ethyl 5-amino-5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-α-D-xylo-1,4-heptofuranuronate | 500908-08-7

• 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 5-amino-5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-α-D-xylo-1,4-heptofuranuronate
• 英文别名: ethyl [5-amino-3-O-methyl-5,6-dideoxy-1,2-O-isopropylidene]-heptofuranuronate；3-Amino-3-((3aR,5R,6S,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-propionic acid, ethyl ester；ethyl 3-[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-3-aminopropanoate
• CAS: 500908-08-7
• 化学式: C₁₃H₂₃NO₆
• 分子量: 289.329
• InChiKey: JDNRSDVCBSYGHV-DDRLPIAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  89.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 5-amino-5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-α-D-xylo-1,4-heptofuranuronate 在 水 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 50.0h， 以91%的产率得到5-amino-5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-heptofuranuronic acid
  参考文献：
  名称：

  Synthesis of glycosylated β-amino acids as new class of antitubercular agents

  摘要：

  A series of glycosylated P-amino acids was prepared and evaluated against Mycohacterium tuberculosis, M. avium, M. fortuitum and M. smegmatis. The compounds were designed to mimic the enzyme D-alanine racemase and glycosyl transferase involved in the biosynthesis of essential cell wall peptidoglycan and arabinogalactan. Though most of the compounds exhibited little activity, however, one showed significant activity against all the strains in cell culture and activity was confirmed by BACTEC method. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(02)01398-3
• 作为产物：
  描述：

  ethyl (Z)-[3-O-methyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate 在 氨 作用下， 以 乙醇 为溶剂， 生成 ethyl 5-amino-5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-α-D-xylo-1,4-heptofuranuronate
  参考文献：
  名称：

  Synthesis and bioevaluation of glycosyl ureas as α-glucosidase inhibitors and their effect on mycobacterium

  摘要：

  Glycosyl amino esters (2-13) on reaction with different isocyanates resulted in quantitative conversion to glycosyl ureas (14-32). Few of the selected ureas (15-20, 22-28, 30 and 32) on cyclative amidation with DBU/TBAB/4 Angstrom MS gave respective dihydropyrimidinones in fair to good yields (33-47). The compounds were screened for alpha-glucosidase inhibitory activity and two (19 and 23) of them showed strong inhibition against rat intestinal (x-glucosidase. The compounds were also screened against Mycobacterium aurum, however, only one (19) of them exhibited marginal antitubercular activity. (C) 2000 Elsevier Science Ltd. All rights reserved. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00214-1

文献信息

• Synthesis and DNA Topoisomerase-II Inhibitory Activity of Unnatural Nucleosides
  作者：Ram Chandra Mishra、Namrata Dwivedi、Iti Bansal、Jitendra Kumar Saxena、Rama Pati Tripathi

  DOI：10.1081/ncn-200046776

  日期：2005.1.1

  The synthesis and biological activities Of a number of unnatural nucleosides (23 - 43) is described. Nucleosides have been synthesized by SnCl4-catalyzed condensation of amino sugar acetates and silylated modified pyrimidines. Few of the 2'-O-acetyl derivatives of the nucleosides were hydrolyzed to the respective hydroxy derivatives 0 treatment with methanol saturated with ammonia. The compounds were screened against Filarial DNA-topoisomerase-II but on one of the compounds (29) inhibited this enzyme at 40 mug/mL of reaction mixture.