2-(4-bromobenzylsulfanyl)-1H-benzimidazole | 296273-25-1

• 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: 2-(4-bromobenzylsulfanyl)-1H-benzimidazole
• 英文别名: 2-((4-bromobenzyl)thio)-1H-benzo[d]imidazole；2-((4-bromobenzyl)thio)-1H-benzimidazole；2-[(4-bromophenyl)methylsulfanyl]-1H-benzimidazole
• CAS: 296273-25-1
• 化学式: C₁₄H₁₁BrN₂S
• mdl: MFCD00518701
• 分子量: 319.225
• InChiKey: SSZXTFFESFXOKA-UHFFFAOYSA-N

物化性质

• 沸点：
  501.3±52.0 °C(Predicted)
• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  54
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-bromobenzylsulfanyl)-1H-benzimidazole 在 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium carbonate 、 三环己基膦 作用下， 以 1,4-二氧六环 、 水 、 丙酮 为溶剂， 反应 25.0h， 生成 (E)-1-(3-(((4'-methoxy-[1,1'-biphenyl]-4-yl)methyl)thio)pent-2-en-1-yl)-2-(4-methoxyphenyl)-1H-benzimidazole
  参考文献：
  名称：

  2-亚磺酰基苯并咪唑与硼酸的串联双交叉偶联/加氢硫醇化反应

  摘要：

  据报道，一种新的串联钯催化的反应涉及Suzuki-Miyaura偶联，脱硫基偶联和三键的氢硫基化。值得注意的是，在没有铜（I）辅助的情况下发生了脱硫基偶联，并且氢硫基化是完全区域选择性和立体选择性的。整个过程导致硼酸的两次掺入和亚硫基部分的再掺入到产物结构中。从2-（溴苄基亚硫基）-1-炔丙基苯并咪唑开始，该转化导致带有立体定义的烯基硫的各种取代的苯并咪唑。

  DOI：

  10.1021/acs.orglett.9b02067
• 作为产物：
  描述：

  对溴溴苄 、 1H-苯并咪唑-2-硫醇 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以76%的产率得到2-(4-bromobenzylsulfanyl)-1H-benzimidazole
  参考文献：
  名称：

  Design, Synthesis and Antitubercular Activity of 2-(Benzylthio)-1H-benzo[d]imidazoles

  摘要：

  利用分子简化和分子杂化方法，合成了一系列2-(苄硫基)-1H-苯并[d]咪唑类化合物，并作为体外抑制结核分枝杆菌(M. tuberculosis)生长的试剂进行评估。该系列化合物中的6p和6z被认为是领先的化合物，对M. tuberculosis H37Rv的最小抑制浓度（MIC）分别为6.9和3.8μM。此外，这些领先的化合物对多药耐药菌株也具有活性，并且对Vero和HepG2细胞没有明显毒性，这是通过3-(4,5-二甲基噻唑-2-基)-2,5-二苯基四唑溴化物（MTT）和中性红试验得出的。最后，这些化合物具有良好的水溶性和高的血浆稳定性。这些数据表明，这一类分子可能为未来开发新的抗结核病药物候选物提供了可能性。

  DOI：

  10.21577/0103-5053.20210040

文献信息

• Facile synthesis and antimicrobial properties of 2-(substituted-benzylsulfanyl)-1<i>h</i>-benzimidazoles
  作者：Ramanatham Vinod Kumar、Kotarkonda Raja Gopal、Kotha V. S. R. Seshu Kumar

  DOI：10.1002/jhet.5570420722

  日期：2005.11

  2-benzylthiobenzirnidazoles by the reaction of 2-mercaptobenzimidazole and benzyl bromides in acetone/potassium carbonate condition has been reported and the compounds were screened for their potential antimicrobial activities.

  已经报道了在丙酮/碳酸钾条件下通过2-巯基苯并咪唑和苄基溴的反应制备2-苄基硫代苯并咪唑的简单方便的方法，并筛选了化合物的潜在抗菌活性。
• Correlation Analysis in the Benzylation of Sulfur Nucleophiles
  作者：P. Kalyani、P. Manikyamba

  DOI：10.3184/030823407x191985

  日期：2007.2

  In the nucleophilic substitution reaction of benzyl bromides with three sulfur nucleophiles a linear relationship between the nucleophile discrimination parameter (s) and the Hammett substituent constant (σ) is observed.

  在苄基溴与三个硫亲核试剂的亲核取代反应中，观察到亲核试剂区分参数 (s) 和哈米特取代基常数 (σ) 之间的线性关系。
• [Mn(salophen)Cl] supported on modified polystyrene as a selective heterogeneous catalyst for oxidation of sulfides under ultrasonic irradiation
  作者：V. Mirkhani、S. Tangestaninejad、M. Moghadam、I. Mohammadpoor-Baltork、Z. Saedi

  DOI：10.1007/bf03246056

  日期：2010.9

  The use of ultrasonic irradiation for the selective synthesis of sulfone in the oxidation of sulfides with NaIO4 catalyzed by Mn(Salophen) supported on chloromethylated polystyrene-bound imidazole, [Mn(Salophene)-PSI], is reported. This heterogeneous catalyst efficiently catalyzed selective oxidation of sulfides to sulfones under ultrasonic irradiation and no sulfoxide was detected in the reaction

  据报道，使用超声辐射选择性地合成了砜，该砜被氯化甲基化聚苯乙烯键合的咪唑[Mn（Salophene）-PSI]上负载的Mn（Salophen）催化的NaIO 4氧化硫化物。这种多相催化剂在超声辐射下有效地催化了硫化物选择性氧化为砜，并且在反应混合物中未检测到亚砜。
• One-Pot Synthesis of 2-Benzyl/2-Allyl-Substituted Thiobenzoazoles Using Transition-Metal-Free Conditions in Water
  作者：Shi-Bo Zhang、Xing Liu、Ming-Yuan Gao、Zhi-Bing Dong

  DOI：10.1021/acs.joc.8b02136

  日期：2018.12.21

  A transition-metal-free protocol for the one-pot synthesis of 2-benzyl/2-allyl-substituted thiobenzoazoles in water was developed. The cyclization of 2-aminothiophenols, 2-aminophenols, and 1,2-phenylenediamines with tetramethylthiuram disulfide (TMTD) gave mercapto benzoheterocycles, and the subsequent C-S coupling with benzyl or allyl halides furnished the desired products in good to excellent yields. This method features transition-metal-free conditions with water as a solvent, an easy performance, mild reaction conditions, a wide substrate scope, and good to excellent yields, thus paving an efficient and useful way to establish a library of potentially active drug molecules.
• Synthesis and preliminary evaluation of benzimidazole derivatives as antimicrobial agents
  作者：Věra Klimešová、Jan Kočı́、Milan Pour、Jiřı́ Stachel、Karel Waisser、Jarmila Kaustová

  DOI：10.1016/s0223-5234(02)01342-9

  日期：2002.5

  A series of 2-alkylsulphanylbenzimidazoles was synthesised and the compounds were evaluated for their in vitro antimicrobial activity. The structures of the compounds were confirmed by H-1-NMR and IR data, and their purity by elemental analysis. Antimycobacterial activities against Mycobacterium tuberculosis and non-tuberculous mycobacteria as well as antifungal activities against Candida albicans, Candida tropicalis, Candida krusei, Candida glabrata, Trichosporon beigelii, Trichophyton mentagrophytes and Aspergillus fumigatus were expressed as the corresponding MIC values. The substances exhibited appreciable antimycobacterial activity, in particular, against non-tuberculous mycobacteria. The activity of the most active compound in the set, 3,5-dinitro derivative 4t, exceeded that of the standard isoniazide against M. kansasii and M. avium. The antifungal activities of the compounds were relatively low. A weak antifungal effect was observed against the dermatophyte Trichophyton mentagrophytes. None of the compounds showed significant inhibitory activity against yeasts. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.