SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 20, 2008, Pages 3129-3132

The synthesis of a novel C-nucleoside designed as guanosine analogue

(6) Kourafalos, Vassilios N a Tite, Tony a Mikros, Emmanuel a Marakos, Panagiotis a Pouli, Nicole a Balzarini, Jan b

a UNIVERSITY OF ATHENS (Greece)

b REGA INSTITUTE FOR MEDICAL RESEARCH (Belgium)

Author keywords

C nucleosides; Guanosine; Heterocycles; Lithiation; Proton deuterium exchange; Pyrazolo 3,4 c pyridine; Ring annulation

Indexed keywords

EID: 58149360005 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-0028-1087276 Document Type: Article

Times cited : (3)

References (32)

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22
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- Preparation of 1-Acetyl-5-pthalimido-7-methoxy-1H-pyrazolo[3,4-c] pyridine (7) Potassium acetate (77 mg, 0.78 mmol) and Ac2O (0.15 mL, 1.56 mmol) were added under argon to a solution of the acetamide 6 (170 mg, 0.52 mmol) in dry benzene (40 mL, The reaction mixture was heated at 80°C, isoamyl nitrite (0.07 mL, 0.52 mmol) was added, and the resulting mixture was refluxed for 10 h. The insoluble material was then filtered off, the solvent was vacuum evaporated, and the residue was purified by column chromatography (silica gel) using a mixture of cyclohexane-EtOAc (60:40, v/v) as the eluent to give 7 as a white solid (153 mg, 87, mp >300°C (EtOH, 1H NMR (400 MHz, CDCl 3, δ, 2.84 (s, 3 H, COCH3, 4.13 (s, 3 H, OCH 3, 7.82 (m, 3 H, H-4, H-4′, H-5′, 7.98 (m, 2 H, H-3′, H-6′, 8.17 (s, 1 H, H-3, 13C NMR 50 MHz, CDCl3
- 4: C, 60.71; H, 3.60; N, 16.66. Found: C, 60.82; H, 3.45; N, 16.88.

23
- 58149344111
- Preparation of 7-Methoxy-1H-pyrazolo[3,4- c]pyridin-5-amine (8) Compound 7 (120 mg, 0.73 mmol) was dissolved in a sat. solution of NH3 in MeOH. The solution was stirred at r.t. for 4 h, the solvent was vacuum evaporated, and the residue was purified by column chromatography (silica gel) using a mixture of cyclohexane-EtOAc (20:80, v/v) as the eluent to give 8 (54 mg, 92, as white crystals; mp 162-164°C (EtOH, 1H NMR (400 MHz, CDCl 3, δ, 4.07 (s, 3 H, OCH3, 5.20 (br s, 2 H, NH2, D2O exch, 6.29 (s, 1 H, H-4, 7.82 (s, 1 H, H-3, 13C NMR (50 MHz, CDCl3, δ, 53.3 (OCH3, 86.8 (C-4, 122.9 (C-7a, 132.0 (C-3a, 132.7 (C-3, 149.1 (C-5, 149.6 C-7, Anal. Calcd for C7H8N4O: C, 51.21; H, 4.91; N, 34.13. Found: C, 51.43; H, 4.80; N, 34.26
- 4O: C, 51.21; H, 4.91; N, 34.13. Found: C, 51.43; H, 4.80; N, 34.26.

24
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25
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26
- 58149337691
- Preparation of 5-Amino-1H-pyrazolo[3,4-c]pyridin-7 (6H)-one (9) Sodium iodide (81 mg, 0.54 mmol) and TMSCl (68 μL, 0.54 mmol) were added under argon to a solution of 8 (85 mg, 0.52 mmol) in dry MeCN (5 mL, The resulting mixture was heated at 65°C for 3 h, the precipitate was filtered, washed with EtOAc, and it was purified by column chromatography (silica gel) using a mixture of EtOAc-MeOH (98:2, v/v) as the eluent to give 9 (60 mg, 77, mp >300°C (EtOH, 1H NMR (400 MHz, DMSO-d6, δ, 5.09 (br s, 2 H, NH2, D2O exch, 5.40 (s, 1 H, H-4, D 2O exch, 7.54 (s, 1 H, H-3, 10.50 (br s, 1 H, N6H, D2O exch, 13.38 br s, 1 H, N1H, D2O exch, Anal. Calcd for C6H6N4O: C, 48.00; H, 4.03; N, 37.32. Found: C, 47.83; H, 3.95; N, 37.17
- 4O: C, 48.00; H, 4.03; N, 37.32. Found: C, 47.83; H, 3.95; N, 37.17.

27
- 58149353090
- Data for 7-Methoxy-3-(β-D-ribofuranosyl)-1H- pyrazolo[3,4-c]pyridin-5-amine (15) Mp 216-218°C (EtOH, 1H NMR (400 MHz, CD3OD, δ, 3.72 (dd, 1 H, H-5′, J4′,5′, 4.70 Hz, J 5′,5′, 12.13 Hz, 3.84 (dd, 1 H, H-5′, J4′,5′, 3.52 Hz, J 5′,5′, 12.13 Hz, 4.01 (m, 1 H, H-4′, 4.04 (s, 3 H, OCH3, 4.18 (m, 1 H, H-3′, 4.31 (m, 1 H, H-2′, 5.04 (d, 1 H, H-1′, J1′,2′, 6.65 Hz, 6.46 (s, 1 H, H-4, D2O exch, 13C NMR (50 MHz, CD3OD, δ, 53.7 (CH3O, 63.5 (C-5′, 72.7 (C-3′, 76.4 (C-2′, 80.4 (C-1′, 86.6 (C-4′, 87.9 (C-4, 124.0 (C-7a, 131.0 (C-3a, 143.2 (C-3, 150.7 C-7, Anal. Calcd for C12H 16N4O
- 5: C, 48.65; H, 5.44; N, 18.91. Found: C, 48.45; H, 5.28; N, 18.83.

28
- 58149335982
- 5: C, 46.81; H, 5.00; N, 19.85. Found: C, 46.75; H, 5.12; N, 19.97.
- 5: C, 46.81; H, 5.00; N, 19.85. Found: C, 46.75; H, 5.12; N, 19.97.

29
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- Sanghvi, Y.S.¹ Larson, S.B.² Robins, R.K.³ Revankar, G.R.⁴

30
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- Hadjipavlou, C.¹ Kostakis, I.K.² Pouli, N.³ Marakos, P.⁴ Mikros, E.⁵

31
- 48549089880
- Tsikouris, O.; Bartl, T.; Touek, J.; Lougiakis, N.; Tite, T.; Marakos, P.; Pouli, N.; Mikros, E.; Marek, R. Magn. Res. Chem. 2008, 46, 643.
- (2008) Magn. Res. Chem , vol.46 , pp. 643
- Tsikouris, O.¹ Bartl, T.² Touek, J.³ Lougiakis, N.⁴ Tite, T.⁵ Marakos, P.⁶ Pouli, N.⁷ Mikros, E.⁸ Marek, R.⁹

32
- 58149357828
- -1, using the Polak-Ribiere (conjugate gradient) geometry optimization method as implemented in the HyperChem 5.0 software (Hypercube Inc).
- -1, using the Polak-Ribiere (conjugate gradient) geometry optimization method as implemented in the HyperChem 5.0 software (Hypercube Inc).

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