Synthesis of Thiazole Linked Imidazo[2,1-b]Thiazoles as Anticancer Agents

被引:28
作者
Mahmoud, Huda K. [1 ]
Gomha, Sobhi M. [1 ,2 ]
Farghaly, Thoraya A. [1 ,3 ]
Awad, Hanem M. [4 ]
机构
[1] Cairo Univ, Dept Chem, Fac Sci, Giza 12613, Egypt
[2] Islamic Univ Almadinah Almonawara, Dept Chem, Fac Sci, Almadinah Almonawara, Saudi Arabia
[3] Umm Al Qura Univ, Fac Appl Sci, Dept Chem, Makkah El Mukarramah, Saudi Arabia
[4] Natl Res Ctr, Dept Tanning Mat & Leather Technol, Cairo, Egypt
关键词
Antitumor agents; Imidazo[21-b]thiazole; Thiazole; Thiosemicarbazones; Thiocarbohydrazide; BIOLOGICAL EVALUATION; POTENTIAL ANTICANCER; MOLECULAR DOCKING; DERIVATIVES SYNTHESIS; ANTITUMOR AGENTS; DESIGN; IMIDAZOLE; IMIDAZOTHIAZOLE; CHALCONE; MOIETY;
D O I
10.1080/10406638.2019.1689514
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Based on the search for new heterocyclic drugs suitable as anticancer agents and our knowledge of the efficacy of thiazol and imidazothiazole derivatives as anticancer drugs, we have created four new series of thiazolylimidazothiazole derivatives from the reaction of each of imidazothiazole-thiosemicabazone and imidazothiazole-thicarbohydrazone derivatives with acetyl-hydrazonoyl chlorides and ester-hydrazonoyl chlorides in dioxane/drops of Et3N. The structure of the four novel series of thiazolylimidazothiazoles was characterized by physical and spectroscopic tools. In addition, all the newly synthesized derivatives were examined in vitro for their activity against HCT-116 and MCF-7 human cancer cells using the MTT assay to evaluate their pharmaceutical importance. The encouraging potent results observed from anticancer elusidation studies on the newly prepared thiazolylimidazothiazole derivatives make the design and synthesis of novel series of these systems and studying of their pharmaceutical importance an active zone for more and more investigations.
引用
收藏
页码:1608 / 1622
页数:15
相关论文
共 43 条
[31]   Synthesis, antimicrobial activity and advances in structure-activity relationships (SARs) of novel tri-substituted thiazole derivatives [J].
Reddy, Guda Mallikarjuna ;
Garcia, Jarem Raul ;
Reddy, Vemulapati Hanuman ;
de Andrade, Ageo Meier ;
Camilo, Alexandre, Jr. ;
Pontes Ribeiro, Renan Augusto ;
de lazaro, Sergio Ricardo .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2016, 123 :508-513
[32]   Design, synthesis and biological evaluation of imidazo[2,1-b]thiazole and benzo[d]imidazo[2,1-b]thiazole derivatives as Mycobacterium tuberculosis pantothenate synthetase inhibitors [J].
Samala, Ganesh ;
Devi, Parthiban Brindha ;
Saxena, Shalini ;
Meda, Nikhila ;
Yogeeswari, Perumal ;
Sriram, Dharmarajan .
BIOORGANIC & MEDICINAL CHEMISTRY, 2016, 24 (06) :1298-1307
[33]   Anoikis resistance and tumor metastasis [J].
Simpson, Craig D. ;
Anyiwe, Kika ;
Schimmer, Aaron D. .
CANCER LETTERS, 2008, 272 (02) :177-185
[34]   Design, synthesis and identification of novel substituted 2-amino thiazole analogues as potential anti-inflammatory agents targeting 5-lipoxygenase [J].
Sinha, Shweta ;
Doble, Mukesh ;
Manju, S. L. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2018, 158 :34-50
[35]   Synthesis, structure, and antioxidant activity of methoxy- and hydroxyl-substituted 2'-aminochalcones [J].
Sulpizio, Chiara ;
Roller, Alexander ;
Giester, Gerald ;
Rompel, Annette .
MONATSHEFTE FUR CHEMIE, 2016, 147 (10) :1747-1757
[36]   Synthesis of benzo[d]imidazo[2,1-b]thiazole-chalcone conjugates as microtubule targeting and apoptosis inducing agents [J].
Sultana, Faria ;
Bonam, Srinivasa Reddy ;
Reddy, V. Ganga ;
Nayak, V. Lakshma ;
Akunuri, Ravikumar ;
Routhu, Sunitha Rani ;
Alarifi, Abdullah ;
Halmuthur, M. Sampath Kumar ;
Kamal, Ahmed .
BIOORGANIC CHEMISTRY, 2018, 76 :1-12
[37]   Global Cancer Statistics, 2012 [J].
Torre, Lindsey A. ;
Bray, Freddie ;
Siegel, Rebecca L. ;
Ferlay, Jacques ;
Lortet-Tieulent, Joannie ;
Jemal, Ahmedin .
CA-A CANCER JOURNAL FOR CLINICIANS, 2015, 65 (02) :87-108
[38]   Anti-HIV-1 activity of an antisense phosphorothioate oligonucleotide bearing imidazole and primary amine groups [J].
Ushijima, K ;
Shirakawa, M ;
Kagoshima, K ;
Park, WS ;
Miyano-Kurosaki, N ;
Takaku, H .
BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (08) :2165-2169
[39]   Microwave-assisted green synthesis of new imidazo[2,1-b]thiazole derivatives and their antimicrobial, antimalarial, and antitubercular activities [J].
Vekariya, Rajesh H. ;
Patel, Kinjal D. ;
Vekariya, Mayur K. ;
Prajapati, Neelam P. ;
Rajani, Dhanji P. ;
Rajani, Smita D. ;
Patel, Hitesh D. .
RESEARCH ON CHEMICAL INTERMEDIATES, 2017, 43 (11) :6207-6231
[40]  
Venkatesh T., 2016, Med. Chem., V6, P440, DOI 10.4172/2161-0444.1000383