3-(1H-benzo[d]imidazol-1-yl)-1-phenylpropan-1-one | 3885-72-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(1H-benzo[d]imidazol-1-yl)-1-phenylpropan-1-one
• 英文别名: 3-(1H-benzimidazol-1-yl)-1-phenyl-1-propanone；3-(1H-benzo[d]imidazole-1-yl)-1-phenylpropan-1-one；3-(1-Benzimidazolyl)-propiophenon；1-Benzimidazol-3-phenylpropan-1-on；3-benzoimidazol-1-yl-1-phenyl-propan-1-one；1-(β-Benzoyl-ethyl)-benzimidazol；3-(Benzimidazol-1-yl)-1-phenylpropan-1-one
• CAS: 3885-72-1
• 化学式: C₁₆H₁₄N₂O
• mdl: MFCD27420707
• 分子量: 250.3
• InChiKey: OAIPBIZJTVDWRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(1H-benzo[d]imidazol-1-yl)-1-phenylpropan-1-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以76%的产率得到3-(1H-benzo[d]imidazol-1-yl)-1-phenylpropan-1-ol
  参考文献：
  名称：

  Design and synthesis of 3-(azol-1-yl)phenylpropanes as microbicidal spermicides for prophylactic contraception

  摘要：

  We designed a series of 25 3-(azol-1-yl)phenylpropanes which yielded 10 compounds (3, 4, 7, 8, 13, 14, 19, 21, 23, 26) that irreversibly immobilized 100% human sperm at 1% (w/v) concentration in 60 s; 12 compounds (8, 9, 15, 16, 19-21, 23-25, 27, 28) that showed potent microbicidal activity at 12.5-50 mu g/mL against Trichomonas vaginalis; and 17 compounds (3-11, 13, 15, 19, 21, 23, 26, 28, 30) that exhibited potent anticandida activity with minimum inhibitory concentration (MIC) of 12.5-50 mu g/mL. Almost all the compounds exhibited high level of safety towards normal vaginal flora (Lactobacillus) and human cervical (HeLa) cells in comparison to the marketed spermicide nonoxynol-9 (N-9). All the biological activities were evaluated in vitro. Two compounds (4, 8) with good safety profile exhibited multiple (spermicidal, antitrichomonas and anticandida) activities, warranting further lead optimization for furnishing a prophylactic vaginal contraceptive. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.042
• 作为产物：
  描述：

  苯乙酮 在 potassium carbonate 、 三氟乙酸 、 diisopropylammonium trifluoroacetate 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 3-(1H-benzo[d]imidazol-1-yl)-1-phenylpropan-1-one
  参考文献：
  名称：

  含咪唑和苯并咪唑的曼尼希碱型衍生物的设计和合成作为南美锥虫病药物发现的先导化合物

  摘要：

  原生动物寄生虫克氏锥虫是南美锥虫病的病原体，南美锥虫病是拉丁美洲最重要的寄生虫感染。目前唯一可用的治疗方法是硝基衍生物药物，其特点是毒性大、疗效有限。因此，迫切需要更有效、毒性更小的治疗剂。我们之前已经确定了曼尼希碱衍生物作为这种寄生虫的新型抑制剂的潜力。为了进一步探索这个化合物家族，我们基于多参数结构-活性关系合成了一组 69 种新类似物，这可以优化抗寄生虫活性、物理化学参数和 ADME 特性。此外，我们优化了我们的体外针对寄生虫的所有三种发育形式的筛选方法，使我们能够在早期丢弃最不有效和抑制锥虫的衍生物。我们最终确定了衍生物3c，它表现出优异的杀锥虫特性，以及与参考药物苯并硝唑组合对锥虫的协同作用模式。其成药性和低成本生产使这种衍生物成为南美锥虫病药物发现管道临床前、体内检测的有希望的候选者。

  DOI：

  10.1016/j.ejmech.2021.113646

文献信息

• An efficient water-mediated synthetic route for the alkylation of heteroarenes
  作者：Pınar SEYİTDANLIOĞLU、Essam Hamied Ahmed HANASHALSHAHABY、Canan ÜNALEROĞLU

  DOI：10.3906/kim-1802-18

  日期：——

  for the alkylation of 1$H$-indole, 1$H$-benzimidazole, and 1$H$-benzotriazole. This approach features the alkylation of heteroaromatics through in situ generated enones from ketonic Mannich bases under metal-free conditions. A series of alkylated heteroaromatics have been synthesized via the K10 catalyzed alkylation reactions of these heteroaromatics with a variety of ketonic Mannich bases. Environmentally

  已经描述了一种有效的合成路线，用于将1 $ H $-吲哚，1 $ H $-苯并咪唑和1 $ H $-苯并三唑进行烷基化。该方法的特点是在无金属条件下通过酮基曼尼希碱原位生成的烯酮将杂芳烃烷基化。通过这些杂芳族化合物与各种酮基曼尼希碱的K10催化烷基化反应，已经合成了一系列烷基化杂芳族化合物。该烷基化方法的优点是对环境无害的K10催化剂，水介导的温和反应条件以及烷基化产物的有效合成。
• N-Alkylation of benzimidazoles with ketonic Mannich bases and the reduction of the resulting 1-(3-oxopropyl)benzimidazoles
  作者：Gheorghe Roman

  DOI：10.2478/s11532-012-0062-x

  日期：2012.10.1

  position 2, and 5,6-dimethylbenzimidazole have been alkylated at N 1 with ketonic Mannich bases derived from acetophenones, acetylnaphthalenes, 2-acetylthiophene and 1-tetralone to afford a series of novel 1-(3-oxopropyl)benzimidazoles. The reduction of these transamination products with NaBH4 in methanol produced the corresponding 1-(3-hydroxypropyl)benzimidazoles in excellent yields.

  苯并咪唑，在2位被不同取代的苯并咪唑和5,6-二甲基苯并咪唑已在 N 1被衍生自苯乙酮，乙酰萘，2-乙酰基噻吩和1-四氢萘酮的酮基曼尼希碱烷基化， 从而制得一系列新型的1-（3-氧代丙基） ）苯并咪唑 在甲醇中用NaBH 4还原这些氨基转移产物可产生相应的1-（3-羟丙基）苯并咪唑类，产率很高。
• Design and synthesis of Mannich base-type derivatives containing imidazole and benzimidazole as lead compounds for drug discovery in Chagas Disease
  作者：Iván Beltran-Hortelano、Richard L. Atherton、Mercedes Rubio-Hernández、Julen Sanz-Serrano、Verónica Alcolea、John M. Kelly、Silvia Pérez-Silanes、Francisco Olmo

  DOI：10.1016/j.ejmech.2021.113646

  日期：2021.11

  a panel of 69 new analogues, based on multi-parametric structure-activity relationships, which allowed optimization of both anti-parasitic activity, physicochemical parameters and ADME properties. Additionally, we optimized our in vitro screening approaches against all three developmental forms of the parasite, allowing us to discard the least effective and trypanostatic derivatives at an early stage

  原生动物寄生虫克氏锥虫是南美锥虫病的病原体，南美锥虫病是拉丁美洲最重要的寄生虫感染。目前唯一可用的治疗方法是硝基衍生物药物，其特点是毒性大、疗效有限。因此，迫切需要更有效、毒性更小的治疗剂。我们之前已经确定了曼尼希碱衍生物作为这种寄生虫的新型抑制剂的潜力。为了进一步探索这个化合物家族，我们基于多参数结构-活性关系合成了一组 69 种新类似物，这可以优化抗寄生虫活性、物理化学参数和 ADME 特性。此外，我们优化了我们的体外针对寄生虫的所有三种发育形式的筛选方法，使我们能够在早期丢弃最不有效和抑制锥虫的衍生物。我们最终确定了衍生物3c，它表现出优异的杀锥虫特性，以及与参考药物苯并硝唑组合对锥虫的协同作用模式。其成药性和低成本生产使这种衍生物成为南美锥虫病药物发现管道临床前、体内检测的有希望的候选者。
• Design and synthesis of 3-(azol-1-yl)phenylpropanes as microbicidal spermicides for prophylactic contraception
  作者：Lalit Kumar、Amit Sarswat、Nand Lal、Ashish Jain、Sumit Kumar、S.T.V.S. Kiran Kumar、Jagdamba P. Maikhuri、Atindra K. Pandey、Praveen K. Shukla、Gopal Gupta、Vishnu L. Sharma

  DOI：10.1016/j.bmcl.2010.11.042

  日期：2011.1

  We designed a series of 25 3-(azol-1-yl)phenylpropanes which yielded 10 compounds (3, 4, 7, 8, 13, 14, 19, 21, 23, 26) that irreversibly immobilized 100% human sperm at 1% (w/v) concentration in 60 s; 12 compounds (8, 9, 15, 16, 19-21, 23-25, 27, 28) that showed potent microbicidal activity at 12.5-50 mu g/mL against Trichomonas vaginalis; and 17 compounds (3-11, 13, 15, 19, 21, 23, 26, 28, 30) that exhibited potent anticandida activity with minimum inhibitory concentration (MIC) of 12.5-50 mu g/mL. Almost all the compounds exhibited high level of safety towards normal vaginal flora (Lactobacillus) and human cervical (HeLa) cells in comparison to the marketed spermicide nonoxynol-9 (N-9). All the biological activities were evaluated in vitro. Two compounds (4, 8) with good safety profile exhibited multiple (spermicidal, antitrichomonas and anticandida) activities, warranting further lead optimization for furnishing a prophylactic vaginal contraceptive. (C) 2010 Elsevier Ltd. All rights reserved.