N,N-diethyl-5-(pyridin-4-ylimino)-5H-benzo[a]phenoxazin-9-amine | 1187533-34-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: N,N-diethyl-5-(pyridin-4-ylimino)-5H-benzo[a]phenoxazin-9-amine
• 英文别名: SSJ-183；Unii-2EJ2tik905；N,N-diethyl-5-pyridin-4-yliminobenzo[a]phenoxazin-9-amine
• CAS: 1187533-34-1
• 化学式: C₂₅H₂₂N₄O
• 分子量: 394.476
• InChiKey: HBSWMATYASLRBW-UHFFFAOYSA-N

物化性质

• 熔点：
  247-248 °C
• 沸点：
  551.9±50.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N-diethyl-5-(pyridin-4-ylimino)-5H-benzo[a]phenoxazin-9-amine 在 盐酸 作用下， 生成 N,N-diethyl-5-pyridin-4-yliminobenzo[a]phenoxazin-9-amine;hydrochloride
  参考文献：
  名称：

  Discovery of Novel Benzo[a]phenoxazine SSJ-183 as a Drug Candidate for Malaria

  摘要：

  Malaria is a serious infectious disease caused by protozoan parasites in tropical and subtropical regions. Even inhabitants of temperate zones are exposed to the danger of malaria infection because of travel and global warming. Novel, effective,safe, and inexpensive drugs are required to treat malaria and. . contribute to the global goal of eradication. A search for new antimalarial-agents has by the synthesis of by biological evaluations. The derivative SSJ-183(5) having a 4-aminopyridine group, showed an IC50 value against Plasmodium falciparum of 7.6 nM and a selectivity index of > 7300: Cure was acheived by three oral doses of 5 at 100 mg/kg to mice infected with the Plasmodium berghei ANKA strain. The safety of 5 was supported acute toxicity testing in mice with single doses up to 2000 mg/kg po, chromosome aberration test, in vitro as well as in vivo micronucleus tests and phototoxicity studies in mice. Thus, 5 is a promising candidate as a new antimalarial agent.

  DOI：

  10.1021/ml100120a
• 作为产物：
  描述：

  Nile Blue base 在 air 作用下， 反应 11.0h， 生成 N,N-diethyl-5-(pyridin-4-ylimino)-5H-benzo[a]phenoxazin-9-amine
  参考文献：
  名称：

  JP5773123

  摘要：

  公开号：

文献信息

• Reversible Near-Infrared pH Probes Based on Benzo[<i>a</i>]phenoxazine
  作者：Wu Liu、Ru Sun、Jian-Feng Ge、Yu-Jie Xu、Ying Xu、Jian-Mei Lu、Isaum Itoh、Masataka Ihara

  DOI：10.1021/ac4013539

  日期：2013.8.6

  Several benzo[a]phenoxazine derivatives containing substituted N-aromatic groups are evaluated for their pH-dependent absorption and emission properties. Among the compounds exhibiting optical responses under near-neutral and subacid pH conditions, benzo[a]phenoxazine derivatives with an electron-withdrawing aromatic group attached to nitrogen of the imino group show potential application as near-infrared

  评价了几种含有取代的N-芳族基团的苯并[ a ]吩恶嗪衍生物的pH依赖性吸收和发射性质。在近中性和亚酸性pH条件下表现出光学响应的​​化合物中，亚氨基基团的氮上带有吸电子芳族基团的苯并[ a ]吩恶嗪衍生物显示出作为近红外pH传感器的潜在应用。设计并合成了三种基于具有不同吡啶鎓结构的苯并[ a ]吩恶嗪的水溶性pH探针。在含0.1％二甲基亚砜（DMSO）的缓冲溶液中，它们的pH依赖可逆发射，位于625–850 nm，荧光增强8.2–40.1倍，其计算出的p Ka值分别为2.7、5.8和7.1。包含三种苯并[ a ]吩恶嗪的复合探针在pH 1.9-8.0范围内显示线性的pH-发射关系。还报道了使用HeLa细胞的体外测定法实时检测细胞内pH的方法。
• Novel synthetic route for antimalarial benzo[a]phenoxazine derivative SSJ-183 and two active metabolites
  作者：Yuki Mizukawa、Jian-Feng Ge、Abu Bakar Md、Isamu Itoh、Christian Scheurer、Sergio Wittlin、Reto Brun、Hiroyuki Matsuoka、Masataka Ihara

  DOI：10.1016/j.bmc.2014.04.066

  日期：2014.7

  A productive synthesis of benzo[a]phenoxazine derivative SSJ-183 (1), a promising lead for antimalarial agents, was developed using a one pot procedure. Furthermore, N-deethylated metabolite 3 and bis-N,N-deethylated metabolite 4 were synthesized by the application of the method. The metabolites 3 and 4 showed comparable and ∼2-fold increased activities against drug-sensitive and drug-resistant Plasmodium falciparum parasites.
• JP5773123
  申请人：——

  公开号：——

  公开（公告）日：——
• Discovery of Novel Benzo[<i>a</i>]phenoxazine SSJ-183 as a Drug Candidate for Malaria
  作者：Jian-Feng Ge、Chika Arai、Mei Yang、Abu Bakar Md.、Jun Lu、Nasser S. M. Ismail、Sergio Wittlin、Marcel Kaiser、Reto Brun、Susan A. Charman、Tien Nguyen、Julia Morizzi、Isamu Itoh、Masataka Ihara

  DOI：10.1021/ml100120a

  日期：2010.10.14

  Malaria is a serious infectious disease caused by protozoan parasites in tropical and subtropical regions. Even inhabitants of temperate zones are exposed to the danger of malaria infection because of travel and global warming. Novel, effective,safe, and inexpensive drugs are required to treat malaria and. . contribute to the global goal of eradication. A search for new antimalarial-agents has by the synthesis of by biological evaluations. The derivative SSJ-183(5) having a 4-aminopyridine group, showed an IC50 value against Plasmodium falciparum of 7.6 nM and a selectivity index of > 7300: Cure was acheived by three oral doses of 5 at 100 mg/kg to mice infected with the Plasmodium berghei ANKA strain. The safety of 5 was supported acute toxicity testing in mice with single doses up to 2000 mg/kg po, chromosome aberration test, in vitro as well as in vivo micronucleus tests and phototoxicity studies in mice. Thus, 5 is a promising candidate as a new antimalarial agent.