Synthesis of Some New Pyrazoline-Based Thiazole Derivatives and Evaluation of Their Antimicrobial, Antifungal, and Anticancer Activities

被引:27
作者
Elewa, Safaa I. [1 ]
Mansour, Eman [1 ]
Nassar, Ibrahim F. [2 ]
Mekawey, Amal A. I. [3 ]
机构
[1] Ain Shams Univ, Fac Women Arts Sci & Educ, Dept Chem, Cairo 11566, Egypt
[2] Ain Shams Univ, Fac Specif Educ, Cairo 11566, Egypt
[3] Al Azhar Univ, Reg Ctr Mycol & Biotechnol, Cairo 11651, Egypt
关键词
thiophene; thiazole; pyrazoline; antimicrobial; antifungal; anticancer activity; BEARING BENZENE SULFONAMIDE; VITRO ANTITUMOR-ACTIVITY; BIOLOGICAL EVALUATION; CONVENIENT SYNTHESIS; DESIGN; MOIETY; 2-PYRAZOLINES; INHIBITORS; ANALOGS; SERIES;
D O I
10.1134/S1068162020030061
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
3-(2-Thienyl)-5-aryl-1-thiocarbamoyl-2-pyrazolines were reacted with chloroacetone derivatives and hydrazonyl chloride derivatives in ethanol to afford the corresponding thiazolylpyrazoline derivatives and thiophenylpyrazolyl-5-substituted aryl-diazenylthiazole derivatives, respectively. The structures of the newly synthesized compounds were elucidated by different elemental and spectral analyses (IR, mass,H-1 and(13)C NMR). The antimicrobial and antifungal activities of the newly synthesized compounds were evaluated against four bacterial species and five fungal strains. In addition, the antitumor activities of two of the newly synthesized compounds 1-(2-(5-(4-chlorophenyl)-3-(thiophen-2-yl)-4,5-dihydropyrazol-1-yl)-4-methyl thiazol-5-yl)ethan-1-one and 2-(5-(4-chlorophenyl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)-4-methyl-5-(phenyl-diazenyl)thiazole against HEPG-2, HCT-116, MCF-7, BHK, and CACO-2 were evaluated. From the obtained results, we found that these two compounds were the most potent candidates towards all gram-positive and gram-negative bacteria, as well as the fungi studied. Also, the same two compounds showed strong antitumor activities against two of the tumor cell lines (HCT-116 and CACO-2).
引用
收藏
页码:382 / 392
页数:11
相关论文
共 45 条
[1]  
Abdel-Kader HA, 1995, ASSIUT VET MED J, V34, P67
[2]   Synthesis and Anticancer Activity of Some Novel Tetralin-6-yl-pyrazoline, 2-Thioxopyrimidine, 2-Oxopyridine, 2-Thioxo-pyridine and 2-Iminopyridine Derivatives [J].
Al-Abdullah, Ebtehal S. .
MOLECULES, 2011, 16 (04) :3410-3419
[3]   4,5-Dihydro-1H-pyrazole: an indispensable scaffold [J].
Alex, Jimi Marin ;
Kumar, Raj .
JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2014, 29 (03) :427-442
[4]   Synthesis and anticancer activity of some 8-substituted-7-methoxy-2H-chromen-2-one derivatives toward hepatocellular carcinoma HepG2 cells [J].
Amin, Kamilia M. ;
Abou-Seri, Sahar M. ;
Awadallah, Fadi M. ;
Eissa, Amal A. M. ;
Hassan, Ghaneya S. ;
Abdulla, Mohamed M. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 90 :221-231
[5]   Synthesis and biological evaluation of novel coumarin-pyrazoline hybrids endowed with phenylsulfonyl moiety as antitumor agents [J].
Amin, Kamilia M. ;
Eissa, Amal A. M. ;
Abou-Seri, Sahar M. ;
Awadallah, Fadi M. ;
Hassan, Ghaneya S. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 60 :187-198
[6]   Review: biologically active pyrazole derivatives [J].
Ansari, Anam ;
Ali, Abad ;
Asif, Mohd ;
Shamsuzzaman .
NEW JOURNAL OF CHEMISTRY, 2017, 41 (01) :16-41
[7]   Recent applications of 1,3-thiazole core structure in the identification of new lead compounds and drug discovery [J].
Ayati, Adile ;
Emami, Saeed ;
Asadipour, Ali ;
Shafiee, Abbas ;
Foroumadi, Alireza .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 97 :699-718
[8]   Synthesis and characterization of new 3,5-dinaphthyl substituted 2-pyrazolines and study of their antimicrobial activity [J].
Azarifar, D ;
Shaebanzadeh, M .
MOLECULES, 2002, 7 (12) :885-895
[9]   Synthesis and biological evaluation of some new 2-pyrazolines bearing benzene sulfonamide moiety as potential anti-inflammatory and anti-cancer agents [J].
Bano, Sameena ;
Javed, Kalim ;
Ahmad, Shamim ;
Rathish, I. G. ;
Singh, Surender ;
Alam, M. S. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (12) :5763-5768
[10]   Synthesis of some new 1,3,5-trisubstituted pyrazolines bearing benzene sulfonamide as anticancer and anti-inflammatory agents [J].
Bashir, Rafia ;
Ovais, Syed ;
Yaseen, Shafiya ;
Hamid, Hinna ;
Alam, M. S. ;
Samim, Mohammad ;
Singh, Surender ;
Javed, Kalim .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (14) :4301-4305