Munenori Sakurai, Takuma Yoshida, Lei Wang, Yuta Murai, K. Masuda, Y. Sakihama, Y. Hashidoko, Y. Hatanaka, M. Hashimoto
Salicin (salicyl alcohol glucoside) is a substance well known for its bitter taste. A photoreactive diazirinyl derivative of salicin will be utilized for the functional analysis of interactions between the bitter taste receptor and salicin. Glucosides of salicyl derivatives are more difficult than phenol derivatives that are unsubstituted at the ortho-position. A diazirinyl salicin derivative was synthesized at moderate yields by glucosidation of 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide and 2-hydroxy-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]-benzaldehyde in the presence of a phase-transfer catalyst, nBuEt3NBr, followed by reduction and deprotection. Salicin is long known as one of the major components of phenyl glycosides in the family Salicaceae and is a bitter anti-inflammatory compound. Elucidation of the functions of its gustatory receptor on the basis of structure–activity relationships may reveal the mechanism of homeostatic functions, which is of great interest to scientists. Photoaffinity labeling is one of the most common techniques used in the analysis of chemical biology. To the best of our knowledge, there are no reports on the preparation of photoreactive salicin derivatives for the analysis of bitter taste receptors. Two modifications of phenyl glucoside derivatives using diazirine have been reported. The derivatives are not substituted at the o-position of phenol. One modification is glucosidation of p-diazirinyl phenol to synthesize α-glucoside and the other This paper is dedicated to Prof. Dr. Isao Kuwajima on the occasion of his 77th birthday. is construction of the diazirine moiety in the precursor of the phenyl glucoside derivative. However, glucosides of salicyl alcohol derivatives are more complicated than glucosides of the o-position unsubstituted phenol derivatives. Optimization of glucosidation of salicyl alcohol or salicyl aldehyde derivatives is essential to the synthesis of target diazirinyl derivatives of salicin. In this study, we report the synthesis of diazirinyl derivative and preliminary screening of glucosidations for salicyl alcohol and salicyl aldehyde derivatives. O OH HO HO OH O F3C N N OH O OAc AcO AcO AcO OAc F3C N N
水杨苷(水杨醇葡萄糖苷)是一种众所周知的苦味物质。利用水杨苷的光反应性二嗪基衍生物对苦味受体与水杨苷的相互作用进行功能分析。水杨基衍生物的糖苷比邻位未被取代的苯酚衍生物更难得到。在相转移催化剂nBuEt3NBr的存在下，以2,3,4,6-四- o -乙酰基-α- d -葡萄糖吡喃基溴和2-羟基-4-[3-(三氟甲基)- 3h -二氮基-3-基]-苯甲醛为原料，经还原和脱保护，以中产率合成了二氮基水杨苷衍生物。水杨苷是水杨科苯基苷的主要成分之一，是一种苦味抗炎化合物。在构效关系的基础上阐明其味觉受体的功能，可以揭示其体内平衡功能的机制，这是科学家们非常感兴趣的问题。光亲和标记是化学生物学分析中最常用的技术之一。据我们所知，还没有关于制备光反应水杨苷衍生物用于苦味感受器分析的报道。已有两种苯基葡萄糖苷衍生物用重氮嘧啶修饰的报道。这些衍生物在苯酚的o位上没有被取代。一种是对二氮基苯酚的糖苷化合成α-葡萄糖苷，另一种是在Kuwajima教授77岁生日之际，将这篇论文献给他。是苯基葡萄糖苷衍生物前体中重氮嘧啶部分的结构。然而，水杨醇衍生物的糖苷比o位未取代苯酚衍生物的糖苷更复杂。优化水杨醇或水杨醛衍生物的糖苷化反应对水杨酸二嗪基衍生物的合成至关重要。在本研究中，我们报道了二氮基衍生物的合成以及水杨醇和水杨醛衍生物葡萄糖糖苷的初步筛选。哦，哦，哦，哦，哦，哦，哦，哦，哦，哦，哦，哦，哦，哦，哦，哦，哦，哦，哦，哦，哦，哦，哦，哦，哦，哦
{"title":"SYNTHESIS OF PHOTOREACTIVE DIAZIRINYL SALICIN DERIVATIVE TO ELUCIDATE FUNCTIONAL ANALYSIS OF THE BITTER TASTE RECEPTOR (Dedicated to Professor Isao Kuwajima on the occasion of his 77th birthday)","authors":"Munenori Sakurai, Takuma Yoshida, Lei Wang, Yuta Murai, K. Masuda, Y. Sakihama, Y. Hashidoko, Y. Hatanaka, M. Hashimoto","doi":"10.3987/COM-14-S(K)36","DOIUrl":"https://doi.org/10.3987/COM-14-S(K)36","url":null,"abstract":"Salicin (salicyl alcohol glucoside) is a substance well known for its bitter taste. A photoreactive diazirinyl derivative of salicin will be utilized for the functional analysis of interactions between the bitter taste receptor and salicin. Glucosides of salicyl derivatives are more difficult than phenol derivatives that are unsubstituted at the ortho-position. A diazirinyl salicin derivative was synthesized at moderate yields by glucosidation of 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide and 2-hydroxy-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]-benzaldehyde in the presence of a phase-transfer catalyst, nBuEt3NBr, followed by reduction and deprotection. Salicin is long known as one of the major components of phenyl glycosides in the family Salicaceae and is a bitter anti-inflammatory compound. Elucidation of the functions of its gustatory receptor on the basis of structure–activity relationships may reveal the mechanism of homeostatic functions, which is of great interest to scientists. Photoaffinity labeling is one of the most common techniques used in the analysis of chemical biology. To the best of our knowledge, there are no reports on the preparation of photoreactive salicin derivatives for the analysis of bitter taste receptors. Two modifications of phenyl glucoside derivatives using diazirine have been reported. The derivatives are not substituted at the o-position of phenol. One modification is glucosidation of p-diazirinyl phenol to synthesize α-glucoside and the other This paper is dedicated to Prof. Dr. Isao Kuwajima on the occasion of his 77th birthday. is construction of the diazirine moiety in the precursor of the phenyl glucoside derivative. However, glucosides of salicyl alcohol derivatives are more complicated than glucosides of the o-position unsubstituted phenol derivatives. Optimization of glucosidation of salicyl alcohol or salicyl aldehyde derivatives is essential to the synthesis of target diazirinyl derivatives of salicin. In this study, we report the synthesis of diazirinyl derivative and preliminary screening of glucosidations for salicyl alcohol and salicyl aldehyde derivatives. O OH HO HO OH O F3C N N OH O OAc AcO AcO AcO OAc F3C N N","PeriodicalId":12850,"journal":{"name":"Heterocycles : an international journal for reviews and communications in heterocyclic chemistry","volume":"66 1","pages":"698-705"},"PeriodicalIF":0.0,"publicationDate":"2015-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"83378767","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":"INVESTIGATION OF Pd(II)-CATALYZED CYCLIZATION OF CHIRAL θ-HYDROXY-α,β,γ,δ-UNSATURATED DIENOL (Dedicated to Professor Isao Kuwajima on the occasion of his 77th birthday)","authors":"A. Ida, N. Hoshiya, J. Uenishi","doi":"10.3987/COM-14-S(K)77","DOIUrl":"https://doi.org/10.3987/COM-14-S(K)77","url":null,"abstract":"","PeriodicalId":12850,"journal":{"name":"Heterocycles : an international journal for reviews and communications in heterocyclic chemistry","volume":"42 1","pages":"1082-1093"},"PeriodicalIF":0.0,"publicationDate":"2015-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"78841370","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 OF AZA-POLYQUINANES VIA FISCHER INDOLE CYCLIZATION UNDER GREEN CONDITIONS (Dedicated to Professor Isao Kuwajima on the occasion of his 77th birthday)","authors":"S. Kotha, A. Chinnam","doi":"10.3987/COM-14-S(K)35","DOIUrl":"https://doi.org/10.3987/COM-14-S(K)35","url":null,"abstract":"","PeriodicalId":12850,"journal":{"name":"Heterocycles : an international journal for reviews and communications in heterocyclic chemistry","volume":"76 1","pages":"690-697"},"PeriodicalIF":0.0,"publicationDate":"2015-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"86714534","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":"Pd-CATALYZED INTRAMOLECULAR OXIDATIVE COUPLING REACTION OF 1,1'-CARBONYLDIINDOLES (Dedicated to Professor Isao Kuwajima on the occasion of his 77th birthday)","authors":"Takumi Abe, M. Ishikura","doi":"10.3987/COM-14-S(K)28","DOIUrl":"https://doi.org/10.3987/COM-14-S(K)28","url":null,"abstract":"","PeriodicalId":12850,"journal":{"name":"Heterocycles : an international journal for reviews and communications in heterocyclic chemistry","volume":"75 1","pages":"673-680"},"PeriodicalIF":0.0,"publicationDate":"2015-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"86104232","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":"A NEW CLASS OF STRUCTURALLY SIMPLE AND HIGHLY EMISSIVE FLUOROPHORES WITH A PYRIDINE–ACETYLENE–PHENOL CONJUGATE (Dedicated to Professor Isao Kuwajima on the occasion of his 77th birthday)","authors":"Yuki Ohishi, H. Abe, M. Inouye","doi":"10.3987/COM-14-S(K)51","DOIUrl":"https://doi.org/10.3987/COM-14-S(K)51","url":null,"abstract":"","PeriodicalId":12850,"journal":{"name":"Heterocycles : an international journal for reviews and communications in heterocyclic chemistry","volume":"42 1","pages":"515-528"},"PeriodicalIF":0.0,"publicationDate":"2015-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"90750284","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":"SIMPLE SYNTHETIC METHOD FOR 1-HYDROXYINDOLE AND ITS APPLICATION TO 1-HYDROXYTRYPTOPHAN DERIVATIVES (Dedicated to Professor Isao Kuwajima on the occasion of his 77th birthday)","authors":"T. Kawasaki, M. Tabata, K. Nakagawa","doi":"10.3987/COM-14-S(K)74","DOIUrl":"https://doi.org/10.3987/COM-14-S(K)74","url":null,"abstract":"","PeriodicalId":12850,"journal":{"name":"Heterocycles : an international journal for reviews and communications in heterocyclic chemistry","volume":"1 1","pages":"1038-1071"},"PeriodicalIF":0.0,"publicationDate":"2015-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"82262990","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":"REDOX RESPONSIVE POLYMER INCORPORATED WITH MESOGENIC UNIT AND BIS(BENZODITHIOLYL)BITHIENYL SCAFFOLD (Dedicated to Professor Isao Kuwajima on the occasion of his 77th birthday)","authors":"T. Ohtake, Hideki Tanaka, Tetsuro Matsumoto","doi":"10.3987/COM-14-S(K)44","DOIUrl":"https://doi.org/10.3987/COM-14-S(K)44","url":null,"abstract":"","PeriodicalId":12850,"journal":{"name":"Heterocycles : an international journal for reviews and communications in heterocyclic chemistry","volume":"14 1","pages":"811-818"},"PeriodicalIF":0.0,"publicationDate":"2015-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"82403578","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":"FORMATION OF 2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSIDIC LINKAGES VIA GLYCOSIDATION USING A COMBINATION OF TWO LEWIS ACIDS (Dedicated to Professor Isao Kuwajima on the occasion of his 77th birthday)","authors":"Yoshiki Oda, M. Midorikawa, T. Yamanoi","doi":"10.3987/COM-14-S(K)4","DOIUrl":"https://doi.org/10.3987/COM-14-S(K)4","url":null,"abstract":"","PeriodicalId":12850,"journal":{"name":"Heterocycles : an international journal for reviews and communications in heterocyclic chemistry","volume":"25 1","pages":"198-215"},"PeriodicalIF":0.0,"publicationDate":"2015-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"82910857","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 oxidation of 3-oxo-N-phenylbutanamides 1 with manganese(III) acetate in ethanol afforded dimeric 3,3'-biindoline-2,2'-dione derivatives 3–5. A similar reaction of N,2-disubstituted N-aryl-3-oxobutanamides 6 in acetic acid produced 3-acetylindolin-2-ones 7 bearing various substituents in good to excellent yields. The acetylindolinones 7 were easily deacetylated by treatment using neutral alumina in diethyl ether. Both the acetylindolinones 7 and deacetylated indolinones 8 were transformed by reduction into the substituted 1H-indoles. INTRODUCTION Many of the chemistries for indoles and their derivatives have been investigated and reported. However, the synthesis and reaction of these heterocycles are still attractive from the view point of the synthetic method, total synthesis of natural products, biological and pharmacological activities, and material science. Recently, we reported the Mn(III)-mediated direct substitution of methoxynaphthalenes with N-aryl-3-oxobutanamides, giving the 3-oxobutanamide-substituted naphthalene I in addition to a small amount of demethoxylated naphthofuran II and benzoindolinone III (Scheme 1, eq. 1). Although the yield of the heterocyclic compounds II and III was poor, the carbon-carbon bond formation efficiently occurred during the reaction. We also reported the facile synthesis of 3,4-dihydro-2(1H)-quinolinones, 540 HETEROCYCLES, Vol. 90, No. 1, 2015
{"title":"Mn(III)-BASED OXIDATIVE CYCLIZATION OF N-ARYL-3-OXOBUTANAMIDES. FACILE SYNTHESIS AND TRANSFORMATION OF SUBSTITUTED OXINDOLES (Dedicated to Professor Isao Kuwajima on the occasion of his 77th birthday)","authors":"Nobutaka Kikue, Tetsuya Takahashi, H. Nishino","doi":"10.3987/COM-14-S(K)57","DOIUrl":"https://doi.org/10.3987/COM-14-S(K)57","url":null,"abstract":"The oxidation of 3-oxo-N-phenylbutanamides 1 with manganese(III) acetate in ethanol afforded dimeric 3,3'-biindoline-2,2'-dione derivatives 3–5. A similar reaction of N,2-disubstituted N-aryl-3-oxobutanamides 6 in acetic acid produced 3-acetylindolin-2-ones 7 bearing various substituents in good to excellent yields. The acetylindolinones 7 were easily deacetylated by treatment using neutral alumina in diethyl ether. Both the acetylindolinones 7 and deacetylated indolinones 8 were transformed by reduction into the substituted 1H-indoles. INTRODUCTION Many of the chemistries for indoles and their derivatives have been investigated and reported. However, the synthesis and reaction of these heterocycles are still attractive from the view point of the synthetic method, total synthesis of natural products, biological and pharmacological activities, and material science. Recently, we reported the Mn(III)-mediated direct substitution of methoxynaphthalenes with N-aryl-3-oxobutanamides, giving the 3-oxobutanamide-substituted naphthalene I in addition to a small amount of demethoxylated naphthofuran II and benzoindolinone III (Scheme 1, eq. 1). Although the yield of the heterocyclic compounds II and III was poor, the carbon-carbon bond formation efficiently occurred during the reaction. We also reported the facile synthesis of 3,4-dihydro-2(1H)-quinolinones, 540 HETEROCYCLES, Vol. 90, No. 1, 2015","PeriodicalId":12850,"journal":{"name":"Heterocycles : an international journal for reviews and communications in heterocyclic chemistry","volume":"41 1","pages":"540-562"},"PeriodicalIF":0.0,"publicationDate":"2015-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"76829134","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 RHODOTORULIC ACID AND ITS 1,4-DIMETHYLATED DERIVATIVE (Dedicated to Professor Isao Kuwajima on the occasion of his 77th birthday)","authors":"Michiyasu Nakao, Shintaro Fukayama, Syuji Kitaike","doi":"10.3987/COM-14-S(K)67","DOIUrl":"https://doi.org/10.3987/COM-14-S(K)67","url":null,"abstract":"","PeriodicalId":12850,"journal":{"name":"Heterocycles : an international journal for reviews and communications in heterocyclic chemistry","volume":"39 1","pages":"1309-1316"},"PeriodicalIF":0.0,"publicationDate":"2015-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"82703120","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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