1-(2-(pyrrolidin-1-yl)ethyl)-1H-benzo[d]imidazol-2-amine | 201299-81-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-(2-(pyrrolidin-1-yl)ethyl)-1H-benzo[d]imidazol-2-amine
• 英文别名: 1-(2-pyrrolidine-4-yl-ethyl)-1H-benzimidazol-2-ylamine；1-[2-(1-pyrrolidinyl)ethyl]-1H-benzimidazol-2-amine；1-[2-(1-pyrrolidinyl)ethyl]-1H-benzo[d]imidazole-2-amine；1-(2-pyrrolidin-1-ylethyl)benzimidazol-2-amine
• CAS: 201299-81-2
• 化学式: C₁₃H₁₈N₄
• mdl: MFCD00181091
• 分子量: 230.313
• InChiKey: TWYNWMMHDUDLKS-UHFFFAOYSA-N

物化性质

• 沸点：
  430.7±47.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  47.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-(pyrrolidin-1-yl)ethyl)-1H-benzo[d]imidazol-2-amine 在 高氯酸 、 乙醇 、 水 、 sodium 作用下， 反应 3.0h， 生成 2-hydroxy-10-[2-(1-pyrrolidinyl)ethyl]pyrimido[1,2-a]benzimidazol-4(10H)-one perchlorate
  参考文献：
  名称：

  Synthesis, in vitro antiplatelet activity and molecular modelling studies of 10-substituted 2-(1-piperazinyl)pyrimido[1,2- a ]benzimidazol-4(10 H )-ones

  摘要：

  The multistep preparation of the new 10-substituted 2-(1-piperazinyl)pyrimido[1,2-a]benzimidazol-4(10H)-ones 6a-o, and of the two isomers 10-ethyl-2-(diethylamino)pyrimido[1,2-a]benzimidazol-4(10H)-one 6p and 10-ethyl-4-(diethylamino)pyrimido[1,2-a]benzimidazol-2(10H)-one 13, as well as the in vitro evaluation of their inhibitory activity on human platelet aggregation induced in platelet-rich plasma by ADP, collagen or the Ca2+ ionophore A23187 were here described. Nine out of fifteen 2-(1-piperazinyl)derivatives (6g-o) showed good inhibitory properties towards all the platelet aggregation agonists used. Moreover, a molecular modelling study has been performed on two of the best compounds of this series (6i and 6o) to confirm in silico their interactions with the catalytic site of human platelet PDE3, using the X-ray data of the PDE3B isoform in complex with an inhibitor. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.01.026
• 作为产物：
  描述：

  1-(2-氨乙基)吡咯烷 在 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 1-(2-(pyrrolidin-1-yl)ethyl)-1H-benzo[d]imidazol-2-amine
  参考文献：
  名称：

  Optimisation of in silico derived 2-aminobenzimidazole hits as unprecedented selective kappa opioid receptor agonists

  摘要：

  Kappa opioid receptor (KOR) is an important mediator of pain signaling and it is targeted for the treatment of various pains. Pharmacophore based mining of databases led to the identification of 2-aminobenzimidazole derivative as KOR agonists with selectivity over the other opioid receptors DOR and MOR. A short SAR exploration with the objective of identifying more polar and hence less brain penetrant agonists is described herewith. Modeling studies of the recently published structures of KOR, DOR and MOR are used to explain the receptor selectivity. The synthesis, biological evaluation and SAR of novel benzimidazole derivatives as KOR agonists are described. The in vivo proof of principle for anti-nociceptive effect with a lead compound from this series is exemplified. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.12.064

文献信息

• Synthesis and Pharmacological Activity of Trifluoromethyl-Containing Imidazo[1,2-A]Benzimidazoles
  作者：O. N. Zhukovskaya、A. A. Spasov、T. A. Kuz’menko、A. S. Morkovnik、A. F. Kucheryavenko、V. A. Anisimova、O. A. Salaznikova、K. A. Gaidukova、V. A. Kuznetsova、D. A. Babkov、O. Yu. Grechko、N. V. Eliseeva、A. I. Rashchenko

  DOI：10.1007/s11094-018-1826-1

  日期：2018.8

  2-trifluoromethyl-9-dialkylaminoalkylimidazo[1,2-a]benzimidazoles were synthesized for the first time by reacting 2-amino-1-dialkylaminoalkylbenzimidazoles and 2-bromo-1-[(4-trifluoromethyl)phenyl]ethanone or 1-bromo-3,3,3-trifluoroacetone and were tested for analgesic and antiplatelet activity, glycogen phosphorylase and dipeptidyl peptidase-4 inhibitory activity, and in vitro glycation of bovine serum

  2-氨基-1-二烷基氨基烷基苯并咪唑与2-溴-1-[1,2-a]苯并咪唑反应首次合成了一系列2-(4-三氟甲基苯基)-和2-三氟甲基-9-二烷基氨基烷基咪唑并[1,2-a]苯并咪唑。 (4-三氟甲基)苯基]乙酮或1-溴-3,3,3-三氟丙酮，并测试了镇痛和抗血小板活性、糖原磷酸化酶和二肽基肽酶-4抑制活性，以及​​牛血清白蛋白的体外糖化作用。
• [EN] NOVEL ANTI-INFECTIVE COMPOUNDS AND METHODS USING SAME<br/>[FR] NOUVEAUX COMPOSÉS ANTI-INFECTIEUX ET LEURS MÉTHODES D'UTILISATION
  申请人：UNIV PENNSYLVANIA

  公开号：WO2016077541A1

  公开（公告）日：2016-05-19

  The present invention includes a method of treating or preventing a bacterial infection in a subject in need thereof. The method comprises administering to the subject a therapeutically effective amount of at least one compound of the invention. In certain embodiments, the bacterium is Gram-negative. In other embodiments, the bacterium is obligatory aerobic.

  本发明涉及一种治疗或预防需要的主体中的细菌感染的方法。该方法包括向该主体施用本发明至少一种化合物的治疗有效量。在某些实施方式中，细菌为革兰氏阴性菌。在其他实施方式中，细菌为厌氧菌。
• [EN] BENZIMIDAZOLE DERIVATIVES AND THEIR USE AS COOLING AGENTS<br/>[FR] DÉRIVÉS DE BENZIMIDAZOLE ET LEUR UTILISATION COMME AGENTS DE REFROIDISSEMENT
  申请人：GIVAUDAN SA

  公开号：WO2009089641A1

  公开（公告）日：2009-07-23

  The present invention refers to compounds with cooling properties, the compound are of formula (I), wherein R1 is selected from the list consisting of C1 - C3 alkyl, - SCH3, and - NH2, and - CHR'OR'' wherein R' and R'' are independently selected from hydrogen, methyl and ethyl; R2 is selected from the list consisting of hydrogen, C1 - C3 alkyl, and a halide; and I) A is formula (II) wherein R is selected from hydrogen, -OR11 wherein R11 is selected from hydrogen, and C1-C3 alkyl; halide; -NO2; -CN; -C(O)NH2; and -C(O)OR12 wherein R12 is selected from hydrogen, and C1-C3 alkyl; and X is selected from the list consisting of -CH2-, -C(O) -, and -C(O)NHCH2-; or II) A is formula (III) wherein n is 0 or 1.

  本发明涉及具有冷却性能的化合物，该化合物的化学式为(I)，其中R1从以下列表中选择：C1 - C3烷基，-SCH3，-NH2，和-CHR'OR''，其中R'和R''分别独立地选择自氢，甲基和乙基；R2从以下列表中选择：氢，C1 - C3烷基，和卤素；以及I）A为化学式(II)，其中R从氢，-OR11（其中R11从氢和C1-C3烷基中选择），卤素，-NO2，-CN，-C(O)NH2，和-C(O)OR12（其中R12从氢和C1-C3烷基中选择）中选择；X从以下列表中选择：-CH2-，-C(O)-，和-C(O)NHCH2-；或II）A为化学式(III)，其中n为0或1。
• BENZIMIDAZOLES THAT ENHANCE THE ACTIVITY OF OLIGONUCLEOTIDES
  申请人：The University of North Carolina at Chapel Hill

  公开号：US20190343868A1

  公开（公告）日：2019-11-14

  This disclosure is directed to methods, compounds and compositions for delivering nucleic acids to a cell of interest. In particular, it provides salts that are particularly effective in delivering nucleic acids to cells in the lung for disorders such as cystic fibrosis (CF).

  本公开涉及将核酸传递到感兴趣的细胞的方法、化合物和组合物。特别地，它提供了对于像囊性纤维化（CF）这样的肺部疾病中将核酸传递到细胞特别有效的盐。
• Benzimidazole Derivatives And Their Use As Cooling Agents
  申请人：Furrer Stefan Michael

  公开号：US20100297038A1

  公开（公告）日：2010-11-25

  The present invention refers to compounds with cooling properties, the compound are of formula (I), wherein R 1 is selected from the list consisting of C 1 -C 3 alkyl, —SCH 3 , and —NH 2 , and —CHR′OR″ wherein R′ and R″ are independently selected from hydrogen, methyl and ethyl; R 2 is selected from the list consisting of hydrogen, C 1 -C 3 alkyl, and a halide; and I) A is wherein R is selected from hydrogen, —OR 11 wherein R 11 is selected from hydrogen, and C 1 -C 3 alkyl; halide; —NO 2 ; —CN; —C(O)NH 2 ; and —C(O)OR 12 wherein R 12 is selected from hydrogen, and C 1 -C 3 alkyl; and X is selected from the list consisting of —CH 2 —, —C(O)—, and —C(O)NHCH 2 —; or II) A is wherein n is 0 or 1.

  本发明涉及具有冷却特性的化合物，该化合物的化学式为（I），其中R1从以下列表中选择，该列表包括C1-C3烷基，—SCH3和—NH2，以及—CHR′OR″，其中R′和R″独立地选择自氢，甲基和乙基；R2从以下列表中选择，该列表包括氢，C1-C3烷基和卤化物；以及I) A，其中R从氢，—OR11中选择，其中R11从氢和C1-C3烷基中选择；卤化物；—NO2；—CN；—C（O）NH2；和—C（O）OR12，其中R12从氢和C1-C3烷基中选择；和X从以下列表中选择，该列表包括—CH2—，—C（O）—和—C（O）NHCH2—；或II）A为其中n为0或1。