2-((1H-benzo[d]imidazol-2-yl)thio)-N'-(2-hydroxybenzylidene)acetohydrazide | 63875-31-0

• 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-((1H-benzo[d]imidazol-2-yl)thio)-N'-(2-hydroxybenzylidene)acetohydrazide
• 英文别名: (1H-benzimidazol-2-ylsulfanyl)acetic acid (2-hydroxybenzylidene)hydrazide；2-[[[2-(1H-benzimidazol-1-ium-2-ylsulfanyl)acetyl]hydrazinylidene]methyl]phenolate
• CAS: 63875-31-0
• 化学式: C₁₆H₁₄N₄O₂S
• mdl: MFCD00396401
• 分子量: 326.379
• InChiKey: GGRUVZCVGNSFQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  116
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-((1H-benzo[d]imidazol-2-yl)thio)-N'-(2-hydroxybenzylidene)acetohydrazide 在 PPA 作用下， 反应 20.0h， 以70%的产率得到3-benzimidazolylthiochromone
  参考文献：
  名称：

  Ahluwalia, V K; Tyagi, Renu; Khurana, Anju, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1990, vol. 29, # 12, p. 1097 - 1100

  摘要：

  DOI：
• 作为产物：
  描述：

  1H-苯并咪唑-2-硫醇 在 potassium carbonate 、 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 11.0h， 生成 2-((1H-benzo[d]imidazol-2-yl)thio)-N'-(2-hydroxybenzylidene)acetohydrazide
  参考文献：
  名称：

  2-巯基苯并咪唑衍生物的合成作为潜在的抗微生物和细胞毒性剂

  摘要：

  由各种醛和 2- (5-苯基- [1,3,4] -oxadiazol-2-ylmethylsulfanyl) -1H-苯并咪唑 6a – j 来自各种苯甲酸。筛选了这些化合物对金黄色葡萄球菌和粪肠球菌作为革兰氏阳性菌、肺炎克雷伯菌和大肠杆菌作为革兰氏阴性菌株的体外抗细菌活性以及对烟曲霉和白色念珠菌的体外抗真菌活性。使用盐水虾生物测定研究了体外细胞毒性特性。结果表明，化合物5b、5d、5g、5i、6b、6e、6f和6i对一组微生物显示出极好的活性。发现5b、5g、5i、6b、6f、6h和6i的细胞毒活性良好。

  DOI：

  10.1002/ardp.200900291

文献信息

• Synthesis of 2-Mercaptobenzimidazole Derivatives as Potential Anti-microbial and Cytotoxic Agents
  作者：Kallappa M. Hosamani、Ramya V. Shingalapur

  DOI：10.1002/ardp.200900291

  日期：2011.5

  for in‐vitro anti‐fungal activity against Asperigillus fumigatus and Candida albicans. The in vitro cytotoxic properties were studied using brine shrimp bioassay. Results revealed that, compounds 5b, 5d, 5g, 5i, 6b, 6e, 6f, and 6i showed excellent activity against a panel of microorganisms. The cytotoxic activities of 5b, 5g, 5i, 6b, 6f, 6h, and 6i were found to be good. All the newly synthesized compounds

  由各种醛和 2- (5-苯基- [1,3,4] -oxadiazol-2-ylmethylsulfanyl) -1H-苯并咪唑 6a – j 来自各种苯甲酸。筛选了这些化合物对金黄色葡萄球菌和粪肠球菌作为革兰氏阳性菌、肺炎克雷伯菌和大肠杆菌作为革兰氏阴性菌株的体外抗细菌活性以及对烟曲霉和白色念珠菌的体外抗真菌活性。使用盐水虾生物测定研究了体外细胞毒性特性。结果表明，化合物5b、5d、5g、5i、6b、6e、6f和6i对一组微生物显示出极好的活性。发现5b、5g、5i、6b、6f、6h和6i的细胞毒活性良好。
• Synthesis and Characterization of Lanthanide(III) Nitrate Complexes with Terdentate ONO Donor Hydrazone Derived from 2-Benzimidazolyl Mercaptoaceto Hydrazide and o-Hydroxy Aromatic Aldehyde
  作者：Vinayak M. Naik、Nirmalkumar B. Mallur

  DOI：10.1155/2011/743948

  日期：——

  A few eight coordinated complexes of lanthanide(III) nitrate with 2-benzimidazolyl mercaptoaceto hydrazone ligand (LH₂) with the general formula [Ln(LH)₂NO₂]H₂O (where Ln = La, Pr, Nd, Sm and Gd) have been synthesized and characterized by elemental analysis, magnetic susceptibility, molar conductance, UV-Visible, IR and¹H NMR spectral studies. The experimental data sustain stoichiometry of 1:2 (metal/ligand) for the complexes. The spectral data shows that the ligand reacts in keto form and behaves as monobasic terdentate in nature. The nitrate appears to coordinate in the bidentate fashion to the metal ion. The thermal stabilities of the complexes have been studied by TGA and their kinetic parameters were calculated using Coats-Redfern and MKN methods. The antimicrobial activity studies have been under taken and results are discussed.

  已合成并表征了几个镧系(III)硝酸盐与2-苯并咪唑硫醇乙酰肼配体(LH2)的八配位配合物，其通式为[Ln(LH)2NO2]H2O (其中Ln = 镧、镨、钕、钐和钆)。通过元素分析、磁化率、摩尔电导率、紫外可见、红外和1H核磁共振光谱研究对其进行了表征。实验数据支持配合物的1:2(金属/配体)化学计量比。光谱数据显示，配体以酮式形式反应，并表现出单碱性三齿配位性质。硝酸盐以双齿方式配位于金属离子上。使用TGA研究了配合物的热稳定性，并使用Coats-Redfern和MKN方法计算了其动力学参数。进行了抗微生物活性研究并讨论了结果。
• Derivatives of benzimidazole pharmacophore: Synthesis, anticonvulsant, antidiabetic and DNA cleavage studies
  作者：Ramya V. Shingalapur、Kallappa M. Hosamani、Rangappa S. Keri、Mallinath H. Hugar

  DOI：10.1016/j.ejmech.2010.01.007

  日期：2010.5

  In seeking broad spectrum pharmacological activities of benzimidazole derivatives, a group of 4-thiazolidinones 5(a-j) and 1,3,4-oxadiazoles 6(a-j) containing 2-mercapto benzimidazole moiety were synthesized and screened for in vivo anticonvulsant activity by Maximal Electroshock (MES) model and antidiabetic activity using Oral Glucose Tolerance Test (OGTT). Compounds (5c), (5d), (5g) and (5i) exhibited potent anticonvulsant results and (6c), (6d), (6h) and (6i) showed excellent antidiabetic activities and also pharmacophore derived from active molecules suggested that presence of -OH group was a common feature in all active compounds. In DNA cleavage studies, compound (5d) cleaved DNA completely as no trace of DNA was found. On the other hand, a sharp streak was found for compounds (5c), (6a) and (6d). (C) 2010 Elsevier Masson SAS. All rights reserved.
• Naik; Patil; Tallur, Journal of the Indian Chemical Society, 2008, vol. 85, # 1, p. 22 - 25
  作者：Naik、Patil、Tallur、Mallur

  DOI：——

  日期：——
• Green route for the heterocyclization of 2-mercaptobenzimidazole into β-lactum segment derivatives containing –CONH– bridge with benzimidazole: Screening in vitro antimicrobial activity with various microorganisms
  作者：Krunal G. Desai、Kishor R. Desai

  DOI：10.1016/j.bmc.2006.09.017

  日期：2006.12

  The efficient and rapid synthesis of novel azetidin-2-ones 4a-j has been established. Thus, both microwave and conventional condensation 2-(1H-benzimidazol)-ylthio}-N'-2-(substituted phenyl) hydrazide with chloroacetylchloride were carried out in DMF-benzene solvent in the presence of Et3N catalyst. The microwave synthesis route afforded better yield with short time. The novel heterocycles were characterized by elemental analysis and spectral features. Some of the produced compounds were screened for their antimicrobial activity. (c) 2006 Elsevier Ltd. All rights reserved.