6-(2-aminoethylamino)-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose | 125008-73-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 6-(2-aminoethylamino)-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
• 英文别名: 6-deoxy-6-[N-(2‘-aminoethylamino)-1,2:3,4-di-O-isopropylidene]-α-D-galactopyranose；N'-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methyl]ethane-1,2-diamine
• CAS: 125008-73-3
• 化学式: C₁₄H₂₆N₂O₅
• 分子量: 302.371
• InChiKey: LPARVKAAFVQQDN-YBXAARCKSA-N

物化性质

• 沸点：
  397.2±37.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  84.2
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-(2-aminoethylamino)-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 、 棕榈酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以72%的产率得到6-[N-hexadecanoyl-N-(2-(hexadecanoylamino)ethyl)amino]-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
  参考文献：
  名称：

  Synthesis of amphiphilic galactopyranosyl diamines and amino alcohols as antitubercular agents

  摘要：

  Mono-and diacylated derivatives of galactopyranosyl amines were obtained from D-galactose, via aminated intermediates prepared by reaction of 6-deoxy-6-iodo-1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose with 1,3-propanediamine, 1,2-ethanediamine or ethanolamine. Monoacylated derivatives displayed antitubercular activity. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.01.009
• 作为产物：
  描述：

  alpha-D-半乳糖 在 咪唑 、 硫酸 、 碘 、 三苯基膦 、 zinc(II) chloride 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 24.0h， 生成 6-(2-aminoethylamino)-6-deoxy-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
  参考文献：
  名称：

  含有衍生自碳水化合物的配体的新型金（I）和金（III）配合物的合成，表征，细胞毒性和抗结核活性。

  摘要：

  合成了含有D-半乳糖，D-核糖和D-葡萄糖基-1,5-内酯衍生物的新型金（I）和金（III）配合物，并通过IR，（1）H和（13）C进行了表征NMR，高分辨率质谱和循环伏安法。体外评估了这些化合物对三种类型的肿瘤细胞的细胞毒性：宫颈癌（HeLa）乳腺腺癌（MCF-7）和胶质母细胞瘤（MO59J），以及一种非肿瘤细胞系：人肺成纤维细胞（GM07492A）。评估它们的抗结核活性，并以μg/ mL的最低抑菌浓度（MIC90）表示。通常，金（I）配合物比金（III）配合物更具活性，例如，金（I）配合物（1）的毒性是金（III）配合物（8）的约8.8倍和细胞毒性的7.6倍。 MO59J和MCF-7电池。核糖和烷基膦衍生物的配合物比半乳糖和芳基膦的配合物更具活性。噻唑烷环的存在不能改善细胞毒性。细胞毒性活性的研究表明，金（I）复合物具有有效的抗肿瘤活性，在所有测试的肿瘤细胞系中比顺铂更具活性。即使与一

  DOI：

  10.1007/s10534-015-9870-8

文献信息

• Synthesis and antitubercular evaluation of new fluoroquinolone derivatives coupled with carbohydrates
  作者：Maurício F. Saraiva、Marcus V.N. de Souza、Marie E. Tran Huu Dau、Débora P. Araújo、Gustavo S.G. de Carvalho、Mauro V. de Almeida

  DOI：10.1016/j.carres.2010.01.016

  日期：2010.4

  We describe in this work the synthesis of nine new fluoroquinolone derivatives based on modifications at the C-7 position of the known fluoroquinolones cipro-, gati-, and moxifloxacin, as well as their antitubercular evaluation. The synthesis of these new analogues was improved using microwave irradiation, providing several advantages such as better yields and shorter reaction times, in comparison with classical reaction conditions. Derivatives 4, 5, and 7 exhibited promising antitubercular activities. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of Platinum Complexes from Sugar Derivatives
  作者：Mauro Vieira De Almeida、Eloi Teixeira Cesar、Ana Paula Soares Fontes、Emanoel de Castro Antunes Felício

  DOI：10.1080/07328300008544081

  日期：2000.1

  Six new platinum(II) complexes containing a diamino sugar, analogs of cisplatin and carboplatin, have been prepared and characterized. The new ligands were obtained by reaction of D-galactose and D-ribose derivatives with ethylenediamine.
• Synthesis, characterization, cytotoxic and antitubercular activities of new gold(I) and gold(III) complexes containing ligands derived from carbohydrates
  作者：Joana Darc Souza Chaves、Jaqueline Lopes Damasceno、Marcela Cristina Ferreira Paula、Pollyanna Francielli de Oliveira、Gustavo Chevitarese Azevedo、Renato Camargo Matos、Maria Cristina S. Lourenço、Denise Crispim Tavares、Heveline Silva、Ana Paula Soares Fontes、Mauro Vieira de Almeida

  DOI：10.1007/s10534-015-9870-8

  日期：2015.10

  μg/mL. In general, the gold(I) complexes were more active than gold(III) complexes, for example, the gold(I) complex (1) was about 8.8 times and 7.6 times more cytotoxic than gold(III) complex (8) in MO59J and MCF-7 cells, respectively. Ribose and alkyl phosphine derivative complexes were more active than galactose and aryl phosphine complexes. The presence of a thiazolidine ring did not improve the cytotoxicity

  合成了含有D-半乳糖，D-核糖和D-葡萄糖基-1,5-内酯衍生物的新型金（I）和金（III）配合物，并通过IR，（1）H和（13）C进行了表征NMR，高分辨率质谱和循环伏安法。体外评估了这些化合物对三种类型的肿瘤细胞的细胞毒性：宫颈癌（HeLa）乳腺腺癌（MCF-7）和胶质母细胞瘤（MO59J），以及一种非肿瘤细胞系：人肺成纤维细胞（GM07492A）。评估它们的抗结核活性，并以μg/ mL的最低抑菌浓度（MIC90）表示。通常，金（I）配合物比金（III）配合物更具活性，例如，金（I）配合物（1）的毒性是金（III）配合物（8）的约8.8倍和细胞毒性的7.6倍。 MO59J和MCF-7电池。核糖和烷基膦衍生物的配合物比半乳糖和芳基膦的配合物更具活性。噻唑烷环的存在不能改善细胞毒性。细胞毒性活性的研究表明，金（I）复合物具有有效的抗肿瘤活性，在所有测试的肿瘤细胞系中比顺铂更具活性。即使与一
• Synthesis of amphiphilic galactopyranosyl diamines and amino alcohols as antitubercular agents
  作者：Mauro Vieira de Almeida、Mireille Le Hyaric、Giovanni Wilson Amarante、Maria Cristina Silva Lourenço、Marcelo Luiz Lima Brandão

  DOI：10.1016/j.ejmech.2007.01.009

  日期：2007.8

  Mono-and diacylated derivatives of galactopyranosyl amines were obtained from D-galactose, via aminated intermediates prepared by reaction of 6-deoxy-6-iodo-1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose with 1,3-propanediamine, 1,2-ethanediamine or ethanolamine. Monoacylated derivatives displayed antitubercular activity. (c) 2007 Elsevier Masson SAS. All rights reserved.