2-(吡啶-2-基)-1H-1,3-苯并二唑-5-胺 | 55396-63-9

• 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-(吡啶-2-基)-1H-1,3-苯并二唑-5-胺
• 英文名称: 5-amino-2-(α-pyridyl)benzimidazoles
• 英文别名: 2-(pyridin-2-yl)-1H-benzimidazol-5-amine；2-(2'-pyridyl)-5-amino-1H-benzimidazole；2-pyridin-2-yl-1H-benzoimidazol-5-ylamine；2-pyridin-2-yl-3H-benzimidazol-5-amine
• CAS: 55396-63-9
• 化学式: C₁₂H₁₀N₄
• mdl: MFCD00089423
• 分子量: 210.238
• InChiKey: ITFXYBZUPPBWEC-UHFFFAOYSA-N

物化性质

• 熔点：
  217 °C(Solv: ethanol (64-17-5))
• 沸点：
  511.2±48.0 °C(Predicted)
• 密度：
  1.348±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(吡啶-2-基)-1H-1,3-苯并二唑-5-胺 、 1,6,7,12-四氯-3,4,9,10-苝四甲酸二酐 在 丙酸 作用下， 反应 24.0h， 以86%的产率得到N,N'-bis(2-(2'-pyridyl)-1H-benzimidazole)-1,6,7,12-tetrachloro-3,4,9,10-perylenetetracarboxylic acid diimide
  参考文献：
  名称：

  新型2-（2'-吡啶基）-1H-苯并咪唑附加的海湾取代的per二酰亚胺三联体的光谱，电化学和比色性质

  摘要：

  在这项研究中，四个新的per二酰亚胺（PDI）衍生物在酰亚胺位置结合了2-（2'-吡啶基）-1H-苯并咪唑（2PBI）生色团，其中1个带有未被Bay取代的core核，而那些具有4个在per中心的1,6,7,12-bay位置的取代基，即2个带有吸电子的氯原子，3个带有供电子的4-甲氧基苯氧基和4个带有非供电子的4-叔丁基苯氧基，分别进行了合成和FT-IR，1 H NMR，13表征13 C NMR，MALDI-TOF质谱和UV / Vis光谱。热特性的结果通过热重分析（TGA），其结果表明，原料（测量1 - 4是热非常稳定（T）d> 450°C）。使用DFT进行几何优化，并使用TDDFT来比较在B3LYP / 6–311 G（d）水平下计算的和实验的UV / Vis电子光谱。为了了解新化合物的氧化还原性质，颜色变化和光电特性，使用电分析，光谱和比色技术进行了详细的测量。这些2PBI功能化的PD

  DOI：

  10.1016/j.jphotochem.2019.04.039
• 作为产物：
  描述：

  5-nitro-2-pyridin-2-yl-1(3)H-benzoimidazole 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以80%的产率得到2-(吡啶-2-基)-1H-1,3-苯并二唑-5-胺
  参考文献：
  名称：

  Metal-Mediated Inhibition of Escherichia coli Methionine Aminopeptidase:  Structure−Activity Relationships and Development of a Novel Scoring Function for Metal−Ligand Interactions

  摘要：

  We report the discovery of thiabendazole as a potent inhibitor (K-i = 0.4 mu M) of Escherichia coli methionine aminopeptidase (ecMetAP) and the synthesis and pharmacological evaluation of thiabendazole congeners with activity in the upper nanomolar range. Elucidation of the X-ray structure of ecMetAP in complex with thiabendazole and an unrelated inhibitor that was independently described by another group showed that that both compounds bind to an additional Coll ion at the entrance of the active site. This unexpected finding explains the inactivity of the compounds under in vivo conditions. It also allows us to discuss the structure-activity relationships of this series of compounds in a meaningful way, based upon docking runs with an auxiliary metal ion. We describe a new scoring function for the evaluation of metal-mediated inhibitor binding that, unlike the previously used scoring function implemented in the docking program, allows us to distinguish between active and inactive compounds. Finally, conclusions for the structure-based design of in vivo-active inhibitors of ecMetAP are drawn.

  DOI：

  10.1021/jm050476z

文献信息

• SUBSTITUTED PYRIDINYL-PYRIMIDINES AND THEIR USE AS MEDICAMENTS
  申请人：Dahmann Georg

  公开号：US20130023502A1

  公开（公告）日：2013-01-24

  The invention relates to new substituted pyridinyl-pyrimidines of formula 1 wherein ring A is a five-membered saturated or unsaturated carbocyclic ring which optionally comprises one, two or three heteroatoms each independently from each other selected from the group N, S and O, wherein R 1 , R 2 , R 4 , R 3 , R 5 and R 6 are defined as in claim 1 and wherein ring A is further optionally substituted by one or two further substituents and the pharmaceutically acceptable salts, diastereomers, enantiomers, racemates, hydrates and solvates of the aforementioned compounds.

  该发明涉及公式1中的新取代吡啶基嘧啶化合物， 其中环A是一个含有五个成员的饱和或不饱和碳环，该环可选地包含一个、两个或三个异原子，每个异原子独立地选自N、S和O组成， 其中R1、R2、R4、R3、R5和R6如权利要求书中所定义，并且环A进一步可选地被一个或两个进一步取代基取代，以及上述化合物的药用盐、二对映体、对映体、消旋体、水合物和溶剂化合物。
• [EN] SUBSTITUTED PYRIDINYL-PYRIMIDINES AND THEIR USE AS MEDICAMENTS<br/>[FR] PYRIDINYL-PYRIMIDINES SUBSTITUÉES ET LEUR UTILISATION EN TANT QUE MÉDICAMENTS
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2012101013A1

  公开（公告）日：2012-08-02

  The invention relates to new substituted pyridinyl-pyrimidines of formula 1 wherein ring A is a five-membered saturated or unsaturated carbocyclic ring which optionally comprises one, two or three heteroatoms each independently from each other selected from the group N, S and O, wherein R1, R2, R4, R3, R5 and R6 are defined as in claim 1 and wherein ring A is further optionally substituted by one or two further substituents and the pharmaceutically acceptable salts, diastereomers, enantiomers, racemates, hydrates and solvates of the aforementioned compounds.

  该发明涉及公式1中的新取代吡啶基嘧啶，其中环A是一个五元饱和或不饱和碳环，可选地包含一个、两个或三个异原子，每个异原子独立地选自N、S和O组，其中R1、R2、R4、R3、R5和R6如权利要求1中所定义，环A进一步可选地被一个或两个进一步取代基取代，以及上述化合物的药学上可接受的盐、二对映体、对映体、消旋体、水合物和溶剂化合物。
• [EN] CARBONYLAMINO-BENZIMIDAZOLE DERIVATIVES AS ANDROGEN RECEPTOR MODULATORS<br/>[FR] DERIVES DE CARBONYLAMINO-BENZIMIDAZOLE UTILISES COMME MODULATEURS DU RECEPTEUR ANDROGENE
  申请人：MERCK & CO INC

  公开号：WO2004041277A1

  公开（公告）日：2004-05-21

  Compounds of structural formula (I) are modulators of the androgen receptor (AR) in a tissue selective manner. They are useful as agonists of the androgen receptor in bone and/or muscle tissue while antagonizing the AR in the prostate of a male patient or in the uterus of a female patient. These compounds are therefore useful in the enhancement of weakened muscle tone and the treatment of conditions caused by androgen deficiency or which can be ameliorated by androgen administration, including osteoporosis, osteopenia, glucocorticoid-induced osteoporosis, periodontal disease, bone fracture, bone damage following bone reconstructive surgery, sarcopenia, frailty, aging skin, male hypogonadism, postmenopausal symptoms in women, atherosclerosis, hypercholesterolemia, hyperlipidemia, obesity, aplastic anemia and other hematopoietic disorders, arthritic condition and joint repair, HIV-wasting, prostate cancer, cancer cachexia, Alzheimer s disease, muscular dystrophies, premature ovarian failure, and autoimmune disease, alone or in combination with other active agents.

  化学结构式（I）的化合物以组织选择性的方式调节雄激素受体（AR）。它们在男性患者的前列腺或女性患者的子宫中对AR产生拮抗作用，同时在骨骼和/或肌肉组织中作为雄激素受体激动剂，因此这些化合物对于增强肌肉张力和治疗由雄激素缺乏引起或可以通过雄激素治疗改善的疾病具有用处，包括骨质疏松症、骨质疏松、糖皮质激素诱导的骨质疏松症、牙周病、骨折、骨重建手术后的骨损伤、肌肉萎缩、衰弱、皮肤老化、男性性腺功能减退、女性绝经后症状、动脉硬化、高胆固醇血症、高脂血症、肥胖症、再生障碍性贫血和其他造血系统疾病、关节炎和关节修复、HIV消耗综合症、前列腺癌、癌性消瘦、阿尔茨海默病、肌萎缩性疾病、卵巢早衰和自身免疫疾病，可单独使用或与其他活性剂联合使用。
• Carbonylamino-benzimidazole derivatives as androgen receptor modulators
  申请人：Kim Yuntae

  公开号：US20060036098A1

  公开（公告）日：2006-02-16

  Compounds of structural formula (I) are modulators of the androgen receptor (AR) in a tissue selective manner. They are useful as agonists of the androgen receptor in bone and/or muscle tissue while antagonizing the AR in the prostate of a male patient or in the uterus of a female patient. These compounds are therefore useful in the enhancement of weakened muscle tone and the treatment of conditions caused by androgen deficiency or which can be ameliorated by androgen administration, including osteoporosis, osteopenia, glucocorticoid-induced osteoporosis, periodontal disease, bone fracture, bone damage following bone reconstructive surgery, sarcopenia, frailty, aging skin, male hypogonadism, postmenopausal symptoms in women, atherosclerosis, hypercholesterolemia, hyperlipidemia, obesity, aplastic anemia and other hematopoietic disorders, arthritic condition and joint repair, HIV-wasting, prostate cancer, cancer cachexia, Alzheimer s disease, muscular dystrophies, premature ovarian failure, and autoimmune disease, alone or in combination with other active agents.

  化学式（I）的化合物在组织选择性方面是雄激素受体（AR）的调节剂。它们在男性患者的前列腺或女性患者的子宫中作为雄激素受体拮抗剂，同时在骨骼和/或肌肉组织中作为雄激素受体激动剂，因此在增强肌肉张力和治疗由雄激素缺乏引起或可以通过雄激素治疗改善的疾病，包括骨质疏松症、骨质疏松、糖皮质激素诱导的骨质疏松症、牙周疾病、骨折、骨重建手术后的骨损伤、肌无力、衰弱、老化皮肤、男性性腺功能减退症、女性绝经后症状、动脉粥样硬化、高胆固醇血症、高脂血症、肥胖症、再生障碍性贫血和其他造血系统疾病、关节炎和关节修复、艾滋病浪费、前列腺癌、癌症消瘦、阿尔茨海默病、肌萎缩症、早发性卵巢衰竭和自身免疫性疾病方面具有用途，可以单独或与其他活性剂联合使用。
• SUBSTITUTED PHENYLALANINE DERIVATIVES
  申请人：BAYER PHARMA AKTIENGESELLSCHAFT

  公开号：US20160272617A1

  公开（公告）日：2016-09-22

  The invention relates to substituted phenylalanine derivatives and to processes for preparation thereof, and to the use thereof for production of medicaments for treatment and/or prophylaxis of diseases, especially of cardiovascular disorders and/or severe perioperative blood loss.

  本发明涉及取代苯丙氨酸衍生物的制备方法，以及用于制备治疗和/或预防疾病的药物的使用，特别是用于治疗心血管障碍和/或严重围手术期失血。