NSC 106217 | 33797-75-0

• 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: NSC 106217
• 英文别名: 1,3-dimethyl-8-(thiophen-2-yl)-2,3,6,7-tetrahydro-1H-purine-2,6-dione；ODC-MPI-2；1,3-dimethyl-8-thiophen-2-yl-3,7(9)-dihydro-purine-2,6-dione；8-<2-Thienyl>-theophyllin；8-(2-Thienyl)-theophyllin；8-(2-Thienyl)theophylline；1,3-dimethyl-8-thiophen-2-yl-7H-purine-2,6-dione
• CAS: 33797-75-0
• 化学式: C₁₁H₁₀N₄O₂S
• 分子量: 262.292
• InChiKey: XKANLKMBLCBGOJ-UHFFFAOYSA-N

物化性质

• 沸点：
  536.4±48.0 °C(Predicted)
• 密度：
  1.476±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 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：
  97.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  NSC 106217 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以75%的产率得到1,3,7-Trimethyl-8-thiophen-2-ylpurine-2,6-dione
  参考文献：
  名称：

  Immunosuppressive effects of 8-substituted xanthine derivatives

  摘要：

  这项发明涉及使用8-取代黄嘌呤衍生物制造治疗自身免疫性疾病药物的新方法。

  公开号：

  US07253176B1
• 作为产物：
  描述：

  5,6-二氨基-1,3-二甲基脲嘧啶 在 吡啶 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 NSC 106217
  参考文献：
  名称：

  Sulfur-containing 1,3-dialkylxanthine derivatives as selective antagonists at A1-adenosine receptors

  摘要：

  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.

  DOI：

  10.1021/jm00128a031

文献信息

• 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）。
• Thio-analogues of 6-Substituted 1, 3-Dimethyl-7-azalumazine (Fervenulin) and 7-Substituted 1, 3-Dimethyl-6-azalumazine (Isofervenulin)
  作者：FUMIO YONEDA、YOSHIHARU SAKUMA、MICHIKO UENO、SADAO NISHIGAKI

  DOI：10.1248/cpb.21.926

  日期：——

  1, 3-Dimethyl-4-thio-7-azalumazine derivatives (5-thiofervenulins) and 1, 3-dimethyl-4-thio-6-azalumazine derivatives (5-thioisofervenulins) were synthesized by the thiation of 1, 3-dimethyl-7-azalumazine derivatives (fervenulins) and 1, 3-dimethyl-6-azalumazine derivatives (isofervenulins). The 1, 3-dimethyl-4-thio-6-azalumazines were converted into theophyllines by treatment with sodium dithionite in formic acid. These thio-azalumazines displayed low antibacterial activities in vitro.

  通过 1, 3-二甲基硫杂化反应合成 1, 3-二甲基-4-硫代-7-氮杂嗪衍生物（5-硫代铁维素）和 1, 3-二甲基-4-硫代-6-氮杂嗪衍生物（5-硫代异铁维素） -7-氮杂氮嗪衍生物（fervenulins）和1, 3-二甲基-6-氮杂氮嗪衍生物（isofervenulins）。通过用甲酸中的连二亚硫酸钠处理将1, 3-二甲基-4-硫代-6-氮杂嗪转化为茶碱。这些硫代氮杂氮嗪在体外表现出较低的抗菌活性。
• Immunosuppressive effects of 8-substituted xanthine derivatives
  申请人：K.U. Leuven Research & Development

  公开号：US07253176B1

  公开（公告）日：2007-08-07

  The invention relates to a novel use of 8-substituted xanthine derivatives for the manufacture of a medicament for the treatment of auto-immuno disorders.

  这项发明涉及使用8-取代黄嘌呤衍生物制造治疗自身免疫性疾病药物的新方法。
• 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.