(9ci)-1-羟基-2-甲基-1H-苯并咪唑,3-氧化物 | 15966-52-6

• 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-羟基-2-甲基-1H-苯并咪唑,3-氧化物
• 英文名称: 2-methyl-3-oxy-benzoimidazol-1-ol
• 英文别名: 1-Hydroxy-2-Methylbenzimidazole-3-Oxide；1-Hydroxy-2-methyl-1H-benzimidazol-3-oxid；1-Hydroxy-2-methyl-benzimidazol-3-oxid；1-Hydroxy-2-methylbenzimidazol-3-oxid；2-Methyl-1-hydroxy-3-oxobenzimidazol；1-Hydroxy-2-methyl-3-oxidobenzimidazol-3-ium
• CAS: 15966-52-6
• 化学式: C₈H₈N₂O₂
• 分子量: 164.164
• InChiKey: XSOHMVMLXANIAU-UHFFFAOYSA-N

物化性质

• 熔点：
  195-196 °C
• 沸点：
  411.5±28.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  50.6
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1-碘戊烷 、 (9ci)-1-羟基-2-甲基-1H-苯并咪唑,3-氧化物 在 哌啶 作用下， 以 二甲基亚砜 为溶剂， 以52%的产率得到2-Methyl-1-oxido-3-pentoxybenzimidazol-1-ium
  参考文献：
  名称：

  2H-Benzimidazole 1,3-Dioxide Derivatives:  A New Family of Water-Soluble Anti-Trypanosomatid Agents

  摘要：

  Three series of benzimidazole N-oxide derivatives were developed and were examined for their activity against trypanosomatid parasites (Trypanosoma cruzi and Leishmania spp.). 2H-Benzimidazole 1,3-dioxides displayed remarkable in vitro activities against both parasites, with derivatives 28, 29, and 32 being the most potent (IC50 < 5 mu M) against the epimastigote form of T. cruzi and 28, 33, and 35 the most potent against the promastigote form of Leishmania spp. Unspecific cytotoxicity was evaluated using murine macrophages, and derivative 33 was not toxic at a concentration 30 times that of its IC50 against T. cruzi that was completely toxic for Leishmania spp., implying that the series of 2H-benzimidazole 1,3-dioxides is selective toward both trypanosomatid parasites. Derivatives 33 and 35 were submitted to an in vivo assay using an acute model of Chagas' disease and a short-term treatment (30 mg/kg/day orally administrated as aqueous solution, during 10 days). While in the control (untreated) and Benznidazole (50 mg/kg/day) groups survival fraction was 60.0% and 87.5%, respectively, none of the animals treated with derivatives 33 and 35 died. From the preliminary structure-activity relationship studies reduction potential and electrophilicity were found relevant to anti-T. cruzi activity. Active compounds are better electrophiles and more easily reduced than inactive ones.

  DOI：

  10.1021/jm0600343
• 作为产物：
  描述：

  苯并呋咱 、 硝基乙烷 以64%的产率得到
  参考文献：
  名称：

  LATHAM D. W. S.; METH-COHN O.; SUSCHITZKY H.; HERBERT J. A. L., J. CHEM. SOC. PERKIN TRANS., PART 1 , 1977, NO 5, 470-478

  摘要：

  DOI：

文献信息

• Quinoxaline derivatives
  申请人：Research Corporation

  公开号：US04343942A1

  公开（公告）日：1982-08-10

  The synthesis of quinoxaline and benzimidazole-N-oxides and of ester and amide derivatives of 3-hydroxy-2-quinoxalinecarboxylic acid by a novel process consisting of the reaction between a benzofuroxan and an activated methylene-containing compound under basic conditions.

  喹啉和苯并咪唑-N-氧化物的合成，以及3-羟基-2-喹啉羧酸的酯和酰胺衍生物的合成，通过一种新颖的过程实现，该过程包括在碱性条件下对苯并呋喃酰胺和含活性亚甲基的化合物进行反应。
• Process, modified rubbers and rubber compositions
  申请人：Bridgestone/Firestone, Inc.

  公开号：US05001171A1

  公开（公告）日：1991-03-19

  It now has been found that uncured modified rubber compositions comprising mixtures of elastomers and a reinforcing filler can be prepared having improved properties. More particularly, such uncured modified rubber compositions can be prepared by a process which comprises the steps of (A) preparing a first mixture comprising an elastomer, at least one reinforcing filler and at least one chemical agent capable of promoting the formation of filler-elastomer linkages; (B) preparing a second mixture comprising (i) an elastomer, at least one reinforcing filler and at least one chemical agent capable of promoting the formation of filler-elastomer linkages, wherein at least one of the elastomer, filler or chemical agent in the second mixture is different from the elastomer, filler or chemical agent in the first mixture; or (ii) an elastomer and at least one reinforcing filler; or (iii) at least one reinforcing filler and at least one chemical agent capable of promoting the formation of filler-elastomer linkages; or (iv) an elastomer and at least one chemical agent capable of promoting the formation of filler-elastomer linkages; and (C) blending the first and second mixtures to form a third mixture. Examples of such useful chemical agents include aromatic furazan oxides, heterocyclic di-N-oxides, 1-hydroxy-benzimidazole-3-oxide compounds, 1,3-dihydroxy-benzimidazolinone compounds, and aromatic nitroso compounds. The invention also includes filled vulcanizates prepared by vulcanizing the uncured modified rubber compositions prepared in accordance with the above method. Rubber articles and portions thereof made from such vulcanizates such as tires, hoses, belts, treads, sidewalls and the like are also within the scope of the present invention as well as methods of reducing the rolling resistance of tires.

  现在已经发现，由弹性体和增强填料混合而成的未固化改性橡胶组合物可以制备出具有改进性能的材料。具体而言，这种未固化改性橡胶组合物可以通过以下步骤制备：（A）制备第一混合物，其中包括弹性体、至少一种增强填料和至少一种能促进填料-弹性体连接形成的化学剂；（B）制备第二混合物，其中包括（i）弹性体、至少一种增强填料和至少一种能促进填料-弹性体连接形成的化学剂，其中第二混合物中的至少一种弹性体、填料或化学剂与第一混合物中的弹性体、填料或化学剂不同；或（ii）弹性体和至少一种增强填料；或（iii）至少一种增强填料和至少一种能促进填料-弹性体连接形成的化学剂；或（iv）弹性体和至少一种能促进填料-弹性体连接形成的化学剂；（C）将第一混合物和第二混合物混合成第三混合物。这些有用的化学剂的例子包括芳香基呋喃氧化物、杂环二氧化物、1-羟基苯并咪唑-3-氧化物化合物、1,3-二羟基苯并咪唑啉酮化合物和芳香基亚硝酰化合物。该发明还包括通过硫化按照上述方法制备的未固化改性橡胶组合物的填充硫化胶以及由此制成的橡胶制品和部件，例如轮胎、软管、传动带、胎面、侧壁等，以及降低轮胎滚动阻力的方法。
• Rubber compositions modified with hydroxy-benz-imidazole oxides
  申请人：The Firestone Tire & Rubber Company

  公开号：US04762870A1

  公开（公告）日：1988-08-09

  It now has been found that the properties of rubber compositions comprising rubbers having an unsaturated carbon chain can be improved by including therein, a minor property-improving amount of at least one hydroxy-benzimidazole oxide compound of the formula ##STR1## wherein R is hydrogen, or a halogen, hydroxyl, lower acyl, lower hydrocarbyl, lower hydrocarbyloxy, lower hydrocarbylthio, carboxyl, cyano, amino, amide or --C(O)-- lower hydrocarbyl group, and R' is hydrogen, or a lower hydrocarbyl, lower hydrocarbyl amide, carboxamide carboxy acid, carboxy ester, or aryl group. When vulcanizates are prepared from such rubber compositions containing one or more fillers, the vulcanizates exhibit reduced low strain hysteresis and a high electrical resistivity. In another aspect of the invention, a filled vulcanizate made by vulcanizing uncured compositions of the type described above and containing a filler, particularly carbon black, is improved in filler interaction, hysteresis, modulus, compression set and resiliency. Rubber articles and portions thereof such as tires, hoses, springs, belts, treads, sidewalls and the like can be made utilizing the improved filled vulcanizates of the invention.

  现在已经发现，包括具有不饱和碳链的橡胶在内的橡胶组合物的性能可以通过包含至少一种羟基苯并咪唑氧化物化合物的少量改性剂来改善，该化合物的化学式为##STR1##其中R是氢，卤素，羟基，较低的酰基，较低的烃基，较低的烃氧基，较低的烃硫基，羧基，氰基，氨基，酰胺或--C（O）--较低的烃基，而R'是氢，或较低的烃基，较低的烃酰胺，羧酰胺羧酸，羧酸酯或芳基。当制备含有一种或多种填料的这种橡胶组合物的硫化胶时，硫化胶表现出较低的低应变迟滞和较高的电阻率。在发明的另一个方面中，通过硫化上述未固化组合物并含有填料，特别是碳黑，可以改善填料相互作用、迟滞、模量、压缩回弹性等方面的填充硫化胶。利用本发明的改进型填充硫化胶可以制造橡胶制品和其部分，如轮胎、软管、弹簧、皮带、胎面、侧壁等。
• Novel process for the synthesis of quinoxaline and benzimidazole-N-oxides
  申请人：Research Corporation

  公开号：US04866175A1

  公开（公告）日：1989-09-12

  The synthesis of quinoxaline and benzimidazole-N-oxides and of ester amd amide derivatives of 3-hydroxy-2-quinoxalinecarboxylic acid by a movel process consisting of the reaction between a benzofuroxan and an activated methylene-containing compound under basic conditions.

  使用一种新型工艺，通过苯并呋喃氧化物和含有活性亚甲基的化合物在碱性条件下的反应，合成了喹喹啉和苯并咪唑-N-氧化物以及3-羟基-2-喹啉羧酸的酯和酰胺衍生物。
• US4343942A
  申请人：——

  公开号：US4343942A

  公开（公告）日：1982-08-10