Synthesis and antifungal activity of camphoricacid-based thiourea derivatives

被引：0

作者：

Ma, Xian-Li ^{[1
,2
]}

Liu, Lu-Zhi ^{[1
]}

Duan, Wen-Gui ^{[1
]}

Shi, Xian-Chun ^{[1
]}

Li, Fang-Yao ^{[1
,2
]}

Hua, Zhong-Ze ^{[1
]}

机构：

[1] School of Chemistry and Chemical Engineering, Guangxi University, Nanning

[2] School of Pharmacy, Guilin Medical University, Guilin

来源：

Chemistry and Industry of Forest Products | 2015年 / 35卷 / 06期

关键词：

Antifungal activity; Camphoric acid; Synthesis; Thiourea;

D O I：

10.3969/j.issn.0253-2417.2015.06.012

中图分类号：

学科分类号：

摘要：

Ten novel camphoric acid-based thiourea compounds (5a-5j) were prepared using camphoric acid and aminoethyl substituted phenyl thioureas as starting materials. The target compounds were characterized by FT-IR, 1H NMR, 13C NMR, LC-MS, and elemental analysis. The antifungal activities of the compounds 5a-5j were tested. The preliminary bioassay showed that most of the target compounds exhibited certain antifungal activities, in which camphoric acid-based (o-methoxy)phenyl thiourea 5c (R=o-CH3O) and camphoric acid-based (m-methoxy)phenyl thiourea 5d (R=m-CH3O) had inhibition rate of 86.9% against Alternaria solani, and camphoric acid-based (m-methoxy)phenyl thiourea 5d, camphoric acid-based (m-methyl)phenyl thiourea 5 g (R=m-CH3) and camphoric acid-based (p-bromo)phenyl thiourea 4i (R=p-Br) had inhibition rate of 86.1% against Physalospora piricola at the concentration of 50 mg/L. In addition, compound 5i also had the best inhibitory activity against cercospora arachidicola (73.6%). © 2015, Editorial Board of «Chemistry and Industry of Forest Products». All right reserved.

引用

页码：69 / 77

页数：8

共 17 条

[1]

Zhang Z.-S., Wu J.-G., Deng R.-W., Preparation and properties of camphoric acid rare earth compounds, Journal of Lanzhou University: Natural Science Edition, 22, 1, pp. 124-125, (1986)

[2]

Boeckman R.K., Miller Y., Savage D., Et al., Total synthesis of a possible specific and effective acid-targeted cancer diagnostic, a camphor derived bis-N-oxide dimmer, Tetrahedron Letters, 52, 17, pp. 2243-2245, (2011)

[3]

Qin Z.-L., Li C., Synthesis and fungicidal activity of N'-(5-aryl-1,3,4-oxiadiazol-2-yl)-N-(sulfonylbenzoylimino) acetyl thiourea, Chinese Journal of Applied Chemistry, 26, 4, pp. 388-391, (2009)

[4]

Keche A.P., Hatnapure G.D., Tale R.H., Et al., A novel pyrimidine derivatives with aryl urea, thiourea and sulfonamide moieties: Synthesis, anti-inflammatory and antimicrobial evaluation, Bioorganic & Medicinal Chemistry Letters, 22, 10, pp. 3445-3448, (2012)

[5]

Yan M., Shi D.-Q., Synthesis and herbicidal activity of N-(4,6-disubstituted pyrimidin-2-yl)-N'-[-(heteroaryl)methyl-5-methyl-1H-1,2,3-triazol-4-ylcarbonyl] thiourea, Chinese Journal of Organic Chemistry, 28, 4, pp. 736-740, (2008)

[6]

Xu X.-Y., Qian X.-H., Li Z., Et al., Synthesis and insecticidal activity of new substituted -aryl-N'-benzoylthiourea compounds, Journal of Fluorine Chemistry, 121, 1, pp. 51-54, (2003)

[7]

Wei T.-B., Li M.-L., Lin Q., Et al., Microwave assisted synthesis and crystal structure of arylaldehyde-N-(1-phenyl-1H-tetrazole-5-yl)thiol acetyl hydrazones, Chinese Journal of Organic Chemistry, 26, 4, pp. 477-481, (2006)

[8]

Duan W.-G., Li X.-R., Mo Q.-J., Et al., Synthesis and herbicidal activity of 5-dehydroabietyl-1,3,4-oxadiazole derivatives, Holzforschung, 65, 2, pp. 191-197, (2011)

[9]

Xu X.-T., Ma X.-L., Duan W.-G., Et al., Synthesis and fungicidal activity of dehydroabietyl-1,2,4-triazolo-thiazolidinones, Holzforschung, 67, 1, pp. 107-112, (2013)

[10]

Ma X.-L., Chen L., Duan W.-G., Et al., Synthesis and herbicidal activity of alkanoic diacid dialkyl-didehydroabietyl-bis-oxadiazoles, Chinese Journal of Organic Chemistry, 31, 7, pp. 1069-1075, (2011)

← 1 2 →