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以3-甲磺酰胺基-4-苯氧基苯甲醚为原料,在AlCl3作用下,经付-克乙酰化同时脱甲基化反应得到(2-羟基-4-甲磺酰胺基-5-苯氧基)苯乙酮,再经溴化得到标题化合物,总收率70%。 相似文献
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4-色满酮Mannich碱类化合物的合成及其抗炎活性 总被引:5,自引:0,他引:5
目的设计合成一些4-色满酮Mannich类化合物,并且考察其抗炎活性.方法以取代的4-色满酮为原料,经过Mannich反应合成4-色满酮Mannich碱类化合物,并测定了目标化合物的抗炎活性.结果合成了17种4-色满酮Mannich碱类化合物,并经元素分析、红外光谱、核磁共振氢谱确证这些化合物的结构,药理活性筛选结果表明:大多数化合物具有显著的抗炎活性. 相似文献
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目的 设计并合成4-苯甲酰胺基苯磺酰胺类化合物,研究其抗炎活性和构效关系。方法 以取代苯甲酸为原料合成目标化合物,并以二甲苯致小鼠耳肿胀模型测试目标化合物的抗炎活性。结果 共合成7个化合物(其中6个化合物未见CA报道),经红外光谱、核磁共振氢谱和质谱确证其结构,部分化合物对二甲苯致耳肿胀具有较强的抑制作用,并初步总结了构效关系。结论 4-苯甲酰胺基苯磺酰胺类化合物具有较强的抗炎活性。 相似文献
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目的: 在研究非糖类α-糖苷酶抑制剂的过程中,发现3-(4-苯磺酰氨基)苯甲酰基-2H-1-苯并吡喃-2-酮类化合物具有显著的α-糖苷酶抑制活性。为进一步探讨该类化合物的构效关系,将4-位的苯磺酰氨基替换为甲磺酰氨基和乙酰氨基,合成3-(4-甲磺酰胺基/乙酰基)苯甲酰基-2H-1-苯并吡喃-2-酮类化合物,并评价其α-糖苷酶抑制活性。 方法: 以4-硝基苯甲酸为原料,经氯代、酰化、水解、还原反应制得4-氨基-β-氧代苯丙酸乙酯,与甲磺酰氯/乙酰氯经酰化反应得4-甲磺酰氨基/乙酰氨基-β-氧代苯丙酸乙酯,再与取代水杨醛经Knoevernagel缩合,同时环合得到目标化合物。采用酵母α-葡萄糖苷酶对所合成的目标化合物进行α-糖苷酶抑制活性评价。 结果: 合成了22个目标化合物,结构经1H-NMR和IR确证。大部分3-(4-甲磺酰氨基/乙酰氨基)苯甲酰基-2H-1-苯并吡喃-2-酮类化合物未表现出α-糖苷酶抑制活性,只有化合物3-(4-甲磺酰氨基)苯甲酰基-6,8-二叔丁基-2H-1-苯并吡喃-2-酮(10f)表现出良好的α-糖苷酶抑制活性,IC50值为10.16 μmol﹒L-1。 结论: 对于3-苯甲酰基-2H-1-苯并吡喃-2-酮类化合物,其苯甲酰基以4-位甲磺酰氨基/乙酰氨基取代对该类化合物的α-糖苷酶抑制活性不利,该类化合物的构效关系值得进一步研究。 相似文献
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《中国药房》2019,(3):318-322
目的:设计、合成N-芳酰基取代的二氢吲哚-3-乙酸类衍生物,并评价其体外降糖活性。方法:以吲哚衍生物2-[5-(苄氧基)-1-(4-氯苯甲酰基)-2-甲基-1H-吲哚-3-基]乙酸(GY3)为先导化合物,以4-苯甲氧基苯肼盐酸盐及4-氧戊酸甲酯为原料,经Fischer吲哚环合、还原、酰胺化及水解等4步反应得到8种N-芳酰基(3-羟基苯甲酰基、3-氰基苯甲酰基、4-硝基苯甲酰基、4-甲磺酰基苯甲酰基、4-乙酰胺基苯甲酰基、3-乙酰氨基苯甲酰基、异烟酰基、吡啶-2-甲酰基)取代的二氢吲哚-3-乙酸类衍生物。采用人肝癌细胞HepG2测试目标化合物的体外促葡萄糖消耗活性。结果:共合成8个N-芳酰基取代的二氢吲哚-3-乙酸类目标化合物,其结构均经质谱、核磁共振氢谱及碳谱确证。在1.0μmol/L条件下,所合成化合物在HepG2细胞上的促葡萄糖消耗百分率为5.4%~9.1%,其中,2-[(2R,3S)-5-苄氧基-2-甲基-1-(4-甲磺酰基苯甲酰基)-2,3-二氢-吲哚-3-基]乙酸的降糖活性最好,其促葡萄糖消耗百分率为(9.10±1.81)%,与阳性对照药物二甲双胍接近[(10.58±1.68)%],但仍弱于先导化合物GY3[(12.15±0.78)%]。结论:二氢吲哚类化合物的N-芳酰基芳环上引入不同吸电子取代基团,如氰基、硝基、甲磺酰基等,其降糖活性不同程度下降,且弱于卤素取代基的GY3。 相似文献
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Unlü S Onkol T Dündar Y Okçelik B Küpeli E Yeşilada E Noyanalpan N Sahin MF 《Archiv der Pharmazie》2003,336(8):353-361
In this study for developing potent analgesic and anti-inflammatory compounds, we synthesized 6-acyl-2-benzoxazolinone and 6-acyl-2-benzothiazolinone derivatives with acetic acid and propanoic acid side chain, and performed preliminary screening of their in vivo analgesic and anti-inflammatory activities at a single dose of 100 mg/kg inmice by a p-benzoquinone-induced writhing test and a Carrageenaninduced hind paw edema model, respectively. We also determined their gastric ulceration effects in the tested animals. Propanoic acid derivatives were generally found to have higher analgesic and anti-inflammatory activities, and among them, 3-(6-benzoyl-2-benzothiazolinon-3-yl)propanoic acid (Compound 4 a) exhibited the highest analgesic and anti-inflammatory activity. However, all compounds showed lower anti-inflammatory effects than we observed for indomethacin at 10 mg/kg dose. Consequently, 6-acyl-2-benzoxazolinone/2-benzothiazolinones having propanoic acid side chain might lead to further studies for developing better candidates with potent analgesic and anti-inflammatory effects while acetic acid derivatives do not exhibit comparable satisfactory features. 相似文献
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5,6-二芳基-2,3-二氢-1-吡咯里嗪酮类化合物的合成及抗炎镇痛活性 总被引:1,自引:0,他引:1
目的寻找高效低毒、有抗炎镇痛活性的新的吡咯里嗪酮类化合物。方法以二芳基取代杂环类COX-2选择性抑制剂为模板,以吡里酮为母体,设计并合成了5,6-二芳基-2,3-二氢-1-吡咯里嗪酮类化合物。用IR,1HNMR和MS确定其结构。用二甲苯致小鼠耳肿胀法和小鼠醋酸扭体法测定这些化合物的(po 200mg·kg-1)抗炎及镇痛活性。结果合成了17个新化合物(1-17)。生物实验结果显示,多数化合物有一定的抗炎和(或)镇痛活性。结论化合物3,8,11,14和15抗炎活性优于对照药布洛芬;化合物9,10和11镇痛活性接近于对照药布洛芬,值得进一步研究。 相似文献
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The analgesic effects of pirprofen on bradykinin-induced flexor reflexes in rats and rabbits were investigated in comparison with those of indomethacin and ibuprofen by oral administrations. The bradykinin-induced flexor reflexes in rats were suppressed by pirprofen at 10 mg/kg-200 mg/kg, the effect reaching plateau at over 30 mg/kg. Suppression at the dose of 200 mg/kg was 56%. A similar dose-dependent curve was obtained for ibuprofen at 30 mg/kg-300 300 mg/kg. On the other hand, indomethacin exerted dose-dependent inhibition at 1 mg/kg-10 mg/kg without a tendency to reach the plateau effect within this dose range. Suppression at the dose of 10 mg/kg was 83%. The ED50 values of pirprofen, indomethacin and ibuprofen were 68 mg/kg, 3.3 mg/kg and 94 mg/kg, respectively. On the bradykinin-induced flexor reflexes in rabbits, pirprofen showed 60% suppression at the dose of 10 mg/kg, of which the effects were roughly equivalent to those of indomethacin and ibuprofen at the same dosage. These results indicate that there is a species difference concerning the three drug activities on bradykinin-induced flexor reflexes between the rat and the rabbit. 相似文献
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2,4-二氨基-5-甲基-6-取代苄氨基喹唑啉衍生物的合成及其抗疟和抗肿瘤作用 总被引:2,自引:0,他引:2
本文报道2,4-二氨基-5-甲基-6-取代苄氨基喹唑啉衍生物的合成及其抗疟和抗肿瘤活性。这类化合物由5-甲基-2,4,6-三氨基喹唑啉与相应的取代苯甲醛缩合成Schiff碱,然后经还原,甲酰化或亚硝化制得。经对伯氏鼠疟原虫(Plasmodium berghei)抑制性治疗筛选,有三个化合物Ⅳ_(2,5,6)剂量5mg/kg×4d抑制率为100%;体外抗肿瘤活性以Ⅱ_7和Ⅳ_8最强,对L1210白血病细胞株的IC_(50)分别为3.910×10~(-3)μg/ml和6.172×10~(-3)μg/ml,与MTX相当。 相似文献
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The effects of a potent non-steroidal antiinflammatory drug, indomethacin, on the inflammatory response and lymphocyte proliferation were investigated in adjuvant-arthritic rats. As shown by others, adjuvant produced a time-dependent swelling of the contralateral paw which was maximal within 14 days after administration. Upon the intraperitoneal injection of either 1 or 2 mg/kg of indomethacin, twice daily for 3 days, the swelling of the contralateral paw was completely reduced. Selective changes in proliferative responses of splenic T and B lymphocytes to mitogens were found to accompany these effects. Adjuvant arthritic rats were found to have increased T cell proliferation when stimulated with phytohemagglutinin, whereas proliferation of B lymphocytes in the presence of lipopolysaccharide was completely suppressed. Indomethacin treatment at either the 1 or 2 mg/kg dose was found to depress the proliferative responses of T cells by 60 and 95%, respectively. In contrast, the hyporesponsiveness of B lymphocytes in arthritic animals was partially reversed with 2 mg/kg indomethacin. These results suggest that indomethacin may be exerting an antiinflammatory effect through a selective alteration of T and B lymphocyte activities in lymphoid tissue. 相似文献
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Fourteen new 3-[2-(2- and/or 4-pyridyl)ethyl]benzoxazolinone derivatives have been synthesized by reacting 2- and/or 4-vinylpyridine and appropriate benzoxazolinones. Their chemical structures have been proven by IR, 1H-NMR, and elemental analysis. Analgesic activities of these compounds were investigated by a "Modified Koster's Test". Except for compounds 10 and 11, all the new derivatives showed higher analgesic activities than aspirin. Therefore the compounds were screened for their antiinflammatory activities using the carrageenan hind paw edema test. The compounds (6, 7, 8, 9, 14, and 17) that showed high antiinflammatory activity were then further screened for their ability to inhibit prostaglandin E2 (PGE2) induced paw edema. Although all the benzoxazolinone derivatives synthesized in this study showed higher antiinflammatory activity compared to indomethacin, those without a substituent at the 6-position of the ring were significantly more active than the rest of the group, and their ulcerogenic activities and ED50 values indicate them as promising derivatives for further study. 相似文献
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Süleyman H Yildirim D Aslan A Göçer F Gepdiremen A Güvenalp Z 《Biological & pharmaceutical bulletin》2002,25(1):10-13
In this study, the antiinflammatory effects of 50, 100 and 200 mg/kg doses of extract obtained from Cladonia rangiformis, so-called C-1, were investigated. The effects of C-1 on the acute phase of inflammation were studied in formaldehyde-induced edema. A cotton-pellet granuloma test was used to investigate the effects of C-1 on chronic inflammation. The antiedema potency of C-1 was compared with indomethacin. C-1 at the doses mentioned above showed 33.8% (p<0.005), 36.1% (p<0.005), 43.1% (p<0.001) inhibition, respectively. The corresponding antiinflammatory effect for indomethacin was determined as 72% (p<0.001). 200 mg/kg C-1 and 10 mg/kg indomethacin decreased the formation of granuloma tissue induced by cotton-pellet method at a rate of 57.3% (p<0.005) and 52.1% (p<0.005), respectively. It was seen that C-1 was more effective on chronic inflammation than on acute inflammation. 相似文献
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A series of cis- and trans-6,6a,7,8,9,10,10a,11-octahydro-11- oxodibenzo[b,e]thiepinacetic acids (6-9) and -oxepinacetic acids (10-13) were prepared and their antiinflammatory activity was examined in the rat carrageenan hind paw edema test. The antiinflammatory activity of these compounds depended on their stereochemical features (C6a, C10a, and C2'). The 6a,10a-trans compounds exhibited considerable antiinflammatory activity, whereas the 6a,10a-cis compounds were inactive. Among the trans compounds, 6,6a,7,8,9,10,10a,11-octahydro-11-oxodibenzo[b,e]thiepin-3-p ropionic acid (9a) and its oxepin analogue (13a) showed an antiinflammatory activity superior to that of indomethacin. The phenethyl ester (25) of 9a showed potent antiinflammatory activity, and its safety index (UD50/ED50) was over 14 times higher than that of indomethacin. The phenethyl ester (25) is the most favorable compound with high antiinflammatory activity and little ulcerogenicity. 相似文献
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Starting from 3-substituted-1,2,4-triazole-5-thiones (la-h), eight new 5-carbomethoxy-2-substituted-7H-1,2,4-triazolo[3,2-b]-1,3-thiazine-7-ones (2a-h) were synthesized and characterized by spectral and elementary analysis. The obtained compounds were submitted to preliminary pharmacological assay to evaluate their antiinflammatory and analgesic activities as well as gastrointestinal irritation liability and acute toxicity. Among the compounds studied, compounds 2c, 2d, 2e and 2h showed most remarkable antiinflammatory activity in the carrageenan and serotonin induced edema and in the inhibition of castor oil-induced diarrhea tests. The analgesic activity of these active compounds correlated with their antiinflammatory activities in the inhibition of acetic acid-induced writhing test. In gastric ulceration studies, the compounds were found safety at low dose levels (10 and 20 mg/kg). 相似文献
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F Clemence O Le Martret F Delevallee J Benzoni A Jouanen S Jouquey M Mouren R Deraedt 《Journal of medicinal chemistry》1988,31(7):1453-1462
A series of 4-hydroxy-3-quinolinecarboxamides has been synthesized and evaluated by the oral route as antiinflammatory agents in carrageenin-induced foot edema and adjuvant-induced arthritis and as analgesic agents in the acetic acid induced writhing test. Among the most active molecules, some have shown both analgesic and acute antiinflammatory activities. Others, such as compounds 24, 37, and 52, were only powerful peripherally acting analgesics. Compound 52, being active at 1 mg/kg (ED50), is the most potent compound in the series. Some analogues, substituted in the 2-position by an alcohol, ester, or amine function, displayed potent antiarthritic activity in the same range as that of piroxicam and were also active in acute tests of inflammation and nociception. They inhibited the activity of both cyclooxygenase and 5-lipoxygenase at micromolar concentrations. Compound 102 (RU 43526) showed potent antiarthritic activity (adjuvant-induced arthritis, ED50 = 0.7 mg/kg, po) and gastrointestinal tolerance (ED100 greater than 250 mg/kg, po) and thus it is presently undergoing an extensive pharmacological evaluation. 相似文献