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Oxaccalix[4]arene derivatives and their applications

A technology for medicines and uses, applied in the field of p-tert-butyl monooxabicalix[4]arene compounds, which can solve the problems of few types of derivatization reactions, low yield of parent synthesis, and limited literature reports on aromatic hydrocarbons

Active Publication Date: 2020-04-03
XUZHOU MEDICAL COLLEGE
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] The literature reports on p-tert-butyl monooxabicalix[4]arenes are very limited, mainly due to the low synthesis yield of the parent material and fewer types of derivatization reactions. In addition, p-tert-butyl monooxabicalix[4]arene [4] Arene derivatives reported in the literature are mainly used for molecular ion recognition, and their pharmaceutical applications have not yet been carried out. Therefore, this study designed and synthesized amide-substituted p-tert-butyl monooxabihocalix[4]arene derivatives that have not been reported in the literature. to obtain oxacalixarene derivatives with novel structure and excellent water solubility; and select common tumor cells to conduct MTT or SRB experiments on the synthesized compounds to study whether the synthesized compounds have cytotoxicity and the strength of the effect on human cancer cells , from which compounds with anti-tumor activity and strong activity were screened

Method used

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  • Oxaccalix[4]arene derivatives and their applications
  • Oxaccalix[4]arene derivatives and their applications
  • Oxaccalix[4]arene derivatives and their applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Embodiment 1: the synthesis of compound 1a-1b

[0064]

[0065] 7,13,19,25-tetra-tert-butyl-28,30-dihydroxy-27,29-diethoxycarbonylmethoxymonoxabicalix[4]arene (compound 1, the same below) (1.0 mmol) and excess ethanolamine or diethanolamine (100% excess) were dissolved in ethanol and toluene mixed solution (1:1, 50mL) and refluxed for 72h. A small amount of distilled water was added to precipitate a solid, and the crude product was obtained by suction filtration, and the product 1a-1b was obtained by thin-layer chromatography.

[0066]

[0067] 1a: white solid, m.p.: 139.7-142.3℃, yield: 87.23%. 1 H NMR (CDCl 3 ,400MHz)δ1.03,1.20,1.26,1.29(4s,36H),3.44-3.53(m,5H),3.59-3.64(m,2H),3.79(s,4H),4.17-4.29(m,4H ),4.38(d,1H,J=10.2Hz),4.52-4.68(m,5H),4.84(d,1H,J=10Hz),6.85(d,1H,J=1.6Hz),6.92(d, 1H, J=2.4Hz), 7.02(d, 2H, J=2Hz), 7.16(d, 1H, J=2Hz), 7.21-7.24(m, 2H), 7.31(s, 1H), 7.38(d, 2H, J=2.4Hz), 8.78(d, 1H, J=0.4Hz), 8.84(s, 1H); 13 C NMR (CDCl 3 ,100MHz)δ31.0,3...

Embodiment 2

[0069] Embodiment 2: the synthesis of compound 1c-1e

[0070] 7,13,19,25-Tetra-tert-butyl-28,30-dihydroxy-27,29-diethoxycarbonylmethoxymonoxadiisocalix[4]arene 1 (1.0mmol) dissolved in 2- Aminomethylpyridine, 3-aminomethylpyridine or 4-aminomethylpyridine (2mL), heated to 70°C and reacted for 72h. After the reaction, add a small amount of distilled water to precipitate a solid. The product 1c-1e was obtained by analysis.

[0071]

[0072] 1c: light yellow solid, m.p.: 134.8-136.2℃, yield: 87.28%. 1 H NMR (CDCl 3 ,400MHz)δ1.091.22(2s,18H),1.25(d,18H,J=2Hz),3.35(t,2H,J=14.4Hz),4.08-4.21(m,3H),4.25-4.32(m, 2H), 4.50-4.52(m, 2H), 4.55-4.59(m, 2H), 4.62-4.69(m, 4H), 4.81-4.89(m, 3H), 6.81(d, 1H, J=2.4Hz) ,6.89(d,1H,J=2Hz),6.94-6.97(m,1H),7.00(d,1H,J=2.4Hz),7.01-7.04(m,1H),7.06(s,2H),7.13 (d,1H,J=2Hz),7.17(s,2H),7.31(d,1H,J=8Hz),7.37-7.41(m,2H),7.47-7.55(m,2H),7.80(s, 1H), 8.21(d, 1H, J=4.4Hz), 8.38(d, 1H, J=4.4Hz), 8.97(t, 1H), 9.22(t, 1H); 13 C NMR (CDCl 3 ,100MHz)δ31.0...

Embodiment 3

[0075] Embodiment 3: the synthesis of compound 1f-1g

[0076] 7,13,19,25-Tetra-tert-butyl-28,30-dihydroxy-27,29-diethoxycarbonylmethoxymonoxadiisocalix[4]arene 1 (1.0mmol) dissolved in butane In amine or hexamethylenediamine (2 mL), react at room temperature for 24 hours. After the reaction, a small amount of distilled water is added to precipitate a solid. The crude product is obtained by suction filtration, and the product 1f-1g is obtained by thin layer chromatography.

[0077]

[0078] 1f: white solid, m.p.: 129.4-131.2℃, yield: 96.18%. 1 H NMR (CDCl 3,400MHz)δ1.16(s,9H),1.25(t,27H),1.32(d,2H,J=11.2Hz),1.41(t,2H),1.45(d,3H,J=33.2Hz), 1.65(d,5H,J=62.0Hz),3.22(d,2H,J=33.2Hz),3.43(t,2H),3.60(d,2H,J=54.8Hz),4.10(d,1H,J =13.6Hz),4.19(t,2H),4.35(s,1H),4.39(t,2H),4.44(d,1H,J=9.2Hz),4.50(d,1H,J=11.2Hz), 4.58(d,1H,J=10.0Hz),4.77,4.83(dd,2H,J=14.8Hz),4.96(d,1H,J=10.4Hz),6.87(d,1H,J=2.4Hz), 7.01 (d, 1H, J = 2.4Hz), 7.04 (d, 1H, J = 2.0Hz), 7.14 (d, 1H, J = 2.4Hz), 7.16 (d, 1H...

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Abstract

The invention discloses a class of oxaccalix[4]arene derivatives and applications thereof. The derivatives are compounds represented by formula (I) or pharmaceutically acceptable salts thereof, compounds of the present invention or pharmaceutically acceptable salts thereof The salt of can be applied to the preparation of anticancer drugs, especially anti-lung cancer, anti-breast cancer, anti-cervical cancer or anti-liver cancer drugs.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a class of p-tert-butyl monooxabicalix[4]arene compounds with novel structures and the application of the compounds in medicine. Background technique [0002] Calixarene is a kind of cyclic oligomer obtained by condensation reaction of phenolic substances with aldehydes or ketones. It is named calixarene because its molecular shape resembles the Greek Holy Grail. Its history can be traced back to 1872 when German chemist A. Baeyer (ChemLife, 2002, 22 (3): 265-267) studied the heating reaction of phenol and formaldehyde aqueous solution. Because the synthesis method has many steps and low yield, so Failed to get people's attention. In the late 1970s, C.D.Gutsche (J.Am.Chem.Soc., 1981,103(13):3782-3792) successfully established a high-yield one-step synthesis of calix[n]arenes by strictly controlling the reaction conditions In this way, the rapid development of cali...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D313/00C07D405/14C07D498/08A61K31/444A61K31/335A61K31/395A61P35/00
CPCC07D313/00C07D405/14C07D498/08
Inventor 安琳韩莉莉郑友广彭献娜周珊珊刘毅
Owner XUZHOU MEDICAL COLLEGE
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