5-((1H-pyrrolo[2,3-b]pyridin-3-yl)methylene)-4-oxo-2-(phenylamino)-4,5-dihydrofuran-3-carboxylic acid | 1402055-32-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: 5-((1H-pyrrolo[2,3-b]pyridin-3-yl)methylene)-4-oxo-2-(phenylamino)-4,5-dihydrofuran-3-carboxylic acid
• 英文别名: 2-anilino-4-oxo-5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylidene)furan-3-carboxylic acid
• CAS: 1402055-32-6
• 化学式: C₁₉H₁₃N₃O₄
• 分子量: 347.33
• InChiKey: ZCXOLOPSZIKQTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  104.31
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2-苯胺-4-氧代-4,5-二氢-3-呋喃羧酸乙酯 在 哌啶 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 13.5h， 生成 5-((1H-pyrrolo[2,3-b]pyridin-3-yl)methylene)-4-oxo-2-(phenylamino)-4,5-dihydrofuran-3-carboxylic acid
  参考文献：
  名称：

  发现新型呋喃酮衍生物作为有效的Cdc7激酶抑制剂。

  摘要：

  Cdc7是一种丝氨酸-苏氨酸激酶，在DNA复制中起着保守而重要的作用，并且它被认为是潜在的抗癌靶标。在这里，我们报告新型呋喃酮衍生物作为Cdc7激酶抑制剂的设计，合成和构效关系。在存在1 mM ATP的情况下，化合物13被确定为Cdc7的强抑制剂，IC50值为0.6 nM，并显示出出色的激酶选择性。另外，它表现出缓慢的失速速率特性，这可能比已知的Cdc7抑制剂具有在体内产生延长的抑制作用的潜力。化合物13有效抑制癌细胞中的Cdc7活性，并有效诱导细胞死亡。

  DOI：

  10.1016/j.ejmech.2017.02.030

文献信息

• [EN] FURANONE DERIVATES AND METHODS OF USE THEREOF<br/>[FR] DÉRIVÉS DE FURANONE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：CARNA BIOSCIENCES INC

  公开号：WO2018084266A1

  公开（公告）日：2018-05-11

  Herein disclosed are compounds, compositions, kits, and methods of treating cancers using 7-azaindolyl furanone/thiophene derivatives. These derivatives inhibit serine-threonine kinase Cdc7, a recognized anticancer target affecting DNA replication. Further, the compounds disclosed herein possess potent inhibitory activity in the presence of adenosine triphosphate (ATP), demonstrate significant kinase selectivity, and offer advantages over known Cdc7 inhibitors with prolonged half-life and inhibitory effects.

  本文披露了使用7-氮杂吲哚基呋喃酮/噻吩衍生物治疗癌症的化合物、组合物、试剂盒和方法。这些衍生物抑制丝氨酸-苏氨酸激酶Cdc7，这是一种影响DNA复制的公认的抗癌靶点。此外，本文披露的化合物在存在三磷酸腺苷（ATP）时表现出强大的抑制活性，展示出显著的激酶选择性，并且相较于已知的Cdc7抑制剂具有更长的半衰期和更强的抑制效果。
• NOVEL FURANONE DERIVATIVE
  申请人：Irie Takayuki

  公开号：US20140018533A1

  公开（公告）日：2014-01-16

  To provide a novel furanone derivative, and a medicine including the same. The furanone derivative is represented by the formula (I): wherein A represents —COOR1 or a hydrogen atom; R1 represents a hydrogen atom, an optionally substituted hydrocarbon group, or an optionally substituted heterocycle; R2 and R3 are the same or different and each independently represent a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted phenyl group, an optionally substituted heterocycle, an optionally substituted heterocyclic fused ring, or an optionally substituted amino group; or alternatively, R2 and R3, taken together with the nitrogen atom to which they are attached, may form an optionally substituted heterocycle or an optionally substituted heterocyclic fused ring; and R4 represents a hydrogen atom or a halogen atom; with the proviso that when A represents —COOR1, R2 and R3 are not optionally substituted amino groups at the same time, and when A represents a hydrogen atom, R3 represents a hydrogen atom.

  提供一种新的呋喃酮衍生物，以及包含该衍生物的药物。该呋喃酮衍生物由以下式（I）表示：其中A代表—COOR1或氢原子；R1代表氢原子、可选择取代的碳氢基团或可选择取代的杂环基团；R2和R3相同或不同，每个独立地代表氢原子、可选择取代的碳氢基团、可选择取代的苯基团、可选择取代的杂环基团、可选择取代的杂环融合环或可选择取代的氨基团；或者，R2和R3与它们连接的氮原子一起，可以形成可选择取代的杂环或可选择取代的杂环融合环；R4代表氢原子或卤素原子；但当A代表—COOR1时，R2和R3不能同时是可选择取代的氨基团，当A代表氢原子时，R3代表氢原子。
• Furanone derivative
  申请人：Irie Takayuki

  公开号：US08742113B2

  公开（公告）日：2014-06-03

  To provide a novel furanone derivative, and a medicine including the same. The furanone derivative is represented by the formula (I): wherein A represents —COOR1 or a hydrogen atom; R1 represents a hydrogen atom, an optionally substituted hydrocarbon group, or an optionally substituted heterocycle; R2 and R3 are the same or different and each independently represent a hydrogen atom, an optionally substituted hydrocarbon group, an optionally substituted phenyl group, an optionally substituted heterocycle, an optionally substituted heterocyclic fused ring, or an optionally substituted amino group; or alternatively, R2 and R3, taken together with the nitrogen atom to which they are attached, may form an optionally substituted heterocycle or an optionally substituted heterocyclic fused ring; and R4 represents a hydrogen atom or a halogen atom; with the proviso that when A represents —COOR1, R2 and R3 are not optionally substituted amino groups at the same time, and when A represents a hydrogen atom, R3 represents a hydrogen atom.

  提供一种新的呋喃酮衍生物，以及包括该衍生物的药物。该呋喃酮衍生物由式(I)表示：其中，A代表—COOR1或氢原子；R1代表氢原子、可选取代的烃基或可选取代的杂环；R2和R3相同或不同，且每个独立地代表氢原子、可选取代的烃基、可选取代的苯基、可选取代的杂环、可选取代的杂环融合环或可选取代的氨基；或者，R2和R3连同它们所连接的氮原子可以形成可选取代的杂环或可选取代的杂环融合环；R4代表氢原子或卤素原子；但是，当A代表—COOR1时，R2和R3不能同时为可选取代的氨基，当A代表氢原子时，R3代表氢原子。
• Discovery of novel furanone derivatives as potent Cdc7 kinase inhibitors
  作者：Takayuki Irie、Tokiko Asami、Ayako Sawa、Yuko Uno、Mitsuharu Hanada、Chika Taniyama、Yoko Funakoshi、Hisao Masai、Masaaki Sawa

  DOI：10.1016/j.ejmech.2017.02.030

  日期：2017.4

  and it has been recognized as a potential anticancer target. Herein, we report the design, synthesis and structure-activity relationship of novel furanone derivatives as Cdc7 kinase inhibitors. Compound 13 was identified as a strong inhibitor of Cdc7 with an IC50 value of 0.6 nM in the presence of 1 mM ATP and showed excellent kinase selectivity. In addition, it exhibited slow off-rate characteristics

  Cdc7是一种丝氨酸-苏氨酸激酶，在DNA复制中起着保守而重要的作用，并且它被认为是潜在的抗癌靶标。在这里，我们报告新型呋喃酮衍生物作为Cdc7激酶抑制剂的设计，合成和构效关系。在存在1 mM ATP的情况下，化合物13被确定为Cdc7的强抑制剂，IC50值为0.6 nM，并显示出出色的激酶选择性。另外，它表现出缓慢的失速速率特性，这可能比已知的Cdc7抑制剂具有在体内产生延长的抑制作用的潜力。化合物13有效抑制癌细胞中的Cdc7活性，并有效诱导细胞死亡。