Synthesis and biological evaluation of novel 2-(substituted isoxazol-4-yl)-5-arylamino-1,3,4-oxadiazoles

被引:17
作者
Liu, Feng [1 ]
Wang, Meiyan [2 ]
Teng, Xinhuan [1 ]
Zhang, Peizhi [2 ]
Jiang, Lin [2 ]
机构
[1] Shandong Agr Univ, Coll Plant Protect, Tai An 271018, Shandong, Peoples R China
[2] Shandong Agr Univ, Coll Chem & Mat Sci, Tai An 271018, Shandong, Peoples R China
关键词
1,3,4-Oxadiazole; Isoxazole; Synthesis; Antifungal activity; DERIVATIVES; ANALOGS;
D O I
10.1007/s11164-013-1062-y
中图分类号
O6 [化学];
学科分类号
070301 [无机化学];
摘要
A series of 2-(5-methyl-3-(4-chloro/trifluoromethylphenyl)isoxazol-4-yl)-5-arylamino-1,3,4-oxadiazoles were synthesized from 4-chloro/trifluoromethyl benzaldehyde, ethyl acetoacetate, hydroxylamine hydrochloride, hydrazine hydrate, and aryl isocyanate by multi-step reactions. The structures of the target compounds were elucidated by IR, H-1 NMR, MS, and elemental analysis. All these compounds were tested for in vitro antifungal activities against Botrytis cinerea and Rhizoctonia cerealis by the mycelium growth rate method, and the results indicated that some compounds displayed high antifungal activity against Botrytis cinerea.
引用
收藏
页码:1575 / 1581
页数:7
相关论文
共 15 条
[1]
Synthesis of substituted acridinyl pyrazoline derivatives and their evaluation for anti-inflammatory activity [J].
Chandra, Trilok ;
Garg, Neha ;
Lata, Suman ;
Saxena, K. K. ;
Kumar, Ashok .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (05) :1772-1776
[2]
An enantioselective synthesis of insecticidal 4-alkynyloxazolines [J].
Clark, D ;
Travis, DA .
BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (11) :2857-2862
[3]
Synthesis and Antifungal Activity of Novel 2-(1H-Benzimidazol-2-yl)-5-substituted-1,3,4-oxadiazole Derivatives [J].
Ji, Zengchen ;
Liu, Feng ;
Zhang, Zeyuan ;
Li, Fubo ;
Jiang, Lin .
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2012, 32 (11) :2129-2133
[4]
Synthesis of novel 1,2,4-oxadiazoles and analogues as potential anticancer agents [J].
Kumar, Dalip ;
Patel, Gautam ;
Chavers, Angela K. ;
Chang, Kuei-Hua ;
Shah, Kavita .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (07) :3085-3092
[5]
Heterocyclic nucleoside analogues: Design and synthesis of antiviral, modified nucleosides containing isoxazole heterocycles [J].
Lee, YS ;
Kim, BH .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (10) :1395-1397
[6]
Synthesis of 2-amino-6-oxocyclohexenylsulfonamides and their activity against Botrytis cinerea [J].
Li, Xing-Hai ;
Ji, Ming-Shan ;
Qi, Zhi-Qiu ;
Li, Xiu-Wei ;
Shen, Yu-Xia ;
Gu, Zu-Min ;
Zhang, Yang ;
Wei, Song-Hong ;
Wang, Ying-Zi ;
Wang, Dao-Quan .
PEST MANAGEMENT SCIENCE, 2011, 67 (08) :986-992
[7]
[刘俊芝 LIU Junzhi], 2007, [合成化学, Chinese Journal of Synthetic Chemistry], V15, P204
[8]
Design, Synthesis, and Herbicidal Activities of Novel 2-Cyanoacrylates Containing Isoxazole Moieties [J].
Liu, Yuxiu ;
Cui, Zhipeng ;
Bin Liu ;
Cai, Baoli ;
Li, Yonghong ;
Wang, Qingmin .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2010, 58 (05) :2685-2689
[9]
Synthesis and evaluation of antioxidant and antibacterial activities of new substituted bis(1,3,4-oxadiazoles), 3,5-bis(substituted) pyrazoles and isoxazoles [J].
Musad, Ebraheem Abdu ;
Mohamed, Riyaz ;
Saeed, Bahjat Ali ;
Vishwanath, Bannikuppe S. ;
Rai, K. M. Lokanatha .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (12) :3536-3540
[10]
Synthesis and microbial inhibition study of novel 5-imidazolyl substituted isoxazolidines [J].
Sadashiva, MP ;
Mallesha, H ;
Hitesh, NA ;
Rangappa, KS .
BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (24) :6389-6395