Furocoumarin compound and application thereof

A technology of furanocoumarins and compounds, applied in the field of pharmaceutical applications, can solve the problems of poor patient tolerance, large side effects, curative effect and application impact

Inactive Publication Date: 2013-04-10
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, anti-endocrine drugs and antibiotics combined therapy are used to treat Hp infection at home and abroad, but due to the large side effects, poor patient tolerance, and drug resistance, the curative effect and application have been affected

Method used

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  • Furocoumarin compound and application thereof
  • Furocoumarin compound and application thereof
  • Furocoumarin compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Embodiment 1: the synthesis of Zb-2a and Zb-2b

[0052]

[0053] Zb-2a R 1 =Br

[0054] Zb-2b R 1 = Cl

[0055] (i) NBS / NCS, CCl 4 , reflow, 9h

[0056] Into a 10 mL round bottom flask were added 21.6 mg of psoralen, 1.1 equivalent (eq.) of NBS, and 5 mL of carbon tetrachloride. The temperature was raised to reflux under stirring for 9h. After cooling, the solvent was evaporated under reduced pressure, and the crude product was subjected to flash silica gel column chromatography (petroleum ether: CH 2 Cl 2 =1:1) to obtain the target compound 2'-bromofuranocoumarin Zb-2a as a light yellow solid with a yield of 32%.

[0057] Except that NCS was used instead of NBS in the 2′-bromofuranocoumarin synthesis step, 2′-chlorofuranocoumarin Zb-2b was synthesized in the same procedure as an off-white solid with a yield of 25%.

Embodiment 2

[0058] Embodiment 2: the synthesis of compound Zb-4a~Zb-4c and Zb-4d

[0059]

[0060] Zb-4a: R=OMe,

[0061] Zb-4b: R=OEt,

[0062] Zb-4c: R=OBu-n,

[0063] Zb-4d: R=OAc,

[0064] (i) MOMCl, HOAc, room temperature, 36h; (ii) Zb-4a~Zb-4c: ROH (R=Me, Et, n-Bu), reflux, 3h;

[0065] Zb-4d: NaOAc, HOAc, (Ac) 2 O, 110°C, 3h;

[0066] Step 2.1: Add 300 mg psoralen and 10 mL glacial acetic acid to a 25 mL round bottom flask. After stirring evenly, 2 mL MOMCl was added to the above reaction system. Under stirring at room temperature, the reaction was sealed until the starting material disappeared (about 36h, detected by TLC). Add 20 mL of water, extract with EtOAc (30 mL×3), wash with saturated sodium bicarbonate, wash with water, and dry over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the crude product was eluted by flash silica gel column chromatography gradient (petroleum ether: EtOAc=4:1~2:1) to obtain 221 mg of c...

Embodiment 3

[0070] Embodiment 3: the synthesis of compound Zb-11c~Zb-11g

[0071]

[0072] R=OPr -n ,OBu -n , NEt 2 ,

[0073] NHPh-p-NO 2 , NHPh-p-OMe

[0074] (i) MOMCl, HOAc, room temperature, 14h; (ii) Zb-11c~Zb-11d: ROH (R=n-Pr, n-Bu), reflux;

[0075] Zb-11e~Zb-11g: Et 2 NH (or p-NO 2 PhNH 2 , or p-MeOPhNH 2 ), K 2 CO 3 , acetone, reflux, 3h;

[0076] Step 3.1: Add 500 mg of 8-methoxypsoralen and 3 mL of glacial acetic acid to a 25 mL round bottom flask. After stirring evenly, add 1 mL MOMCl to the above reaction system. Under stirring at room temperature, the reaction was sealed until the starting material disappeared (about 14 h, detected by TLC). Add water 20mL, CH 2 Cl 2 Extract (30mL×3), wash with water, and dry over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the crude product was eluted by flash silica gel column chromatography gradient (petroleum ether: acetone = 6:1 ~ 3:1) to obtain 480 mg of compoun...

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Abstract

The invention relates to a furocoumarin compound and application thereof, in particular to a novel furocoumarin compound shown as a general formula I and application thereof serving as an active ingredient to the preparation of a medicament for treating or preventing diseases relevant to bacterial infection, in particular to the application of the novel furocoumarin compound serving as the activeingredient to the preparation of a medicament for treating or preventing diseases caused by or mediated by helicobacter pylori.

Description

technical field [0001] The invention belongs to the technical field of medicine application. Specifically, the present invention relates to a class of novel furanocoumarin compounds and their use as active ingredients in the preparation of medicines for the treatment or prevention of diseases associated with bacterial infections, especially as active ingredients in the preparation of drugs for the treatment or prevention of diseases caused by pylori Use in medicine for diseases caused or mediated by Helicobacter. Background technique [0002] Helicobacter pylori (Hp) is a spiral microaerophilic Gram-negative bacillus that exists in human gastric mucosa. Modern research shows that the occurrence and treatment of diseases such as active gastritis, peptic ulcer and gastric cancer are closely related to Helicobacter pylori: the detection rate of Hp in patients with active gastritis and gastric erosion is as high as 95%, and the eradication of Hp can make the symptoms of gastrit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/04A61K31/37A61P31/04A61P1/04A61P35/00
Inventor 岳建民张邦乐杨升平樊成奇董蕾吴艳
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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