1-{[1''-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-1''H-1'',2'',3''-triazol-4''-yl]methyl}-indoline-2,3-dione | 1427040-73-0

• 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: 1-{[1''-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-1''H-1'',2'',3''-triazol-4''-yl]methyl}-indoline-2,3-dione
• 英文别名: 1-[{1′-(2′′,3′′,4′′,6′′-tetra-O-acetyl-β-D-glucopyranosyl)-1′H-1′,2′,3′-triazol-4′-yl} methyl]indoline-2,3-dione；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[4-[(2,3-dioxoindol-1-yl)methyl]triazol-1-yl]oxan-2-yl]methyl acetate
• CAS: 1427040-73-0
• 化学式: C₂₅H₂₆N₄O₁₁
• 分子量: 558.502
• InChiKey: HPCYSJGRWHHEBZ-FGBFUVBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  183
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  1-{[1''-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-1''H-1'',2'',3''-triazol-4''-yl]methyl}-indoline-2,3-dione 在 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 1.5h， 生成 (Z)-3-{2-(4-bromophenyl)hydrazono}-1-[{1′-(β-D-glucopyranosyl)-1′H-1′,2′,3′-triazol-4′-yl}methyl]indoline-2,3-dione
  参考文献：
  名称：

  Synthesis and antiplasmodial activity of glyco-conjugate hybrids of phenylhydrazono-indolinones and glycosylated 1,2,3-triazolyl-methyl-indoline-2,3-diones

  摘要：

  A small library of 36 new glycohybrids of phenylhydrazono-indolinones was synthesized employing glycosylated 1,2,3-triazolyl-methyl-indoline-2,3-diones and different phenylhydrazines via acid catalyzed reaction. All the compounds were screened for their antiplasmodial activity in vitro. Compounds 6c, 7c, and 7b showed significant activity with the IC50 values 1.27,1.64 and 1.96 mu M, respectively against CQ sensitive Pf3D7 strain while compounds 7b and 6f showed good activity with IC50 1.61 and 1.93 mu M, respectively against CQ resistant PfK1 strain. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.06.042
• 作为产物：
  描述：

  2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 氘代二甲亚砜 、 二甲基亚砜 为溶剂， 反应 4.5h， 生成 1-{[1''-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-1''H-1'',2'',3''-triazol-4''-yl]methyl}-indoline-2,3-dione
  参考文献：
  名称：

  Synthesis of Novel Glycoconjugates Derived From Alkynyl Heterocycles through a Click Approach

  摘要：

  The synthesis of a series of novel 1,4-disubstituted 1,2,3-triazole compounds bearing a D-glucose derivative and an heteroaromatic system is described. Alkylation of isatin, 3-methyl-carbazole, and one tetrahydro--carboline with propargyl bromide gave their N-propargyl derivatives in good yields. These compounds further reacted with acetylated D-glucose with the azide group in position 1 to give three final products and with peracetylated 6-azido-6-deoxy--D-methylglucoside, giving the corresponding derivative of tetrahydro--carboline. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2011.637655