Fluoro-acrylamide derivative

A technology of drugs and compounds, applied in the direction of drug combinations, medical preparations containing active ingredients, organic active ingredients, etc.

Inactive Publication Date: 2012-09-19
苏春华 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these drugs have produced different degrees of drug resistance after a period of clinical use, so it is necessary to explore new antibiotics for drug-resistant bacteria

Method used

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  • Fluoro-acrylamide derivative
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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0006] Embodiment 1: the synthesis of compound 1a

[0007]

[0008] 1) Synthesis of compound 3:

[0009] Dissolve 45.4 grams of raw material 2, 20.6 grams of methyl acrylate and 1.26 grams of triphenylphosphine in 100.0 mL of DMF and 200.0 mL of acetonitrile, add 0.66 grams of palladium acetate, and replace the reaction system with nitrogen three times. Under nitrogen atmosphere, 100 °C overnight. Stop the reaction, cool to room temperature, and filter with suction. Add 400.0 mL of 10.0% sodium hydroxide solution to the filtrate to remove the solvent under reduced pressure. After stirring for 3 hours, adjust the pH to about 3.0 with concentrated hydrochloric acid. A large amount of solids are precipitated. Filter with suction. The filter cake was recrystallized with ethanol, and dried under vacuum at 50° C. for 5 hours to obtain 26.5 g of compound 3 with a yield of 61%. HNMR (400Hz, CDCl 3 ): 11.01(s, 1H), 8.91(s, 1H), 8.37(s, 1H), 8.02(s, 1H), 7.61(d, J=13.6Hz, 1H), 6.4...

Embodiment 2

[0020] Embodiment 2: the synthesis of compound 1b

[0021]

[0022] 1) Synthesis of compound 6b:

[0023] 0.2 mol of raw material 5b, 0.24 mol of methyl bromoacetate and 0.6 mol of anhydrous potassium carbonate were refluxed overnight in 200 mL of acetonitrile. Heating was stopped, cooled to room temperature, suction filtered, and the filtrate was distilled under reduced pressure and then recrystallized with ethanol to obtain compound 6b. C 11 h 7 f 3 o 2 S, 37.4 g, 72% yield. MS (m / z): 261.2.

[0024] 2) Synthesis of compound 7b:

[0025] 0.05 mol of compound 6b, 0.1 mol of methylamine hydrochloride and 0.1 mol of triethylamine were added to 100.0 mLd of methanol, and stirred at 60° C. for 5 hours. The reaction was stopped, the reaction liquid was cooled to room temperature, methanol was distilled off under reduced pressure, and 100.0 mL of ice water was added, a large amount of solids were precipitated, filtered with suction to obtain a solid, which was washed wit...

Embodiment 3

[0030] Embodiment 3: the synthesis of compound 1c:

[0031]

[0032] 1) Synthesis of compound 6c:

[0033] 0.2 mol of starting material 5c, 0.24 mol of methyl bromoacetate and 0.6 mol of anhydrous potassium carbonate were refluxed overnight in 200 mL of acetonitrile. Heating was stopped, cooled to room temperature, suction filtered, and the filtrate was distilled under reduced pressure and then recrystallized with ethanol to obtain compound 6c. C 11 h 8 f 3 o 2 N, 27.2 g, 56% yield. MS (m / z): 244.2.

[0034] 2) Synthesis of compound 7c:

[0035] 0.05 mol of compound 6c, 0.1 mol of methylamine hydrochloride and 0.1 mol of triethylamine were added to 100.0 mLd of methanol, and stirred at 60° C. for 5 hours. The reaction was stopped, the reaction liquid was cooled to room temperature, methanol was distilled off under reduced pressure, and 100.0 mL of ice water was added, a large amount of solids precipitated, filtered by suction to obtain a solid, which was washed with...

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Abstract

The invention relates to a new compound with remarkable antibacterial and antineoplastic activity, which has the following structure (shown in formula I), and has good antibacterial function for methicillin-resistant staphylococcus aureus (MRSA) and methicillin sensitive staphylococcus aureus (MSSA) as well as good antineoplastic function for human cervical cancer Hela cells, human liver cancer BEL-7402 cells, human mucinous epidermoid lung cancer A549 cells, human breast cancer MCF-7/ s cells and human glioma U251 cells. (In the formula I,) R=-CH3 or CF3, X=O, S or N, and R1=-Cl, -F, -CH3, -CF3, -OCH3 and -OCF3.

Description

Technical field: [0001] The present invention relates to a new compound for antibacterial effect, which has good antibacterial activity against MRSA and MSSA. Background technique: [0002] In recent years, with the widespread use of antibiotics (including humans and animals), the increase in the use of glucocorticoids and immunosuppressants, and the increase in elderly patients, the problem of pulmonary drug-resistant bacterial infections has become increasingly prominent. Penicillin-resistant Streptococcus pneumoniae, methicillin-resistant Staphylococcus aureus (MRSA), vancomycin-resistant Enterococcus (VRE), extended-spectrum beta-lactamase (ESBL)-producing Gram-negative bacteria Wait. Methicillin-resistant Staphylococcus aureus is also a difficult issue. Since the first strain of MRSA was detected for more than 40 years, MRSA infection has been on the rise all over the world. According to the National Nosocomial Infection Surveillance (NNIS) report, 182 hospitals in 197...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04A61K31/4375A61P31/04A61P35/00
Inventor 苏春华张哲峰
Owner 苏春华
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