1-nitro-9-(N-pyridinio)acridine hydrochloride | 20141-88-2

• 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-nitro-9-(N-pyridinio)acridine hydrochloride
• 英文别名: 1-(1-nitroacridin-9-yl)pyridinium chloride；N-(1-nitroacridin-9-yl)pyridinium chloride；N-(1-nitro-9-acridyl)-pyridinium chloride；(1-nitroacridyl-9-)-pyridinium chloride；1-<1-Nitro-acridinyl-(9)>-pyridiniumchlorid；1-Nitro-9-pyridino-acridinchlorid；1-(1-Nitro-9-acridinyl)pyridinium chloride；1-nitro-9-pyridin-1-ium-1-ylacridine;chloride
• CAS: 20141-88-2
• 化学式: C₁₈H₁₂N₃O₂*Cl
• 分子量: 337.765
• InChiKey: QEYLCUFSJDBYKQ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.58
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-nitro-9-(N-pyridinio)acridine hydrochloride 在 sodium azide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以84%的产率得到9-azido-1-nitroacridine
  参考文献：
  名称：

  Identification of an acridine photoaffinity probe for trypanocidal action

  摘要：

  Twenty-four acridine derivatives were screened for trypanocidal activity in Trypanosoma brucei in order to determine which structural features of the acridine molecule confer maximal antiparasitic activity. The synthesis of several new azidoacridine derivatives are also reported as well as an assessment of their value as possible photoaffinity probes for the study of acridine trypanocidal action. The most effective and selective acridine trypanocides, with and without irradiation, were the 3-amino-10-methylacridinium salt derivatives. With brief irradiation, one azidoacridine, 3-amino-6-azido-10-methylacridinium chloride, showed considerable trypanocidal activity at very limiting drug concentrations (10(-7)M) and warrants consideration as a possible photoaffinity probe.

  DOI：

  10.1021/jm00373a010
• 作为产物：
  描述：

  2-(3-硝基苯胺基)苯甲酸 在 三氯氧磷 作用下， 反应 0.33h， 生成 1-nitro-9-(N-pyridinio)acridine hydrochloride
  参考文献：
  名称：

  Acheson, R. Morrin; Constable, Edwin C.; Wright, R. Gordon McR., Journal of Chemical Research, Miniprint, 1983, # 1, p. 101 - 132

  摘要：

  DOI：

文献信息

• Hypoxia-selective antitumor agents. 4. Relationships between structure, physicochemical properties, and hypoxia-selective cytotoxicity for nitracrine analogs with varying side chains: the "iminoacridan hypothesis"
  作者：William A. Denny、Graham J. Atwell、Robert F. Anderson、William R. Wilson

  DOI：10.1021/jm00167a004

  日期：1990.5

  potent hypoxia-selective cytotoxin for mammalian cells in culture. In an attempt to modulate the degree of hypoxia selectivity among this class of compounds, we have studied a series of side-chain analogues of nitracrine. Both the electronic and steric properties of the side chain are shown to be important in determining the hypoxia selectivity of the compounds, by controlling the degree of aminoacridine/iminoacridan

  硝基ac啶衍生物硝唑林是培养中的哺乳动物细胞的一种有效的低氧选择性细胞毒素。为了调节这类化合物中的低氧选择性程度，我们研究了一系列硝苯胺的侧链类似物。通过控制氨基ac啶/亚氨基ac啶互变异构的程度，侧链的电子和空间性质都对确定化合物的缺氧选择性很重要。对具有修复缺陷的中国仓鼠细胞系UV4的研究表明，所有化合物的细胞毒性均归因于硝基还原和随后形成的大分子加合物。但是，与9-烷基氨基衍生物相比，全部以氨基ac啶互变异构体形式存在的化合物（例如9-氨基衍生物）致死性损害要小得多，在亚氨基ac构象中不同程度地存在。对于整套化合物，缺氧选择性细胞毒性的程度与亚氨基ac啶互变异构体的存在比例密切相关。
• 1-Nitro-9-alkylaminoalkylaminoacridines and salts thereof
  申请人：Politechnika Gdanska

  公开号：US04139531A1

  公开（公告）日：1979-02-13

  1-Nitro-9-alkylaminoalkylaminoacridins and their salts, as well as a method for obtaining these compounds, is described. The 1-nitro-9-alkylaminoalkylaminoacridines have the formula 1, ##STR1## wherein R is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, isopentyl, benzyl or cyclohexyl, whereas n is equal to 2 or 3. The salts are those derived from mineral acids or organic acids. These compounds have anti-neoplastic activity.

  1-硝基-9-烷基氨基烷基氨基吖啶及其盐类，以及获取这些化合物的方法被描述。1-硝基-9-烷基氨基烷基氨基吖啶的分子式为1，##STR1##，其中R代表甲基、乙基、丙基、异丙基、丁基、异丁基、异戊基、苄基或环己基，而n等于2或3。这些盐类来源于矿物酸或有机酸。这些化合物具有抗肿瘤活性。
• Wysocka-Skrzela, Barbara; Weltrowska, Grazyna; Ledochowski, Andrzej, Polish Journal of Chemistry, 1980, vol. 54, # 3, p. 619 - 623
  作者：Wysocka-Skrzela, Barbara、Weltrowska, Grazyna、Ledochowski, Andrzej

  DOI：——

  日期：——
• DENNY, WILLIAM A.;ATWELL, GRAHAM J.;ANDERSON, ROBERT F.;WILSON, WILLIAM R+, J. MED. CHEM., 33,(1990) N, C. 1288-1295
  作者：DENNY, WILLIAM A.、ATWELL, GRAHAM J.、ANDERSON, ROBERT F.、WILSON, WILLIAM R+

  DOI：——

  日期：——
• ACHSON, R. M.;CONSTABLE, E. C.;WRIGHT, R. G. ,, MCR.;TAYLOR, G. N., J. CHEM. RES. MICROFICHE, 1983, N 1, 2-3
  作者：ACHSON, R. M.、CONSTABLE, E. C.、WRIGHT, R. G. ,, MCR.、TAYLOR, G. N.

  DOI：——

  日期：——