Ultrasound-promoted synthesis and immunosuppressive activity of novel quinazoline derivatives

被引：15

作者：

Zhang, Lei ^{[1
]}

Gao, Zhe ^{[2
]}

Peng, Chen ^{[1
]}

Bin, Zheng-Yang ^{[1
]}

Zhao, Dan ^{[1
]}

Wu, Jing ^{[1
]}

Xu, Qiang ^{[2
]}

Li, Jian-Xin ^{[1
]}

机构：

[1] Nanjing Univ, Sch Chem & Chem Engn, State Key Lab Analyt Chem Life Sci, Nanjing 210093, Jiangsu, Peoples R China

[2] Nanjing Univ, Sch Life Sci, State Key Lab Pharmaceut Biotechnol, Nanjing 210093, Jiangsu, Peoples R China

来源：

MOLECULAR DIVERSITY | 2012年 / 16卷 / 03期

基金：

中国国家自然科学基金;

关键词：

Immunosuppressive activity; Bischler cyclization; Ultrasound irradiation; SAR; Quinazoline; CYCLOSPORINE-A; B-CELL; ANTIMALARIAL ACTIVITIES; BIOLOGICAL EVALUATION; RHEUMATOID-ARTHRITIS; NO PRODUCTION; INHIBITORS; MECHANISM; AGENTS; ACTIVATION;

D O I：

10.1007/s11030-012-9390-1

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：

An environmentally friendly and mild Bischler cyclization was developed to access quinazolines with diverse substitution. Based on this method, a library of 53 quinazoline derivatives was prepared and tested in vitro for cytotoxicity and inhibition on T-cell and B-cell proliferation. Compounds 6b, 7b, 17b, 33, and 35 showed higher inhibitory activity on both T-cell and B-cell proliferations, with IC50 values of 6.16, 6.30, 5.43, 2.54, and 9.80 mu M on T-cell, respectively. All the tested compounds showed no obvious cytotoxicity at 10 mu M concentration. The preliminary structure-activity relationship was concluded revealing that 4-position is the key modification site for potent quinazoline immunosuppressive agent.

引用

收藏

页码：579 / 590

页数：12

相关论文

共 50 条

[21] Synthesis and antitumor activity of novel quinazoline derivatives containing thiosemicarbazide moiety [J].

He, Junbo ;

Wang, Xiaoguo ;

Zhao, Xiaoqin ;

Liang, YongJu ;

He, Hongwu ;

Fu, Liwu .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 54 :925-930

[22] Synthesis, analgesic and anti-inflammatory evaluation of some novel quinazoline derivatives [J].

Alafeefy, Ahmed M. ;

Kadi, Adnan A. ;

Al-Deeb, Omar A. ;

El-Tahir, Kamal E. H. ;

Al-jaber, Nabila A. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (11) :4947-4952

[23] Design, Synthesis, Anticancer Activity, and Cell Cycle Analysis of Novel Quinazoline Derivatives Targeting VEGFR-2 Kinase [J].

Ahmed, Marwa F. ;

Khalifa, Amany S. ;

Eed, Emad M. .

RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2021, 91 (12) :2497-2505

[24] Design and synthesis of novel quinazolinyl-bisspirooxindoles as potent anti-tubercular agents: an ultrasound-promoted methodology [J].

Allaka, Bhargava Sai ;

Basavoju, Srinivas ;

Rekha, Estharla Madhu ;

Sriram, Dharmarajan ;

Krishna, Gamidi Rama .

MOLECULAR DIVERSITY, 2023, 27 (03) :1427-1436

[25] Evaluation of Antibacterial Activity of Novel Quinazoline Derivatives [J].

Tiwari, Ravi ;

Chhabra, Gurmeet .

ASIAN JOURNAL OF CHEMISTRY, 2010, 22 (08) :5981-5986

[26] Synthesis and Antitumor and Antibacterial Activity of Novel Dihydronaphthaline and Dihydrobenzo[H]Quinazoline Derivatives [J].

Markosyan, A. I. ;

Airapetyan, K. K. ;

Gabrielyan, S. A. ;

Mamyan, S. S. ;

Shirinyan, V. Z. ;

Zakharov, A. V. ;

Arsenyan, F. G. ;

Avakimyan, Dzh. A. ;

Stepanyan, G. M. .

PHARMACEUTICAL CHEMISTRY JOURNAL, 2019, 53 (01) :15-22

[27] Synthesis and anticancer activity of new quinazoline derivatives [J].

Abuelizz, Hatem A. ;

Marzouk, Mohamed ;

Ghabbour, Hazem ;

Al-Salahi, Rashad .

SAUDI PHARMACEUTICAL JOURNAL, 2017, 25 (07) :1047-1054

[28] Linear and Cyclic Amides with a Thiophene Backbone: Ultrasound-Promoted Synthesis and Crystal Structures [J].

Ngo, Thien H. ;

Berndt, Huelya ;

Lentz, Dieter ;

Reissig, Hans-Ulrich .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (21) :9676-9683

[29] Synthesis and In vitro Anticancer Activity of Novel Quinazoline Derivatives Containing Thiosemicarbazone Structure [J].

Liu Haibin ;

Lu Ping ;

Pan Ningning ;

Ai Limei ;

Liu Yongxiang .

CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2014, 35 (05) :981-988

[30] ULTRASOUND-PROMOTED SYNTHESIS OF BIOLOGICALLY ACTIVE α-HYDROXYPHOSPHONATES/HYDROXYPHOSPHINATES USING 1,4-DIMETHYLPIPERAZINE AS A CATALYST [J].

Rasheed, S. ;

Ramana, K. Venkata ;

Madhava, G. ;

Rao, D. Subba ;

Raju, C. Naga .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2014, 189 (05) :606-614

← 1 2 3 4 5 →