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Volumn , Issue 11, 2009, Pages 1741-1744

The application of Mitsunobu cyclization for the synthesis of 2′,3′-dideoxy-C-nucleosides designed as didanosine analogues

Author keywords

C nucleosides; Dideoxynucleosides; Heterocycles; Pyrazolo 3,4 c pyridine; Pyrazolo 4,3 b pyridine

Indexed keywords

2',3' DIDEOXY 5' BENZYLRIBONOLACTONE; 2,3 DIDEOXY C NUCLEOSIDE; BORANE DERIVATIVE; DIDANOSINE; LACTONE DERIVATIVE; NUCLEOSIDE DERIVATIVE; PICOLINIC ACID; PYRAZOLO[3,4 C]PYRIDINE; PYRAZOLO[4,3 B]PYRIDINE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 67649998709     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1217364     Document Type: Article
Times cited : (7)

References (37)
  • 1
    • 0001178693 scopus 로고    scopus 로고
    • Biochemical pharmacology. Nucleoside and nonnucleoside reverse transcriptase inhibitors active against HIV
    • Merigan, T. C, Bartlett, J. G, Bolognesi, D, Eds, Williams and Wilkins: Philadelphia, Chap. 47, 815-847
    • (a) Balzarini, J.; De Clercq, E. Biochemical pharmacology. Nucleoside and nonnucleoside reverse transcriptase inhibitors active against HIV, In Textbook of AIDS Medicine; Merigan, T. C.; Bartlett, J. G.; Bolognesi, D., Eds.; Williams and Wilkins: Philadelphia, 1998, Chap. 47, 815-847.
    • (1998) Textbook of AIDS Medicine
    • Balzarini, J.1    De Clercq, E.2
  • 33
    • 67649973553 scopus 로고    scopus 로고
    • 1,6-Dihydro-3-(2,3-dideoxy-b-D-ribofuranosyl)-7Hpyrazolo[ 3,4-c]pyridin-7-one (15, mp 270-272°C (CH2Cl 2-MeOH, 1H NMR (400 MHz, CD3OD, δ, 1.88-2.02 (m, 1 H, H-3′, 2.08-2.25 (m, 2 H, H-2′, H-3′, 2.28-2.40 (m, 1 H, H-2′, 3.63 (dd, 1 H, H-5′, J5′,4′, 5.48 Hz, J5′,5′, 11.35 Hz, 3.70 (dd, 1 H, H-5′, J 5′,4′, 4.30 Hz, J5′,5′, 11.35 Hz, 4.13-4.22 (m, 1 H, H-4′, 5.22 (t, 1 H, H-1′, J 1′,2′, 7.04 Hz, 6.87 (d, 1 H, H-4, J4,5, 6.65 Hz, 6.95 (d, 1 H, H-5, J5,4, 6.65 Hz, 13C NMR (50 MHz, CD3OD, δ, 28.54 (C-3′, 32.97 (C-2′, 65.59 (C-5′, 77.27 (C-1′, 81.94 (C-4′, 101.72 (C-4, 125.69 (C-3α, 125.93 (C-5, 134.94 (C-7α, 148.07 (C-3, 156.55 C-7, Anal. Calcd for C11
    • 3: C, 56.16; H, 5.57; N, 17.86. Found: C, 56.01; H, 5.69; N, 17.68
  • 34
    • 67649964209 scopus 로고    scopus 로고
    • 1,4-Dihydro-3-(2,3-dideoxy-β-D-ribofuranosyl)-7H-pyrazolo[ 4,3-b]pyridin-7-one (30, Oil. 1H NMR (400 MHz, CD 3OD, δ, 2.00-2.23 (m, 3 H, 2 × H-3′, 1 × H-2′, 2.35-2.46 (m, 1 H, H-2′, 3.71 (dd, 1 H, H-5′, J 5′,4′, 3.13 Hz, J5′,5′, 11.74 Hz, 3.89 (dd, 1 H, H-5′, J5′,4′, 2.74 Hz, J 5′,5′, 11.74 Hz, 4.22-4.29 (m, 1 H, H-4′, 5.29 (t, 1 H, H-1′, J1′,2′, 7.04 Hz, 6.26 (d, 1 H, H-6, J6,5, 7.04 Hz, 7.77 (d, 1 H, H-5, J5,6, 7.04 Hz, 13C NMR (50 MHz, CD3OD, δ, 28.46 (C-3′, 34.19 (C-2′, 69.95 (C-5′, 77.95 (C-1′, 81.76 (C-4′, 110.23 (C-6, 128.49 (C-3α, 134.58 (C-7α, 138.77 (C-5, 142.86 (C-3, 171.12 C-7, Anal. Calcd for C11H13N 3O3
    • 3: C, 56.16; H, 5.57; N, 17.86. Found: C, 56.38; H, 5.39; N, 17.99


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.