CN1272333C - 2-pyridyl-1H-benzimidazole-4-amide derivatives - Google Patents
2-pyridyl-1H-benzimidazole-4-amide derivatives Download PDFInfo
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- CN1272333C CN1272333C CN 200410084296 CN200410084296A CN1272333C CN 1272333 C CN1272333 C CN 1272333C CN 200410084296 CN200410084296 CN 200410084296 CN 200410084296 A CN200410084296 A CN 200410084296A CN 1272333 C CN1272333 C CN 1272333C
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Abstract
The present invention provides 2-pyridyl-1H-benzimidazole-4-amide derivatives whose chemical structural formula is shown as the specification. In the formula, R respectively represents F, Cl, Br, CH3, OH, NO2 and H. The derivatives have good efficiency for resisting viruses and ability for potentially inhibiting PARP [polyadenylic acid (ADP-ribose)polymerase]. Thus, the derivatives can be used to develop new medicines for resisting cancer.
Description
Technical field:
The present invention relates to a kind of 2-pyridyl-1H-benzoglyoxaline-4-acidamide type derivative, they have good antiviral effect (coxsackie B 3 viruses).
Background technology:
Along with the raising day by day of people's living standard, people more and more pay attention to healthy, are used to simultaneously to prevent and to treat the R and D development of disease medicament more and more faster.
The William A.Denny of Auckland, NZL pharmaceutical university etc. are in J.Med.Chem. (1990.33.814-819) preparation of the series compound of having reported following structure of publishing an article, and point out that it has good antitumous effect.
R
1Representative:
Roger John Griffin etc. report in patent US6100283 and have synthesized the series compound of following structure, and point out that they are good PARP[poly (ADP-ribose) polysaccharases] inhibitor, have good anticancer effect.
More than two pieces of articles illustrated that all benzimidazoles derivative has good biological activity.Yet, though more than two pieces of articles the influence of 2 bit substituents in the benzimidazole structure to the property of medicine has been discussed, the modification of the 4 bit substituents influence to the compound property of medicine is not appeared in the newspapers.
Summary of the invention:
The present invention introduces the alkali subtituent pyridyl on this basis in the 2-position; it and proteinic avidity are strengthened; has better biological activity; and modification at benzoglyoxaline 4-position acyl group; a series of compounds (its general structure is as follows) have been designed and synthesized; and its antiviral (coxsackie B 3 viruses) effect tested, find that they have good antiviral effect.
The chemical structural formula of a kind of 2-pyridyl of the present invention-1H-benzoglyoxaline-4-acidamide type derivative is as follows:
In the formula: the X representative
The Y representative
Wherein, R can represent F respectively, Cl, Br, CH
3, OH, NO
2, H.
This patent is a starting raw material with 2-glycyl-3-nitrobenzoic acid; process ammonia is separated, Hoffman degrades, reduction preparation 2; the 3-diaminobenzoic acid; then 2; the condensation under the neutralized verdigris effect of 3-diaminobenzoic acid and pyridine aldehydes gets 2-pyridyl-1H-benzoglyoxaline-4-carboxylic acid; last 2-pyridyl-1H-benzoglyoxaline-4-carboxylic acid and thionyl chloride effect obtain acyl chlorides, obtain final a series of product 2-pyridyl-1H-benzoglyoxaline-4-acidamide type derivative with the amine condensation again.
It is as shown in the table that anti-coxsackie B 3 virus activities of 2-pyridyl-1H-benzoglyoxaline-4-acidamide type derivative carry out test result:
In the table: "-" expression sample is at maximal non-toxic dosage nonreactive coxsackie B 3 virus activities.
IC
50Expression is to viral half-inhibition concentration.
RBV is a Ribavirina,
As seen from the above table, 2-pyridyl-1H-benzoglyoxaline-4-acidamide type derivative has good anti-coxsackie B 3 virus activities.
Description of drawings:
Fig. 1 is the HMNR nuclear magnetic spectrogram of the product of embodiment 12.
Fig. 2 is the HMNR nuclear magnetic spectrogram of the product of embodiment 15.
Fig. 3 is the HMNR nuclear magnetic spectrogram of the product of embodiment 22.
Embodiment:
EXAMPLE l: 2,3-diaminobenzoic acid synthetic
The-step, 2-glycyl-3-nitrobenzoic acid synthetic
The adjacent dibenzoic acid acid anhydride of 30g3-nitro is added in the strong aqua of 45ml in batches, be heated to 60 ℃, be incubated 2 hours.Needle crystal is separated out in cooling.Crystallization gets white solid, the product 2-glycyl of filtration drying-3-nitrobenzoic acid 29.4g with excessive slightly hcl acidifying.
Second step, 2-amino-3-nitrobenzoic acid synthetic
The bromine of 13.9g is splashed under 0 ℃ in the aqueous solution of 100ml of 7.3g sodium hydroxide.Add 17g2-glycyl-3-nitrobenzoic acid then.Be heated to 80 ℃, reaction system is separated out a large amount of red solid.Filter, the red solid acidifying is got yellow product, the dry 2-amino-3-nitrobenzoic acid 13.7g that gets.Thick product can get yellow needle-like crystal with the hot water recrystallization.
The 3rd step, 2,3-diaminobenzoic acid synthetic
2-amino-3-nitrobenzoic acid of 3g is joined in the methyl alcohol of 30ml, splash into equimolar 20% aqueous sodium hydroxide solution, raw material is dissolved fully, add the Raney Ni of 0.2g, reflux.Splash into 80% hydrazine hydrate (about 1.5eq * 1.1) then to yellow completely dissolve, filtered while hot is fallen Raney Ni.Mother liquor concentrates acidifying redness 2,3-diaminobenzoic acid 2.3g.Thick product can further separate purification with column chromatography.
Synthesizing of embodiment 2～4:2-pyridyl-1H-benzoglyoxaline-4-carboxylic acid
Synthesizing of embodiment 2:2-(4-pyridyl)-1H-benzoglyoxaline-4-carboxylic acid
With 1g2, the 3-diaminobenzoic acid is dissolved in the methyl alcohol of 50ml, under agitation drips the 20ml methanol solution of the 4-pyridine aldehydes of 1.4g.Then with 2.6g neutralized verdigris (Cu (Ac)
2H
2O) the 30ml aqueous solution splashes in the top reaction system, reflux 2 hours.Filtered while hot, filter cake washes with water.Use the mixed solution dissolving filter cake of the concentrated hydrochloric acid of 50ml methyl alcohol and 2.5ml then, splash into excessive slightly sodium sulfide solution, be heated to boiling.Filtered while hot is fallen copper sulfide precipitation.Mother liquor hydro-oxidation sodium is transferred slightly acidic, thin up, concentrate thick product, get 2-(4-pyridyl)-1H-benzoglyoxaline-4-carboxylic acid with column chromatography purification.Productive rate about 56%.
Product structure is identified:
1HMNR(DMSO，400MHz)δ：7.34-7.38(t，1H)，7.86-7.87(d，1H)，7.94-7.96(d，1H)，8.26-8.27(d，2H)，8.75(s，2H).MS：M
+＝239.
Synthesizing of embodiment 3:2-(3-pyridyl)-1H-benzoglyoxaline-4-carboxylic acid
By example 2 method Synthetic 2s-(3-pyridyl)-1H-benzoglyoxaline-4-carboxylic acid, productive rate about 60%.
Product structure is identified:
1HMNR(DMSO，400MHz)δ：7.20-7.24(t，1H)，7.50-7.56(m，1H)，7.76-7.85(m，2H)，8.57-8.66(m，2H)，9.42(s，1H).MS：M
+＝239.
Synthesizing of embodiment 4:2-(2-pyridyl)-1H-benzoglyoxaline-4-carboxylic acid
By example 2 method Synthetic 2s-(2-pyridyl)-1H-benzoglyoxaline-4-carboxylic acid, productive rate about 62%.
Product structure is identified:
1HMNR(DMSO，400MHz)δ：7.14-7.17(m，1H)，7.20-7.24(t，1H)，7.35-7.40(m，2H)，7.85-7.87(d，1H)，7.90-7.94(d，1H)，8.63-8.66(t，1H).MS：M
+＝239.
Synthesizing of embodiment 5～14:2-(4-pyridyl)-1H-benzoglyoxaline-4-amide derivatives
Synthetic 2-(4-the pyridyl)-1H-benzoglyoxaline-4-carboxylic acid of getting 0.2g of embodiment 5:2-(4-pyridyl)-1H-benzoglyoxaline-4-(N-phenyl) acid amides, the sulfur oxychloride of adding 5ml, reflux 2 hours.After reaction finishes, steam unnecessary sulfur oxychloride.It is standby that suspension liquid is made in the tetrahydrofuran (THF) stirring of adding 25ml.Aniline (1.1eq) and triethylamine (2eq) are dissolved in the methylene dichloride of 15ml, and under agitation the suspension liquid that will prepare above splashes into wherein.Stirring at room 2 hours.Solvent evaporated adds ethyl acetate extraction.Organic phase is used alkali lye and water washing respectively, and solvent evaporated gets 2-(4-pyridyl)-1H-benzoglyoxaline-4-(N-phenyl) acid amides.Thick product can be further purified productive rate about 92% with column chromatography.
Product structure is identified:
1HMNR(DMSO，400MHz)δ：7.13-7.17(t，1H)，7.41-7.50(m，3H)，7.86-7.90(t，3H)，8.01-8.03(d，1H)，8.20-8.22(d，2H)，8.84-8.85(d，2H)，12.05(s，1H).MS：M
+＝314.
Synthesizing of embodiment 6:2-(4-pyridyl)-1H-benzoglyoxaline-4-(N-rubigan) acid amides
By example 6 Synthetic 2s-(4-pyridyl)-1H-benzoglyoxaline-4-(N-rubigan) acid amides, productive rate about 90%.
Product structure is identified:
1HMNR(DMSO，400MHz)δ：7.47-7.52(m，3H)，7.88-7.90(d，1H)，7.93-7.96(d，2H)，8.22-8.23(d，2H)，8.85(s，2H)，12.08(s，1H)，13.96(s，1H).MS：M
+＝348.
Synthesizing of embodiment 7:2-(4-pyridyl)-1H-benzoglyoxaline-4-(N-hydroxyethyl) acid amides
By example 6 Synthetic 2s-(4-pyridyl)-1H-benzoglyoxaline-4-(N-hydroxyethyl) acid amides, productive rate about 92%.
Product structure is identified:
1HMNR(DMSO，400MHz)δ：3.54-3.57(q，2H)，3.63-3.67(q，2H)，4.96-4.98(t，1H)，7.39-7.43(t，1H)，7.77-7.79(t，1H)，7.90-7.93(t，1H)，8.18-8.19(d，2H)，8.80(s，1H)，10.09-10.12(t，1H)，13.75(s，1H).MS：M
+＝282.
Synthesizing of embodiment 8:2-(4-pyridyl)-1H-benzoglyoxaline-4-(the adjacent fluorophenyl of N-) acid amides
By example 6 Synthetic 2s-(4-pyridyl)-1H-benzoglyoxaline-4-(the adjacent fluorophenyl of N-) acid amides, productive rate about 89%.
Product structure is identified:
1HMNR(DMSO，400MHz)δ：7.12-7.18(m，1H)，7.23-7.27(t，1H)，7.39-7.45(m，2H)，7.85-7.87(d，1H)，7.98-8.00(d，1H)，8.19-8.21(m，2H)，8.62-8.66(m，1H)，8.80-8.82(d，2H)，12.58(s，1H).MS：M
+＝332.
Synthesizing of embodiment 9:2-(4-pyridyl)-1H-benzoglyoxaline-4-(bromophenyl between N-) acid amides
By example 6 Synthetic 2s-(4-pyridyl)-1H-benzoglyoxaline-4-(bromophenyl between N-) acid amides, productive rate about 88%.
Product structure is identified:
1HMNR(DMS0，400MHz)δ：7.33-7.35(d，1H)，7.38-7.42(t，1H)，7.47-7.51(t，1H)，7.64-7.66(d，1H)，7.87-7.89(d，1H)，8.00-8.02(d，1H)，8.21-8.22(d，2H)，8.39(s，1H)，8.84-8.85(d，2H)，12.08(s，1H)，13.95(s，1H)MS：M
+＝393.
Synthesizing of embodiment 10:2-(4-pyridyl)-1H-benzoglyoxaline-4-(N-o-methyl-phenyl-) acid amides
By example 6 Synthetic 2s-(4-pyridyl)-1H-benzoglyoxaline-4-(N-o-methyl-phenyl-) acid amides, productive rate about 91%.
Product structure is identified:
1HMNR(DMSO，400MHz)δ：2.59(s，3H)，7.06-7.10(t，1H)，7.24-7.27(t，1H)，7.31-7.33(d，1H)，7.48-7.51(t，1H)，7.86-7.89(d，1H)，8.06-8.08(d，1H)，8.13-8.15(d，2H)，8.31-8.33(d，1H)，8.82-8.84(d，2H)，11.60(s，1H)，13.96(s，1H).MS：M
+＝326.
Synthesizing of embodiment 11:2-(4-pyridyl)-1H-benzoglyoxaline-4-(N-p-nitrophenyl) acid amides
By example 6 Synthetic 2s-(4-pyridyl)-1H-benzoglyoxaline-4-(N-p-nitrophenyl) acid amides, productive rate about 87%.
Product structure is identified:
1HMNR(DMSO，400MHz)δ：7.50-7.54(t，1H)，7.91-7.93(d，1H)，8.04-8.06(d，1H)，8.14-8.17(d，2H)，8.23-8.25(m，2H)，8.31-8.34(m，2H)，8.85-8.87(m，2H)，12.48(s，1H)，14.00(s，1H).MS：M
+=359.
Synthesizing of embodiment 12:2-(4-pyridyl)-1H-benzoglyoxaline-4-(hydroxy phenyl between N-) acid amides
By example 6 Synthetic 2s-(4-pyridyl)-1H-benzoglyoxaline-4-(hydroxy phenyl between N-) acid amides, productive rate about 92%.
Product structure is identified:
1HMNR(DMSO，400MHz)δ：6.53-6.56(m，1H)，7.20-7.21(d，2H)，7.46-7.51(m，2H)，7.85-7.88(d，1H)，8.01-8.03(d，1H)，8.18-8.20(d，2H)，8.85-8.87(d，2H)，9.54(s，1H)，11.98(s，1H)，13.94(s，1H).MS：M
+＝330.
Synthesizing of embodiment 13:2-(4-pyridyl)-1H-benzoglyoxaline-4-(N-o-hydroxy-phenyl) acid amides
By example 6 Synthetic 2s-(4-pyridyl)-1H-benzoglyoxaline-4-(N-o-hydroxy-phenyl) acid amides, productive rate about 90%.
Product structure is identified:
1HMNR(DMSO，400MHz)δ：6.82-8.86(t，1H)，6.93-7.01(m，2H)，7.45-7.50(t，1H)，7.84-7.86(d，1H)，8.03-8.05(d，1H)，8.32-8.34(m，2H)，8.57-8.59(t，2H)，8.81-8.8?3(d，2H)，10.38(s，1H)，12.43(s，1H)，13.88(s，1H).MS：M
+＝330.
Synthesizing of embodiment 14:2-(4-pyridyl)-1H-benzoglyoxaline-4-(N-(3-methoxy acyl group-4-benzoyloxy group phenyl)) acid amides
By example 6 Synthetic 2s-(4-pyridyl)-1H-benzoglyoxaline-4-(N-(3-methoxy acyl group-4-benzoyloxy group phenyl)) acid amides, productive rate about 85%.
Product structure is identified:
1HMNR(DMSO，400MHz)δ：3.73(s，3H)，7.47-7.54(m，2H)，7.60-7.64(t，2H)，7.74-7.80(m，1H)，7.90-7.92(d，1H)，8.04-8.08(m，2H)，8.13-8.17(m，2H)，8.24-8.27(d，2H)，8.73-8.79(m，1H)，8.85-8.87(d，2H)，12.20(s，1H)，13.99(s，1H).MS：M
+＝492.
Synthesizing of embodiment 15～182-(2-pyridyl)-1H-benzoglyoxaline-4-amide derivatives
Synthetic 2-(2-the pyridyl)-1H-benzoglyoxaline-4-carboxylic acid of getting 0.2g of embodiment 15:2-(2-pyridyl)-1H-benzoglyoxaline-4-acid amides, the sulfur oxychloride of adding 5ml, reflux 2 hours.After reaction finishes, steam unnecessary sulfur oxychloride.The tetrahydrofuran (THF) that adds 25ml stirs makes suspension liquid.Then this suspension liquid is splashed in the ammoniacal liquor of 20ml under condition of stirring.Stirring at room 2 hours.Steam organic solvent, add ethyl acetate extraction.Organic phase water washing, solvent evaporated get 2-(2-pyridyl)-1H-benzoglyoxaline-4-acid amides.Thick product can be further purified productive rate about 90% with column chromatography.
Product structure is identified:
1HMNR(DMSO，400MHz)δ：7.34-7.38(t，1H)，7.55-7.59(m，1H)，7.71-7.73(m，1H)，7.81-7.82(d，1H)，7.87-7.89(m，1H)，8.00-8.05(m，1H)，8.43-8.45(m，1H)，8.75-8.78(m，1H)，9.27-9.28(d，1H)，13.59(s，1H).MS：M
+＝238.
Synthesizing of embodiment 16:2-(2-pyridyl)-1H-benzoglyoxaline-4-(N-phenyl) acid amides
By example 6 Synthetic 2s-(2-pyridyl)-1H-benzoglyoxaline-4-(N-phenyl) acid amides, productive rate about 88%.
Product structure is identified:
1HMNR(CDCl
3，400MHz)δ：7.14-7.18(t，1H)，7.41-7.47(m，4H)，7.64-7.66(d，1H)，7.92-8.00(m，3H)，8.27-8.29(d，1H)，8.45-8.47(d，1H)，8.67-8.69(m，1H)，11.07(s，1H)，12.11(s，1H).MS：M
+＝314.
Synthesizing of embodiment 17:2-(2-pyridyl)-1H-benzoglyoxaline-4-(the adjacent fluorophenyl of N-) acid amides
By example 6 Synthetic 2s-(2-pyridyl)-1H-benzoglyoxaline-4-(the adjacent fluorophenyl of N-) acid amides, productive rate about 87%.
Product structure is identified:
1HMNR(DMSO，400MHz)δ：7.14-7.19(m，1H)，7.24-7.28(m，1H)，7.40-7.48(m，2H)，7.60-7.63(m，1H)，7.80-7.83(d，1H)，8.02-8.04(d，1H)，8.12-8.16(t，1H)，8.45-8.47(d，1H)，8.64-8.68(t，1H)，8.80-8.81(d，1H)，12.52(s，1H)，13.84(s，1H).MS：M
+＝332.
Synthesizing of embodiment 18:2-(2-pyridyl)-1H-benzoglyoxaline-4-(N-hydroxyethyl) acid amides
By example 6 Synthetic 2s-(2-pyridyl)-1H-benzoglyoxaline-4-(N-hydroxyethyl) acid amides, productive rate about 86%.
Product structure is identified:
1HMNR(DMSO，400MHz)δ：3.52-3.57(q，2H)，3.63-3.67(q，2H)，4.98-5.00(t，1H)，7.34-7.38(t，1H)，7.56-7.59(m，1H)，7.69-7.72(d，1H)，7.87-7.90(d，1H)，8.02-8.06(m，1H)，8.45-8.47(d，1H)，8.76-8.77(m，1H)，10.14-10.16(t，1H)，13.62(s，1H).
MS：M
+=282.
Synthesizing of embodiment 19～22 2-(3-pyridyl)-1H-benzoglyoxaline-4-amide derivatives
Synthesizing of embodiment 19:2-(3-pyridyl)-1H-benzoglyoxaline-4-acid amides
By example 16 Synthetic 2s-(3-pyridyl)-1H-benzoglyoxaline-4-acid amides, productive rate about 93%.
Product structure is identified:
1HMNR(DMSO，400MHz)δ：7.35-7.40(t，1H)，7.60-7.63(m，1H)，7.76-7.80(m，2H)，7.87-7.90(d，1H)，8.56-8.59(m，1H)，8.71-8.72(d，1H)，9.26(s，1H)，9.40(s，1H)，13.60(s，1H).MS：M
+238.
Synthesizing of embodiment 20:2-(3-pyridyl)-1H-benzoglyoxaline-4-(N-phenyl) acid amides
By example 6 Synthetic 2s-(3-pyridyl)-1H-benzoglyoxaline-4-(N-phenyl) acid amides, productive rate about 91%.
Product structure is identified:
1HMNR(DMSO，400MHz)δ：7.13-7.16(t，1H)，7.42-7.48(m，3H)，7.67-7.70(m，1H)，7.84-7.90(m，3H)，8.00-8.02(d，1H)，8.62-8.65(m，1H)，8.76-8.77(d，1H)，9.47(s，1H)，12.12(s，1H)，13.80(s，1H).MS：M
+＝314.
Synthesizing of embodiment 21:2-(3-pyridyl)-1H-benzoglyoxaline-4-(the adjacent fluorophenyl of N-) acid amides
By example 6 Synthetic 2s-(3-pyridyl)-1H-benzoglyoxaline-4-(the adjacent fluorophenyl of N-) acid amides, productive rate about 86%.
Product structure is identified:
1HMNR(DMSO，400MHz)δ：7.12-7.16(m，1H)，7.22-7.25(t，1H)，7.38-7.42(m，2H)，7.69-7.73(m，1H)，7.83-7.86(d，1H)，7.92-7.95(d，1H)，8.02-8.05(m，1H)，8.43-8.46(d，1H)，8.63-8.66(t，1H)，8.73-8.76(d，1H)，12.48(s，1H)，13.64(s，1H).MS：M
+＝322.
Synthesizing of embodiment 22:2-(3-pyridyl)-1H-benzoglyoxaline-4-(N-hydroxyethyl) acid amides
By example 6 Synthetic 2s-(3-pyridyl)-1H-benzoglyoxaline-4-(N-hydroxyethyl) acid amides, productive rate about 89%.
Product structure is identified:
1HMNR(DMSO，400MHz)δ：3.52-3.56(q，2H)，3.63-3.65(q，2H)，4.92-4.84(t，1H)，7.35-7.39(t，1H)，7.60-7.63(t，1H)，7.74-7.76(d，1H)，7.88-7.93(t，1H)，8.5-8.59(m，1H)，8.71-8.73(d，1H)，9.45(s，1H)，10.11-10.14(t，1H)，13.57(s，1H).MS：M
+＝282.
Claims (1)
1, a kind of 2-pyridyl-1H-benzoglyoxaline-4-acidamide type derivative is characterized in that chemical structural formula is as follows:
In the formula: the X representative
The Y representative
-CH
2CH
2OH,
Wherein, R can represent F respectively, Cl, Br, CH
3, OH, NO
2, H.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010078830A1 (en) * | 2009-01-08 | 2010-07-15 | 上海交通大学 | Benzimidazole-4-carboxamide derivatives, their preparation methods, pharmaceutical compositions and their uses |
| CN101353342B (en) * | 2008-09-11 | 2012-06-13 | 上海交通大学 | 2-pyridinyl-1H-benzimidazole-4-acidamide type derivative |
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| JP5758292B2 (en) | 2008-07-03 | 2015-08-05 | サートリス ファーマシューティカルズ， インコーポレイテッド | Benzimidazoles and related analogs as sirtuin modulators |
| CN101434601B (en) * | 2008-07-24 | 2010-09-29 | 上海交通大学 | 2-furyl-1H-benzimidazole-4-acidamide type derivative |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101353342B (en) * | 2008-09-11 | 2012-06-13 | 上海交通大学 | 2-pyridinyl-1H-benzimidazole-4-acidamide type derivative |
| WO2010078830A1 (en) * | 2009-01-08 | 2010-07-15 | 上海交通大学 | Benzimidazole-4-carboxamide derivatives, their preparation methods, pharmaceutical compositions and their uses |
| JP2012514607A (en) * | 2009-01-08 | 2012-06-28 | シャンハイ ジアオ トン ユニバーシティ | Benzimidazole-4-carboxamide derivative and method for producing the same, drug mixture and use thereof |
| RU2558328C2 (en) * | 2009-01-08 | 2015-07-27 | Шанхай Цзяо Тун Юниверсити | Banzimidazol-4-amide derivatives, methods for producing them, based pharmaceutical compositions and using them as coxsackie virus agent |
| EP2963033A1 (en) * | 2009-01-08 | 2016-01-06 | Shanghai Jiao Tong University | Benzimidazole-4-carboxamide derivates, their preparation methods, pharmaceutical compositions and their uses |
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