2,2’,4,4’-四硝基二苯甲酮 | 71535-97-2

• 物质功能分类: 化学试剂 - 氘代试剂
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,2’,4,4’-四硝基二苯甲酮
• 中文别名: 氘代噻菌灵
• 英文名称: 2,2',4,4'–tetranitrodibenzophenone
• 英文别名: 2,2',4,4'-tetranitrobenzophenone；2,4,2',4'-tetranitro-benzophenone；2,4,2',4'-Tetranitro-benzophenon；Bis-(2.4-dinitro-phenyl)-keton；bis(2,4-dinitrophenyl)methanone
• CAS: 71535-97-2
• 化学式: C₁₃H₆N₄O₉
• 分子量: 362.212
• InChiKey: FAFWLBOSKDZHKI-UHFFFAOYSA-N

物化性质

• 熔点：
  230°C
• 沸点：
  650.2±55.0 °C(predicted)
• 密度：
  1.685±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)
• 溶解度：
  乙腈（微溶，加热）、DMSO（微溶，加热）

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  200
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,2’,4,4’-四硝基二苯甲酮 在 盐酸 、 sodium carbonate 、 N,N-二异丙基乙胺 、 tin(ll) chloride 、 三氯氧磷 作用下， 以 N,N-二甲基乙酰胺 、 乙腈 为溶剂， 反应 28.0h， 生成 N-[9-(4-dimethylamino-phenylamino)-6-(3-pyrrolidin-1-yl-propionylamino)-acridin-3-yl]-3-pyrrolidin-1-yl-propionamide
  参考文献：
  名称：

  Structure-based design of benzylamino-acridine compounds as G-quadruplex DNA telomere targeting agents

  摘要：

  The design, synthesis, biophysical and biochemical evaluation is presented of a new series of benzylamino-substituted acridines as G-quadruplex binding telomerase inhibitors. Replacement of the previously reported anilino substituents by benzylamino groups results in enhanced quadruplex interaction, and for one compound, superior telomerase inhibitory activity. (c) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2007.01.056
• 作为产物：
  描述：

  二苯基甲烷 在 chromium(VI) oxide 、 硫酸 、 溶剂黄146 、 potassium nitrate 作用下， 反应 3.0h， 生成 2,2’,4,4’-四硝基二苯甲酮
  参考文献：
  名称：

  Antiprotozoal Activity and DNA Binding of Dicationic Acridones

  摘要：

  Dicationic acridone derivatives were synthesized and their antiparasitic activity was evaluated. Acridones displayed in vitro nanomolar IC50 values against Trypanosoma brucei rhodesiense STIB900 with selectivity indices >1000. Compounds 1b, 3a, and 3b were as potent as the reference drug melarsoprol in this assay. Submicromolar-range activities were observed against wild-type (NF54) and resistant (K1) strains of Plasmodium falciparum, whereas no significant activity was detected against Trypanosoma cruzi or Leishmania donovani. Compounds 1a and 1b were curative in the STIB900 mouse model for human African trypanosomiasis. UV spectrophotometric titrations and circular dichroism (CD) experiments with fish sperm (FS) DNA showed that these compounds form complexes with DNA with binding affinities in the 10(4) M-1 range. Biological and biophysical data show that antiparasitic activity, toxicity, and DNA binding of this series of acridones are dependent on the relative position of both imidazolinium cations on the heterocyclic scaffold.

  DOI：

  10.1021/jm5018303

文献信息

• Therapeutic acridone and acridine compounds
  申请人：——

  公开号：US20030207909A1

  公开（公告）日：2003-11-06

  The present invention pertains to acridone and acridine compounds of formula (I), wherein either: (a) K is ═O, L is —H, alpha is a single bond, beta is a double bond, gamma is a single bond (acridones); or, (b) K is a 9-substituent, L is absent, alpha is a double bond, beta is a single bond, gamma is a double bond (acridines); and wherein: J 1 is a 2- or 3-substituent; J 2 is a 6- or 7-substituent; J 1 and J 2 are each independently a group of the formula —NHCO(CH 2 ) n NR 1 R 2 , wherein: n is an integer from 1 to 5; and, R 1 and R 2 are independently hydrogen, C 1-7 alkyl, C 3-20 heterocyclyl, or C 5-20 aryl, or R 1 and R 2 , taken together with the nitrogen atom to which they are attached, form a heterocyclic ring having from 3 to 8 ring atoms; and wherein, when K is a 9-substituent. K is a group of the formula —N(R N )Q, wherein: R N is an amino substituent and is hydrogen, C 1-7 alkyl, C 3-20 heterocyclyl, or C 5-20 aryl; and, Q is C 1-7 alkyl, C 3-20 heterocyclyl, or (C 5-20 aryl, and is optionally substituted; and pharmaceutically acceptable salts, esters, amides, solvates, hydrates, and protected forms thereof. The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit telomerase, to regulate cell prol iferation, and in the treatment of proliferative conditions, such as cancer.

  本发明涉及式(I)的吖啶和吖啶类化合物，其中：(a) K为═O，L为—H，α为单键，β为双键，γ为单键（吖啶类）；或者，(b) K为9-取代基，L不存在，α为双键，β为单键，γ为双键（吖啶类）；其中：J1为2-或3-取代基；J2为6-或7-取代基；J1和J2各自独立为式—NHCO(CH2)nNR1R2的基团，其中：n为1到5的整数；R1和R2独立地为氢、C1-7烷基、C3-20杂环烷基或C5-20芳基，或者R1和R2与它们连接的氮原子一起形成具有3到8个环原子的杂环环；当K为9-取代基时，K为式—N(RN)Q的基团，其中：RN为氨基取代基，为氢、C1-7烷基、C3-20杂环烷基或C5-20芳基；Q为C1-7烷基、C3-20杂环烷基或(C5-20芳基，且可选择性取代；以及药学上可接受的盐、酯、酰胺、溶剂化合物、水合物和其保护形式。本发明还涉及包含此类化合物的药物组合物，以及在体内外使用此类化合物和组合物来抑制端粒酶、调节细胞增殖，以及治疗增殖性疾病，如癌症。
• Novel Acridine-Triazenes as Prototype Combilexins: Synthesis, DNA Binding, and Biological Activity
  作者：Adrian W. McConnaughie、Terence C. Jenkins

  DOI：10.1021/jm00018a009

  日期：1995.9

  molecular fragments, have been examined by fluorescence quenching and thermal denaturation studies with calf thymus DNA and two oligonucleotides, [poly(dA-dT)]2 and [poly(dG-dC)]2. In addition, the binding behaviors of these acridine compounds are compared to those of proflavine (3,6-diaminoacridine) and its 9-phenyl derivative. The results indicate that the hybrid agents (i) are more DNA-affinic than either

  使用DNA模板指导的方法已经开发了一系列双功能配体作为结合DNA的原型组合毒素。这些新型药物含有1,3-二芳基三氮烯连接基部分，存在于已建立的DNA小沟黏合剂苯甲腈[1,3-双（4'-ami基苯基）-三氮烯]中，该官能团通过功能化与嵌入的a啶发色团连接噻唑残基。预计该9-芳基吡啶可赋予杂化分子旋转自由度，并因此通过“经典”嵌入和较小的凹槽结合过程的组合促进与双链DNA的双功能相互作用。这些a啶-三氮烯组合毒素与组分分子片段的非共价DNA结合特性 已经通过使用小牛胸腺DNA和两个寡核苷酸[poly（dA-dT）] 2和[poly（dG-dC）] 2的荧光猝灭和热变性研究对它们进行了检查。另外，将这些a啶化合物的结合行为与原黄酮（3，6-二氨基ac啶）及其9-苯基衍生物的结合行为进行了比较。结果表明，杂化剂（i）比任何一种分子组分都具有更高的DNA亲和力，（ii）保留了母体双官能化的1,3-二
• Aromatic Nitro-group Displacement Reactions. Part 6.1 Structure of the Compound Formed by the Action of Morpholine on 2,2′,4,4′-Tetranitrobenzophenone
  作者：John H. Gorvin、Richard N. Sheppard

  DOI：10.1039/a806468g

  日期：——

  Morpholine has been shown to displace the two ortho-nitro groups in 2,2′,4,4′-tetranitrobenzophenone.

  吗啉已被证明可以置换 2,2',4,4'-四硝基二苯甲酮中的两个邻硝基。
• Gulland; Robinson, Journal of the Chemical Society, 1925, vol. 127, p. 1502
  作者：Gulland、Robinson

  DOI：——

  日期：——
• WO2006/95139
  申请人：——

  公开号：——

  公开（公告）日：——