3-Phenylalkyl-2H-chromenes and -chromans as novel rhinovirus infection inhibitors.


:Following our studies on structure-activity relationships of anti-rhinovirus chromene and chroman derivatives, we designed and synthesized new series of 3-phenylalkyl-2H-chromenes and -chromans bearing differently sized, aliphatic linker chains between the two cycles. The cytotoxicity and the antiviral activity of the new compounds on human rhinovirus (HRV) serotype 1B and 14 infection were evaluated in HeLa cell cultures. Most of the tested compounds interfered with HRV1B multiplication in the micromolar or submicromolar concentrations while HRV14 was less susceptible. 3-[3-(4-Chlorophenyl)propyl]chroman (9c) was selected for preliminary mechanism of action studies due to its potent activity against both serotypes (IC50 of 0.48μM and 1.36μM towards HRV1B and 14, respectively) coupled with high selectivity (SI=206.18 and 73.26, respectively). Results of time of addition/removal studies suggest that 9c, similarly to related derivatives, behaves as a capsid binder interfering with some early events of the HRV1B infectious cycle.


Bioorg Med Chem


Conti C,Proietti Monaco L,Desideri N




Has Abstract


2017-04-01 00:00:00














  • Structure-activity study of epi-gallocatechin gallate (EGCG) analogs as proteasome inhibitors.

    abstract::The structure-activity relationship of a number of synthetic green tea polyphenol analogs involving modifications of A ring and B ring of epi-gallocatechin gallate (EGCG) as proteasome inhibitors has been examined. It was found that in B ring, a decrease in the number of OH groups led to decreased potency. Introductio...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Wan SB,Landis-Piwowar KR,Kuhn DJ,Chen D,Dou QP,Chan TH

    更新日期:2005-03-15 00:00:00

  • Recent progresses on synthesized LuxS inhibitors: A mini-review.

    abstract::Design and synthesis of LuxS enzyme inhibitors otherwise known as S-ribosylhomocysteine analogues, to target quorum sensing in bacteria, has been considerably developed within the last decade. This review presents which molecules have been synthesized to target LuxS enzyme in other words inhibitors of S-ribosylhomocys...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章,评审


    authors: Mina G,Chbib C

    更新日期:2019-01-01 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

  • Synthesis and antitrichinellosis activity of some 2-substituted-[1,3]thiazolo[3,2-a]benzimidazol-3(2H)-ones.

    abstract::Some new thiazolo[3,2-a]benzimidazolone derivatives were synthesized using two methods. The structures of the synthesized compounds were proved by means of IR, (1)H NMR and mass spectral data. Ab initio computations were performed in order to determine the electronic structure and geometry of the investigated molecule...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Mavrova ATs,Anichina KK,Vuchev DI,Tsenov JA,Kondeva MS,Micheva MK

    更新日期:2005-10-01 00:00:00

  • Generation of hazardous methyl azide and its application to synthesis of a key-intermediate of picarbutrazox, a new potent pesticide in flow.

    abstract::Generation and reactions of methyl azide (MeN3) were successfully performed by using a flow reactor system, demonstrating that the flow method serves as a safe method for handling hazardous explosive methyl azide. The reaction of NaN3 and Me2SO4 in a flow reactor gave a MeN3 solution, which was used for Huisgen reacti...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Ichinari D,Nagaki A,Yoshida JI

    更新日期:2017-12-01 00:00:00

  • Synthesis and photodynamic activity of zinc(II) phthalocyanine derivatives bearing methoxy and trifluoromethylbenzyloxy substituents in homogeneous and biological media.

    abstract::Two zinc(II) phthalocyanines bearing either four methoxy (ZnPc 3) or trifluoromethylbenzyloxy (ZnPc 4) substituents have been synthesized by a two-step procedure starting from 4-nitrophthalonitrile. Absorption and fluorescence spectroscopic studies were analyzed in different media. These compounds are essentially non-...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Yslas EI,Rivarola V,Durantini EN

    更新日期:2005-01-03 00:00:00

  • 3-Phenyl substituted 6,7-dimethoxyisoquinoline derivatives as FtsZ-targeting antibacterial agents.

    abstract::The emergence of multidrug-resistant bacteria has created an urgent need for antibiotics with a novel mechanism of action. The bacterial cell division protein FtsZ is an attractive target for the development of novel antibiotics. The benzo[c]phenanthridinium sanguinarine and the dibenzo[a,g]quinolizin-7-ium berberine ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Kelley C,Zhang Y,Parhi A,Kaul M,Pilch DS,LaVoie EJ

    更新日期:2012-12-15 00:00:00

  • Electronic effects of para-substitution on acetophenones in the reaction of rat liver 3alpha-hydroxysteroid dehydrogenase.

    abstract::Stereoselective reductive metabolism of various p-substituted acetophenone derivatives was studied using isolated rat liver 3alpha-hydroxysteroid dehydrogenase (3alpha-HSD). Kinetic experiments were performed and analyzed by measuring the products by HPLC using a chiral column. The results demonstrated that the presen...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Uwai K,Konno N,Yasuta Y,Takeshita M

    更新日期:2008-02-01 00:00:00

  • pH-dependent production of himeic acid A and its non-enzymatic conversions to himeic acids B and C.

    abstract::The fungus Aspergillus japonicus MF275 produces himeic acid A (1), containing a 4-pyrone ring, along with its congeners, himeic acids B (2) and C (3). During culture, 1 was gradually converted to 3, the corresponding 4-pyridone derivative. A study of the relationship between the culture pH and the fungal metabolites s...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Katsuki A,Kato H,Tahara Y,Hashimoto M,Fujii I,Tsukamoto S

    更新日期:2018-05-01 00:00:00

  • Probing linker design in citric acid-ciprofloxacin conjugates.

    abstract::A series of structurally related citric acid-ciprofloxacin conjugates was synthesised to investigate the influence of the linker between citric acid and ciprofloxacin on antibacterial activities. Minimum inhibitory concentrations (MICs) were determined against a panel of reference strains and clinical isolates of bact...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Milner SJ,Snelling AM,Kerr KG,Abd-El-Aziz A,Thomas GH,Hubbard RE,Routledge A,Duhme-Klair AK

    更新日期:2014-08-15 00:00:00

  • Synthesis of 2-amido-3-hydroxypyridin-4(1H)-ones: novel iron chelators with enhanced pFe3+ values.

    abstract::The synthesis of a range of 2-amido-3-hydroxypyridin-4-ones as bidentate iron(III) chelators with potential for oral administration is described. The pKa values of the ligands together with the stability constants of their iron(III) complexes have been determined. Results indicate that the introduction of an amido sub...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Liu ZD,Piyamongkol S,Liu DY,Khodr HH,Lu SL,Hider RC

    更新日期:2001-03-01 00:00:00

  • The use of a conformational cathepsin D-derived epitope for vaccine development against Schistosoma mansoni.

    abstract::Schistosomiasis is caused by the infection from Schistosoma species. Among these, Schistosoma mansoni is one of the major species that infects millions of people worldwide. The use of praziquantel is effective in clearing the infestation but treatment of a large and widespread population in endemic areas is unsustaina...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Ahmad Fuaad AA,Roubille R,Pearson MS,Pickering DA,Loukas AC,Skwarczynski M,Toth I

    更新日期:2015-03-15 00:00:00

  • 2- and 3-substituted imidazo[1,2-a]pyrazines as inhibitors of bacterial type IV secretion.

    abstract::A novel series of 8-amino imidazo[1,2-a]pyrazine derivatives has been developed as inhibitors of the VirB11 ATPase HP0525, a key component of the bacterial type IV secretion system. A flexible synthetic route to both 2- and 3-aryl substituted regioisomers has been developed. The resulting series of imidazo[1,2-a]pyraz...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Sayer JR,Walldén K,Pesnot T,Campbell F,Gane PJ,Simone M,Koss H,Buelens F,Boyle TP,Selwood DL,Waksman G,Tabor AB

    更新日期:2014-11-15 00:00:00

  • Synthesis and anticonvulsant activity of new N-Mannich bases derived from 3-(2-fluorophenyl)- and 3-(2-bromophenyl)-pyrrolidine-2,5-diones. Part II.

    abstract::Synthesis and anticonvulsant activity of new N-Mannich bases of 3-(2-fluorophenyl)- and 3-(2-bromophenyl)-pyrrolidine-2,5-diones have been described. Initial anticonvulsant screening was performed in mice after intraperitoneal administration in the maximal electroshock seizure test (MES) and subcutaneous pentylenetetr...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Obniska J,Rzepka S,Kamiński K

    更新日期:2012-08-01 00:00:00

  • Phenylhydrazides as inhibitors of Leishmania amazonensis arginase and antileishmanial activity.

    abstract::Searching for new substances with antileishmanial activity, we synthesized and evaluated a series of α,α-difluorohydrazide and α,α-difluoramides against Leishmania amazonensis arginase (LaArg). Four α,α-difluorohydrazide derivatives showed activity against LaArg with Ki in the range of 1.3-26 μM. The study of the kine...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Crizanto de Lima E,Castelo-Branco FS,Maquiaveli CC,Farias AB,Rennó MN,Boechat N,Silva ER

    更新日期:2019-09-01 00:00:00

  • Arylazolyl(azinyl)thioacetanilides. Part 16: Structure-based bioisosterism design, synthesis and biological evaluation of novel pyrimidinylthioacetanilides as potent HIV-1 inhibitors.

    abstract::A series of novel pyrimidinylthioacetanilides were designed, synthesized, and evaluated for their biological activity as potent HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs). Most of the tested compounds were proved to be effective in inhibiting HIV-1 (IIIB) replication with EC50 ranging from 0.15 μM ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Li X,Lu X,Chen W,Liu H,Zhan P,Pannecouque C,Balzarini J,De Clercq E,Liu X

    更新日期:2014-10-01 00:00:00

  • Synthesis and evaluation of 11β-(4-substituted phenyl) estradiol analogs: transition from estrogen receptor agonists to antagonists.

    abstract:INTRODUCTION:As part of our program to develop estrogen receptor (ER) targeted imaging and therapeutic agents we chose to evaluate 11β-substituted estradiol analogs as a representative scaffold. Previous synthetic studies provided an entry into this class of compounds and other work indicated that 11β-(substituted aryl...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Hanson RN,Hua E,Hendricks JA,Labaree D,Hochberg RB

    更新日期:2012-06-15 00:00:00

  • Synthesis of pdCpAs and transfer RNAs activated with thiothreonine and derivatives.

    abstract::N,S-diprotected L-thiothreonine and L-allo-thiothreonine derivatives were synthesized using a novel chemical strategy, and used for esterification of the dinucleotide pdCpA. The aminoacylated dinucleotides were then employed for the preparation of activated suppressor tRNA(CUA) transcripts. Thiothreonine and allo-thio...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Chen S,Fahmi NE,Nangreave RC,Mehellou Y,Hecht SM

    更新日期:2012-04-15 00:00:00

  • Synthesis of 3-acyloxyxanthone derivatives as α-glucosidase inhibitors: A further insight into the 3-substituents' effect.

    abstract::Considerable interest has been attracted in xanthone and its derivatives because of their important biological activities. In this paper, a series of novel 3-arylacyloxyxanthone derivatives 2a-p were synthesized and evaluated for their biological activities toward α-glucosidase. In comparison to the parent 1,3-dihydro...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Li GL,Cai CY,He JY,Rao L,Ma L,Liu Y,Wang B

    更新日期:2016-04-01 00:00:00

  • Design, synthesis and biological activity of phenoxyacetic acid derivatives as novel free fatty acid receptor 1 agonists.

    abstract::The free fatty acid receptor 1 (FFA1) is a novel antidiabetic target for the treatment of type 2 diabetes based on particular mechanism in amplifying glucose-stimulated insulin secretion. We have previously identified a series of phenoxyacetic acid derivatives. Herein, we describe the further chemical modification of ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Li Z,Wang X,Xu X,Yang J,Xia W,Zhou X,Huang W,Qian H

    更新日期:2015-11-15 00:00:00

  • Nicorandil analogues containing NO-donor furoxans and related furazans.

    abstract::The synthesis and in vitro vasodilating properties of hybrid compounds in which furoxan (1,2,5-oxadiazole 2-oxide) moieties, endowed with different NO-donor properties, were substituted for the nitroxy function of Nicorandil are reported. The corresponding cyanoguanidine analogues are also considered. This approach ha...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Boschi D,Cena C,Di Stilo A,Fruttero R,Gasco A

    更新日期:2000-07-01 00:00:00

  • Mechanism of influence of phosphorylation on serine 124 on a decrease of catalytic activity of human thymidylate synthase.

    abstract::Regulation by phosphorylation is a well-established mechanism for controlling biological activity of proteins. Recently, phosphorylation of serine 124 in human thymidylate synthase (hTS) has been shown to lower the catalytic activity of the enzyme. To clarify a possible mechanism of the observed influence, molecular d...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Jarmuła A,Fraczyk T,Cieplak P,Rode W

    更新日期:2010-05-15 00:00:00

  • Synthesis and trypanocidal activity of ent-kaurane glycosides.

    abstract::Novel ent-kaurane glucosides were synthezised by a Koenigs-Knorr reaction between C17 and C19 alcohols derived from kaurenoic acid and 2,3,4,6-tetra-O-acetyl-glucopyranosyl bromide, followed by the hydrolysis of the acetates. Main products were assayed in vitro and in vivo against blood trypomastigote forms of Trypano...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Batista R,Humberto JL,Chiari E,de Oliveira AB

    更新日期:2007-01-01 00:00:00

  • New mimics of the acetate function in pheromone-based attraction.

    abstract::Several analogues of (Z)-8-dodecenyl acetate (1a), the major pheromone component of the Oriental fruit moth, Cydia molesta, with chloroformate and lactone functional groups in place of the acetate moiety, were synthesized and investigated for their biological activity at four evaluation levels, i.e. by electroantennog...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Hoskovec M,Hovorka O,Kalinová B,Koutek B,Streinz L,Svatos A,Sebek P,Saman D,Vrkoc J

    更新日期:1996-03-01 00:00:00

  • Structural-activity relationship study of highly-functionalized imidazolines as potent inhibitors of nuclear transcription factor-kappaB mediated IL-6 production.

    abstract::We herein describe the synthesis and anti-inflammatory properties of a small library of imidazoline-based NF-kappaB inhibitors. The structure-activity relationship of various substituents on an imidazoline core structure was evaluated for the ability to inhibit NF-kappaB mediated IL-6 production. Optimization of the s...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Kahlon DK,Lansdell TA,Fisk JS,Tepe JJ

    更新日期:2009-04-15 00:00:00

  • Alkyne derivatives of isocoumarins as clickable activity-based probes for serine proteases.

    abstract::Activity-based probes (ABPs) have found increasing use in functional proteomics studies. Recently, ABPs that can be employed in combination with click chemistry gained particular attention due to their flexible application in vitro and in vivo. Moreover, there is a continuous need for new ABPs that target small subset...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Haedke U,Götz M,Baer P,Verhelst SH

    更新日期:2012-01-15 00:00:00

  • Nucleotide analogues containing 2-oxa-bicyclo[2.2.1]heptane and l-alpha-threofuranosyl ring systems: interactions with P2Y receptors.

    abstract::The ribose moiety of adenine nucleotide 3',5'-bisphosphate antagonists of the P2Y(1) receptor has been successfully substituted with a rigid methanocarba ring system, leading to the conclusion that the North (N) ring conformation is preferred in receptor binding. Similarly, at P2Y(2) and P2Y(4) receptors, nucleotides ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Ohno M,Costanzi S,Kim HS,Kempeneers V,Vastmans K,Herdewijn P,Maddileti S,Gao ZG,Harden TK,Jacobson KA

    更新日期:2004-11-01 00:00:00

  • Synthesis, structural characterization and cell death-inducing effect of novel palladium(II) and platinum(II) saccharinate complexes with 2-(hydroxymethyl)pyridine and 2-(2-hydroxyethyl)pyridine on cancer cells in vitro.

    abstract::Four palladium(II) and platinum(II) saccharinate (sac) complexes with 2-(hydroxymethyl)pyridine (2-hmpy) and 2-(2-hydroxyethyl)pyridine (2-hepy), namely trans-[Pd(2-hmpy)2(sac)2]·H2O (1), trans-[Pt(2-hmpy)2(sac)2]·3H2O (2), trans-[Pd(2-hepy)2(sac)2] (3) and trans-[Pt(2-hepy)2(sac)2] (4), have been synthesized and char...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Ari F,Aztopal N,Icsel C,Yilmaz VT,Guney E,Buyukgungor O,Ulukaya E

    更新日期:2013-11-01 00:00:00

  • Synthesis of curcumin mimics with multidrug resistance reversal activities.

    abstract::In order to discover novel multidrug resistance (MDR) reversal agents for efficient cancer chemotherapy, the unsymmetrical curcumin mimics with various amide moieties (6-19) were synthesized and evaluated their MDR reversal activities in MDR cell line KBV20C. Among the tested compounds, 13, 16, and 17 showed potent MD...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Um Y,Cho S,Woo HB,Kim YK,Kim H,Ham J,Kim SN,Ahn CM,Lee S

    更新日期:2008-04-01 00:00:00

  • Novel chromogenic aminopeptidase substrates for the detection and identification of clinically important microorganisms.

    abstract::A series of amino acid derivatives 8-10, 42 and 43 have been prepared as chromogenic enzyme substrates in order to detect aminopeptidase activity in clinically important Gram-negative and Gram-positive bacteria. Enzymatic hydrolysis liberates the amino acid moiety and either a 4-aminophenol or a 4-dialkylaminoaniline ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Cellier M,James AL,Orenga S,Perry JD,Rasul AK,Robinson SN,Stanforth SP

    更新日期:2014-10-01 00:00:00