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Dalton Transactions
Page 12 of 15
ARTICLE
Journal Name
action of the drug, due to unavoidable conformational [CuCl2L4] (4) Yield: 0.24 g, 52%. Anal.ViewcaArltcicdle Onflioner
modifications in the drug target. In future work, we will study C21H15Cl2N3OCu·H2O: C, 52.79; H, 3.59;DONI,: 180..17093%9/.D0FDoTu0n3d9:89CF
the antitumor activity of other metal complexes of the 52.37, H 3.20, N 8.43%. IR (KBr, cm−1): 3437 (m, νO–H), 3071 (m,
substituted terpyridine ligands and screen out the metal νC–H), 1603 (s, νC=C), 1554 (m, νC=C), 1475 (s, νC=C), 1418 (s, νC=C),
complexes, including Mn, Fe, Co, Ni, Ru, Pd, Ag, Pt and Au and 1289 (m, βC–H), 1248 (m, βC–H), 1218 (m, βC–H), 1168 (w, βC–H),
their formate, acetate, nitrate, chloride and/or benzoate salts, 1034 (m, βC–H), 1020 (s, βC–H), 867 (m, γC–H), 783 (s, γC–H), 726 (m,
as anticancer reagents with high efficacy, good bioavailability γC–H), 695 (m, γC–H), 653 (m), 632 (m). Mol. conductivity 35.10
and weak cross-resistance, to establish the structure-activity μS. Slow evaporation of its EtOH/DCM solution led to the
relationship through in vitro and in vivo studies and mechanism formation of green crystals that were suitable for X-ray analysis.
research work.
[CuCl2L5] (5) Yield: 0.23 g, 50%. Anal. calcd for
C21H15Cl2N3OCu·0.5H2O: C, 53.80; H, 3.44; N, 8.96%. Found: C
53.85, H 3.12, N 9.04%. IR (KBr, cm−1): 3467(m, νO–H), 3003 (m,
νC–H), 1601 (s, νC=C), 1568 (m, νC=C), 1549 (m, νC=C), 1475 (s, νC=C),
1415 (s, νC=C), 1365 (m), 1315 (m), 1304 (m), 1286 (m), 1277 (m),
1242 (s, βC–H), 1162 (s, βC–H), 1126 (w, βC–H), 1017 (s, βC–H), 899
(m, γC–H), 861 (m, γC–H), 794 (s, γC–H), 772 (s, γC–H), 755 (m, γC–H),
729 (s, γC–H), 691 (w, γC–H), 658 (m), 646 (m), 624 (m), 558 (w).
Mol. conductivity 26.70 μS. Slow evaporation of its MeOH/DCM
solution led to the formation of green crystals that were
suitable for X-ray analysis.
4 Experimental
4.1 Chemicals and Reagents.
All of the chemicals and solvents were analytically pure and
used without further purification, unless specially noted.
[CuCl2L6] (6)
Yield: 0.32 g, 68%. Anal. calcd for C22H17Cl2N3OCu·2H2O: C,
51.82; H, 4.15; N, 8.24%. Found: C 51.62, H 3.89, N 8.19%. IR
(KBr, cm−1): 3063 (m, νC–H), 2895 (w, νC–H), 1601 (s, νC=C), 1587 (s,
νC=C), 1557 (m, νC=C), 1523 (m, νC=C), 1474 (m, δC–H), 1415 (m,
νC=C), 1369 (m, δC–H), 1279 (m, βC–H), 1236 (m, νC–O–C), 1182 (m,
βC–H), 1165 (m, βC–H), 1065 (w, γC–H), 1029 (m, γC–H), 1019 (m, γC–
H), 839 (s, γC–H), 791 (s, γC–H), 752 (m, γC–H), 727 (m, γC–H), 709 (m,
γC–H), 659 (m), 646 (m) and 585 (m). Mol. conductivity 18.45 μS.
[CuCl2L7] (7) Yield: 0.27 g, 47%. Anal. calcd for
C21H14Cl2IN3Cu·2H2O: C, 41.64; H, 3.00; N, 6.94%. Found: C
41.31, H 2.67, N 7.03%. IR (KBr, cm−1): 2988 (m, νC–H), 2900 (m,
νC–H), 1609 (m, νC=C), 1584 (w, νC=C), 1569 (w, νC=C), 1556 (w, νC=C),
1474 (m, νC=C), 1429 (m, νC=C), 1392 (m), 1249 (m, βC–H), 1160 (m,
βC–H), 1062 (m, βC–H), 1019 (m, βC–H), 1002 (m, βC–H), 899 (m, γC–
H), 828 (m, γC–H), 788 (s, γC–H), 750 (m, γC–H), 726 (m, γC–H), 700
(m, γC–H), 657 (m), 646 (m) and 559(m, νC–I). Mol. conductivity
19.42 μS. Slow evaporation of its MeOH/DCM solution led to
the formation of bluish-green crystals that were suitable for X-
ray analysis.
[CuCl2L8] (8) Yield: 0.29 g, 55%. Anal. calcd for
C21H14Cl2BrN3Cu·0.5H2O: C, 47.44; H, 2.84; N, 7.90%. Found: C
47.43, H 2.48, N 7.80%. IR (KBr, cm−1): 2988 (m, νC–H), 2900 (m,
νC–H), 1608 (m, νC=C), 1569 (w, νC=C), 1554 (m, νC=C), 1474 (s, νC=C),
1431 (m, νC=C), 1393 (m), 1251 (m, βC–H), 1160 (m, βC–H), 1077
(m, βC–H), 1065 (m, βC–H), 1018 (s, βC–H), 1004 (s, βC–H), 898 (m,
γC–H), 831 (m, γC–H), 793 (s, γC–H), 785 (m, γC–H), 748 (m, γC–H), 727
(m, γC–H), 670, 656 (m, νC–Br) and 645 (m). Mol. conductivity
21.80 μS.
4.2 Physical measurements.
The IR spectra were obtained with
a Nicolet iS10
spectrophotometer (Thermo Scientific). Elemental analyses (C,
H, N) were performed on a Perkin-Elmer 2400 series II analyser
or an Elementar vario EL cube.
4.3 Synthesis of the compounds.
For compounds 1–11, the dichloromethane solutions of the
corresponding ligands were added dropwise to the methanol
solutions of CuCl2 and the system was stirred for 24 h. Filtration
led to the separation of the powders of the compounds from
the mother solution, which was dried in a desiccator.
[CuCl2L2] (2) Yield: 0.21 g, 45%. Anal. calcd for
C22H14Cl2N4Cu·H2O·CH2Cl2: C, 48.31; H, 3.17; N, 9.80%. Found: C
48.18, H 3.18, N 10.18%. IR (KBr, cm−1): 3054 (m, νC–H), 2228 (m,
νC≡N), 1602 (s, νC=C), 1551 (m, νC=C), 1474 (s, νC=C), 1430 (m, νC=C),
1402 (s), 1249 (m, βC–H), 1163 (w, βC–H), 1097 (w, βC–H), 1021 (s,
βC–H), 1008 (m, βC–H), 898 (w, γC–H), 840 (m, γC–H), 788 (s, γC–H),
747 (m, γC–H), 724 (m, γC–H), 688 (m, γC–H), 657 (m), 648 (w), 545
(s). Mol. conductivity 34.30 μS. Slow evaporation of its
MeOH/DCM solution led to the formation of green crystals that
were suitable for X-ray analysis.
[CuCl2L3] (3) Yield: 0.26 g, 57%. Anal. calcd for
C21H15Cl2N3OCu·H2O: C, 52.79; H, 3.59; N, 8.79%. Found: C
52.47, H 3.27, N 9.01%. IR (KBr, cm−1): 3447(m, νO–H), 3064 (m,
νC–H), 1601 (s, νC=C), 1589 (s, νC=C), 1557 (m, νC=C), 1523 (m, νC=C),
1474 (s, νC=C), 1415 (s, νC=C), 1368, 1279 (m, βC–H), 1237 (s, βC–H),
1182 (m, βC–H), 1165 (s, βC–H), 1116 (w, βC–H), 1065 (w, βC–H),
1029 (m, βC–H), 1020 (s, βC–H), 901 (w, γC–H), 885 (m, γC–H), 839 (s,
γC–H), 790 (s, γC–H), 752 (m, γC–H), 727 (m, γC–H), 709 (m, γC–H), 659
(m), 646 (m), 585 (s). Mol. conductivity 12.31 μS. Slow
evaporation of its MeOH/DCM solution led to the formation of
green crystals that were suitable for X-ray analysis.
[CuCl2L9] (9) Yield: 0.27 g, 56%. Anal. calcd for
C21H14Cl3N3Cu·H2O: C, 50.82; H, 3.25; N, 8.47%. Found: C 51.02,
H 2.96, N 8.28%. IR (KBr, cm−1): 2987 (m, νC–H), 2901 (m, νC–H),
1602 (s, νC=C), 1555 (m, νC=C), 1475 (s, νC=C), 1432 (m, νC=C), 1397
(m), 1250 (m, βC–H), 1160 (m, βC–H), 1066 (m, βC–H), 1018 (s, βC–
H), 1007 (s, βC–H), 898 (m, γC–H), 835 (m, γC–H), 793 (s, γC–H), 749
(m, γC–H), 728 (s, νC–Cl), 656 (m), 645 (m) and 559 (m). Mol.
conductivity 24.20 μS.
12 | J. Name., 2012, 00, 1-3
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