naproxen benzotriazolide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: naproxen benzotriazolide
• 英文别名: (S)-1-(1H-benzo[d][1,2,3]triazol-1-yl)-2-(6-methoxynaphthalen-2-yl)propan-1-one；naproxen-Bt；1-benzotriazol-1-yl-2-(6-methoxy-naphthalen-2-yl)-propan-1-one；(2S)-1-(benzotriazol-1-yl)-2-(6-methoxynaphthalen-2-yl)propan-1-one
• 化学式: C₂₀H₁₇N₃O₂
• 分子量: 331.374
• InChiKey: RIOUGVXXDKNHHT-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  naproxen benzotriazolide 在 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 48.17h， 生成 (2S)-N-[3-[[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]amino]-3-oxopropyl]-2-(6-methoxynaphthalen-2-yl)propanamide
  参考文献：
  名称：

  β-Amino Acid and Amino-Alcohol Conjugation of a Nonsteroidal Anti-Inflammatory Drug (NSAID) Imparts Hydrogelation Displaying Remarkable Biostability, Biocompatibility, and Anti-Inflammatory Properties

  摘要：

  A well-known nonsteroidal anti-inflammatory drug (NSAID), namely, naproxen (Np), was conjugated with beta-alanine and various combinations of amino alcohols and L-alanine. Quite a few bioconjugates, thus synthesized, were capable of gelling pure water, NaCl solution (0.9 wt %), and phosphate-buffered saline (PBS) (pH 7.4). The hydrogels were characterized by rheology and electron microscopy. Hydrogelation was probed by FT-IR and temperature-variable H-1 NMR studies. Single-crystal X-ray diffraction (SXRD) of a nonhydrogelator and a hydrogelator in the series established a useful structure-property (gelation) correlation. MTT assay of the hydrogelators in the mouse macrophage RAW 264.7 cell line showed excellent biocompatibility. The prostaglandin E-2 (PGE(2)) assay of the hydrogelators revealed their anti-inflammatory response, which was comparable to that of the parent NSAID naproxen sodium (Ns).

  DOI：

  10.1021/la401929v
• 作为产物：
  描述：

  T406石油添加剂 、 萘普生 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 12.17h， 以85%的产率得到naproxen benzotriazolide
  参考文献：
  名称：

  β-Amino Acid and Amino-Alcohol Conjugation of a Nonsteroidal Anti-Inflammatory Drug (NSAID) Imparts Hydrogelation Displaying Remarkable Biostability, Biocompatibility, and Anti-Inflammatory Properties

  摘要：

  A well-known nonsteroidal anti-inflammatory drug (NSAID), namely, naproxen (Np), was conjugated with beta-alanine and various combinations of amino alcohols and L-alanine. Quite a few bioconjugates, thus synthesized, were capable of gelling pure water, NaCl solution (0.9 wt %), and phosphate-buffered saline (PBS) (pH 7.4). The hydrogels were characterized by rheology and electron microscopy. Hydrogelation was probed by FT-IR and temperature-variable H-1 NMR studies. Single-crystal X-ray diffraction (SXRD) of a nonhydrogelator and a hydrogelator in the series established a useful structure-property (gelation) correlation. MTT assay of the hydrogelators in the mouse macrophage RAW 264.7 cell line showed excellent biocompatibility. The prostaglandin E-2 (PGE(2)) assay of the hydrogelators revealed their anti-inflammatory response, which was comparable to that of the parent NSAID naproxen sodium (Ns).

  DOI：

  10.1021/la401929v

文献信息

• Microwave assisted synthesis and QSAR study of novel NSAID acetaminophen conjugates with amino acid linkers
  作者：Anand D. Tiwari、Siva S. Panda、Adel S. Girgis、Sandhyamayee Sahu、Riham F. George、Aladdin M. Srour、Brian La Starza、Abdullah M. Asiri、C. Dennis Hall、Alan R. Katritzky

  DOI：10.1039/c4ob01281j

  日期：——

  Novel, non-steroidal anti-inflammatory drug (NSAID), acetaminophen conjugates 6a–l with amino acid linkers were synthesized utilizing benzotriazole chemistry. Biological data acquired for all the novel bis-conjugates showed (a) some bis-conjugates (6d, 6e, 6h, and 6k) exhibit more potent anti-inflammatory activity than their parent drugs, (b) the potent bis-conjugates show no visible stomach lesions

  新型非甾体抗炎药（NSAID），具有氨基酸连接基的对乙酰氨基酚共轭物6a-1，是利用苯并三唑化学方法合成的。获得的所有新型双结合物的生物学数据表明（a）一些双结合物（6d，6e，6h和6k）比其母体药物显示出更强的抗炎活性，（b）强大的双结合物没有显示出与高度致溃疡的母体药物相比，可见的胃部病变明显；（c）有效的生物活性化合物在应用抗炎剂量的5倍时没有死亡率或毒性症状。具有统计学意义的QSAR模型，描述了6a–l的抗炎特性（使用验证所观察到的生物活性的CODESSA-Pro获得N＝ 15，n＝ 3，R 2＝ 0.891，R 2 cvOO ＝ 0.770，R 2 cvMO ＝ 0.796，F＝ 29.904，s 2＝ 0.011）。
• Efficient and Selective Syntheses of S-Acyl and N-Acyl Glutathiones
  作者：Alan Katritzky、Nader Abo- Dya、Srinivasa Tala、Ebrahim Ghazvini-Zadeh、Kiran Bajaj、Said El-Feky

  DOI：10.1055/s-0029-1219837

  日期：2010.6

  Selective syntheses of S-acyl glutathiones are achieved in 79-98% yields using 1-acyl-1H-benzotriazoles in the presence of potassium bicarbonate in aqueous methanol at 20 ˚C. N-Acylation of S-(p-nitrobenzoyl) glutathione with 1-acyl-1H-benzotriazoles followed by deprotection of the p-nitrobenzoyl groups under mild conditions gave 63-78% yields of N-acyl glutathiones. These methodologies should be useful for the S-acylation and N-acylation of peptides and glycopeptides.

  在 20 ËC 的甲醇水溶液中，在碳酸氢钾存在下，使用 1-酰基-1H-苯并三唑选择性合成 S-酰基谷胱甘肽，产率为 79-98%。用 1-酰基-1H-苯并三唑对 S-（对硝基苯甲酰基）谷胱甘肽进行 N-酰化，然后在温和的条件下对对硝基苯甲酰基进行脱保护，可得到产率为 63-78% 的 N-酰基谷胱甘肽。这些方法可用于肽和糖肽的 S-酰化和 N-酰化。
• NSAID Conjugates with Carnosine and Amino Acids
  作者：Alan Katritzky、Sandhyamayee Sahu、Siva Panda、Abdullah Asiri

  DOI：10.1055/s-0033-1339920

  日期：——

  Benzotriazole-mediated syntheses of novel bioconjugates of nonsteroidal anti-inflammatory drugs with carnosine and with amino acids were prepared in yields of 50-97% as potential drug candidates.