1-[3-[N-(5-溴吡啶-2-基)-N-(3,4-二氯苄基)氨基]丙基]-3-[3-(1H-咪唑-4-基)丙基]硫脲 | 199522-35-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-[3-[N-(5-溴吡啶-2-基)-N-(3,4-二氯苄基)氨基]丙基]-3-[3-(1H-咪唑-4-基)丙基]硫脲
• 中文别名: 1-[3-[N-(5-溴吡啶-2-基)-N-(3,4-二氯苯基)氨基]丙基]-3-[3-(1氢-咪唑-4-基)丙基]硫脲
• 英文名称: NNC 26-9100
• 英文别名: NNC26-9100；NNC-26-9100；1-(3-(N-(5-bromopyridin-2-yl)-N-(3,4-dichlorobenzyl)amino)propyl)-3-(3-(1H-imidazol-4-yl)propyl)thiourea；1-[3-[(5-bromo-2-pyridinyl)-[(3,4-dichlorophenyl)methyl]amino]propyl]-3-[3-(1H-imidazol-5-yl)propyl]thiourea；1-[3-[(5-bromopyridin-2-yl)-[(3,4-dichlorophenyl)methyl]amino]propyl]-3-[3-(1H-imidazol-5-yl)propyl]thiourea
• CAS: 199522-35-5
• 化学式: C₂₂H₂₅BrCl₂N₆S
• 分子量: 556.357
• InChiKey: UREJDUPKGMFJRU-UHFFFAOYSA-N

物化性质

• 溶解度：
  在 DMSO 中溶解度为 50 mM，在乙醇中溶解度为 50 mM

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  4

制备方法与用途

NNC 26-9100 是一种选择性的生长抑素sst4受体完全激动剂（Ki: 6 nM，EC50：2 nM）。它能够降低总可溶性Aβ42水平，增加脑啡肽酶活性，并改善学习能力。

反应信息

• 作为产物：
  描述：

  2,5-二溴吡啶 在 吡啶 、 盐酸 、 sodium hydride 、 二甲基亚砜 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 78.0h， 生成 1-[3-[N-(5-溴吡啶-2-基)-N-(3,4-二氯苄基)氨基]丙基]-3-[3-(1H-咪唑-4-基)丙基]硫脲
  参考文献：
  名称：

  Discovery of a Novel Non-Peptide Somatostatin Agonist with SST₄ Selectivity

  摘要：

  The discovery of novel non-peptide compounds with a high affinity for the peptide hormone somatostatin (SST) receptor is described. The compounds were tested for affinity at five human SST receptor subtypes individually expressed in mammalian cells. The compound NNC 26-9100 showed a K-i of 6 nM at SST4 and more than 100 fold selectivity for SST4 over SST1, SST2, SST3, or SST5. Competition binding studies and Scatchard analysis of the interaction by NNC 26-9100 with SST showed specificity at SST4. Furthermore, NNC 26-9100 was highly selective for SST4 over a variety of other G protein-coupled receptors, having affinities for M-1 muscarinic acetylcholin and D-3 dopamine receptors of around 500 and 1000 nM, respectively. Finally, NNC 26-9100 was found to fully inhibit forskolin-induced accumulation of adenosine 3',5'-cyclic monophosphate in baby hamster kidney cells, expressing the human SST4 receptor with an EC50 of 2 nM.

  DOI：

  10.1021/ja973325x

文献信息

• REMEDY FOR CORNEAL FAILURE
  申请人：Senju Pharmaceutical Co., Ltd.

  公开号：EP1566184A1

  公开（公告）日：2005-08-24

  The present invention provides a new type of pharmaceutical agent that recovers corneal sensitivity after corneal surgery or improves the condition of dry eye. Application of a somatostatin receptor agonist is expected to provide an improvement effect on decreased corneal sensitivity after cataract surgery or LASIK surgery, decreased corneal sensitivity and dry eye associated with corneal neurodegeneration such as neuroparalytic keratopathy, corneal ulcer, diabetic keratopathy and the like.

  本发明提供了一种新型药剂，可恢复角膜手术后的角膜敏感性或改善干眼症状况。应用体生长抑素受体激动剂可望对白内障手术或 LASIK 手术后角膜敏感性降低、角膜敏感性降低以及与神经麻痹性角膜病、角膜溃疡、糖尿病性角膜病等角膜神经变性相关的干眼症起到改善作用。
• Remedy for corneal failure
  申请人：Takayama Yoshiko

  公开号：US20060234922A1

  公开（公告）日：2006-10-19

  The present invention provides a new type of pharmaceutical agent that recovers corneal sensitivity after corneal surgery or improves the condition of dry eye. Application of a somatostatin receptor agonist is expected to provide an improvement effect on decreased corneal sensitivity after cataract surgery or LASIK surgery, decreased corneal sensitivity and dry eye associated with corneal neurodegeneration such as neuroparalytic keratopathy, corneal ulcer, diabetic keratopathy and the like.

  本发明提供了一种新型药剂，可恢复角膜手术后的角膜敏感性或改善干眼症状况。 应用体生长抑素受体激动剂可望对白内障手术或 LASIK 手术后角膜敏感性降低、角膜敏感性降低以及与神经麻痹性角膜病、角膜溃疡、糖尿病性角膜病等角膜神经变性相关的干眼症起到改善作用。
• USE OF SOMATOSTATIN AGONISTS AND ANTAGONISTS FOR TREATING DISEASES RELATED TO THE EYE
  申请人：NOVO NORDISK A/S

  公开号：EP1019050B1

  公开（公告）日：2002-03-20
• SOMATOSTATIN AGONISTS AND ANTAGONISTS
  申请人：NOVO NORDISK A/S

  公开号：EP0912551A1

  公开（公告）日：1999-05-06
• METHODS FOR TREATING MEMORY IMPAIRMENT
  申请人：Crider Albert Michael

  公开号：US20120283298A1

  公开（公告）日：2012-11-08

  Methods for administering a therapeutically effective amount of a somatostatin receptor-4 (SSTR4) agonist in order to treat learning and memory impairment for Alzheimer's disease is disclosed.