1,7-dichloro-3,9-dimethyl-4,10-diazachrysene | 1149348-09-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1,7-dichloro-3,9-dimethyl-4,10-diazachrysene
• 英文别名: 1,7-dichloro-3,9-dimethylquino[8,7-h]quinoline；1,7-dichloro-3,9-dimethylquinolino[8,7-h]quinoline
• CAS: 1149348-09-3
• 化学式: C₁₈H₁₂Cl₂N₂
• 分子量: 327.213
• InChiKey: LLZMRRGVPMFVAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(3-氨丙基)吗啉 、 1,7-dichloro-3,9-dimethyl-4,10-diazachrysene 在 盐酸 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 96.0h， 以67%的产率得到3,9-dimethyl-N,N'-bis(3-morpholin-4-ylpropyl)quino[8,7-h]quinoline-1,7-diamine tetrahydrochloride
  参考文献：
  名称：

  A Chemotype That Inhibits Three Unrelated Pathogenic Targets: The Botulinum Neurotoxin Serotype A Light Chain, P. falciparum Malaria, and the Ebola Filovirus

  摘要：

  A 1,7-bis(alkylamino)diazachrysene-based small molecule was previously identified as an inhibitor of the botulinum neurotoxin serotype A light chain metalloprotease. Subsequently, a variety of derivatives of this chemotype were synthesized to develop structure activity relationships, and all are inhibitors of the BoNT/A LC. Three-dimensional analyses indicated that half of the originally discovered 1,7-DAAC structure superimposed well with 4-amino-7-chloroquinolinebased antimalarial agents. This observation led to the discovery that several of the 1,7-DAAC derivatives are potent in vitro inhibitors of Plasmodium falciparum and, in general, are more efficacious against CQ-resistant strains than against CQ-susceptible strains. In addition, by inhibiting beta-hematin formation, the most efficacious 1,7-DAAC-based antimalarials employ a mechanism of action analogous to that of 4,7-ACQ-based antimalarials and are well tolerated by normal cells. One candidate was also effective when administered orally in a rodent-based malaria model. Finally, the 1,7-DAAC-based derivatives were examined for Ebola filovirus inhibition in an assay employing Vero76 cells, and three provided promising antiviral activities and acceptably low toxicities.

  DOI：

  10.1021/jm100938u
• 作为产物：
  描述：

  ethyl 3-[[5-[3-ethoxy-1-methyl-3-oxo-prop-1-enylamino]-1-naphthyl]amino]but-2-enoate 在 Eaton′s Reagent 、 三氯氧磷 作用下， 反应 36.0h， 生成 1,7-dichloro-3,9-dimethyl-4,10-diazachrysene
  参考文献：
  名称：

  [EN] ELECTRONIC DEVICE INCLUDING A DIAZACHRYSENE DERIVATIVE
  [FR] DISPOSITIF ÉLECTRONIQUE COMPRENANT UN DÉRIVÉ DE DIAZACHRYSÈNE

  摘要：

  提供一种具有化学式I的化合物。在化学式I中：R1-R10相同或不同，可以是H、D、烷基、芳基、烷氧基、芳氧基、硅基，或者是烷基、芳基、烷氧基、芳氧基和硅基的氘代物，其中相邻的R基可以连接在一起形成环；其他所有位置为H或D。此外，在化学式I中：(i) R1-R3中至少有一个和R4-R6中至少有一个是烷基、烷氧基、硅基或氘代物，以及(ii) R1-R3中至少有一个和R4-R6中至少有一个是芳基、芳氧基或氘代物。

  公开号：

  WO2014130597A1

文献信息

• ELECTRONIC DEVICE INCLUDING A DIAZACHRYSENE DERIVATIVE
  申请人：E.I. DU PONT DE NEMOURS AND COMPANY

  公开号：US20150380664A1

  公开（公告）日：2015-12-31

  There is provided a compound having Formula I In Formula I: R 1 -R 10 are the same or different and can be H, D, alkyl, aryl, alkoxy, aryloxy, silyl, or deuterated analogs of alkyl, aryl, alkoxy, aryloxy and silyl, where adjacent R groups can be joined together to form a ring; and all other sites are H or D. Additionally in Formula I: (i) at least one of R 1 -R 3 and at least one of R 4 -R 6 is alkyl, alkoxy, silyl, or a deuterated analog, and (ii) at least one of R 1 -R 3 and at least one of R 4 -R 6 is aryl, aryloxy, or a deuterated analog.

  提供了一种化合物，其化学式为I。在化学式I中：R1-R10相同或不同，可以是H，D，烷基，芳基，烷氧基，芳氧基，硅烷基或烷基，芳基，烷氧基，芳氧基和硅烷基的氘代物，其中相邻的R基可以连接在一起形成环；其余位置为H或D。此外，在化学式I中：（i）至少有R1-R3中的一个和R4-R6中的至少一个是烷基，烷氧基，硅烷基或氘代物，（ii）至少有R1-R3中的一个和R4-R6中的至少一个是芳基，芳氧基或氘代物。
• METHOHDS OF INHIBITING VIRAL INFECTION
  申请人：Kinch Michael

  公开号：US20090170890A1

  公开（公告）日：2009-07-02

  A method of inhibiting viral infection in a mammal in need of same, includes administering an effective amount of at least one of the compounds of FGI-103 which are represented by 273, 365 and 510 either prophylactically to prevent viral infection, or therapeutically following viral infection. These compounds appear to selectively inhibit Caspase 8 as a method of preventing infective viral particle release. They can be administered IV, IP, orally or via other conventional administration routes. The compounds are highly effective, requiring relatively low dosages on the order of 1 ng/kg-200 mg/kg of body weight.
• US8207209B2
  申请人：——

  公开号：US8207209B2

  公开（公告）日：2012-06-26
• US9748497B2
  申请人：——

  公开号：US9748497B2

  公开（公告）日：2017-08-29
• [EN] METHODS OF INHIBITING VIRAL INFECTION<br/>[FR] PROCÉDÉS VISANT À INHIBER UNE INFECTION VIRALE
  申请人：FUNCTIONAL GENETICS INC

  公开号：WO2009055524A1

  公开（公告）日：2009-04-30

  A method of inhibiting viral infection in a mammal in need of same, includes administering an effective amount of at least one of the compounds of FGI- 103 which are represented by 273, 365 and 510 either prophylactically to prevent viral infection, or therapeutically following viral infection. These compounds appear to selectively inhibit Caspase 8 as a method of preventing infective viral particle release. They can be administered IV, IP, orally or via other conventional administration routes. The compounds are highly effective, requiring relatively low dosages on the order of 1 ng/kg - 200 mg/kg of body weight.