메뉴 건너뛰기




Volumn 30, Issue 5, 2011, Pages 353-359

A new synthesis of 2-chloro-2'-deoxyadenosine (Cladribine), CdA)

Author keywords

2 chloro 2' deoxyadenosine (Cladribine) CdA); Barton McCombie reaction; new synthesis

Indexed keywords

ACETIC ACID; ACETIC ACID DERIVATIVE; CLADRIBINE; HYDROXYL GROUP; HYDROXYLAMINE; PYRIDINE;

EID: 79960827170     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770.2011.587701     Document Type: Article
Times cited : (19)

References (20)
  • 1
    • 0015366370 scopus 로고
    • Synthesis and biological activity of selected 2, 6-disubstituted(2-deoxy- .alpha.- and -.beta.-D-erythro-pentofuranosyl)purines
    • Christensen, L.F.; Broom, A.D.; Robins, M.J.; Bloch, A. Synthesis and biological activity of selected 2, 6-disubstituted(2-deoxy-.alpha.- and -.beta.-D-erythro-pentofuranosyl)purines. J. Med. Chem. 1972, 15(7), 735-739.
    • (1972) J. Med. Chem , vol.15 , Issue.7 , pp. 735-739
    • Christensen, L.F.1    Broom, A.D.2    Robins, M.J.3    Bloch, A.4
  • 2
    • 3042870116 scopus 로고
    • Deoxycytidine kinase-mediated toxicity of deoxyadenosine analogs toward malignant human lymphoblasts in vitro and toward murine L1210 leukemia in vivo
    • DOI 10.1073/pnas.77.11.6865
    • Carson, D.A.; Wasson, D.B.; Kaye, J.; Ullman, B.; Martin, D.W., Jr.; Robins, R.K.; Montgomery, J.A. Deoxycytidine kinase-mediated toxicity of deoxyadenosine analogs toward malignant human lymphoblasts in vitro and toward murine L1210 leukemia in vivo. Proc. Natl. Acad. Sci. 1980, 77(11), 6865-6869. (Pubitemid 11219046)
    • (1980) Proceedings of the National Academy of Sciences of the United States of America , vol.77 , Issue.11 , pp. 6865-6869
    • Carson, D.A.1    Wasson, D.B.2    Kaye, J.3
  • 3
    • 0026536178 scopus 로고
    • 2-Chlorodeoxyadenosine produces a high rate of complete hematologic remission in relapsed acute myeloid leukemia
    • Santana, V.M.; Mirro, J., Jr.; Kearns, C.; Schell, M.J.; Crom, W.; Blakley, R.L. 2-Chlorodeoxyadenosine produces a high rate of complete hematologic remission in relapsed acute myeloid leukemia. J. Clin. Oncol. 1992, 10(3), 364-370.
    • (1992) J. Clin. Oncol , vol.10 , Issue.3 , pp. 364-370
    • Santana, V.M.1    Mirro Jr., J.2    Kearns, C.3    Schell, M.J.4    Crom, W.5    Blakley, R.L.6
  • 4
    • 0023758320 scopus 로고
    • 2-Chlorodeoxyadenosine: An effective new agent for the treatment of chronic lymphocytic leukemia
    • Piro, L.D.; Carrera, C.J.; Beutler, E.; Carson, D.A. 2- Chlorodeoxyadenosine: an effective new agent for the treatment of chronic lymphocytic leukemia. Blood 1988, 72, 1069-1073.
    • (1988) Blood , vol.72 , pp. 1069-1073
    • Piro, L.D.1    Carrera, C.J.2    Beutler, E.3    Carson, D.A.4
  • 7
    • 84981761640 scopus 로고
    • /-deoxy-nucleosides of adenine, guanine and hypoxan-thine
    • /-deoxy-nucleosides of adenine, guanine and hypoxan-thine. Chem. Ber. 1960, 93(1), 140-149.
    • (1960) Chem. Ber , vol.93 , Issue.1 , pp. 140-149
    • Venner, H.1
  • 8
    • 0001742724 scopus 로고
    • Studies of nucleosides and nucleotides. XXIV.1 Purine cyclonucleosides. I. 8, cyclonucleoside derived from 2-chloro-8-mercapto-9-/?-D- xylofuranosyladenine
    • Ikehara, M.; Tada, H. Studies of nucleosides and nucleotides. XXIV.1 Purine cyclonucleosides. I. 8, cyclonucleoside derived from 2-chloro-8-mercapto- 9-/?-D-xylofuranosyladenine.J. Am. Chem. Soc. 1965, 87(3), 606-610.
    • (1965) J. Am. Chem. Soc , vol.87 , Issue.3 , pp. 606-610
    • Ikehara, M.1    Tada, H.2
  • 9
    • 33749129770 scopus 로고    scopus 로고
    • Regiospecific and highly stereoselective coupling of 6-(substituted- imidazol-1-yl)purines with 2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro- pentofuranosyl chloride. Sodium-salt glycosylation in binary solvent mixtures: Improved synthesis of cladribine
    • DOI 10.1021/jo061282+
    • Zhong, M.;Nowak, I.; Robins, M.J. Regiospecific and highly stereoselective coupling of 6-(substituted-imidazol-1-yl)purines with 2-deoxy-3, 5-di-O-(p-toluoyl)-r-D-erythro-pentofuranosyl chloride. Sodium-salt glycosylation in binary solvent mixtures: improved synthesis of cladribine.J. Org. Chem. 2006, 71, 7773-7779. (Pubitemid 44470319)
    • (2006) Journal of Organic Chemistry , vol.71 , Issue.20 , pp. 7773-7779
    • Zhong, M.1    Nowak, I.2    Robins, M.J.3
  • 16
    • 0036334531 scopus 로고    scopus 로고
    • A universal biocatalystforthe preparation of base-and sugar-modified nucleosides via an enzymatic transglycosylation
    • Barai, V.N.; Zinchenko, A.I.; Eroshevskaya, L.A.; Kalinichenko, E.N.; Kulak, T.I.; Mikhailopulo, I.A. A universal biocatalystforthe preparation of base-and sugar-modified nucleosides via an enzymatic transglycosylation. Helv. Chim. Acta 2002, 85(7), 1901-1908.
    • (2002) Helv. Chim. Acta , vol.85 , Issue.7 , pp. 1901-1908
    • Barai, V.N.1    Zinchenko, A.I.2    Eroshevskaya, L.A.3    Kalinichenko, E.N.4    Kulak, T.I.5    Mikhailopulo, I.A.6
  • 17
    • 0012118862 scopus 로고
    • Nucleic acid related compounds. 41. Restricted furanose conformations of 3, 5'-O-1, 1, 3, 3-tetraisopropyldisilox-1, 3-diyl)nucleosides provide a convenient evaluation of anomeric configuration
    • Robins, M.J.; Wilson, J.; Sawyer, L.; James, M.N.G. Nucleic acid related compounds. 41. Restricted furanose conformations of 3, 5'-O-(1, 1, 3, 3-tetraisopropyldisilox-1, 3-diyl)nucleosides provide a convenient evaluation of anomeric configuration. Can. J. Chem. 1983, 61, 1911-1920.
    • (1983) Can. J. Chem , vol.61 , pp. 1911-1920
    • Robins, M.J.1    Wilson, J.2    Sawyer, L.3    James, M.N.G.4
  • 18
    • 37049106090 scopus 로고
    • Partial protection of carbohydrate derivatives. Part 4. Regioselective 2-O-deacylation of fully acylated purine and pyrimidine ribonucleosides with hy-droxylaminium acetate
    • Ishido, Y; Sakairi, N.; Okazaki, K.; Nakazaki, N. Partial protection of carbohydrate derivatives. Part 4. Regioselective 2-O-deacylation of fully acylated purine and pyrimidine ribonucleosides with hy-droxylaminium acetate.J. Chem. Soc, Perkin Trans. 1, 1980, 563-573.
    • (1980) J. Chem. Soc. Perkin Trans. , vol.1 , pp. 563-573
    • Ishido, Y.1    Sakairi, N.2    Okazaki, K.3    Nakazaki, N.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.