(9ci)-1,5-二甲基-1H-苯并咪唑-2-甲醇 | 68426-72-2

• 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: (9ci)-1,5-二甲基-1H-苯并咪唑-2-甲醇
• 英文名称: (N-methyl-5-methyl-1H-benzimidazole-2-yl)methanol
• 英文别名: (1,5-dimethyl-1H-benzoimidazol-2-yl)-methanol；(1,5-dimethyl-1H-benzimidazol-2-yl)methanol；(1,5-dimethylbenzimidazol-2-yl)methanol
• CAS: 68426-72-2
• 化学式: C₁₀H₁₂N₂O
• mdl: MFCD08691905
• 分子量: 176.218
• InChiKey: GLLWHKGUVVPVPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  (9ci)-1,5-二甲基-1H-苯并咪唑-2-甲醇 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以61%的产率得到1,5-二甲基-1H-苯并咪唑-2-甲醛
  参考文献：
  名称：

  Cytotoxicity of Substituted Benzimidazolyl Curcumin Mimics Against Multi-Drug Resistance Cancer Cell

  摘要：

  DOI：

  10.5012/bkcs.2013.34.4.1272
• 作为产物：
  描述：

  3,4-二氨基甲苯 在 盐酸 、 sodium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 反应 27.5h， 生成 (9ci)-1,5-二甲基-1H-苯并咪唑-2-甲醇
  参考文献：
  名称：

  选定的苯并咪唑衍生物作为潜在抗菌剂的合成与评价。

  摘要：

  合成了53个苯并咪唑衍生物的文库，它们在1、2和5位具有取代基，并针对一系列与医学相关的细菌和真菌参考菌株进行了筛选。SAR分析最有前景的结果表明，化合物的抗菌活性取决于与双环杂环相连的取代基。特别是，某些化合物对两种耐甲氧西林的金黄色葡萄球菌（MRSA）菌株表现出抗菌活性，其最低抑制浓度（MIC）与广泛使用的环丙沙星药物相当。这些化合物具有一些共同特征。三个具有5-卤素取代基；两个是（S）-2-乙胺苯并咪唑的衍生物；其他是一种2-（氯甲基）-1H-苯并[d]咪唑和（1H-苯并[d]咪唑-2-基）甲硫醇的衍生物。抗真菌筛选的结果也非常有趣：23种化合物对选定的真菌菌株显示出有效的杀真菌活性。它们的MIC值显示出比两性霉素B相同或更高的效力。5-卤代苯并咪唑衍生物被认为是有前途的广谱抗微生物候选物，值得进一步研究以用于潜在的治疗应用。

  DOI：

  10.3390/molecules200815206

文献信息

• Non-basic melanin concentrating hormone receptor-1 antagonists
  申请人：Ahmad Saleem

  公开号：US20070093508A1

  公开（公告）日：2007-04-26

  The present application provides compounds, including all stereoisomers, solvates, prodrugs and pharmaceutically acceptable forms thereof according to Formula I. Additionally, the present application provides pharmaceutical compositions containing at least one compound according to Formula I and optionally at least one additional therapeutic agent. Finally, the present application provides methods for treating a patient suffering from an MCHR-1 modulated disease or disorder such as, for example, obesity, diabetes, depression or anxiety by administration of a therapeutically effective dose of a compound according to Formula I.

  本申请提供了根据式I提供的化合物，包括所有立体异构体、溶剂合物、前药和药学上可接受的形式。此外，本申请提供了含有至少一种根据式I的化合物和可选至少一种额外治疗剂的药物组合物。最后，本申请提供了治疗患有MCHR-1调节性疾病或紊乱（例如肥胖症、糖尿病、抑郁症或焦虑症）的患者的方法，通过给予根据式I的化合物的治疗有效剂量。
• Synthesis and Pharmacological Activity of C(2)-Substituted Benzimidazoles
  作者：O. N. Zhukovskaya、A. A. Spasov、D. S. Yakovlev、V. A. Kosolapov、D. V. Mal’tsev、A. S. Morkovnik、V. A. Babkova、A. A. Brigadirova、Ya. V. Agatsarskaya、A. S. Taran、M. V. Miroshnikov、K. T. Sultanova、V. I. Kornilov、V. A. Anisimova

  DOI：10.1007/s11094-019-01979-0

  日期：2019.6.15

  The antiglycation activities of 2-(morpholin-4-yl)-1-(propen-2-en-1-yl)-1H-benzimidazole and 2-(morpholin-4-yl)-1-[2-(morpholin-4-yl)ethyl]-1H-benzimidazole were comparable to that of aminoguanidine. Some compounds exhibited moderate antiserotonin, anti-angiotensin, antioxidant, and dipeptidyl peptidase-4 (DPP-4) inhibitory effects.

  合成了一系列含有2-吡咯烷甲基和2-哌嗪甲基以及2-吗啉代和2-吗啉代乙胺取代基的新化合物。2-(morpholin-4-yl)-1-(propen-2-en-1-yl)-1H-苯并咪唑和2-(morpholin-4-yl)-1-[2-(morpholin- 4-基)乙基]-1H-苯并咪唑与氨基胍相当。一些化合物表现出中等的抗血清素、抗血管紧张素、抗氧化和二肽基肽酶 4 (DPP-4) 抑制作用。
• New ( E )-1-alkyl-1 H -benzo[ d ]imidazol-2-yl)methylene)indolin-2-ones: Synthesis, in vitro cytotoxicity evaluation and apoptosis inducing studies
  作者：Pankaj Sharma、Dinesh Thummuri、T. Srinivasa Reddy、Kishna Ram Senwar、V.G.M. Naidu、Gannoju Srinivasulu、Suresh K. Bharghava、Nagula Shankaraiah

  DOI：10.1016/j.ejmech.2016.07.019

  日期：2016.10

  A new series of (E)-benzo[d]imidazol-2-yl)methylene)indolin-2-one derivatives has been synthesized and evaluated for their in vitro cytotoxic activity against a panel of selected human cancer cell lines of prostate (PC-3 and DU-145) and breast (BT-549, MDA-MB-231, MCF-7, 4T1), non-small lung (A549) and gastric (HGC) cancer cells along with normal breast epithelial cells (MCF10A). Among the tested compounds, 81 showed significant cytotoxic activity against MDA-MB-231 and 4T1 cancer cells with IC50 values of 3.26 +/- 0.24 mu M and 5.96 +/- 0.67 mu M respectively. The compounds 8f, 8i, 8l and 8o were also screened on normal human breast epithelial cells (MCF10A) and found to be safer with lesser cytotoxicity. The treatment of MDA-MB-231 cells with 81 led to inhibition of cell migration ability through disruption of F-actin protein assembly. The flow-cytometry analysis reveals that the cells arrested in G0/G1 phase of the cell cycle. Further, the compound 81 induced apoptosis of MDA-MB-231 cells was characterized by different staining techniques such as Acridine Orange/Ethidium Bromide (AO/EB), DAPI, annexin V-FITC/PI, Rhodamine-123 and MitoSOX red assay. Western blot studies demonstrated that the compound 81 treatment led to activation of caspase-3, increased expression of cleaved PARP, increased expression of pro-apoptotic Bax and decreased expression of anti-apoptotic Bcl-2 in MDA-MB-231 cancer cells. (C) 2016 Elsevier Masson SAS. All rights reserved.
• Investigations of unsaturated azoles. 15. Synthesis and reactions of acylated benzimidazoles
  作者：I. I. Popov、A. A. Zubenko

  DOI：10.1007/bf02253109

  日期：1997.3
• Synthesis of substituted benzimidazolyl curcumin mimics and their anticancer activity
  作者：Ho Bum Woo、Young Woo Eom、Kyu-Sang Park、Jungyeob Ham、Chan Mug Ahn、Seokjoon Lee

  DOI：10.1016/j.bmcl.2011.12.074

  日期：2012.1

  A novel curcumin mimic library (14a-14h and 15a-15h) possessing variously substituted benzimidazole groups was synthesized through the aldol reaction of (E)-4-(4-hydroxy-3-methoxyphenyl)but-3-en-2-one (7) or (E)-4-(3-hydroxy-4-methoxyphenyl)but-3-en-2-one (13) with diversely substituted benzimidazolyl-2-carbaldehyde (12a-12h). The MTT assay of the cancer cells MCF-7, SH-SY5Y, HEP-G2, and H460 showed that compound 14c with IC50 of 1.0 and 1.9 mu M has a strong inhibitory effect on the growth of SH-SY5Y and Hep-G2 cells, respectively, and that compound 15h with IC50 of 1.9 mu M has a strong inhibitory effect on the growth of MCF-7 cancer cells. (C) 2011 Elsevier Ltd. All rights reserved.