Y. Ichikawa, Kenta Saito, Rika Mimura, Ayumi Kitamori, Akihito Matsukawa, Akifumi Ikeda, T. Masuda, H. Kotsuki*, Keiji Nakano
{"title":"A BIOMIMETIC APPROACH TO THE SYNTHESIS OF TERPENE-AMINO ACID CONJUGATES : THE UGI REACTION IN THE HYPOTHETICAL BIOSYNTHESIS OF MARINE NATURAL PRODUCTS","authors":"Y. Ichikawa, Kenta Saito, Rika Mimura, Ayumi Kitamori, Akihito Matsukawa, Akifumi Ikeda, T. Masuda, H. Kotsuki*, Keiji Nakano","doi":"10.3987/COM-16-13442","DOIUrl":"https://doi.org/10.3987/COM-16-13442","url":null,"abstract":"","PeriodicalId":12850,"journal":{"name":"Heterocycles : an international journal for reviews and communications in heterocyclic chemistry","volume":"33 1","pages":"1040-1053"},"PeriodicalIF":0.0,"publicationDate":"2016-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"73503800","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 NOVEL BENZIMIDAZOLES 2-FUNCTIONALIZED WITH PYRROLIDINONE AND γ-AMINO ACID WITH A HIGH ANTIBACTERIAL ACTIVITY","authors":"V. Strelciunaite, K. Anusevičius, I. Tumosienė","doi":"10.3987/com-15-13343","DOIUrl":"https://doi.org/10.3987/com-15-13343","url":null,"abstract":"","PeriodicalId":12850,"journal":{"name":"Heterocycles : an international journal for reviews and communications in heterocyclic chemistry","volume":"3 1","pages":"235-251"},"PeriodicalIF":0.0,"publicationDate":"2016-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"78982740","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. Umezawa, Liyan Wang, Yinzhi Lin, Kulrawee Sidthipong, Jianqiang Tang, Mengjie Li, T. Koyano, T. Kowithayakorn, K. Sumiyoshi
{"title":"INHIBITION OF NF-κB AND CELLULAR INVASION BY NOVEL FLAVONOID DISMAL IN OVARIAN CARCINOMA CELLS","authors":"K. Umezawa, Liyan Wang, Yinzhi Lin, Kulrawee Sidthipong, Jianqiang Tang, Mengjie Li, T. Koyano, T. Kowithayakorn, K. Sumiyoshi","doi":"10.3987/com-15-13386","DOIUrl":"https://doi.org/10.3987/com-15-13386","url":null,"abstract":"","PeriodicalId":12850,"journal":{"name":"Heterocycles : an international journal for reviews and communications in heterocyclic chemistry","volume":"21 1 1","pages":"353-360"},"PeriodicalIF":0.0,"publicationDate":"2016-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"78666321","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":"DESIGN, SYNTHESIS AND EVALUATION OF AN L-DOPA-DERIVED MACROCYCLIC HEXAOXAZOLE (6OTD) AS A G-QUADRUPLEX-SELECTIVE LIGAND","authors":"Takahiro Nakamura, Yue Ma, Keisuke Iida","doi":"10.3987/com-15-13383","DOIUrl":"https://doi.org/10.3987/com-15-13383","url":null,"abstract":"","PeriodicalId":12850,"journal":{"name":"Heterocycles : an international journal for reviews and communications in heterocyclic chemistry","volume":"11 1","pages":"305-315"},"PeriodicalIF":0.0,"publicationDate":"2016-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"90725243","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}
Three types of nicotinoyl amino acids, i.e., nicotinoyl leucine (NA-Leu), NA-Leu-His, and NA-Tyr-Tyr, were synthesized by Fmoc solid-phase peptide synthesis, purified by reversed-phase HPLC, and characterized by 1H, 13C NMR and ESI-MS. The interactions of nicotinic acid and nicotinoyl derivatives with ctDNA were investigated by fluorescence spectroscopy. NA-Leu-His and NA-Tyr-Tyr exhibited higher affinity for ctDNA compared with free NA, indicating that the imidazolyl of histidine and the phenol group of tyrosine can enhance the embedding interaction of nicotinoyl derivatives into ctDNA. In addition, leucine in the derivatives helped form a special surrounding and spatial structure to interact with ctDNA. The stronger interaction of NA-Tyr-Tyr and NA-Leu-His with ctDNA suggested that the modified nicotinic acid probably erhaps had significant practical value and should be further studied. INTRODUCTION Nicotinic acid (NA) is one of thirteen necessary vitamins, and also is known as vitamin PP (pellegra preventive factor) because it has been identified as the cause of pellegra disease. Niacinamide cannot be directly converted from NA in the body, but both compounds are important components of the co-factors NAD and NADP.1 At present, NA and niacinamide are mainly used as peripheral vasodilators in the 252 HETEROCYCLES, Vol. 92, No. 2, 2016
{"title":"PREPARATION OF NICOTINOYL AMINO ACID DERIVATIVES BY FMOC-SOLID PHASE SYNTHESIS AND PRELIMINARY STUDIES ON THE DNA-BINDING PROPERTIES OF NICOTINOYL DERIVATIVES","authors":"Dongxin Zhao, K. Lu","doi":"10.3987/com-15-13345","DOIUrl":"https://doi.org/10.3987/com-15-13345","url":null,"abstract":"Three types of nicotinoyl amino acids, i.e., nicotinoyl leucine (NA-Leu), NA-Leu-His, and NA-Tyr-Tyr, were synthesized by Fmoc solid-phase peptide synthesis, purified by reversed-phase HPLC, and characterized by 1H, 13C NMR and ESI-MS. The interactions of nicotinic acid and nicotinoyl derivatives with ctDNA were investigated by fluorescence spectroscopy. NA-Leu-His and NA-Tyr-Tyr exhibited higher affinity for ctDNA compared with free NA, indicating that the imidazolyl of histidine and the phenol group of tyrosine can enhance the embedding interaction of nicotinoyl derivatives into ctDNA. In addition, leucine in the derivatives helped form a special surrounding and spatial structure to interact with ctDNA. The stronger interaction of NA-Tyr-Tyr and NA-Leu-His with ctDNA suggested that the modified nicotinic acid probably erhaps had significant practical value and should be further studied. INTRODUCTION Nicotinic acid (NA) is one of thirteen necessary vitamins, and also is known as vitamin PP (pellegra preventive factor) because it has been identified as the cause of pellegra disease. Niacinamide cannot be directly converted from NA in the body, but both compounds are important components of the co-factors NAD and NADP.1 At present, NA and niacinamide are mainly used as peripheral vasodilators in the 252 HETEROCYCLES, Vol. 92, No. 2, 2016","PeriodicalId":12850,"journal":{"name":"Heterocycles : an international journal for reviews and communications in heterocyclic chemistry","volume":"24 1","pages":"252-259"},"PeriodicalIF":0.0,"publicationDate":"2016-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"83373172","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":"EXPERIMENTAL INVESTIGATION OF TETRACYCLIC COMPOUNDS CONTAINING A NINE-MEMBERED SULTAM VIA COBALT ALKYNE COMPLEXES","authors":"Kyosuke Kaneda, Misuzu Fujita, Risa Naruse","doi":"10.3987/com-15-13381","DOIUrl":"https://doi.org/10.3987/com-15-13381","url":null,"abstract":"","PeriodicalId":12850,"journal":{"name":"Heterocycles : an international journal for reviews and communications in heterocyclic chemistry","volume":"53 1","pages":"291-304"},"PeriodicalIF":0.0,"publicationDate":"2016-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"85319469","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":"AN EFFICIENT CONVERSION OF LYSINE TO 2-AMINOCAPROLACTAM","authors":"H. Matsumoto, Kouji Kaiso, A. Kamimura","doi":"10.3987/com-15-13358","DOIUrl":"https://doi.org/10.3987/com-15-13358","url":null,"abstract":"","PeriodicalId":12850,"journal":{"name":"Heterocycles : an international journal for reviews and communications in heterocyclic chemistry","volume":"30 1","pages":"337-345"},"PeriodicalIF":0.0,"publicationDate":"2016-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"78400616","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}
Antioxidant activities of the simple phenolic carbazoles 5-11 were evaluated by 2,2-diphenyl-1-picrylhydrazyl and 2,2’-azinobis-(3-ethylbenzthiazoline-6-sulfonate) radical scavenging assays. The simple phenolic carbazoles 5-7, 9, and 11 exhibited stronger antioxidant activities than α-tocopherol, and similar antioxidant activities as phenolic carbazole alkaloids carazostatin (1), and carbazomadurins A (3) and B (4). Bond dissociation energies and highest occupied molecule orbital energy levels of a series of phenolic carbazoles including phenolic carbazole alkaloids were calculated. The reducing ability of the phenolic carbazole core could be important role for the antioxidant activity of carbazole alkaloids 1, 3, and 4. Reactive oxygen species (ROS) are highly reactive small substances with an important role in the initiation of various diseases such as carcinogenesis, drug-associated toxicity, inflammation, and atherogenesis as well as aging in aerobic organisms. Natural antioxidants, including ascorbic acid, α-tocopherol (VE), ubiquinol, uric acid, polyphenols and their analogs have been intensive investigation 120 HETEROCYCLES, Vol. 92, No. 1, 2016
{"title":"ANTIOXIDANT EFFECTS OF THE HYDROXY GROUPS IN THE SIMPLE PHENOLIC CARBAZOLES","authors":"Yuhzo Hieda, N. Hatae, M. Anraku","doi":"10.3987/com-15-13363","DOIUrl":"https://doi.org/10.3987/com-15-13363","url":null,"abstract":"Antioxidant activities of the simple phenolic carbazoles 5-11 were evaluated by 2,2-diphenyl-1-picrylhydrazyl and 2,2’-azinobis-(3-ethylbenzthiazoline-6-sulfonate) radical scavenging assays. The simple phenolic carbazoles 5-7, 9, and 11 exhibited stronger antioxidant activities than α-tocopherol, and similar antioxidant activities as phenolic carbazole alkaloids carazostatin (1), and carbazomadurins A (3) and B (4). Bond dissociation energies and highest occupied molecule orbital energy levels of a series of phenolic carbazoles including phenolic carbazole alkaloids were calculated. The reducing ability of the phenolic carbazole core could be important role for the antioxidant activity of carbazole alkaloids 1, 3, and 4. Reactive oxygen species (ROS) are highly reactive small substances with an important role in the initiation of various diseases such as carcinogenesis, drug-associated toxicity, inflammation, and atherogenesis as well as aging in aerobic organisms. Natural antioxidants, including ascorbic acid, α-tocopherol (VE), ubiquinol, uric acid, polyphenols and their analogs have been intensive investigation 120 HETEROCYCLES, Vol. 92, No. 1, 2016","PeriodicalId":12850,"journal":{"name":"Heterocycles : an international journal for reviews and communications in heterocyclic chemistry","volume":"13 1","pages":"120-132"},"PeriodicalIF":0.0,"publicationDate":"2016-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"85521723","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":"RADICAL SCAVENGING ACTIVITY OF ASCORBIC ACID ANALOGS CONTAINING A CARBONYL CONJUGATED ENE-DIOL STRUCTURE","authors":"M. Mochizuki, S. Nomura, K. Inami","doi":"10.3987/com-15-13366","DOIUrl":"https://doi.org/10.3987/com-15-13366","url":null,"abstract":"","PeriodicalId":12850,"journal":{"name":"Heterocycles : an international journal for reviews and communications in heterocyclic chemistry","volume":"57 1","pages":"86-101"},"PeriodicalIF":0.0,"publicationDate":"2016-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"89213968","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":"SOLVENT EXTRACTION ABILITY OF NEW DIETHYL PHOSPHATE-MODIFIED THIACALIX[6]ARENE TOWARDS PGM SOLUTION","authors":"K. U. M. Rao, T. Kimuro, M. Yamada","doi":"10.3987/com-15-13346","DOIUrl":"https://doi.org/10.3987/com-15-13346","url":null,"abstract":"","PeriodicalId":12850,"journal":{"name":"Heterocycles : an international journal for reviews and communications in heterocyclic chemistry","volume":"31 1","pages":"55-63"},"PeriodicalIF":0.0,"publicationDate":"2016-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"76144323","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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