2-anilino-3,5-dihydro-5-phenyl-3-iminophenazine hydrochloride | 6285-16-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-anilino-3,5-dihydro-5-phenyl-3-iminophenazine hydrochloride
• 英文别名: 3-imino-N,5-diphenylphenazin-2-amine;hydrochloride
• CAS: 6285-16-1
• 化学式: C₂₄H₁₈N₄*ClH
• 分子量: 398.895
• InChiKey: IUWMSZMVYMFVQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.78
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-anilino-3,5-dihydro-5-phenyl-3-iminophenazine hydrochloride 在 盐酸 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 5.0h， 生成 3-[4-(1,2,3,4,6,7,8,9-octahydroquinolizin-9a-yl)butylimino]-N,5-diphenylphenazin-2-amine;hydrochloride
  参考文献：
  名称：

  Clofazimine analogs with antileishmanial and antiplasmodial activity

  摘要：

  A set of novel riminophenazine derivatives has been synthesized and evaluated for in vitro activity against chloroquine-sensitive (CQ-S) and chloroquine-resistant (CQ-R) strains of Plasmodium falciparum and against different species of Leishmania promastigotes. Most of the new compounds inhibited the growth of Leishmania promastigotes as well as CQ-S and CQ-R strains of P. falciparum with IC50 in submicromolar range, resulting in the best cases 1-2 orders of magnitude more potent than the parent compound clofazimine. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.11.028
• 作为产物：
  描述：

  邻氨基二苯胺 在 iron(III) chloride 作用下， 生成 2-anilino-3,5-dihydro-5-phenyl-3-iminophenazine hydrochloride
  参考文献：
  名称：

  Clofazimine analogs with antileishmanial and antiplasmodial activity

  摘要：

  A set of novel riminophenazine derivatives has been synthesized and evaluated for in vitro activity against chloroquine-sensitive (CQ-S) and chloroquine-resistant (CQ-R) strains of Plasmodium falciparum and against different species of Leishmania promastigotes. Most of the new compounds inhibited the growth of Leishmania promastigotes as well as CQ-S and CQ-R strains of P. falciparum with IC50 in submicromolar range, resulting in the best cases 1-2 orders of magnitude more potent than the parent compound clofazimine. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.11.028

文献信息

• Antitubercular activity of quinolizidinyl/pyrrolizidinylalkyliminophenazines
  作者：Michele Tonelli、Federica Novelli、Bruno Tasso、Anna Sparatore、Vito Boido、Fabio Sparatore、Sara Cannas、Paola Molicotti、Stefania Zanetti、Silvia Parapini、Roberta Loddo

  DOI：10.1016/j.bmc.2014.10.035

  日期：2014.12

  Novel riminophenazine derivatives, characterized by the presence of the basic and cumbersome quinolizidinylalkyl and pyrrolizidinylethyl moieties, have been synthesized and tested (Rema test) against Mycobacterium tuberculosis H37Rv and H37Ra, and six clinical isolates of Mycobacterium avium and Mycobacterium tuberculosis. Most compounds exhibited potent activity against the tested strains, resulting more active than clofazimine, isoniazid and ethambutol.The best compounds (4, 5, 12 and 13) exhibited a MIC in the range 0.82-0.86 mu M against all strains of Mycobacterium tuberculosis and, with the exception of 4 a MIC around 3.3 mu M versus M. avium. The corresponding values for clofazimine (CFM) were 1.06 and 4.23 mu M, respectively. Cytotoxicity was evaluated against three cell lines and compound 4 displayed a selectivity index (SI) versus the human cell line MT-4 comparable with that of CFM (SI = 5.23 vs 6.4). Toxicity against mammalian Vero 76 cell line was quite lower with SI = 79. (C) 2014 Elsevier Ltd. All rights reserved.
• OSULLIVAN, J. F., J. CHEM. RES. SYNOP., 1984, N 2, 52-53
  作者：OSULLIVAN, J. F.

  DOI：——

  日期：——
• Clofazimine analogs with antileishmanial and antiplasmodial activity
  作者：Anna Barteselli、Manolo Casagrande、Nicoletta Basilico、Silvia Parapini、Chiara M. Rusconi、Michele Tonelli、Vito Boido、Donatella Taramelli、Fabio Sparatore、Anna Sparatore

  DOI：10.1016/j.bmc.2014.11.028

  日期：2015.1

  A set of novel riminophenazine derivatives has been synthesized and evaluated for in vitro activity against chloroquine-sensitive (CQ-S) and chloroquine-resistant (CQ-R) strains of Plasmodium falciparum and against different species of Leishmania promastigotes. Most of the new compounds inhibited the growth of Leishmania promastigotes as well as CQ-S and CQ-R strains of P. falciparum with IC50 in submicromolar range, resulting in the best cases 1-2 orders of magnitude more potent than the parent compound clofazimine. (C) 2014 Elsevier Ltd. All rights reserved.