5-(4-[2-(diethylamino)ethyl]carbamoylphenylazo)salicylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 5-(4-[2-(diethylamino)ethyl]carbamoylphenylazo)salicylic acid
• 英文别名: 5-[[4-[2-(Diethylamino)ethylcarbamoyl]phenyl]diazenyl]-2-hydroxybenzoic acid；5-[[4-[2-(diethylamino)ethylcarbamoyl]phenyl]diazenyl]-2-hydroxybenzoic acid
• 化学式: C₂₀H₂₄N₄O₄
• 分子量: 384.435
• InChiKey: DAWKRLAQDXDKPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  盐酸普鲁卡因胺 、 水杨酸 在 盐酸 、 氨基磺酸 、 sodium nitrite 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 8.0h， 以75%的产率得到5-(4-[2-(diethylamino)ethyl]carbamoylphenylazo)salicylic acid
  参考文献：
  名称：

  대장 표적성 염증성 장질환 예방 또는 치료용 조성물

  摘要：

  本发明涉及用于预防或治疗结肠靶向性炎症性肠疾病的组合物，更详细地说，提供了一种化合物，用化学式1表示，或其药学上可接受的盐，其中包括该化合物或其盐作为有效成分的用于预防或治疗炎症性肠疾病的药学组合物和保健食品组合物。根据本发明的化合物或其药学上可接受的盐是一种具有结肠靶向性的治疗组合物，仅在结肠内微生物的酶作用下才会被分解激活，可以在结肠中分别释放为5-氨基水杨酸和5-氨基尼科酸，并且可以相互补充作用，从而更有效地提高炎症性肠疾病的治疗效果。

  公开号：

  KR102141035B1

文献信息

• 대장 표적성 염증성 장질환 예방 또는 치료용 조성물
  申请人：Pusan National University Industry-University Cooperation Foundation 부산대학교 산학협력단(220040044843) BRN ▼621-82-06530

  公开号：KR102141035B1

  公开（公告）日：2020-08-06

  본 발명은 대장 표적성 염증성 장질환 예방 또는 치료용 조성물에 관한 것으로, 보다 상세하게는 화학식 1로 표시되는 화합물 또는 이의 약학적으로 허용가능한 염, 상기 화합물 또는 이의 염을 유효성분으로 포함하는 염증성 장질환 예방 또는 치료용 약학 조성물 및 건강기능식품 조성물을 제공한다. 본 발명에 따른 화합물 또는 이의 약학적으로 허용가능한 염은 대장에서 장내 미생물의 효소에 의해서만 분해되어 활성화되는 대장 표적성을 가진 치료 조성물로, 대장에서 5-아미노살리실산과 5-아미노니코틴산으로 각각 방출될 수 있고, 서로의 효능을 보완하여 염증성 장질환의 치료 효과를 보다 향상시킬 수 있다.

  本发明涉及用于预防或治疗结肠靶向性炎症性肠疾病的组合物，更详细地说，提供了一种化合物，用化学式1表示，或其药学上可接受的盐，其中包括该化合物或其盐作为有效成分的用于预防或治疗炎症性肠疾病的药学组合物和保健食品组合物。根据本发明的化合物或其药学上可接受的盐是一种具有结肠靶向性的治疗组合物，仅在结肠内微生物的酶作用下才会被分解激活，可以在结肠中分别释放为5-氨基水杨酸和5-氨基尼科酸，并且可以相互补充作用，从而更有效地提高炎症性肠疾病的治疗效果。
• 5-Aminosalicylic Acid Azo-Linked to Procainamide Acts as an Anticolitic Mutual Prodrug via Additive Inhibition of Nuclear Factor kappaB
  作者：Wooseong Kim、Joon Nam、Sunyoung Lee、Seongkeun Jeong、Yunjin Jung

  DOI：10.1021/acs.molpharmaceut.6b00294

  日期：2016.6.6

  To improve the anticolitic efficacy of 5-aminosalicylic acid (5-ASA), a colon-specific mutual prodrug of 5-ASA was designed. 5-ASA was coupled to procainamide (PA), a local anesthetic, via an azo bond to prepare 5-(4-[2-(diethylamino)ethyl]carbamoyl}phenylazo)salicylic acid (5-ASA-azo-PA). 5-ASA-azo-PA was cleaved to 5-ASA and PA up to about 76% at 10 h in the cecal contents while remaining stable in the small intestinal contents. Oral gavage of 5-ASA-azo-PA and sulfasalazine, a colon-specific prodrug currently used in clinic, to rats showed similar efficiency in delivery of 5-ASA to the large intestine, and PA was not detectable in the blood after 5-ASA-azo-PA administration. Oral gavage of 5-ASA-azo-PA alleviated 2,4,6-trinitrobenzenesulfonic acid-induced rat colitis. Moreover, combined intracolonic treatment with 5-ASA and PA elicited an additive ameliorative effect. Furthermore, combined treatment with 5-ASA and PA additively inhibited nuclear factor-kappaB (NF kappa B) activity in human colon carcinoma cells and inflamed colonic tissues. Finally, 5-ASA-azo-PA administered orally was able to reduce inflammatory mediators, NF kappa B target gene products, in the inflamed colon. 5-ASA-azo-PA may be a colon-specific mutual prodrug acting against colitis, and the mutual anticolitic effects occurred at least partly through the cooperative inhibition of NF kappa B activity.