- Design, synthesis and bioactivity evaluation of novel evodiamine derivatives with excellent potency against gastric cancer
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Gastric cancer represents a significant health burden worldwide. Previously, inspired by the traditional Chinese medicine Wu-Chu-Yu to treat the spleen and stomach system for thousands of years, we identified N14-phenyl substituted evodiamine derivatives as potential antitumor agents with favorable inhibition on Top1. Herein, structural optimization and structure-activity relationship studies (SARs) led us to discovering a highly active evodiamine derivative compound 6t against gastric cancer. Further anti-tumor mechanism studies revealed that compound 6t played as the inhibition of topoisomerase 1 (Top1), effectively induced apoptosis, obviously arrested the cell cycle at the G2/M phase, and significantly inhibited the migration and invasion of SGC-7901 and MGC-803 cell lines in a dose-dependent manner. Moreover, the compound 6t was low toxicity in vivo and exhibited excellent anti-tumor activity (TGI = 70.12%) in the MGC-803 xenograft models. In summary, compound 6t represents a promising candidate as a potential chemotherapeutic agent against gastric cancer.
- Liang, Ziyi,Lei, Fang,Deng, Jiedan,Zhang, Honghua,Wang, Yuqing,Li, Junfang,Shi, Tao,Yang, Xiaoyan,Wang, Zhen
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- Design, synthesis and bioactivity evaluation of novel N-phenyl-substituted evodiamine derivatives as potent anti-tumor agents
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Natural products are important sources for the development of therapeutic medicine, among which evodia fruit has a wide range of medicinal properties in traditional Chinese medicine. Evodiamine, the main active component of evodia fruit, has various anti-cancer effects and has been proved to be a Topo inhibitor. From our previous attempts of modifying evodiamine, we found that the N14 phenyl substituted derivatives had showed great anti-tumor activity, which prompted us to further explore the novel structures and activities of these compounds. Compound 6f, as a N14 3-fluorinated phenyl substituted evodiamine derivative, showed a certain inhibitory activity against Topo I at 200 μM. By studying its anti-tumor effects in vitro, compound 6f could inhibit proliferation and induce apoptosis, as well as arrest the cell cycle of HGC-27 and HT-29 cell lines at G2/M phase in a concentration-dependent manner. Moreover, compound 6f could inhibit the migration and invasion of HGC-27 cell lines. Meanwhile, compound 6f could induce apoptosis of HGC-27 cells by inhibiting PI3K/AKT pathway. Overall, this work demonstrated that the N14 phenyl-substituted evodiamine derivatives had a good inhibitory effect on tumor cells in vitro, providing a promising strategy for developing potential anticancer agents for the treatment of gastrointestinal tumors.
- Deng, Jiedan,Hao, Xiangyong,Lei, Fang,Liang, Ziyi,Wang, Yuqing,Wang, Zhen,Yang, Xiaoyan,Zhang, Honghua
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- Design, synthesis and evaluation of novel 9-arylalkyl-10-methylacridinium derivatives as highly potent FtsZ-targeting antibacterial agents
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With the increasing incidence of antibiotic resistance, new antibacterial agents having novel mechanisms of action hence are in an urgent need to combat infectious diseases caused by multidrug-resistant (MDR) pathogens. Four novel series of substituted 9-arylalkyl-10-methylacridinium derivatives as FtsZ inhibitors were designed, synthesized and evaluated for their antibacterial activities against various Gram-positive and Gram-negative bacteria. The results demonstrated that they exhibited broad-spectrum activities with substantial efficacy against MRSA and VRE, which were superior or comparable to the berberine, sanguinarine, linezolid, ciprofloxacin and vancomycin. In particular, the most promising compound 15f showed rapid bactericidal properties, which avoid the emergence of drug resistance. However, 15f showed no inhibitory effect on Gram-negative bacteria but biofilm formation study gave possible answers. Further target identification and mechanistic studies revealed that 15f functioned as an effective FtsZ inhibitor to alter the dynamics of FtsZ self-polymerization, which resulted in termination of the cell division and caused cell death. Further cytotoxicity and animal studies demonstrated that 15f not only displayed efficacy in a murine model of bacteremia in vivo, but also no significant hemolysis to mammalian cells. Overall, this compound with novel skeleton could serve as an antibacterial lead of FtsZ inhibitor for further evaluation of drug-likeness.
- Song, Di,Zhang, Nan,Zhang, Panpan,Zhang, Na,Chen, Weijin,Zhang, Long,Guo, Ting,Gu, Xiaotong,Ma, Shutao
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- Compound, pharmaceutical composition, medicine and application of compound, pharmaceutical composition and medicine in preparation of antibacterial products
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The invention particularly relates to a compound, a pharmaceutical composition, a medicine and application of the compound, the pharmaceutical composition and the medicine in preparation of antibacterial products. The seeking of a novel antibacterial target and the development of a novel chemical entity have important significance for solving the increasingly severe bacterial drug resistance problem at present, and the design of a compound entity acting on the FtsZ target is expected to be developed to obtain an antibacterial drug which has no influence on a host. The invention provides a 9-aralkyl-10-methylacridine quaternary ammonium salt derivative and a preparation method thereof, and the compound has significant bactericidal and/or bacteriostatic activity on gram-positive bacteria, has a good effect of inhibiting bacterial division protein FtsZ, and can be used for preparing antibacterial products.
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Paragraph 0066-0068
(2021/07/17)
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- Aromatic heterocycle substituted acridine quaternary ammonium salt derivative as well as preparation method and application thereof
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The invention belongs to the technical field of pharmaceutical compounds, relates to an aromatic heterocyclic substituted acridine quaternary ammonium salt derivative and a preparation method and application thereof, and has the structure shown in a formula (I). In-flight R1 A compound selected from the group consisting of aryl and heteroaryl. Substituted aryls. X Is a halogen or benzenesulfonate anion. The invention provides an aromatic heterocyclic substituted acridine quaternary ammonium salt derivative as well as a preparation method and application thereof, and is designed to synthesize an aromatic heterocyclic substituted acridine quaternary ammonium salt derivative through a simplified structure, and is designed to synthesize an aromatic heterocyclic substituted acridine quaternary ammonium salt derivative so as to achieve the unique antibacterial effect by inhibiting the bacteria FtsZ and bacterial biofilm.
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Paragraph 0067-0070
(2021/09/29)
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- Synthesis, antibacterial evaluation and computational studies of new acridone-1,2,3-triazole hybrids
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In continuation of our efforts to develop new drugs with antibacterial properties we have synthesized and evaluated new 1,2,3-triazole derivatives from acridone. The synthetic approach was started by the preparation of acridone skeleton through the Ullman condensation of 2-bromobenzoic acid and aniline derivatives. Subsequently, acridone nucleus was functionalized with propargyl bromide. Then, a click reaction of the latter compound and aromatic azides led to the formation of the title compounds in good yields. The synthesized compounds were screened for their in vitro antibacterial activity against one gram-positive bacteria S. aureus and three gram-negative bacteria P. putida, K. pneumoniae and E. coli. Among the synthesized compounds, 2-methyl-10-((1-(o-tolyl)-1H-1,2,3-triazol-4-yl)methyl)acridone (4e) had the most potent inhibitory activity against S. aureus with MIC = 10.1 μg/mL. Then, in silico docking studies were used in order to understand the binding interactions and mode of action of these compounds.
- Aarjane, Mohammed,Amine, Amina,Slassi, Siham
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- Development of LM98, a Small-Molecule TEAD Inhibitor Derived from Flufenamic Acid
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The YAP-TEAD transcriptional complex is responsible for the expression of genes that regulate cancer cell growth and proliferation. Dysregulation of the Hippo pathway due to overexpression of TEAD has been reported in a wide range of cancers. Inhibition of TEAD represses the expression of associated genes, demonstrating the value of this transcription factor for the development of novel anti-cancer therapies. We report herein the design, synthesis and biological evaluation of LM98, a flufenamic acid analogue. LM98 shows strong affinity to TEAD, inhibits its autopalmitoylation and reduces the YAP-TEAD transcriptional activity. Binding of LM98 to TEAD was supported by 19F-NMR studies while co-crystallization experiments confirmed that LM98 is anchored within the palmitic acid pocket of TEAD. LM98 reduces the expression of CTGF and Cyr61, inhibits MDA-MB-231 breast cancer cell migration and arrests cell cycling in the S phase during cell division.
- Mélin, Léa,Abdullayev, Shuay,Fnaiche, Ahmed,Vu, Victoria,González Suárez, Narjara,Zeng, Hong,Szewczyk, Magdalena M.,Li, Fengling,Senisterra, Guillermo,Allali-Hassani, Abdellah,Chau, Irene,Dong, Aiping,Woo, Simon,Annabi, Borhane,Halabelian, Levon,LaPlante, Steven R.,Vedadi, Masoud,Barsyte-Lovejoy, Dalia,Santhakumar, Vijayaratnam,Gagnon, Alexandre
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p. 2982 - 3002
(2021/08/03)
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- Novel series of N-acylhydrazone based on acridone: Synthesis, conformational and theoretical studies
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In this work, novel N-acylhydrazone derivatives from acridone have been synthesized by condensation of 9-oxoacridin-10(9H)-yl)acetohydrazide with various aldehyde and ketone. The structures of these novel compounds were elucidated by 1H NMR, 13C NMR, IR and mass spectroscopy. The NMR data shows two conformations (E, trans and E, cis) due to N–C(O) bond rotation, the conformations of synthesized compounds have been investigated by different NMR methods. The rotational barriers around N–C(O) bond for compound 5a was measured in DMSO using dynamic NMR spectroscopy, this result was confirmed by DFT calculations at B3LYP/6–31 G (d) level in DMSO.
- Aarjane, Mohammed,Amine, Amina,Slassi, Siham
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- Synthesis and biological evaluation of novel isoxazole derivatives from acridone
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The present study was carried out in an?attempt to synthesize a new class of potential antibacterial agents. In this context, novel isoxazoles were synthesized and evaluated for their potential antibacterial behavior against four pathogenic bacterial strains. The synthesized compounds exhibited moderate-to-good antibacterial activity against these strains. The highest antibacterial activity was observed against the Escherichia coli strains, particularly for compounds 4a and 4e with phenyl and para-nitrophenyl groups on the isoxazole–acridone skeleton;?they showed promising minimum inhibitory concentration values of 16.88 and 19.01 μg/ml, respectively, compared with the standard drug chloramphenicol (22.41 μg/ml). The synthesized compounds were subjected to in silico docking studies to understand the mode of their interactions with the DNA topoisomerase complex (PDB ID: 3FV5) of E. coli. The molecular docking results showed that compounds 4a–l occupy the active site of DNA topoisomerase (PDB ID: 3FV5), stabilized via hydrogen bonding and hydrophobic interactions, which may be the reason behind their interesting in vitro antibacterial activity.
- Aarjane, Mohammed,Slassi, Siham,Tazi, Bouchra,Amine, Amina
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- Synthesis, spectroscopic characterization (FT-IR, NMR) and DFT computational studies of new isoxazoline derived from acridone
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In this study, a new isoxazoline derived from acridone, 10‐{[3‐(4‐chlorophenyl)‐4,5‐dihydro‐1,2‐oxazol‐5 yl]methyl} acridone (3) was successfully synthesized and characterized by FT-IR, 1H NMR, 13C NMR and HRMS. The preparation of compound (3) was achieved by 1,3-dipolar cycloaddition reaction between 4?chloro-N-hydroxybenzimidoyl chloride and 10-allylacridone using environment friendly methods. In an effort to complete the chemical structure description of the synthetized compound, Density Functional Theory (DFT) was applied using Gaussian09 and Gaussian view5 programs. The theoretical calculations were used as a compliment to the experimental studies. The computing of geometric parameters, optimization energies, frontier molecular orbital energies, Molecular surface electrostatic potential (MESP) and Mulliken charges were calculated using DFT/B3LYP method with 6–31G(d,p) as basis set. The Infrared vibrational frequencies and 1H and 13C NMR chemical shifts were also calculated and their scaled values are in agreement with the experimental results.
- Aarjane, Mohammed,Slassi, Siham,Ghaleb, Adib,Amine, Amina
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- 2-arylamine compound and preparation method and application thereof
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The invention discloses a 2-arylamine compound and a preparation method and application thereof. The structure of the 2-arylamine compound is as shown in a formula I shown in the specification, wherein in the formula, the definition of each substituent group is as described in the specification and claims. The compound provided by the invention has a good inhibition effect on fatty acid binding protein 4, and can be used for prevention, treatment or adjuvant treatment of metabolic diseases, inflammations and cancers related to activity or expression of FABP4.
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Paragraph 0108-0111; 0154-0157
(2021/05/05)
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- Melatonin derivatives combat with inflammation-related cancer by targeting the Main Culprit STAT3
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The combination between two well-studied bioactive compounds melatonin and salicylic acid with proper modifications unexpectedly creates a sharp pair of “scissors” cutting off the vicious connection between inflammation and cancer by targeting a key contributor Signal Transducers and Activators of Transcription 3 (STAT3) in the two pathological processes. A representative compound P-3 with IC50 values on each tested cell line ranging from 7.37 to 18.62 μM among the designed melatonin derivatives is equipped with the ability of curbing inflammation-promoting cancer by down-regulating the expression, activation and nuclear translocation of STAT3, breaking the feedforward loop of STAT3 activation by decreasing the expression of pro-tumorigenic cytokines, and inducing cell apoptosis through ROS triggered Cyto-c/Caspase-3 pathway. This study suggests that the melatonin derivative P-3 is likely to become a promising chemical structure for developing the novel anti-cancer agents taking effect through hindering the mutual-promoting processes between inflammation and cancer.
- Ma, Shumeng,Zhu, Longqing,Fan, Xiaohong,Luo, Tian,Liu, Dan,Liang, Ziyi,Hu, Xiaoling,Shi, Tao,Tan, Wen,Wang, Zhen
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- Acid-catalyzed oxidative cross-coupling of acridans with silyl diazoenolates and a Rh-catalyzed rearrangement: two-step synthesis of γ-(9-acridanylidene)-β-keto esters
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A MsOH-catalyzed oxidative cross-coupling of acridans and silyl diazoenolates and a Rh2(OAc)4-catalyzed rearrangement of the resultant diazo products are described. The reactions provide various γ-(9-acridanylidene)-β-keto esters in good yields, which bear an active α-methylene unit for further functionalization.
- Li, Weiyu,Xu, Hao,Zhou, Lei
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supporting information
p. 5649 - 5657
(2021/07/02)
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- Novel highly selective and sensitive fluorescent sensor for copper detection based on N-acylhydrazone acridone derivative
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A new N-acylhydrazone based on acridone (S1) was synthesized by Schiff base condensation of 2-(9-oxoacridin-10-yl)acetohydrazide and salicylaldehyde and studied as selective fluorescence turn-off sensing towards Cu2+ ions in aqueous media. S1 demonstrated fluorescence turn-off sensing towards Cu2+ ions. Conversely, the metal ions K+, Mg2+, Zn2+, Fe2+, Al3+, Pb2+, Cr2+, Cd2+, Ag+, Fe3+, Ba2+, Hg2+, Mn2+, Co2+, and Ni2+ produced only minor decrease in the fluorescence of the system. The binding ratio of S1–Cu2+ complex was determined from the Job plot to be 1:2. Moreover, the S1–Cu2+ complex showed good fluorescence turn-off in presence of different counter ions of copper. In addition, the detection limit of S1 towards Cu2+ ions is 0.80 μM, which is enough for sensing the Cu2+ in the biological system and water within the U.S Environmental Protection Agency limit (~20 μM).
- Aarjane, Mohammed,Slassi, Siham,Amine, Amina
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- Design, synthesis and biological evaluation of acridone analogues as novel STING receptor agonists
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STING (Stimulator of Interferon Genes) has become a focal point in immunology research and a target in drug discovery. The discovery of a potent human-STING agonist is expected to revolutionize current anti-virus or cancer immunotherapy. Inspired by the structure and function of murine STING-specific agonists (DMXAA and CMA), we rationally designed and synthesized four series of novel compounds for the enhancement of human sensitivity. In the cell-based assay, we identified six compounds from all the synthetic small molecules: 2g, 9g, and 12b are STING agonists that are efficacious across species, and all have the skeleton of acridone; 1b, 1c, and 12c just function in the murine STING pathway. Notably, 12b exhibits the best activity among the six agonists, and its inductions of both human and murine STING-dependent signalling are similar to that of 2′3′-cGAMP, which is a well-known STING inducer. While a protein assay indicated that 2 g, 9 g, and 12b could activate the pathway by directly binding human STING, 12b also displayed the strongest binding affinity. Additionally, our studies show that 12b can induce faster, more powerful, and more durable responses of assorted cytokines in a native system than 2′3′-cGAMP. Consequently, our team is the first to successfully modify murine STING agonists to obtain human sensitivity, and these results suggest that 12b is a potent direct-human-STING agonist. Additionally, the acridone analogues demonstrate tremendous potential in the treatment of tumours or viral infections.
- Chang, Jia-jia,Hou, Shi,Lan, Xiu-juan,Li, Song,Li, Wei,Sun, Wei,Xiao, Jun-hai,Yan, Xin-lin,Yang, Xiao-hong
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- Synthesis, antibacterial evaluation and molecular docking studies of novel series of acridone- 1,2,3-triazole derivatives
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Development of new drugs with antibacterial potency is an important solution to overcome drug-resistance problems. In the goal to develop novel structure with antibacterial potency, we designed and synthesized novel acridone derivatives bearing triazole nucleus. The novel synthesized compounds were tested for their in vitro antibacterial activity against four bacterial human pathogenic strains. The compound 4h displayed significant antibacterial activities against Staphylcoccus aureus (MRSA) with MIC = 19.6?μg/mL. The synthesized compounds were subjected for docking study to understand the interaction of our compounds and the dihydropteroate synthase (DHPS) in methicillin-resistant Staphylcoccus aureus (MRSA).
- Aarjane, Mohammed,Slassi, Siham,Tazi, Bouchra,Maouloua, Mohamed,Amine, Amina
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p. 1523 - 1531
(2020/03/19)
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- Redox-neutral decarboxylative photocyclization of anthranilic acids
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A mild metal-, catalyst-, and oxidant-free photoredox neutral system has been found to efficiently enable intramolecular decarboxylative cyclization of anthranilic acids. This facile protocol provides an alternative method for the synthesis of carbazoles. Mechanistic studies reveal a key photoinduced 6π-electrocyclization process and formic acid was released as the sole byproduct.
- Huang, Huawen,Deng, Kun,Deng, Guo-Jun
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supporting information
p. 8243 - 8247
(2020/12/29)
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- Design, synthesis and biological evaluation of novel phthalazinone acridine derivatives as dual PARP and Topo inhibitors for potential anticancer agents
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In this study, we designed and synthesized a series of phthalazinone acridine derivatives as dual PARP and Topo inhibitors. MTT assays indicated that most of the compounds significantly inhibited multiple cancer cells proliferation. In addition, all the compounds displayed Topo II inhibition activity at 10 mol/L, and also possessed good PARP-1 inhibitory activities. Subsequent mechanistic studies showed that compound 9a induced remarkable apoptosis and caused prominent S cell cycle arrest in HCT116 cells. Our study suggested that 9a inhibiting Topo and PARP concurrently can be a potential lead compound for cancer therapy.
- Dai, Qiuzi,Chen, Jiwei,Gao, Chunmei,Sun, Qinsheng,Yuan, Zigao,Jiang, Yuyang
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p. 404 - 408
(2019/06/24)
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- N-o-substituted phenyl benzamide-4-methylamino acridine compound as well as preparation method and application thereof
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The invention discloses an N-o-substituted phenyl benzamide-4-methylamino acridine compound as well as a preparation method and application thereof. The compound is characterized in that the compoundis a compound with a structural formula shown as a formula I or pharmaceutically acceptable salt, ester or solvate thereof, wherein R1 is H, OCH3, OCH2CH3, F, Cl, Br, CF3, NO2 or straight-chain alkylwith a carbon atom number of 1-5; R2 is H, OCH3, OCH2CH3, F, Cl, Br, CF3, NO2 or straight-chain alkyl with a carbon atom number of 1 to 5; R3 is NH2, NHCH3, NHCH2CH3, OH, COOH, and SH, and R4 is H, OCH3 or linear alkyl with 1-5 carbon atoms and the like. The compound has the advantages that the compound can effectively inhibit DNA topoisomerase I, and proliferation of I-type HDAC and/or eukaryotictumor cells, and prevents and/or treats tumors.
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Paragraph 0024
(2020/05/05)
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- Synthesis method of N-phenyl aminobenzoic acid
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The invention belongs to the technical field of organic intermediate synthesis, and particularly relates to a synthesis method of N-phenyl aminobenzoic acid. The method comprises the following steps:(1) dissolving 2-chlorobenzonitrile and aniline in a solvent, adding K2CO3 and NaOH while stirring, and heating to carry out primary reflux reaction; (2) after the reflux reaction is finished, recovering the solvent under reduced pressure, then cooling the residual liquid, adding water, and heating to carry out secondary reflux reaction; and (3) cooling the reaction solution after the secondary reflux reaction in the step (2) to room temperature, extracting excessive aniline, adding diluted hydrochloric acid for neutralization while stirring a water phase, separating out a solid, filtering, and recrystallizing to obtain the target product N-phenyl aminobenzoic acid. According to the method, a one-pot process is adopted, under the condition that a catalyst is not used, 2-chlorobenzonitrileand aniline are used as raw materials for reaction, the target product with high purity (larger than 99%) and high yield (larger than 90%) is obtained, operation is easy, the raw materials are easy toobtain, the reaction is mild and easy to control, and aftertreatment is simple.
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Page/Page column 3-6
(2021/01/11)
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- Design, synthesis and biological evaluation of anthranilamide derivatives as potent SMO inhibitors
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A series of anthranilamide derivatives were designed and synthesized as novel smoothened (SMO) inhibitors based on the SMO inhibitor taladegib (LY2940680), which can also inhibit the SMO-D473H mutant, via a ring-opening strategy. The phthalazine core in LY2940680 was replaced with anthranilamide, which retained the inhibitory activity towards the hedgehog (Hh) signaling pathway as evidenced by a dual luciferase reporter gene assay. Compound 12a displayed the best inhibitory activity against the Hh signaling pathway with IC50 value of 34.09 nM, and exhibited better proliferation inhibitory activity towards the Daoy cell line (IC50 = 0.48 μM) than LY2940680 (IC50 = 0.79 μM).
- Ji, Dezhong,Xu, Yungen,Zhang, Jing-Jing,Zhang, Wanwan
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- Syntheses and Evaluation of New Bisacridine Derivatives for Dual Binding of G-Quadruplex and i-Motif in Regulating Oncogene c-myc Expression
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The c-myc oncogene is an important regulator for cell growth and differentiation, and its aberrant overexpression is closely related to the occurrence and development of various cancers. Thus, the suppression of c-myc transcription and expression has been investigated for cancer treatment. In this study, various new bisacridine derivatives were synthesized and evaluated for their binding with c-myc promoter G-quadruplex and i-motif. We found that a9 could bind to and stabilize both G-quadruplex and i-motif, resulting in the downregulation of c-myc gene transcription. a9 could inhibit cancer cell proliferation and induce SiHa cell apoptosis and cycle arrest. a9 exhibited tumor growth inhibition activity in a SiHa xenograft tumor model, which might be related to its binding with c-myc promoter G-quadruplex and i-motif. Our results suggested that a9 as a dual G-quadruplex/i-motif binder could be effective in both oncogene replication and transcription and become a promising lead compound for further development with improved potency and selectivity.
- Kuang, Guotao,Zhang, Meiling,Kang, Shuangshuang,Hu, Dexuan,Li, Xiaoya,Wei, Zuzhuang,Gong, Xue,An, Lin-Kun,Huang, Zhi-Shu,Shu, Bing,Li, Ding
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p. 9136 - 9153
(2020/10/18)
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- “On Water” promoted N-arylation reactions using Cu (0)/myo-inositol catalytic system
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Myo-inositol is originally applied as a cardiovascular medicine in clinic, which can be multi-ton manufactured via extraction from the byproducts in agricultural product processing such as defatted rice bran and corn-soaking water. Herein, the application of myo-inositol (MI) as a novel versatile tridentate O-donor ligand has been first described for promoting Cu-catalyzed amination reaction in aqueous medium.
- Zhou, Qifan,Du, Fangyu,Chen, Yuanguang,Fu, Yang,Chen, Guoliang
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supporting information
p. 1938 - 1941
(2019/06/24)
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- Methyl-α-d-glucopyranoside as Green Ligand for Selective Copper-Catalyzed N-Arylation
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In the selective N-arylation of amines or azoles with aryl halidesa-, methyl-α-d-glucopyranoside (MG) was found to function as a green ligand of copper powder. In addition, nitrogen heterocyclic amine compounds can also undergo the N-arylation coupling with heterocyclic aryl chlorides. This process allows access to a variety of aromatic amines and aryl azoles under mild reaction conditions, has good tolerance, and proceeds in moderate to high yield.
- Chen, Fengyang,Chen, Guoliang,Chen, Yuanguang,Du, Fangyu,Zhou, Qifan
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p. 4590 - 4600
(2019/12/11)
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- Light-Driven Intramolecular C?N Cross-Coupling via a Long-Lived Photoactive Photoisomer Complex
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Reported herein is a visible-light-driven intramolecular C?N cross-coupling reaction under mild reaction conditions (metal- and photocatalyst-free, at room temperature) via a long-lived photoactive photoisomer complex. This strategy was used to rapidly prepare the N-substituted polycyclic quinazolinone derivatives with a broad substrate scope (>50 examples) and further exploited to synthesize the natural products tryptanthrin, rutaecarpine, and their analogues. The success of gram-scale synthesis and solar-driven transformation, as well as promising tumor-suppressing biological activity, proves the potential of this strategy for practical applications. Mechanistic investigations, including control experiments, DFT calculations, UV-vis spectroscopy, EPR, and X-ray single-crystal structure of the key intermediate, provides insight into the mechanism.
- Jing, Dong,Lu, Cong,Chen, Zhuo,Jin, Songyang,Xie, Lijuan,Meng, Ziyi,Su, Zhishan,Zheng, Ke
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supporting information
p. 14666 - 14672
(2019/09/06)
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- Method 2 - for preparing FTO (FTO) inhibitor by using (substituted phenyl) benzoic acid and ester compound thereof
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The invention provides use of 2-(substituted phenylamino) benzoic acid and ester compound thereof in preparation of an FTO (Fat Mass and Obesity-Associated Protein) inhibitor. The invention particularly discloses the use of 2-(substituted phenylamino)-benzoic acid and the ester compound and a pharmaceutically acceptable salt thereof which are shown in the formula I in preparation of the FTO inhibitor or a pharmaceutical composition for treating FTO-related diseases.
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Paragraph 0121-0124
(2019/10/15)
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- Novel 9-(2-(1-arylethylidene)hydrazinyl)acridine derivatives: Target Topoisomerase 1 and growth inhibition of HeLa cancer cells
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A series of 9-(2-(1-arylethylidene)hydrazinyl)acridine and its analogs were designed, synthesized and evaluated for biological activities. Various biochemical assays were performed to determine the free radical scavenging capacity of synthesized compounds (4a–4j). Anticancer activity of these compounds was assessed against two different human cancer cell lines viz cervical cancer cells (HeLa)and liver cancer cells (HepG2)as well as normal human embryonic kidney cell line (HEK 293). Compounds 4b, 4d and 4e showed potential anti-proliferative effects on HeLa cells. Based on results obtained from antioxidant and cytotoxicity studies, 4b, 4d and 4e were further studied in detail for different biological activities. 4b, 4d and 4e reduced the cell growth, inhibited metastatic activity and declined the potential of cell migration in HeLa cell lines. Topoisomerase1 (Top1)treated with compounds 4b, 4d and 4e exhibited inhibition of Top1 and prevented DNA replication. Molecular docking results validate that interaction of compounds 4b, 4d and 4e with Top1-DNA complex, which might be accountable for their inhibitory effects. Further it was concluded that compounds 4b, 4d and 4e arrests the cells at S phase and consequently induces cell death through DNA damage in HeLa cells.
- Haider, Md Rafi,Ahmad, Kamal,Siddiqui, Nadeem,Ali, Zulphikar,Akhtar, Md Jawaid,Fuloria, Neeraj,Fuloria, Shivkanya,Ravichandran, Manickam,Yar, M. Shahar
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- 4-methylaminoacridine-N-phenylbenzamide compound and preparation method and application thereof
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The invention discloses a 4-aminomethylacridine-N-phenylbenzamide compound and a preparation method and application thereof. The compound is characterized in that the compound is a compound with a structural formula shown in the formula I or a pharmaceutically acceptable salt, ester or solvate of the compound with the structural formula shown in the formula I, wherein R1 is H, OCH3, OCH2CH3, Cl, Br, CF3, NO2 or a linear alkyl group with 1 to 5 carbon atoms, R2 is H, OCH3, OCH2CH3, Cl, Br, CF3, NO2 or a linear alkyl group with 1 to 5 carbon atoms, R3 is H, OCH3, OCH2CH3, Cl, Br, CF3, NO2 or a linear alkyl group with 1 to 5 carbon atoms, and n = 1, 2, 3 or 4, the advantages are that the compound can effectively inhibit the activity of DNA topoisomerases, inhibits the proliferation of eukaryotic tumor cells, and prevents and / or treats tumors.
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Paragraph 0021
(2019/11/14)
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- Targeting tyrosine kinase: Development of acridone – pyrrole – oxindole hybrids against human breast cancer
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Based on the molecular modelling studies, a rational modification of the lead molecule was made to develop highly potent compounds showing anti-cancer activity against human breast cancer cell lines MCF 7, MDA-MB-468 and T-47D. The most potent compounds have Log P and total polar surface area 4.4–5.4 and 59.8 ? respectively and they also exhibited promising ADME profile.
- Kaur, Manpreet,Singh, Palwinder
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supporting information
p. 32 - 35
(2018/11/23)
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- Synthesis and Antibacterial Activity of New N9-Substituted Acridine-9-amines
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A method for the synthesis of N9-substituted acridine-9-amines by reacting 9-chloroacridines with 2-(2-methyl-5- nitro-1H-imidazol-1-yl)ethanamine was developed. The synthesized compounds showed high antibacterial ability against B. subtilis bacteria compared with rivanol and metronidazole.
- Kudryavtseva,Bogatyrev,Sysoev,Klimova
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p. 157 - 159
(2019/04/13)
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- Design, synthesis and biological research of novel N-phenylbenzamide-4-methylamine acridine derivatives as potential topoisomerase I/II and apoptosis-inducing agents
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A series of novel N-phenylbenzamide-4-methylamine acridine derivatives were designed and synthesized based initially on the structure of amsacrine (m-AMSA). Molecular docking suggested that the representative compound 9a had affinity for binding DNA topoisomerase (Topo) II, which was comparable with that of m-AMSA, and furthermore that 9a could have preferential interactions with Topo I. After synthesis of 9a and analogues 9b-9f, these were all tested in vitro and the synthesized compounds displayed potent antiproliferative activity against three different cancer cell lines (K562, CCRF-CEM and U937). Among them, compounds 9b, 9c and 9d exhibiting the highest activity with IC50 value ranging from 0.82 to 0.91 μM against CCRF-CEM cells. In addition, 9b and 9d also showed high antiproliferative activity against U937 cells, with IC50 values of 0.33 and 0.23 μM, respectively. The pharmacological mechanistic studies of these compounds were evaluated by Topo I/II inhibition, western blot assay and cell apoptosis detection. In summary, 9b effectively inhibited the activity of Topo I/II and induced DNA damage in CCRF-CEM cells and, moreover, significantly induced cell apoptosis in a concentration-dependent manner. These observations provide new information and guidance for the structural optimization of more novel acridine derivatives.
- Zhang, Bin,Dou, Zhende,Xiong, Zheng,Wang, Ning,He, Shan,Yan, Xiaojun,Jin, Haixiao
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supporting information
(2019/10/28)
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- Copper(ii)-catalyzed c-n coupling of aryl halides and n-nucleophiles promoted by quebrachitol or diethylene glycol
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Herein, we report the natural ligand quebrachitol (QCT) as a promoter for a Cu(II) catalyst, which is highly effective for N-Arylation of various amines and related aryl halides. A series of diarylamine derivatives were obtained in high yields by using diethylene glycol (DEG) as both ligand and solvent. The C-N coupling reactions proceed under mild conditions and exhibit good functional group tolerance.
- Chen, Guoliang,Chen, Yuanguang,Du, Fangyu,Fu, Yang,Wu, Ying,Zhou, Qifan
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supporting information
p. 2161 - 2168
(2019/11/25)
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- A new kind of acetylcholine esterase inhibitors and its preparation method and application (by machine translation)
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The present invention provides a novel acetyl choline esterase inhibitor and its preparation method and application, in particular, the invention discloses a formula A shown with double AChE binding site of substituted acridine compound, and its preparation method and as acetylcholinesterase inhibitors. The preparation of the novel compounds of this invention demonstrate good inhibit acetylcholine esterase role, can be used as a preparation for treating and preventing HAMER (AD) application value. (by machine translation)
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Paragraph 0090; 0091
(2018/04/03)
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- Synthesis and biological study of acridine-based imidazolium salts
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A new series of acridine based imidazolium salts was synthesized and evaluated for in vitro cytotoxicity against human cancer cell lines by an MTT assay. The synthesis applied a coupling of imidazoles with 9-chloroacridines, which originated from an Ullmann condensation of a 2-chloro-benzoic acid with an aniline. The target compounds were obtained in high yields. The DPPH assay indicated considerable antioxidant activity for target compounds with simple and short alkyl chains on the imidazole, while increasing chain length and the introduction of an additional π-electron system in most cases reduced the activity. All compounds exhibited low biotoxicity against non-cancerous cell lines, whereas a few compounds showed promising anticancer activity. Unlike for the reference drugs Tamoxifen and Paclitaxel, the anticancer activity of acridine imidazolium ions is specific for only selected cancer types. Reasonable fluorescent behaviour of the products provide potential for visualization of the distribution of active drugs in tissue.
- Sharhan, Olla,Heidelberg, Thorsten,Hashim, Najiahah Mohd,Salman, Abbas Abdulameer,Ali, Hapipah Mohd,Jayash, Soher Nagi
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p. 38995 - 39004
(2018/12/02)
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- Design and synthesis of some acridine-piperazine hybrids for the improvement of cognitive dysfunction
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A novel series of hybrid molecules (5a–5m) was designed, synthesized and evaluated as multifunctional cholinesterase (ChE) inhibitors against cognitive dysfunction. Heterocyclic moieties acridine and piperazine were conjugated with suitable linkers in a single scaffold, and the structures of the target compounds were confirmed by IR, 1H NMR, 13C NMR, and LC-MS analysis. The pharmacological activity of synthesized compounds was evaluated using behavioral models of amnesia viz. step-down passive avoidance and elevated plus maze at a dose 0.5?mg/kg as compared to standard rivastigmine. In vitro acetylcholinesterase (AChE) inhibition studies using brain homogenate of mice as the enzyme source revealed that most of the compounds exhibited a significant ability to inhibit the enzyme cholinesterase with compound 5c being the most potent (IC50 0.33?μm). Biochemical estimation of oxidative stress markers viz. plasma nitrite, thiobarbituric acid reactive substances, catalase, superoxide dismutase, and glutathione has been carried out using the respective assays to see the effect of the synthesized compounds on the scopolamine-induced oxidative damage. The molecular docking studies indicated the binding mode of the compounds to the catalytic site, peripheral site, and mid-gorge of AChE simultaneously. The calculated absorption, distribution, metabolism and excretion properties ensured the drug-likeness of the target compounds. The synthesized compounds were found to be potential cognitive enhancers, which were able to interfere with the scopolamine-induced oxidative stress also.
- Sharma, Anuradha,Piplani, Poonam
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p. 926 - 935
(2017/10/06)
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- Synthesis of methyl 2-[(1,2-dihydro-4-hydroxy-2-oxo-1-phenylquinolin-3-yl) carbonylamino] alkanoates and methyl 2-[2-((1,2-dihydro-4-hydroxy-2-oxo-1-phenylquinolin-3-yl)carbonyl-amino)alkanamido] alkanoate
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A series of methyl 2-[(1,2-dihydro-4-hydroxy-2-oxo-1-phenylquinolin-3-yl)carbonylamino] alkanoates 7a-f has been developed by the direct condensation of ethyl [4-hydroxy-2-oxo-1-phenyl-1,2-dihydro-3-quinoline] carboxylate 4 with amino acid ester hydrochloride in the presence of triethylamine. The quinoline amino acid esters 7a-f were the key intermediate for the preparation of a series of methyl 2-[2-((1,2-dihydro-4-hydroxy-2-oxo-1-phenylquinolin-3-yl)carbonylamino)alkanamido] alkanoate 10-13(a-f) via azide coupling method with amino acid ester. {figure presented}.
- Fathalla, Walid,Pazdera, Pavel
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p. 158 - 173
(2017/06/19)
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- Design, synthesis and biological evaluation of 4-amidobenzimidazole acridine derivatives as dual PARP and Topo inhibitors for cancer therapy
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PARP-1 could repair the DNA damages induced by Topo inhibitors, therefore inhibiting Topo and PARP-1 simultaneously might be able to overcome resistance and improve outcomes. In this study a series of 4-amidobenzimidazole acridines were designed and synthesized as dual Topo and PARP-1 inhibitors. Compound 11l displayed good inhibitory activities against Topo and PARP-1, as well as significantly inhibited cancer cells proliferation. Further mechanistic evaluations indicated that 11l treatment in MCF-7 cells induced accumulated DNA double-strand breaks, prompted remarkable apoptosis, and caused prominent G0/G1 cell cycle arrest. Moreover, 11l greatly suppressed tumor growth in mice, and displayed favorable metabolic properties in liver microsomes. Our study suggested that single agents inhibiting Topo and PARP concurrently might be an alternative for cancer therapy and 11l represented a potential lead compound for development of antitumor agents.
- Yuan, Zigao,Chen, Shaopeng,Chen, Changjun,Chen, Jiwei,Chen, Chengken,Dai, Qiuzi,Gao, Chunmei,Jiang, Yuyang
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p. 1135 - 1146
(2017/08/02)
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- Design, synthesis, pharmacological evaluation, and docking study of new acridone-based 1,2,4-oxadiazoles as potential anticonvulsant agents
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A number of acridone-based oxadiazoles 11a–n have been synthesized and evaluated for their anticonvulsant activity against pentylenetetrazole (PTZ)- and maximal electroshock (MES)-induced seizures in mice. Also, their neurotoxicity was evaluated by the rotarod test. Most of the compounds exhibited better anticonvulsant activity and higher safety respect to the standard drug, phenobarbital. Among the tested derivatives, compounds 11l with ED50value of 2.08?mg/kg was the most potent compound in the PTZ test. The anticonvulsant effect of compound 11l was blocked by flumazenil, suggesting the involvement of benzodiazepine (BZD) receptors in the anticonvulsant activity of prototype compound 11l. Also, docking study of compound 11l in the BZD-binding site of GABAAreceptor confirms possible binding of compound 11l with BZD receptors.
- Mohammadi-Khanaposhtani, Maryam,Shabani, Mohammad,Faizi, Mehrdad,Aghaei, Iraj,Jahani, Reza,Sharafi, Zainab,Shamsaei Zafarghandi, Narges,Mahdavi, Mohammad,Akbarzadeh, Tahmineh,Emami, Saeed,Shafiee, Abbas,Foroumadi, Alireza
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- Development of acridine derivatives as selective Mycobacterium tuberculosis DNA gyrase inhibitors
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In this study we have designed p-phenylene diamine linked acridine derivative from our earlier reported quinoline-aminopiperidine hybrid MTB DNA gyrase inhibitors with aiming more potency and less cardiotoxicity. We synthesized thirty six compounds using four step synthesis from 2-chloro benzoic acid. Among them compound 4-chloro-N-(4-((2-methylacridin-9-yl)amino)phenyl)benzenesulphonamide (6) was found to be more potent with MTB DNA gyrase super coiling IC50of 5.21 ± 0.51 μM; MTB MIC of 6.59 μM and no zHERG cardiotoxicity at 30 μM and 11.78% inhibition at 50 μM against mouse macrophage cell line RAW 264.7.
- Medapi, Brahmam,Meda, Nikhila,Kulkarni, Pushkar,Yogeeswari, Perumal,Sriram, Dharmarajan
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p. 877 - 885
(2016/05/24)
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- Antitumor compound and preparation method thereof
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The present invention is an antitumor compound belonging to the field of medicines, and particularly relates to an antitumor-active compound with a specific chemical structure and a preparation method and use of the antitumor-active compound. The antitumor-active compound is as shown in a general formula, wherein n is an integer from 0 to 3, R1 is methyl, fluorine, chlorine, bromine, carboxyl and a methyl ester, an ethyl ester, a propyl ester, an isopropyl ester, a n-butyl ester, an iso-butyl ester and a tert-butyl ester, R2 is acetyl, propionyl, benzoyl, and an alkyl group having 1-5 carbon atoms, X is CH2 or CO (carbonyl); positions of substituents on the aromatic ring may be 2-site-substituted, 3-site-substituted and 4-site-substituted, and the substitution may be mono-substituted and poly-substituted. The present invention provides the preparation method of the antitumor-active compound. Experiments show that the antitumor-active compound as a new-structure-type topoisomerase inhibitor plays a good role in inhibition of tumor activity.
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Paragraph 0059; 0060
(2016/10/09)
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- Synthesis and antiproliferative activity of 6,7-disubstituted-4-phenoxyquinoline derivatives bearing the 2-oxo-4-chloro-1,2-dihydroquinoline-3-carboxamide moiety
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A series of 6,7-disubstituted-4-phenoxyquinoline derivatives bearing the 2-oxo-4-chloro-1,2-dihydroquinoline-3-carboxamide moiety were synthesized, and evaluated for their antiproliferative activity against 5 cancer cell lines (H460, HT-29, MKN-45, A549, and U87MG). Most compounds showed moderate to excellent potency, and compared to foretinib, the most promising analog 42 (c-Met/Flt-3 IC50= 1.21/2.15 nM) showed a 6.1-fold increase in activity against H460 cell line in vitro. The enzymatic assays (c-Met, VEGFR-2, Flt-3, PDGFR-β, c-Kit, and EGFR) of compound 42 were evaluated in vitro. Docking analysis showed that compound 42 could form three hydrogen bonds with c-Met. Structure–activity relationship studies indicated that a more water-soluble cyclic tertiary amine and electron-withdrawing groups at 4-position of the phenyl ring contribute to the antitumour activity.
- Tang, Qidong,Zhai, Xin,Tu, Yayi,Wang, Ping,Wang, Linxiao,Wu, Chunjiang,Wang, Wenhui,Xie, Hongbo,Gong, Ping,Zheng, Pengwu
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p. 1794 - 1798
(2016/12/22)
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- 9-amino acridine derivative and its synthetic method
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The invention discloses a novel aminoacridine derivative, and particularly relates to a 9-aminoacridine derivative and a synthetic method thereof, belonging to the technical field of organic chemical synthesis. The structure of the 9-aminoacridine derivative is shown in the specification, wherein R1 and R2 are independently selected from H, methoxyl, C1-C10 alkyl and C1-C10 halo-alkyl. The compound has better fluorescence property and can be applied to an organic light-emitting material.
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Paragraph 0036; 0037; 0038
(2017/02/02)
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- Bifunctional AKR1C3 inhibitors/androgen receptor modulators and methods of use thereof
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The invention includes compositions comprising selective AKR1C3 inhibitors. The invention also includes compositions comprising bifunctional AKR1C3 inhibitors and selective androgen receptor modulators. The invention further includes methods of treatment using the compositions of the invention.
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Page/Page column 58; 59; 60
(2016/03/19)
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- Potent acetylcholinesterase inhibitors: Design, synthesis, biological evaluation, and docking study of acridone linked to 1,2,3-triazole derivatives
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A novel series of acridone linked to 1,2,3-triazole derivatives have been synthesized and evaluated in vitro for their acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities. The synthetic approach was started from the reaction of 2-bromobenzoic acid with aniline derivatives and subsequent cyclization reaction to give acridone derivatives. Then, reaction of the later compounds with propargyl bromide followed by azide-alkyne cycloaddition reaction (click reaction) led to the formation of the title compounds in good yields. Among the synthesized compounds, 10-((1-(4-chlorobenzyl)-1H-1,2,3-triazol-4-yl)methyl)-2-methoxyacridin-9(10H)-one 9g, depicted the most potent anti-AChE activity (IC50 Combining double low line 7.31 μ1/4M). Also, docking study confirmed the results obtained through in vitro experiments and predicted possible binding conformation.
- Mohammadi-Khanaposhtani, Maryam,Saeedi, Mina,Zafarghandi, Narges Shamsaei,Mahdavi, Mohammad,Sabourian, Reyhaneh,Razkenari, Elahe Karimpour,Alinezhad, Heshmatollah,Khanavi, Mahnaz,Foroumadi, Alireza,Shafiee, Abbas,Akbarzadeh, Tahmineh
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p. 799 - 806
(2015/03/05)
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- Design, synthesis, in vitro cytotoxic activity evaluation, and apoptosis-induction study of new 9(10H-acridinone-1,2,3-triazoles
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A new series of 9(10H-acridinone-1,2,3-triazole derivatives were designed, synthesized and evaluated for their cytotoxic activity against human breast cancer cell lines. The acridone skeleton was prepared through the Ullman condensation of 2-bromobenzoic acid and anilines. Subsequently, it was functionalized with propargyl bromide. Then, a click reaction of the latter compound and in situ prepared 1-(azidomethyl)-4-methoxybenzene derivatives led to the formation of the desired triazole products. Finally, all products were investigated for their capability to cause cytotoxicity against MCF-7, T-47D, and MDA-MB-231 cell lines. Among them, 2-methoxy-10-((1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)methyl)acridin-9(10H-one 8c exhibited the most potency (hbox {IC}_{50},{=},11.0,{pm }, 4.8, upmu hbox {M})(IC50=11.0±4.8μM) against MCF-7 cells, being more potent than etoposide (hbox {IC}_{50},{=}, 12.4,{pm }, 4.7 upmu hbox {M})(IC50=12.4±4.7μM). Also, apoptosis induced by compound 8c was confirmed via acridine orange/ethidium bromide and Annexin V-FITC/propidium iodide (PI) double staining.
- Mohammadi-Khanaposhtani, Maryam,Safavi, Maliheh,Sabourian, Reyhaneh,Mahdavi, Mohammad,Pordeli, Mahboobeh,Saeedi, Mina,Ardestani, Sussan Kabudanian,Foroumadi, Alireza,Shafiee, Abbas,Akbarzadeh, Tahmineh
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p. 787 - 795
(2015/10/12)
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- Design, synthesis, biological evaluation, and docking study of acetylcholinesterase inhibitors: New acridone-1,2,4-oxadiazole-1,2,3-triazole hybrids
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In this study, novel acridone-1,2,4-oxadiazole-1,2,3-triazole hybrids were designed, synthesized, and evaluated for their acetylcholinesterase and butyrylcholinesterase inhibitory activity. Among various synthesized compounds, 10-((1-((3-(4-methoxyphenyl)-1,2,4-oxadiazol-5-yl)methyl)-1H-1,2,3-triazol-4-yl)methyl)acridin-9(10H)-one 10b showed the most potent anti-acetylcholinesterase activity (IC50 = 11.55 μm) being as potent as rivastigmine. Also docking outcomes were in good agreement with in vitro results confirming the dual binding inhibitory activity of compound 10b. A novel series of acridone-1,2,4-oxadiazole-1,2,3-triazole hybrids were synthesized and evaluated in vitro for their acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities.
- Mohammadi-Khanaposhtani, Maryam,Mahdavi, Mohammad,Saeedi, Mina,Sabourian, Reyhaneh,Safavi, Maliheh,Khanavi, Mahnaz,Foroumadi, Alireza,Shafiee, Abbas,Akbarzadeh, Tahmineh
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p. 1425 - 1432
(2016/02/05)
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- Synthesis and biological evaluation of benzimidazole acridine derivatives as potential DNA-binding and apoptosis-inducing agents
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The discovery of new effective DNA-targeted antitumor agent is needed because of their clinical significance. As acridines can intercalate into DNA and benzimidazoles have the ability to bind in the DNA minor groove, a series of novel benzimidazole acridine derivatives were designed and synthesized to be new DNA-targeted compounds. MTT assay indicated that most of the synthesized compounds displayed good antiproliferative activity, among which compound 8l demonstrated the highest activity against both K562 and HepG-2 cells. Further experiments showed that 8l displayed good DNA-binding capability and inhibited topoisomerase I activity. Moreover, compound 8l could induce apoptosis in K562 cell lines through mitochondrial pathway. These data suggested that compound 8l might be potential as new DNA-binding and apoptosis-inducing antitumor agents.
- Gao, Chunmei,Li, Bin,Zhang, Bin,Sun, Qinsheng,Li, Lulu,Li, Xi,Chen, Changjun,Tan, Chunyan,Liu, Hongxia,Jiang, Yuyang
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supporting information
p. 1800 - 1807
(2015/03/30)
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- NIS-mediated intramolecular oxidative α-functionalization of tertiary amines: Transition metal-free synthesis of 1,2-dihydro-(4H)-3,1-benzoxazin-4-one derivatives
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A novel method for direct α-functionalization of tertiary amines via NIS-mediated oxidative C-O bond formation, where NIS serves as both an oxidant and an iodination reagent, has been developed. The method provides easy access to either iodinated or non-iodinated 1,2-dihydro-(4H)-3,1-benzoxazin-4-ones, depending on the nature of the reactant, via a regioselective transition metal-free approach. This journal is
- Liu, Le,Du, Liang,Zhang-Negrerie,Du, Yunfei
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p. 29774 - 29781
(2015/05/20)
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- NOVEL ANTHRANILIC AMIDES AND THE USE THEREOF
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Disclosed are anthranilic amide derivatives having the formula. Compositions are disclosed that include the anthranilic amide derivatives and the use of the anthranilic amide derivatives for the manufacture of a medicament. Further disclosed are methods of inhibiting or treating cancer, inhibiting or reversing an epithelial to mesenchymal cellular transition, and/or inhibiting MEKI/2 and/or MEK 5 enzymatic activity in a subject by administering to the subject an effective amount of a disclosed anthranilic amide derivative.
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Paragraph 0157
(2015/03/28)
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