Zhang Jin, Peng Ju-Fang, Wang Tao, Kang Yang, Jing Sisi, Zhang Zun-Ting
Key Laboratory of the Ministry of Education for Medicinal Resources and Natural Pharmaceutical Chemistry, National Engineering Laboratory for Resource Development of Endangered Crude Drugs in Northwest of China, and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an, 710062, People's Republic of China.
Mol Divers. 2017 May;21(2):317-323. doi: 10.1007/s11030-017-9727-x. Epub 2017 Feb 28.
3-phenol-1H-pyrazoles (2), 4-halogeno-3-phenol-1H-pyrazoles (3) and 2-(1-phenol-1H-pyrazol-5-yl)phenols (4) were prepared by the condensation of (E)-3-(dimethylamino)-1-phenylprop-2-en-1-ones and hydrazine hydrate or phenylhydrazine in good yields. They were evaluated against five phytopathogens fungi, namely Cytospora sp., Colletotrichum gloeosporioides, Botrytis cinerea, Alternaria solani and Fusarium solani in vitro. Most of the above-mentioned compounds exhibited activities. For example, 4-chloro-2-(1H-pyrazol-3-yl)phenol (3k) and 4-bromo-3-phenol-1H-pyrazole (3b) showed good and broad-spectrum antifungal properties against Cytospora sp., C. gloeosporioides, Botrytis cinerea, Alternaria solani and F. Solani with [Formula: see text] values ranging from 4.66 to 12.47 [Formula: see text]g/mL. The results showed that pyrazoles with one aryl group at 3-position (2 and 3) exhibited better antibacterial activity than those with two aryl substituents (4). In addition, the existence of an electron-withdrawing group, a substituent on the ortho-position of phenol ring or a halogen atom at the 4-position of the pyrazole enhanced the antifungal activity of pyrazoles 2 and 3. A series of arylpyrazole derivatives was facilely prepared and was evaluated against five phytopathogens fungi including Cytospora sp., Colletotrichum gloeosporioides, Botrytis cinerea, Alternaria solani, and Fusarium solani in vitro. Most of those compounds exhibited remarkable antifungal activities and were superior to the positive control hymexazol.
通过（E）-3-（二甲基氨基）-1-苯基丙-2-烯-1-酮与水合肼或苯肼缩合，以良好产率制备了3-苯酚-1H-吡唑（2）、4-卤代-3-苯酚-1H-吡唑（3）和2-（1-苯酚-1H-吡唑-5-基）苯酚（4）。对它们进行了体外抗五种植物病原真菌的评估，这五种真菌分别是壳囊孢属真菌、炭疽菌、灰葡萄孢、链格孢和茄病镰刀菌。上述大多数化合物都表现出活性。例如，4-氯-2-（1H-吡唑-3-基）苯酚（3k）和4-溴-3-苯酚-1H-吡唑（3b）对壳囊孢属真菌、炭疽菌、灰葡萄孢、链格孢和茄病镰刀菌表现出良好的广谱抗真菌特性，其最低抑菌浓度值在4.66至12.47μg/mL范围内。结果表明，在3-位带有一个芳基的吡唑（2和3）比带有两个芳基取代基的吡唑（4）表现出更好的抗菌活性。此外，吸电子基团的存在、酚环邻位的取代基或吡唑4-位的卤原子增强了吡唑2和3的抗真菌活性。一系列芳基吡唑衍生物被简便地制备出来，并在体外对包括壳囊孢属真菌、炭疽菌、灰葡萄孢、链格孢和茄病镰刀菌在内的五种植物病原真菌进行了评估。这些化合物中的大多数都表现出显著的抗真菌活性，并且优于阳性对照恶霉灵。
