6-Hydroxy-β-naphthoic acid N-hydroxysuccinimide ester | 131450-61-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-Hydroxy-β-naphthoic acid N-hydroxysuccinimide ester
• 英文别名: (2,5-Dioxopyrrolidin-1-yl) 6-hydroxynaphthalene-2-carboxylate
• CAS: 131450-61-8
• 化学式: C₁₅H₁₁NO₅
• 分子量: 285.256
• InChiKey: GRCGJNGJQBSSJB-UHFFFAOYSA-N

物化性质

• 沸点：
  500.7±42.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-Hydroxy-β-naphthoic acid N-hydroxysuccinimide ester 在 N-甲基吗啉 、 吡啶 、 pyridinium acetyl sulfate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 (3S)-4-[[(2S)-1-amino-1-oxo-3-phenylpropan-2-yl]amino]-3-[[(2S)-2-[[(2S)-3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-6-[(6-sulfooxynaphthalene-2-carbonyl)amino]hexanoyl]amino]-4-oxobutanoic acid
  参考文献：
  名称：

  Development of potent and selective CCK-A receptor agonists from Boc-CCK-4: tetrapeptides containing Lys(N.epsilon.)-amide residues

  摘要：

  A series of Boc-CCK-4 derivatives represented by the general structure Boc-Trp-Lys(N(epsilon)-COR)-Asp-Phe-NH2, where R is an aromatic, heterocyclic, or aliphatic group, are potent and selective CCK-AT receptor agonists. These amide-bearing compounds complement the previously described urea-based tetrapeptides (Shiosaki et al. J. Med. Chem. 1991, 34, 2837-2842); structure-activity studies revealed parallel as well as divergent trends between these two series. A significant correlation was observed between pancreatic binding affinity and the resonance constant R of the phenyl substituent in one particular series of derivatives. Sulfation of phenolic amides appended onto the epsilon-amino group of the lysine did not affect affinity for the CCK-AT receptor in contrast to the 500-fold increase in binding potency observed upon sulfation of CCK-8, suggesting that the lysine appendage and the sulfated tyrosine in CCK-8, both key structural elements that impart high affinity for the CCK-A receptor, are interacting differently with the receptor. The amide-bearing tetrapeptides are full agonists relative to CCK-8 in stimulating pancreatic amylase release while being partial agonists in eliciting phosphoinositide (PI) hydrolysis. Both effects were blocked by selective CCK-A receptor antagonists.

  DOI：

  10.1021/jm00089a010
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 2-羟基-6-萘甲酸 以 二氯甲烷 为溶剂， 生成 6-Hydroxy-β-naphthoic acid N-hydroxysuccinimide ester
  参考文献：
  名称：

  Derivatives of tetrapeptides as CCK agonists

  摘要：

  公式（I）的选择性和有效的Type-A CCK受体激动剂为：X--Y--Z--Q（I）或其药学上可接受的盐，其中，X选自##STR1##，Y选自##STR2##，Z为##STR3##，Q为##STR4##或其药学上可接受的盐，可用于治疗胃肠道疾病（包括胆囊疾病）、中枢神经系统疾病、胰岛素相关疾病和疼痛，以及食欲调节。

  公开号：

  US05270302A1

文献信息

• Amphiphilic aminoglycosides with increased selectivity for inhibition of connexin 43 (Cx43) hemichannels
  作者：Yagya P. Subedi、Abbey Kjellgren、Paul Roberts、Heath Montgomery、Noah Thackeray、Mariana C. Fiori、Guillermo A. Altenberg、Cheng-Wei T. Chang

  DOI：10.1016/j.ejmech.2020.112602

  日期：2020.10

  Gap junction channels formed by the association of connexin hemichannels play a crucial role in intercellular communication. Connexin 43 (Cx43) is expressed in a variety of tissues and organs, including heart and brain, and abnormal sustained opening of undocked "free" hemichannels contributes to the cell damage in cardiac infarcts and stroke. Selective inhibitors of Cx43 hemichannels for clinical use are then desirable. Here, we synthesized and tested new aminoglycosides for their connexin inhibitory activity towards Cx26 and Cx43 hemichannels. The lead compounds displayed enhanced Cx43/Cx26 selectivity for hemichannel inhibition when compared to the parent kanamycin A and other commercially available aminoglycosides. These lead compounds are not cytotoxic to mammalian cells and show promise for the treatment of ischemic damage of the heart, brain, and kidneys. We identified a new compound as a promising lead based on its good selectivity for Cx43 hemichannels inhibition and the simplicity and affordability of its production. (C) 2020 Elsevier Masson SAS. All rights reserved.
• EP0449884A4
  申请人：——

  公开号：EP0449884A4

  公开（公告）日：1991-10-30
• DERIVATIVES OF TETRAPEPTIDES AS CCK AGONISTS
  申请人：ABBOTT LABORATORIES

  公开号：EP0449884A1

  公开（公告）日：1991-10-09
• US5270302A
  申请人：——

  公开号：US5270302A

  公开（公告）日：1993-12-14
• [EN] DERIVATIVES OF TETRAPEPTIDES AS CCK AGONISTS
  申请人：ABBOTT LABORATORIES

  公开号：WO1990006937A1

  公开（公告）日：1990-06-28

  (EN) Tetrapeptide analogs are disclosed which possess CCK agonist activity.(FR) Les analogues de tétrapeptides décrits possèdent une activité similaire à la cholécystokinine (CCK).