1,2-dimethyl-1H-naphtho[2,3-d]imidazole-4,9-dione | 4572-59-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,2-dimethyl-1H-naphtho[2,3-d]imidazole-4,9-dione
• 英文别名: 1,2-Dimethyl-naphth<2.3-d>imidazoldion-(4,9)；1h-Naphth[2,3-d]imidazole-4,9-dione, 1,2-dimethyl-；2,3-dimethylbenzo[f]benzimidazole-4,9-dione
• CAS: 4572-59-2
• 化学式: C₁₃H₁₀N₂O₂
• 分子量: 226.235
• InChiKey: DSABGXKNIWFVGX-UHFFFAOYSA-N

物化性质

• 熔点：
  248 °C
• 沸点：
  469.9±14.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  52
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1,2-dimethyl-1H-naphtho[2,3-d]imidazole-4,9-dione 生成 2,3-Dimethyl-5-nitrobenzo[f]benzimidazole-4,9-dione
  参考文献：
  名称：

  GREEN-BUCKLEY G.; GRIFFITHS J., J. CHEM. SOC. PERKIN TRANS., PART 1, 1979, NO 3, 702-707

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(3-氯-1,4-二氢-1,4-二氧代-2-萘基)乙酰胺 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 48.0h， 生成 1,2-dimethyl-1H-naphtho[2,3-d]imidazole-4,9-dione
  参考文献：
  名称：

  咪唑基1,4-萘醌的合成及生物活性

  摘要：

  设计和开发具有多重耐药性（MDR）感染的药物的兴趣日益增长。我们报告的合成，咪唑基的1，4-萘醌（I-1至I-4； 1-烷基-2-甲基-1 H-萘[2,3 - d ]咪唑-4的合成，抗菌和抗真菌活性，9-二酮（烷基=甲基至丁基））及其前体（B-3 ; N-（3-氯-1，-二氧代-1,4-二氢萘-2-基）乙酰胺）和A-1至A -4 ; N-（3-（烷基氨基）-1，4-二氧代-1，4-二氢萘-2-基）乙酰胺（烷基＝甲基至丁基）。B-3，A-1至A-3的晶体结构通过单晶X射线衍射实验获得I-1和I-2至I-4。利用密度泛函理论进一步表征了电子结构和电荷分布。这些衍生物中的七个对少数几种选定的细菌菌株（革兰氏阳性和革兰氏阴性）显示出广泛的抗菌活性。正如所证明的，B-2和B-3对细菌分离株的MIC值为8–64μgml -1，而对致病性酵母菌白色念珠菌的MIC值在128–256μgml -1的范围内。

  DOI：

  10.1039/c9nj04339j

文献信息

• Antimalarial <i>N</i>¹,<i>N</i>³-Dialkyldioxonaphthoimidazoliums: Synthesis, Biological Activity, and Structure–activity Relationships
  作者：Stephen Ahenkorah、Dina Coertzen、Jie Xin Tong、Kevin Fridianto、Sergio Wittlin、Lyn-Marie Birkholtz、Kevin S. W. Tan、Yulin Lam、Mei-Lin Go、Richard K. Haynes

  DOI：10.1021/acsmedchemlett.9b00457

  日期：2020.1.9

  Here we report the nanomolar potencies of N 1,N 3-dialkyldioxonaphthoimidazoliums against asexual forms of sensitive and resistant Plasmodium falciparum. Activity was dependent on the presence of the fused quinone-imidazolium entity and lipophilicity imparted by the N1/N3 alkyl residues on the scaffold. Gametocytocidal activity was also detected, with most members active at IC50 < 1 μM. A representative

  在这里，我们报告N 1，N 3-二烷基二氧杂萘甲并咪唑类对敏感和耐药性恶性疟原虫无性形式的纳摩尔浓度。活性取决于稠合的醌-咪唑鎓实体的存在和由支架上的N1 / N3烷基残基赋予的亲脂性。还检测到杀细胞杀灭活性，大多数成员在IC50 <1μM时有活性。具有良好溶解性，有限的PAMPA渗透性和微粒体稳定性的代表性类似物在恶性疟原虫的人源化小鼠模型上显示出口服功效。
• Use of tricyclic derivatives of 1,4-dihydro-1,4-dioxo-1H-naphthalene, novel compounds obtained and their application in theraphy
  申请人：Laboratoire Innothera

  公开号：US06262095B1

  公开（公告）日：2001-07-17

  The invention concerns the therapeutic use of tricyclic salts and their pharmaceutically acceptable salts having the general formula: in which: A is either a sulfur atom, an oxygen atom, or an R3N radical where R3 is a hydrogen atom, a C1-C5 alkyl radical, or a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring. R1 is either a C1-C5 alkyl radical, or an R4NH radical where R4 is a hydrogen atom, a C1-C5 alkyl radical, or a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring, or an aromatic ring that may or may not be substituted by one or more acceptor or donor groups, or a heteroaromatic ring having one or more heteroatoms, which may or may not be substituted by acceptor or donor groups. R2 is a hydrogen atom, halogen atom, a C1-C5 alkyl radical, an oxygen atom that may or may not be substituted by a C1-C5 alkyl radical, or an NR5R5, radical where R5 and R5, are, independently of each other, a hydrogen atom, an oxygen atom or monovalent C1-C5 organic radicals.

  本发明涉及三环盐及其药学上可接受的盐的治疗用途，其一般式如下：其中：A是硫原子、氧原子或R3N基团，其中R3是氢原子、C1-C5烷基、取代或未取代的芳香环或取代或未取代的杂环。R1是C1-C5烷基，或R4NH基团，其中R4是氢原子、C1-C5烷基、取代或未取代的芳香环或取代或未取代的杂环，或可能被一个或多个受体或给体基团取代或未取代的芳香环，或具有一个或多个杂原子的杂环，该杂原子可能被受体或给体基团取代或未取代。R2是氢原子、卤原子、C1-C5烷基、可能被C1-C5烷基取代或未取代的氧原子，或NR5R5基团，其中R5和R5'分别是氢原子、氧原子或一价的C1-C5有机基团。
• Small molecule inhibitors of USP1 deubiquitinating enzyme activity
  申请人：Dana-Farber Cancer Institute, Inc.

  公开号：US10653676B2

  公开（公告）日：2020-05-19

  Provided are small molecule inhibitors of ubiquitin specific protease 1 (USP1) activity and methods for their use in treating and characterizing cancers. The small molecule USP1 inhibitors of the invention are particularly useful in the treatment of cancers that are resistant to DNA cross-linking agents.

  本发明提供了泛素特异性蛋白酶 1（USP1）活性的小分子抑制剂及其用于治疗和鉴定癌症的方法。本发明的小分子 USP1 抑制剂尤其适用于治疗对 DNA 交联剂具有抗药性的癌症。
• Oxidation products of fused 2-hetarylimidazole derivatives
  作者：A. A. Aleksandrov、A. P. Savost’yanov、M. M. El’chaninov、G. V. Salamatina

  DOI：10.1134/s1070363211080226

  日期：2011.8

  Oxidation of 5-(1-methyl-1H-benzimidazol-2-yl)thiophene-, and -selenophene-2-carbaldehydes with potassium dichromate in 20% aqueous sulfuric acid afforded the corresponding carboxylic acids. Analogous reaction with 5-(1-methyl-1H-benzimidazol-2-yl)furan-2-carbaldehyde led to the formation of 1-methyl-1H-benzimidazole as a result of decarboxylation of the primary oxidation product and subsequent decomposition of the furan ring. Probable factors responsible for instability of 5-(1H-benzimidazol-2-yl)-hetarene-2-carboxylic acids were considered. The oxidation of 2-furylnaphtho[2,3-d]- and 2-hetarylphenanthro-[9,10-d]imidazoles gave, respectively, an anthraquinone analog and 6,7-quinones. pi-Electron-rich heterocycles in 2-furyl- and 2-pyrrolylphenanthro[9,10-d]imidazoles were oxidized completely, being replaced by hydrogen.
• Preparation and in vitro antiprotozoan activity of new naphthoimidazolediones
  作者：P Vanelle、S Donini、J Maldonado、M.P. Crozet、F Delmas、M Gasquet、P Timon-David

  DOI：10.1016/s0223-5234(97)84015-9

  日期：1997.6

  The original compound bearing the coplanar quinone and imidazole systems, 2-chloromethyl-4,9-dihydro-1-methyl-1H-naphtho[2,3-d]imidazol-4,9-dione reacted with various nitronate anions to afford, in moderate to good yields, new naphthoimidazolediones bearing a trisubstituted ethylenic double bond at the 2-position. These compounds were evaluated as potential antiprotozoan agents. Some derivatives were found to have a significant activity, but the naphthoquinone was found to be a less efficient pharmacophore than the nitro group.