2,5-二甲基-4-硝基苯并咪唑 | 90349-14-7

• 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: 2,5-二甲基-4-硝基苯并咪唑
• 中文别名: 2-(5-异恶唑基)-4-甲基苯酚
• 英文名称: 2,5-Dimethyl-4-nitrobenzimidazole
• 英文别名: 2,5-dimethyl-4-nitro-1H-benzimidazole
• CAS: 90349-14-7
• 化学式: C₉H₉N₃O₂
• mdl: MFCD00674200
• 分子量: 191.189
• InChiKey: ZDKNXWAFKNYXFI-UHFFFAOYSA-N

物化性质

• 熔点：
  173-175 °C
• 沸点：
  439.4±25.0 °C(Predicted)
• 密度：
  1.370±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  74.5
• 氢给体数：
  1
• 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：

  2,5-二甲基-4-硝基苯并咪唑 在 10percent Pd/C 氢气 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 100.0h， 生成 9-[4-(2,5-dimethyl-4-amino-1H-benzimidazol-1-yl)butyl]-N-(2,2,2-trifluoroethyl)-9H-fluorene-9-carboxamide
  参考文献：
  名称：

  A Novel Series of Highly Potent Benzimidazole-Based Microsomal Triglyceride Transfer Protein Inhibitors

  摘要：

  A series of benzimidazole-based analogues of the potent MTP inhibitor EMS-201038 were discovered. Incorporation of an unsubstituted benzimidazole moiety in place of a piperidine group afforded potent inhibitors of MTP in vitro which were weakly active in vivo. Appropriate substitution on the benzimidazole ring, especially with small alkyl groups, led to dramatic increases in potency, both in a cellular assay of apoB secretion and especially in animal models of cholesterol lowering. The most potent in this series, 3g (BMS-212122), was significantly more potent than EMS-201038 in reducing plasma lipids (cholesterol, VLDL/LDL, TG) in both hamsters and cynomolgus monkeys.

  DOI：

  10.1021/jm000494a
• 作为产物：
  描述：

  5-Methyl-benzo[1,2,5]selenadiazole 在 盐酸 、 硫酸 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 2,5-二甲基-4-硝基苯并咪唑
  参考文献：
  名称：

  A Novel Series of Highly Potent Benzimidazole-Based Microsomal Triglyceride Transfer Protein Inhibitors

  摘要：

  A series of benzimidazole-based analogues of the potent MTP inhibitor EMS-201038 were discovered. Incorporation of an unsubstituted benzimidazole moiety in place of a piperidine group afforded potent inhibitors of MTP in vitro which were weakly active in vivo. Appropriate substitution on the benzimidazole ring, especially with small alkyl groups, led to dramatic increases in potency, both in a cellular assay of apoB secretion and especially in animal models of cholesterol lowering. The most potent in this series, 3g (BMS-212122), was significantly more potent than EMS-201038 in reducing plasma lipids (cholesterol, VLDL/LDL, TG) in both hamsters and cynomolgus monkeys.

  DOI：

  10.1021/jm000494a

文献信息

• A Useful Methodology for the Synthesis of 2-Methyl-4-nitrobenzimidazoles
  作者：Wei Tian、Spiros Grivas

  DOI：10.1055/s-1992-26359

  日期：——

  Cyclocondensation of 3-nitro-1,2-benzenediamines 2 with 2,4-pentanedione provides a convenient route for the preparation of 2-methyl-4-nitrobenzimidazoles 3. A discrepancy in the literature regarding the 5-chloro-, 5-methoxy- and 5-methyl derivatives of the title compounds is discussed.

  3-硝基-1,2-苯二胺2与2,4-戊二酮的环化缩合反应提供了一种制备2-甲基-4-硝基苯并咪唑3的简便方法。本文讨论了关于标题化合物的5-氯代、5-甲氧基和5-甲基衍生物的文献中存在的不一致性。
• CONFORMATIONALLY RESTRICTED AROMATIC INHIBITORS OF MICROSOMAL TRIGLYCERIDE TRANSFER PROTEIN AND METHOD
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：EP0904262B1

  公开（公告）日：2004-04-21
• A Novel Series of Highly Potent Benzimidazole-Based Microsomal Triglyceride Transfer Protein Inhibitors
  作者：Jeffrey A. Robl、Richard Sulsky、Chong-Qing Sun、Ligaya M. Simpkins、Tammy Wang、John K. Dickson、Ying Chen、David R. Magnin、Prakash Taunk、William A. Slusarchyk、Scott A. Biller、Shih-Jung Lan、Fergal Connolly、Lori K. Kunselman、Talal Sabrah、Haris Jamil、David Gordon、Thomas W. Harrity、John R. Wetterau

  DOI：10.1021/jm000494a

  日期：2001.3.1

  A series of benzimidazole-based analogues of the potent MTP inhibitor EMS-201038 were discovered. Incorporation of an unsubstituted benzimidazole moiety in place of a piperidine group afforded potent inhibitors of MTP in vitro which were weakly active in vivo. Appropriate substitution on the benzimidazole ring, especially with small alkyl groups, led to dramatic increases in potency, both in a cellular assay of apoB secretion and especially in animal models of cholesterol lowering. The most potent in this series, 3g (BMS-212122), was significantly more potent than EMS-201038 in reducing plasma lipids (cholesterol, VLDL/LDL, TG) in both hamsters and cynomolgus monkeys.