86-84-0Relevant academic research and scientific papers
Role of positional isomers on receptor-anion binding and evidence for resonance energy transfer
Jose, D. Amilan,Kumar, D. Krishna,Kar, Prasenjit,Verma, Sandeep,Ghosh, Amrita,Ganguly, Bishwajit,Ghosh, Hirendra N.,Das, Amitava
, p. 12007 - 12014 (2007)
New urea-based sensors show a strong affinity for F-, CH3COO-, and H2PO4- with an appreciable color change in the presence of excess F-. The position of the nitro group in the urea derivative influences the relative affinity toward anionic analytes. Spectral and ab initio studies showed the difference in the deprotonation sites for the ortho- and meta/para-isomers in these cases. Photophysical studies confirmed the resonance energy transfer in the case of the ortho-isomer. The ortho-isomer can act as a dual emission probe for F-.
Naked eye detection of anions by 2,2¤-bianthracene derivative bearing urea groups in various organic solvents
Kondo, Shin-ichi,Osawa, Kohei,Tagaya, Hideyuki
supporting information, p. 290 - 294 (2020/04/10)
A highly fluorescent 2,2¤-bianthryl derivative bearing urea groups (2) was prepared as an anion receptor. The UV-vis and fluorescence titrations of 2 in various organic solvents revealed that the association constants (K11) were correlated with acceptor number and Swain acity of the solvents used, and tetrahydrofuran was found to strongly enhance the K11 for Cl1 and AcO1 due to enthalpy driven complexation, in which naked eye detection of AcO1 was achieved.
Synthesis and in vitro anti-bladder cancer activity evaluation of quinazolinyl-arylurea derivatives
Chen, Jia-Nian,Li, Ting,Cheng, Li,Qin, Tai-Sheng,Sun, Ye-Xiang,Chen, Chu-Ting,He, Yue-Zhen,Liu, Guang,Yao, Di,Wei, Ying,Li, Qiu-Yin,Zhang, Guang-Ji
, (2020/09/09)
Based on the structural modification of molecular-targeted agent sorafenib, a series of quinazolinyl-arylurea derivatives were synthesized and evaluated for their anti-proliferative activities against six human cancer cell lines. Compared with other cell lines tested, T24 was more sensitive to most compounds. Compound 7j exhibited the best profile with lower IC50 value and favorable selectivity. In this study, we focused on 7j-induced death forms of T24 cells and tried to elucidate the reason for its potent proliferative inhibitory activity. Compound 7j treatment could trigger three different cell death forms including apoptosis, ferroptosis, and autophagy; which form would occur depended on the concentrations and incubation time of 7j: (1) Lower concentrations within the initial 8 h of 7j treatment led to apoptosis-dependent death. (2) Ferroptosis and autophagy occurred in the case of higher concentrations combining with extended incubation time through effectively regulating the Sxc?/GPx4/ROS and PI3K/Akt/mTOR/ULK1 pathways, respectively. (3) The above death forms were closely associated with intracellular ROS generation and decreased mitochondrial membrane potential induced by 7j. In molecular docking and structure-activity relationship analyses, 7j could bind well to the active site of the corresponding receptor glutathione peroxidase 4 (GPx4). Compound 7j could be a promising lead for molecular-targeted anti-bladder cancer agents’ discovery.
Design, synthesis, biological evaluation and molecular docking study of arylcarboxamido piperidine and piperazine-based hydroxamates as potential HDAC8 inhibitors with promising anticancer activity
Trivedi, Prakruti,Adhikari, Nilanjan,Amin, Sk. Abdul,Bobde, Yamini,Ganesh, Routholla,Jha, Tarun,Ghosh, Balaram
, (2019/08/20)
HDAC8 has been established as one of the vital targets as far as the cancer is concerned. Different compounds having potential HDAC inhibitory activity have been approved by USFDA. However, none of these compounds are selective towards specific HDAC isoform. In this current study, some new hydroxamate derivatives with alkylpiperidine and alkylpiperazine linker moieties have been designed, synthesized and biologically evaluated. All these compounds are effective HDAC8 inhibitors comprising more or less similar cytotoxic potential against different cancer cell lines. It is observed that the piperazine scaffold containing compound is more active than the compound with piperidine scaffold for exerting HDAC8 inhibitory activity. Moreover, the 4-quinolyl cap group is better than the biphenyl group which is better than the benzyl group for producing higher HDAC8 inhibition as well as cytotoxicity. These compounds displayed selective HDAC8 inhibition over HDAC3. Moreover, these compounds showed an increased caspase3/7 activity suggesting their anticancer potential through modulation of apoptotic pathways. Molecular docking study with three potent compounds was performed with both HDAC3 and HDAC8 enzymes to understand the selectivity profile of these compounds. Compound containing 4-quinolyl cap group with alkyl piperazinyl urea linker moiety has been emerged out as the lead molecule that may be further modified to design more effective and selective HDAC8 inhibitors in future.
With anti-tumor effect of a quinazoline-urea derivative and its application (by machine translation)
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Paragraph 0139-0142; 0175, (2016/11/02)
The present invention relates to a of the general formula (II) anti-tumor function of said quinazoline-urea derivative and its application. The definition of the substituent in the general formula (II) in the specification. This invention, in order to SUO draw non-Buddhist nun and Geftinat compounds as the precursor, retention of SUO draw non-Buddhist nun the pharmocology-carbamido; at the same time, such as in reserved [...] EGFR-TKIs Geftinat, synthesis, and obtain a series of quinazoline-urea derivatives, by the in vitro activity tests, some compounds exhibit excellent anti-tumor activity, such derivatives have high research and utility value. (II). (by machine translation)
Antimalarial activity of novel imidazoisoquinolinone derivatives correlates with heme binding affinity
Bollini, Mariela,Casal, Juan J.,Asís, Silvia E.,Leal, Emilse S.,Bruno, Ana M.
, p. 1496 - 1503 (2015/04/27)
A series of novel imidazoisoquinolinone derivatives were synthesized and evaluated for in vitro antimalarial efficacy against chloroquine sensitive GHA strain of Plasmodium falciparum. Compounds 2, 4, 6, 9, and 17 revealed moderate to good activities in the micromolar range. Binding interaction between these active compounds and heme were determined and correlated with antimalarial activity. A good correlation (r = 0.98) was observed between antimalarial activity and the heme dissociation constants (K d). These suggest that antimalarial mode of action of this class of compounds appears to be similar to that of chloroquine and involves the inhibition of hemozoin formation.
Development of synthetic aminopeptidase N/CD13 inhibitors to overcome cancer metastasis and angiogenesis
Su, Li,Cao, Jiangying,Jia, Yuping,Zhang, Xiaonan,Fang, Hao,Xu, Wenfang
supporting information, p. 959 - 964 (2013/02/23)
Cancer metastasis is a major barrier to its treatment and an important cause of patient death. Antimetastatic agents hold promise for patients with advanced metastatic tumors. Aminopeptidase N/CD13 (APN) is being pursued by many as an important target against cancer metastasis and angiogenesis, but there are few reports on the in vivo evaluation of synthetic APN inhibitors. Herein, a series of compounds targeting APN were synthesized and evaluated for their antimetastasis and antiangiogenesis potency both in vitro and in vivo. Excitingly, compounds 4m, 4t, and 4cc, with the most potent APN inhibitory activities, displayed significant antimetastasis and antiangiogenesis effects in vitro and in vivo, suggesting that those synthetic APN inhibitors have the potential to overcome cancer metastasis and angiogenesis.
Investigating N-methoxy-N′-aryl ureas in oxidative C-H olefination reactions: An unexpected oxidation behaviour
Willwacher, Jens,Rakshit, Souvik,Glorius, Frank
supporting information; experimental part, p. 4736 - 4740 (2011/08/06)
Herein, we report a urea derived directing group for mild and highly selective oxidative C-H bond olefination. Subsequent intramolecular Michael addition affords dihydroquinazolinones in good yields. The N-O bond of the urea substrate exhibits superior oxidative behaviour compared to a variety of other external oxidants. The Royal Society of Chemistry 2011.
Discovering potent small molecule inhibitors of cyclophilin A using de novo drug design approach
Ni, Shuaishuai,Yuan, Yaxia,Huang, Jin,Mao, Xiaona,Lv, Maosheng,Zhu, Jin,Shen, Xu,Pei, Jianfeng,Lai, Luhua,Jiang, Hualiang,Li, Jian
supporting information; experimental part, p. 5295 - 5298 (2010/02/28)
This work describes an integrated approach of de novo drug design, chemical synthesis, and bioassay for quick identification of a series of novel small molecule cyclophilin A (CypA) inhibitors (1-3). The activities of the two most potent CypA inhibitors (3h and 3i) are 2.59 and 1.52 nM, respectively, which are about 16 and 27 times more potent than that of cyclosporin A. This study clearly demonstrates the power of our de novo drug design strategy and the related program LigBuilder 2.0 in drug discovery.
Synthesis and DNA-cleaving activity of lactenediynes conjugated with DNA-complexing moieties
Banfi, Luca,Basso, Andrea,Bevilacqua, Elisabetta,Gandolfo, Valentina,Giannini, Giuseppe,Guanti, Giuseppe,Musso, Loana,Paravidino, Monica,Riva, Renata
, p. 3501 - 3518 (2008/09/21)
Lactenediynes are compounds characterized by the fusion of a β-lactam with a cyclodeca-3-ene-1,5-diyne. In this work the most promising members of this family have been activated by attaching a carbalkoxy or a carbamoyl group to the azetidinone nitrogen, and conjugated to various DNA-complexing moieties, either acting by intercalation or through groove binding. These conjugated artificial enediynes have been demonstrated to possess in vitro ability to produce single and double strand cleavage of plasmid DNA. As potency and capacity to induce double cut, they rank among the best simple enediyne analogues ever prepared. A thorough investigation was carried out in order to develop the best suited linkers for assembling these conjugates.
