2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl sulfamide | 1210451-91-4

• 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: 2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl sulfamide
• 英文别名: [(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(sulfamoylamino)oxan-2-yl]methyl acetate
• CAS: 1210451-91-4
• 化学式: C₁₄H₂₂N₂O₁₁S
• 分子量: 426.401
• InChiKey: XKXQWYYDHMYBIX-PEBLQZBPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  195
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl sulfamide 在 甲醇 、 sodium methylate 作用下， 生成 C₆H₁₄N₂O₇S
  参考文献：
  名称：

  N-β-Glycosyl sulfamides are selective inhibitors of the cancer associated carbonic anhydrase isoforms IX and XII

  摘要：

  The transmembrane isoforms of carbonic anhydrase (CA IX and XII) have been shown to be linked to carcinogenesis and their inhibition to arrest primary tumor and metastases growth. In this Letter, we present a series of peracetylated and deprotected N-beta-glycosyl sulfamides that were tested for the inhibition of 4 carbonic anhydrase isoforms: the cytosolic hCA I and hCA II and transmembrane tumor-associated IX and XII. Compounds 1-4 and 6-8 selectively target cancer-associated CAs (IX and XII) with KIs in the low nanomolar range. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.031
• 作为产物：
  描述：

  Α-D-五乙酸甘露糖酯 在 三氟化硼乙醚 、 磺酰胺 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以78%的产率得到2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl sulfamide
  参考文献：
  名称：

  Stereoselective Synthesis of Novel N-β-Glycosyl Sulfonamides by Sulfonamidoglycosylation of Per-O-acetylated Sugars

  摘要：

  一系列新型N-糖苷磺酰胺通过全-O-乙酰化糖的磺酰胺糖苷化反应制备而成。这些在同位素中心含有非天然磺酰胺基团的产物以非常好的产率和优异的β-立体选择性获得，即使是在全-O-乙酰化的d-甘露糖中也是如此。

  DOI：

  10.1055/s-0029-1217045

文献信息

• Stereoselective Synthesis of Novel N-β-Glycosyl Sulfonamides by Sulfonamidoglycosylation of Per-O-acetylated Sugars
  作者：Pedro Colinas、Carlos Témpera、Oscar Rodríguez、Rodolfo Bravo

  DOI：10.1055/s-0029-1217045

  日期：——

  A series of novel N-glycosyl sulfonamides is prepared by sulfonamidoglycosylation of per-O-acetylated sugars. The products which contain an unnatural sulfonamide moiety at the anomeric centre are obtained in very good yields and with excellent β-stereoselectivity, even with per-O-acetylated d-mannose.

  一系列新型N-糖苷磺酰胺通过全-O-乙酰化糖的磺酰胺糖苷化反应制备而成。这些在同位素中心含有非天然磺酰胺基团的产物以非常好的产率和优异的β-立体选择性获得，即使是在全-O-乙酰化的d-甘露糖中也是如此。
• N-β-Glycosyl sulfamides are selective inhibitors of the cancer associated carbonic anhydrase isoforms IX and XII
  作者：Oscar M. Rodríguez、Alfonso Maresca、Carlos A. Témpera、Rodolfo D. Bravo、Pedro A. Colinas、Claudiu T. Supuran

  DOI：10.1016/j.bmcl.2011.06.031

  日期：2011.8

  The transmembrane isoforms of carbonic anhydrase (CA IX and XII) have been shown to be linked to carcinogenesis and their inhibition to arrest primary tumor and metastases growth. In this Letter, we present a series of peracetylated and deprotected N-beta-glycosyl sulfamides that were tested for the inhibition of 4 carbonic anhydrase isoforms: the cytosolic hCA I and hCA II and transmembrane tumor-associated IX and XII. Compounds 1-4 and 6-8 selectively target cancer-associated CAs (IX and XII) with KIs in the low nanomolar range. (C) 2011 Elsevier Ltd. All rights reserved.