4-[2]吡啶基邻苯二胺 | 471241-03-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 4-[2]吡啶基邻苯二胺
• 英文名称: 4-[2]pyridyl-o-phenylenediamine
• 英文别名: 4-[2]Pyridyl-o-phenylendiamin；4-(2-Pyridyl)-o-phenylenediamine；4-pyridin-2-ylbenzene-1,2-diamine
• CAS: 471241-03-9
• 化学式: C₁₁H₁₁N₃
• 分子量: 185.228
• InChiKey: CAMAADNLIGZSSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[2]吡啶基邻苯二胺 、 2-(3H-苯并咪唑-5-基)-3H-苯并咪唑-5-甲醛 以 硝基苯 为溶剂， 生成 5-Pyridin-2-yl-1H,3'H,3''H-[2,5';2',5'']terbenzoimidazole
  参考文献：
  名称：

  Synthesis and Evaluation of Terbenzimidazoles as Topoisomerase I Inhibitors

  摘要：

  The synthesis and pharmacological activity of a series of terbenzimidazoles are described. The ability of these derivatives to induce DNA cleavage in the presence of topoisomerase I was evaluated in vitro. These analogs were also assayed for their cytotoxicity in RPMI 8402 cells and the camptothecin-resistant CPT-K5 cells. In addition the potential for these compounds to serve as substrates for MDR1 was also determined. Several terbenzimidazoles exhibited similar cytotoxicity against variants of human tumor cells that either overexpress MDR1 or are camptothecin-resistant.

  DOI：

  10.1021/jm00018a024
• 作为产物：
  描述：

  4-(2-pyridyl)-2-nitroaniline 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 4-[2]吡啶基邻苯二胺
  参考文献：
  名称：

  新型，强效和选择性反式-2- [3-氧螺环[异苯并呋喃-1（3H），1'-环己基] -4'-基]苯并咪唑NPY Y5受体拮抗剂的合成及构效关系。

  摘要：

  描述了新型的2- [3-氧杂螺[异苯并呋喃-1（3H），1'-环己基] -4'-基]苯并咪唑NPY Y5受体拮抗剂的合成及其构效关系。通过将取代基并入苯并咪唑核心部分的5位或5位和6位两者中来优化前导化合物2a导致鉴定出5-（5-甲基-1,2,4-恶二唑-2 -基）苯并咪唑（2r：IC（50）= 3.3 nM）和5-（2-甲基四唑-5-基）苯并咪唑（2u：IC（50）= 5.9 nM），两者都是有效的，选择性的和口服的可生物利用的Y5受体拮抗剂。

  DOI：

  10.1016/j.bmcl.2008.08.021

文献信息

• Cook et al., Journal of the Chemical Society, 1943, p. 404
  作者：Cook et al.

  DOI：——

  日期：——
• Cook et al., Journal of the Chemical Society, <1943> 404
  作者：Cook et al.

  DOI：——

  日期：——
• US4297362A
  申请人：——

  公开号：US4297362A

  公开（公告）日：1981-10-27
• Syntheses and structure–activity relationships of novel, potent, and selective trans-2-[3-oxospiro[isobenzofuran-1(3H),1′-cyclohexan]-4′-yl]benzimidazole NPY Y5 receptor antagonists
  作者：Yoshio Ogino、Norikazu Ohtake、Yoshikazu Nagae、Kenji Matsuda、Makoto Ishikawa、Minoru Moriya、Maki Kanesaka、Yuko Mitobe、Junko Ito、Tetsuya Kanno、Akane Ishihara、Hisashi Iwaasa、Tomoyuki Ohe、Akio Kanatani、Takehiro Fukami

  DOI：10.1016/j.bmcl.2008.08.021

  日期：2008.9

  ole NPY Y5 receptor antagonists are described. Optimization of the lead compound 2a by incorporating substituents into the 5-position or into both the 5- and 6-positions of the benzimidazole core part led to the identification of 5-(5-methyl-1,2,4-oxadiazol-2-yl)benzimidazole (2r: IC(50)=3.3 nM) and 5-(2-methyltetrazol-5-yl)benzimidazole (2u: IC(50)=5.9 nM), both of which are potent, selective, and

  描述了新型的2- [3-氧杂螺[异苯并呋喃-1（3H），1'-环己基] -4'-基]苯并咪唑NPY Y5受体拮抗剂的合成及其构效关系。通过将取代基并入苯并咪唑核心部分的5位或5位和6位两者中来优化前导化合物2a导致鉴定出5-（5-甲基-1,2,4-恶二唑-2 -基）苯并咪唑（2r：IC（50）= 3.3 nM）和5-（2-甲基四唑-5-基）苯并咪唑（2u：IC（50）= 5.9 nM），两者都是有效的，选择性的和口服的可生物利用的Y5受体拮抗剂。
• Synthesis and Evaluation of Terbenzimidazoles as Topoisomerase I Inhibitors
  作者：Qun Sun、Barbara Gatto、Chiang Yu、Angela Liu、Leroy F. Liu、Edmond J. LaVoie

  DOI：10.1021/jm00018a024

  日期：1995.9

  The synthesis and pharmacological activity of a series of terbenzimidazoles are described. The ability of these derivatives to induce DNA cleavage in the presence of topoisomerase I was evaluated in vitro. These analogs were also assayed for their cytotoxicity in RPMI 8402 cells and the camptothecin-resistant CPT-K5 cells. In addition the potential for these compounds to serve as substrates for MDR1 was also determined. Several terbenzimidazoles exhibited similar cytotoxicity against variants of human tumor cells that either overexpress MDR1 or are camptothecin-resistant.