3-(2-(6-methoxynaphthalen-2-yl)propanamido)propanoic acid | 1448460-41-0

• 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: 3-(2-(6-methoxynaphthalen-2-yl)propanamido)propanoic acid
• 英文别名: 3-[[(2S)-2-(6-methoxynaphthalen-2-yl)propanoyl]amino]propanoic acid
• CAS: 1448460-41-0
• 化学式: C₁₇H₁₉NO₄
• 分子量: 301.342
• InChiKey: QINBLFVYHRXQRC-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-(6-methoxynaphthalen-2-yl)propanamido)propanoic acid 在 氯化亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.17h， 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：

  萘普生 在 甲醇 、 4-吡咯烷基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 potassium hydroxide 作用下， 以 二氯甲烷 为溶剂， 生成 3-(2-(6-methoxynaphthalen-2-yl)propanamido)propanoic acid
  参考文献：
  名称：

  “Snorkelling” vs. “diving” in mixed micelles probed by means of a molecular bathymeter

  摘要：

  一种基于与信号荧光物质连接的羧酸的分子测深仪，在混合胶束中证明了“浮潜”与“潜水”的区别。

  DOI：

  10.1039/c7ob02595e

文献信息

• Designing a simple organic salt-based supramolecular topical gel capable of displaying in vivo self-delivery application
  作者：Joydeb Majumder、Jolly Deb、Mahua Rani Das、Siddhartha Sankar Jana、Parthasarathi Dastidar

  DOI：10.1039/c3cc48513g

  日期：——

  The supramolecular synthon approach has been exploited to design simple salt-based supramolecular gelators derived from a non-steroidal anti-inflammatory drug (NSAID) - naproxen; one such biocompatible anti-inflammatory gelator salt was converted into a topical gel that showed excellent in vivo self-delivery application in treating imiquimod (IMQ)-induced skin inflammation in mice.

  超分子合成子方法已被用来设计衍生自非甾体抗炎药（NSAID）-萘普生的简单的基于盐的超分子凝胶剂。一种这样的生物相容性抗炎胶凝盐被转化为局部用凝胶，该局部用凝胶在治疗咪喹莫特（IMQ）诱导的小鼠皮肤炎症中表现出出色的体内自我传递作用。
• Enhancement of the Anti-Inflammatory Activity of NSAIDs by Their Conjugation with 3,4,5-Trimethoxybenzyl Alcohol
  作者：Paraskevi Tziona、Panagiotis Theodosis-Nobelos、Georgios Papagiouvannis、Anthi Petrou、Chryssoula Drouza、Eleni A. Rekka

  DOI：10.3390/molecules27072104

  日期：——

  The synthesis of derivatives of three nonspecific COX-1 and COX-2 inhibitors, ibuprofen, ketoprofen, naproxen is presented. These acids were connected via an amide bond with an amino acid (L-proline, L-tyrosine, and beta-alanine) used as a linker. The amino acid carboxylic group was esterified with 3,4,5 trimethoxybenzyl alcohol. The activity of the novel derivatives was examined in vivo on carrageenan-induced

  介绍了三种非特异性 COX-1 和 COX-2 抑制剂布洛芬、酮洛芬、萘普生的衍生物的合成。这些酸通过酰胺键与用作接头的氨基酸（L-脯氨酸、L-酪氨酸和β-丙氨酸）连接。氨基酸羧基用 3,4,5 三甲氧基苄醇酯化。在体内检测了新衍生物对角叉菜胶诱导的炎症的活性，并在体外检测了作为环氧合酶和脂氧合酶抑制剂的活性。发现新化合物比母体药物更有效的抗炎剂。因此，布洛芬 ( 21 ) 和酮洛芬 ( 16) 衍生物减少了 67% 和 91% 的大鼠爪水肿（相关 NSAID 的减少分别为 36% 和 47%）。与起始药物相比，它们对 COX-2 的抑制作用更大（21种抑制67％，布洛芬 46％，19种抑制94％，酮洛芬 49％）。化合物与 COX-1 和 COX-2 活性位点的对接反映了它们的体外活性。因此，19采用了对 COX-1 抑制不利的方向，但它在 COX-2 的结合口袋中有效结合，这与 COX-1
• β-Amino Acid and Amino-Alcohol Conjugation of a Nonsteroidal Anti-Inflammatory Drug (NSAID) Imparts Hydrogelation Displaying Remarkable Biostability, Biocompatibility, and Anti-Inflammatory Properties
  作者：Joydeb Majumder、Mahua Rani Das、Jolly Deb、Siddhartha Sankar Jana、Parthasarathi Dastidar

  DOI：10.1021/la401929v

  日期：2013.8.13

  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).
• “Snorkelling” <i>vs.</i> “diving” in mixed micelles probed by means of a molecular bathymeter
  作者：Gemma M. Rodriguez-Muñiz、Miguel Gomez-Mendoza、Edurne Nuin、Inmaculada Andreu、M. Luisa Marin、Miguel A. Miranda

  DOI：10.1039/c7ob02595e

  日期：——

  A molecular bathymeter based on a carboxylic acid linked to a signalling fluorophore proves “snorkelling” vs. “diving” in mixed micelles.

  一种基于与信号荧光物质连接的羧酸的分子测深仪，在混合胶束中证明了“浮潜”与“潜水”的区别。