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Bis(aminodithioformic acid)-1,3-propylene diester compound and its synthesis method, pharmaceutical composition and application

A technology of dimethylaminodithioformic acid and compounds, which is applied in the field of preparation of drugs for treating or preventing cancer, and can solve problems such as failure to function, tumor cell death, etc.

Inactive Publication Date: 2016-01-27
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Antitumor drugs that act directly on DNA mainly affect or destroy the structure or function of DNA, making it unable to play a role in the process of cell proliferation, eventually leading to the death of tumor cells

Method used

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  • Bis(aminodithioformic acid)-1,3-propylene diester compound and its synthesis method, pharmaceutical composition and application
  • Bis(aminodithioformic acid)-1,3-propylene diester compound and its synthesis method, pharmaceutical composition and application
  • Bis(aminodithioformic acid)-1,3-propylene diester compound and its synthesis method, pharmaceutical composition and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0120] Example 1: Bis(dimethylaminodithioformic acid)-2-acetyl-1,3-propanediester

[0121]

[0122] Dissolve dimethylamine hydrochloride (16.31g, 200mmol) in acetone (23.24g, 400mmol), add paraformaldehyde (7.21g, 240mmol), 50mL water and 5mL isopropanol, and reflux for 16h. After cooling to room temperature, it was directly used in the next step without separation and purification. Dissolve dimethylamine hydrochloride (32.62g, 400mmol) in 100mL of acetone, add triethylamine (80.96g, 800mmol), stir for 15min, add carbon disulfide (38.07g, 500mmol), react at room temperature for 30min, add the previous step The reaction solution was reacted at room temperature for 17h. The acetone in the reaction solution was distilled off under reduced pressure, the residue was extracted with ethyl acetate (40mL×3), the organic phases were combined, washed with saturated brine (30mL×2), dried over anhydrous sodium sulfate, filtered, concentrated, and the remaining The compound was recryst...

Embodiment 2

[0126] Example 2: Bis(dimethylaminodithioformic acid)-2-benzoyl-1,3-propanediester

[0127]

[0128] Dissolve acetophenone (0.61g, 5mmol) in 10mL of acetic acid, add dimethylamine hydrochloride (0.82g, 10mmol) and paraformaldehyde (0.31g, 10mmol), reflux for 12h, and cool the reaction solution to room temperature , The solvent was distilled off under reduced pressure to obtain intermediate 2a. Dissolve dimethylamine hydrochloride (0.82g, 10mmol) in 25mL of water, add potassium carbonate (2.77g, 20mmol), stir for 15min, add carbon disulfide (0.92g, 12mmol), react at room temperature for 30min, add intermediate 2a, After reacting at room temperature for 12 hours, a yellow solid precipitated out, was filtered with suction, washed with water, and dried. The solid was recrystallized from ethyl acetate to obtain 0.83 g of a light yellow solid, and the total yield of the two-step reaction was 43%.

[0129] 1 HNMR (400MHz, CDCl 3 ):δ=3.23(s,6H),3.45(s,6H),3.57-3.62(m,2H),3.67-3...

Embodiment 3

[0132] Example 3: Bis(dimethylaminodithioformic acid)-2-(4-fluorobenzoyl)-1,3-propanediester

[0133]

[0134] Using 4-fluoroacetophenone as a raw material, the synthesis method is the same as in Example 2, and the total yield of the two-step reaction is 27%.

[0135] 1 HNMR (400MHz, CDCl 3):δ=3.31(s,6H),3.52(s,6H),3.62-3.67(m,2H),3.72-3.77(m,2H),4.50(s,1H),7.11-7.15(m,2H ),8.12-8.16(m,2H).

[0136] 13 CNMR (100MHz, CDCl 3 ): δ=38.52, 41.60, 44.47, 45.39, 115.72(d, J=22Hz), 131.77(d, J=10Hz), 132.94, 166.08(d, J=254Hz), 196.21, 199.55.

[0137] Anal. CaldforC 16 h 21 FN 2 OS 4 : C, 47.50; H, 5.23; N, 6.92; Found: C, 47.75; H, 5.36; N, 7.03.

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PUM

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Abstract

The invention relates to a bis(aminodithioformate)-1,3-propane diester compound, and synthesis method thereof, a pharmaceutical composition containing the compound and a use, and especially relates to the use in preparing drugs for treating or preventing cancers. The compound is represented as the formula (I), wherein A is selected from substituted or unsubstituted alkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclic group, R1 and R2 are the same or different and are independently selected from hydrogen, alkyl, aryl alkyl or heteroaryl alkyl, or a substituted or unsubstituted heterocyclic ring formed together by the R1, the R2 and an N atom connected with the R1 and the R2.

Description

technical field [0001] The present invention relates to bis(aminodithioformic acid)-1,3-propylene diester compound, its synthesis method, pharmaceutical composition containing the compound and its use, especially in the preparation of medicines for treating or preventing cancer use. Background technique [0002] Malignant tumors are a large class of diseases caused by normal cells in the body due to multiple reasons, multiple stages and multiple mutations. At present, cancer has become a disease that seriously threatens human health. The mortality rate of human beings caused by malignant tumors accounts for the second highest among all diseases, second only to cardiovascular and cerebrovascular diseases. Tumor treatment methods mainly include surgery, radiation therapy, drug therapy (chemotherapy), and biological therapy, but chemotherapy is still the main method to a large extent. [0003] According to the principle of action of anti-tumor drugs currently used clinically,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C333/20C07C333/24C07D207/333C07D209/12C07D213/50C07D215/14C07D215/18C07D215/38C07D235/04C07D277/26C07D277/68C07D311/12C07D333/56C07D401/04C07D401/12C07D471/04C07D487/04A61K31/27A61K31/37A61K31/381A61K31/40A61K31/4045A61K31/4184A61K31/426A61K31/428A61K31/437A61K31/4406A61K31/47A61K31/4709A61K31/496A61K31/5025A61K31/5377A61K31/541A61P35/00
Inventor 李润涛葛泽梅李日东周柔丽李莉程铁明
Owner PEKING UNIV