ethyl [5,6-dideoxy-5-hexadecylamino-3-O-methyl-1,2-O-isopropylidene-β-L-ido-heptofuran]uronate | 500908-27-0

• 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 [5,6-dideoxy-5-hexadecylamino-3-O-methyl-1,2-O-isopropylidene-β-L-ido-heptofuran]uronate
• 英文别名: ethyl (3S)-3-[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-3-(hexadecylamino)propanoate
• CAS: 500908-27-0
• 化学式: C₂₉H₅₅NO₆
• 分子量: 513.759
• InChiKey: FUHJOJKBYCWYOV-OBWVVCRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  36
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl [5,6-dideoxy-5-hexadecylamino-3-O-methyl-1,2-O-isopropylidene-β-L-ido-heptofuran]uronate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以92%的产率得到5,6-dideoxy-5-hexadecylamino-6-hydroxymethyl-1,2-O-isopropylidene-3-O-methyl-β-L-idofuranose
  参考文献：
  名称：

  糖基化氨基醇和胺的合成及其抗分枝杆菌活性。

  摘要：

  用氢化铝锂还原糖基β-氨基酯（6-14和25-30）可得到高收率的糖基氨基醇（15-23和31-36）。但是，在硼氢化钠的存在下，用不同的胺对糖基醛（1-3）进行还原胺化会导致糖基胺（37-41）的收率达到中度至中度。评价所有化合物对结核分枝杆菌H37Ra和H37Rv的抗结核活性。化合物18、21、35和36表现出抗结核活性，MIC为6.25至3.12 microg ml（-1）。

  DOI：

  10.1016/j.ejmech.2004.12.002
• 作为产物：
  描述：

  十六胺 、 ethyl [3-O-methyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate 以 乙醇 为溶剂， 以65%的产率得到ethyl [5,6-dideoxy-5-hexadecylamino-3-O-methyl-1,2-O-isopropylidene-β-L-ido-heptofuran]uronate
  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

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.
• Synthesis of glycosylated β-Amino hydroxamates as new class of antimalarials
  作者：R.C. Mishra、Renu Tripathi、Diksha Katiyar、Neetu Tewari、Deepti Singh、R.P. Tripathi

  DOI：10.1016/j.bmc.2003.09.038

  日期：2003.12

  Glycosylated beta-amino acids (3-18, 38, 39), obtained by hydrolysis of glycosylated beta-amino esters on reaction with hydroxylamine hydrochloride in presence of DIC/DCC afforded glycosyl beta-amino hydroxamates (19-34, 40, 41) in fair to good yields. Compounds (19-34, 40, 41) were screened against human malarial parasite Plasmodium falciparum in vitro for their schizontocidal activity. Compounds (19, 24, 26, 28, 40 and 41) exhibited good activity at 2 mug/mL concentrations. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis of glycosylated β-amino acids as new class of antitubercular agents
  作者：R.P. Tripathi、R. Tripathi、V.K. Tiwari、Laxmi Bala、S Sinha、A. Srivastava、R. Srivastava、B.S. Srivastava

  DOI：10.1016/s0223-5234(02)01398-3

  日期：2002.9

  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.
• Synthesis and antimycobacterial activities of glycosylated amino alcohols and amines
  作者：D. Katiyar、V.K. Tiwari、N. Tewari、S.S. Verma、S. Sinha、A. Gaikwad、A. Srivastava、V. Chaturvedi、R. Srivastava、B.S. Srivastava、R.P. Tripathi

  DOI：10.1016/j.ejmech.2004.12.002

  日期：2005.4

  Reduction of glycosyl beta-amino esters (6-14 and 25-30) with lithium aluminum hydride resulted in glycosyl amino alcohols (15-23 and 31-36) in good yields. However, reductive amination of glycosyl aldehydes (1-3) with different amines in presence of sodium borohydride resulted in good to moderate yields of glycosyl amines (37-41). All the compounds were evaluated for antitubercular activity against

  用氢化铝锂还原糖基β-氨基酯（6-14和25-30）可得到高收率的糖基氨基醇（15-23和31-36）。但是，在硼氢化钠的存在下，用不同的胺对糖基醛（1-3）进行还原胺化会导致糖基胺（37-41）的收率达到中度至中度。评价所有化合物对结核分枝杆菌H37Ra和H37Rv的抗结核活性。化合物18、21、35和36表现出抗结核活性，MIC为6.25至3.12 microg ml（-1）。