N-4-fluorobenzyl-2-imidazolealdehyde | 1249715-13-6

• 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: N-4-fluorobenzyl-2-imidazolealdehyde
• 英文别名: 1-[(4-fluorophenyl)methyl]-1H-imidazole-2-carbaldehyde；1-[(4-fluorophenyl)methyl]imidazole-2-carbaldehyde
• CAS: 1249715-13-6
• 化学式: C₁₁H₉FN₂O
• 分子量: 204.204
• InChiKey: UIGNWTMATFQJTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-4-fluorobenzyl-2-imidazolealdehyde 、 N-(2-hydrazinylquinazolin-4-yl)-N',N'-dimethylpropane-1,3-diamine 以58%的产率得到(E)-N1-(2-(2-((1-(4-fluorobenzyl)-1H-imidazol-2-yl)methylene)hydrazinyl)quinazolin-4-yl)-N3,N3-dimethylpropane-1,3-diamine
  参考文献：
  名称：

  Synthesis and biological evaluation of novel 2-(2-arylmethylene)hydrazinyl-4-aminoquinazoline derivatives as potent antitumor agents

  摘要：

  Two series of novel 2-(2-arylmethylene)hydrazinyl-4-aminoquinazoline derivatives were synthesized and evaluated for their cytotoxicity against H-460, HT-29, HepG2 and SGC-7901 cancer cell lines in vitro. Most compounds displayed moderate to excellent activity, with IC50 values ranging from 0.015 to 4.09 mu M against all tested cell lines, respectively. The most promising compound 9p (E)-2-(24(1-(2,3-dichlorobenzyl)-1H-imidazol-2-yl)methylene)hydrazinyl)-N-(1-methylpiperidin-4-yl)quinazolin-4-amine with IC50 values of 0.031 mu M, 0.015 mu M, 0.53 mu M and 0.58 mu M, which was 4- to 224 times more active than references 10 and Iressa, had emerged as a lead for further structural modifications. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.05.039
• 作为产物：
  描述：

  4-氟氯苄 在 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.33h， 生成 N-4-fluorobenzyl-2-imidazolealdehyde
  参考文献：
  名称：

  Synthesis and biological evaluation of novel 2-(2-arylmethylene)hydrazinyl-4-aminoquinazoline derivatives as potent antitumor agents

  摘要：

  Two series of novel 2-(2-arylmethylene)hydrazinyl-4-aminoquinazoline derivatives were synthesized and evaluated for their cytotoxicity against H-460, HT-29, HepG2 and SGC-7901 cancer cell lines in vitro. Most compounds displayed moderate to excellent activity, with IC50 values ranging from 0.015 to 4.09 mu M against all tested cell lines, respectively. The most promising compound 9p (E)-2-(24(1-(2,3-dichlorobenzyl)-1H-imidazol-2-yl)methylene)hydrazinyl)-N-(1-methylpiperidin-4-yl)quinazolin-4-amine with IC50 values of 0.031 mu M, 0.015 mu M, 0.53 mu M and 0.58 mu M, which was 4- to 224 times more active than references 10 and Iressa, had emerged as a lead for further structural modifications. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.05.039

文献信息

• 黄酮咪唑类化合物及其制备方法
  申请人：盐城师范学院

  公开号：CN107216315B

  公开（公告）日：2020-03-17

  本发明提供了一种黄酮咪唑类化合物,其通式为I、II或III，其中：R1为氢、烷基或羟基；R2为氢、烷基或羟基；R3为氢、烷基或羟基；R4为氢、烷基、取代芳香基；R5为氢或正丁基；R6为氢或氯；或上述化合物药学上可接收的盐。此外，本发明还提供了上述黄酮咪唑类化合物的制备方法。体外蛋白酪氨酸磷酸酶1B(PTP1B)活性检测结果显示，本发明合成的黄酮咪唑类化合物对PTP1B均表现出一定的抑制作用，本发明为开发以蛋白酪氨酸磷酸酶1B为靶点的2型糖尿病药物提供了基本的理论依据。该类化合物的合成路线短，制备方法简单，原料易得，成本低，因此，该类化合物有望为2型糖尿病治疗提供更多高效、安全的候选药物，有助于解决临床治疗问题。
• [EN] COMPOUNDS AND METHODS FOR INHIBITING HISTONE DEMETHYLASES<br/>[FR] COMPOSÉS ET PROCÉDÉS D'INHIBITION DES HISTONES DÉMÉTHYLASES
  申请人：EPITHERAPEUTICS APS

  公开号：WO2016033169A1

  公开（公告）日：2016-03-03

  The present application relates to compounds being of Formula (I), (II), (III), (IV), (V), (VI), (Ilia), (Illb), (IIIc), (Hid), (Hie), (Illf), and (Illg). Compounds of Formula (I) have the structure: wherein Q, R1, R18, R19, M, A and Y are as defined herein. The compounds of the application can modulate the activity of histone demethylases (HDMEs), and can be useful for the prevention and/or treatment of diseases in which genomic dysregulation is involved in the pathogenesis, e.g., cancer.

  本申请涉及的化合物属于以下公式：(I)、(II)、(III)、(IV)、(V)、(VI)、(Ilia)、(Illb)、(IIIc)、(Hid)、(Hie)、(Illf)和(Illg)。公式(I)的化合物具有以下结构：其中Q、R1、R18、R19、M、A和Y的定义如本文所述。本申请的化合物可以调节组蛋白去甲基化酶（HDMEs）的活性，并可用于预防和/或治疗基因组失调参与发病机制的疾病，例如癌症。
• Identification of novel imidazole flavonoids as potent and selective inhibitors of protein tyrosine phosphatase
  作者：Ling Zhang、Yu Ge、Qing Ming Wang、Cheng-He Zhou

  DOI：10.1016/j.bioorg.2019.03.074

  日期：2019.7

  imidazole flavonoids as new type of protein tyrosine phosphatase inhibitors were synthesized and characterized. Most of them gave potent protein phosphatase 1B (PTP1B) inhibitory activities. Especially, compound 11a could effectively inhibit PTP1B with an IC50 value of 0.63 μM accompanied with high selectivity ratio (9.5-fold) over T-cell protein tyrosine phosphatase (TCPTP). This compound is cell permeable

  合成了一系列咪唑类黄酮作为新型的蛋白质酪氨酸磷酸酶抑制剂。他们大多数给予有效的蛋白磷酸酶1B（PTP1B）抑制活性。尤其是，化合物11a可以有效抑制PTP1B，IC50值为0.63μM，并且具有比T细胞蛋白酪氨酸磷酸酶（TCPTP）高的选择性（9.5倍）。该化合物是细胞可渗透的，具有较低的细胞毒性。通过分子建模和动力学研究揭示了高结合亲和力和选择性。量子化学研究证实了活性必不可少的结构特征。
• COMPOUNDS AND METHODS FOR INHIBITING HISTONE DEMETHYLASES
  申请人：Epitherapeutics ApS

  公开号：US20160102096A1

  公开（公告）日：2016-04-14

  The present application relates to compounds being of Formula (I), (II), (III), (IV), (V), (VI), (IIIa), (IIIb), (IIIc), (IIId), (IIIe), (IIIf), and (IIIg). Compounds of Formula (I) have the structure: wherein Q, R 1 , R 18 , R 19 , M, A and Y are as defined herein. The compounds of the application can modulate the activity of histone demethylases (HDMEs), and can be useful for the prevention and/or treatment of diseases in which genomic dysregulation is involved in the pathogenesis, e.g., cancer.

  本申请涉及的化合物为公式（I），（II），（III），（IV），（V），（VI），（IIIa），（IIIb），（IIIc），（IIId），（IIIe），（IIIf）和（IIIg）的化合物。 公式（I）的化合物具有以下结构：其中Q，R1，R18，R19，M，A和Y如本文所定义。 本申请的化合物可以调节组蛋白去甲基化酶（HDMEs）的活性，并可用于预防和/或治疗基因组失调参与病理生理学的疾病，例如癌症。
• US9802941B2
  申请人：——

  公开号：US9802941B2

  公开（公告）日：2017-10-31