mono-6-deoxy-6-carboxy-β-cyclodextrin | 769884-11-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: mono-6-deoxy-6-carboxy-β-cyclodextrin
• 英文别名: 6-Deoxy-6-carboxy-β-cyclodextrin；(1S,3R,5R,6S,8S,10S,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-5,15,20,25,30,35-hexakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontane-10-carboxylic acid
• CAS: 769884-11-9
• 化学式: C₄₂H₆₈O₃₆
• 分子量: 1148.98
• InChiKey: NZJNPEQFQVIIBD-RSGLQJMASA-N

物化性质

• 沸点：
  1577.1±65.0 °C(Predicted)
• 密度：
  1.659±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -14.8
• 重原子数：
  78
• 可旋转键数：
  7
• 环数：
  21.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  571
• 氢给体数：
  21
• 氢受体数：
  36

反应信息

• 作为反应物：
  描述：

  缩宫素 、 mono-6-deoxy-6-carboxy-β-cyclodextrin 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 以30%的产率得到
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of a new targeted drug carrier system: β-Cyclodextrin coupled to oxytocin

  摘要：

  beta-Cyclodextrin (beta-CD) was monofunctionalized into its carboxylic derivative and then conjugated to the N-side of oxytocin (OT), a nonapeptide involved in human behavior and myometrium contraction. On isolated rat myometrium, this conjugate (beta-CD-OT) partly preserves the contracting activity of OT (EC50 = 0.40 mu M vs 1.7 nM). Moreover, the contraction induced frequency is also lowered by beta-CD-OT. This novel hydrophilic targeted carrier could form a host-guest complex with prostaglandins and their derivatives used as labor inducers or with anticancer drugs used in cervix and endometrial cancer. This strategy can improve the solubility, the stability, and/or the biological activity of these drugs as well as reducing their side-effects. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.02.017
• 作为产物：
  描述：

  β-cyclodextrin monoaldehyde 在 phosphate buffer 、 溴 作用下， 反应 120.0h， 以20%的产率得到mono-6-deoxy-6-carboxy-β-cyclodextrin
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of a new targeted drug carrier system: β-Cyclodextrin coupled to oxytocin

  摘要：

  beta-Cyclodextrin (beta-CD) was monofunctionalized into its carboxylic derivative and then conjugated to the N-side of oxytocin (OT), a nonapeptide involved in human behavior and myometrium contraction. On isolated rat myometrium, this conjugate (beta-CD-OT) partly preserves the contracting activity of OT (EC50 = 0.40 mu M vs 1.7 nM). Moreover, the contraction induced frequency is also lowered by beta-CD-OT. This novel hydrophilic targeted carrier could form a host-guest complex with prostaglandins and their derivatives used as labor inducers or with anticancer drugs used in cervix and endometrial cancer. This strategy can improve the solubility, the stability, and/or the biological activity of these drugs as well as reducing their side-effects. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.02.017

文献信息

• Selective oxidation of primary alcohol groups of β-cyclodextrin mediated by 2,2,6,6-tetramethylpiperidine-1-oxyl radical (TEMPO)
  作者：Carole Fraschini、Michel R. Vignon

  DOI：10.1016/s0008-6215(00)00129-4

  日期：2000.10

  Beta-cyclodextrin (beta-CD) was reacted with catalytic amounts of 2,2,6,6-tetramethylpiperidine-1-oxyl radical (TEMPO), sodium hypochlorite and sodium bromide at 2 degrees C and a pH value of 10 in water. The primary alcohol groups were selectively oxidized into carboxylate groups within a few minutes, and mono- and dicarboxy-beta-cyclodextrin sodium salts were isolated and characterized by 1H, 13C

  在2摄氏度和pH值为10的水中，将β-环糊精（β-CD）与催化量的2,2,6,6-四甲基哌啶-1-氧基（TEMPO），次氯酸钠和溴化钠反应。在几分钟内将伯醇基团选择性地氧化成羧酸根基团，并分离出单羧基和二羧基-β-环糊精钠盐，并通过1H，13C NMR和质谱进行了表征。通过该反应系统，环氧化糊精的降解受到限制，条件是该氧化反应需在2摄氏度，恒定pH值为10的条件下进行，并使用催化量的TEMPO和受控量的次氯酸钠和溴化钠进行连续再生。氧铵盐。
• A General Method for the Synthesis of Cyclodextrinyl Aldehydes and Carboxylic Acids
  作者：Juyoung Yoon、Sungyeap Hong、Kristy A. Martin、Anthony W. Czarnik

  DOI：10.1021/jo00114a030

  日期：1995.5

  The selective synthesis of the primary-side monoaldehyde of beta-cyclodextrin, 6-deoxy-6-formyl-beta-cyclodextrin, was accomplished by oxidation of the corresponding tosylate utilizing the Nace reaction (DMSO/collidine). This monoaldehyde was then used as the starting material in several reactions including reduction, addition of NaHSO3, addition of the alpha-nucleophiles hydroxylamine and hydrazine, and reductive amination. Of particular interest is the conversion of the monoaldehyde to the primary side carboxylic acid, 6-deoxy-6-carboxy-beta-cyclodextrin, via bromine oxidation. This general method sequence can be applied to any tosyl derivative of cyclodextrin as demonstrated in the synthesis of beta-cyclodextrin-A,D-dialdehyde and beta-cyclodextrin-A,D-diacid.
• Synthesis and pharmacological evaluation of a new targeted drug carrier system: β-Cyclodextrin coupled to oxytocin
  作者：Carine Bertolla、Stéphanie Rolin、Brigitte Evrard、Lionel Pochet、Bernard Masereel

  DOI：10.1016/j.bmcl.2008.02.017

  日期：2008.3

  beta-Cyclodextrin (beta-CD) was monofunctionalized into its carboxylic derivative and then conjugated to the N-side of oxytocin (OT), a nonapeptide involved in human behavior and myometrium contraction. On isolated rat myometrium, this conjugate (beta-CD-OT) partly preserves the contracting activity of OT (EC50 = 0.40 mu M vs 1.7 nM). Moreover, the contraction induced frequency is also lowered by beta-CD-OT. This novel hydrophilic targeted carrier could form a host-guest complex with prostaglandins and their derivatives used as labor inducers or with anticancer drugs used in cervix and endometrial cancer. This strategy can improve the solubility, the stability, and/or the biological activity of these drugs as well as reducing their side-effects. (C) 2008 Elsevier Ltd. All rights reserved.