4-{7-[2-(Dimethylamino)ethyl]-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl}pyrimidin-2-amine | 762172-77-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-{7-[2-(Dimethylamino)ethyl]-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl}pyrimidin-2-amine
• 英文别名: 4-[7-[2-(dimethylamino)ethyl]-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine
• CAS: 762172-77-0
• 化学式: C₂₁H₂₁FN₆
• 分子量: 376.436
• InChiKey: DDXUKRBTIMUEPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  72.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  在 sodium tungstate (VI) dihydrate 、 双氧水 、 溶剂黄146 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 47.0h， 生成 4-{7-[2-(Dimethylamino)ethyl]-2-(4-fluorophenyl)imidazo[1,2-a]pyridin-3-yl}pyrimidin-2-amine
  参考文献：
  名称：

  Potent bicyclic inhibitors of malarial cGMP-dependent protein kinase: approaches to combining improvements in cell potency, selectivity and structural novelty

  摘要：

  Focussed studies on imidazopyridine inhibitors of Plasmodium falciparum cyclic GMP-dependent protein kinase (PfPKG) have significantly advanced the series towards desirable in vitro property space. LLE-based approaches towards combining improvements in cell potency, key physicochemical parameters and structural novelty are described, and a structure-based design hypothesis relating to substituent regiochemistry has directed efforts towards key examples with well-balanced potency, ADME and kinase selectivity profiles.

  DOI：

  10.1016/j.bmcl.2019.08.014

文献信息

• Synthesis and biological activity of imidazopyridine anticoccidial agents: Part II
  作者：Andrew Scribner、Richard Dennis、Shuliang Lee、Gilles Ouvry、David Perrey、Michael Fisher、Matthew Wyvratt、Penny Leavitt、Paul Liberator、Anne Gurnett、Chris Brown、John Mathew、Donald Thompson、Dennis Schmatz、Tesfaye Biftu

  DOI：10.1016/j.ejmech.2007.09.013

  日期：2008.6

  to current anticoccidials has prompted the search for new therapeutic agents with potent in vitro and in vivo activity against Eimeria. Recently, we reported the synthesis and biological activity of potent imidazo[1,2-a]pyridine anticoccidial agents. Antiparasitic activity is due to inhibition of a parasite specific cGMP-dependent protein kinase (PKG). In this study, we report the synthesis and anticoccidial

  球虫病是家禽业发病率和死亡率的主要原因。艾美球虫属的原生动物寄生虫侵入禽类宿主的肠壁，引起组织病理学，体重增加不良，在某些情况下甚至导致死亡。对当前抗球虫药的耐药性促使人们寻找对艾美尔球虫具有强大的体外和体内活性的新治疗剂。最近，我们报道了强效咪唑并[1,2-a]吡啶抗球虫药的合成和生物活性。抗寄生虫活性是由于抑制了寄生虫特异性cGMP依赖性蛋白激酶（PKG）。在这项研究中，我们报告了第二套此类化合物的合成和抗球虫活性，重点是在咪唑并吡啶7位胺侧链的衍生化。从这个系列中 几种化合物显示出亚纳摩尔的体外活性和商业水平的体内活性。但是，这些化合物的潜在遗传毒性使它们无法进一步开发。
• Antiprotozoal imidazopyridine compounds
  申请人：Wyvratt J Matthew

  公开号：US20060178358A1

  公开（公告）日：2006-08-10

  Compounds described by the Formula (I): (I) or pharmaceutically acceptable salts, or N-oxides thereof. The compounds are useful for the treatment and prevention of protozoal diseases in mammals and birds. A method for controlling coccidiosis in poultry comprises administering an effective amount of the compound alone, or in combination with one or more anticoccidial agent(s). A composition for controlling coccidiosis in poultry comprises the compound alone, or in combination with one or more anticoccidial agent(s). Methods for the treatment and prevention of mammalian protozoal diseases, such as, for example, toxoplasmosis, malaria, African trypanosomiasis, Chagas disease, and opportunistic infections comprise administering the compound alone, or in combination with one or more antiprotozoal agent(s).

  化合物的化学式为(I)：(I)或其药学上可接受的盐，或其N-氧化物。这些化合物可用于治疗和预防哺乳动物和鸟类的原虫病。一种控制家禽球虫病的方法包括单独或与一种或多种抗球虫药物联合给予有效剂量的化合物。一种用于控制家禽球虫病的组合物包括单独或与一种或多种抗球虫药物联合的化合物。用于治疗和预防哺乳动物原虫病的方法，例如弓形虫病、疟疾、非洲锥虫病、恶性疟疾和机会性感染，包括单独或与一种或多种抗原虫药物联合给予化合���。
• US7504501B2
  申请人：——

  公开号：US7504501B2

  公开（公告）日：2009-03-17
• Potent bicyclic inhibitors of malarial cGMP-dependent protein kinase: approaches to combining improvements in cell potency, selectivity and structural novelty
  作者：Jonathan M. Large、Kristian Birchall、Nathalie S. Bouloc、Andy T. Merritt、Ela Smiljanic-Hurley、Denise J. Tsagris、Mary C. Wheldon、Keith H. Ansell、Peter J. Coombs、Catherine A. Kettleborough、David Whalley、Lindsay B. Stewart、Paul W. Bowyer、David A. Baker、Simon A. Osborne

  DOI：10.1016/j.bmcl.2019.08.014

  日期：2019.10

  Focussed studies on imidazopyridine inhibitors of Plasmodium falciparum cyclic GMP-dependent protein kinase (PfPKG) have significantly advanced the series towards desirable in vitro property space. LLE-based approaches towards combining improvements in cell potency, key physicochemical parameters and structural novelty are described, and a structure-based design hypothesis relating to substituent regiochemistry has directed efforts towards key examples with well-balanced potency, ADME and kinase selectivity profiles.