(9ci)-1-甲基-6-硝基-1H-苯并咪唑 | 5381-79-3

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: (9ci)-1-甲基-6-硝基-1H-苯并咪唑
• 中文别名: 1-甲基-6-硝基苯并咪唑
• 英文名称: 1-methyl-6-nitro-1H-benzoimidazole
• 英文别名: 1-methyl-6-nitro-1H-benzo[d]imidazole；1-methyl-6-nitro-1H-benzimidazole；1-methyl-6-nitrobenzimidazole；6-nitro-1-methylbenzimidazole；1-methyl-6-nitro-1H-benzoimidazole；1-Methyl-6-nitro-1H-benzimidazol
• CAS: 5381-79-3
• 化学式: C₈H₇N₃O₂
• mdl: MFCD00962814
• 分子量: 177.162
• InChiKey: HVZQEZDKCBTTTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  63.6
• 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：

  (9ci)-1-甲基-6-硝基-1H-苯并咪唑 在 氢气 、 镍 作用下， 以 乙醇 为溶剂， 生成 1-甲基-1H-苯并咪唑-6-胺
  参考文献：
  名称：

  溶液中和固态中氨基苯并咪唑的 13C 和 15N NMR 光谱

  摘要：

  已记录了六种 C-氨基苯并咪唑的 13C [六重二甲基亚砜 (DMSO-d6)、六甲基-磷酰胺 (HMPA)-d18 和固态] 和 15N（固态）NMR 光谱。已确定 4(7)-氨基苯并咪唑和 5(6)-氨基苯并咪唑的互变异构现象，并与 B3LYP/6-311 + + G(d,p) 计算进行比较，证实了 4-氨基互变异构体的明显优势和轻微的偏好为 6-氨基互变异构体。GIAO 计算的绝对屏蔽与实验化学位移比较好。版权所有 © 2008 John Wiley & Sons, Ltd.

  DOI：

  10.1002/mrc.2357
• 作为产物：
  描述：

  α-chloro-β-hydroxy-isovaleric acid ethyl ester 在 硫酸 作用下， 生成 (9ci)-1-甲基-6-硝基-1H-苯并咪唑
  参考文献：
  名称：

  Leandri et al., Gazzetta Chimica Italiana, 1955, vol. 85, p. 769,788

  摘要：

  DOI：

文献信息

• [EN] 5-SULFAMOYL-2-HYDROXYBENZAMIDE DERIVATIVES<br/>[FR] DÉRIVÉS DE 5-SULFAMOYL-2-HYDROXYBENZAMIDE
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2017153952A1

  公开（公告）日：2017-09-14

  The invention is directed to substituted salicylamide derivatives. Specifically, the invention is directed to compounds according to Formula (I): wherein R, R1 and R2 are as defined herein, or a pharmaceutically acceptable salt thereof. The compounds of the invention are inhibitors of CD73 and can be useful in the treatment of cancer, pre-cancerous syndromes and diseases associated with CD73 inhibition, such as AIDS, the treatment of HIV, autoimmune diseases, infections, atherosclerosis, and ischemia–reperfusion injury. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting CD73 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

  本发明涉及取代水杨酰胺衍生物。具体而言，本发明涉及根据公式(I)的化合物：其中R、R1和R2如本文所述，或其药用可接受的盐。本发明的化合物是CD73的抑制剂，可用于治疗癌症、前癌症综合症以及与CD73抑制相关的疾病，例如艾滋病、治疗HIV、自身免疫疾病、感染、动脉粥样硬化和缺血再灌注损伤。因此，本发明进一步涉及包含本发明化合物的药物组合物。本发明还进一步涉及使用本发明化合物或包含本发明化合物的药物组合物来抑制CD73活性和治疗与之相关的疾病的方法。
• Novel anthranilamide pyridinureas as VEGF receptor kinase inhibitors
  申请人：Schering Aktiengesellschaft

  公开号：EP1657241A1

  公开（公告）日：2006-05-17

  The invention relates to novel anthranilamide pyridinureas as VEGF receptor kinase inhibitors, their production and use as pharmaceutical agents for treating diseases that are triggered by persistent angiogenesis.

  这项发明涉及新型蒽酰胺吡啶脲作为VEGF受体激酶抑制剂，它们的生产和用作治疗由持续血管生成引发的疾病的药物代理。
• The reaction of benzimidazolium derivatives with superoxide
  作者：Kazuhiro Nagata、Takashi Itoh、Mamiko Okada、Akio Ohsawa

  DOI：10.1016/0040-4020(96)00313-4

  日期：1996.5

  benzimidazolium salts, which have an electron deficient imidazolium ring and a carbamate moiety, were allowed to react with superoxide to give ring-opened products and 1-methylbenzimidazoles. The products ratio varied on the change of the counter cation species of superoxide. When 1,1′,3,3′ - tetramethyl- 2,2′-bibenzimidazolium salt reacted with KO2, chemiluminescence was observed which did not occur

  使具有缺电子的咪唑环和氨基甲酸酯部分的1-乙氧羰基-3-甲基苯并咪唑鎓盐与超氧化物反应，得到开环产物和1-甲基苯并咪唑。产物比率随超氧化物的反阳离子种类的变化而变化。当1,1'，3,3'-四甲基-2,2'-联苯并咪唑鎓盐与KO 2反应时，观察到化学发光，该化学发光未通过使用KOH或H 2 O 2作为试剂而发生。
• Reactions of 1-methylbenzimidazole derivatives with m-chloroperoxybenzoic acid
  作者：Toyo Kaiya、Shinsuke Aoyama、Kohfuku Kohda

  DOI：10.1016/s0960-894x(98)00082-1

  日期：1998.3

  Oxidation of seven 1-methylbenzimidazole (MBI) derivatives (with pKa's ranging from 1.6 to 6.0) was carried out with m-chloroperoxybenzoic acid and structures of the products formed were identified. (Condensed benzene moiety-hydroxylated)-2-(m-chlorobenzyloxy)-MBIs and 2-oxo-MBIs were obtained from MBIs with pKa's of more than 5.6 and about 3.3, respectively.

  用间氯过氧苯甲酸氧化了七个1-甲基苯并咪唑（MBI）衍生物（pKa范围为1.6至6.0），并鉴定了形成的产物的结构。从具有pKa分别大于5.6和约3.3的MBI中获得（缩合的苯部分-羟基化）-2-（间氯苄氧基）-MBI和2-氧代-MBI。
• Vicarious Nucleophilic C-Amination of Nitrobenzene and 5- and 6-Nitro-1-methylbenzimidazoles
  作者：I. A. Titova、T. I. Vakul'skaya、L. I. Larina、M. I. Mizandrontsev、V. A. Volkov、G. V. Dolgushin、V. A. Lopyrev

  DOI：10.1007/s11178-005-0339-z

  日期：2005.9

  Vicarious nucleophilic C-amination of nitrobenzene, 1-methyl-5-nitrobenzimidazole, and 1-methyl-6-nitrobenzimidazole in superbasic medium (potassium tert-butoxide-dimethyl sulfoxide) gave the corresponding amino-substituted derivatives. The yield of the amination product of 1-methyl-5-nitrobenzimidazole considerably increased in the presence of CuCl. ESR monitoring of these reactions revealed formation of primary radical anions from the substrates. Possible reaction mechanisms are discussed.

  在超碱性介质（氢氧化钾-二甲基亚砜）中，对硝基苯、1-甲基-5-硝基苯并咪唑和1-甲基-6-硝基苯并咪唑进行了间接的亲核C-氨基化，得到了相应的氨基取代衍生物。在CuCl存在的情况下，1-甲基-5-硝基苯并咪唑的氨基化产物的产率显著提高。对这些反应的电子自旋共振（ESR）监测显示，底物形成了初级自由基阴离子。讨论了可能的反应机制。