Synthesis of New Glycosylamine Derivatives based on Carbohydrates

Q2 Pharmacology, Toxicology and Pharmaceutics
H. Jabbari
{"title":"Synthesis of New Glycosylamine Derivatives based on Carbohydrates","authors":"H. Jabbari","doi":"10.2174/1573407219666230810094657","DOIUrl":null,"url":null,"abstract":"\n\nGlycosylamine play an important role in living organisms. Most plants\nstore their chemical resources in the form of inactive glycosides, which are broken down and\nconverted into sugar in the body of herbivores by hydrolyzing enzymes. Glycosylamine are\nobtained from the secondary metabolism of plants and consist of two parts. One part of it contains\nsugar like glucose and is inactive in most substances, and has a good effect on the solubility of the\nglycosylamine derivatives and its absorption and even its transfer from one organ to another. The\ntherapeutic effect is related to the second part, which is called aglycan (or aglucan). Glycosylamine\nderivatives form a large group of valuable medicinal substances, which at the same time include\nsome of the most dangerous and toxic substances in nature. These substances are present in many\ngroups of flowering plants. Glycosides are made in different ways in different metabolic pathways.\nThese materials have a complex and special chemical structure and leave special effects on the\nhuman body. Glycosylamine derivatives are called O-glycosid, N-glycosid, S-glycosid in terms of\natoms coupling to anomeric carbon. Carbohydrate esterification reaction to prepare new glycosylamine derivatives is one of the most important carbohydrate reactions. The anomeric position of\ncarbohydrates with strong leaving groups is very important for the preparation of glycosides.\nPreparation of glycosylamine derivatives based on acetylated carbohydrates is the main purpose of this\narticle. Different carbohydrates were acetylated under mild conditions and high yields. The anomeric\nposition was deacetylated by a magnesium oxide heterogeneous catalyst in methanol solvent. In order\nto prepare new glycosides acetylated/ deacytylated carbohydrate reacted with N-Methyl-(naphtha-2-\nylmethoxy)amine. The final product was identified by various spectroscopic methods.\n\n\n\nAnhydrous sodium acetate (4 g) and α-D-glucose (28 mg, 5 g) were mixed. The mixture\nwas transferred to a 200 ml Round-bottom flask . Acetic acid (260 mg, 25 ml) was added to the\nreaction mixture. The reaction mixture was heated in a boiling water bath for 2 h until complete\ndissolution of the glucose. Then 100 ml of ice was added. After 1 hour, White crystals formed and\nwere washed with cold water. And then 1 mol of glucose pentaacetate per 50 ml of methanol was\ndissolved by a magnetic stirrer. After thatMgO (0.2gr) was added to the reaction mixture. The\nreaction mixture was refluxed at room temperature within 4-5 hours. After 5 hours, the solvent was\nremoved and separated by chromatography. It is then washed with hexane and crystallized by etherhexane. And the final step reacted with N-Methyl- (naphtha-2-ylmethoxy) amine in order to prepare\nnew glycosylamine derivatives.\n\n\n\nMagnesium oxide in methanol solvent is one of the best effective catalysts in the\ndeacetylation of the anomer position of acetylated carbohydrates. It is done under ambient temperature\nand in very easy conditions and makes carbohydrates susceptible to extensive chemical reactions. One\nof these reactions is the formation of glycosides. Various carbohydrates are acetylated by acetic\nanhydride in the presence of sodium acetate, and the anomeric position is deacetylated by a\nheterogeneous catalyst. In order to prepare N-glycoside, the glycosides are reacted with N-alkoxy Nmethylglycosyl amine. The final products are identified by various spectroscopic methods.\n\n\n\nGlucose, mannose, for example, were acetylated by acetic anhydride in the presence of\nsodium acetate. And the anomeric position of pentaacetate glucose was selectively deacetylated with\nmagnesium oxide in a methanol solvent. Then, the reaction for the preparation of glycosylamine derivatives was carried out under very mild and easy conditions. The aminoglycosides synthesized in\nthis article are used as raw materials for the synthesis of a wide range of antibacterials.\n","PeriodicalId":10772,"journal":{"name":"Current Bioactive Compounds","volume":null,"pages":null},"PeriodicalIF":0.0000,"publicationDate":"2023-08-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Current Bioactive Compounds","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.2174/1573407219666230810094657","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"Pharmacology, Toxicology and Pharmaceutics","Score":null,"Total":0}
引用次数: 0

Abstract

Glycosylamine play an important role in living organisms. Most plants store their chemical resources in the form of inactive glycosides, which are broken down and converted into sugar in the body of herbivores by hydrolyzing enzymes. Glycosylamine are obtained from the secondary metabolism of plants and consist of two parts. One part of it contains sugar like glucose and is inactive in most substances, and has a good effect on the solubility of the glycosylamine derivatives and its absorption and even its transfer from one organ to another. The therapeutic effect is related to the second part, which is called aglycan (or aglucan). Glycosylamine derivatives form a large group of valuable medicinal substances, which at the same time include some of the most dangerous and toxic substances in nature. These substances are present in many groups of flowering plants. Glycosides are made in different ways in different metabolic pathways. These materials have a complex and special chemical structure and leave special effects on the human body. Glycosylamine derivatives are called O-glycosid, N-glycosid, S-glycosid in terms of atoms coupling to anomeric carbon. Carbohydrate esterification reaction to prepare new glycosylamine derivatives is one of the most important carbohydrate reactions. The anomeric position of carbohydrates with strong leaving groups is very important for the preparation of glycosides. Preparation of glycosylamine derivatives based on acetylated carbohydrates is the main purpose of this article. Different carbohydrates were acetylated under mild conditions and high yields. The anomeric position was deacetylated by a magnesium oxide heterogeneous catalyst in methanol solvent. In order to prepare new glycosides acetylated/ deacytylated carbohydrate reacted with N-Methyl-(naphtha-2- ylmethoxy)amine. The final product was identified by various spectroscopic methods. Anhydrous sodium acetate (4 g) and α-D-glucose (28 mg, 5 g) were mixed. The mixture was transferred to a 200 ml Round-bottom flask . Acetic acid (260 mg, 25 ml) was added to the reaction mixture. The reaction mixture was heated in a boiling water bath for 2 h until complete dissolution of the glucose. Then 100 ml of ice was added. After 1 hour, White crystals formed and were washed with cold water. And then 1 mol of glucose pentaacetate per 50 ml of methanol was dissolved by a magnetic stirrer. After thatMgO (0.2gr) was added to the reaction mixture. The reaction mixture was refluxed at room temperature within 4-5 hours. After 5 hours, the solvent was removed and separated by chromatography. It is then washed with hexane and crystallized by etherhexane. And the final step reacted with N-Methyl- (naphtha-2-ylmethoxy) amine in order to prepare new glycosylamine derivatives. Magnesium oxide in methanol solvent is one of the best effective catalysts in the deacetylation of the anomer position of acetylated carbohydrates. It is done under ambient temperature and in very easy conditions and makes carbohydrates susceptible to extensive chemical reactions. One of these reactions is the formation of glycosides. Various carbohydrates are acetylated by acetic anhydride in the presence of sodium acetate, and the anomeric position is deacetylated by a heterogeneous catalyst. In order to prepare N-glycoside, the glycosides are reacted with N-alkoxy Nmethylglycosyl amine. The final products are identified by various spectroscopic methods. Glucose, mannose, for example, were acetylated by acetic anhydride in the presence of sodium acetate. And the anomeric position of pentaacetate glucose was selectively deacetylated with magnesium oxide in a methanol solvent. Then, the reaction for the preparation of glycosylamine derivatives was carried out under very mild and easy conditions. The aminoglycosides synthesized in this article are used as raw materials for the synthesis of a wide range of antibacterials.
基于碳水化合物的新型糖胺衍生物的合成
糖基胺在生物体中起着重要作用。大多数植物以非活性糖苷的形式储存其化学资源,这些糖苷在食草动物体内通过水解酶分解并转化为糖。糖基胺是从植物的次生代谢中获得的,由两部分组成。它的一部分含有类葡萄糖,在大多数物质中都没有活性,对葡糖胺衍生物的溶解度、吸收甚至从一个器官转移到另一个器官都有很好的影响。治疗效果与第二部分有关,第二部分被称为aglycan(或aglucan)。糖胺衍生物是一大类有价值的药用物质,同时也包括自然界中一些最危险、最有毒的物质。这些物质存在于许多开花植物中。糖苷在不同的代谢途径中以不同的方式产生。这些物质具有复杂而特殊的化学结构,对人体产生特殊影响。糖基胺衍生物被称为O-糖苷、N-糖苷、S-糖苷,就原子和异头碳的偶联而言。碳水化合物酯化反应制备新的糖胺衍生物是碳水化合物最重要的反应之一。具有强离去基团的碳水化合物的异头位置对于糖苷的制备非常重要。以乙酰化碳水化合物为原料制备糖胺衍生物是本文的主要目的。不同的碳水化合物在温和的条件下进行乙酰化并获得高产率。在甲醇溶剂中用氧化镁多相催化剂对异头位置进行脱乙酰。以N-甲基-(萘-2-基甲氧基)胺为原料,经乙酰化/脱酰化碳水化合物反应制备新的糖苷。通过各种光谱方法鉴定了最终产物。将无水乙酸钠(4 g)和α-D-葡萄糖(28 mg,5 g)混合。将混合物转移到200ml圆底烧瓶中。向反应混合物中加入乙酸(260mg,25ml)。将反应混合物在沸水浴中加热2小时,直到葡萄糖完全溶解。然后加入100毫升冰。1小时后,形成白色晶体,并用冷水洗涤。然后用磁力搅拌器溶解每50毫升甲醇1摩尔五乙酸葡萄糖。然后将MgO(0.2gr)加入到反应混合物中。将反应混合物在室温下在4-5小时内回流。5小时后,除去溶剂并通过色谱分离。然后用己烷洗涤并用醚己烷结晶。最后与N-甲基-(萘-2-基甲氧基)胺反应制备新的糖胺衍生物。甲醇溶剂中的氧化镁是乙酰化碳水化合物异头位置脱乙酰的最佳催化剂之一。它是在环境温度和非常简单的条件下进行的,使碳水化合物容易发生广泛的化学反应。这些反应之一是糖苷的形成。在乙酸钠存在下,各种碳水化合物通过乙酰氨酰化,异头位置通过异构催化剂脱乙酰。为了制备N-糖苷,糖苷与N-烷氧基N-甲基糖苷基胺反应。通过各种光谱方法鉴定最终产物。葡萄糖,例如甘露糖,在乙酸钠的存在下被乙酸酐乙酰化。在甲醇溶剂中用氧化镁对五乙酸葡萄糖的异头位置进行选择性脱乙酰。然后,在非常温和和容易的条件下进行制备糖胺衍生物的反应。本文合成的氨基糖苷类药物被用作合成多种抗菌药物的原料。
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来源期刊
Current Bioactive Compounds
Current Bioactive Compounds Pharmacology, Toxicology and Pharmaceutics-Pharmacology, Toxicology and Pharmaceutics (all)
CiteScore
1.90
自引率
0.00%
发文量
112
期刊介绍: The journal aims to provide comprehensive review articles on new bioactive compounds with proven activities in various biological screenings and pharmacological models with a special emphasis on stereoeselective synthesis. The aim is to provide a valuable information source of bioactive compounds synthesized or isolated, which can be used for further development of pharmaceuticals by industry and academia. The journal should prove to be essential reading for pharmacologists, natural product chemists and medicinal chemists who wish to be kept informed and up-to-date with the most important developments on new bioactive compounds of natural or synthetic origin, including their stereoeselective synthesis.
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