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Synthesis and cytotoxicity of dinuclear platinum(Ⅱ) complexes of (1S, 3S)-1, 2, 3, 4-tetrahydroisoquinolines

Geng Xu ,  Ju Guo ,  Zheng Yan ,  Nan Wang ,  Zhan-Zhu Liu

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Citation:  Geng Xu, Ju Guo, Zheng Yan, Nan Wang, Zhan-Zhu Liu. Synthesis and cytotoxicity of dinuclear platinum(Ⅱ) complexes of (1S, 3S)-1, 2, 3, 4-tetrahydroisoquinolines[J]. Chinese Chemical Letters, 2013, 24(3): 186-188. shu

Synthesis and cytotoxicity of dinuclear platinum(Ⅱ) complexes of (1S, 3S)-1, 2, 3, 4-tetrahydroisoquinolines

    • 通讯作者: Zhan-Zhu Liu,
摘要: A series of novel dinuclear platinum(Ⅱ) complexes with (1S, 3S)-1,2,3,4-tetrahydroisoquinolines as the ligands were synthesized as potential anticancer agents in several steps starting from commercially available L-DOPA. The cytotoxicities of the series of dinuclear platinum(Ⅱ) complexes of tetrahydroisoquinoline were tested against HCT-8, BEL-7402, A2780, MCF-7, Hela, A549 and BGC-823 cell lines by the MTT test. These complexes showed selective inhibition activity against cisplatin-insensitive cell line Skov3.

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    19. [14] Data of ligands 7a-e. 7a: White solid, mp > 250℃, [α]D24-33.3 (c 0.81 CH3OH) 1H NMR (300 MHz, DMSO-d6): δ 1.38 (s, 4H, C-C2H4-C), 1.71 (s, 4H, C-CH2-C×2), 2.90-3.10 (m, 6H, CH2-Ar×2), 3.20-3.30 (m, 2H, CH2-N×2), 3.44 (s, 6H, -OCH3×2), 3.78 (s, 6H, -OCH3×2), 4.10 (m, 2H, CH-Ar×2), 5.74 (d, 2H, J = 6.6, Ar-CH-Ar×2), 6.07 (s, 2H, Ar-H×2), 6.85 (s, 2H, Ar-H×2), 7.50 (s, 10H, Ar-H×2), 9.58 (br, 4H, -NH×2), 10.07 (br, 2H, -NH×2), 10.27 (br, 2H, -NH×2). ESI-MS: 679 (m/z + 1); HRMS (ESI) Calcd. for C42H55N4O4: 679.4217, found: 679.4224. 7b: White solid, mp 190-192℃, [α]D24- -35.2 (c 0.31 CH3OH) 1H NMR (300 M Hz, DMSO-d6): δ 1.35 (s, 6H, C-C3H6-C), 1.70 (s, 4H, C-CH2-C×2), 2.90-3.10 (m, 6H, CH2-Ar×2), 3.20-3.30 (m, 2H, CH2-N×2), 3.44 (s, 6H, -OCH3×2), 3.78 (s, 6H, -OCH3×2), 4.10 (m, 2H, CH-Ar×2), 5.72 (m, 2H, Ar-CH-Ar×2), 6.07 (s, 2H, Ar-H×2), 6.85 (s, 2H, Ar-H×2), 7.49 (m, 10H, Ar-H×2), 9.65 (br, 4H, -NH×2), 10.17 (br, 2H, -NH×2), 10.33 (br, 2H, -NH×2). ESI-MS: 693 (m/z + 1); HRMS (ESI) Calcd. for C43H57N4O4: 693.4374, found: 693.4365. 7c: White solid, mp 237-239℃, [α]D24-34.7 (c 0.39 CH3OH) 1H NMR (300 MHz, DMSO-d6): δ 1.32 (s, 8H, C-C4H8-C), 1.68 (m, 4H, C-CH2-C×2), 2.90-3.10 (m, 4H, CH2-Ar×2), 3.20-3.30 (m, 8H, CH2-N-CH2×2), 3.44 (s, 6H, -OCH3×2), 3.78 (s, 6H, -OCH3×2), 4.09 (m, 2H, N-CH-C×2), 5.72 (m, 2H, Ar-CH-Ar×2), 6.07 (s, 2H, Ar-H×2), 6.85 (s, 2H, Ar-H×2), 7.49 (m, 10H, Ar-H×2), 9.62 (br, 4H, -NH×2), 10.10 (br, 2H, -NH×2), 10.33 (br, 2H, -NH×2). 13C NMR (75 MHz, DMSO-d6): δ 148.64, 147.52, 136.17, 130.19, 129.47, 128.65, 124.13, 123.51, 111.41, 110.54, 60.63, 55.57, 55.46, 51.54, 48.09, 47.16, 29.19, 28.04, 25.66, 25.26. ESI-MS: 707 (m/z + 1); HRMS (ESI) Calcd. for C44H59N4O4: 707.4536, found: 707.4553. 7d: Yellowish solid, mp 185-187℃, [α]D24-27.9 (c 0.57 CH3OH) 1H NMR (300 MHz, DMSO-d6): δ 1.28 (s, 10H, C-C5H10-C), 1.65 (m, 4H, C-CH2-C×2), 2.90-3.10 (m, 6H, CH2-Ar×2), 3.20-3.30 (m, 2H, CH2-N×2), 3.35 (s, 6H, -OCH3×2), 3.77 (s, 6H, -OCH3×2), 4.09 (m, 2H, CH-Ar×2), 5.71 (m, 2H, Ar-CH-Ar×2), 6.06 (s, 2H, Ar-H×2), 6.83 (s, 2H, Ar-H×2), 7.48 (m, 10H, Ar-H×2), 9.63 (br, 4H, -NH×2), 10.15 (br, 2H, -NH×2), 10.32 (br, 2H, -NH×2). ESI-MS: 721 (m/z + 1); HRMS (ESI) Calcd. for C45H61N4O4: 721.4687, found: 721.4692. 7e: Yellowish solid, mp 209-211℃, [α]D24-30.9 (c 0.58 CH3OH) 1H NMR (300 MHz, DMSO-d6): δ 1.27 (s, 16H, C-C8H16-C), 1.66 (m, 4H, C-CH2-C×2), 2.90-3.10 (m, 6H, CH2-Ar×2), 3.20-3.30 (m, 2H, CH2-N×2), 3.44 (s, 6H, -OCH3×2), 3.78 (s, 6H, -OCH3×2), 4.09 (m, 2H, CH-Ar×2), 5.73 (m, 2H, Ar-CH-Ar×2), 6.07 (s, 2H, Ar-H×2), 6.85 (s, 2H, Ar-H×2), 7.49 (m, 10H, Ar-H×2), 9.61 (br, 4H, -NH×2), 10.14 (br, 2H, -NH×2), 10.32 (br, 2H, -NH×2). ESI-MS: 764 (m/z + 1); HRMS (ESI) Calcd. for C48H67N4O4: 763.5156, found: 763.5155.[14] Data of ligands 7a-e. 7a: White solid, mp > 250℃, [α]D24-33.3 (c 0.81 CH3OH) 1H NMR (300 MHz, DMSO-d6): δ 1.38 (s, 4H, C-C2H4-C), 1.71 (s, 4H, C-CH2-C×2), 2.90-3.10 (m, 6H, CH2-Ar×2), 3.20-3.30 (m, 2H, CH2-N×2), 3.44 (s, 6H, -OCH3×2), 3.78 (s, 6H, -OCH3×2), 4.10 (m, 2H, CH-Ar×2), 5.74 (d, 2H, J = 6.6, Ar-CH-Ar×2), 6.07 (s, 2H, Ar-H×2), 6.85 (s, 2H, Ar-H×2), 7.50 (s, 10H, Ar-H×2), 9.58 (br, 4H, -NH×2), 10.07 (br, 2H, -NH×2), 10.27 (br, 2H, -NH×2). ESI-MS: 679 (m/z + 1); HRMS (ESI) Calcd. for C42H55N4O4: 679.4217, found: 679.4224. 7b: White solid, mp 190-192℃, [α]D24- -35.2 (c 0.31 CH3OH) 1H NMR (300 M Hz, DMSO-d6): δ 1.35 (s, 6H, C-C3H6-C), 1.70 (s, 4H, C-CH2-C×2), 2.90-3.10 (m, 6H, CH2-Ar×2), 3.20-3.30 (m, 2H, CH2-N×2), 3.44 (s, 6H, -OCH3×2), 3.78 (s, 6H, -OCH3×2), 4.10 (m, 2H, CH-Ar×2), 5.72 (m, 2H, Ar-CH-Ar×2), 6.07 (s, 2H, Ar-H×2), 6.85 (s, 2H, Ar-H×2), 7.49 (m, 10H, Ar-H×2), 9.65 (br, 4H, -NH×2), 10.17 (br, 2H, -NH×2), 10.33 (br, 2H, -NH×2). ESI-MS: 693 (m/z + 1); HRMS (ESI) Calcd. for C43H57N4O4: 693.4374, found: 693.4365. 7c: White solid, mp 237-239℃, [α]D24-34.7 (c 0.39 CH3OH) 1H NMR (300 MHz, DMSO-d6): δ 1.32 (s, 8H, C-C4H8-C), 1.68 (m, 4H, C-CH2-C×2), 2.90-3.10 (m, 4H, CH2-Ar×2), 3.20-3.30 (m, 8H, CH2-N-CH2×2), 3.44 (s, 6H, -OCH3×2), 3.78 (s, 6H, -OCH3×2), 4.09 (m, 2H, N-CH-C×2), 5.72 (m, 2H, Ar-CH-Ar×2), 6.07 (s, 2H, Ar-H×2), 6.85 (s, 2H, Ar-H×2), 7.49 (m, 10H, Ar-H×2), 9.62 (br, 4H, -NH×2), 10.10 (br, 2H, -NH×2), 10.33 (br, 2H, -NH×2). 13C NMR (75 MHz, DMSO-d6): δ 148.64, 147.52, 136.17, 130.19, 129.47, 128.65, 124.13, 123.51, 111.41, 110.54, 60.63, 55.57, 55.46, 51.54, 48.09, 47.16, 29.19, 28.04, 25.66, 25.26. ESI-MS: 707 (m/z + 1); HRMS (ESI) Calcd. for C44H59N4O4: 707.4536, found: 707.4553. 7d: Yellowish solid, mp 185-187℃, [α]D24-27.9 (c 0.57 CH3OH) 1H NMR (300 MHz, DMSO-d6): δ 1.28 (s, 10H, C-C5H10-C), 1.65 (m, 4H, C-CH2-C×2), 2.90-3.10 (m, 6H, CH2-Ar×2), 3.20-3.30 (m, 2H, CH2-N×2), 3.35 (s, 6H, -OCH3×2), 3.77 (s, 6H, -OCH3×2), 4.09 (m, 2H, CH-Ar×2), 5.71 (m, 2H, Ar-CH-Ar×2), 6.06 (s, 2H, Ar-H×2), 6.83 (s, 2H, Ar-H×2), 7.48 (m, 10H, Ar-H×2), 9.63 (br, 4H, -NH×2), 10.15 (br, 2H, -NH×2), 10.32 (br, 2H, -NH×2). ESI-MS: 721 (m/z + 1); HRMS (ESI) Calcd. for C45H61N4O4: 721.4687, found: 721.4692. 7e: Yellowish solid, mp 209-211℃, [α]D24-30.9 (c 0.58 CH3OH) 1H NMR (300 MHz, DMSO-d6): δ 1.27 (s, 16H, C-C8H16-C), 1.66 (m, 4H, C-CH2-C×2), 2.90-3.10 (m, 6H, CH2-Ar×2), 3.20-3.30 (m, 2H, CH2-N×2), 3.44 (s, 6H, -OCH3×2), 3.78 (s, 6H, -OCH3×2), 4.09 (m, 2H, CH-Ar×2), 5.73 (m, 2H, Ar-CH-Ar×2), 6.07 (s, 2H, Ar-H×2), 6.85 (s, 2H, Ar-H×2), 7.49 (m, 10H, Ar-H×2), 9.61 (br, 4H, -NH×2), 10.14 (br, 2H, -NH×2), 10.32 (br, 2H, -NH×2). ESI-MS: 764 (m/z + 1); HRMS (ESI) Calcd. for C48H67N4O4: 763.5156, found: 763.5155.

    20. [15] General procedure for the preparation of compound 8a-e: A solution of 7c (1.0 mmol) and K2PtC14 (2.0 mmol) in distilled water (12 mL) was heated to 65-70℃ with stirring. The pH of the reaction solution was checked continuously and 1 mol/L NaOH was added to keep the pH in the range 3-4. Toward the end of the reaction, pH was adjusted to 6 with 0.1 mol/L NaOH. After the mixture was cooled to ambient temperature, the precipitate was filtered, washed three times with cold water, twice with ethanol, and once with diethyl ether, and dried in vacuo (87% yield) to afford compound 8c: yellow solid, mp: 237-239℃, Elemental analysis: Calcd. for C44H58O4N4Cl4Pt2 (%): C 42.66, H 4.72, N 4.52; Found: C 42.59, H 4.92, N 4.36. 8a: Offwhite solid, mp: 237-239℃, Elemental analysis: Calcd. for C42H54O4N4Cl4Pt2 (%): C 41.65, H 4.49, N 4.63; Found: C 41.79, H 4.52, N 4.61. 8b: Offwhite solid, mp: 234-236℃, Elemental analysis: Calcd. for C43H56O4N4Cl4Pt2 (%): C 42.16, H 4.61, N 4.57; Found: C 42.57, H 4.81, N 4.40. 8d: Offwhite solid, mp: 238-240℃, Elemental analysis: Calcd. for C45H60O4N4Cl4Pt2 (%): C 43.14, H 4.83, N 4.47; Found: C 43.30, H 4.68, N 4.64. 8e: Offwhite solid, mp: 228-230℃, Elemental analysis: Calcd. for C48H60O4N4Cl4Pt2 (%): C 44.52, H 5.14, N 4.33; Found: C 44.30, H 5.27, N 4.16.[15] General procedure for the preparation of compound 8a-e: A solution of 7c (1.0 mmol) and K2PtC14 (2.0 mmol) in distilled water (12 mL) was heated to 65-70℃ with stirring. The pH of the reaction solution was checked continuously and 1 mol/L NaOH was added to keep the pH in the range 3-4. Toward the end of the reaction, pH was adjusted to 6 with 0.1 mol/L NaOH. After the mixture was cooled to ambient temperature, the precipitate was filtered, washed three times with cold water, twice with ethanol, and once with diethyl ether, and dried in vacuo (87% yield) to afford compound 8c: yellow solid, mp: 237-239℃, Elemental analysis: Calcd. for C44H58O4N4Cl4Pt2 (%): C 42.66, H 4.72, N 4.52; Found: C 42.59, H 4.92, N 4.36. 8a: Offwhite solid, mp: 237-239℃, Elemental analysis: Calcd. for C42H54O4N4Cl4Pt2 (%): C 41.65, H 4.49, N 4.63; Found: C 41.79, H 4.52, N 4.61. 8b: Offwhite solid, mp: 234-236℃, Elemental analysis: Calcd. for C43H56O4N4Cl4Pt2 (%): C 42.16, H 4.61, N 4.57; Found: C 42.57, H 4.81, N 4.40. 8d: Offwhite solid, mp: 238-240℃, Elemental analysis: Calcd. for C45H60O4N4Cl4Pt2 (%): C 43.14, H 4.83, N 4.47; Found: C 43.30, H 4.68, N 4.64. 8e: Offwhite solid, mp: 228-230℃, Elemental analysis: Calcd. for C48H60O4N4Cl4Pt2 (%): C 44.52, H 5.14, N 4.33; Found: C 44.30, H 5.27, N 4.16.

    21. [16] E. Schuhmann, J. Altman, K. Karaghiosoff, W. Beck, Bis[platinum(Ⅱ)] and bis[palladium( Ⅱ)] complexes of a,v-dicarboxylic acid bis(1,2,4-triaminobutane-N4) amides, Inorg. Chem. 34 (1995) 2316-2322.[16] E. Schuhmann, J. Altman, K. Karaghiosoff, W. Beck, Bis[platinum(Ⅱ)] and bis[palladium( Ⅱ)] complexes of a,v-dicarboxylic acid bis(1,2,4-triaminobutane-N4) amides, Inorg. Chem. 34 (1995) 2316-2322.

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  • 收稿日期:  2012-12-21
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