8-bromo-1,3-dimethyl-7-(thietanyl-3)xanthine | 136265-48-0

• 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: 8-bromo-1,3-dimethyl-7-(thietanyl-3)xanthine
• 英文别名: 8-bromo-1,3-dimethyl-7-(thietan-3-yl)-1H-purine-2,6-(3H,7H)-dione；8-Bromo-1,3-dimethyl-7-(thietan-3-yl)-1h-purine-2,6(3h,7h)-dione；8-bromo-1,3-dimethyl-7-(thietan-3-yl)purine-2,6-dione
• CAS: 136265-48-0
• 化学式: C₁₀H₁₁BrN₄O₂S
• 分子量: 331.193
• InChiKey: XWZUWGDAKLDJML-UHFFFAOYSA-N

物化性质

• 沸点：
  544.3±60.0 °C(Predicted)
• 密度：
  2.00±0.1 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：
  0.5
• 拓扑面积：
  83.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-bromo-1,3-dimethyl-7-(thietanyl-3)xanthine 在 双氧水 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 0.5h， 以68%的产率得到8-bromo-1,3-dimethyl-7-(1,1-dioxothietan-3-yl)-3,7-dihydro-1H-pyrine-2,6-dione
  参考文献：
  名称：

  Thietanyl protection in the synthesis of 1-alkyl-8-bromo-3-methyl-3,7-dihydro-1H-purine-2,6-diones

  摘要：

  The protection of the 7-NH group in 8-bromo-3-methyl-3,7-dihydro-1H-pyrine-2,6-dione during the synthesis of 7-ubsubstituted 1-alkyl-8-bromo-3-methyl-3,7-dihydro-1H-pyrine-2,6-diones with a thienyl group was applied that was introduced by the reaction with 2-chloromethylthiirane. The thietanyl protection was removed by treating with sodium alcoholate after the oxidation with hydrogen peroxide to thietane 1,1-dioxide group.

  DOI：

  10.1134/s1070428010050167
• 作为产物：
  描述：

  8-bromo-3-methyl-7-(thietan-3-yl)-1H-purine-2,6(3H,7H)-dione 、 碘甲烷 在 氢氧化钾 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以66%的产率得到8-bromo-1,3-dimethyl-7-(thietanyl-3)xanthine
  参考文献：
  名称：

  Thietane ring as a novel protecting group

  摘要：

  A novel protecting group for NH functionality of heterocycles, a thietane ring, was proposed. It can be readily introduced by alkylation of NH-heterocycles with 2-chloromethylthiirane. Removal of the thietane protecting group is performed via oxidation to thietane 1,1-dioxide with hydrogen peroxide in acetic acid and subsequent treatment with sodium alkoxide.

  DOI：

  10.1134/s1070428009010187

文献信息

• Synthesis and Antidiabetic Activity of Thiazolo[2,3-f]Purine Derivatives and Their Analogs
  作者：A. A. Spasov、F. A. Khaliullin、D. A. Babkov、G. A. Timirkhanova、V. A. Kuznetsova、L. V. Naumenko、D. R. Muleeva、O. Yu. Maika、T. Yu. Prokhorova、E. A. Sturova

  DOI：10.1007/s11094-017-1649-5

  日期：2017.10

  3-f]purine derivatives and their analogs – dihydrothiazolo[2, 3-f]purine, 7-(thietan-3-yl)purine, and 8-(2-hydroxypropylthio)purine derivatives – were synthesized. The compounds synthesized here had no effects on protein glycation reactions using glucose; they gave weak inhibition of glycogen phosphorylase; they had no hemorheological activity. Substances with hypotensive activity greater than that of Dibazol

  合成了噻唑并[2, 3-f]嘌呤衍生物及其类似物——二氢噻唑并[2, 3-f]嘌呤、7-(thietan-3-yl)嘌呤和8-(2-羟基丙硫基)嘌呤衍生物。这里合成的化合物对使用葡萄糖的蛋白质糖化反应没有影响；它们对糖原磷酸化酶的抑制作用较弱；他们没有血液流变学活动。发现了降血压活性大于地巴唑的物质。许多物质的降血糖作用比氯丙胺和 Adebit 的作用更大。两种化合物抑制二肽基肽酶-4，但活性低于参考药物维格列汀。
• Unusual Reaction of 8-Bromo-3-methyl-7-(thietan-3-yl)3,7-dihydro-1H-purine-2,6-diones with Trisamine in Dimethylformamide
  作者：F. А. Khaliullin、Yu. V. Shabalina

  DOI：10.1134/s1070428020020049

  日期：2020.2

  The reaction of 8-bromo-substituted 3-methyl-7-(thietan-3-yl)-3,7-dihydro-1H-purine-2,6-diones with trisamine in DMF gave, instead of the expected 8-tris(hydroxymethyl)methylamino-substituted products, 8-dimethylamino-substituted 3-methyl-7-(thietan-3-yl)-3,7-dihydro-1H-purine-2,6-diones. The formation of unusual reaction products was explained by the initial reaction of DMF with trisamine to form dimethylamine and subsequent nucleophilic substitution reaction of the latter with the bromine atom.
• Alkylation of xanthine and benzimidazole derivatives with epithiochlorohydrin
  作者：F. A. Khaliuliin、V. A. Kataev、Yu. V. Strokin

  DOI：10.1007/bf00480840

  日期：1991.4
• Synthesis and antiinflammatory activity of 8-substituted 7-[thietanyl-3]theophyllines
  作者：F. A. Khaliullin、Yu. V. Strokin、Kh. M. Nasyrov、K. M. Farztdinov

  DOI：10.1007/bf00770624

  日期：1992.9
• XALIULLIN, F. A.;NAZIPOV, N. M.;MIRONENKOVA, ZH. V.;DAVLETYAROVA, A. B., SINTEZ I DOKLIN. IZUCH. HOB. BIOL. AKTIV. VESHCHESTV, UFA,(1988) S. 9-11
  作者：XALIULLIN, F. A.、NAZIPOV, N. M.、MIRONENKOVA, ZH. V.、DAVLETYAROVA, A. B.

  DOI：——

  日期：——