Nano-SnCl4/SiO2 as a Catalyst for One-Pot Synthesis of Substituted 1H-Pyrazoles as Antifungal and Cytotoxic Agents

被引:3
作者
Khabnadideh, Soghra [1 ]
Faghih, Zeinab [1 ]
Zamani, Leila [1 ]
Zomorodian, Kamiar [2 ,3 ]
Mirjalili, Bi Bi Fatemesh [4 ]
Moradi, Hadi [1 ]
机构
[1] Shiraz Univ Med Sci, Pharmaceut Sci Res Ctr, Shiraz, Iran
[2] Shiraz Univ Med Sci, Sch Med, Ctr Basic Res Infect Dis, Shiraz, Iran
[3] Shiraz Univ Med Sci, Sch Med, Dept Med Mycol & Parasitol, Shiraz, Iran
[4] Yazd Univ, Coll Sci, Dept Chem, POB 89195-741, Yazd, Iran
关键词
Pyrazole; Nano-SnCl4/SiO2; antifungal; antibacterial; cytotoxic activity; antimicrobial activities; MOLECULAR DOCKING; PYRAZOLE; DERIVATIVES;
D O I
10.2174/1570178617666191127104622
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple and efficient method was developed for the synthesis of pyrazole derivatives via a one-pot reaction of 1,3-diketone and substituted hydrazines in the presence of nano-SnCl4/SiO2 as a mild catalyst. A series of some pyrazole derivatives (P1-P11) was synthesized and evaluated as antifungal and anti-cancer agents. Compounds P10 and P11 were demonstrated. The antimicrobial activities of the synthetic compounds showed that compounds P10 and P11 most excellently inhibited the growth of dermatophytes or Aspergillus species, respectively. Therefore, the cytotoxic activities of these compounds on two human cancer cell lines, A549 (lung cancer) and MCF-7 (breast cancer) were further assessed. Hence, results demonstrated that beside antifungal activity, P10 had also desirable cytotoxic effect on investigated cancerous cell lines, even higher than cisplatin.
引用
收藏
页码:459 / 465
页数:7
相关论文
共 21 条
[1]   Synthesis of novel pyrazole and dihydropyrazoles derivatives as potential anti-inflammatory and analgesic agents [J].
Abd-El Gawad, Nagwa M. ;
Georgey, Hanan H. ;
Ibrahim, Nashwa A. ;
Amin, Noha H. ;
Abdelsalam, Rania M. .
ARCHIVES OF PHARMACAL RESEARCH, 2012, 35 (05) :807-821
[2]   Synthesis and anti-inflammatory evaluation of new 1,3,5-triaryl-4,5-dihydro-1H-pyrazole derivatives possessing an aminosulphonyl pharmacophore [J].
Abdellatif, Khaled R. A. ;
Abdelgawad, Mohamed A. ;
Elshemy, Heba A. H. ;
Alsayed, Shahinda S. R. ;
Kamel, Gehan .
ARCHIVES OF PHARMACAL RESEARCH, 2015, 38 (11) :1932-1942
[3]   Synthesis and Antimicrobial Evaluation of some New Pyrazole, Pyrazoline and Chromeno[3,4-c]pyrazole Derivatives [J].
Abunada, Nada M. ;
Hassaneen, Hamdi M. ;
Abu Samaha, Ahmed S. M. ;
Miqdad, Omar A. .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2009, 20 (05) :975-987
[4]   Reactions between isocyanides and dialkyl acetylenedicarboxylates in the presence of 1,2-diacylhydrazines. One-pot synthesis of highly functionalized pyrazoles [J].
Adib, M ;
Sayahi, MH ;
Rahbari, S .
TETRAHEDRON LETTERS, 2005, 46 (38) :6545-6547
[5]   A novel one-pot method for the preparation of pyrazoles by 1,3-dipolar cycloadditions of diazo compounds generated in situ [J].
Aggarwal, VK ;
de Vicente, J ;
Bonnert, RV .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (13) :5381-5383
[6]   Antitumor evaluation and molecular docking study of substituted 2-benzylidenebutane-1,3-dione, 2-hydrazonobutane-1,3-dione and trifluoromethyl-1H-pyrazole analogues [J].
Al-Suwaidan, Ibrahim A. ;
Abdel-Aziz, Naglaa I. ;
El-Azab, Adel S. ;
El-Sayed, Magda A-A ;
Alanazi, Amer M. ;
El-Ashmawy, Mahmoud B. ;
Abdel-Aziz, Alaa A-M .
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2015, 30 (04) :679-687
[7]   Synthesis and anticonvulsant activity of novel quinazolin-4(3H)-one derived pyrazole analogs [J].
Alagarsamy, Veerachamy ;
Saravanan, Govindaraj .
MEDICINAL CHEMISTRY RESEARCH, 2013, 22 (04) :1711-1722
[8]  
Antonio J., 2016, CATAL SCI TECHNOL, V6, P4705, DOI [10.1039/C6CY00249H, DOI 10.1039/C6CY00249H]
[9]  
Baraldi PG, 1997, ANTI-CANCER DRUG DES, V12, P555
[10]   Synthesis of 3,5-diphenyl-1H-pyrazoles [J].
Bhat, BA ;
Puri, SC ;
Qurishi, MA ;
Dhar, KL ;
Qazi, GN .
SYNTHETIC COMMUNICATIONS, 2005, 35 (08) :1135-1142