ethyl 3-amino-2-[(2S,3S,4R,5R)-3,4-diacetyloxy-5-(acetyloxymethyl)oxolan-2-yl]sulfanyl-5-methyl-4-oxothieno[2,3-d]pyrimidine-6-carboxylate | 1224375-09-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 3-amino-2-[(2S,3S,4R,5R)-3,4-diacetyloxy-5-(acetyloxymethyl)oxolan-2-yl]sulfanyl-5-methyl-4-oxothieno[2,3-d]pyrimidine-6-carboxylate
• CAS: 1224375-09-0
• 化学式: C₂₁H₂₅N₃O₁₀S₂
• 分子量: 543.576
• InChiKey: ZPFQZBJTZHJNFX-AUKZQPGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  227
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  ethyl 3-amino-2-[(2S,3S,4R,5R)-3,4-diacetyloxy-5-(acetyloxymethyl)oxolan-2-yl]sulfanyl-5-methyl-4-oxothieno[2,3-d]pyrimidine-6-carboxylate 在 氨 、 sodium methylate 作用下， 以 甲醇 、 水 为溶剂， 反应 0.17h， 以44%的产率得到ethyl 3-amino-2-[(2S,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]sulfanyl-5-methyl-4-oxothieno[2,3-d]pyrimidine-6-carboxylate
  参考文献：
  名称：

  Synthesis, biological and medicinal significance of S-glycosido-thieno[2,3-d]-pyrimidines as new anti-inflammatory and analgesic agents

  摘要：

  Several 2-thioglycosides were prepared. Glycosylation of 2-thioxo-thieno[2,3-d]-pyrimidines 5a,b with 1-bromo-2,3,5-tri-O-acetyl-alpha-D-arabinofuranosyle 7, 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl and galacto-pyranosyl bromide 8a,b gave the protected beta-n-nuclosides 10a,b and 13a-d in high yields, which were transformed to deacetylated derivatives 14a,b and 15a-d. The structures of the compounds were elucidated by spectral and elemental analysis. Anti-inflammatory and Analgesic activities screening of the new compounds (at a dose of 100 mg/kg body weight) utilizing in vivo acute carrageenan-induced paw oedema standard method exhibited that the deacetylated derivatives 14a,b and 15a-d possess highly promising activities. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.12.056
• 作为产物：
  描述：

  2,3,5-tri-O-acetyl-α-D-arabinofuranosyl bromide 、 3-amino-5-methyl-4-oxo-2-thioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-6-carboxylic acid ethyl ester 在 potassium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 反应 24.0h， 以67%的产率得到ethyl 3-amino-2-[(2S,3S,4R,5R)-3,4-diacetyloxy-5-(acetyloxymethyl)oxolan-2-yl]sulfanyl-5-methyl-4-oxothieno[2,3-d]pyrimidine-6-carboxylate
  参考文献：
  名称：

  Synthesis, biological and medicinal significance of S-glycosido-thieno[2,3-d]-pyrimidines as new anti-inflammatory and analgesic agents

  摘要：

  Several 2-thioglycosides were prepared. Glycosylation of 2-thioxo-thieno[2,3-d]-pyrimidines 5a,b with 1-bromo-2,3,5-tri-O-acetyl-alpha-D-arabinofuranosyle 7, 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl and galacto-pyranosyl bromide 8a,b gave the protected beta-n-nuclosides 10a,b and 13a-d in high yields, which were transformed to deacetylated derivatives 14a,b and 15a-d. The structures of the compounds were elucidated by spectral and elemental analysis. Anti-inflammatory and Analgesic activities screening of the new compounds (at a dose of 100 mg/kg body weight) utilizing in vivo acute carrageenan-induced paw oedema standard method exhibited that the deacetylated derivatives 14a,b and 15a-d possess highly promising activities. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.12.056

文献信息

• Synthesis, biological and medicinal significance of S-glycosido-thieno[2,3-d]-pyrimidines as new anti-inflammatory and analgesic agents
  作者：Hend N. Hafez、Abdel-Rahman B.A. El-Gazzar、Galal A.M. Nawwar

  DOI：10.1016/j.ejmech.2009.12.056

  日期：2010.4

  Several 2-thioglycosides were prepared. Glycosylation of 2-thioxo-thieno[2,3-d]-pyrimidines 5a,b with 1-bromo-2,3,5-tri-O-acetyl-alpha-D-arabinofuranosyle 7, 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl and galacto-pyranosyl bromide 8a,b gave the protected beta-n-nuclosides 10a,b and 13a-d in high yields, which were transformed to deacetylated derivatives 14a,b and 15a-d. The structures of the compounds were elucidated by spectral and elemental analysis. Anti-inflammatory and Analgesic activities screening of the new compounds (at a dose of 100 mg/kg body weight) utilizing in vivo acute carrageenan-induced paw oedema standard method exhibited that the deacetylated derivatives 14a,b and 15a-d possess highly promising activities. (C) 2010 Elsevier Masson SAS. All rights reserved.