • Rapid and efficient syntheses of phosphorylated dinucleotides
    • Ferris, J.P.; Peyser, J.R. Rapid and efficient syntheses of phosphorylated dinucleotides. Nucleos. Nucleot. 1994, 13, 1087-1111. (Pubitemid 24160987)
    • (1994) Nucleosides and Nucleotides , vol.13 , Issue.5 , pp. 1087-1111
    • Ferris, J.P.1    Peyser, J.R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.