(9ci)-1-乙基-1H-苯并咪唑-2-乙腈 | 25184-09-2

• 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-乙基-1H-苯并咪唑-2-乙腈
• 英文名称: 1-ethyl-2-benzimidazolylacetonitrile
• 英文别名: (1-ethyl-1H-benzoimidazol-2-yl)-acetonitrile；1-Ethyl-2-cyanmethyl-benzimidazol；N-Ethyl-2-benzimidazolacetonitril；(1-ethyl-1H-benzimidazol-2-yl)acetonitrile；2-(1-ethylbenzimidazol-2-yl)acetonitrile
• CAS: 25184-09-2
• 化学式: C₁₁H₁₁N₃
• mdl: MFCD00456343
• 分子量: 185.228
• InChiKey: LMKZNSKYLAQXJH-UHFFFAOYSA-N

物化性质

• 熔点：
  156 °C
• 沸点：
  385.3±25.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  41.6
• 氢给体数：
  0
• 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：

  (9ci)-1-乙基-1H-苯并咪唑-2-乙腈 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 10-Ethyl-1,3,6,10-tetraazatetracyclo[7.7.0.0^{2,7}.0^{11,16}]hexadeca-2(7),3,5,8,11(16),12,14-heptaene-4,5,8-tricarbonitrile
  参考文献：
  名称：

  Synthesis of condensed pyrrolo[b]pyrazines

  摘要：

  DOI：

  10.1007/bf02251802
• 作为产物：
  描述：

  邻苯二胺 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 (9ci)-1-乙基-1H-苯并咪唑-2-乙腈
  参考文献：
  名称：

  Development of benzimidazole derivatives to inhibit HIV-1 replication through protecting APOBEC3G protein

  摘要：

  Human APOBEC3G (apolipoprotein B mRNA-editing enzyme, catalytic polypeptide-like 3G, MG) is a potent restriction factor against human immunodeficiency virus type 1 (HIV-1) by inducing hypermutation of G to A in viral genome after its incorporation into virions. HIV-1 Vif (Virion Infectivity Factor) counteracts A3G by inducing ubiquitination and proteasomal degradation of MG protein. Vif-A3G axis therefore is a promising therapeutic target of HIV-1. Here we report the screening, synthesis and SAR studies of benzimidazole derivatives as potent inhibitors against HIV-1 replication via protecting MG protein. Based on the steep SAR of the benzimidazole scaffold, we identified compound 14 and 26 which provided the best potency, with IC50 values of 3.45 nM and 58.03 nM respectively in the anti-HIV-1 replication assay in H9 cells. Compound 14 and 26 also afforded protective effects on MG protein level. Both compounds have been proved to be safe in acute toxicological studies. Taken together, we suggest that these two benzimidazole derivatives can be further developed as a new category of anti-HIV-1 leads. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.03.050

文献信息

• [EN] BENZIMIDAZOLE ACETONITRILES<br/>[FR] BENZOXAZOLE ACÉTONITRILES
  申请人：APPLIED RESEARCH SYSTEMS

  公开号：WO2005026155A1

  公开（公告）日：2005-03-24

  The present invention is related to benzimidazole acetonitriles as well as to pharmaceutical formulations containing such benzimidazole acetonitriles of formula (I). Said benzimidazole acetonitriles are useful in the treatment of metabolic disorders mediated by insulin resistance or hyperglycemia, comprising diabetes type II, inadequate glucosetolerance, insulin resistance, obesity, polycystic ovary syndrome (PCOS) (I). The present invention is furthermore related to methods of preparing ben7.oxazole acetonitriles. G is pyrimidinyl; L is an amino group, or a 3-8 membered heterocycloalkyl, containing at least one heteroatorn selected from N, O, S or L is an acylamino moiety; R1 is selected from the group comprising or consisting of hydrogen, sulfonyl, amino, carboxy, aminocarbonyl, CI-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl or Cl-C6-alkoxy, aryl,halogen, cyano or hydroxy;R2 is selected from the group comprising or consisting of hydrogen, CI -C6-alkyl, C2-C6alkenyl, C2-C6-alkynyl, or CI -C6-alkoxy.

  本发明涉及苯并咪唑乙腈，以及含有该苯并咪唑乙腈的药物配方（I）的制备方法。所述苯并咪唑乙腈可用于治疗由胰岛素抵抗或高血糖介导的代谢紊乱，包括糖尿病II型、葡萄糖耐量不良、胰岛素抵抗、肥胖、多囊卵巢综合征（PCOS）。本发明还涉及制备苯7氧唑乙腈的方法。其中G为嘧啶基；L为氨基，或者含有至少一个来自N、O、S的杂原子的3-8成员杂环烷基，或者L为酰氨基基团；R1选自氢、磺酰基、氨基、羧基、氨基甲酰基、C1-C6烷基、C2-C6烯基、C2-C6炔基、或者C1-C6烷氧基的群；R2选自氢、C1-C6烷基、C2-C6烯基、C2-C6炔基、或者C1-C6烷氧基的群。
• Medicaments
  申请人：Alberti John Michael

  公开号：US20050153978A1

  公开（公告）日：2005-07-14

  A method of treating an Msk-1 and/or ROCK(1 and 2) mediated disease or condition in a mammal comprising administration of an effective amount of a compounds of the formula (I) and physiologically acceptable salts thereof wherein, R 1 is a 5, or 6 membered heterocyclic group selected from group a, b, c or d wherein X 1 is a group selected from N or CR 7 and X 2 is a group selected from O, S or NR 8 ; X 3 and X 4 which may be the same or different is a group selected from N or CR 7 ; X 5 is a group selected from O, S or NR 8 and X 6 is N or CR 7 ; X 7 , X 8 and X 9 may be the same or different and selected from a group N or CR 7 , pharmaceutical compositions, novel compounds and processes for their preparation.

  一种治疗哺乳动物中MSK-1和/或ROCK（1和2）介导的疾病或病况的方法，包括给予化合物(I)及其生理上可接受的盐的有效量，其中，R1是从a、b、c或d组中选择的5个或6个成员的杂环基团，其中X1是选择自N或CR7的基团，X2是选择自O、S或NR8的基团；X3和X4可以相同或不同，是选择自N或CR7的基团；X5是选择自O、S或NR8的基团，X6是N或CR7；X7、X8和X9可以相同或不同，选择自N或CR7的基团；制备这些新化合物的药物组合物和方法。
• Benzimidazole Acetonitriles
  申请人：Schwarz Matthias

  公开号：US20070203134A1

  公开（公告）日：2007-08-30

  The present invention is related to benzimidazole acetonitriles as well as to pharmaceutical formulations containing such benzimidazole acetonitriles of formula (I). Said benzimidazole acetonitriles are useful in the treatment of metabolic disorders mediated by insulin resistance or hyperglycemia, comprising diabetes type II, inadequate glucose tolerance, insulin resistance, obesity, polycystic ovary syndrome (PCOS) (I). The present invention is furthermore related to methods of preparing benzoxazole acetonitriles. G is pyrimidinyl; L is an amino group, or a 3-8 membered heterocycloalkyl, containing at least one heteroatom selected from N, O, S or L is an acylamino moiety; R 1 is selected from the group comprising or consisting of hydrogen, sulfonyl, amino, carboxy, aminocarbonyl, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 1 -C 6 -alkoxy, aryl, halogen, cyano or hydroxy; R 2 is selected from the group comprising or consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 alkenyl, C 2 -C 6 -alkynyl, or C 1 -C 6 -alkoxy.

  本发明涉及苯并咪唑乙腈以及含有该苯并咪唑乙腈的制药配方(I)。所述苯并咪唑乙腈在治疗由胰岛素抵抗或高血糖介导的代谢紊乱方面具有用途，包括2型糖尿病、不足的葡萄糖耐受性、胰岛素抵抗、肥胖症、多囊卵巢综合症（PCOS）(I)。本发明还涉及制备苯并噁唑乙腈的方法。其中G为嘧啶基；L为氨基，或者是一个3-8成员的杂环烷基，其中至少包含一个从N、O、S中选择的杂原子，或者L为一个酰胺基；R1选自包括或仅包括氢、磺酰基、氨基、羧基、氨基甲酰基、C1-C6烷基、C2-C6烯基、C2-C6炔基或C1-C6烷氧基、芳基、卤素、氰基或羟基的群；R2选自包括或仅包括氢、C1-C6烷基、C2-C6烯基、C2-C6炔基或C1-C6烷氧基的群。
• Novel synthesis of 2-amino-3-hetaryl-4(5H)-oxothiophenes
  作者：Yu. M. Volovenko、T. A. Volovnenko、A. V. Dobrydnev

  DOI：10.1007/s10593-006-0132-0

  日期：2006.5
• Nucleophilic substitution in 1-alkyl-4,5-dichloro-3-nitropyridazin-6-ones
  作者：Yu. M. Volovenko、T. A. Volovnenko

  DOI：10.1007/s10593-006-0115-1

  日期：2006.4