Direct metallation of thienopyrimidines using a mixed lithium-cadmium base and antitumor activity of functionalized derivatives
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- Ήφαιστος Γλυκύς
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1 Direct metallation of thienopyrimidines using a mixed lithium-cadmium base and antitumor activity of functionalized derivatives Katia négaroff, a Frédéric Lassagne, a Ghenia Bentabed-Ababsa, a,b Ekhlass assar, c idaty Cheikh id Ely, a téphanie Hesse, d Enrico Perspicace, d Aïcha Derdour b and Florence Mongin* a a Chimie et Photonique Moléculaires, UMR 6510 CR, Université de Rennes 1, Bâtiment 10A, Case 3, Campus cientifique de Beaulieu, 342 Rennes, France b Laboratoire de ynthèse Organique Appliquée, Faculté des ciences de l'université, BP 1524 Es-enia, Oran 30, Algérie c Department of Chemistry, Faculty of Women for Arts, cience and Education, Ain hams University, Asma Fahmy treet, Heleopolis (El-Margany), Cairo, Egypt d Laboratoire d ngéniérie Moléculaire et Biochimie Pharmacologique, nstitut Jean Barriol, FR CR 2843, Université Paul Verlaine-Metz, 1 Boulevard Arago, Metz Technopôle, France florence.mongin@univ-rennes1.fr X-ray diffraction analysis p. 1 MR data p. 2 Copies of MR spectra p. 5
2 X-ray diffraction analysis The sample was studied with graphite monochromatized Mo Kα radiation (λ = Å). X-ray diffraction data were collected at T = (2) K using APEX Bruker-AX diffractometer. The structure was solved by direct methods using the R97 program, 1 and then refined with full-matrix least-square methods based on F 2 (HELX-97) 2 with the aid of the WGX program. 3 All non-hydrogen atoms were refined with anisotropic thermal parameters. H atoms were finally included in their calculated positions. Except -linked hydrogen that was introduced in the structural model through Fourier difference maps analysis, H atoms were finally included in their calculated positions. The molecular diagram was generated by ORTEP-3 (version 1.08). 4 ORTEP figure Cl Ph 10a Crystal data 10a: C 12 H 6 Cl 2 ; M r = ; T = (2) K; λ = Å; orthorombic; space group P c a b, a = (2) Å, b = (6) Å, c = (9) Å, V = (15) Å 3 ; Z = 8; D c = g cm -3 ; μ = 35 mm -1 ; F(000) = 1424; crystal size = 0.22 x 0.08 x 0.06 mm; θ range for data collection: , limiting indices: -7 h 7, -21 k 19, -31 l 30; reflections collected; 2743 reflections unique (R int = ); R 1 (>2σ())= ; wr 2 (>2σ())= ; Crystallographic data were deposited in CD under CCDC registration number A. Altomare, M. C. Burla, M. Camalli, G. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. pagna, J. Appl. Crystallogr., 1999, 32, HELX97, release 97-2 (Programs for Crystal tructure Analysis). G. M. heldrick, nstitüt für Anorganische Chemie der Universität, Tammanstrasse 4, D-3400 Göttingen, Germany, L. J. Farrugia, J. Appl. Crystallogr., 1999, 32, L. J. Farrugia, J. Appl. Crystallogr., 1997, 30,
3 MR data Methyl 3-benzoylaminothiophene-2-carboxylate. 1 H MR (CDCl 3, 300 MHz): δ 3.88 (s, 3H), 7.51 (m, 4H), 7.99 (m, 2H), 8.27 (d, 1H, J = 5.4 Hz), 11.1 (s, 1H); 13 C MR (CDCl 3, 75 MHz): δ 52.1, 110.4, 122.3, 127.4, 128.9, 131.9, 132.3, 133.6, 145.2, 164.1, Phenyl-3H-thieno[3,2-d]pyrimidin-4-one. 1 H MR ((CD 3 ) 2 O, 300 MHz): δ 7.48 (d, 1H, J = 5.2 Hz), 7.57 (m, 3H), 8.13 (m, 2H), 8.22 (d, 1H, J = 5.2 Hz), 12.7 (br s, 1H); 13 C MR ((CD 3 ) 2 O, 75 MHz): δ 121.2, 125.4, 127.8, 128.6, 131.3, 132.5, 135.4, 154.3, 157.9, Chloro-2-phenylthieno[3,2-d]pyrimidine (2). 1 H MR (CDCl 3, 300 MHz): δ 7.51 (m, 3H), 7.62 (d, 1H, J = 5.5 Hz), 2 (d, 1H, J = 5.2 Hz), 8.52 (m, 2H); 13 C MR (CDCl 3, 75 MHz): δ 125.2, 128.3, 128.5, 128.7, 130.9, 136.7, 136.8, 154.9, 161.7, Chloro-2-phenylthieno[2,3-d]pyrimidine (3). 1 H MR (CDCl 3, 300 MHz): δ 7.42 (d, 1H, J = Hz), 7. (m, 3H), 7.54 (d, 1H, J = Hz), 8.52 (m, 2H); 13 C MR (CDCl 3, 75 MHz): δ 119.9, 127.4, 127.5, 128.6, 128.7, 131.1, 136.3, 155.1, 160.0, Methoxythieno[2,3-d]pyrimidine (4). 1 H MR (CDCl 3, 300 MHz): δ 4.12 (s, 3H), 7.35 (d, 1H, J = Hz), 7.37 (d, 1H, J = Hz), 8.64 (s, 1H); 13 C MR (CDCl 3, 75 MHz): δ 54.1, 118.6, 119.2, 124.8, 153.4, 164.3, Methoxy-2-phenylthieno[2,3-d]pyrimidine (6). 1 H MR (CDCl 3, 300 MHz): δ 4.22 (s, 3H), 7.31 (d, 1H, J = Hz), 7.35 (d, 1H, J = Hz), 7. (m, 3H), 8.55 (m, 2H); 13 C MR (CDCl 3, 75 MHz): δ 53.6, 117.1, 118.5, 124.1, 128.3, 128.4, 130.3, 137.5, 159.7, 163.8, (Pyrazol-1-yl)thieno[2,3-d]pyrimidine (5). 1 H MR (CDCl 3, 300 MHz): δ 7.26 (s, 1H), 8.26 (d, 1H, J = Hz), 8.59 (s, 1H), 9.15 (d, 1H, J = Hz), 9. (d, 1H, J = 2.7 Hz), 9.57 (s, 1H); 13 C MR (CDCl 3, 75 MHz): δ 108.7, 119.2, 123.4, 126.4, 129.0, 144.3, 151.0, 152.4, (Morpholin-4-yl)-2-phenylthieno[2,3-d]pyrimidine (7). 1 H MR (CDCl 3, 300 MHz): δ 3.88 (m, 4H), 3.97 (m, 4H), 7.24 (d, 1H, J = Hz), 7.31 (d, 1H, J = Hz), (m, 3H), 8.46 (m, 2H); 13 C MR (CDCl 3, 75 MHz): δ 47.3, 66.7, 114.9, 120.2, 121.9, 128.2, 128.3, 130.1, 13, 158.7, 158.8, Chloro-6-iodothieno[2,3-d]pyrimidine (8). 1 H MR (CDCl 3, 300 MHz): δ 7.70 (s, 1H), 7.80 (s, 1H); 13 C MR (CDCl 3, 75 MHz): δ 82.2, 129.4, 131.3, 152.7, 152.8, odo-4-methoxythieno[2,3-d]pyrimidine (9). 1 H MR (CDCl 3, 300 MHz): δ 4.10 (s, 3H), 7.60 (s, 1H), 8.56 (s, 1H); 13 C MR (CDCl 3, 75 MHz): δ 54.4, 77.2, 121.1, 128.5, 153.5, 162.4,
4 4-Chloro-6-iodo-2-phenylthieno[3,2-d]pyrimidine (10a). 1 H MR (CDCl 3, 300 MHz): δ 7.49 (m, 3H), 7.83 (s, 1H), 8.47 (m, 2H); 13 C MR (CDCl 3, 75 MHz): δ 92.2, 128.5, 128.7, 131.1, 133.3, 134.9, 136.3, 152.6, 162.0, Chloro-6-iodo-2-phenylthieno[2,3-d]pyrimidine (11). 1 H MR (CDCl 3, 300 MHz): δ 7. (m, 3H), 7.68 (s, 1H), 8.48 (m, 2H); 13 C MR (CDCl 3, 75 MHz): δ 80.9, 128.6, 128.7, 129.2, 129.5, 131.3, 135.9, 152.8, 159.9, Chloro-6,7-diiodo-2-phenylthieno[3,2-d]pyrimidine (10b). 1 H MR (CDCl 3, 300 MHz): δ 7.48 (m, 3H), 8.54 (m, 2H); 13 C MR (CDCl 3, 75 MHz): δ 98.7, 101.3, 128.7, 128.8, 131.4, 132.8, 135.9, 153.1, 162.0, odo-4-methoxy-2-phenylthieno[2,3-d]pyrimidine (12). 1 H MR (CDCl 3, 300 MHz): δ 4.21 (s, 3H), 7.48 (m, 3H), 7.60 (s, 1H), 8.49 (m, 2H); 13 C MR (CDCl 3, 75 MHz): δ 53.9, 76.1, 119.0, 128.4, 128.4, 128.5, 130.6, 137.2, 159.7, 162.1, odo-4-(morpholin-4-yl)-2-phenylthieno[2,3-d]pyrimidine (13). 1 H MR (CDCl 3, 300 MHz): δ 3.89 (t, 4H, J = 4.5 Hz), 0 (t, 4H, J = 4.3 Hz), 7.48 (m, 3H), 7.55 (s, 1H), 8.44 (m, 2H); 13 C MR (CDCl 3, 75 MHz): δ 46.5, 65.9, 76.1, 116.2, 127.7, 128.4, 130.3, 130.6, 13, 156.3, 157.3, (Morpholin-4-yl)-2-phenyl-6-(pyridin-2-yl)-thieno[2,3-d]pyrimidine (14). 1 H MR (CDCl 3, 300 MHz): δ 3.93 (m, 4H), 6 (m, 4H), 7.23 (ddd, 1H, J = 2.0, 4.9 and Hz), 7.48 (m, 3H), 7.73 (m, 2H), 7.88 (s, 1H), 8.47 (m, 2H), 8.64 (dt, 1H, J = 1.2 and 4.6 Hz); 13 C MR (CDCl 3, 75 MHz): δ 47.3, 66.8, 116.2, 117.5, 119.6, 122.7, 128.3, 128.3, 130.2, 136.8, 13, 139.3, 149.8, 151.8, 158.7, 159.3, ()-3-Phenyl-2-(2-phenylthieno[3,2-d]pyrimidin-4-ylamino)propanoic acid (15). 1 H MR ((CD 3 ) 2 O, 300 MHz): δ 3.34 (AB part of an ABX system, 2H, J AX = 3.7 Hz, J BX = 8.9 Hz and J AB = 13.6 Hz), 4.99 (m, 1H), 6 (t, 1H, J = Hz), 7.15 (t, 2H, J = 7.2 Hz), 7.29 (d, 2H, J = 7.2 Hz), 7.44 (m, 4H), 7.76 (br s, 1H), 6 (d, 1H, J = 5.3 Hz), 8.39 (m, 2H); 13 C MR ((CD 3 ) 2 O, 75 MHz): δ 3, 56.3, 113.4, 124.6, 125.8, 127.7, 127.8, 128.1, 129.2, 129.7, 132.9, 138.4, 139.1, 156.5, 159.5, 160.2, ()-2-(6-odo-2-phenylthieno[3,2-d]pyrimidin-4-ylamino)-3-phenylpropanoic acid (16). 1 H MR ((CD 3 ) 2 O, 300 MHz): δ 3.26 (AB part of an ABX system, 2H, J AX = Hz, J BX = 9.9 Hz and J AB = 13.6 Hz), 4.90 (m, 1H), 7.10 (t, 1H, J = 7.2 Hz), 7.18 (t, 2H, J =7.3 Hz), 7.31 (d, 2H, J = 7.2 Hz), 7.43 (m, 3H), 7.71 (s, 1H), 8.10 (br s, 1H), 8.33 (m, 2H); 13 C MR ((CD 3 ) 2 O, 75 MHz): δ 36.7, 56.3, 89.3, 118.3, 12, 127.7, 12, 128.2, 129.1, 129.9, 133.9, 137.9, 138.8, 15, 159.7, 160.9, ()-2-(6,7-Diiodo-2-phenylthieno[3,2-d]pyrimidin-4-ylamino)-3-phenylpropanoic acid (17). 1 H MR ((CD 3 ) 2 O, 300 MHz): δ 3.20 (m, 2H), 4.85 (m, 1H), 7 (t, 1H, J = 7.2 Hz), 7.15 (t, 2H, J =7.3 3
5 Hz), 7.26 (br d, 2H, J = 7 Hz), 7.47 (m, 3H), 7.96 (br s, 1H), 8.40 (m, 2H); 13 C MR ((CD 3 ) 2 O, 75 MHz): δ 36.7, 56.3, 99.9, 103.7, 125.8, 127.8, 127.9, 128.2, 129.1, 129.4, 130.2, 137.7, 139.1, 159.6, 160.6, ()-3-Phenyl-2-(2-phenylthieno[2,3-d]pyrimidin-4-ylamino)propanoic acid (18). 1 H MR ((CD 3 ) 2 O, 300 MHz): δ 3.29 (AB part of an ABX system, 2H, J AX = 3.8 Hz, J BX = 10 Hz and J AB = 13.4 Hz), 3.71 (br s, 1H), 0 (m, 1H), 8 (t, 1H, J = 7.1 Hz), 7.17 (t, 2H, J =7.3 Hz), 7.33 (d, 2H, J = 7.3 HZ), 7.43 (m, 3H), 7.49 (d, 1H, J = 5.9 Hz), 7.71 (d, 1H, J = 5.9 Hz), 8.17 (d, 1H, J = Hz), 8.36 (m, 2H); 13 C MR ((CD 3 ) 2 O, 75 MHz): δ 37.1, 56.3, 114.8, 119.7, 122.3, 125.9, 127.7, 127.9, 128.2, 129.1, 129.9, 137.9, 139.0, 156.5, 158.5, ()-2-(6-odo-2-phenylthieno[2,3-d]pyrimidin-4-ylamino)-3-phenylpropanoic acid (19). 1 H MR ((CD 3 ) 2 O, 300 MHz): δ 3.23 (AB part of an ABX system, 2H, J AX = 4.5 Hz, J BX = 10.3 Hz and J AB = 13.7 Hz), 4.92 (m, 1H), 7.13 (t, 1H, J = 7.2 Hz), 7.23 (t, 2H, J =7.3 Hz), 7.35 (br d, 2H, J = 7.1 Hz), 7.43 (m, 3H), 6 (s, 1H), 8.30 (m, 3H); 13 C MR ((CD 3 ) 2 O, 75 MHz): δ 36.6, 55.9, 75.8, 116.7, 126.2, 127.8, 128.1, 128.3, 129.0, 129.1, 130.2, 137.4, 138.4, 154.9, 158.5, 170.7, ()-2-[(6-odo-2-phenylthieno[2,3-d]pyrimidin-4-yl)(methyl)amino]-3-phenylpropanoic acid (20). 1 H MR (CDCl 3, 300 MHz): δ 3.12 (s, 3H), 3.40 (AB part of an ABX system, 2H, J AX = 4.4 Hz, J BX = 9.9 Hz and J AB = 14 Hz), 5.11 (br s, 1H), 7.14 (m, 5H), 7.39 (m, 4H), 8.28 (br d, 2H); 13 C MR (CDCl 3, 75 MHz): δ 29.7, 34.6, 73.2, 116.6, 126.8, 128.2, 128.4, 128.6, 128.9, 130.4, 130.7, 136.9, 13, 137.4, 15, 158.1, ()-2-(6-odo-2-phenylthieno[2,3-d]pyrimidin-4-ylamino)-3-phenylpropan-1-ol (21). 1 H MR ((CD 3 ) 2 O, 300 MHz): δ 2.98 (AB part of an ABX system, 2H, J AX = 5.4 Hz, J BX = 8.5 Hz and J AB = 13.7 Hz), 3.60 (m, 2H), 4.66 (m, 1H), 4.93 (t, 1H, J = 5.6 Hz), 7.11 (tt, 1H, J = 7.2 Hz and 1.3 Hz), 7.23 (t, 2H, 7.4 Hz), 7.32 (m, 2H), 7.47 (m, 3H), 7.77 (d, 1H, J = 8.1 Hz), 7 (s, 1H), 8.33 (m, 2H); 13 C MR ((CD 3 ) 2 O, 75 MHz): δ 36.6, 5, 62.2, 7, 116.7, 125.9, 127.7, 127.8, 128.1, 128.3, 128.7, 129.1, 129.3, 130.1, 130.8, 131.7, 137.7, 139.3, 155.1, 158.7, ()-1-(6-odo-2-phenylthieno[2,3-d]pyrimidin-4-yl)pyrrolidine-2-carboxylic acid (22). 1 H MR ((CD 3 ) 2 O, 300 MHz): δ (m, 4H), 3.95 (m, 2H), 4.69 (m, 1H), 7.41 (m, 3H), 7.80 (s, 1H), 8.31 (m, 2H); 13 C MR ((CD 3 ) 2 O, 75 MHz): δ 21.1, 24.7, 24.8, 28.4, 31.1, 49.3, 61.5, 63.1, 74.7, 11, 127.8, 128.3, 130.3, 130.6, 137.2, 157.6, 17. 4
6 Copies of MR spectra H - CDCl MHz CO 2 Me H O Ph C - CDCl 3-75 MHz CO 2 Me H O Ph 5
7 H - (CD 3 ) 2 O MHz O H Ph C - (CD 3 ) 2 O - 75 MHz O H Ph 6
8 H - CDCl MHz Cl Ph C - CDCl 3-75 MHz Cl Ph 3 7
9 H - CDCl MHz O C - CDCl 3-75 MHz O 14 8
10 H - (CD 3 ) 2 O MHz H C - (CD 3 ) 2 O - 75 MHz H 15 9
11 H - (CD 3 ) 2 O MHz H C - (CD 3 ) 2 O - 75 MHz H 16 10
12 H - (CD 3 ) 2 O MHz H C - (CD 3 ) 2 O - 75 MHz H 17 11
13 H - (CD 3 ) 2 O MHz H C - (CD 3 ) 2 O - 75 MHz H 18 12
14 H - (CD 3 ) 2 O MHz H C - (CD 3 ) 2 O - 75 MHz H 19 13
15 H - CDCl MHz CO 2 H C - CDCl 3-75 MHz CO 2 H 20 14
16 H - (CD 3 ) 2 O MHz H OH C - (CD 3 ) 2 O - 75 MHz H OH 21 15
17 H - (CD 3 ) 2 O MHz C - (CD 3 ) 2 O - 75 MHz 22 16
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