CN102816121B - 1-acyl group-3-pseudoallyl benzo imidazolone derivatives is as the purposes of anti-bacterial drug - Google Patents
1-acyl group-3-pseudoallyl benzo imidazolone derivatives is as the purposes of anti-bacterial drug Download PDFInfo
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Abstract
The invention discloses the purposes of 1-acyl group-3-pseudoallyl benzo imidazolone derivatives as anti-bacterial drug.This compound has structure shown in formula (I), and in formula, R is main carbon chain lengths is C
3~ C
6α, beta-unsaturated acyl base or halogenacyl.Compound provided by the invention can be processed into tablet, capsule or other formulation for clinical treatment and/or prevention bacteriological infection.
Description
Technical field
The present invention relates to the purposes of 1-acyl group-3-pseudoallyl benzo imidazolone derivatives as anti-bacterial drug, belong to medical art.
Background technology
Benzimidazolone is the oxidized derivatives of 2 carbon atoms on imidazole ring, in dyestuffs industries, have purposes (JolantaS.etal.Dyesandpigments.2001,15-27) widely as intermediate.In addition, benzimidazolone derivatives also has obvious pharmacologically active, generally apply as clinical application, as s-generation antihistamine drug oxatomide just belongs to benzimidazolone derivatives (IwamotoK., etal.Arzneimittel-forschung-drugResearch.2001,51:971-976.).The phosphodiesterase inhibitor that nearest European patent publication one is novel, have good curative effect to multiple cardiovascular disorder clinically, its effective constituent is exactly benzimidazolone derivatives, wherein N
1substituted pyridine derivative is introduced in position, N
3the multiple substituting groups (Europeanpatent.EP1958947A1) such as alkyl, aryl, heterocycle and fragrant heterocycle are then introduced in position.British scientist finds that benzimidazolone is at N
3the a series of derivatives obtained after introducing benzene oxygen propylpiperdine are novel opiate receptor (NOP) agonists, because medicine such as the morphine etc. based on classical opioid receptors has larger side effect, therefore namely this receptor causes the great interest of medicine scholar after being found from 1994, this kind of benzimidazolone derivatives then shows the very high potential (RonaldPalinetal..Bioorganic & MedicinalChemistry.2007,15:1828-1847.) being developed to novel analgesic drug product.Italy medicine scholar is at the N of benzimidazolone
1introduce substituted aryl and find that it shows good anti-AIDS activity later, its Main Function mechanism suppresses the activity (Anna-MariaMonforteetal.Bioorganic & MedicinalChemistry.2008,16:7429-7435.) of non-nucleoside reverse transcriptase.
Although benzimidazolone skeleton can be modified, position is many, structure of modification leeway is large, have been found that multiple pharmacologically active at present, but with regard to the compound with 1-acyl group-3-pseudoallyl benzo imidazolone skeleton, (ShengkunLi except plant epiphyte resisting activity disclosed in contriver, etal.J.Agric.FoodChem.2010,2668-2672; Ji Zhiqin etc., benzimidazole amide bactericide, Chinese invention patent, application number 200810184460.9), do not have the report of such antifungal activity at present again.Contriver finds in follow-up result of study, the antibacterial activity of this compounds is excellent more than its anti-mycotic activity, wherein the specific activity penbritin of part preferred compound to various bacteria exceeds more than 10 times, especially to pathogenic very strong endurance strain clinically, gold goal bacterium (MRSA) as methicillin-resistant also shows very strong bacteriostatic activity, and this compounds also has the antimicrobial spectrum wider than penbritin simultaneously.
The invention discloses the preparation method of 1-acyl group-3-pseudoallyl benzo imidazolone derivatives and the purposes as anti-bacterial drug thereof.
Summary of the invention
The object of this invention is to provide the purposes of 1-acyl group-3-pseudoallyl benzo imidazolone derivatives as anti-bacterial drug.This compounds is to streptococcus aureus (Staphyloccocusaureus), streptococcus agalactiae (Streptococcusagalactiae), Bacillus subtilus (Bacillussubtilis), multiple gram positive bacterium and the intestinal bacteria (Escherichiacoli) such as bacillus cereus (Bacilluscereus), Pseudomonas aeruginosa (Pseudomonasaeruginosa), the multiple gram negative bacteriums such as salmonella arizonae (Salmonellaarizonae) have very high bacteriostatic activity.
1-acyl group-3-pseudoallyl benzo imidazolone derivatives provided by the invention has structure shown in following general formula (I),
In formula, R is selected from following substituting group:
1) main carbon chain lengths is C
3~ C
6α, beta-unsaturated acyl base, 3 and 4 carbon atoms can be one or two hydrogen atom, also can be replaced by methyl or ethyl independently of one another by wherein in carbochain 2;
2) main carbon chain lengths is C
3~ C
6halogenacyl, wherein in carbochain 2,3 and 4 carbon atoms can be two hydrogen atoms, also can be replaced by the halogen atom of different quantities independently of one another.
The preparation method of the compound of general formula of the present invention (I) comprises the steps: first to prepare pseudoallyl benzo imidazolone with O-Phenylene Diamine and methyl aceto acetate condensation; then with α; beta-unsaturated carboxylic acid or halogenated acid and triphosgene carry out acylation reaction under triethylamine catalysis in dichloromethane solvent; i.e. obtained corresponding 1-acyl group-3-pseudoallyl benzo imidazolone derivatives, its structure is confirmed through mass spectrum and NMR (Nuclear Magnetic Resonance) spectrum technology.
Also the following step that can adopt of the compound of general formula of the present invention (I) is prepared: first prepare pseudoallyl benzo imidazolone with O-Phenylene Diamine and methyl aceto acetate condensation, then with α, beta-unsaturated carboxylic acid or halogenated acid are at condensing agent 1,3-dicyclohexylcarbodiimide (DCC)/to reacting obtained under Dimethylamino pyridine (DMAP) effect in dichloromethane solvent, its structure is confirmed through mass spectrum and NMR (Nuclear Magnetic Resonance) spectrum technology.
When R is respectively acryl, Alpha-Methyl acryl, trans-Beta-methyl acryl; cis-Beta-methyl acryl, 2E, 4E-hexadiene acyl group; 2E, 4Z-hexadiene acyl group, 2Z; 4E-hexadiene acyl group, 2Z, 4Z-hexadiene acyl group; chloracetyl, acetyl bromide, 3-chlorine propionyl; during 3-bromine propionyl, its anti-microbial activity is very excellent.
More preferably R is respectively acryl, Alpha-Methyl acryl, trans-Beta-methyl acryl, 2E, 4E-hexadiene acyl group, 3-chlorine propionyl and 3-bromine propionyl.
1-acyl group-3-pseudoallyl benzo imidazolone derivatives provided by the invention has that raw material is simple and easy to get, synthesis step is few, reaction yield and the high feature of product purity.
1-acyl group-3-pseudoallyl benzo imidazolone derivatives provided by the invention has very high bacteriostatic activity to multiple gram negative bacteriums such as the multiple gram positive bacterium such as streptococcus aureus, streptococcus agalactiae, Bacillus subtilus, bacillus cereus and intestinal bacteria, Pseudomonas aeruginosa, salmonella arizonaes.
In preferred compound provided by the invention, when R is Alpha-Methyl acryl, it tries the minimum inhibition concentration (MIC value) of bacterium all at 1.56 μ gmL to each confession
-1below, all lower than contrast medicament penbritin sodium salt.Other preferred compounds try the minimum inhibition concentration (MIC value) of bacterium also all at 0.78 ~ 12.5 μ gmL to each confession
-1between.
1-acyl group-3-pseudoallyl benzo imidazolone derivatives provided by the invention and β-lactam antibitics have diverse molecular skeleton; than a large amount of Penicillin antibiotics activity used is higher clinically; antimicrobial spectrum is wider; simultaneously more responsive to the resistant strain of resistance to β-lactam antibitics, and there is not cross resistance between existing microbiotic.
1-acyl group-3-pseudoallyl benzo imidazolone derivatives provided by the invention can be processed into tablet, capsule or other suitable dosage forms and is used for the treatment of and/or prevents bacteriological infection.
Embodiment
Contribute to understanding the present invention by following embodiment, but do not limit content of the present invention.
Embodiment 1
The synthesis of 1-pseudoallyl benzo imidazolone
In three mouthfuls of reaction flasks that water trap is housed, add O-Phenylene Diamine and the 220mL dimethylbenzene of 54.0g (0.5mol), 5mL potassium hydroxide-ethanol solution (wherein potassium hydroxide weight is 1.0g), after heated and stirred backflow, slow dropping methyl aceto acetate 71.5g (0.55mol) and 20mL dimethylbenzene mixed solution, after dripping off, stirring and refluxing azeotropic dehydration only appears as to without the globule, then continues stirring and refluxing 2h.Reaction is finished, cooling, crystallization, and filtration, drying, obtain white particulate crystallization 76.5g (productive rate 87.9%), be 1-pseudoallyl benzo imidazolone, fusing point 120 ~ 122 DEG C, mass spectrum (ESI, positive ion mode) [M+H]
+m/z175.
Embodiment 2
Synthesis (the numbering: I-01) of 1-acryl-3-(the third-1-alkene-2-base)-1H-2-ketone benzimidaozole
Get 1-pseudoallyl benzo imidazolone 1.74g (0.01mol) and vinylformic acid 0.72g (0.01moL) is placed in 100mL reaction flask, add the methylene dichloride of 30mL drying process, be stirred to and dissolve completely, add triethylamine 0.2mL.Take triphosgene 1.19g (0.004moL) to be again dissolved in dried 10mL methylene dichloride, slowly drip in reaction flask under ice bath.After dripping, reaction system returns to room temperature, continue stirring 5 ~ 8h, after reaction terminates, in reaction system, add 20mL saturated sodium bicarbonate aqueous solution, fully leave standstill phase-splitting after concussion, organic phase is through washing, magnesium chloride drying, decompression precipitation, again through purification by silica gel column chromatography (eluent is petrol ether/ethyl acetate=4/1), obtain target compound 2.11g (productive rate 92.5%), fusing point 108 ~ 110 DEG C.Mass spectrum (ESI, positive ion mode) [M+H]
+m/z229.
1HNMR(CDCl
3)，δ2.20(s，3H，CH
3ofisopropenyl)，5.27(s，1H，C＝CH
2)，5.48(s，1H，C＝CH2)，5.99(d，J＝16.2Hz，1H，CH
2ofacryloyl)，6.68(d，J＝12.8Hz，1H，CH
2ofacryloyl)，7.06(d，J＝8.0Hz，1H，Ph)，7.15-7.27(m，2H，Ph)，7.74(dd，J＝16.2，12.8Hz，1H，CHofacryloyl)，8.23(d，J＝8.0Hz，1H，Ph)。
Embodiment 3
1-(synthesis (the numbering: I-10) of 3-chlorine propionyl-3-(the third-1-alkene-2-base)-1H-2-ketone benzimidaozole
Get 1-pseudoallyl benzo imidazolone 1.74g (0.01mol) and 3-chloropropionic acid 1.08g (0.01moL) is placed in 100mL reaction flask, add the methylene dichloride of 30mL drying process, be stirred to and dissolve completely.Add 1,3-dicyclohexylcarbodiimide (DCC) 2.48g (0.012moL) and to Dimethylamino pyridine (DMAP) 100mg, stirred at ambient temperature 5 ~ 8h.After reaction terminates, reaction solution proceeds in sand core funnel, suction filtration, the a small amount of eluent ethyl acetate of filter residue, elutriant and filtrate merge, decompression precipitation, then through purification by silica gel column chromatography (eluent is petrol ether/ethyl acetate=4/1), obtain target compound 2.27g (productive rate 86.0%), fusing point 110 ~ 112 DEG C.Mass spectrum (ESI, positive ion mode) [M+H]
+m/z265.
1HNMR(CDCl
3)，δ2.20(s，3H，CH
3ofisopropenyl)，2.75(t，J＝7.0Hz，2H，CH
2of3-chloropropanoyl)，3.82(t，J＝7.0Hz，2H，CH
2of3-chloropropanoyl)，5.27(s，1H，C＝CH
2)，5.48(s，1H，C＝CH2)，7.06(d，J＝8.0Hz，1H，Ph)，7.15-7.27(m，2H，Ph)，8.23(d，J＝8.0Hz，1H，Ph)。
According to same method, other compound of the present invention can be synthesized, in table 1.
Table 11-acyl group-3-pseudoallyl benzo imidazolone derivatives
Embodiment 4
Drug susceptibility test
The disk diffusion method worked out with reference to NCLLS carries out drug susceptibility test to part representative compound disclosed in this patent, concrete operation step is as follows: accurately take reagent agent, 10mg/mL is settled to acetone solution, quantitatively load on aseptic filter paper sheet that diameter is 6mm, every sheet drug loading is 20 μ g, dries for subsequent use again, take positive control medicament sodium ampicillin salt simultaneously, dissolve constant volume with sterilized water, make the aseptic filter paper sheet that drug loading is 20 μ g equally, dry for subsequent use.Adopt Double-Medium, wherein bottom is the nutrient agar of 2%, and upper strata is beef-protein medium.In each culture dish, adding 10ml bottom substratum with aseptic straw, after to be condensed, then (having inoculated for examination bacterium, inoculum size 7.5 × 10 by melting the upper strata substratum being cooled to 45 ~ 50 DEG C
5cFU/mL) the bottom media surface of having solidified is poured into, the aseptic filter paper sheet being loaded with different agents can be placed gently on each culture dish after to be solidified, every ware places 4, distance between filter paper is equal, refrigerator and cooled Tibetan 2h is placed in the thermostat container of 30 DEG C and cultivates, measure inhibition zone size after 24h and record its transparency, it the results are shown in Table 2.
Table 21-acyl group-3-pseudoallyl benzo imidazolone derivatives is to the drug susceptibility test result of 6 kinds of bacteriums
Note: B.C in table: bacillus cereus Bacilluscereus; B.S: Bacillus subtilis; S.A: streptococcus aureus Staphyloccocusaureus; MRSA: methicillin-resistant staphylococcus aureus Methicillin-resistantStaphylococcusaureus; E.C: intestinal bacteria Escherichiacoli; P.A: Pseudomonas aeruginosa Pseudomonasaeruginosa; "-" indicates without inhibition zone, and "+" represents that inhibition zone is visible, and " ++ " represents that inhibition zone is clear, and " +++ " represents that inhibition zone is transparent.
Embodiment 5
Minimum inhibition concentration measures (MIC value)
The micro-dilution method worked out with reference to NCCLS carries out minimum inhibition concentration mensuration to the part representative compound that this patent relates to, concrete operation step is as follows: with the confession examination bacterium bacterium colony of transfering loop picking 4 ~ 5 same modality on culture dish, in access Mueller-Hinton meat soup, 35 DEG C are cultured to slight muddy rear (about 3 ~ 5h) and proceed in 0.9% physiological saline, adjusting to Maxwell turbidity is 0.5 (make its absorbancy under 650nm wavelength be 0.020, be now equivalent to 1.5 × 10
8cFU/mL), then use Mueller-Hinton broth dilution 200 times, its inoculum size is then equivalent to 7.5 × 10
5cFU/mL.The inoculation liquid of having diluted is proceeded in 96 orifice plates, every hole liquid volume added 190 μ L.Taking reagent agent 2mg is dissolved in 1mL methyl-sulphoxide (DMSO), series concentration gradient is become again by methyl-sulphoxide proportional diluted, getting 10 μ L respectively to add on 96 orifice plates in inoculation liquid, makes final liquor strength gradient be respectively 100,50,25,12.50,6.25,3.13,1.56,0.78 μ gmL
-1, every plate is separately established the blank of not adding medicine and is added the positive control of penbritin sodium salt, and in experiment, three repetitions are established in each process.Put in incubator by 96 orifice plates handled well, cultivate 24h, 650nm for 35 DEG C and measure transmittance, record different agents is to the MIC value for examination bacterium.Be greater than 85% standard that is Developing restraint with transmittance, MIC is the minimum concentration of Developing restraint.It the results are shown in Table 3.
Table 31-acyl group-3-pseudoallyl benzo imidazolone derivatives is to the minimum inhibition concentration of 6 kinds of bacteriums
Note: B.C in table: bacillus cereus Bacilluscereus; B.S: Bacillus subtilis; S.A: streptococcus aureus Staphyloccocusaureus; MRSA: methicillin-resistant staphylococcus aureus Methicillin-resistantStaphylococcusaureus; E.C: intestinal bacteria Escherichiacoli; P.A: Pseudomonas aeruginosa Pseudomonasaeruginosa
Embodiment 6
Prepared by the tablet being effective constituent with Compound I-01
Take 50g Compound I-01 and 100g sucrose, mixing evenly, then add vehicle (as Xylo-Mucine, Microcrystalline Cellulose, polyvinylpolypyrrolidone etc.), namely film-making agent method for making can be made into 1000, the I-01 tablet that specification is 50mg/ sheet routinely.
Claims (3)
1. there is the purposes of the 1-acyl group-3-pseudoallyl benzo imidazolone derivatives shown in following general formula (I) for the preparation of anti-bacterial drug,
In formula (I), R is selected from following substituting group: main carbon chain lengths is C
3~ C
6α, beta-unsaturated acyl base, 3 and 4 carbon atoms is one or two hydrogen atom, or is replaced by methyl or ethyl independently of one another by wherein in carbochain 2; Carbon chain lengths is C
3~ C
6halogenacyl, wherein in carbochain 2,3 and 4 carbon atoms are two hydrogen atoms, or are replaced by the halogen atom of different quantities independently of one another.
2. purposes as claimed in claim 1, wherein bacterium is streptococcus aureus (Staphyloccocusaureus), streptococcus agalactiae (Streptococcusagalactiae), Bacillus subtilus (Bacillussubtilis), bacillus cereus (Bacilluscereus) and intestinal bacteria (Escherichiacoli), Pseudomonas aeruginosa (Pseudomonasaeruginosa), salmonella arizonae (Salmonellaarizonae).
3. purposes as claimed in claim 1, its Chinese style (I) compound can be processed into tablet, capsule.
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Citations (4)
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|---|---|---|---|---|
| US3499085A (en) * | 1966-10-04 | 1970-03-03 | Bayer Ag | Fungicidal 1-acyl-benzimidazoline compositions and methods of use |
| US3808204A (en) * | 1973-01-12 | 1974-04-30 | Morton Norwich Products Inc | 1-((5-nitrofurfurylidene)amino)hexahydrobenzimidazol-2(3h)-one |
| CN101307023A (en) * | 2008-05-23 | 2008-11-19 | 东营市天正化工有限公司 | Production process of 5-acetyl acetamino benzimidazolone |
| CN101759649A (en) * | 2008-12-23 | 2010-06-30 | 西北农林科技大学农药研究所 | Benzimidazole amide bactericide |
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2011
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3499085A (en) * | 1966-10-04 | 1970-03-03 | Bayer Ag | Fungicidal 1-acyl-benzimidazoline compositions and methods of use |
| US3808204A (en) * | 1973-01-12 | 1974-04-30 | Morton Norwich Products Inc | 1-((5-nitrofurfurylidene)amino)hexahydrobenzimidazol-2(3h)-one |
| CN101307023A (en) * | 2008-05-23 | 2008-11-19 | 东营市天正化工有限公司 | Production process of 5-acetyl acetamino benzimidazolone |
| CN101759649A (en) * | 2008-12-23 | 2010-06-30 | 西北农林科技大学农药研究所 | Benzimidazole amide bactericide |
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