| 58667-83-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 58667-83-7
• 化学式: C₁₁H₁₃N₃O₃S*C₄₂H₇₀O₃₅
• 分子量: 1402.31
• InChiKey: VAUBTCKAWAMLSB-ZQOBQRRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -13.56
• 重原子数：
  95.0
• 可旋转键数：
  10.0
• 环数：
  23.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  652.27
• 氢给体数：
  23.0
• 氢受体数：
  40.0

反应信息

• 作为产物：
  描述：

  磺胺异噁唑 、 β-环糊精 以 水 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Spectral Characteristics of Sulfa Drugs: Effect of Solvents, pH and β-Cyclodextrin

  摘要：

  分析了磺胺甲噁唑（SMO）、磺胺异噁唑（SFO）、磺胺噻唑（STO）和磺胺（SAM）在不同溶剂、pH 值和β-环糊精（β-CD）中的吸收光谱和荧光光谱。通过紫外可见光谱、荧光测定法、DFT、扫描电镜、傅立叶变换红外光谱和 1H NMR 对上述磺胺类药物与 β-CD 的包合物进行了研究。溶剂研究表明，SAM 分子（R-SO2-NH-基团）中取代基（噁唑或噻唑基团）的位置并不是改变这些磺胺药物分子吸收和发射行为的关键因素。在水溶液中观察到的是单一荧光带（340 nm），而在β-CD溶液中观察到的是α-药物化合物的双发射（430 nm）。在 SMO、SFO 和 STO 中形成的包合物应导致双发射，这是由于分子内电荷转移扭曲带（TICT）造成的。β-CD 研究表明：(i)  α-药物与 β-CD 形成 1:1 的包合复合物；(ii)  β-CD 介质中的红移和 TICT 的存在证实了杂环封装在 β-CD 空腔中，苯胺环存在于 β-CD 空腔的外侧。

  DOI：

  10.1007/s10953-010-9559-0

文献信息

• Spectral, thermal, and molecular modeling studies on the encapsulation of selected sulfonamide drugs in β-cyclodextrin nano-cavity
  作者：Abdulilah Dawoud Bani-Yaseen、Abeer Mo’ala

  DOI：10.1016/j.saa.2014.04.136

  日期：2014.10

  In the present work the inclusion complexation of three sulfonamide (SA) drugs, namely sulfisoxazole (SSX), sulfamethizole (SMZ), and Sulfamethazine (STM) with beta-cyclodextrin (beta-CD) has been investigated using UV-Vis spectroscopy, DSC, H-1 NMR spectroscopy, and molecular modeling methods. The binding constant (K-b) of SA:beta-CD inclusion complexation was determined via applying the modified form of Benesi-Hildebrand equation employing the changes in absorbance at lambda(max). Obtained results revealed that SA drugs form 1:1 inclusion complex with beta-CD with K-b of 650, 1532, 714 M-1 at 25 degrees C for SSX, SMZ, and STM, respectively. The UV-Vis absorption spectra displayed solvatochromic behavior of bathochromic shift with decreasing solvent polarity that in turn is good agreement with their behavior in the presence of beta-CD in terms of environment polarity dependency. The inclusion complex formation between beta-CD and tested SA drugs in liquid and solid states was confirmed by 1H NMR and DSC, respectively. Using semi-empirical quantum chemistry methods at PM3 theoretical level, inclusion complexes' structures as well as energetic and thermodynamic parameters of encapsulation were elucidated. Obtained results revealed that the encapsulation is favorably energetic and enthalpic in nature with the inclusion of the aniline moiety through the wide rim side of beta-CD nano-cavity. Further, molecular modeling revealed that beta-CD encapsulation of SA drugs reduced their (E-HOMO - E-LUMO) gap. (C) 2014 Elsevier B.V. All rights reserved.