ethyl 3-benzamido-5-(chlorocarbonyl)-6,6-dimethyl-5,6-dihydropyrrolo[3,4-c]pyrazole-2(4H)-carboxylate | 1041015-48-8

• 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: ethyl 3-benzamido-5-(chlorocarbonyl)-6,6-dimethyl-5,6-dihydropyrrolo[3,4-c]pyrazole-2(4H)-carboxylate
• 英文别名: ethyl 3-(benzoylamino)-5-(chlorocarbonyl)-6,6-dimethyl-5,6-dihydropyrrolo[3,4-c]pyrazole-2(4H)-carboxylate；ethyl 3-benzamido-5-carbonochloridoyl-6,6-dimethyl-4H-pyrrolo[3,4-c]pyrazole-2-carboxylate
• CAS: 1041015-48-8
• 化学式: C₁₈H₁₉ClN₄O₄
• 分子量: 390.826
• InChiKey: ZOBXCRQSYINLLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  93.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-benzamido-5-(chlorocarbonyl)-6,6-dimethyl-5,6-dihydropyrrolo[3,4-c]pyrazole-2(4H)-carboxylate 在 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 N-(6,6-dimethyl-5-(4-methyl-2-phenylpiperazine-1-carbonyl)-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazol-3-yl)benzamide
  参考文献：
  名称：

  Discovery of Pyrroloaminopyrazoles as Novel PAK Inhibitors

  摘要：

  The P21-activated kinases (PAK) are emerging antitumor therapeutic targets. In this paper, we describe the discovery of potent PAK inhibitors guided by structure-based drug design. In addition, the efflux of the pyrrolopyrazole series was effectively reduced by applying multiple medicinal chemistry strategies, leading to a series of PAK inhibitors that are orally active in inhibiting tumor growth in vivo.

  DOI：

  10.1021/jm300204j
• 作为产物：
  描述：

  3-氨基-6,6-二甲基- 吡咯并[3,4-c]吡唑-2,5(4H,6H)-二羧酸 5-(1,1-二甲基乙基) 2-乙酯 在 盐酸 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 24.75h， 生成 ethyl 3-benzamido-5-(chlorocarbonyl)-6,6-dimethyl-5,6-dihydropyrrolo[3,4-c]pyrazole-2(4H)-carboxylate
  参考文献：
  名称：

  Discovery of Pyrroloaminopyrazoles as Novel PAK Inhibitors

  摘要：

  The P21-activated kinases (PAK) are emerging antitumor therapeutic targets. In this paper, we describe the discovery of potent PAK inhibitors guided by structure-based drug design. In addition, the efflux of the pyrrolopyrazole series was effectively reduced by applying multiple medicinal chemistry strategies, leading to a series of PAK inhibitors that are orally active in inhibiting tumor growth in vivo.

  DOI：

  10.1021/jm300204j

文献信息

• CARBONYLAMINO PYRROLOPYRAZOLES, POTENT KINASE INHIBITORS
  申请人：Zhang Junhu

  公开号：US20090318440A1

  公开（公告）日：2009-12-24

  Carbonylamino Pyrrolopyrazole compounds of formula I, compositions including these compounds and methods of their use are provided. Preferred compounds of formula I have activity as protein kinase inhibitors, including as inhibitors of PAK4.

  提供了化学式I的羰基氨基吡咯吡唑化合物，包括这些化合物的组合物以及它们的使用方法。化学式I的优选化合物具有作为蛋白激酶抑制剂的活性，包括作为PAK4的抑制剂。
• US7884117B2
  申请人：——

  公开号：US7884117B2

  公开（公告）日：2011-02-08
• [EN] CARBONYLAMINO PYRROLOPYRAZOLES, POTENT KINASE INHIBITORS<br/>[FR] CARBONYLAMINOPYRROLOPYRAZOLES, INHIBITEURS PUISSANTS DE KINASE
  申请人：PFIZER PROD INC

  公开号：WO2007072153A2

  公开（公告）日：2007-06-28

  (EN) Carbonylamino Pyrrolopyrazole compounds of formula (I), compositions including these compounds and methods of their use are provided. Preferred compounds of formula (I) have activity as protein kinase inhibitors, including as inhibitors of PAK4.(FR) La présente invention concerne des composés de carbonylamino-pyrrolopyrazole de formule I, des compositions comprenant ces composés et des procédés pour leur utilisation. Les composés de formule I préférés ont une activité en tant qu'inhibiteurs de protéine kinase, y compris en tant qu'inhibiteurs de PAK4.
• Discovery of Pyrroloaminopyrazoles as Novel PAK Inhibitors
  作者：Chuangxing Guo、Indrawan McAlpine、Junhu Zhang、Daniel D. Knighton、Susan Kephart、M. Catherine Johnson、Haitao Li、Djamal Bouzida、Anle Yang、Liming Dong、Joseph Marakovits、Jayashree Tikhe、Paul Richardson、Lisa C. Guo、Robert Kania、Martin P. Edwards、Eugenia Kraynov、James Christensen、Joseph Piraino、Joseph Lee、Eleanor Dagostino、Christine Del-Carmen、Ya-Li Deng、Tod Smeal、Brion W. Murray

  DOI：10.1021/jm300204j

  日期：2012.5.24

  The P21-activated kinases (PAK) are emerging antitumor therapeutic targets. In this paper, we describe the discovery of potent PAK inhibitors guided by structure-based drug design. In addition, the efflux of the pyrrolopyrazole series was effectively reduced by applying multiple medicinal chemistry strategies, leading to a series of PAK inhibitors that are orally active in inhibiting tumor growth in vivo.