N1-乙基-4-硝基苯-1,2-二胺 | 66668-41-5

• 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: N1-乙基-4-硝基苯-1,2-二胺
• 英文名称: N¹-ethyl-4-nitro-benzene-1,2-diamine
• 英文别名: N¹-ethyl-4-nitrobenzene-1,2-diamine；N1-ethyl-4-nitrobenzene-1,2-diamine；2-amino-N-ethyl-4-nitro-aniline；2-ethylamino-5-nitroaniline；N¹-ethyl-4-nitro-o-phenylenediamine；N¹-Aethyl-4-nitro-o-phenylendiamin；1-N-ethyl-4-nitrobenzene-1,2-diamine
• CAS: 66668-41-5
• 化学式: C₈H₁₁N₃O₂
• 分子量: 181.194
• InChiKey: PNDJSMFFLOHKTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  83.9
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2921590090

反应信息

• 作为反应物：
  描述：

  N1-乙基-4-硝基苯-1,2-二胺 在 10percent Pd/C 氢气 、 溶剂黄146 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 4-(5-amino-1-ethyl-1H-benzoimidazol-2-ylmethyl)-benzonitrile
  参考文献：
  名称：

  Structure-Based Design of Novel Potent Nonpeptide Thrombin Inhibitors

  摘要：

  The clinical syndromes of thromboembolism are evoked by an excessive stimulation of the coagulation cascade. In this context, the serine protease thrombin plays a key role. Considerable efforts have therefore been devoted to the discovery of safe, orally active inhibitors of this enzyme. On the basis of the X-ray crystal structure of the peptidelike thrombin inhibitor NAPAP complexed with bovine thrombin, we have designed a new structural class of nonpeptidic inhibitors employing a 1,2,5-trisubstituted benzimidazole as the central scaffold. Supported by a series of X-ray structure analyses, we optimized the activity of these compounds. Thrombin inhibition in the lower nanomolar range could be achieved although the binding energy mainly results from nonpolar, hydrophobic interactions. To improve in vivo potency, we increased the overall hydrophilicity of the molecules by introducing carboxylate groups. The very polar compound 24 (BIBR 953) exhibited the most favorable activity profile in vivo. This zwitterionic molecule was converted into the double-prodrug 31 (BIBR 1048), which showed strong oral activity in different animal species. On the basis of these results, 31 was chosen for clinical development.

  DOI：

  10.1021/jm0109513
• 作为产物：
  描述：

  2,4-二硝基-N-乙基苯胺 在 镍 、 一水合肼 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 6.0h， 以98%的产率得到N1-乙基-4-硝基苯-1,2-二胺
  参考文献：
  名称：

  用水合肼部分还原二硝基芳烃为硝基苯胺

  摘要：

  在阮内镍催化剂的存在下，在乙醇/1,2-二氯乙烷溶剂混合物中，含有羟基和胺基等取代基的二硝基芳烃可以方便地用 3 摩尔当量的水合肼还原得到产物，其中两个硝基之一被还原为氨基。部分还原产物的收率良好。在类似条件下，硝基 o,p 位的烷氧基取代基被肼基取代，得到 2,4-二硝基苯肼作为主要产物。描述还原反应的细节。

  DOI：

  10.1246/bcsj.56.3159

文献信息

• [EN] DIAMINO-PYRIMIDINES AND THEIR USE AS ANGIOGENESIS INHIBITORS<br/>[FR] DIAMINO-PYRIMIDINES ET LEURS UTILISATIONS EN TANT QU'INHIBITEURS DE L'ANGIOGENESE
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2003074515A1

  公开（公告）日：2003-09-12

  Benzimidazole derivatives of formula (I) , which are useful as TIE-2 and/or VEGFR-2 inhibitors are described herein. The described invention also includes methods of making such benzimidazole derivatives as well as methods of using the same in the treatment of hyperproliferative diseases. (I)

  本发明描述了公式(I)的苯并咪唑衍生物，它们作为TIE-2和/或VEGFR-2抑制剂是有用的。所描述的发明还包括制造这样的苯并咪唑衍生物的方法，以及使用它们在治疗增生性疾病中的方法。
• Partial Reduction of Dinitroarenes to Nitroanilines with Hydrazine Hydrate
  作者：Nagaraj R. Ayyangar、Uttam R. Kalkote、Ananda G. Lugade、Pandurang V. Nikrad、Vasant K. Sharma

  DOI：10.1246/bcsj.56.3159

  日期：1983.10

  such as hydroxyl and amine groups could be conveniently reduced with 3 molar equivalents of hydrazine hydrate in presence of Raney nickel catalyst in ethanol/1,2-dichloroethane solvent mixture to give a product wherein one of the two nitro groups was reduced to the amino group. The yields of the partial reduction products are good. Under similar conditions alkoxyl substituents in the o,p-position to the

  在阮内镍催化剂的存在下，在乙醇/1,2-二氯乙烷溶剂混合物中，含有羟基和胺基等取代基的二硝基芳烃可以方便地用 3 摩尔当量的水合肼还原得到产物，其中两个硝基之一被还原为氨基。部分还原产物的收率良好。在类似条件下，硝基 o,p 位的烷氧基取代基被肼基取代，得到 2,4-二硝基苯肼作为主要产物。描述还原反应的细节。
• BICYCLICALLY SUBSTITUTED URACILS AND THE USE THEREOF
  申请人：BAYER PHARMA AKTIENGESELLSCHAFT

  公开号：US20150148340A1

  公开（公告）日：2015-05-28

  The present application relates to novel bicyclically substituted uracil derivatives, to processes for preparation thereof, to the use thereof alone or in combinations for treatment and/or prophylaxis of diseases, and to the use thereof for production of medicaments for treatment and/or prophylaxis of diseases.

  本申请涉及新颖的双环替代尿嘧啶衍生物，其制备方法，单独或组合使用以治疗和/或预防疾病，以及用于生产治疗和/或预防疾病药物的用途。
• [EN] ARYL AND HETEROARYL ETHER COMPOUNDS AS ROR GAMMA MODULATORS<br/>[FR] COMPOSÉS ÉTHER D'ARYLE ET ÉTHER D'HÉTÉROARYLE EN TANT QUE MODULATEURS DE ROR GAMMA
  申请人：GLENMARK PHARMACEUTICALS SA

  公开号：WO2015159233A1

  公开（公告）日：2015-10-22

  The present disclosure is directed to compounds of formula (I) and pharmaceutically acceptable salts thereof, wherein Ring A, Ring B, R, R2, R3, n, and p are as defined herein, which are active as modulators of retinoid-related orphan receptor gamma t (RORγt). These compounds prevent, inhibit, or suppress the action of RORγt and are therefore useful in the treatment of RORγt mediated diseases, disorders, syndromes or conditions such as, e.g., pain, inflammation, COPD, asthma, rheumatoid arthritis, colitis, multiple sclerosis, psoriasis, neurodegenerative diseases and cancer.

  本公开涉及式(I)的化合物及其药用盐，其中环A、环B、R、R2、R3、n和p如本文所定义，这些化合物作为视黄酸相关孤儿受体γt（RORγt）的调节剂具有活性。这些化合物可以预防、抑制或抑制RORγt的作用，因此在治疗RORγt介导的疾病、疾病、综合症或症状方面具有用处，例如疼痛、炎症、慢性阻塞性肺病（COPD）、哮喘、类风湿性关节炎、结肠炎、多发性硬化、牛皮癣、神经退行性疾病和癌症。
• Diamino-pyrimidines and their use as angiogenesis inhibitors
  申请人：Chamberlain Dawes Stanley

  公开号：US20050234083A1

  公开（公告）日：2005-10-20

  Benzimidazole derivatives, which are useful as TIE-2 and/or VEGFR-2 inhibitors are described herein. The described invention also includes methods of making such benzimidazole derivatives as well as methods of using the same in the treatment of hyperproliferative diseases.

  本文描述了作为TIE-2和/或VEGFR-2抑制剂有用的苯并咪唑衍生物。所述发明还包括制备这种苯并咪唑衍生物的方法，以及将其用于治疗过度增殖性疾病的方法。