(E)-4-[3-(3-phenylureido)phenyl]-1-[1'-deoxy-2',3',4',6'-tetra-O-acetyl-β-D-glucopyranos-1'-yl]but-3-en-2-one | 1426398-83-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-4-[3-(3-phenylureido)phenyl]-1-[1'-deoxy-2',3',4',6'-tetra-O-acetyl-β-D-glucopyranos-1'-yl]but-3-en-2-one
• 英文别名: (E)-4-[3-(3-phenylureido)phenyl]-1-[1′-deoxy-2′,3′,4′,6′-tetra-O-acetyl-β-D-glucopyranos-1′-yl]but-3-en-2-one；[(2R,3R,4R,5S,6S)-3,4,5-triacetoxy-6-[(E)-2-oxo-4-[3-(phenylcarbamoylamino)phenyl]but-3-enyl]tetrahydropyran-2-yl]methyl acetate；[(2R,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-[(E)-2-oxo-4-[3-(phenylcarbamoylamino)phenyl]but-3-enyl]oxan-2-yl]methyl acetate
• CAS: 1426398-83-5
• 化学式: C₃₁H₃₄N₂O₁₁
• 分子量: 610.618
• InChiKey: DIFXRDAPLNPUHK-UOMMZXSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  44
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  173
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (E)-4-[3-(3-phenylureido)phenyl]-1-[1'-deoxy-2',3',4',6'-tetra-O-acetyl-β-D-glucopyranos-1'-yl]but-3-en-2-one 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以76%的产率得到(E)-4-[3-(3-phenylureido)phenyl]-1-[1′-deoxy-β-D-glucopyranos-1′-yl]but-3-en-2-one
  参考文献：
  名称：

  Identification of Novel Phenyl Butenonyl C-Glycosides with Ureidyl and Sulfonamidyl Moieties as Antimalarial Agents

  摘要：

  A new series of C-linked phenyl butenonyl glycosides bearing ureidyl(thioureidyl) and sulfonamidyl moieties in the phenyl rings were designed, synthesized, and evaluated for their in vitro antimalarial activities against Plasmodium falciparum 3D7 (CQ sensitive) and K1 (CQ resistant) strains. Among all the compounds screened the C-linked phenyl butenonyl glycosides bearing sulfonamidyl moiety (5a) and ureidyl moiety in the phenyl ring (7d and 8c) showed promising antimalarial activities against both 3D7 and K1 strains with IC50 values in micromolar range and low cytotoxicity offering new HITS for further exploration.

  DOI：

  10.1021/ml500211c
• 作为产物：
  描述：

  1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)propane-2-one 在 四氢吡咯 、 tin(II) chloride dihdyrate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 120.0h， 生成 (E)-4-[3-(3-phenylureido)phenyl]-1-[1'-deoxy-2',3',4',6'-tetra-O-acetyl-β-D-glucopyranos-1'-yl]but-3-en-2-one
  参考文献：
  名称：

  在超声振动下从硝基苯基 2-oxobut-3-enyl C-glycopyranosides 化学选择性合成多功能氨基苯基 2-oxobut-3-enyl- 和 quinolinylmethyl-C-glycopyranosides

  摘要：

  在超声波振动下成功地实现了多功能硝基苯基 2-oxobut-3-enyl C-glycopyranosides 中硝基的化学选择性还原为相应的氨基苯基 2-ox obut-3-enyl glycopyranosides 和 SnCl 2.2H 2O。其他潜在的可还原基团，如羰基、酯、叠氮化物、甲苯磺酰基、烯基取代基在反应过程中不受影响。2'-硝基苯基-2-oxobut-3-enyl glycopyranosides 作为还原底物，通过还原和分子内环缩合反应得到 2-quinolinemethyl pyranosides。这些 β-C-吡喃糖苷在药物化学中具有广阔的前景。

  DOI：

  10.3998/ark.5550190.0014.213

文献信息

• Chemoselective synthesis of polyfunctional aminophenyl 2-oxobut-3-enyl - and quinolinylmethyl- C-glycopyranosides from nitrophenyl 2-oxobut-3-enyl C-glycopyranosides under ultrasonic vibration
  作者：K. Kumar G. Ramakrishna、Arya Ajay、Anindra Sharma、Rama P. Tripathi

  DOI：10.3998/ark.5550190.0014.213

  日期：——

  Chemoselective reduction of nitro group in polyfunc tional nitrophenyl 2-oxobut-3-enyl C- glycopyranosides to the respective aminophenyl 2-ox obut-3-enyl glycopyranosides with SnCl 2.2H 2O under ultrasonic vibration in good yields was ach ieved successfully. Other potentially reducible groups such as carbonyl, este r, azide, tosyl, alkenic substituents were unaffected during reaction. The 2 '-nitr

  在超声波振动下成功地实现了多功能硝基苯基 2-oxobut-3-enyl C-glycopyranosides 中硝基的化学选择性还原为相应的氨基苯基 2-ox obut-3-enyl glycopyranosides 和 SnCl 2.2H 2O。其他潜在的可还原基团，如羰基、酯、叠氮化物、甲苯磺酰基、烯基取代基在反应过程中不受影响。2'-硝基苯基-2-oxobut-3-enyl glycopyranosides 作为还原底物，通过还原和分子内环缩合反应得到 2-quinolinemethyl pyranosides。这些 β-C-吡喃糖苷在药物化学中具有广阔的前景。
• Identification of Novel Phenyl Butenonyl <i>C</i>-Glycosides with Ureidyl and Sulfonamidyl Moieties as Antimalarial Agents
  作者：K. Kumar G. Ramakrishna、Sarika Gunjan、Akhilesh Kumar Shukla、Venkata Reddy Pasam、Vishal M. Balaramnavar、Abhisheak Sharma、Swati Jaiswal、Jawahar Lal、Renu Tripathi、Anubhooti、Ravishankar Ramachandran、Rama Pati Tripathi

  DOI：10.1021/ml500211c

  日期：2014.8.14

  A new series of C-linked phenyl butenonyl glycosides bearing ureidyl(thioureidyl) and sulfonamidyl moieties in the phenyl rings were designed, synthesized, and evaluated for their in vitro antimalarial activities against Plasmodium falciparum 3D7 (CQ sensitive) and K1 (CQ resistant) strains. Among all the compounds screened the C-linked phenyl butenonyl glycosides bearing sulfonamidyl moiety (5a) and ureidyl moiety in the phenyl ring (7d and 8c) showed promising antimalarial activities against both 3D7 and K1 strains with IC50 values in micromolar range and low cytotoxicity offering new HITS for further exploration.