1,3-dimethyl-8-(2-furyl)-9(H)-xanthine | 33797-74-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 1,3-dimethyl-8-(2-furyl)-9(H)-xanthine
• 英文别名: 8-(Furan-2-yl)-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione；8-(furan-2-yl)-1,3-dimethyl-7H-purine-2,6-dione
• CAS: 33797-74-9
• 化学式: C₁₁H₁₀N₄O₃
• 分子量: 246.225
• InChiKey: LQKQPUSYFFEBGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  82.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5,6-二氨基-1,3-二甲基脲嘧啶 在 间氯过氧苯甲酸 作用下， 以 乙醇 、 乙腈 为溶剂， 生成 1,3-dimethyl-8-(2-furyl)-9(H)-xanthine
  参考文献：
  名称：

  De Araujo, Aline D.; Bacher, Edmond; Joachim Demnitz, Heterocycles, 1999, vol. 51, # 1, p. 29 - 36

  摘要：

  DOI：

文献信息

• A facile and rapid one-step synthesis of 8-substituted xanthine derivatives via tandem ring closure at room temperature
  作者：Prabal Bandyopadhyay、Sumit K. Agrawal、Manisha Sathe、Pratibha Sharma、M.P. Kaushik

  DOI：10.1016/j.tet.2012.03.050

  日期：2012.5

  N-Bromo succinimide (NBS) was found to be an efficient and regioselective reagent in combination with AIBN for an unprecedented, facile and rapid one-step synthesis of 8-substituted xanthine derivatives at room temperature. The inexpensive, nontoxic and readily available NBS efficiently promoted the condensation of several aryl/cycloaryl/heteroaryl aldehydes with 5,6-diamino-1,3-dimethyluracils in

  N-溴代琥珀酰亚胺（NBS）与AIBN结合使用是一种高效且区域选择性的试剂，可在室温下空前，简便，快速地一步合成8-取代的黄嘌呤衍生物。在催化量的AIBN存在下，通过自由基链反应，在一步催化过程中，廉价，无毒且易于获得的NBS有效地促进了几种芳基/环芳基/杂芳基醛与5,6-二氨基-1,3-二甲基尿嘧啶的缩合。该方案的显着优点是反应时间短，反应条件温和，后处理简单，无需色谱分离，使用无害试剂/溶剂且适用于多种底物。
• Synthesis and properties of 1,3-dimethyl-6-azalumazines (Isofervenulins).
  作者：FUMIO YONEDA、TOMOHISA NAGAMATSU、KAZUKO OGIWARA、MICHIKO KANAHORI、SADAO NISHIGAKI、EDWARD C. TAYLOR

  DOI：10.1248/cpb.26.367

  日期：——

  A new synthesis of 1, 3-dimethyl-6-azalumazines (isofervenulins) is described. The reaction of 6-amino-1, 3-dimethyl-5-nitrosouracil (I) with acid hydrazides in refluxing aprotic solvents such as dimethylformamide (DMF), dimethyl sulfoxide (DMSO) or sulfolane affords the corresponding 1, 3-dimethyl-6-azalumazines (II) along with byproducts, 2, 4, 9, 11-tetramethyl-8-azapurino [7, 8-f]-6-azapteridine-1, 3, 10, 12 (2H, 4H, 9H, -11H)-tetrones (III). These 8-azapurino [7, 8-f]-6-azapteridines were alternatively prepared by the condensation of II with 6-amino-1, 3-dimethyluracil in refluxing DMF. Compounds II were converted into 8-substituted theophyllines (V) by reductive ring contraction with sodium dithionite in formic acid.

  描述了一种新的1, 3-二甲基-6-氮杂呋喃类化合物（异佛尔嫩）合成方法。6-氨基-1, 3-二甲基-5-亚硝基尿嘧啶（I）与酸性肼在回流的无原子溶剂中（如二甲基甲酰胺（DMF）、二甲基亚砜（DMSO）或磺烷）反应，生成相应的1, 3-二甲基-6-氮杂呋喃类化合物（II），以及副产品2, 4, 9, 11-四甲基-8-氮杂嘌呤[7, 8-f]-6-氮基哌啶-1, 3, 10, 12（2H, 4H, 9H, -11H）-四烯酮（III）。这些8-氮杂嘌呤[7, 8-f]-6-氮基哌啶也可以通过将II与6-氨基-1, 3-二甲基尿嘧啶在回流的DMF中缩合制备。化合物II通过在甲酸中与亚硫酸钠进行还原环收缩反应转化为8-取代茶碱（V）。
• Synthesis, DNA Binding and Antiviral Activity of New Uracil, Xanthine, and Pteridine Derivatives
  作者：Osama I. El-Sabbagh、Mohamed E. El-Sadek、Samar El-Kalyoubi、Ibrahim Ismail

  DOI：10.1002/ardp.200600149

  日期：2007.1

  Some new 6‐amino‐1,3‐dimethyl‐5‐(substituted methylidene)aminouracils were synthesized. Most of them were cyclized with triethyl orthoformate as a one‐carbon source to afford 1,3‐dimethyl‐6‐substituted pteridine derivatives. Certain uracils gave xanthine instead of the expected pteridine derivatives upon using another one‐carbon source such as triethyl orthoacetate or triethyl orthobenzoate. The nucleic

  合成了一些新的6-氨基-1,3-二甲基-5-（取代亚甲基）氨基尿嘧啶。它们中的大多数与原甲酸三乙酯作为单碳源环化，得到 1,3-二甲基-6-取代的蝶啶衍生物。某些尿嘧啶在使用另一种单碳源（如原乙酸三乙酯或原苯甲酸三乙酯）时产生黄嘌呤而不是预期的蝶啶衍生物。核酸结合试验表明，与仅对 DNA 具有亲和力的阿昔洛韦相反，一些新化合物显示出高亲和力、螯合和核酸片段化，无论是 DNA 还是 RNA。这些新型化合物的抗病毒活性表明，化合物 2e 和 2f 分别将 Vero 细胞培养物中小反刍兽疫病毒 (PPRV) 的细胞致病性降低了 60% 和 50%。
• Exploration of polystyrene-supported 2-isobutoxy-1-isobutoxycarbonyl-1,2-dihydroquinoline (PS-IIDQ) as new coupling agent for the synthesis of 8-substituted xanthine derivatives
  作者：Prabal Bandyopadhyay、Manisha Sathe、Pratibha Sharma、M.P. Kaushik

  DOI：10.1016/j.tetlet.2012.04.135

  日期：2012.8

  Polystyrene-supported 2-isobutoxy-1-isobutoxycarbonyl-1,2-dihydroquinoline (PS-IIDQ), a polymer supported covalent coupling reagent, was successfully employed for the first time in the synthesis of 8-substituted xanthine derivatives. PS-IIDQ was observed to be more efficient than IIDQ and polymer-supported carbodiimide (PS-EDC). (C) 2012 Elsevier Ltd. All rights reserved.
• Sulfur-containing 1,3-dialkylxanthine derivatives as selective antagonists at A1-adenosine receptors
  作者：Kenneth A. Jacobson、Leonidas Kiriasis、Suzanne Barone、Barton J. Bradbury、Udai Kammula、Jean Michel Campagne、John W. Daly、John L. Neumeyer、Wolfgang Pfleiderer、Sherrie Secunda

  DOI：10.1021/jm00128a031

  日期：1989.8

  Sulfur-containing analogues of 8-substituted xanthines were prepared in an effort to increase selectivity or potency as antagonists at adenosine receptors. Either cyclopentyl or various aryl substituents were utilized at the 8-position, because of the association of these groups with high potency at A1-adenosine receptors. Sulfur was incorporated on the purine ring at positions 2 and/or 6, in the 8-position substituent in the form of 2- or 3-thienyl groups, or via thienyl groups separated from an 8-aryl substituent through an amide-containing chain. The feasibility of using the thienyl group as a prosthetic group for selective iodination via its Hg2+ derivative was explored. Receptor selectivity was determined in binding assays using membrane homogenates from rat cortex [( 3H]-N6-(phenylisopropyl)adenosine as radioligand] or striatum [3H]-5'-(N-ethylcarbamoyl)adenosine as radioligand] for A1- and A2-adenosine receptors, respectively. Generally, 2-thio-8-cycloalkylxanthines were at least as A1 selective as the corresponding oxygen analogue. 2-Thio-8-aryl derivatives tended to be more potent at A2 receptors than the oxygen analogue. 8-[4-[(Carboxy-methyl)oxyl] phenyl]-1,3-dipropyl-2-thioxanthine ethyl ester was greater than 740-fold A1 selective.