Synthesis, biological evaluation and docking study of 3-aroyl-1-(4-sulfamoylphenyl)thiourea derivatives as 15-lipoxygenase inhibitors

被引：51

作者：

Mahdavi, Mohammad ^{[1
,2
]}

Shirazi, Maryam Shahzad ^{[1
,2
]}

Taherkhani, Raana ^{[3
]}

Saeedi, Mina ^{[1
,2
]}

Alipour, Eskandar ^{[3
]}

Moghadam, Farshad Homayouni ^{[4
]}

Moradi, Alireza ^{[4
,5
]}

Nadri, Hamid ^{[4
,5
]}

Emami, Saeed ^{[6
,7
]}

Firoozpour, Loghman ^{[8
]}

Shafiee, Abbas ^{[1
,2
]}

Foroumadi, Alireza ^{[1
,2
,8
]}

机构：

[1] Univ Tehran Med Sci, Fac Pharm, Dept Med Chem, Tehran, Iran

[2] Univ Tehran Med Sci, Pharmaceut Sci Res Ctr, Tehran, Iran

[3] Islamic Azad Univ, Dept Chem, Tehran North Branch, Tehran, Iran

[4] Shahid Sadoughi Univ Med Sci, Sch Med, Neurobiomed Res Ctr, Yazd, Iran

[5] Shahid Sadoughi Univ Med Sci, Dept Med Chem, Fac Pharm, Yazd, Iran

[6] Mazandaran Univ Med Sci, Dept Med Chem, Fac Pharm, Sari, Iran

[7] Mazandaran Univ Med Sci, Pharmaceut Sci Res Ctr, Fac Pharm, Sari, Iran

[8] Univ Tehran Med Sci, Drug Design & Dev Res Ctr, Tehran, Iran

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2014年 / 82卷

基金：

美国国家科学基金会;

关键词：

Thiourea; Sulfonamides; Enzyme inhibitors; 15-Lipoxygenase; Antioxidant activity; Docking study; SULFONAMIDES; THIOUREA; TRANSMEMBRANE; MOIETIES; DESIGN; POTENT;

D O I：

10.1016/j.ejmech.2014.05.054

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of 3-aroyl-1-(4-sulfamoylphenyl)thiourea derivatives containing sulfonamide moiety were designed and synthesized as 15-lipoxygenase (15-LOX) inhibitors. Most synthesized compounds showed potent activity against soybean 15-LOX with IC50 values less than 25 mu M. The most potent compound 4c (3-methylbenzoyl derivative) with IC50 value of 1.8 mu M was 10-fold more potent than quercetin. Interestingly, compound 4c also showed the highest antioxidant activity, as determined by ferric reducing antioxidant power (FRAP) assay. Its capacity for reducing ferric ion was more than ascorbic acid. The viability assay of the selected compound 4c against oxidative stress-induced cell death in differentiated PC12 cells revealed that compound 4c significantly protected neurons against cell death in low concentrations. (C) 2014 Elsevier Masson SAS. All rights reserved.

引用

页码：308 / 313

页数：6

共 50 条

[1] Synthesis of novel hybrid pharmacophore of N-((4-sulfamoylphenyl)carbamothioyl)alkanamides as potent carbonic anhydrase-II and 15-lipoxygenase inhibitors
Saeed, Aamer
Khan, Shafi Ullah
Saeed, Maria
Shabir, Ghulam
Hasan, Abbas
Khera, Rasheed Ahmad
El-Seedi, Hesham
Halim, Sobia Ahsan
Khan, Ajmal
Al-Harrasi, Ahmed
Iqbal, Jamshed
DRUG DEVELOPMENT RESEARCH, 2022, 83 (03) : 745 - 754
[2] Synthesis, Biological Evaluation, and Molecular Dynamics of Carbothioamides Derivatives as Carbonic Anhydrase II and 15-Lipoxygenase Inhibitors
Channar, Pervaiz Ali
Alharthy, Rima. D. D.
Ejaz, Syeda Abida
Saeed, Aamer
Iqbal, Jamshed
MOLECULES, 2022, 27 (24):
[3] Design, synthesis, and SAR study of isopropoxy allylbenzene derivatives as 15-lipoxygenase inhibitors
Mousavian, Mina
Alavi, Seyed Jamal
Rahbarian, Raheleh
Rajabian, Majid
Orafai, Hossein M.
Sadeghian, Hamid
IRANIAN JOURNAL OF BASIC MEDICAL SCIENCES, 2020, 23 (08) : 984 - 989
[4] Synthesis and Biological Evaluation of 4-Sulfamoylphenyl/Sulfocoumarin Carboxamides as Selective Inhibitors of Carbonic Anhydrase Isoforms hCAII, IX, and XII
Angapelly, Srinivas
Angeli, Andrea
Khan, Arbaj Jabbar
Ramya, P. V. Sri
Supuran, Claudiu T.
Arifuddin, Mohammed
CHEMMEDCHEM, 2018, 13 (12) : 1165 - 1171
[5] Phthalimide analogs as probable 15-lipoxygenase-1 inhibitors: synthesis, biological evaluation and docking studies
Alireza Aliabadi
Ahmad Mohammadi-Farani
Zeinab Hosseinzadeh
Hamid Nadri
Alireza Moradi
Farahnaz Ahmadi
DARU Journal of Pharmaceutical Sciences, 23
[6] Phthalimide analogs as probable 15-lipoxygenase-1 inhibitors: synthesis, biological evaluation and docking studies
Aliabadi, Alireza
Mohammadi-Farani, Ahmad
Hosseinzadeh, Zeinab
Nadri, Hamid
Moradi, Alireza
Ahmadi, Farahnaz
DARU-JOURNAL OF PHARMACEUTICAL SCIENCES, 2015, 23
[7] Biological Evaluation and Molecular Docking Study of 3-(4-Sulfamoylphenyl)-4-phenyl-1H-pyrrole-2,5-dione as COX-2 Inhibitor
Van Chung Pham
Shin, Ji-Sun
Choi, Min Ji
Kim, Tae Woo
Lee, Kijae
Kim, Kyung Ju
Huh, Geun
Kim, Jungahn
Choo, Dong Joon
Lee, Kyung-Tae
Lee, Jae Yeol
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2012, 33 (02) : 721 - 724
[8] Design and synthesis of pyrimido[4,5-b][1,4]benzothiazine derivatives, as potent 15-lipoxygenase inhibitors
Bakavoli, M.
Nikpour, M.
Rahimizadeh, M.
Saberi, M. R.
Sadeghian, H.
BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (05) : 2120 - 2126
[9] Synthesis and SAR study of 4,5-diaryl-1H-imidazole-2(3H)-thione derivatives, as potent 15-lipoxygenase inhibitors
Assadieskandar, Amir
Amini, Mohsen
Salehi, Marjan
Sadeghian, Hamid
Alimardani, Maliheh
Sakhteman, Amirhossein
Nadri, Hamid
Shafiee, Abbas
BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (24) : 7160 - 7166
[10] Design, synthesis, molecular modelling and biological evaluation of novel 3-(2-naphthyl)-1-phenyl-1H-pyrazole derivatives as potent antioxidants and 15-Lipoxygenase inhibitors
Ali, Sahar A.
Awad, Samir Mohamed
Said, Ahmed Mohammed
Mahgoub, Shahenda
Taha, Heba
Ahmed, Naglaa Mohamed
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2020, 35 (01) : 847 - 863

← 1 2 3 4 5 →