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Synthesis and antiproliferative evaluation of quinoline bearing amide and oxime derivatives

Synthesis and antiproliferative evaluation of quinoline bear...

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第11届世界华人药物化学研讨会（iscmc 2018）

作者： Taichi,Wang Shinhun Juang Ili Chen Department of Pharmacy Tajen University

Compounds contain with a-methylene-γ-butyrolactone ring and/or amide functional groups can be found in natural products and has been reported with variety ***,several derivatives with such substituents and/or oxime substituted have been synthesized and demonstrated to have a wide range of biological activities including antitumor,bactericidal,fungicidal,anthelminthic and *** our previous study,although the average growth inhibitory activity of amide-substituted 3,4-dihydroquinoIin-2(1 H)-one(Amide-HQO)against toward the four human cancer cells(NCI-H661,Hep3 B,A498,MKN45) are not significant,but data showed the nasopharyngeal cell(NPC-TW01) is more sensitive to the Amide-HQO *** further improve the growth inhibitory potency,increase cell type specificity and explore the structure-activity relationships,a series of oxime and amide substituted 8-quinoline and 2-methyl-8-quinoline derivatives were *** preliminary results showed the newly synthesized compounds indeed demonstrated increase the potency toward the NPC-TW01 but also dramatically inhibited the human lung cancer cell(H226).These data indicated that these compounds could serve as good leads to develop more potent cytotoxic agents for lung cancer treatment.

关键词： structure-activity relationships oxime/amide substituted 8-quinoline cytotoxic agents

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Ethyl pyruvate protects against salmonella intestinal infection in mice through down-regulation of pro-inflammatory factors involving TLR4/p38MAPK pathway

Ethyl pyruvate protects against salmonella intestinal infect...

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第11届世界华人药物化学研讨会（iscmc 2018）

作者： Xinyao Xu Chenyu Xue Chensi Wang Xinran Li Na Dong Animal Science and Technology Collage Northeast Agricultural University

Salmonella typhimurium is one of the main causes of intestinal diseases,harming the health of humans and ***,an effective drug for the treatment of enteritis induced by Salmonella typhimurium is hopefully *** pyruvate（EP） has been proven to exert anti-inflammatory effects and protect the intestinal barrier ***,no systematic study was actualized in EP inhibiting Salmonella intestinal *** this study,intestinal immune function and pathway mediated by EP was investigated in Salmonella typhimurium-chanllenged mice *** showed that EP improved the body weight loss and organ index of liver and *** and IgM in serum had a significant rise in EP-treated *** result of histology demonstrated that EP significantly increased jejunum villus height and crypt depth and inhibited of occludin and ZO-1 mRNA expression decreasing in infected *** addition,EP decreased IL-6,IL-1β and TNF-α mRNA level in jejunum,liver and ***4 mRNA and phosphorylation of p38 MAPK were inhibited by EP in infected *** conclusion,EP reduced inflammation by protecting the jejunal barrier,inhibition of IL-6,IL-1β,TNF-α and TLR4 mRNA and phosphorylation of p38 in infected mice.

关键词： Ethyl pyruvate Salmonella typhimurium Intestine Immunity MAPK

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OBHSA compounds with different side chains as SERDs reveal structure-activity relationships in ER+ breast cancer cells

OBHSA compounds with different side chains as SERDs reveal s...

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第11届世界华人药物化学研讨会（iscmc 2018）

作者： Yuanyuan Li Jing Zhang Min He Zhiye Hu Silong Zhang Chune Dong Haibing Zhou School of Pharmaceutical Sciences Wuhan University

As the mutant ER continually being identified,breast cancer becomes more and more difficult to be cured when treated with hormone *** 2012,our group reported the oxabicycloheptene sulfonamide（OBHSA） compounds as full ER antagonists, furthermore John Katzenellenbogen's group revealed the new mechanism of these compounds as SERDs last year. Herein,to search for new antiestrogens more effective in treating breast cancers,we use the OBHSA as core and explore alternatives to the basic side chain,long alkyl acid side chain and glycerol ether side chain used in many antiestrogens,and then investigate the structure-activity relationships between these compounds in MCF-7 *** compounds can inhibit the breast cancer cell *** compounds with basic side chain gave the best results,while compounds with the long alkyl acidic side chain and the glycerol ether side chain had good to modest *** the substituents on the N-position of the sulfonamide,compounds with ethyl and trifluoromethyl group showed very good results and compounds with methyl group exhibited modest IC *** docking study of these compounds elucidates their structure-activity relationships,which provides guidance to design biologically distinct molecules for ER ligands to treat breast cancer.

关键词： structure-activity relationship side chain SOBHA ER+ breast cancer

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Exploration of novel pyrrolo[2,1-f]triazine derivatives with improved anticancer efficacy as dual inhibitors of c-Met/VEGFR-2

Exploration of novel pyrrolo[2,1-f]triazine derivatives with...

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第11届世界华人药物化学研讨会（iscmc 2018）

作者： Yuxuan Dai Hai Qian Center of Drug Discovery State Key Laboratory of Natural MedicinesChina Pharmaceutical University Jiangsu Key Laboratory of Drug Discovery for Metabolic Disease China Pharmaceutical University

c-Met and VEGFR-2 have attracted interest as novel targets for the development of tumor angiogenesis and progression in various human ***,a series of pyrrolo[1,2-f][1,2,4]triazine derivatives were designed and synthesized based on the moieties of Cabozantinib and Foretinib to afford potent dual c-Met and VEGFR-2 *** privileged compounds exhibited potent antiproliferative effect against c-Met addictive cancer cell lines with IC values ranged from 1.2 to 24.6 *** particular,the optimized compound exhibited the nanomolar potent inhibitory activity against c-Met and VEGFR-2 in vitro enzymatic assays and great selectivity,*** also showed the highest anticancer activity against the tested cell lines,with IC of 0.71 ± 0.16 nM against BaF3-TPR-Met and37.4 ± 0.311 nM against ***,physicochemical and pharmacokinetic characterization of the compound showed favorable draggability and pharmacokinetic *** molecular docking studies suggested a common mode of interaction at the ATP-binding site of c-Met and VEGFR-2,also indicating that compound was a potential candidate for cancer therapy deserving further study.

关键词： c-Met VEGFR-2 cancer

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Discovery of aromatic amides with triazole-core as potent reversal agents against P-glycoprotein-mediated multidrug resistance

Discovery of aromatic amides with triazole-core as potent re...

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第11届世界华人药物化学研讨会（iscmc 2018）

作者： Wei Shi Hai Qian Center of Drug Discovery State Key Laboratory of Natural MedicinesChina Pharmaceutical University Jiangsu Key Laboratory of Drug Discovery for Metabolic Disease China Pharmaceutical University

P-glycoprotein（P-gp）-mediated multidrug resistance（MDR） is a major impediment for clinical cancer therapy.33 novel aromatic amides with triazole-core as MDR reversal agents were designed and synthesized via click chemistry to reverse *** them,compound 67 was identified as the most promising candidate with high potency(EC= 46.83± 4.6 nM),low cytotoxity（T1 > 2135） and persistent duration in reversing doxorubicin（DOX）resistance in K562/A02 cells.67 also enhanced the potency of other P-gp associated cytotoxic agents with different *** further study,remarkably increased intracellular accumulation of Rhl23 and DOX in K562/A02 cells was achieved by compound 67,and it could also suppress Rhl23-efflux effect of P-gp,while CYP3 A4 activity or P-gp expression had no change by compound *** results indicate that compound 67 as a relatively safe modulator of P-gp-mediated MDR has good potential for further development

关键词： P-glycoprotein Multidrug resistance Reversal agents Click chemistry

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Design and synthesis of novel steriodal imidazoles as dual inhibitors of AR/CYP17 for the treatment of prostate cancer

Design and synthesis of novel steriodal imidazoles as dual i...

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第11届世界华人药物化学研讨会（iscmc 2018）

作者： Qiangqiang Hou Conghui He Hua Xiang Jiangsu Key Laboratory of Drug Design and Optimization China Pharmaceutical University

Prostate cancer（PC） is one of the major lethal causes from malignancies in males,and the androgen signaling pathway plays a crucial role in the development and progression of *** AR and CYP17 are important targets for blocking androgen *** previous studies found that androstane-17-β-benzamide exerted promising AR inhibitory activity(IC=16.84μM).Herein,by rational optimization of this hit,a series of steriodal imidazoles were designed,synthesized and evaluated as dual AR/CYP17 *** compounds displayed good biological profiles in both enzymatic and cellular *** studies showed that introducing oximino at the C-3 position of steriodal scaffold is benificial to the enhancement of AR binding *** these compounds,the most potent compound19 b exhibited excellent CYP17 inhibition(IC=2.818μM) as well as outstanding AR inhibition(IC=0.607μM) that was 27-fold increase compared with the hit ***,the docking results of 19 b suggested that the oxygen atom at the position of C-3 connected to the heme of CYP17,which may be helpful for its satisfactory dual-target *** summary,this study explored a new avenue for the development of novel multifunctional agents in the treatment of prostate cancer.

关键词： AR antagonists CYP17 inhibitors prostate cancer design synthesis

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Design,synthesis and biological evaluation of limonin derivatives

Design,synthesis and biological evaluation of limonin deriva...

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第11届世界华人药物化学研讨会（iscmc 2018）

作者：梁停停贾成舒朱启华徐云根 State Key Laboratory of Natural Medicines China Pharmaceutical University Department of Medicinal Chemistry China Pharmaceutical University

Limonoids,typical secondary metabolites in the Rutaceae and Meliaceae family plants,are highly oxygenated tetranortripenoid with a skeleton of 4,4,*** recent years,researchers found that limonoids have a wide range of biological activities,including but not limited to analgesic,anti-inflammation,antitumor,anti-microbial and insect anti-feedant ***,limonin is of moderate polarity and insoluble in water,which results in low oral bioavailability,greatly limiting its clinical *** this study,we chose limonin as lead compound,a series of novel derivatives were designed and synthesized by introducing various tertiary amine groups to the furan ring of *** the target compounds were evaluated for their anti-inflammatory and analgesic activities in *** of the compounds exhibited moderate to strong anti-inflammatory and analgesic *** them,compounds I-C-1· HC1 and I-C-2·HC1 show better anti-inflammatory activities than limonin and naproxen in the xylene-induced ear swelling test in mice,and they also exhibit stronger analgesic activities than limonin in the acetic acid-induced writhing response in mice test and hot water-induced tail retracting in mice *** candidate compounds,their LD in mice is greater than 2 g/kg,and their depressant effects on IKr are weak and the risk of inducing LQT is tiny.

关键词： limonin anti-inflammatory analgesic tertiary amine groups

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Novel triazole nucleosides:from bioactive molecules to supramolecular self-assemblies for targeted therapy

Novel triazole nucleosides:from bioactive molecules to supra...

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第11届世界华人药物化学研讨会（iscmc 2018）

作者： Yanhua Zhang Mimi Chen Mengyao Li Ling Peng Yi Xia Chongqing Key Laboratory of Natural Product Synthesis and Drug Research School of Pharmaceutical SciencesChongqing University Aix-Marseille Université Centre Interdisciplinaire de Nanoscience de Marseille

Synthetic nucleoside analogues can mimic natural nucleosides hence to interfere the nucleic acid synthesis and/or nucleos（t）ide involving enzymes,leading to potent and effective biological *** our ongoing efforts to discover new structural paradigms as drug candidates,we have developed green and efficient chemistry to establish original 1,2,4-triazole nucleoside analogues bearing the aromatic *** identified hits from these triazole derivatives have exhibited great potential to prevent tumor growth with novel mechanisms of action,as well as to inhibit pathogenic ***,the novel conjugates made from 1,2,4-triazole nucleosides with lipids or macromolecules have been developed to achieve active targeting by altering the pharmacological profile of the leads. It is to note that the triazole nucleoside based bola-amphiphiles not only possess of dual anticancer and antibacterial activity,also are able to form supramolecular assemblies for targeted therapy. Our work therefore empower the practicality of diversely reactions for generating structurally challenging chemical entities,as well as encourage to search for biologically active molecules and delivery system to combat various diseases.

关键词： Triazole nucleosides Biological activities Novel mechanism of action Supramolecular self-assemblies

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The medicinal chemistry,chemical biology of natural(+)-calanolide A and its anti HIV-1,anti Mtb drug leads optimization and diagnosis of tuberculosis

The medicinal chemistry,chemical biology of natural(+)-calan...

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第11届世界华人药物化学研讨会（iscmc 2018）

作者： Gang Liu School of Pharmaceutical Sciences Tsinghua University

Natural（+）-Calanolide A was discovered for its anti HIV-1 and anti Mtb activities Since 2000,our laboratory investigated（+）-Calanolide A's medicinal chemistry aiming at the assay of structure activity relationship（SAR） and lead compound optimization of draggable *** found that an analog of F18 was extremely sensitive to clinical mutant Y181 C of human HIV-1 and significantly synergize with anti HIV-l drugs including NTRIs,NNTRIs,and protein's inhibitors.F18's preclinical investigation was archived. Further systemic SAR studies revealed that 9,10-nitrofuran derivatives of（+）-Calanolide A（NFCs） showed significantly mycobactericidal activity to both replicating and non-replicating Mtb in vitro and in macrophage with acceptable selective *** of NFCs stopped its further draggable development. Recent studies disclosed that NFCs targets at a novel nitrooxidoreducase Rv2466 c,which reduced the nitro group of NFCs into corresponding amino NFC compound. The later was highly excited fluorescence by enzymatic Rv2466 c,BCO and Mtb that has been set up a "off to on" technology for diagnosis of Mtb in *** report reviews the past of（+）-Calanolide A:from the discovery of natural product to medicinal chemistry,chemical biology,and the current application for diagnosis of tuberculosis.

关键词： (+)-Calanolide A HIV-1 tuberculosis drug diagnostic reagent

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Small-molecule activator of UNC-51-like kinase 1(ULK1) that induces cytoprotective autophagy for Parkinson's disease treatment

Small-molecule activator of UNC-51-like kinase 1(ULK1) that ...

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第11届世界华人药物化学研讨会（iscmc 2018）

作者： Lan Zhang Guan Wang Liang Ouyang State Key Laboratory of Biotherapy and Cancer Center West China HospitalSichuan University

UNC-51-like kinase 1（ULK1）,the yeast Atgl ortholog,is the sole serine-threonine kinase and initiating enzyme in autophagy,which may be regarded as a target in Parkinson's disease（PD）.Herein,we discovered a small molecule 33 i（BL-918） as a potent activator of ULK1 by structure-based drug ***,some key amino acid residues（Arg18,LysSO,Asn86 and Tyr89） were found to be crucial to the binding pocket between ULK1 and 331 by site-directed ***,we found that 331 induced autophagy via the ULK complex in SH-SY5 Y ***,this activator displayed a cytoprotective effect on MPP-treated SH-SYSY cells,as well as protected against MPTP-induced motor dysfunction and loss of dopaminergic neurons by targeting ULK1-modulated autophagy in mouse models of ***,these results demonstrate the therapeutic potential to target ULK1,and 331,the novel activator of ULK1 may serve as a candidate drug for future PD treatment.

关键词： UNC-51-like kinase 1 Autophagy Parkinson's disease ULK1 activator The ULK complex

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