SCOPUS 정보 검색 플랫폼

Synlett

Volumn , Issue 18, 2008, Pages 2836-2840

Original SRN1 reactions on new non-nitrated heterocyclic system

(3) Szabo, Rémi a Crozet, Maxime D a Vanelle, Patrice a

a Laboratoire de Pharmaco Chimie Radicalaire (France)

Author keywords

4H pyrido 1,2 a pyrimidin 4 one; Alkylation; Inhibitors; Single electron transfer; Spectroscopy

Indexed keywords

3 BROMO 7 CHLORO 2 (CHLOROMETHYL) 4H PYRIDO[1,2 A]PYRIMIDIN 4 ONE; CARBON; HETEROCYCLIC COMPOUND; NITROUS ACID; PYRIMIDINONE DERIVATIVE; SULFUR; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; BROMINATION; CATALYSIS; CHEMICAL REACTION; CRYSTAL STRUCTURE; CYCLIC POTENTIOMETRY; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTRON TRANSPORT; NITRATION; ROOM TEMPERATURE; SUBSTITUTION REACTION;

EID: 56849110944 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-0028-1083499 Document Type: Article

Times cited : (7)

References (49)

1
- 34948815084
- La Motta, C.; Sartini, S.; Mugnaini, L.; Simorini, F.; Taliani, S.; Salerno, S.; Marini, A. M.; Da Settimo, F.; Lavecchia, A.; Novellino, E.; Cantore, M.; Failli, P.; Ciuffi, M. J. Med. Chem. 2007, 50, 4917.
- (2007) J. Med. Chem , vol.50 , pp. 4917
- La Motta, C.¹ Sartini, S.² Mugnaini, L.³ Simorini, F.⁴ Taliani, S.⁵ Salerno, S.⁶ Marini, A.M.⁷ Da Settimo, F.⁸ Lavecchia, A.⁹ Novellino, E.¹⁰ Cantore, M.¹¹ Failli, P.¹² Ciuffi, M.¹³

2
- 56849116648
- WO 113335, 93843
- (a) Wang, W.; Constantine, R. N.; Lagniton, L. M.; Pecchi, S.; Burger, M. T.; Desai, M. C. WO 113335, 2004; Chem. Abstr. 2005, 142, 93843.
- (2004) Chem. Abstr , vol.142
- Wang, W.¹ Constantine, R.N.² Lagniton, L.M.³ Pecchi, S.⁴ Burger, M.T.⁵ Desai, M.C.⁶

3
- 19944432425
- (b) Griffin, R. J.; Fontana, G.; Golding, B. T.; Guiard, S.; Hardcastle, I. R.; Leahy, J. J. J.; Martin, N.; Richardson, C.; Rigoreau, L.; Stockley, M.; Smith, G. C. M. J. Med. Chem. 2005, 48, 569.
- (2005) J. Med. Chem , vol.48 , pp. 569
- Griffin, R.J.¹ Fontana, G.² Golding, B.T.³ Guiard, S.⁴ Hardcastle, I.R.⁵ Leahy, J.J.J.⁶ Martin, N.⁷ Richardson, C.⁸ Rigoreau, L.⁹ Stockley, M.¹⁰ Smith, G.C.M.¹¹

4
- 3843135141
- (c) Knight, Z. A.; Chiang, G. G.; Alaimo, P. J.; Kenski, D. M.; Ho, C. B.; Coan, K.; Abraham, R. T.; Shokat, K. M. Bioorg. Med. Chem. 2004, 12, 4749.
- (2004) Bioorg. Med. Chem , vol.12 , pp. 4749
- Knight, Z.A.¹ Chiang, G.G.² Alaimo, P.J.³ Kenski, D.M.⁴ Ho, C.B.⁵ Coan, K.⁶ Abraham, R.T.⁷ Shokat, K.M.⁸

5
- 56849087746
- WO 110868, 427370
- Tworowski, D.; Matsievitch, R. WO 110868, 2007; Chem. Abstr. 2007, 147, 427370.
- (2007) Chem. Abstr , vol.147
- Tworowski, D.¹ Matsievitch, R.²

6
- 34447098245
- Fujita, H.; Shimoji, Y.; Kojima, S.; Nishino, H.; Kamoshita, K.; Endo, K.; Kobayashi, S.; Kumakura, S.; Sato, Y. Sankyo Kenkyusho Nenpo 1977, 29, 75.
- (1977) Sankyo Kenkyusho Nenpo , vol.29 , pp. 75
- Fujita, H.¹ Shimoji, Y.² Kojima, S.³ Nishino, H.⁴ Kamoshita, K.⁵ Endo, K.⁶ Kobayashi, S.⁷ Kumakura, S.⁸ Sato, Y.⁹

7
- 33646569978
- Van der Mey, M.; Windhorst, A. D.; Klok, R. P.; Herscheid, J. D. M.; Kennis, L. E.; Bischoff, F.; Bakker, M.; Langlois, X.; Heylen, L.; Jurzak, M.; Leysen, J. E. Bioorg. Med. Chem. 2006, 14, 4526.
- (2006) Bioorg. Med. Chem , vol.14 , pp. 4526
- Van der Mey, M.¹ Windhorst, A.D.² Klok, R.P.³ Herscheid, J.D.M.⁴ Kennis, L.E.⁵ Bischoff, F.⁶ Bakker, M.⁷ Langlois, X.⁸ Heylen, L.⁹ Jurzak, M.¹⁰ Leysen, J.E.¹¹

8
- 56849119683
- Hes, R. V.; Smid, P.; Kruse, C. G.; Tulp, M. T. M. US 012206, 2006; Chem. Abstr. 2006, 145, 28008.
- Hes, R. V.; Smid, P.; Kruse, C. G.; Tulp, M. T. M. US 012206, 2006; Chem. Abstr. 2006, 145, 28008.

9
- 0016312333
- Magyar, K.; Satory, E.; Meszaros, Z.; Knoll, J. Med. Biol. 1974, 52, 384.
- (1974) Med. Biol , vol.52 , pp. 384
- Magyar, K.¹ Satory, E.² Meszaros, Z.³ Knoll, J.⁴

10
- 0021219316
- Colpaert, F. C.; Janssen, P. A. J. Eur. J. Pharmacol. 1984, 103, 169.
- (1984) Eur. J. Pharmacol , vol.103 , pp. 169
- Colpaert, F.C.¹ Janssen, P.A.J.²

11
- 32044469590
- (a) Yoshida, K.; Nakayama, K.; Kuru, N.; Kobayashi, S.; Ohtsuka, M.; Takemura, M.; Hoshino, K.; Kanda, H.; Zhang, J. Z.; Lee, V. J.; Watkins, W. J. Bioorg. Med. Chem. 2006, 14, 1993.
- (1993) Bioorg. Med. Chem , vol.2006 , pp. 14
- Yoshida, K.¹ Nakayama, K.² Kuru, N.³ Kobayashi, S.⁴ Ohtsuka, M.⁵ Takemura, M.⁶ Hoshino, K.⁷ Kanda, H.⁸ Zhang, J.Z.⁹ Lee, V.J.¹⁰ Watkins, W.J.¹¹

12
- 33750533367
- (b) Yoshida, K.; Nakayama, K.; Ohtsuka, M.; Takemura, M.; Hoshino, K.; Kanda, H.; Namba, K.; Nitanai, H.; Zhang, J. Z.; Lee, V. J.; Watkins, W. J. Bioorg. Med. Chem. 2006, 14, 8506.
- (2006) Bioorg. Med. Chem , vol.14 , pp. 8506
- Yoshida, K.¹ Nakayama, K.² Ohtsuka, M.³ Takemura, M.⁴ Hoshino, K.⁵ Kanda, H.⁶ Namba, K.⁷ Nitanai, H.⁸ Zhang, J.Z.⁹ Lee, V.J.¹⁰ Watkins, W.J.¹¹

13
- 0347360262
- (c) Nakayama, K.; Kawato, H.; Watanabe, J.; Ohtsuka, M.; Yoshida, K.; Yokomizo, Y.; Sakamoto, A.; Kuru, N.; Ohta, T.; Hoshino, K.; Yoshida, K.; Ishida, H.; Cho, A.; Palme, M. H.; Zhang, J. Z.; Lee, V. J.; Watkins, W. J. Bioorg. Med. Chem. Lett. 2004, 14, 475.
- (2004) Bioorg. Med. Chem. Lett , vol.14 , pp. 475
- Nakayama, K.¹ Kawato, H.² Watanabe, J.³ Ohtsuka, M.⁴ Yoshida, K.⁵ Yokomizo, Y.⁶ Sakamoto, A.⁷ Kuru, N.⁸ Ohta, T.⁹ Hoshino, K.¹⁰ Yoshida, K.¹¹ Ishida, H.¹² Cho, A.¹³ Palme, M.H.¹⁴ Zhang, J.Z.¹⁵ Lee, V.J.¹⁶ Watkins, W.J.¹⁷

14
- 33846351654
- Varma, H.; Voisine, C.; DeMarco, C. T.; Cattaneo, E.; Lo, D. C.; Hart, A. C.; Stockwell, B. R. Nat. Chem. Biol. 2007, 3, 99.
- (2007) Nat. Chem. Biol , vol.3 , pp. 99
- Varma, H.¹ Voisine, C.² DeMarco, C.T.³ Cattaneo, E.⁴ Lo, D.C.⁵ Hart, A.C.⁶ Stockwell, B.R.⁷

15
- 33646877668
- Vanelle, P, Ed, Research Signpost: Trivandrum
- Electron Transfer Reactions in Organic Synthesis; Vanelle, P., Ed.; Research Signpost: Trivandrum, 2002.
- (2002) Electron Transfer Reactions in Organic Synthesis

16
- 0037239899
- For a recent review, see
- For a recent review, see: Rossi, R. A.; Pierini, A. B.; Peñéñori, A. B. Chem. Rev. 2003, 103, 71.
- (2003) Chem. Rev , vol.103 , pp. 71
- Rossi, R.A.¹ Pierini, A.B.² Peñéñori, A.B.³

17
- 56849088263
- Part C; Fox, M. A, Chanon, M, Eds, Elsevier: Amsterdam, Chap. 4.8, 421-486
- 3-Carbon, Part C; Fox, M. A.; Chanon, M., Eds.; Elsevier: Amsterdam, 1988, Chap. 4.8, 421-486.
- (1988) 3-Carbon
- Bowman, W.R.¹

18
- 0000239817
- Kornblum, N.; Michael, R. E.; Kerber, R. C. J. Am. Chem. Soc. 1966, 88, 5660.
- (1966) J. Am. Chem. Soc , vol.88 , pp. 5660
- Kornblum, N.¹ Michael, R.E.² Kerber, R.C.³

19
- 0000233017
- (a) Kornblum, N.; Michel, R. E.; Kerber, R. C. J. Am. Chem. Soc. 1966, 88, 5662.
- (1966) J. Am. Chem. Soc , vol.88 , pp. 5662
- Kornblum, N.¹ Michel, R.E.² Kerber, R.C.³

20
- 33947336177
- (b) Russell, G. A.; Danen, W. C. J. Am. Chem. Soc. 1966, 88, 5663.
- (1966) J. Am. Chem. Soc , vol.88 , pp. 5663
- Russell, G.A.¹ Danen, W.C.²

21
- 2642594261
- (c) Shechter, H.; Kaplan, R. B. J. Am. Chem. Soc. 1951, 73, 1883.
- (1951) J. Am. Chem. Soc , vol.73 , pp. 1883
- Shechter, H.¹ Kaplan, R.B.²

22
- 33846669113
- (a) Verhaeghe, P.; Rathelot, P.; Rault, S.; Vanelle, P. Lett. Org. Chem. 2006, 3, 891.
- (2006) Lett. Org. Chem , vol.3 , pp. 891
- Verhaeghe, P.¹ Rathelot, P.² Rault, S.³ Vanelle, P.⁴

23
- 0002227735
- (b) Vanelle, P.; Crozet, M. P. Recent Res. Dev. Org. Chem. 1998, 2, 547.
- (1998) Recent Res. Dev. Org. Chem , vol.2 , pp. 547
- Vanelle, P.¹ Crozet, M.P.²

24
- 85008047871
- (c) Nishikawa, M.; Saeki, S.; Hamana, M.; Noda, H. Chem. Pharm. Bull. 1980, 28, 2436.
- (1980) Chem. Pharm. Bull , vol.28 , pp. 2436
- Nishikawa, M.¹ Saeki, S.² Hamana, M.³ Noda, H.⁴

25
- 0035280833
- Djekou, S.; Gellis, A.; Maldonado, J.; Crozet, M. P.; Vanelle, P. Heterocycles 2001, 55, 535.
- (2001) Heterocycles , vol.55 , pp. 535
- Djekou, S.¹ Gellis, A.² Maldonado, J.³ Crozet, M.P.⁴ Vanelle, P.⁵

26
- 33750947901
- Terme, T.; Crozet, M. D.; Gellis, A.; Vanelle, P. Recent Res. Dev. Org. Chem. 2004, 8, 437.
- (2004) Recent Res. Dev. Org. Chem , vol.8 , pp. 437
- Terme, T.¹ Crozet, M.D.² Gellis, A.³ Vanelle, P.⁴

27
- 45249101560
- Montana, M.; Crozet, M. D.; Castera-Ducros, C.; Terme, T.; Vanelle, P. Heterocycles 2008, 75, 925.
- (2008) Heterocycles , vol.75 , pp. 925
- Montana, M.¹ Crozet, M.D.² Castera-Ducros, C.³ Terme, T.⁴ Vanelle, P.⁵

28
- 0032834056
- Ferrarini, P. L.; Mori, C.; Mori, F.; Saccomanni, G.; Barontini, S.; Macchia, M.; Barili, P. L.; Hamdan, M. J. Heterocycl. Chem. 1999, 36, 1065.
- (1999) J. Heterocycl. Chem , vol.36 , pp. 1065
- Ferrarini, P.L.¹ Mori, C.² Mori, F.³ Saccomanni, G.⁴ Barontini, S.⁵ Macchia, M.⁶ Barili, P.L.⁷ Hamdan, M.⁸

29
- 0021848137
- (a) Horvath, G.; Hermecz, I.; Horvath, A.; Pongor-Csakvari, M.; Pusztay, L.; Kiss, A. I.; Czako, L.; Abdirizak, O. H. J. Heterocycl. Chem. 1985, 22, 481.
- (1985) J. Heterocycl. Chem , vol.22 , pp. 481
- Horvath, G.¹ Hermecz, I.² Horvath, A.³ Pongor-Csakvari, M.⁴ Pusztay, L.⁵ Kiss, A.I.⁶ Czako, L.⁷ Abdirizak, O.H.⁸

30
- 56849126692
- Dekeyser, M. A.; Moore, R. C.; Pierce, B. J.; Hubbard, W. L.; Winchester, L. EP 81945, 1983; Chem. Abstr. 1983, 100, 22795.
- (b) Dekeyser, M. A.; Moore, R. C.; Pierce, B. J.; Hubbard, W. L.; Winchester, L. EP 81945, 1983; Chem. Abstr. 1983, 100, 22795.

31
- 56849107128
- 2O: C, 35.10; H, 1.64; N, 9.10. Found: C, 35.11; H, 1.65; N, 8.96.
- 2O: C, 35.10; H, 1.64; N, 9.10. Found: C, 35.11; H, 1.65; N, 8.96.

32
- 26444512633
- (a) Médebielle, M.; Hohn, S.; Okada, E.; Myoken, H.; Shibata, D. Tetrahedron Lett. 2005, 46, 7817.
- (2005) Tetrahedron Lett , vol.46 , pp. 7817
- Médebielle, M.¹ Hohn, S.² Okada, E.³ Myoken, H.⁴ Shibata, D.⁵

33
- 0141425531
- (b) Médebielle, M.; Kato, K.; Dolbier, W. R. Jr. Tetrahedron Lett. 2003, 44, 7871.
- (2003) Tetrahedron Lett , vol.44 , pp. 7871
- Médebielle, M.¹ Kato, K.² Dolbier Jr., W.R.³

34
- 0030007180
- (a) Vanelle, P.; Donini, S.; Terme, T.; Maldonado, J.; Roubaud, C.; Crozet, M. P. Tetrahedron Lett. 1996, 37, 3323.
- (1996) Tetrahedron Lett , vol.37 , pp. 3323
- Vanelle, P.¹ Donini, S.² Terme, T.³ Maldonado, J.⁴ Roubaud, C.⁵ Crozet, M.P.⁶

35
- 0029145550
- (b) Roubaud, C.; Vanelle, P.; Maldonado, J.; Crozet, M. P. Tetrahedron 1995, 51, 9643.
- (1995) Tetrahedron , vol.51 , pp. 9643
- Roubaud, C.¹ Vanelle, P.² Maldonado, J.³ Crozet, M.P.⁴

36
- 56849096911
- Analytical Data for 3-Bromo-7-chloro-2-(2-methylprop-1-enyl)-4H-pyrido[1,2-a]pyrimidin-4-one(2) Shiny white plates, mp 175°C (EtOH-Et2O, 1H NMR (200 MHz, CDCl3, δ, 2.03 (d, J, 1.2 Hz, 3 H, 2.18 (d, J, 1.2 Hz, 3 H, 6.58 (sept, J, 1.2 Hz, 1 H, CH, 7.55 (dd, J, 9.5, 0.8 Hz, 1 H, 7.64 (dd, J, 9.5, 2.2 Hz, 1 H, 9.02 (dd, J, 2.2, 0.8 Hz, 1 H, 13C NMR (50 MHz, CDCl3, δ, 20.5, 28.1, 102.4, 122.4, 124.2, 125.2, 127.1, 137.0, 146.5, 149.2, 154.4, 159.7. Anal. Calcd for C12H10BrClN2O: C, 45.96; H, 3.21; N, 8.93. Found: C, 45.74; H, 3.24; N, 8.86. Crystal Data for Compound 2 C12H10BrClN2O, colorless prism (0.3 x 0.2 x 0.05 mm3, MW, 313.58, monoclinic, space group P21/c (T, 293 K, a, 7.1901(2) Å, b
- -1, F(000) = 624, index ranges -9 ≤ h ≤ 9,0 ≤ k ≤ 21, 0 ≤ l ≤ 15; θ range = 2.29-28.68°, 154 variables and 0 restraints, were refined for 2136 reflections with I ≥ 2σ(I) to R1 = 0.0403, wR2 = 0.1078, GooF = 1.050. CCDC 691139 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/data_request/cif of from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax:+44 (1223)336033; email: deposit@ccdc.cam.ac.uk.

37
- 0002392053
- Chanon, M.; Tobe, M. L. Angew. Chem., Int. Ed. Engl. 1982, 21, 1.
- (1982) Angew. Chem., Int. Ed. Engl , vol.21 , pp. 1
- Chanon, M.¹ Tobe, M.L.²

38
- 56849100280
- General Procedure and Analytical Data for Compounds 3-5 A solution of 60% NaH (3 equiv) in DMSO under an inert atmosphere was treated with dialkyl malonate (3 equiv) and stirred for 20 min. A solution of 1 (1 equiv) in DMSO was then added and the mixture was irradiated with a 60 W tungsten lamp and stirred until disappearance of the starting material as monitored by TLC. At this time, the mixture was poured into cold H2O. The aqueous solution was extracted with EtOAc. The organic layers were washed with brine, dried over anhyd Na2SO4, and evaporated under reduced pressure. The residue was purified by chromatography column on SiO2. Wanted products were recrystallized with BuOH or i-PrOH. Dimethyl 2, 3-Bromo-7-chloro-4-oxo-4H-pyrido[1,2-a] pyrimidin-2-yl)methyl}malonate (3) Pale yellow crystals, mp 147°C (i-PrOH, 1H NMR 200 MHz, CDCl3, δ, 3.5
- 5: C, 51.09; H, 3.67; N, 5.67. Found: C, 51.24; H, 3.76; N, 5.74.

39
- 0002878633
- (a) Miyake, H.; Yamamura, K. Bull. Chem. Soc. Jpn. 1986, 59, 89.
- (1986) Bull. Chem. Soc. Jpn , vol.59 , pp. 89
- Miyake, H.¹ Yamamura, K.²

40
- 0005596807
- (b) Norris, R. K.; Wright, T. A. Aust. J. Chem. 1985, 38, 1107.
- (1985) Aust. J. Chem , vol.38 , pp. 1107
- Norris, R.K.¹ Wright, T.A.²

41
- 3242829423
- (c) Palacios, S. M.; Alonso, R. A.; Rossi, R. A. Tetrahedron 1985, 41, 4147.
- (1985) Tetrahedron , vol.41 , pp. 4147
- Palacios, S.M.¹ Alonso, R.A.² Rossi, R.A.³

42
- 0012629103
- (d) Kornblum, N.; Kestner, M. N.; Boyd, S. D.; Cattran, L. C. J. Am. Chem. Soc. 1973, 95, 3356.
- (1973) J. Am. Chem. Soc , vol.95 , pp. 3356
- Kornblum, N.¹ Kestner, M.N.² Boyd, S.D.³ Cattran, L.C.⁴

43
- 56849132482
- Analytical Data for Compounds 6-9 3-Bromo-7-chloro-2-(phenylsulfonyl- methyl)-4H-pyrido-[1,2-a]pyrimidin-4-one (6) Beige needles, mp 234°C (i-PrOH, 1H NMR (200 MHz, CDCl3, δ, 4.81 (s, 2 H, 7.48-7.57 (m, 3 H, 7.64-7.74 (m, 2 H, 7.84-7.89 (m, 2 H, 9.01 (d, J, 2.0 Hz, 1 H, 13C NMR (50 MHz, CDCl3, δ, 63.9, 105.9, 125.3, 125.6, 127.3, 128.6, 129.2, 134.1, 137.9, 139.4, 147.0, 153.3, 153.9. Anal. Calcd for C 15H10BrClN2O3S: C, 43.55; H, 2.44; N, 6.77; S, 7.75. Found: C, 44.08; H, 2.53; N, 6.72; S, 7.78. 3-Bromo-7-chloro-2-(tosylmethyl)-4H-pyrido[1, 2-a]pyrimidin-4-one (7) White needles, mp 225°C (i-PrOH, 1H NMR (200 MHz, CDCl3, δ, 2.45 (s, 3 H, 4.79 (s, 2 H, 7.32 (d, J, 8.0 Hz, 2 H, 7.55 (dd, J, 9.5, 0.7 Hz, 1 H, 7.69-7.76 m
- 2OS: C, 47.20; H, 2.64; N, 7.34; S, 8.40. Found: C, 47.00; H, 2.60; N, 7.46; S, 8.21.

44
- 34250626098
- (a) Roydhouse, M. D.; Walton, J. C. Eur. J. Org. Chem. 2007, 1059..
- (2007) Eur. J. Org. Chem , pp. 1059
- Roydhouse, M.D.¹ Walton, J.C.²

45
- 33748548368
- (b) Guastavino, J. F.; Barolo, S. M.; Rossi, R. A. Eur. J. Org. Chem. 2006, 3898.
- (2006) Eur. J. Org. Chem , pp. 3898
- Guastavino, J.F.¹ Barolo, S.M.² Rossi, R.A.³

46
- 0035862681
- (a) Vanelle, P.; Terme, T.; Giraud, L.; Crozet, M. P. Tetrahedron Lett. 2001, 42, 391..
- (2001) Tetrahedron Lett , vol.42 , pp. 391
- Vanelle, P.¹ Terme, T.² Giraud, L.³ Crozet, M.P.⁴

47
- 0034641454
- (b) Vanelle, P.; Terme, T.; Crozet, M. P. Tetrahedron Lett. 2000, 41, 6383..
- (2000) Tetrahedron Lett , vol.41 , pp. 6383
- Vanelle, P.¹ Terme, T.² Crozet, M.P.³

48
- 0030007180
- (c) Vanelle, P.; Donini, S.; Terme, T.; Maldonado, J.; Roubaud, C.; Crozet, M. P. Tetrahedron Lett. 1996, 37, 3323..
- (1996) Tetrahedron Lett , vol.37 , pp. 3323
- Vanelle, P.¹ Donini, S.² Terme, T.³ Maldonado, J.⁴ Roubaud, C.⁵ Crozet, M.P.⁶

49
- 0025886440
- (d) Crozet, M. P.; Giraud, L.; Sabuco, J.-F.; Vanelle, P.; Barreau, M. Tetrahedron Lett. 1991, 32, 4125.
- (1991) Tetrahedron Lett , vol.32 , pp. 4125
- Crozet, M.P.¹ Giraud, L.² Sabuco, J.-F.³ Vanelle, P.⁴ Barreau, M.⁵

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.