2-氨基-6-(4-甲基-1-哌嗪基)苯腈 | 63365-17-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 中文名称: 2-氨基-6-(4-甲基-1-哌嗪基)苯腈
• 英文名称: 6-amino-2-(4-methylpiperazinyl)benzenecarbonitrile
• 英文别名: 2-Amino-6-(4-methylpiperazin-1-yl)benzonitrile
• CAS: 63365-17-3
• 化学式: C₁₂H₁₆N₄
• 分子量: 216.286
• InChiKey: PAEDWGDWXDWOMH-UHFFFAOYSA-N

物化性质

• 熔点：
  151-154℃
• 沸点：
  425.1±45.0 °C(Predicted)
• 密度：
  1.20

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  56.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(1H-1,3-苯并咪唑-2-基)乙酸乙酯 、 2-氨基-6-(4-甲基-1-哌嗪基)苯腈 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以15%的产率得到4-氨基-3-(1H-苯并咪唑-2-基)-5-(4-甲基哌嗪-1-基)喹啉-2(1H)-酮
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jm800790t
• 作为产物：
  描述：

  2,6-二硝基苯腈 在 盐酸 、 铁粉 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.42h， 生成 2-氨基-6-(4-甲基-1-哌嗪基)苯腈
  参考文献：
  名称：

  N-（氨基苯基）草酰胺酸和酯类作为有效的口服活性抗过敏剂。

  摘要：

  DOI：

  10.1021/jm00138a020

文献信息

• Morpholine containing tetrazole-5-carboxamide derivatives
  申请人：American Home Products Corporation

  公开号：US04013647A1

  公开（公告）日：1977-03-22

  Anti-allergic agents of N-aromatic 1H-(or 2H) tetrazole-5-carboxamide derivation present the following formulae: ##STR1## in which R.sup.1 is --CN or --CONH.sub.2 ; R.sup.2 is hydrogen, lower alkyl, lower alkoxy, halo, polyhalo(lower)alkyl, lower alkyl carbonyl or carb(lower)alkoxy; X is --CH.sub.2 --, ##STR2## where R.sup.3 is lower alkyl and R.sup.4 is hydrogen or lower alkyl; Or a pharmaceutically acceptable salt thereof.

  N-芳香基1H-(或2H)四唑-5-羧酰胺衍生物的抗过敏剂具有以下式子： ##STR1## 其中R.sup.1是--CN或--CONH.sub.2；R.sup.2是氢、低碳基、低烷氧基、卤素、多卤素(低)烷基、低烷基羰基或羰(低)烷氧基；X是--CH.sub.2 --、##STR2## 其中R.sup.3是低碳基，R.sup.4是氢或低碳基；或其药学上可接受的盐。
• Method of treatment using tetrazole-5-carboxamide derivatives
  申请人：American Home Products Corporation

  公开号：US04057632A1

  公开（公告）日：1977-11-08

  Anti-allergic agents of N-aromatic 1H-(or 2H) tetrazole-5-carboxamide derivation present the following formulae: ##STR1## in which R.sup.1 is --CN or --CONH.sub.2 ; R.sup.2 is hydrogen, lower alkyl, lower alkoxy, halo, polyhalo(lower)alkyl, lower alkyl carbonyl or carb(lower)alkoxy; X is --CH.sub.2 --, ##STR2## where R.sup.3 is lower alkyl and R.sup.4 is hydrogen or lower alkyl; Or a pharmaceutically acceptable salt thereof.

  N-芳香基1H-(或2H)四唑-5-羧酰胺衍生物的抗过敏药物具有以下结构式：##STR1## 其中，R1为--CN或--CONH2；R2为氢，低碳基，低烷氧基，卤素，多卤素（低）烷基，低碳基羰基或羰（低）烷氧基；X为--CH2--，##STR2## 其中，R3为低碳基，R4为氢或低碳基；或其药学上可接受的盐。
• 2-Cyano-3- or 4-(substituted amino)oxanilic acid derivatives
  申请人：American Home Products Corporation

  公开号：US04087606A1

  公开（公告）日：1978-05-02

  The 2-cyano-3-or 4-(substituted amino) oxanilic acid derivatives of the formula: ##STR1## in which the group ##STR2## appears in the designated 3- or 4- position and R is --H; an alkali metal; .sup.+ NH.sub.4 ; alkyl of 1 to 6 carbon atoms, inclusive; aralkyl of 7 or 8 carbon atoms; or cycloalkyl of 5 or 6 carbon atoms; R.sup.1 is --H or alkyl of 1 to 9 carbon atoms; R.sup.2 is --H, alkyl of 1 to 9 carbon atoms or cycloalkyl of 3 to 6 carbon atoms; R.sup.1 and R.sup.2, together, with the nitrogen atom to which they are attached, are aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, piperazinyl, 4-lower alkyl-piperazinyl, morpholino or thiomorpholino; And pharmaceutically acceptable acid addition salts thereof are anti-allergic agents.

  公式为：##STR1##的2-氰基-3-或4-(取代氨基)氧化苯乙酸衍生物，其中基团##STR2##出现在指定的3-或4-位置，R为--H；碱金属；.sup.+ NH.sub.4；1至6个碳原子的烷基，包括；7或8个碳原子的芳基烷基；或5或6个碳原子的环烷基；R.sup.1为--H或1至9个碳原子的烷基；R.sup.2为--H，1至9个碳原子的烷基或3至6个碳原子的环烷基；R.sup.1和R.sup.2与它们附着的氮原子一起，是氮杂环丙基，氮杂环戊基，吡咯烷基，哌啶基，哌嗪基，4-低烷基哌嗪基，吗啉或硫代吗啉；以及其药学上可接受的酸盐是抗过敏剂。
• 2-Cyano-3-or 4-(substituted amino)oxanilic acid derivatives
  申请人：American Home Products Corporation

  公开号：US04054591A1

  公开（公告）日：1977-10-18

  The 2-cyano-3-or 4-(substituted amino)oxanilic acid derivatives of the formula: ##STR1## in which the group ##STR2## appears in the designated 3- or 4- position and R is -H; an alkali metal; .sup.+ NH.sub.4 ; alkyl of 1 to 6 carbon atoms, inclusive; aralkyl of 7 or 8 carbon atoms; or cycloalkyl of 5 or 6 carbon atoms; R.sup.1 is --H or alkyl of 1 to 9 carbon atoms; R.sup.2 is --H, alkyl of 1 to 9 carbon atoms or cycloalkyl of 3 to 6 carbon atoms; R.sup.1 and R.sup.2, together, with the nitrogen atom to which they are attached, are aziridinyl, azetidinyl, pyrrolidinyl, piperidinyl, piperazinyl, 4-lower alkyl-piperazinyl, morpholino or thiomorpholino; and pharmaceutically acceptable acid addition salts thereof are anti-allergic agents.

  公式为：##STR1## 的2-氰基-3-或4-(取代氨基)氧化邻苯二甲酸衍生物，其中组 ##STR2## 出现在指定的3-或4-位置，R为-H；碱金属；.sup.+ NH.sub.4；1至6个碳原子的烷基，包括；7或8个碳原子的芳基烷基；或5或6个碳原子的环烷基；R.sup.1为--H或1至9个碳原子的烷基；R.sup.2为--H，1至9个碳原子的烷基或3至6个碳原子的环烷基；R.sup.1和R.sup.2与它们所连接的氮原子一起，是氮杂环丙烷基，氮杂环戊烷基，吡咯烷基，哌啶基，哌嗪基，4-低烷基哌嗪基，吗啉基或硫代吗啉基；以及其药学上可接受的酸盐是抗过敏剂。
• Tetrazole-5-carboxamide derivatives
  申请人：American Home Products Corporation

  公开号：US04116960A1

  公开（公告）日：1978-09-26

  Anti-allergic agents of N-aromatic 1H-(or 2H) tetrazole-5-carboxamide derivation present the following formulae: ##STR1## in which R.sup.1 is --CN or --CONH.sub.2 ; R.sup.2 is hydrogen, lower alkyl, lower alkoxy, halo, polyhalo(lower)alkyl, lower alkyl carbonyl or carb(lower)alkoxy; X is --CH.sub.2 --, --O-- ##STR2## where R.sup.3 is lower alkyl and R.sup.4 is hydrogen or lower alkyl; Or a pharmaceutically acceptable salt thereof.

  N-芳香基1H-(或2H)四唑-5-羧酰胺衍生物的抗过敏剂具有以下式子：##STR1## 其中，R1为--CN或--CONH2；R2为氢、较低的烷基、较低的烷氧基、卤素、多卤素(较低)烷基、较低的烷基羰基或羰(较低)烷氧基；X为--CH2--、--O-- ##STR2## 其中，R3为较低的烷基，R4为氢或较低的烷基；或其药学上可接受的盐。