W. Hsu, Jing-Min Hwang, L. Hsu, Yung-Yun Huang, Kang-chien Liu
Starting from isatoic anhydride (1) and via one-pot process to 2-methylthio-3-phenylamino-quinazolin-4(3H)-one (4) was isolated in excellent yield. Hydrazinolysis of 4 converted it into the hydrazino derivative 5. Cyclocondensation of 5 with appropriate carboxylic acid orthoesters 6a-c, N,N’-carbonyl-, N,N’-thiocarbonyldiimidazole (6d,e), ethyl chloroformate, carbon disulfide, trifluoro- and trichloroacetic anhydride (6h,i) under elevated temperature gave 4-phenylamino-1「1,2,4」triazolo「2,3-a」 quinazolin-5(4H)-one (8a) and its 2-substituted derivatives 8b-g in different yields. These compounds activated satisfactory antihypertensive activity after the pharmacological evaluation on anesthetized rats.
{"title":"Guanidine-annelated Heterocycles XV. Synthesis of 2-Substituted 4-Phenylamino[1,2,4]triazolo-[2,3-a]quinazolin-5(4H)-ones as Potential Antihypertensive Agents^1","authors":"W. Hsu, Jing-Min Hwang, L. Hsu, Yung-Yun Huang, Kang-chien Liu","doi":"10.7019/CPJ.200306.0185","DOIUrl":"https://doi.org/10.7019/CPJ.200306.0185","url":null,"abstract":"Starting from isatoic anhydride (1) and via one-pot process to 2-methylthio-3-phenylamino-quinazolin-4(3H)-one (4) was isolated in excellent yield. Hydrazinolysis of 4 converted it into the hydrazino derivative 5. Cyclocondensation of 5 with appropriate carboxylic acid orthoesters 6a-c, N,N’-carbonyl-, N,N’-thiocarbonyldiimidazole (6d,e), ethyl chloroformate, carbon disulfide, trifluoro- and trichloroacetic anhydride (6h,i) under elevated temperature gave 4-phenylamino-1「1,2,4」triazolo「2,3-a」 quinazolin-5(4H)-one (8a) and its 2-substituted derivatives 8b-g in different yields. These compounds activated satisfactory antihypertensive activity after the pharmacological evaluation on anesthetized rats.","PeriodicalId":22409,"journal":{"name":"The Chinese Pharmaceutical Journal","volume":"15 1","pages":"185-196"},"PeriodicalIF":0.0,"publicationDate":"2003-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"90660471","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Approaches towards the preparation of 5,6,7-trimethoxyflavone (8), a key intermediate for the synthesis of baicalein, are discussed. Of the synthetic routes, the most efficient was accomplished by direct Fries acylation of trimethoxyphenol (1) with cinnamoyl chloride followed by oxidative cyclization of the resulting chalcone 6 with I 2 /DMSO in good overall yields (70%). Demethylation of 8 using 47% HBr/AcOH readily produced baicalein. The chalcone 6 could also be prepared by Claisen-Schmidt condensation of acetophenone 2 with benzaldehyde catalyzed in alkali.
{"title":"Synthesis of 5,6,7-Trimethoxyflavone as a Key Intermediate for the Preparation of Baicalein","authors":"Wen‐Hsin Huang, C. Yang, P. Chien, A. Lee","doi":"10.7019/CPJ.200304.0101","DOIUrl":"https://doi.org/10.7019/CPJ.200304.0101","url":null,"abstract":"Approaches towards the preparation of 5,6,7-trimethoxyflavone (8), a key intermediate for the synthesis of baicalein, are discussed. Of the synthetic routes, the most efficient was accomplished by direct Fries acylation of trimethoxyphenol (1) with cinnamoyl chloride followed by oxidative cyclization of the resulting chalcone 6 with I 2 /DMSO in good overall yields (70%). Demethylation of 8 using 47% HBr/AcOH readily produced baicalein. The chalcone 6 could also be prepared by Claisen-Schmidt condensation of acetophenone 2 with benzaldehyde catalyzed in alkali.","PeriodicalId":22409,"journal":{"name":"The Chinese Pharmaceutical Journal","volume":"15 1","pages":"101-107"},"PeriodicalIF":0.0,"publicationDate":"2003-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84322652","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Yu-Ling Huang, Fang-Hua Chow, B. Shieh, J. Ou, Chien‐Chih Chen
Two new anthraquinones, 7-hydroxy-1,2,8-trimethoxy-3-methylanthraquinone (1) and 7,8-dihydroxy-1,2-dimethoxy-3-methylanthraquinone (2), were isolated from the roots of Hemerocallis fulva. Their structures were established on the basis of spectral evidence (NMR and MS).
{"title":"Two New Anthraquinones from Hemerocallis fulva","authors":"Yu-Ling Huang, Fang-Hua Chow, B. Shieh, J. Ou, Chien‐Chih Chen","doi":"10.7019/CPJ.200302.0083","DOIUrl":"https://doi.org/10.7019/CPJ.200302.0083","url":null,"abstract":"Two new anthraquinones, 7-hydroxy-1,2,8-trimethoxy-3-methylanthraquinone (1) and 7,8-dihydroxy-1,2-dimethoxy-3-methylanthraquinone (2), were isolated from the roots of Hemerocallis fulva. Their structures were established on the basis of spectral evidence (NMR and MS).","PeriodicalId":22409,"journal":{"name":"The Chinese Pharmaceutical Journal","volume":"42 1","pages":"83-86"},"PeriodicalIF":0.0,"publicationDate":"2003-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"81035512","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Kuo-Ching Kao, Yu‐Ling Ho, F. Chueh, Jih P. Wang, Yuan-Shiun Chang
The methanolic extract of Strobilanthes formosanus was investigated for its antipyretic, analgesic and anti-inflammatory activities in animal models. In unanesthetized rats, the extract (100-1000 mg/kg, i.p.) caused a dose-related fall in colonic temperature at room temperature (24 ± 1℃). The fever induced by interleukin-1β(10 ng/10μL, lateral cerebral ventricle injection) was attenuated by treatment with the extract (50-1000 mg/kg, i.p.). However, the extract (1000 mg/kg) and acetaminophen (50 mg/kg) did not significantly attenuate pyrexia induced by PGE2 (200ng/10μL,i.c.v.). The extract significantly and dose-dependently inhibited the writhing response of mice and decreased the licking time in both the early and late phases of the formalin test. A significant (P＜0.05) inhibition of neutrophil degranulation induced by fMLP was also produced by the extract. This study established the antipyretic, analgesic and anti-inflammatory activities of S. formosanus.
{"title":"Antipyretic, Analgesic and Anti-inflammatory Activities of Strobilanthes formosanus","authors":"Kuo-Ching Kao, Yu‐Ling Ho, F. Chueh, Jih P. Wang, Yuan-Shiun Chang","doi":"10.7019/CPJ.200302.0055","DOIUrl":"https://doi.org/10.7019/CPJ.200302.0055","url":null,"abstract":"The methanolic extract of Strobilanthes formosanus was investigated for its antipyretic, analgesic and anti-inflammatory activities in animal models. In unanesthetized rats, the extract (100-1000 mg/kg, i.p.) caused a dose-related fall in colonic temperature at room temperature (24 ± 1℃). The fever induced by interleukin-1β(10 ng/10μL, lateral cerebral ventricle injection) was attenuated by treatment with the extract (50-1000 mg/kg, i.p.). However, the extract (1000 mg/kg) and acetaminophen (50 mg/kg) did not significantly attenuate pyrexia induced by PGE2 (200ng/10μL,i.c.v.). The extract significantly and dose-dependently inhibited the writhing response of mice and decreased the licking time in both the early and late phases of the formalin test. A significant (P＜0.05) inhibition of neutrophil degranulation induced by fMLP was also produced by the extract. This study established the antipyretic, analgesic and anti-inflammatory activities of S. formosanus.","PeriodicalId":22409,"journal":{"name":"The Chinese Pharmaceutical Journal","volume":"1 1","pages":"55-63"},"PeriodicalIF":0.0,"publicationDate":"2003-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"88661412","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Two biflavones, cupressuflavone (1) and amentoflavone (2), three flavonoids, luteolin 7-methyl ether (3), isoorientin (4) and 3'-methoxyluteolin 7-O-glucoside (5), as well as two acids, 4-caffeoylquinic acid (6) and 5-caffeoylquinic acid (7) were isolated from the aerial parts of Biophytum sensitivum. Their structures were established on the basis of spectroscopic data.
从Biophytum sensitivum的气生部位分离得到了两种双黄酮类化合物:柏素黄酮(1)和薄荷黄酮(2)，木犀草素7-甲基醚(3)、异荭草素(4)和3′-甲氧基木犀草素7- o -葡萄糖苷(5)，以及两种酸，4-咖啡酰奎宁酸(6)和5-咖啡酰奎宁酸(7)。根据光谱数据确定了它们的结构。
{"title":"Chemical constituents of Biophytum sensitivum","authors":"Yun-Lian Lin, Wan-Yi Wang","doi":"10.7019/CPJ.200302.0071","DOIUrl":"https://doi.org/10.7019/CPJ.200302.0071","url":null,"abstract":"Two biflavones, cupressuflavone (1) and amentoflavone (2), three flavonoids, luteolin 7-methyl ether (3), isoorientin (4) and 3'-methoxyluteolin 7-O-glucoside (5), as well as two acids, 4-caffeoylquinic acid (6) and 5-caffeoylquinic acid (7) were isolated from the aerial parts of Biophytum sensitivum. Their structures were established on the basis of spectroscopic data.","PeriodicalId":22409,"journal":{"name":"The Chinese Pharmaceutical Journal","volume":"4 1","pages":"71-75"},"PeriodicalIF":0.0,"publicationDate":"2003-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"86582164","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
A. G. Damu, P. Kuo, Y. Leu, Y. Chan, Tian-Shung Wu
Aristolochia is an important genus widely cultivated and used in traditional Chinese medicine. The genus has attracted much interest and has been the subject of numerous chemical studies. In the last twelve years, all the Formosan species of Aristolochia have been investigated by our group for their chemical constituents and biological activities. They are sources of a number of physiologically active compounds of different classes, and various types of phenanthrene derivatives, terpenes, alkaloids, flavonoids, lignoids, benzenoids, and steroids have been isolated from Formosan Aristolochia species. The nature of these constituents is compiled in this review together with their bioactivities in an effort to show the rapid development in the phytochemistry and the therapeutic applications of the Aristolochia species.
{"title":"Chemical Constituents and Pharmacology of the Formosan Aristolochia Species","authors":"A. G. Damu, P. Kuo, Y. Leu, Y. Chan, Tian-Shung Wu","doi":"10.7019/CPJ.200302.0001","DOIUrl":"https://doi.org/10.7019/CPJ.200302.0001","url":null,"abstract":"Aristolochia is an important genus widely cultivated and used in traditional Chinese medicine. The genus has attracted much interest and has been the subject of numerous chemical studies. In the last twelve years, all the Formosan species of Aristolochia have been investigated by our group for their chemical constituents and biological activities. They are sources of a number of physiologically active compounds of different classes, and various types of phenanthrene derivatives, terpenes, alkaloids, flavonoids, lignoids, benzenoids, and steroids have been isolated from Formosan Aristolochia species. The nature of these constituents is compiled in this review together with their bioactivities in an effort to show the rapid development in the phytochemistry and the therapeutic applications of the Aristolochia species.","PeriodicalId":22409,"journal":{"name":"The Chinese Pharmaceutical Journal","volume":"9 1","pages":"1-33"},"PeriodicalIF":0.0,"publicationDate":"2003-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"74710872","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Chien‐Chih Chen, Huimin Huang, Chien-Chang Shen, Yu-lin Huang, J. Ou
Four known flavone glucuronides, luteolin-7-O-β-D-glucuronide (8), apigenin-7-O-β-D-glucuronide (9), chrysoeriol-7-O-β-D-glucuronide (10) and hispidulin-7-O-β-D-glucuronide (11), and seven known phenolic compounds (1-7) were isolated from the whole plant of Verbena bonariensis. The structures of all compounds were determined by spectroscopic analysis.
从马鞭草全株中分离得到4个已知的黄酮类葡糖苷类化合物，木犀草素-7- o -β- d -葡糖苷(8)、芹菜素-7- o -β- d -葡糖苷(9)、黄芩素-7- o -β- d -葡糖苷(10)和hispidulin-7-O-β- d -葡糖苷(11)和7个已知的酚类化合物(1-7)。所有化合物的结构均通过光谱分析确定。
{"title":"Chemical Constituents of Verbena bonariensis","authors":"Chien‐Chih Chen, Huimin Huang, Chien-Chang Shen, Yu-lin Huang, J. Ou","doi":"10.7019/CPJ.200302.0065","DOIUrl":"https://doi.org/10.7019/CPJ.200302.0065","url":null,"abstract":"Four known flavone glucuronides, luteolin-7-O-β-D-glucuronide (8), apigenin-7-O-β-D-glucuronide (9), chrysoeriol-7-O-β-D-glucuronide (10) and hispidulin-7-O-β-D-glucuronide (11), and seven known phenolic compounds (1-7) were isolated from the whole plant of Verbena bonariensis. The structures of all compounds were determined by spectroscopic analysis.","PeriodicalId":22409,"journal":{"name":"The Chinese Pharmaceutical Journal","volume":"19 1","pages":"65-70"},"PeriodicalIF":0.0,"publicationDate":"2003-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"90658387","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Two meroterpenes bakuchiol and 12-hydroxyisobakuchiol, and three C-glucosylflavonoids, saponaretin, isoorientin and isoaffinetin together with other constituents plumbagin, isoshinano-lone, xanthyletin, xanthoxyletin, psoralen, plumbagic acid, plumbagic acid butyl ester, β-sitosterol and β-sitosteryl glucoside have been isolated from the aerial part of Plumbago zeylanica. This is the first report of isolation of meroterpenes and C-glucosylflavonoids from Plumbago species.
{"title":"Meroterpenes and C-Glucosylflavonoids from the Aerial Parts of Plumbago zeylanica","authors":"Lie-Chwen Lin, C. Chou","doi":"10.7019/CPJ.200302.0077","DOIUrl":"https://doi.org/10.7019/CPJ.200302.0077","url":null,"abstract":"Two meroterpenes bakuchiol and 12-hydroxyisobakuchiol, and three C-glucosylflavonoids, saponaretin, isoorientin and isoaffinetin together with other constituents plumbagin, isoshinano-lone, xanthyletin, xanthoxyletin, psoralen, plumbagic acid, plumbagic acid butyl ester, β-sitosterol and β-sitosteryl glucoside have been isolated from the aerial part of Plumbago zeylanica. This is the first report of isolation of meroterpenes and C-glucosylflavonoids from Plumbago species.","PeriodicalId":22409,"journal":{"name":"The Chinese Pharmaceutical Journal","volume":"1 1","pages":"77-81"},"PeriodicalIF":0.0,"publicationDate":"2003-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"88647906","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
We have described the partial synthesis of antitumor 4-anilinofuro [2, 3-b] quinoline derivatives from dictamnine, a natural alkaloid. Due to the limited supply of natural starting material, we report herein an efficient total synthesis of the title compounds from the known 3, 4-dichlorofuro [2, 3-b] quinoline in two steps.
{"title":"An efficient synthesis of antitumor 4-anilinofuro[2,3-b]quinoline derivatives","authors":"I‐Li Chen, Yeh‐long Chen, C. Tzeng","doi":"10.7019/CPJ.200302.0049","DOIUrl":"https://doi.org/10.7019/CPJ.200302.0049","url":null,"abstract":"We have described the partial synthesis of antitumor 4-anilinofuro [2, 3-b] quinoline derivatives from dictamnine, a natural alkaloid. Due to the limited supply of natural starting material, we report herein an efficient total synthesis of the title compounds from the known 3, 4-dichlorofuro [2, 3-b] quinoline in two steps.","PeriodicalId":22409,"journal":{"name":"The Chinese Pharmaceutical Journal","volume":"47 2 1","pages":"49-53"},"PeriodicalIF":0.0,"publicationDate":"2003-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"89086947","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Continuing investigation of the chemical constituents of Dehaasia triandra Merr. Provided from the leaves eleven bisbenzylisoquinoline alkaloids, homoaromoline (1), daphnandrine (2), aromoline (3), daphnoline (4), pangkorimine (5), colorflammine (6), thalrugosine (7), obamegine (8), 2-norobamegine (9), dehatridine (10), and 1,2-dehydroapateline (11). The complete assignment of the 1H- and 13C-nmr data of these alkaloids was accomplished by 1D and 2D analyses. Conformational analysis of these alkaloids was performed by computer-assisted dynamic calculations supplemented with NOED and NOSEY analyses. Stable conformations were characterized for both the type VI and type VIII of bisbenzylisoquinoline diphenyl ether ring linkages that explained some special features in their 1H-NMR spectra as well as their CD absorptions.
{"title":"Chemical Constituents from Dehaasia triandra. III. Bisbenzylisoquinoline Alkaloids from the Leaves and Their Conformational Analysis","authors":"Chien-Kuang Chen, Shoei‐Sheng Lee, Chung-Hsiung Chen","doi":"10.7019/CPJ.200302.0035","DOIUrl":"https://doi.org/10.7019/CPJ.200302.0035","url":null,"abstract":"Continuing investigation of the chemical constituents of Dehaasia triandra Merr. Provided from the leaves eleven bisbenzylisoquinoline alkaloids, homoaromoline (1), daphnandrine (2), aromoline (3), daphnoline (4), pangkorimine (5), colorflammine (6), thalrugosine (7), obamegine (8), 2-norobamegine (9), dehatridine (10), and 1,2-dehydroapateline (11). The complete assignment of the 1H- and 13C-nmr data of these alkaloids was accomplished by 1D and 2D analyses. Conformational analysis of these alkaloids was performed by computer-assisted dynamic calculations supplemented with NOED and NOSEY analyses. Stable conformations were characterized for both the type VI and type VIII of bisbenzylisoquinoline diphenyl ether ring linkages that explained some special features in their 1H-NMR spectra as well as their CD absorptions.","PeriodicalId":22409,"journal":{"name":"The Chinese Pharmaceutical Journal","volume":"67 1","pages":"35-47"},"PeriodicalIF":0.0,"publicationDate":"2003-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"78209904","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
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