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Preparation method and application of 3H-1,2-dithiole-3-thioketone compound

A technology of compounds and vulcanizing agents, applied in the fields of medical preparations containing active ingredients, organic chemistry, pharmaceutical combinations, etc., can solve the problems of environmental pollution, difficult post-processing, unsafe production operations, etc., to reduce production costs and vulcanization speed. Fast, productivity-enhancing effects

Inactive Publication Date: 2013-03-27
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this preparation method needs to go through the process of several intermediates when generating 3H-1,2-dithiocyclopentene-3-thiones, and when the vulcanization reaction does not completely stay in the intermediates, it will cause more by-products and The polarity is similar, and it is difficult to reprocess; phosphorus pentasulfide is highly toxic, and it is hydrolyzed into phosphoric acid and hydrogen sulfide when it meets water, so it smells like rotten eggs in the air and pollutes the environment; and because hexamethyldisiloxane encounters high temperature, open flame and Strong oxidants are easy to cause combustion, so a large amount of hexamethyldisiloxane is used as raw material, which makes the production operation extremely unsafe

Method used

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  • Preparation method and application of 3H-1,2-dithiole-3-thioketone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1: Preparation of 5-(4-fluorophenyl)-3H-1,2-dithiol-3-thione (YC1-2)

[0029] Methyl p-fluorobenzoylacetate (3.71 g, 18.9 mmol), Lawson's reagent (13.76 g, 34.0 mmol), sulfur (0.72 g, 22.34 mmol) and MBT (3.2 mg, 0.019 mmol) and MgO (8 mg, 0.2 mmol) was added to 20 mL of toluene, heated to reflux for 5 h, the reaction was completed, filtered, evaporated to dryness under reduced pressure, and recrystallized from acetone to obtain a red solid with a yield of 76.6%. m.p.108.3~110.0℃. 1 HNMR (400Hz, CDCl 3 ), δ(ppm): 7.66(s, 2H, ArH), 7.37(s, 1H, =CH), 7.18(s, 2H, ArH). 13 C-NMR (400MHz, CDCl 3 ), δ(ppm): 215.398, 171.482, 166.623, 163.247, 135.893, 129.124, 129.007, 117.060, 116.765.HR-MS:Calcd.For C 9 H 5 FS 3 [M+H] + :228.9610,Found:228.9610.

Embodiment 2

[0030] Example 2: Preparation of 5-(2-thienyl)-3H-1,2-dithiol-3-thione (YC1-3)

[0031] Using methyl 2-thiopheneformyl acetate, Lawson's reagent, sulfur, MBT and MgO as raw materials, see the synthesis method of YC1-2, red crystal, yield 68.6%. m.p.119.2~120.9℃. 1 HNMR (400Hz, CDCl 3 ),δ(ppm): 7.59(s,1H,=CH),7.54(s,1H,ArH),7.32(s,1H,ArH),7.15(s,1H,ArH). 13 C-NMR (400MHz, CDCl 3 ), δ(ppm): 214.456, 165.134, 134.629, 133.866, 131.083, 129.247, 129.065.HR-MS:Calcd.For C 7 H 7 S 4 [M+H] + :216.9269,Found:216.9268.

Embodiment 3

[0032] Example 3: Preparation of 5-(4-Tolyl)-3H-1,2-dithiol-3-thione (YC1-4)

[0033] Using methyl p-toluoyl acetate, Lawson's reagent, sulfur, MBT and MgO as raw materials, the synthesis method is shown in the synthesis of YC1-2, red crystal, and the yield is 70.9%. m.p.114.3~115.6℃. 1 HNMR (400Hz, CDCl 3 ),δ(ppm):7.52(d,2H,J=8.1Hz,ArH),7.39(s,1H,=CH),7.26(d,2H,J=7.9Hz,ArH),2.46(s,3H ,CH 3 ). 13 C-NMR (400MHz, CDCl 3 ), δ(ppm): 215.481, 173.456, 143.354, 135.480, 130.498, 129.024, 126.984, 21.842.HR-MS:Calcd.For C 10 H 8 S 3 [M+H] + :224.9861,Found:224.9860.

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PUM

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Abstract

The invention relates to the field of medicine synthesis and discloses a preparation method and application of a 3H-1,2-dithiole-3-thioketone compound. According to the preparation method of the 3H-1,2-dithiole-3-thioketone compound shown in a formula I described in the specification, the yield of the 3H-1,2-dithiole-3-thioketone compound is improved, the problem of unsafe operation in the production of hexamethyl disiloxane is solved, the environmental pollution is reduced, the preparation method is simple to operate, a vulcanization accelerator is low in price and easy to obtain, the production cost is reduced, and the preparation method is suitable for batch preparation of the 3H-1,2-dithiole-3-thioketone compound shown in the formula I. Furthermore, the 3H-1,2-dithiole-3-thioketone compound shown in the formula I plays a suppression role in multiplication of a human liver cancer HePg2 cell strain, a human lung cancer A549 tumor cell strain, a mouse melanoma B16 tumor cell strain and a human liver cancer SMMC-7721 tumor cell strain, and can be used for preparing antitumor medicines.

Description

technical field [0001] The invention relates to the field of pharmaceutical synthesis, in particular to a preparation method and application of a 3H-1,2-dithiocyclopentene-3-thione compound. Background technique [0002] Tumor is an abnormal lesion formed by abnormal clonal proliferation of a certain cell in the local tissue under the action of various carcinogenic factors. Tumors are generally divided into two categories: benign and malignant. Among them, malignant tumor, also known as cancer, is an important disease that seriously threatens human health. According to the report of the World Health Organization WHO, there are 10 million new cases of cancer every year in the world, and the number of people who die from cancer ranks second, after the number of deaths from cardiovascular diseases. According to statistics from the Ministry of Health of my country, in recent years, there are 2 million new malignant tumor patients and 1.3 million deaths in China each year, and ...

Claims

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Application Information

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IPC IPC(8): C07D339/04C07D409/04A61K31/385A61P35/00
Inventor 敖桂珍曹毅宋恒张英王盼盼
Owner SUZHOU UNIV
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