N-[3-甲氧基-4-(1,3-恶唑-5-基)苯基]-2-苯基乙酰胺 | 267405-93-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: N-[3-甲氧基-4-(1,3-恶唑-5-基)苯基]-2-苯基乙酰胺
• 英文名称: N-(3-methoxy-4-(oxazol-5-yl)phenyl)-2-phenylacetamide
• 英文别名: N-[3-Methoxy-4-(5-oxazolyl)phenyl]benzeneacetamide；N-[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]-2-phenylacetamide
• CAS: 267405-93-6
• 化学式: C₁₈H₁₆N₂O₃
• 分子量: 308.337
• InChiKey: FVMPOTYRHZJMAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  64.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2-甲氧基-4-硝基苯基)二乙酸甲二醇酯 在 palladium on activated charcoal 盐酸 、 4-二甲氨基吡啶 、 氢气 、 potassium carbonate 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 50.0 ℃ 、5.33 kPa 条件下， 生成 N-[3-甲氧基-4-(1,3-恶唑-5-基)苯基]-2-苯基乙酰胺
  参考文献：
  名称：

  Novel amide-based inhibitors of inosine 5′-monophosphate dehydrogenase

  摘要：

  A series of novel amide-based small molecule inhibitors of inosine monophosphate dehydrogenase (IMPDH) was explored. The synthesis and the structure-activity relationships (SARs) derived from in vitro studies are described. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00601-7

文献信息

• Discovery, Structure–Activity Relationships, and In Vivo Evaluation of Novel Aryl Amides as Brain Penetrant Adaptor Protein 2-Associated Kinase 1 (AAK1) Inhibitors for the Treatment of Neuropathic Pain
  作者：Richard A Hartz、Vijay T. Ahuja、Susheel J. Nara、C.M. Vijaya Kumar、Jeffrey M. Brown、Linda J. Bristow、Ramkumar Rajamani、Jodi K. Muckelbauer、Daniel Camac、Susan E. Kiefer、Lisa Hunihan、Michael Gulianello、Martin Lewis、Amy Easton、Jonathan S. Lippy、Neha Surti、Sreenivasulu N. Pattipati、Manoj Dokania、Saravanan Elavazhagan、Kumaran Dandapani、Brian D. Hamman、Jason Allen、Walter Kostich、Joanne J. Bronson、John E. Macor、Carolyn D. Dzierba

  DOI：10.1021/acs.jmedchem.1c00472

  日期：2021.8.12

  Effective treatment of chronic pain, in particular neuropathic pain, without the side effects that often accompany currently available treatment options is an area of significant unmet medical need. A phenotypic screen of mouse gene knockouts led to the discovery that adaptor protein 2-associated kinase 1 (AAK1) is a potential therapeutic target for neuropathic pain. The synthesis and optimization

  有效治疗慢性疼痛，特别是神经性疼痛，没有通常伴随当前可用治疗选择的副作用，是一个显着未满足的医疗需求领域。小鼠基因敲除的表型筛选导致发现接头蛋白 2 相关激酶 1 (AAK1) 是神经性疼痛的潜在治疗靶点。一系列基于芳基酰胺的 AAK1 抑制剂的构效关系的合成和优化导致59的鉴定，这是一种脑渗透性 AAK1 选择性抑制剂，被证明是一种有价值的工具化合物。在小鼠中评估了化合物59对 μ2 磷酸化的抑制。对59 人进行的研究在疼痛模型中证明该化合物在持续性疼痛的 II 期福尔马林模型和大鼠神经性疼痛的慢性收缩损伤诱导模型中是有效的。这些结果表明 AAK1 抑制是治疗神经性疼痛的一种有前途的方法。
• Novel inhibitors of IMPDH enzyme
  申请人：——

  公开号：US20040082562A1

  公开（公告）日：2004-04-29

  The present invention discloses the identification of the novel inhibitors of IMPDH (inosine-5′-monophosphate dehydrogenase). The compounds and pharmaceutical compositions disclosed herein are useful in treating or preventing IMPDH associated disorders, such as transplant rejection and autoimmune diseases.

  本发明揭示了IMPDH（鸟苷-5'-单磷酸脱氢酶）的新型抑制剂的鉴定。本文所披露的化合物和制药组合物在治疗或预防与IMPDH相关的疾病方面具有用途，例如移植排斥和自身免疫疾病。
• EP1127054A4
  申请人：——

  公开号：EP1127054A4

  公开（公告）日：2006-11-02
• NOVEL INHIBITORS OF IMPDH ENZYME
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：EP1127054A1

  公开（公告）日：2001-08-29
• Metabolism-modulating agents and uses therefor
  申请人：Whitehead Paul Jonathan

  公开号：US20060106097A1

  公开（公告）日：2006-05-18

  The present invention is directed to methods and agents for modulating adipogenesis. More particularly, the present invention relates to molecules that modulate the level or functional activity of inosine-5′ monophosphate dehydrogenase (IMPDH) and to their use in modulating the accumulation of lipids in adipocytes and/or the differentiation of preadipocytes to adipocytes for treating or preventing adiposity-related conditions including, but not limited to, obesity, lipoma, lipomatosis, cachexia or lipodystrophy or the loss of adipose tissue in trauma or atrophic conditions.