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A kind of aromatic hydrocarbon ruthenium complex and its preparation method and application

A technology of ruthenium complexes and aromatic hydrocarbons, applied in ruthenium organic compounds, chemical instruments and methods, platinum group organic compounds, etc., to achieve good anti-tumor effects

Active Publication Date: 2020-05-05
GUANGDONG PHARMA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This type of compound has good activity against A2780 human ovarian cancer in vitro, but has no cross-resistance

Method used

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  • A kind of aromatic hydrocarbon ruthenium complex and its preparation method and application
  • A kind of aromatic hydrocarbon ruthenium complex and its preparation method and application
  • A kind of aromatic hydrocarbon ruthenium complex and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0105] [(η 6 -p-cymene)RuCl] 2 Cl 2 preparation of

[0106] RuCl 3 With 1-methyl-4-isopropyl-1,3-cyclohexadiene, at 50°C, microwave radiation for 30min, suction filtration, to obtain [(η 6 -p-cymene)RuCl] 2 Cl 2 .

Embodiment 2

[0108] [(η 6 Synthesis of -p-cymene)Ru(o-ClPIP)Cl]Cl (No. RAP051):

[0109] Get the phellandrene precursor that embodiment 1 obtains [(η 6 -p-cymene)RuCl] 2 Cl 2 (0.1mmol, 61.2mg), ligand o-ClPIP (0.2mmol, 66.1mg), at 60°C, microwave irradiation for 15s, to obtain 124.5mg of bright orange-yellow solid, which is [(η 6 -p-cymene)Ru(o-ClPIP)Cl]Cl(RAP051), yield 97.9%.

[0110] The ESI-MS spectrum of RAP051 is as follows Figure 1-Figure 3 Shown, ESI-MS (in MeOH, m / z): 636 (Cal.), 601 (Foundfor[M-Cl] + ), 565 (Found for [M-2Cl-H] + ). 1 H NMR (500MHz, DMSO-d 6 ( dd,J=23.2,8.0Hz,1H), 7.63–7.55(m,1H), 6.37(d,J=6.2Hz,1H), 6.13(d,J=6.2Hz,1H), 2.23(d,J =9.5Hz, 1H), 1.47–1.06(m, 1H), 0.91(d, J=6.9Hz, 3H). 13 C NMR (126MHz, DMSO-d 6 )δ154.24(s), 152.11–148.43(m), 143.64(s), 134.16–132.32(m), 131.98(s), 130.89(s), 130.55(d, J=85.9Hz), 127.95(s ), 126.70(s), 104.28(s), 103.57(s), 86.73(s), 84.38(s), 22.13(s), 18.77(s).

Embodiment 3

[0112] [(η 6 Synthesis of -p-cymene)Ru(PIP)Cl]Cl (No. RAP09):

[0113] Get the phellandrene precursor that embodiment 1 obtains [(η 6 -p-cymene)RuCl] 2 Cl 2 (0.1mmol, 61.2mg), ligand PIP (0.2mmol, 59.2mg), at 60°C, microwave irradiation for 30min, an orange-yellow solid was obtained, 113mg, yield 91.0%. ESI-MS (in MeOH, m / z) :592(Cal.),567(Found for[M-Cl] + ). 1 H NMR (500MHz, DMSO-d 6)δ9.85(d, J=5.2Hz, 1H), 9.45(s, 1H), 8.48(d, J=7.9Hz, 1H), 8.19(dd, J=8.1, 5.3Hz, 1H), 7.59( dd,J=20.7,13.2Hz,1H),7.55(dd,J=20.2,13.0Hz,1H),6.35(d,J=6.2Hz,1H),6.12(d,J=6.2Hz,1H), 2.82–2.52(m,1H),2.23(d,J=19.7Hz,2H),1.30–1.06(m,1H),0.89(t,J=15.6Hz,3H). 13 C NMR (126MHz, DMSO-d 6 )δ153.53(s), 143.02(s), 132.60(s), 130.03(s), 128.99(s), 126.74(s), 126.05(s), 103.79(s), 102.91(s), 86.19( s), 83.91(s), 73.23–27.78(m), 21.53(d, J=16.7Hz), 18.24(s).

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Abstract

The invention discloses an aromatic hydrocarbon ruthenium complex, which adopts R 1 R 2 R 3 PIP is the main ligand, the R 1 , R 2 , R 3 independently selected from ‑Cl, ‑F, ‑Br, ‑I, ‑CF 3 ,‑NO 2 ,‑OCH 3 ,‑OH,‑COOH,‑CH 3 ,‑N(CH 3 ) 2 ,‑C 2 h 2 ,‑SO 2 CH 3 , an alkyl group with 1 to 6 carbon atoms or a substituted alkyl group with 1 to 6 carbon atoms, pyridyl or substituted pyridyl, furyl or substituted furyl, pyrrolyl or substituted pyrrolyl, thiazole or substituted thiazolyl; Wherein, the substituents of the phenyl, pyridyl, furyl, and thiazole are all independently selected from hydroxyl, nitro, halogen, amino, carboxyl, cyano, mercapto, cycloalkyl with 3 to 8 carbon atoms, SO 3 H, an alkyl group with 1 to 6 carbon atoms, an alkenyl group with 2 to 6 carbon atoms, an alkynyl group with 2 to 6 carbon atoms, a hydroxyl group (C 1 -C 6 ) Alkyl, amino (C 1 -C 6 ) Alkyl, CO 2 R', CONR'R', COR', SO 2 R'R', (C 1 -C 6 ) alkoxy, (C 1 -C 6 ) alkylthio, -N=NR', NR'R' or trifluoro(C 1 -C 6 ) Any of the alkyl groups.

Description

technical field [0001] The invention relates to the technical field of synthetic chemistry, in particular to an arene ruthenium complex, and also relates to a preparation method and application of the arene ruthenium complex. Background technique [0002] The arene ruthenium complex has a classic "piano bench" spatial structure, and is a small covalent bond with the central metal ruthenium through electrons on the π orbital on the benzene ring, which use strongly hydrophobic benzene or substituted benzene as an auxiliary ligand. Molecular organometallic compounds. Since Winkhaus and Singer first synthesized arene ruthenium (II) compounds in 1967 [1], there have been a large number of literatures at home and abroad reporting the synthesis and antitumor effects of various types of arene ruthenium complexes. [0003] Kondapi et al. reported that [(η 6 -C 6 h 6 )Ru(DMSO)Cl 2 ] 2 + The representative aromatic hydrocarbon ruthenium complex exhibits good inhibitory effects o...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00A61P35/00A61P35/02
CPCC07F15/0053A61P35/00C07F15/0046
Inventor 梅文杰吴琼王成蹊
Owner GUANGDONG PHARMA UNIV
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