Camphor-based symmetric diimines as inhibitors of influenza virus reproduction.


:Influenza is a continuing world-wide public health problem that causes significant morbidity and mortality during seasonal epidemics and sporadic pandemics. The purpose of the study was synthesis and investigation of antiviral activity of camphor-based symmetric diimines and diamines. A set of C2-symmetric nitrogen-containing camphor derivatives have been synthesized. The antiviral activity of these compounds was studied against rimantadine- and amantadine-resistant influenza virus A/California/7/09 (H1N1)pdm09 in MDCK cells. The highest efficacy in virus inhibiting was shown for compounds 2a-e with cage moieties bound by aliphatic linkers. The therapeutic index (selectivity index) for 2b exceeded that for reference compounds amantadine, deitiforin and rimantadine almost 10-fold. As shown by structure-activity analysis, the length of the linker has a dramatic effect on the toxicity of compounds. Compound 2e with -C12H24- linker exhibited the lowest toxicity (CTD50=2216μM). Derivatives of camphor, therefore, can be considered as prospective antiinfluenza compounds active against influenza viruses resistant to adamantane-based drugs.


Bioorg Med Chem


Sokolova AS,Yarovaya OC,Korchagina DV,Zarubaev VV,Tretiak TS,Anfimov PM,Kiselev OI,Salakhutdinov NF




Has Abstract


2014-04-01 00:00:00














  • QSAR studies of HIV-1 integrase inhibition.

    abstract::Compounds from a wide variety of structural classes inhibit HIV-1 integrase. However, a single unified understanding of the relationship between the structures and activities of these compounds still eludes researchers. We report herein the development of QSAR models for integrase inhibition. The genetic function appr...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Yuan H,Parrill AL

    更新日期:2002-12-01 00:00:00

  • Discovery of pyridine-based agrochemicals by using Intermediate Derivatization Methods.

    abstract::Pyridine-based compounds have been playing a crucial role as agrochemicals or pesticides including fungicides, insecticides/acaricides and herbicides, etc. Since most of the agrochemicals listed in the Pesticide Manual were discovered through screening programs that relied on trial-and-error testing and new agrochemic...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章,评审


    authors: Guan AY,Liu CL,Sun XF,Xie Y,Wang MA

    更新日期:2016-02-01 00:00:00

  • Screening, synthesis, crystal structure, and molecular basis of 6-amino-4-phenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitriles as novel AKR1C3 inhibitors.

    abstract::AKR1C3 is a promising therapeutic target for castration-resistant prostate cancer. Herein, an evaluation of in-house library discovered substituted pyranopyrazole as a novel scaffold for AKR1C3 inhibitors. Preliminary SAR exploration identified its derivative 19d as the most promising compound with an IC50 of 0.160 μM...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Zheng X,Jiang Z,Li X,Zhang C,Li Z,Wu Y,Wang X,Zhang C,Luo HB,Xu J,Wu D

    更新日期:2018-12-01 00:00:00

  • An unusual functional group interaction and its potential to reproduce steric and electrostatic features of the transition states of peptidolysis.

    abstract::The donor-acceptor interaction between a tertiary amine and an aldehyde, first observed among a select class of alkaloids, was deliberately established in a peptidomimetic (1a-c) to mimic features of the two principal transition states of peptide hydrolysis. Compounds 1a-c show preferential adoption in methanol and wa...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Gautier A,Pitrat D,Hasserodt J

    更新日期:2006-06-01 00:00:00

  • Interaction between artemisinin and heme. A Density Functional Theory study of structures and interaction energies.

    abstract::Malaria is an infectious disease caused by the unicellular parasite Plasmodium sp. Currently, the malaria parasite is becoming resistant to the traditional pharmacological alternatives, which are ineffective. Artemisinin is the most recent advance in the chemotherapy of malaria. Since it has been proven that artemisin...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Araújo JQ,Carneiro JW,de Araujo MT,Leite FH,Taranto AG

    更新日期:2008-05-01 00:00:00

  • Synthesis and antimicrobial activity of squalamine analogue.

    abstract::Synthesis and antimicrobial activity of squalamine analogue 2 are reported. The synthesis of 2 was accomplished from bisnoralcohol 3. The spermidine moiety was introduced via reductive amination of an appropriately functionalized 3beta-aminosterol with spermidinyl aldehyde 17 utilizing sodium triacetoxyborohydride as ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Kim HS,Choi BS,Kwon KC,Lee SO,Kwak HJ,Lee CH

    更新日期:2000-08-01 00:00:00

  • Novel dimeric aryldiketo containing inhibitors of HIV-1 integrase: effects of the phenyl substituent and the linker orientation.

    abstract::Aryl diketoacids (ADK) and their bioisosteres are among the most promising HIV-1 integrase (IN) inhibitors. Previously, we designed a series of ADK dimers as a new class of IN inhibitors that were hypothesized to target two divalent metal ions on the active site of IN. Herein we present a further structure-activity re...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Zeng LF,Jiang XH,Sanchez T,Zhang HS,Dayam R,Neamati N,Long YQ

    更新日期:2008-08-15 00:00:00

  • Synthesis and phosphodiesterase 5 inhibitory activity of novel phenyl ring modified sildenafil analogues.

    abstract::New sildenafil analogues containing an ether ring fused into the phenyl moiety, 6a--d and 7a--d, were efficiently synthesized from the readily available starting materials, 1a--d and 2, in five steps. Ab initio calculations indicated that introduction of a cyclic ether to the phenyl group might enhance the co-planarit...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Kim DK,Lee N,Lee JY,Ryu DH,Kim JS,Lee SH,Choi JY,Chang K,Kim YW,Im GJ,Choi WS,Kim TK,Ryu JH,Kim NH,Lee K

    更新日期:2001-06-01 00:00:00

  • A new modification of anti-tubercular active molecules.

    abstract::The connection of two active molecules across an easily released bridge as a new type of potentially active molecule has been studied. The synthesis is based on derivatives that originate from isonicotinoyl hydrazide, pyrazinamide, p-aminosalicylic acid (PAS), ethambutol, and ciprofloxacin. The lipophilicity, hydrolys...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Imramovský A,Polanc S,Vinsová J,Kocevar M,Jampílek J,Recková Z,Kaustová J

    更新日期:2007-04-01 00:00:00

  • Synthesis of brequinar analogue inhibitors of malaria parasite dihydroorotate dehydrogenase.

    abstract::A series of 2-phenyl quinoline-4-carboxylic acid derivatives related to brequinar, an inhibitor of human dihydroorotate dehydrogenase (DHODH), has been prepared and evaluated as inhibitors of DHODH from the malaria parasite Plasmodium falciparum. Brequinar was essentially inactive against PfDHODH (IC(50) 880 microM) w...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Boa AN,Canavan SP,Hirst PR,Ramsey C,Stead AM,McConkey GA

    更新日期:2005-03-15 00:00:00

  • Cloning, characterization and anion inhibition studies of a new γ-carbonic anhydrase from the Antarctic bacterium Pseudoalteromonas haloplanktis.

    abstract::A new γ-class carbonic anhydrase (CA, EC was cloned, purified and characterized from the Antarctic bacterium Pseudoalteromonas haloplanktis, PhaCAγ. The enzyme has a medium-low catalytic activity for the physiologic reaction of CO2 hydration to bicarbonate and protons, with a kcat of 1.4×10(5)s(-1) and a kcat...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: De Luca V,Vullo D,Del Prete S,Carginale V,Scozzafava A,Osman SM,AlOthman Z,Supuran CT,Capasso C

    更新日期:2015-08-01 00:00:00

  • Enhanced RNA binding of dimerized aminoglycosides.

    abstract::Aminoglycoside antibiotics have recently emerged as an intriguing family of RNA binding molecules and they became leading structures for the design of novel RNA ligands. The demystification of the aminoglycoside-RNA recognition phenomenon is required for the development of superior binders. To explore the existence of...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Michael K,Wang H,Tor Y

    更新日期:1999-07-01 00:00:00

  • Antiproliferative and apoptosis-inducing activities of alkyl gallate and gallamide derivatives related to (-)-epigallocatechin gallate.

    abstract::Green tea and (-)-epigallocatechin gallate (EGCG: one of the main components of green tea) are reported to have cancer-preventive activity in humans. A previous SAR study of EGCG and derivatives indicated that a galloyl group is essential for the activity. To test this hypothesis, we synthesized various alkyl gallate ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Dodo K,Minato T,Noguchi-Yachide T,Suganuma M,Hashimoto Y

    更新日期:2008-09-01 00:00:00

  • Pyrrolomycins as antimicrobial agents. Microwave-assisted organic synthesis and insights into their antimicrobial mechanism of action.

    abstract::New compounds able to counteract staphylococcal biofilm formation are needed. In this study we investigate the mechanism of action of pyrrolomycins, whose potential as antimicrobial agents has been demonstrated. We performed a new efficient and easy method to use microwave organic synthesis suitable for obtaining pyrr...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Raimondi MV,Listro R,Cusimano MG,La Franca M,Faddetta T,Gallo G,Schillaci D,Collina S,Leonchiks A,Barone G

    更新日期:2019-03-01 00:00:00

  • Citral derived amides as potent bacterial NorA efflux pump inhibitors.

    abstract::Monoterpene citral and citronellal have been used as starting material for the preparation of 5,9-dimethyl-deca-2,4,8-trienoic acid amides and 9-formyl-5-methyl-deca-2,4,8-trienoic acid amides. The amides on bioevaluation as efflux pump inhibitors (EPIs) against Staphylococcus aureus 1199 and NorA overexpressing S. au...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Thota N,Koul S,Reddy MV,Sangwan PL,Khan IA,Kumar A,Raja AF,Andotra SS,Qazi GN

    更新日期:2008-07-01 00:00:00

  • Synthesis and physical characterization of a P1 arginine combinatorial library, and its application to the determination of the substrate specificity of serine peptidases.

    abstract::Serine peptidases are a large, well-studied, and medically important class of peptidases. Despite the attention these enzymes have received, details concerning the substrate specificity of even some of the best known enzymes in this class are lacking. One approach to rapidly characterizing substrate specificity for pe...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Furlong ST,Mauger RC,Strimpler AM,Liu YP,Morris FX,Edwards PD

    更新日期:2002-11-01 00:00:00

  • Discovery of novel quinoline-based mTOR inhibitors via introducing intra-molecular hydrogen bonding scaffold (iMHBS): The design, synthesis and biological evaluation.

    abstract::A series of quinoline derivatives featuring the novelty of introducing intra-molecular hydrogen bonding scaffold (iMHBS) were designed, synthesized and biologically evaluated for their mTOR inhibitory activity, as well as anti-proliferative efficacies against HCT-116, PC-3 and MCF-7 cell lines. As a result, six compou...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Ma X,Lv X,Qiu N,Yang B,He Q,Hu Y

    更新日期:2015-12-15 00:00:00

  • Antioxidant activity of benzoxazolinonic and benzothiazolinonic derivatives in the LDL oxidation model.

    abstract::A series of benzazolone compounds were synthesized utilizing benzoxazolinonic and benzothiazolinonic heterocycles as the building unit. The antioxidant activity of these compounds was determined by inhibition of lipid peroxidation. The oxidation of LDL was induced in the presence of CuSO(4) or 2,2'-azobis(2-amidinopro...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Yekini I,Hammoudi F,Martin-Nizard F,Yous S,Lebegue N,Berthelot P,Carato P

    更新日期:2009-11-15 00:00:00

  • Synthesis and methemoglobinemia-inducing properties of benzocaine isosteres designed as humane rodenticides.

    abstract::A number of isosteres (oxadiazoles, thiadiazoles, tetrazoles and diazines) of benzocaine were prepared and evaluated for their capacity to induce methemoglobinemia-with a view to their possible application as humane pest control agents. It was found that an optimal lipophilicity for the formation of methemoglobin (met...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Conole D,Beck TM,Jay-Smith M,Tingle MD,Eason CT,Brimble MA,Rennison D

    更新日期:2014-04-01 00:00:00

  • Benzimidazole inhibitors from the Niclosamide chemotype inhibit Wnt/β-catenin signaling with selectivity over effects on ATP homeostasis.

    abstract::The Wnt signaling pathway plays a key role in organ and tissue homeostasis, and when dysregulated, can become a major underlying mechanism of disease, particularly cancer. We reported previously that the anthelmintic drug Niclosamide inhibits Wnt/β-catenin signaling and suppresses colon cancer cell growth in vitro and...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Mook RA Jr,Ren XR,Wang J,Piao H,Barak LS,Kim Lyerly H,Chen W

    更新日期:2017-03-15 00:00:00

  • Ratiometric nanoprobe for circulating tumor cell detection and intracellular hydrogen peroxide evaluation in colorectal cancer patients.

    abstract::The application of intensity-based H2O2-responsive fluorescence nanoprobe for circulating tumor cell detection was limited by the complex background and the nanoprobe uptake in each CTC. In this context, we developed a ratiometric fluorescence nanoprobe, on which a H2O2-responsive subunit and a stable subunit grafted ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Pan R,Lu X,Ju J,Guan Q,Su Y,Li C,Li P

    更新日期:2021-01-15 00:00:00

  • Bisquaternary caracurine V and iso-caracurine V salts as ligands for the muscle type of nicotinic acetylcholine receptors: SAR and QSAR studies.

    abstract::The binding constants (K(i) values) of 24 caracurine V and 6 iso-caracurine V analogues for the muscle type of nicotinic ACh receptors (nAChR) from Torpedo californica were determined in a binding assay using (+/-)-[(3)H]epibatidine as a radioligand. The allyl alcohol group present in the iso-caracurine V ring system ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Zlotos DP,Gündisch D,Ferraro S,Tilotta MC,Stiefl N,Baumann K

    更新日期:2004-12-01 00:00:00

  • Design, synthesis, and docking studies of quinazoline analogues bearing aryl semicarbazone scaffolds as potent EGFR inhibitors.

    abstract::Two series of quinazoline derivatives bearing aryl semicarbazone scaffolds (9a-o and 10a-o) were designed, synthesized and evaluated for the IC50 values against four cancer cell lines (A549, HepG2, MCF-7 and PC-3). The selected compound 9o was further evaluated for the inhibitory activity against EGFR kinases. Four of...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Tu Y,Wang C,Xu S,Lan Z,Li W,Han J,Zhou Y,Zheng P,Zhu W

    更新日期:2017-06-15 00:00:00

  • Efficient sequential synthesis of PET Probes of the COX-2 inhibitor [11C]celecoxib and its major metabolite [11C]SC-62807 and in vivo PET evaluation.

    abstract::Synthesis of [(11)C]celecoxib, a selective COX-2 inhibitor, and [(11)C]SC-62807, a major metabolite of celecoxib, were achieved and the potential of these PET probes for assessing the function of drug transporter in biliary excretion was evaluated. The synthesis of [(11)C]celecoxib was achieved in one-pot by reacting ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Takashima-Hirano M,Takashima T,Katayama Y,Wada Y,Sugiyama Y,Watanabe Y,Doi H,Suzuki M

    更新日期:2011-05-01 00:00:00

  • Oligomers of glycamino acid.

    abstract::Glycamino acids, a family of sugar amino acids, are derivatives of C-glycosides that possesses a carboxyl group at the C-1 position and an amino group replacing one of the hydroxyl groups at either the C-2, 3, 4, or 6 position. We have prepared a series of glucose-type glycamino acids as monomeric building blocks: the...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Suhara Y,Yamaguchi Y,Collins B,Schnaar RL,Yanagishita M,Hildreth JE,Shimada I,Ichikawa Y

    更新日期:2002-06-01 00:00:00

  • In vitro evaluation of the anti-estrogenic activity of hydroxyl substituted diphenylnaphthyl alkene ligands for the estrogen receptor.

    abstract::There is still a need for additional scaffolds to further explore tissue selectivity and improving efficacy of selective estrogen receptor modulators (SERMs). A series of hydroxyl substituted diphenylnaphthyl alkene ligands for the two estrogen receptors are described that arose from an initial de novo designed diphen...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Schmidt JM,Tremblay GB,Plastina MA,Ma F,Bhal neé Basra S,Feher M,Dunn-Dufault R,Redden PR

    更新日期:2005-03-01 00:00:00

  • Quinazolindione derivatives as potent 5-HT3A receptor antagonists.

    abstract::5-HT(3A) receptor antagonists have been used mainly for the treatment of nausea and vomiting. These days, the antagonists are of special interest due to their therapeutic potential to treat other diseases such as depression, psychotic disorder, drug abuse, and irritable bowel syndrome. To discover novel 5-HT(3A) recep...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Lee BH,Choi MJ,Jo MN,Seo HJ,Nah SY,Cho YS,Nam G,Pae AN,Rhim H,Choo H

    更新日期:2009-07-01 00:00:00

  • Design, synthesis, and biological evaluation of 1,3-diarylprop-2-en-1-ones : a novel class of cyclooxygenase-2 inhibitors.

    abstract::A group of regioisomeric (E)-1,3-diarylprop-2-en-1-one derivatives possessing a COX-2 SO2Me pharmacophore at the para position of the C-1 or C-3 phenyl ring, in conjunction with a C-3 or C-1 phenyl (4-H) or substituted-phenyl ring (4-F, 4-OMe and 4-Me), were designed for evaluation as selective cyclooxygenase-2 (COX-2...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Zarghi A,Arfaee S,Rao PN,Knaus EE

    更新日期:2006-04-15 00:00:00

  • Photolabile ubiquinone analogues for identification and characterization of quinone binding sites in proteins.

    abstract::Quinones are essential components in most cell and organelle bioenergetic processes both for direct electron and/or proton transfer reactions but also as means to regulate various bioenergetic processes by sensing cell redox states. To understand how quinones interact with proteins, it is important to have tools for i...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Pei Z,Gustavsson T,Roth R,Frejd T,Hägerhäll C

    更新日期:2010-05-15 00:00:00

  • Synthesis of the (1→6)-linked thiodisaccharide of galactofuranose: inhibitory activity against a β-galactofuranosidase.

    abstract::A new (1→6)-linked thiodisaccharide formed by two galactofuranosyl units has been synthesized. Methyl (methyl α,β-D-galactofuranosid)uronate was employed as the starting compound, which was per-O-silylated with TBSCl and reduced with LiAlH4 to afford methyl 2,3,5-tri-O-tert-butyldimethylsilyl-β-D-galactofuranoside (2β...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Repetto E,Marino C,Varela O

    更新日期:2013-06-01 00:00:00