4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl sulfamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl sulfamide
• 英文别名: [(2R,3S,6S)-3-acetyloxy-6-(sulfamoylamino)-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• 化学式: C₁₀H₁₆N₂O₇S
• 分子量: 308.312
• InChiKey: HHTMGBZKMBVDFX-AEJSXWLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  142
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  乙酰化葡萄烯糖 在 三氟化硼乙醚 、 磺酰胺 作用下， 生成 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl sulfamide
  参考文献：
  名称：

  Carbonic anhydrase inhibitors. Inhibition of cytosolic isoforms I and II, and extracellular isoforms IV, IX, and XII with sulfamides incorporating sugar moieties

  摘要：

  A series of glycosylated sulfarnides possessing a diverse substitution pattern, with benzylated, peracetylated, and unsaturated six- and five-membered ring sugar moieties attached to the NHSO2NH2 zinc binding group is reported. These derivatives were tested for the inhibition of five human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms, hCA I, II, IV, IX, and XII. Against hCA I the sulfamides behaved as weak inhibitors, whereas they showed low nanomolar activity against hCA II, IX, and XII, being slightly less effective as hCA IV inhibitors. One compound showed selectivity for inhibiting the tumor-associated isoforms hCA IX and XII over the ubiquitous cytosolic hCA II. The sulfamide zinc binding group may thus indeed lead to very effective glycosylated inhibitors targeting several physiologically relevant isozymes. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.07.023

文献信息

• Synthesis of 2,3-Unsaturated O- and N-Glycosides by HBF4˙SiO2-Catalyzed Ferrier Rearrangement of d-Glycals
  作者：Pedro Colinas、Oscar Rodríguez、Rodolfo Bravo

  DOI：10.1055/s-0028-1088105

  日期：2009.4

  Fluoroboronic acid adsorbed on silica gel (HBF4˙SiO2) catalyzes the Ferrier rearrangement of per-O-acetylated glycals with alcohols and sulfonamides to give 2,3-unsaturated O- and N-glycosides in good to excellent yield and with high α-stereoselectivity.

  氟硼酸吸附于硅胶上（HBF4⋅SiO2）催化佛雷尔重排反应，在醇和磺酰胺作用下生成2,3-不饱和的O-和N-糖苷，产率优良至极佳，并具有高度的α-立体选择性。
• Ferrier sulfonamidoglycosylation of d-glycals
  作者：Pedro A. Colinas、Rodolfo D. Bravo

  DOI：10.1016/j.carres.2007.06.027

  日期：2007.11

  A series of novel N-glycosyl sulfonamides were prepared via Ferrier sulfonamidoglycosylation of D-glycals with good to high alpha-stereo selectivity. Two new glycosylsulfamides were tested as carbonic anhydrase (CA II) inhibitors and showed good properties in the micromolar range. (C) 2007 Elsevier Ltd. All rights reserved.
• Carbonic anhydrase inhibitors. Inhibition of cytosolic isoforms I and II, and extracellular isoforms IV, IX, and XII with sulfamides incorporating sugar moieties
  作者：Pedro A. Colinas、Rodolfo D. Bravo、Daniela Vullo、Andrea Scozzafava、Claudiu T. Supuran

  DOI：10.1016/j.bmcl.2007.07.023

  日期：2007.9

  A series of glycosylated sulfarnides possessing a diverse substitution pattern, with benzylated, peracetylated, and unsaturated six- and five-membered ring sugar moieties attached to the NHSO2NH2 zinc binding group is reported. These derivatives were tested for the inhibition of five human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms, hCA I, II, IV, IX, and XII. Against hCA I the sulfamides behaved as weak inhibitors, whereas they showed low nanomolar activity against hCA II, IX, and XII, being slightly less effective as hCA IV inhibitors. One compound showed selectivity for inhibiting the tumor-associated isoforms hCA IX and XII over the ubiquitous cytosolic hCA II. The sulfamide zinc binding group may thus indeed lead to very effective glycosylated inhibitors targeting several physiologically relevant isozymes. (c) 2007 Elsevier Ltd. All rights reserved.