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Preparation method and application of aromatic carboxylate compound

A technology of aromatic carboxylic acid esters and compounds, which is applied in the application field of anti-prostate cancer, can solve the problems of few effective inhibition of prostate cancer, achieve the effect of inhibiting cell activity, simple preparation method, and high anti-cancer activity

Inactive Publication Date: 2020-04-07
WEIFANG MEDICAL UNIV +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In the current research, it has been reported that organotin carboxylates have inhibitory effects on a variety of tumors, but there are few reports on the effective inhibition of prostate cancer

Method used

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  • Preparation method and application of aromatic carboxylate compound
  • Preparation method and application of aromatic carboxylate compound
  • Preparation method and application of aromatic carboxylate compound

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Experimental program
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Effect test

Embodiment 1

[0021] Preparation of novel aromatic carboxylate compounds: add 1.0 mmol of H to a standard Schlenk tube 3 tmapob, 1.0 mmol of sodium ethoxide, 1.0 mmol of dibutyltin dichloride, 30 mL of dichloromethane, stirred at 30°C for 5 hours, and rotary evaporated to obtain a light yellow powdery solid; recrystallized with dichloromethane-ether , to obtain a light yellow transparent crystal, which is a novel aromatic carboxylate compound; wherein, the volume ratio of dichloromethane to ether is 8:1. Yield 62%, melting point 124-126°C.

[0022] Through infrared spectrum analysis and elemental analysis and X-ray single crystal diffraction, the results are as follows:

[0023] Infrared spectrum (KBr, cm -1 ): v as (C=O) 1672, 1645, 1578, v s (C-O) 1366, 1273; v(Sn-O-Sn) 708, v(Sn-O) 473.

[0024] Elemental Analysis: Calculated Value C 48 h 80 Br 2 N 6 o 10 sn 2 : C, 44.40; H, 6.21; N, 6.47%; Found C, 44.42; H, 6.23; N, 6.45%.

[0025] Crystallographic data and structural analy...

Embodiment 2

[0028] Preparation of novel aromatic carboxylate compounds: add 1.0 mmol of H to the flask 3 tmapob, 1.0 mmol of sodium ethoxide, 1.0 mmol of dibutyltin dichloride, 40 mL of dichloromethane, stirred at 30°C for 6 hours, and rotary evaporated to obtain a pale yellow solid; recrystallized with dichloromethane-ether, A light yellow transparent crystal is obtained, which is a novel aromatic carboxylic acid ester compound; wherein, the volume ratio of dichloromethane to diethyl ether is 7:1. Yield 65%, melting point 124-126°C.

Embodiment 3

[0030] Preparation of novel aromatic carboxylate compounds: Add 2.0 mmol of H3tmapob, 2.0 mmol of sodium ethoxide, 1.0 mmol of dibutyltin dichloride, 60 mL of dichloromethane into the flask, stir at 30 °C for 7 hours, and then rotovap , to obtain a light yellow solid; recrystallization with dichloromethane-ether, to obtain a light yellow transparent crystal, which is a new aromatic carboxylate compound; wherein, the volume ratio of dichloromethane to ether is 6:1. Yield 63%, melting point 124-126°C.

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Abstract

The invention discloses a novel aromatic carboxylate compound, and a preparation method and an application thereof. The structural formula of the compound is shown in the description. The preparationmethod comprises the following steps: adding 1.0 mmol of H3tmapob, 1.0 mmol of sodium ethoxide, 1.0 mmol of dibutyltin dichloride and 20-50 mL of dichloromethane into a reaction container, performingstirring at 30 DEG C for 5-7 h, and carrying out rotary evaporation to obtain a faint yellow powdery solid; and recrystallizing the faint yellow powdery solid with dichloromethane-diethyl ether to obtain a faint yellow transparent crystal that is the carboxylate compound, wherein a volume ratio of the dichloromethane to diethyl ether is 8:1 to 6: 1. Compared with platinum anticancer drugs commonlyused at present, the novel aromatic carboxylate compound has the characteristics of high anti-human prostate cancer cell activity, good lipid solubility, low cost, simple preparation method and the like, and provides a new way for developing anticancer drugs. In the formula, n-Bu represents an n-butyl group.

Description

technical field [0001] The invention relates to a novel aromatic carboxylic acid ester compound, a preparation method thereof, and the application of the compound in the preparation of anticancer drugs, especially for anti-prostate cancer. Background technique [0002] Prostate cancer refers to epithelial malignant tumors that occur in the prostate. According to the latest statistics from the International Agency for Research on Cancer of the World Health Organization, there were 1.3 million newly diagnosed prostate cancer patients in 2018, accounting for about 15% of the total number of new cancer cases, and it is the second most common cancer in men worldwide. The pathological types of prostate cancer include adenocarcinoma (acinar adenocarcinoma), ductal adenocarcinoma, urothelial carcinoma, squamous cell carcinoma, and adenosquamous carcinoma, most of which originate in the peripheral zone of the prostate, with relatively insidious onset and slow growth. Therefore, earl...

Claims

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Application Information

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IPC IPC(8): C07F7/22A61P35/00A61P13/08
CPCA61P13/08A61P35/00C07F7/2224
Inventor 李法辉王颖宋伟国
Owner WEIFANG MEDICAL UNIV
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