19062-70-5Relevant academic research and scientific papers
Novel hybrid molecules of quinazoline chalcone derivatives: Synthesis and study of In Vitro cytotoxic activities
Thiriveedhi, Arunkumar,Nadh, Ratnakaram Venkata,Srinivasu, Navuluri,Kaushal, Kishore
, p. 757 - 765 (2018/06/26)
Background: A new series of quinazoline linked chalcone conjugates were synthesized and evaluated for their in vitro cytotoxicity. Methods: The quinazoline-chalcone derivatives (13a-r) have been prepared by the Claisen-Schmidt condensation of various substituted benzaldehydes (12a-r) with substituted l-(4-(3,4- dihydroquinazolin-4-ylamino)phenyl)ethanone (11a-b) in the presence of aqueous NaOH. Three potential compounds 13f, 13g and 13h exhibited cytotoxicity against leukemia (GI50 value of 1.07, 0.26 and 0.24 μM), Non-small lung (GI50 values of 2.05,1.32 and 0.23 μM), colon (GI50 values of 0.54, 0.34 and 0.34 μM) and breast (GI50 values of 2.17, 1.84 and 0.22 μM) cell line, respectively. Results and Conclusion: Based on these biological results, it is evident that compound 13h has the potential to be considered for further detailed studies either alone or in combination with existing therapies as potential anticancer agents.
Synthesis and biological evaluation of new tetramethylpyrazine-based chalcone derivatives as potential anti-Alzheimer agents
Wang, Meng,Qin, Hua-Li,Leng, Jing,Ameeduzzafar,Amjad, Muhammad Wahab,Raja, Maria Abdul Ghafoor,Hussain, Muhammad Ajaz,Bukhari, Syed Nasir Abbas
, p. 1859 - 1866 (2018/07/31)
In the current study, a series of new ligustrazine-based chalcones was synthesized. For insertion of tetramethylpyrazine (TMP, also designated as ligustrazine) in chemical backbone of chalcone, a new ligustrazine-based aldehyde was prepared. New ketones were synthesized for inclusion of quinazolin-4-yl amino and pyrazin-2-yl amino moieties. The newly synthesized compounds were screened for acetylcholinesterase, butyrylcholinesterase, and monoamine oxidases (MAO) inhibitory activities and also for in vitro cytotoxicity on PC12 cells. The effect of these compounds against amyloid β-induced cytotoxicity and aggregation was also investigated. The synthesized compounds effectively inhibited the related enzymes and also exhibited neuroprotective effects. Most of the compounds displayed better inhibitory potencies against Aβ aggregation than reference compounds. Some compounds such as 11e and 16b showed very potent effects on multiple targets exhibiting behavior as multifunctional anti-Alzheimer agents.
Design, Synthesis, Antiviral Activities of Novel Phosphonate Derivatives Containing Quinazoline Based on Chalone Motif
Zhang, Guo-Ping,Pan, Jian-Ke,Zhang, Jian,Wu, Zeng-Xue,Liu, Deng-Yue,Zhao, Lei
, p. 2548 - 2555 (2017/07/25)
Based on the structure of natural product chalone, a series of novel phosphonate derivatives were designed and synthesized through 1,4-hydrophosphinylation of α,β-unsaturated carbonyl compounds. Their structures were characterized by IR, NMR, MS, and elemental analysis. The antiviral activities against cucumber mosaic virus were evaluated for the first time. The bioassay results indicated that most compounds exhibited good protective activities, low curative activities, and weak inactive activities. The antiviral protective activities of compounds C2 and C5 were 55.1% and 56.8%, respectively, which are slightly higher than those of the commercial Ningnanmyin (49.3%) and Dufulin (53.1%). Moreover, compounds C2 and C9 exhibited moderate curative activities (42.6% and 46.6%). Therefore, the basic motif of C1 can be used as a new lead structure for developing antivirus agents.
Chalcone phosphonate derivative containingquinazoline and preparation method and application of chalcone phosphonate derivative
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Paragraph 0023; 0028, (2016/10/09)
The invention discloses a chalcone phosphonate derivative containingquinazoline and a preparation method and application of the chalcone phosphonate derivative. The structural formula (1) of the chalcone phosphonate derivative is as shownin thespecification, and in the formula, R1 is phenyl, 3-bromophenyl, 2-chlorophenyl, 4-bromophenyl, 2-fluorophenyl, 2-thienyl, 2,6-dichlorophenyl, 4-chlorophenyl, 2-furyl, 2-trifluoromethylphenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-chloro-6-fluorophenyl. The chalcone phosphonate derivative is simple in synthesis route, high in yield and capable of efficiently and safely preventing and treating plant virus diseases.
The combination of quinazoline and chalcone moieties leads to novel potent heterodimeric modulators of breast cancer resistance protein (BCRP/ABCG2)
Kraege, Stefanie,Stefan, Katja,Juvale, Kapil,Ross, Thomas,Willmes, Thomas,Wiese, Michael
, p. 212 - 229 (2016/04/26)
During the last decade it has been found that chalcones and quinazolines are promising inhibitors of ABCG2. The combination of these two scaffolds offers a new class of heterocyclic compounds with potentially high inhibitory activity against ABCG2. For this purpose we investigated 22 different heterodimeric derivatives. In this series only methoxy groups were used as substituents as these had been proven superior for inhibitory activity of chalcones. All compounds were tested for their inhibitory activity, specificity and cytotoxicity. The most potent ABCG2 inhibitor in this series showed an IC50 value of 0.19 μM. It possesses low cytotoxicity (GI50 = 93 μM), the ability to reverse MDR and is nearly selective toward ABCG2. Most compounds containing dimethoxy groups showed slight activity against ABCB1 too. Among these three compounds (17, 19 and 24) showed even higher activity toward ABCB1 than ABCG2. All inhibitors were further screened for their effect on basal ATPase activity. Although the basal ATPase activity was partially stimulated, the compounds were not transported by ABCG2. Thus, quinazoline-chalcones are a new class of effective ABCG2 inhibitors.
Discovery of new HER2/EGFR dual kinase inhibitors based on the anilinoquinazoline scaffold as potential anti-cancer agents
Sadek, Maiada M.,Serrya, Rabah A.,Kafafy, Abdel-Hamid N.,Ahmed, Marawan,Wang, Feng,Abouzid, Khaled A. M.
, p. 215 - 222 (2014/04/03)
Herein, we designed and synthesized certain anilinoquinazoline derivatives bearing bulky arylpyridinyl, arylpropenoyl and arylpyrazolyl moieties at the 4′ position of the anilinoquinazoline, as potential dual HER2/EGFR kinase inhibitors. A detailed molecular modeling study was performed by docking the synthesized compounds in the active site of the epidermal growth factor receptor (EGFR). The synthesized compounds were further tested for their inhibitory activity on EGFR and HER2 tyrosine kinases. The aryl 2-imino-1,2-dihydropyridine derivatives 5d and 5e displayed the most potent inhibitory activity on EGFR with IC50 equal to 2.09 and 1.94 μM, respectively, and with IC50 equal to 3.98 and 1.04 μM on HER2, respectively. Furthermore, the anti-proliferative activity of these most active compounds on MDA-MB-231 breast cancer cell lines, known to overexpress EGFR, showed an IC50 range of 2.4 and 2.5 μM, respectively.
