Synthesis, Structural Determination, and Antifungal Activity of Novel Fluorinated Quinoline Analogs

被引：5

作者：

Sun, Xinpeng ^{[1
,2
]}

Yu, Wei ^{[1
,2
]}

Min, Lijing ^{[3
]}

Han, Liang ^{[2
]}

Hua, Xuewen ^{[4
]}

Shi, Jianjun ^{[5
]}

Sun, Nabo ^{[1
]}

Liu, Xinghai ^{[2
]}

机构：

[1] Zhejiang Shuren Univ, Coll Biol & Environm Engn, Hangzhou 310015, Peoples R China

[2] Zhejiang Univ Technol, Coll Chem Engn, Hangzhou 310014, Peoples R China

[3] Huzhou Univ, Coll Life Sci, Key Lab Vector Biol & Pathogen Control Zhejiang Pr, Huzhou 313000, Peoples R China

[4] Liaocheng Univ, Coll Agr, Liaocheng 252000, Peoples R China

[5] Huangshan Univ, Coll Chem & Chem Engn, Huangshan 245041, Peoples R China

来源：

MOLECULES | 2023年 / 28卷 / 08期

关键词：

fluorinated quinoline; synthesis; antifungal activity; DERIVATIVES; DESIGN; ANTIBACTERIAL; SAR;

D O I：

10.3390/molecules28083373

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A series of new fluorinated quinoline analogs were synthesized using Tebufloquin as the lead compound, 2-fluoroaniline, ethyl 2-methylacetoacetate, and substituted benzoic acid as raw materials. Their structures were confirmed by H-1 NMR, C-13 NMR, and HRMS. The compound 8-fluoro-2,3-dimethylquinolin-4-yl 4-(tert-butyl)benzoate (2b) was further determined by X-ray single-crystal diffraction. The antifungal activity was tested at 50 mu g/mL, and the bioassay results showed that these quinoline derivatives had good antifungal activity. Among them, compounds 2b, 2e, 2f, 2k, and 2n exhibited good activity (>80%) against S. sclerotiorum, and compound 2g displayed good activity (80.8%) against R. solani.

引用

页数：10

共 50 条

[11] Synthesis and Fungicidal Activity of a Series of Fluorinated Quinoline Amide Compounds
Ni, Yun
Xu, Tianming
Zhong, Liangkun
Kong, Xiaoyan
Shi, Jianjun
Liu, Xinghai
Kong, Xiaolin
Ji, Wenjuan
Tan, Chengxia
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2015, 35 (10) : 2218 - 2222
[12] Synthesis and structural optimization of antifungal kanamycin B analogs
Fosso, Marina Y.
Kawasaki, Yukie
Shrestha, Sanjib
Takemoto, Jon
Chang, Tom C. -W.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
[13] Synthesis, structural, biocomputational modeling and antifungal activity of novel armed pyrazoles
Titi, Abderrahim
Touzani, Rachid
Moliterni, Anna
Ben Hadda, Taibi
Messali, Mouslim
Benabbes, Redouanae
Berredjem, Malika
Bouzina, Abdeslem
Al-Zaqri, Nabil
Taleb, Mustapha
Zarrouk, Abdelkader
Warad, Ismail
JOURNAL OF MOLECULAR STRUCTURE, 2022, 1264
[14] SYNTHESIS AND ANTIFUNGAL ACTIVITY OF FR109615-ANALOGS
OHKI, H
INAMOTO, Y
KAWABATA, K
KAMIMURA, T
SAKANE, K
JOURNAL OF ANTIBIOTICS, 1991, 44 (05): : 546 - 549
[15] Novel structural hybrids of quinoline and thiazole moieties: Synthesis and evaluation of antibacterial and antifungal activities with molecular modeling studies
Eissa, Sally, I
Farrag, Amel M.
Abbas, Samir Y.
El Shehry, Mohamed F.
Ragab, Ahmed
Fayed, Eman A.
Ammar, Yousry A.
BIOORGANIC CHEMISTRY, 2021, 110
[16] THE SYNTHESIS AND BIOLOGICAL-ACTIVITY OF FLUORINATED ANALOGS OF VITAMIN-A
BARUA, AB
OLSON, JA
FEDERATION PROCEEDINGS, 1981, 40 (06) : 1803 - 1803
[17] SYNTHESIS AND ANALGESIC ANTIINFLAMMATORY ACTIVITY OF CERTAIN FLUORINATED CINCHOPHEN ANALOGS
ABOULENEIN, HY
IBRAHIM, SE
JOURNAL OF FLUORINE CHEMISTRY, 1992, 59 (02) : 233 - 237
[18] SYNTHESIS AND ANTITHYROID ACTIVITY OF FLUORINATED 2-THIOURACIL ANALOGS
ABOULENEIN, HY
ALANDIS, NM
JOURNAL OF ENZYME INHIBITION, 1993, 7 (03): : 197 - 202
[19] Synthesis, Structural Studies and Molecular Modelling of a Novel Imidazoline Derivative with Antifungal Activity
Wrobel, Tomasz M.
Kosikowska, Urszula
Kaczor, Agnieszka A.
Andrzejczuk, Sylwia
Karczmarzyk, Zbigniew
Wysocki, Waldemar
Urbanczyk-Lipkowska, Zofia
Morawiak, Maja
Matosiuk, Dariusz
MOLECULES, 2015, 20 (08) : 14761 - 14776
[20] Synthesis and neurotropic activity of novel quinoline derivatives
Lukevics, E
Segal, I
Zablotskaya, A
Germane, S
MOLECULES, 1997, 2 (12) : 180 - 185

← 1 2 3 4 5 →