2-((4-fluorophenoxy)methyl)-1-methyl-1H-benzo[d]imidazole | 324579-81-9

• 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-fluorophenoxy)methyl)-1-methyl-1H-benzo[d]imidazole
• 英文别名: 2-(4-Fluoro-phenoxymethyl)-1-methyl-1H-benzoimidazole；2-[(4-fluorophenoxy)methyl]-1-methylbenzimidazole
• CAS: 324579-81-9
• 化学式: C₁₅H₁₃FN₂O
• mdl: MFCD01794578
• 分子量: 256.279
• InChiKey: UELQPMYVOWTTFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(氯甲基)-1-甲基-1H-苯并咪唑 、 4-氟苯酚 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 8.0h， 生成 2-((4-fluorophenoxy)methyl)-1-methyl-1H-benzo[d]imidazole
  参考文献：
  名称：

  Synthesis and Antifungal Activity of 2-Chloromethyl-1H-benzimidazole Derivatives against Phytopathogenic Fungi in Vitro

  摘要：

  A series of 35 benzimidazole derivatives were synthesized from 2-chloromethyl-1H-benzimidazole in good yields. Their structures were characterized by H-1 and C-13 NMR and HRESIMS. Antifungal activities of all of the synthesized compounds were evaluated against five phytopathogens fungi (Cytospora sp., Colletotrichum gloeosporioides, Botrytis cinerea, Alternaria solani, and Fusarium solani) using the mycelium growth rate method. Compound 4m displayed strong growth inhibition of C. gloeosporioides, A. solani, and F. solani with IC50 of 20.76, 27.58, and 18.60 mu g/mL, respectively. Selective inhibition of B. cinerea instead of the other fungal pathogenes was observed with 7f (IC50 of 13.36 mu g/mL), comparable to that of positive control, a commercial agricultural fungicide hymexazol (IC50 of 8.92 mu g/mL). Compound 51) exhibited remarkable antifungal properties against Cytospora sp., C. gloeosporioides, B. cinerea, and F. solani with IC50 values of 30.97, 11.38, 57.71, and 40.15 mu g/mL, respectively; among the target fungi, 5b was the most active compound and superior to the reference against C. gloeosporioides alone. Structure-activity relationship (SAR) data of these compounds are as follows: (1) introduction of the, chlorine atom on para-position in the benzene ring help to increase activity (4f vs 4c; 7f vs 7n), (2) the sulfonyl group is critical for the inhibition of C. gloeosporioides (51) and 5c vs 5a), and (3) the unsubstituted benzene ring improve activity (4m vs 4n, 4e and 4a). Thus, compounds 5b, 4m, and 7f emerged as a new leading structure for the development of new fungicides.

  DOI：

  10.1021/jf3053934

文献信息

• Compounds that enhance Atoh-1 expression
  申请人：MASSACHUSETTS EYE & EAR INFIRMARY

  公开号：EP2732819A2

  公开（公告）日：2014-05-21

  This invention generally provides compounds, pharmaceutical compositions, and methods for their use, which include methods that result in increased expression in an Atoh1 gene (e.g., Hath1) in a biological cell. More specifically, the invention relates to the treatment of diseases and/or disorders that would benefit from increased Atoh1 expression, e.g. a hearing impairment or imbalance disorder associated with a loss of auditory hair cells, or a disorder associated with abnormal cellular proliferation.

  本发明一般提供化合物、药物组合物及其使用方法，其中包括导致生物细胞中 Atoh1 基因（如 Hath1）表达增加的方法。更具体地说，本发明涉及可从 Atoh1 表达增加中获益的疾病和/或失调症的治疗，例如与听觉毛细胞丧失有关的听力损伤或失调症，或与细胞异常增殖有关的失调症。
• Compounds that enhance Atoh1 expression
  申请人：Massachusetts Eye & Ear Infirmary

  公开号：US10406163B2

  公开（公告）日：2019-09-10

  This invention generally provides compounds, pharmaceutical compositions, and methods for their use, which include methods that result in increased expression in an Atoh1 gene (e.g., Hath1) in a biological cell. More specifically, the invention relates to the treatment of diseases and/or disorders that would benefit from increased Atoh1 expression, e.g., a hearing impairment or imbalance disorder associated with a loss of auditory hair cells, or a disorder associated with abnormal cellular proliferation.

  本发明一般提供化合物、药物组合物及其使用方法，其中包括导致生物细胞中Atoh1基因（如Hath1）表达增加的方法。更具体地说，本发明涉及可从 Atoh1 表达增加中获益的疾病和/或失调症的治疗，例如，与听觉毛细胞丧失有关的听力损伤或失调症，或与细胞异常增殖有关的失调症。
• COMPOUNDS THAT ENHANCE ATOH-1 EXPRESSION
  申请人：Massachusetts Eye & Ear Infirmary

  公开号：EP2254572B1

  公开（公告）日：2013-10-16
• METHODS AND COMPOSITIONS FOR REGENERATING HAIR CELLS AND/OR SUPPORTING CELLS
  申请人：Massachusetts Eye & Ear Infirmary

  公开号：EP2892523B1

  公开（公告）日：2019-05-01
• EFFICIENT DELIVERY OF THERAPEUTIC MOLECULES TO CELLS OF THE INNER EAR
  申请人：Massachusetts Eye and Ear Infirmary

  公开号：EP3212773B1

  公开（公告）日：2021-09-15