2-amino-5-(dimethylamino)benzonitrile | 141400-26-2

• 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: 2-amino-5-(dimethylamino)benzonitrile
• 英文别名: 2-Amino-5-(dimethylamino)benzonitrile
• CAS: 141400-26-2
• 化学式: C₉H₁₁N₃
• 分子量: 161.206
• InChiKey: WLYJEPCWQNJGQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  53
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  氯甲脒盐酸盐 、 2-amino-5-(dimethylamino)benzonitrile 以 二乙二醇二甲醚 为溶剂， 反应 3.0h， 生成 2,4-diamino-6-dimethylaminoquinazoline
  参考文献：
  名称：

  Antifolate and antibacterial activities of 6-substituted 2,4-diaminoquinazolines

  摘要：

  6-Substituted 2,4-diaminoquinazolines (1) are good inhibitors of dihydrofolate reductase (DHFR) and effective as growth inhibitors of intact bacterial cells in vitro. The most potent compounds in the in vitro tests were, however, ineffective against a systemic murine infection. Quantitative correlations were obtained between DHFR inhibition and the substituent constant molar refractivity (MR) for 3 of the 4 enzymes studied (Escherichia coli, Streptococcus faecalis, and bovine liver DHFR); for the fourth enzyme (Staphylococcus aureus DHFR) the best correlation was obtained with a combination of MR and the lipophilic parameter pi. The recognition that the conformational properties of the 6-substituent may play a vital role in mediating the binding of 1 to DHFR prompted the synthesis of novel analogues specifically designed to test this hypothesis. From these results it was possible to construct a simple schematic model of the binding site occupied by the 6-substituents; a subsequent molecular modelling study agreed with the features of this model.

  DOI：

  10.1016/0223-5234(92)90054-5
• 作为产物：
  描述：

  5-氯-2-硝基苯甲腈 在 tin 作用下， 以 盐酸 、 乙二醇二甲醚 、 乙醇 为溶剂， 反应 0.33h， 生成 2-amino-5-(dimethylamino)benzonitrile
  参考文献：
  名称：

  Antifolate and antibacterial activities of 6-substituted 2,4-diaminoquinazolines

  摘要：

  6-Substituted 2,4-diaminoquinazolines (1) are good inhibitors of dihydrofolate reductase (DHFR) and effective as growth inhibitors of intact bacterial cells in vitro. The most potent compounds in the in vitro tests were, however, ineffective against a systemic murine infection. Quantitative correlations were obtained between DHFR inhibition and the substituent constant molar refractivity (MR) for 3 of the 4 enzymes studied (Escherichia coli, Streptococcus faecalis, and bovine liver DHFR); for the fourth enzyme (Staphylococcus aureus DHFR) the best correlation was obtained with a combination of MR and the lipophilic parameter pi. The recognition that the conformational properties of the 6-substituent may play a vital role in mediating the binding of 1 to DHFR prompted the synthesis of novel analogues specifically designed to test this hypothesis. From these results it was possible to construct a simple schematic model of the binding site occupied by the 6-substituents; a subsequent molecular modelling study agreed with the features of this model.

  DOI：

  10.1016/0223-5234(92)90054-5

文献信息

• Synthesis and characterization of fluorescent amino acid dimethylaminoacridonylalanine
  作者：Chloe M. Jones、George A. Petersson、E. James Petersson

  DOI：10.24820/ark.5550190.p011.498

  日期：——

  Fluorescent amino acids are powerful biophysical tools as they can be used in structural or imaging studies of a given protein without significantly perturbing its native fold or function. Here, we have synthesized and characterized 7-(dimethylamino)acridon-2-ylalanine (Dad), a red-shifted derivative of the genetically-incorporable amino acid, acridon-2-ylalanine. Alkylation increases the quantum yield

  荧光氨基酸是强大的生物物理工具，因为它们可用于给定蛋白质的结构或成像研究，而不会显着干扰其天然折叠或功能。在这里，我们合成并表征了 7-(二甲基氨基)acridon-2-ylalanine (Dad)，它是遗传结合氨基酸 acridon-2-ylalanine 的红移衍生物。相对于之前发表的氨基酸 7-aminoacridon-2-ylalanine (Aad)，烷基化增加了 Dad 的量子产率和荧光寿命。 Dad 的这些特性使其成为一种潜在有价值的蛋白质标签，我们已经使用进化的氨酰 tRNA 合成酶对其进行基因整合的能力进行了初步测试。
• Design, Structure−Activity Relationships and in Vivo Characterization of 4-Amino-3-benzimidazol-2-ylhydroquinolin-2-ones: A Novel Class of Receptor Tyrosine Kinase Inhibitors
  作者：Paul A. Renhowe、Sabina Pecchi、Cynthia M. Shafer、Timothy D. Machajewski、Elisa M. Jazan、Clarke Taylor、William Antonios-McCrea、Christopher M. McBride、Kelly Frazier、Marion Wiesmann、Gena R. Lapointe、Paul H. Feucht、Robert L. Warne、Carla C. Heise、Daniel Menezes、Kimberly Aardalen、Helen Ye、Molly He、Vincent Le、Jayesh Vora、Johanna M. Jansen、Mary Ellen Wernette-Hammond、Alex L. Harris

  DOI：10.1021/jm800790t

  日期：2009.1.22

  The inhibition of key receptor tyrosine kinases (RTKs) that are implicated in tumor vasculature formation and maintenance, as well as tumor progression and metastasis, has been a major focus in oncology research over the last several years. Many potent small molecule inhibitors of vascular endothelial growth factor receptor (VEGFR) and platelet-derived growth factor receptor (PDGFR) kinases have been evaluated. More recently, compounds that act through the complex inhibition of multiple kinase targets have been reported and may exhibit improved clinical efficacy. We report herein a series of potent, orally efficacious 4-amino3-benzimidazol-2-ylhydroquinolin-2-one analogues as inhibitors of VEGF, PDGF, and fibroblast growth factor (FGF) receptor tyrosine kinases. Compounds in this class, such as 5 (TK1258), are reversible ATP-competitive inhibitors of VEGFR-2, FGFR-1, and PDGFR beta with IC50 values <0.1 mu M. On the basis of its favorable in vitro and in vivo properties, compound 5 was selected for clinical evaluation and is currently in phase I clinical trials.
• COMPOSITION DE DECOLORATION DES FIBRES KERATINIQUES TEINTES
  申请人：L'ORÉAL

  公开号：EP1313435B1

  公开（公告）日：2008-12-03
• Antifolate and antibacterial activities of 6-substituted 2,4-diaminoquinazolines
  作者：NV Harris、C Smith、K Bowden

  DOI：10.1016/0223-5234(92)90054-5

  日期：1992.1

  6-Substituted 2,4-diaminoquinazolines (1) are good inhibitors of dihydrofolate reductase (DHFR) and effective as growth inhibitors of intact bacterial cells in vitro. The most potent compounds in the in vitro tests were, however, ineffective against a systemic murine infection. Quantitative correlations were obtained between DHFR inhibition and the substituent constant molar refractivity (MR) for 3 of the 4 enzymes studied (Escherichia coli, Streptococcus faecalis, and bovine liver DHFR); for the fourth enzyme (Staphylococcus aureus DHFR) the best correlation was obtained with a combination of MR and the lipophilic parameter pi. The recognition that the conformational properties of the 6-substituent may play a vital role in mediating the binding of 1 to DHFR prompted the synthesis of novel analogues specifically designed to test this hypothesis. From these results it was possible to construct a simple schematic model of the binding site occupied by the 6-substituents; a subsequent molecular modelling study agreed with the features of this model.