2-((benzo[d][1,3]dioxol-5-yloxy)methyl)-1-methyl-1H-benzo[d]imidazole | 1425845-62-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 2-((benzo[d][1,3]dioxol-5-yloxy)methyl)-1-methyl-1H-benzo[d]imidazole
• 英文别名: 2-(1,3-Benzodioxol-5-yloxymethyl)-1-methylbenzimidazole；2-(1,3-benzodioxol-5-yloxymethyl)-1-methylbenzimidazole
• CAS: 1425845-62-0
• 化学式: C₁₆H₁₄N₂O₃
• 分子量: 282.299
• InChiKey: UEMTYOSMRHYJHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  芝麻酚 、 2-(氯甲基)-1-甲基-1H-苯并咪唑 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 8.0h， 以80%的产率得到2-((benzo[d][1,3]dioxol-5-yloxy)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

• Synthesis and Antifungal Activity of 2-Chloromethyl-1<i>H</i>-benzimidazole Derivatives against Phytopathogenic Fungi in Vitro
  作者：Yu-Bin Bai、An-Ling Zhang、Jiang-Jiang Tang、Jin-Ming Gao

  DOI：10.1021/jf3053934

  日期：2013.3.20

  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.