benzyl-2-(3,5-dichloropyridin-4-yl)hydrazinecarboxylate | 1370286-96-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl-2-(3,5-dichloropyridin-4-yl)hydrazinecarboxylate
• 英文别名: benzyl N-[(3,5-dichloropyridin-4-yl)amino]carbamate
• CAS: 1370286-96-6
• 化学式: C₁₃H₁₁Cl₂N₃O₂
• 分子量: 312.155
• InChiKey: OANXVQSYRCKPJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  63.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,5-二氯-4-碘吡啶 在 一水合肼 、 三乙胺 作用下， 以 二氯甲烷 、 正丁醇 为溶剂， 反应 0.5h， 生成 benzyl-2-(3,5-dichloropyridin-4-yl)hydrazinecarboxylate
  参考文献：
  名称：

  신규한 하이드라진 유도체 및 이의 용도

  摘要：

  本发明涉及各种新型羟肼衍生物化合物以及包含它们作为有效成分的用于P2X受体活性抑制的组合物。本发明可用于与P2X受体活性相关的各种疾病，如慢性炎症性疾病、炎症性疼痛、神经病性疼痛、自身免疫疾病或退行性疾病的预防或治疗。

  公开号：

  KR101728898B1

文献信息

• 신규한 하이드라진 유도체 및 이의 용도
  申请人：Gwangju Institute of Science and Technology 광주과학기술원(319980993815) BRN ▼410-82-07550

  公开号：KR101728898B1

  公开（公告）日：2017-04-21

  본 발명은 다양한 신규 하이드라진 유도체 화합물 및 이들을 유효성분으로 포함하는 P2X 수용체 활성 억제용 조성물에 관한 것이다. 본 발명은 P2X 수용체의 활성과 관련된 다양한 질환, 즉 만성 염증성 질환, 염증성 통증, 신경병성 통증, 자가면역 질환 또는 퇴행성 질환의 예방 또는 치료에 유용하게 이용될 수 있다.

  本发明涉及各种新型羟肼衍生物化合物以及包含它们作为有效成分的用于P2X受体活性抑制的组合物。本发明可用于与P2X受体活性相关的各种疾病，如慢性炎症性疾病、炎症性疼痛、神经病性疼痛、自身免疫疾病或退行性疾病的预防或治疗。
• Structure–Activity Relationships and Optimization of 3,5-Dichloropyridine Derivatives As Novel P2X₇Receptor Antagonists
  作者：Won-Gil Lee、So-Deok Lee、Joong-Heui Cho、Younghwan Jung、Jeong-hyun Kim、Tran T. Hien、Keon-Wook Kang、Hyojin Ko、Yong-Chul Kim

  DOI：10.1021/jm2012326

  日期：2012.4.26

  Screening of a library of chemical compounds showed that the dichloropyridine-based analogue 9 was a novel P2X(7) receptor antagonist. To optimize its activity, we assessed the structure-activity relationships (SAR) of 9, focusing on the hydrazide linker, the dichloropyridine skeleton, and the hydrophobic acyl (R-2) group. We found that the hydrazide linker and the 3,5-disubstituted chlorides in the pyridine skeleton were critical for P2X(7) antagonistic activity and that the presence of hydrophobic polycycloalkyl groups at the R-2 position optimized antagonistic activity. In the EtBr uptake assay in hP2X(7)-expressing HEK293 cells, the optimized antagonists, 5i and 52, had IC50 values of 4.9 and 13 nM, respectively. The antagonistic effects of 51 and 52 were paralleled by their ability to inhibit the release of the pro-inflammatory cytokine, IL-1 beta, by LPS/IFN-gamma/BzATP stimulation of THP-1 cells (IC50 = 1.3 and 9.2 nM, respectively). In addition, 52 strongly inhibited iNOS/COX-2 expression and NO production in THP-1 cells, further indicating that this compound blocks inflammatory signaling and suggesting that the dichloropyridine analogues may be useful in developing P2X(7) receptor targeted anti-inflammatory agents.