4-[N-(2-imidazolinyl)]-1,2-phenylenediamine | 66639-63-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[N-(2-imidazolinyl)]-1,2-phenylenediamine
• 英文别名: 4-(2-imidazolinyl)-1,2-phenylenediamine；2-(3,4-diaminophenyl)-imidazoline；4-(4,5-dihydro-1H-imidazol-2-yl)benzene-1,2-diamine
• CAS: 66639-63-2
• 化学式: C₉H₁₂N₄
• 分子量: 176.221
• InChiKey: QVZGXYWTAPUJRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  76.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[N-(2-imidazolinyl)]-1,2-phenylenediamine 在 palladium on activated charcoal 盐酸 、 氢气 、 对苯醌 作用下， 以 乙醇 、 水 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 174.5h， 生成 1,2-bis[5-[5'-(2-imidazolinyl)-2'-benzimidazolyl]-2-benzimidazolyl]ethane
  参考文献：
  名称：

  Synthesis and DNA Interactions of Benzimidazole Dications Which Have Activity against Opportunistic Infections

  摘要：

  Considerable evidence now indicates that DNA is the receptor site for dicationic benzimidazole anti-opportunistic infections agents (Bell, C. A.; Dykstra, C. C.; Naiman, N. A. I.; Cory, M:.; Fairley, T. A.; Tidwell, R. R. Antimicrob. Agents Chemother. 1993, 37, 2668-2673. Tidwell, R. R.; Jones, S. K; Naiman, N. A.; Berger, I. C.; Brake, W. R.; Dykstra, C, C.; Hall, J. E. Antimicrob. Agents Chemother. 1993, 37, 1713-1716). To obtain additional information on benzimidazole-receptor complexes, the syntheses and DNA interactions of series of symmetric benzimidazole cations, linked by alkyl or alkenyl groups, have been evaluated. Biophysical techniques, thermal denaturation measurement (Delta T-m), kinetics, and circular dichroism (CD) have been used in conjunction with NMR and molecular modeling to evaluate the affinities, binding mode, and structure of complexes formed between these compounds and DNA. All of the compounds bind strongly to DNA samples with four or more consecutive AT base pairs, and they bind negligibly to GC rich DNA or to RNA. Spectral and kinetics characteristics of the benzimidazole complexes indicate that the compounds bind in the DNA minor groove at AT sequences. NMR and molecular modeling of the complex formed between an ethylene-linked benzimidazole derivative, 5, and the self-complementary oligomer d(GCGAATTCGC) have been used to establish structural details for the minor groove complex. These results have been used as a starting point for molecular mechanics calculations to refine the model of the minor groove-benzimidazole complex and to draw conclusions regarding the molecular basis for the effects of substituent changes on benzimidazole-DNA affinities.

  DOI：

  10.1021/jm9507946
• 作为产物：
  描述：

  4-氨基-3-硝基苯甲腈 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 144.0h， 生成 4-[N-(2-imidazolinyl)]-1,2-phenylenediamine
  参考文献：
  名称：

  New Amidino-benzimidazolyl Derivatives of Tylosin and Desmycosin.

  摘要：

  新型胍基苯并咪唑衍生物的抗生素酮霉素和去甲霉素是通过相应的胍基取代的邻苯二胺与酮霉素或去甲霉素在20-C醛基的反应制备的。该反应在无水乙醇中，在对苯醌的存在下进行。通过这种方法制备了：20-[5-(N-异丙胍基)-2-苯并咪唑基]酮霉素盐酸盐 9，20-[5-(2-咪唑啉基)-2-苯并咪唑基]酮霉素盐酸盐 10，20-[5-(N-吗啉基胍基)-2-苯并咪唑基]酮霉素盐酸盐 11，20-[5-(N-异丙胍基)-2-苯并咪唑基]去甲霉素盐酸盐 12，20-[5-(2-咪唑啉基)-2-苯并咪唑基]去甲霉素盐酸盐 13，20-[5-(N-吗啉基胍基)-2-苯并咪唑基]去甲霉素盐酸盐 14。对其抗微生物活性进行了测试，测试了一系列微生物。

  DOI：

  10.7164/antibiotics.55.308

文献信息

• New quinoline-arylamidine hybrids: Synthesis, DNA/RNA binding and antitumor activity
  作者：Luka Krstulović、Ivana Stolić、Marijana Jukić、Teuta Opačak-Bernardi、Kristina Starčević、Miroslav Bajić、Ljubica Glavaš-Obrovac

  DOI：10.1016/j.ejmech.2017.05.054

  日期：2017.9

  (groups I (2a-g) and II (5a-g)) or flexible -NH-CH2-CH2-O- (groups III (8a-g) and IV (10a-g)) linker were synthesized, and their DNA/RNA binding properties and cytotoxic activity were tested, against several human cancer lines. The compounds and their interaction with DNA and RNA were studied by UV–Vis and CD spectroscopy. The obtained results showed that the binding affinity of the investigated compounds

  通过刚性-O-（I组（2a-g）和II（5a-g））或柔性-NH-CH 2 -CH 2 - O-（第三组（8a-g）和第四组（10a-g））合成了连接子，并测试了其对几种人类癌症细胞系的DNA / RNA结合特性和细胞毒性活性。通过UV-Vis和CD光谱研究了这些化合物及其与DNA和RNA的相互作用。获得的结果表明，所研究化合物的结合亲和力随着能够与ds-多核苷酸形成氢键的基团的长度和数目的增加而成比例地增加。通过降低所研究化合物的结构刚度还可以实现结合的改善，新的杂合化合物优先结合ctDNA。对于大部分的DNA / RNA槽是占主导地位的结合位点，除了从基团的化合物II其在polyA-polyU中的插入是主要的结合模式。通过MTT测试对正常（MDCK1），癌（HeLa和CaCo2）和白血病细胞系（Raji和K462）的抗增殖作用进行了测试。所有研究的化合物的GI 50值范围从5到大于100×10
• Synthesis and in vitro activity of dicationic bis-benzimidazoles as a new class of anti-MRSA and anti-VRE agents
  作者：Laixing Hu、Maureen L. Kully、David W. Boykin、Norman Abood

  DOI：10.1016/j.bmcl.2009.01.075

  日期：2009.3

  class of novel bis-benzimidazole diamidine compounds have been synthesized and evaluated for in vitro antibacterial activities, including drug-resistant bacterial strains. Anti-MRSA and anti-VRE activities of the most potent compound 1 were more active than Vancomycin. The mechanism of action for this class of compounds appears to be different from existing antibiotics. Bis-benzimidazole diamidine compounds

  已经合成了一类新型的新型双苯并咪唑二am化合物，并对其体外抗菌活性进行了评估，包括耐药菌菌株。最有效的化合物1的抗MRSA和抗VRE活性比万古霉素更具活性。这类化合物的作用机理似乎不同于现有的抗生素。双-苯并咪唑二am化合物作为一类新的有效的抗MRSA和抗VRE剂具有潜力，需要进一步研究。
• Methods of treating retroviral infection and compounds useful therefor
  申请人：The University of North Carolina at Chapel Hill

  公开号：US05935982A1

  公开（公告）日：1999-08-10

  The present invention provides methods for treating retroviral infection and methods of treating HIV infection. The methods of the present invention include administering compounds of the general Formula I: ##STR1## wherein L, R.sub.1, R.sub.2, R.sub.3, R.sub.4 are defined herein.

  本发明提供了治疗逆转录病毒感染和治疗HIV感染的方法。本发明的方法包括给予一般式I的化合物：##STR1## 其中L、R1、R2、R3、R4的定义如本文所述。
• Design, synthesis, antitrypanosomal activity, DNA/RNA binding and in vitro ADME profiling of novel imidazoline-substituted 2-arylbenzimidazoles
  作者：Andrea Bistrović Popov、Luka Krstulović、Sanja Koštrun、Dubravko Jelić、Ana Bokulić、Marijana Radić Stojković、Iva Zonjić、Martin C. Taylor、John M. Kelly、Miroslav Bajić、Silvana Raić-Malić

  DOI：10.1016/j.ejmech.2020.112802

  日期：2020.12

  Novel imidazoline benzimidazole derivatives containing diversely substituted phenoxy moieties were synthesized with the aim of evaluating their antitrypanosomal activity, DNA/RNA binding affinity and in vitro ADME properties. The presence of the diethylaminoethyl subunit in 18a–18c led to enhanced antitrypanosomal potency, particularly for 18a and 18c, which contain unsubstituted and methoxy-substituted

  合成了含有不同取代的苯氧基部分的新型咪唑啉苯并咪唑衍生物，目的是评估它们的抗锥虫活性，DNA / RNA结合亲和力和体外ADME特性。在18a – 18c中二乙基氨基乙基亚基的存在增强了抗锥虫的效力，特别是对于18a和18c，它们含有未取代的和甲氧基取代的苯氧基部分。发现它们对非洲锥虫的功效比硝呋替莫要强2倍以上。荧光和CD光谱，热变性测定和计算分析表明偏爱18a – 18c富含AT的DNA及其次要沟结合方式。用较少的碱性和可离子化的含氮部分取代the基不能改善所研究化合物的膜渗透性。由于结构的多样化，这些化合物显示出一系列的物理化学特征，导致可变的体外ADME特性，为进一步优化生物学特性留有空间。
• Novel Cyano- and Amidino-Substituted Derivatives of Styryl-2-Benzimidazoles and Benzimidazo[1,2-<i>a</i>]quinolines. Synthesis, Photochemical Synthesis, DNA Binding, and Antitumor Evaluation, Part 3
  作者：Marijana Hranjec、Marijeta Kralj、Ivo Piantanida、Mirela Sedić、Lidija Šuman、Krešimir Pavelić、Grace Karminski-Zamola

  DOI：10.1021/jm070876h

  日期：2007.11.1

  Synthesis of novel cyano- and amidino-substituted styryl-2-benzimidazoles and benzimidazo[1,2-a]quinolines by condensation reactions and photochemical dehydrocyclization and dehydrohalogenation cyclization is described. Thermal denaturation experiments reveal that cyclic derivatives considerably stabilize DNA double helix, while the effect of their acyclic analogues is negligible. According to the

  描述了通过缩合反应和光化学脱氢环化和脱氢卤化环化反应合成新型氰基和a基取代的苯乙烯基-2-苯并咪唑和苯并咪唑并[1,2-a]喹啉。热变性实验表明，环状衍生物可显着稳定DNA双螺旋，而其无环类似物的作用则可忽略不计。根据环衍生物19相互作用的光谱研究，我们建议将苯并咪唑并[1,2-a]喹啉部分插入ct-DNA作为该化合物生物学相关作用的主要相互作用，而对于其无环衍生物11我们建议结合到DNA的小沟中。所有化合物均显示出明显的抗增殖作用。在所有无环衍生物中，吗啉代和氯取代的化合物9是活性最高的。所有环状化合物的效价都高2至10倍，这与其插入DNA中的特性有关。最具活性的咪唑基取代的化合物19抑制拓扑异构酶II，并诱导强烈的G2 / M细胞周期停滞，表明有丝分裂进程受到损害。其对结肠癌细胞的显着选择性促进了该化合物作为先导物的进一步发展。