A new quinolinecarbaldehyde, 7-(carboxymethoxy)-6-hydroxy-3-sulfoquinoline-5-carbaldehyde (1), was synthesized from eugenol, a natural phenol, by four successive reaction steps. The condensation of 1 with various amino compounds afforded 12 Schiff-bases (2 – 13) and 3 hydrazones (14 – 16). The structures of the aldehyde, its Schiff-bases and the hydrazone derivatives were determined by analyzing their IR, 1D NMR, 2D NMR and MS spectra. 1H NMR and NOESY data show that the imine -CH=Ngroup in the reported Schiff-bases and hydrazones exists in E-configuration. The quinoline scaffold is an important class of heterocyclic compounds that possesses diverse chemotherapeutic activities. Several quinoline compounds isolated from natural resources or prepared synthetically are significant with respect to medicinal chemistry and biomedical use.1-5 Many quinolinecarbaldehyde derivatives exhibit high antituberculosis,6 antibacterial,7,8 and anticancer9,10 activities. The quinolinecarbaldehyde derivatives, in particular Schiff-base, are also reported as corrosion inhibitors,11,12 as organic ligands for synthesis of various interesting complexes,13-15 and as intermediates for synthesis of new heterocycles.16 Many hydrazones containing quinoline ring exhibit significant antitubercular properties17,18 and high antimalarial activity.19,20 Recently, we have reported on an efficient and simple method for the synthesis of 7-(carboxymethoxy)6-hydroxy-3-sulfoquinoline starting with eugenol,21 the main constituent of Ocimum sanctum L. oil (a cheap natural source for commercial extraction of eugenol22). This quinoline derivative could act as a key compound in order to prepare useful poly-functionalized quinolines. In this study, we present the synthesis and the structure of a new polysubstituted quinolinecarbaldehyde, 7-(carboxymethoxy)6-hydroxy3-sulfoquinoline-5-carbaldehyde, its Schiff-bases and hydrazones. HETEROCYCLES, Vol. 91, No. 9, 2015 1797
{"title":"SYNTHESIS AND CHARACTERIZATION OF POLYSUBSTITUTED 5-QUINOLINECARBALDEHYDE DERIVATIVES","authors":"N. Dinh, Duong Quoc Hoan, N. Hien","doi":"10.3987/com-15-13270","DOIUrl":"https://doi.org/10.3987/com-15-13270","url":null,"abstract":"A new quinolinecarbaldehyde, 7-(carboxymethoxy)-6-hydroxy-3-sulfoquinoline-5-carbaldehyde (1), was synthesized from eugenol, a natural phenol, by four successive reaction steps. The condensation of 1 with various amino compounds afforded 12 Schiff-bases (2 – 13) and 3 hydrazones (14 – 16). The structures of the aldehyde, its Schiff-bases and the hydrazone derivatives were determined by analyzing their IR, 1D NMR, 2D NMR and MS spectra. 1H NMR and NOESY data show that the imine -CH=Ngroup in the reported Schiff-bases and hydrazones exists in E-configuration. The quinoline scaffold is an important class of heterocyclic compounds that possesses diverse chemotherapeutic activities. Several quinoline compounds isolated from natural resources or prepared synthetically are significant with respect to medicinal chemistry and biomedical use.1-5 Many quinolinecarbaldehyde derivatives exhibit high antituberculosis,6 antibacterial,7,8 and anticancer9,10 activities. The quinolinecarbaldehyde derivatives, in particular Schiff-base, are also reported as corrosion inhibitors,11,12 as organic ligands for synthesis of various interesting complexes,13-15 and as intermediates for synthesis of new heterocycles.16 Many hydrazones containing quinoline ring exhibit significant antitubercular properties17,18 and high antimalarial activity.19,20 Recently, we have reported on an efficient and simple method for the synthesis of 7-(carboxymethoxy)6-hydroxy-3-sulfoquinoline starting with eugenol,21 the main constituent of Ocimum sanctum L. oil (a cheap natural source for commercial extraction of eugenol22). This quinoline derivative could act as a key compound in order to prepare useful poly-functionalized quinolines. In this study, we present the synthesis and the structure of a new polysubstituted quinolinecarbaldehyde, 7-(carboxymethoxy)6-hydroxy3-sulfoquinoline-5-carbaldehyde, its Schiff-bases and hydrazones. HETEROCYCLES, Vol. 91, No. 9, 2015 1797","PeriodicalId":12850,"journal":{"name":"Heterocycles : an international journal for reviews and communications in heterocyclic chemistry","volume":"34 2 1","pages":"1797-1808"},"PeriodicalIF":0.0,"publicationDate":"2015-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"75750117","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}
{"title":"SYNTHESIS AND IN VITRO CYTOTOXICITY EVALUATION OF NEW 2-THIOXO-BENZO[g]QUINAZOLIN-4(3H)-ONE DERIVATIVES","authors":"R. Al-Salahi, R. E. Dib, M. Marzouk","doi":"10.3987/com-15-13282","DOIUrl":"https://doi.org/10.3987/com-15-13282","url":null,"abstract":"","PeriodicalId":12850,"journal":{"name":"Heterocycles : an international journal for reviews and communications in heterocyclic chemistry","volume":"40 1","pages":"1735-1751"},"PeriodicalIF":0.0,"publicationDate":"2015-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"75621795","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}
{"title":"SYNTHESIS OF THE AGLYCON OF PENTALINONSIDE","authors":"Nobuhisa Isaka, Saki Kawada, M. Ishiguro","doi":"10.3987/com-15-13288","DOIUrl":"https://doi.org/10.3987/com-15-13288","url":null,"abstract":"","PeriodicalId":12850,"journal":{"name":"Heterocycles : an international journal for reviews and communications in heterocyclic chemistry","volume":"2 1","pages":"1715-1721"},"PeriodicalIF":0.0,"publicationDate":"2015-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"81967115","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}
{"title":"Phenylpropanoids from the Leaves of Nicotiana tabacum and Their Anti-Tobacco Mosaic Virus Activities","authors":"Qinpeng Shen, Lan Li, Xin-Meg Xu","doi":"10.3987/com-15-13266","DOIUrl":"https://doi.org/10.3987/com-15-13266","url":null,"abstract":"","PeriodicalId":12850,"journal":{"name":"Heterocycles : an international journal for reviews and communications in heterocyclic chemistry","volume":"44 1","pages":"1775-1780"},"PeriodicalIF":0.0,"publicationDate":"2015-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"85362603","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}
{"title":"PREPARATION AND ANTIBACTERIAL EVALUATION OF SOME SYMMETRICAL TWIN-DRUG TYPE BIVALENT MOLECULES","authors":"Fumiko Fujisaki, Makoto Furutachi, Ryou Fujiwara","doi":"10.3987/com-15-13263","DOIUrl":"https://doi.org/10.3987/com-15-13263","url":null,"abstract":"","PeriodicalId":12850,"journal":{"name":"Heterocycles : an international journal for reviews and communications in heterocyclic chemistry","volume":"30 1","pages":"1668-1677"},"PeriodicalIF":0.0,"publicationDate":"2015-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84379425","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}
{"title":"Development of an Efficient Process for 3,6-Dihydro-2H-pyran-4-boronic Acid Pinacol Ester","authors":"F. Xue, Yong Zhu, Chang-Gong Li","doi":"10.3987/com-15-13255","DOIUrl":"https://doi.org/10.3987/com-15-13255","url":null,"abstract":"","PeriodicalId":12850,"journal":{"name":"Heterocycles : an international journal for reviews and communications in heterocyclic chemistry","volume":"18 1","pages":"1654-1659"},"PeriodicalIF":0.0,"publicationDate":"2015-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84100491","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}
K. Nishi, N. Seto, W. Iwasaki, Y. Matsuoka, Yuki Kashiwa, Y. Sano, Tadashi Kawaharada, Takashi Yazumi, Keiji Mizuki
{"title":"NIR-FLUORESCENT ETHYL 4,7-BIS(5-ARYLTHIOPHEN-2-YL)-1,2,5-OXADIAZOLO[3,4-c]PYRIDINE-6-CARBOXYLATE","authors":"K. Nishi, N. Seto, W. Iwasaki, Y. Matsuoka, Yuki Kashiwa, Y. Sano, Tadashi Kawaharada, Takashi Yazumi, Keiji Mizuki","doi":"10.3987/com-15-13197","DOIUrl":"https://doi.org/10.3987/com-15-13197","url":null,"abstract":"","PeriodicalId":12850,"journal":{"name":"Heterocycles : an international journal for reviews and communications in heterocyclic chemistry","volume":"9 1","pages":"1585-1590"},"PeriodicalIF":0.0,"publicationDate":"2015-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"80671849","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}
The first crystal structures of four 2-furylbenzimidazole acetohydrazide derivatives are reported herein. The compounds have been shown to be planar with a small cant that varies from 4 to 30°. The X-ray crystal structure of the compounds 7-10 revealed that compounds are oriented in the cis configuration which suggests that the acid hydrazide group is essential for the enhanced potency of 2-furylbenzimidazoles as anti-angiogenic agents.
{"title":"CRYSTAL STRUCTURES OF 2-FURYLBENZIMIDAZOLES WITH ANTIANGIOGENIC INHIBITION OF VEGF IN CELL LINE MCF-7","authors":"Keith J. Flanagan, Y. Shaker, Ahmed Temirak","doi":"10.3987/COM-15-13258","DOIUrl":"https://doi.org/10.3987/COM-15-13258","url":null,"abstract":"The first crystal structures of four 2-furylbenzimidazole acetohydrazide derivatives are reported herein. The compounds have been shown to be planar with a small cant that varies from 4 to 30°. The X-ray crystal structure of the compounds 7-10 revealed that compounds are oriented in the cis configuration which suggests that the acid hydrazide group is essential for the enhanced potency of 2-furylbenzimidazoles as anti-angiogenic agents.","PeriodicalId":12850,"journal":{"name":"Heterocycles : an international journal for reviews and communications in heterocyclic chemistry","volume":"6 1","pages":"1603-1613"},"PeriodicalIF":0.0,"publicationDate":"2015-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"87540873","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}
M. Villa-García, María Amparo Borja-de-la-Rosa, Holber Zuleta-Prada
The natural product chapingolide {systematic name: (4aS, 7R, 7aR)-7hydroxy-7-(hydroxymethyl)-4,4a,7,7a-tetrahydrocyclopenta[c]pyran-3(1H)-one}, C9H12O4, (1), is a new 11-nor-iridoid isolated from Calatola mollis Standl. The colourless compound has a bicyclic structure with an endo double bond in the five-membered ring. The absolute configuration was established by mean of the anomalous dispersion of the oxygen scatters present in the structure. Calatola is a genus of trees in family Icacinaceae. To date, about seven Calatola species are recorded in America, and most of them are found in rain forest regions.1 Approximately, four species of Calatola plants were recorded in Mexico1 of which, Calatola mollis Standl is a tree up to 20 m tall. The seeds exhibited potently vomitive-purgative activity.2 At present Calatola mollis species had been poorly investigated with only botanical descriptions reported to date.1 Even thought, specimens of this species have been misidentified as Calatola costaricensis,1,3 and hence a phytochemical study of plants of Calatola genus will be useful to establish differences in secondary metabolites composition as a valuable systematic character. The chapingolide (1), a nor-iridoid, was obtained from the methanolic extract of the leaves of Calatola mollis Standl, as a crystalline colourless compound. Its bicyclic structure is closely related to the structures discussed in Valladares and Rios,4 and Franzyk and Stermitz.5 The main differences reside in the oxidation HETEROCYCLES, Vol. 91, No. 7, 2015 1417
{"title":"STRUCTURE AND ABSOLUTE CONFIGURATION OF THE 11-NORIRIDOID \"CHAPINGOLIDE\"","authors":"M. Villa-García, María Amparo Borja-de-la-Rosa, Holber Zuleta-Prada","doi":"10.3987/com-15-13216","DOIUrl":"https://doi.org/10.3987/com-15-13216","url":null,"abstract":"The natural product chapingolide {systematic name: (4aS, 7R, 7aR)-7hydroxy-7-(hydroxymethyl)-4,4a,7,7a-tetrahydrocyclopenta[c]pyran-3(1H)-one}, C9H12O4, (1), is a new 11-nor-iridoid isolated from Calatola mollis Standl. The colourless compound has a bicyclic structure with an endo double bond in the five-membered ring. The absolute configuration was established by mean of the anomalous dispersion of the oxygen scatters present in the structure. Calatola is a genus of trees in family Icacinaceae. To date, about seven Calatola species are recorded in America, and most of them are found in rain forest regions.1 Approximately, four species of Calatola plants were recorded in Mexico1 of which, Calatola mollis Standl is a tree up to 20 m tall. The seeds exhibited potently vomitive-purgative activity.2 At present Calatola mollis species had been poorly investigated with only botanical descriptions reported to date.1 Even thought, specimens of this species have been misidentified as Calatola costaricensis,1,3 and hence a phytochemical study of plants of Calatola genus will be useful to establish differences in secondary metabolites composition as a valuable systematic character. The chapingolide (1), a nor-iridoid, was obtained from the methanolic extract of the leaves of Calatola mollis Standl, as a crystalline colourless compound. Its bicyclic structure is closely related to the structures discussed in Valladares and Rios,4 and Franzyk and Stermitz.5 The main differences reside in the oxidation HETEROCYCLES, Vol. 91, No. 7, 2015 1417","PeriodicalId":12850,"journal":{"name":"Heterocycles : an international journal for reviews and communications in heterocyclic chemistry","volume":"8 1","pages":"1417-1422"},"PeriodicalIF":0.0,"publicationDate":"2015-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"88096721","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}
{"title":"TRANSFORMATION OF BENZOXAZINONE DERIVATIVES TO SOME INTERESTING HETEROCYCLIC COMPOUNDS WITH EXPECTED BIOLOGICAL ACTIVITY","authors":"M. Marzouk, T. Farghaly, M. El-hashash","doi":"10.3987/com-15-13218","DOIUrl":"https://doi.org/10.3987/com-15-13218","url":null,"abstract":"","PeriodicalId":12850,"journal":{"name":"Heterocycles : an international journal for reviews and communications in heterocyclic chemistry","volume":"50 1","pages":"1399-1416"},"PeriodicalIF":0.0,"publicationDate":"2015-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"90836963","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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