3-tert-butyl-1-benzyl-N-phenyl-1H-pyrazole-5-carboxamide | 353504-17-3

• 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: 3-tert-butyl-1-benzyl-N-phenyl-1H-pyrazole-5-carboxamide
• 英文别名: 2-Benzyl-5-tert-butyl-2H-pyrazole-3-carboxylic acid phenylamide；2-benzyl-5-tert-butyl-N-phenylpyrazole-3-carboxamide
• CAS: 353504-17-3
• 化学式: C₂₁H₂₃N₃O
• 分子量: 333.433
• InChiKey: FWCSXKSIXVAWIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  46.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-苄基-3-叔丁基-1H-吡唑-5-羧酸 、 苯胺 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以80%的产率得到3-tert-butyl-1-benzyl-N-phenyl-1H-pyrazole-5-carboxamide
  参考文献：
  名称：

  Novel Orally Active Antimalarial Thiazoles

  摘要：

  An aminomethylthiazole pyrazole carboxamide lead 3 with good in vitro antiplasmodial activity [IC50: 0.08 mu M (K1, chloroquine and multidrug resistant strain) and 0.07 mu M (NF54, chloroquine sensitive strain)] and microsomal metabolic stability was identified from whole cell screening of a SoftFocus kinase library. Compound 3 also exhibited in vivo activity in the P. berghei mouse model at 4 x 50 mg/kg administration via the oral route, showing 99.5% activity and 9 days survival and showed low in vitro cytotoxicity. Pharmacokinetic studies in rats revealed good oral bioavailability (51% at 22 mg/kg) with a moderate rate of absorption, reasonable half-life (t(1/2) 3 h), and high volume of distribution with moderately high plasma and blood clearance after IV administration. Toward toxicity profiling, 3 exhibited moderate potential to inhibit CYP1A2 (IC50 = 1.5 mu M) and 2D6 (IC50 = 0.4 mu M) as well as having a potential hERG liability (IC50 = 3.7 mu M).

  DOI：

  10.1021/jm201108k

文献信息

• Blockade of voltage dependent sodium channels
  申请人：——

  公开号：US20030171403A1

  公开（公告）日：2003-09-11

  Compounds of formula (1), and pharmaceutically acceptable salts thereof, are capable of blockading voltage-dependent sodium channels and are useful in particular, in treating glaucoma and multiple sclerosis.

  式（1）的化合物及其药学上可接受的盐能够阻断电压依赖性钠通道，并且在治疗青光眼和多发性硬化症方面具有用处。
• [EN] BLOCKADE OF VOLTAGE DEPENDENT SODIUM CHANNELS<br/>[FR] BLOCAGE DE CANAUX SODIQUES DEPENDANT DE LA TENSION
  申请人：UNIV LONDON

  公开号：WO2001057024A1

  公开（公告）日：2001-08-09

  Compounds of formula (I), and pharmaceutically acceptable salts thereof, are capable of blockading voltage-dependent sodium channels and are useful in particular, in treating glaucoma and multiple sclerosis.

  式(I)的化合物及其药学上可接受的盐，能够阻断电压依赖性钠通道，特别适用于治疗青光眼和多发性硬化症。
• BLOCKADE OF VOLTAGE DEPENDENT SODIUM CHANNELS
  申请人：University College London

  公开号：EP1252156A1

  公开（公告）日：2002-10-30
• US7009056B2
  申请人：——

  公开号：US7009056B2

  公开（公告）日：2006-03-07
• US7790761B2
  申请人：——

  公开号：US7790761B2

  公开（公告）日：2010-09-07