5-amino-1-(tert-butyl)-3-(2-methylbenzofuran-3-yl)-1H-pyrazole-4-carboxamide | 1493523-59-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 5-amino-1-(tert-butyl)-3-(2-methylbenzofuran-3-yl)-1H-pyrazole-4-carboxamide
• 英文别名: 5-Amino-1-tert-butyl-3-(2-methyl-1-benzofuran-3-yl)pyrazole-4-carboxamide；5-amino-1-tert-butyl-3-(2-methyl-1-benzofuran-3-yl)pyrazole-4-carboxamide
• CAS: 1493523-59-3
• 化学式: C₁₇H₂₀N₄O₂
• 分子量: 312.371
• InChiKey: IKFLEKNPOKNLNA-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：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  100
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-甲基苯并呋喃-3-甲醛 在 N-溴代丁二酰亚胺(NBS) 、 sodium ethanolate 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 5-amino-1-(tert-butyl)-3-(2-methylbenzofuran-3-yl)-1H-pyrazole-4-carboxamide
  参考文献：
  名称：

  Potent and Selective Inhibitors of CDPK1 from T. gondii and C. parvum Based on a 5-Aminopyrazole-4-carboxamide Scaffold

  摘要：

  5-Aminopyrazole-4-carboxamide was used as an alternative scaffold to substitute for the pyrazolopyrimidine of a known "bumped kinase inhibitor" to create selective inhibitors of calcium-dependent protein kinase-1 from both Toxoplasma gondii and Cryptosporidium parvum. Compounds with low nanomolar inhibitory potencies against the target enzymes were obtained. The most selective inhibitors also exhibited submicromolar activities in T. gondii cell proliferation assays and were shown to be non-toxic to mammalian cells.

  DOI：

  10.1021/ml400315s

文献信息

• [EN] 5-AMINOPYRAZOLE-4-CARBOXAMIDE INHIBITORS OF CDPK1 FROM T. GONDII AND C. PARVUM<br/>[FR] INHIBITEURS 5-AMINOPYRAZOLE-4-CARBOXAMIDE DE CDPK1 ISSUES DE T. GONDII ET C. PARVUM
  申请人：UNIV WASHINGTON CT COMMERCIALI

  公开号：WO2014189947A1

  公开（公告）日：2014-11-27

  The present disclosure is generally directed to compositions and methods for treating apicomplexan protozoan related disease, such as toxoplasmosis and cryptosporidiosis.

  本公开通常涉及用于治疗顶复门原虫相关疾病的组合物和方法，例如弓形虫病和隐孢子虫病。
• 5-AMINOPYRAZOLE-4-CARBOXAMIDE INHIBITORS OF CDPK1 FROM T. GONDII AND C. PARVUM
  申请人：University of Washington through its Center for Commercialization

  公开号：EP2999696A1

  公开（公告）日：2016-03-30
• US9518026B2
  申请人：——

  公开号：US9518026B2

  公开（公告）日：2016-12-13
• US9956214B2
  申请人：——

  公开号：US9956214B2

  公开（公告）日：2018-05-01
• Potent and Selective Inhibitors of CDPK1 from <i>T. gondii</i> and <i>C. parvum</i> Based on a 5-Aminopyrazole-4-carboxamide Scaffold
  作者：Zhongsheng Zhang、Kayode K. Ojo、RamaSubbaRao Vidadala、Wenlin Huang、Jennifer A. Geiger、Suzanne Scheele、Ryan Choi、Molly C. Reid、Katelyn R. Keyloun、Kasey Rivas、Latha Kallur Siddaramaiah、Kenneth M. Comess、Kenneth P. Robinson、Philip J. Merta、Lemma Kifle、Wim G. J. Hol、Marilyn Parsons、Ethan A. Merritt、Dustin J. Maly、Christophe L. M. J. Verlinde、Wesley C. Van Voorhis、Erkang Fan

  DOI：10.1021/ml400315s

  日期：2014.1.9

  5-Aminopyrazole-4-carboxamide was used as an alternative scaffold to substitute for the pyrazolopyrimidine of a known "bumped kinase inhibitor" to create selective inhibitors of calcium-dependent protein kinase-1 from both Toxoplasma gondii and Cryptosporidium parvum. Compounds with low nanomolar inhibitory potencies against the target enzymes were obtained. The most selective inhibitors also exhibited submicromolar activities in T. gondii cell proliferation assays and were shown to be non-toxic to mammalian cells.