QSAR for non-nucleoside inhibitors of HIV-1 reverse transcriptase.


:By means of QSAR algorithms we model the potency pIC(90) [mM] of 154 non-nucleoside reverse transcriptase inhibitors (NNRTI) of the wild-type HIV-1 virus, considered as the second generation analogues of Efavirenz. In addition, 56 inhibitors of the K-103N viral mutant form are also investigated. A pool of 1494 theoretical molecular descriptors provided mainly by the Dragon 5 software is explored by several methods of variable selection: forward stepwise regression, the replacement method, and the genetic algorithm approach. The optimal models found include up to seven parameters: R = 0.7991, R(l-20%-o) = 0.7233 for the case of wild-type, and R = 0.9261, R(l-5%-o) = 0.8802 for the K-103N mutation.


Bioorg Med Chem


Duchowicz PR,Fernández M,Caballero J,Castro EA,Fernández FM




Has Abstract


2006-09-01 00:00:00














  • Fine tuning of agonistic/antagonistic activity for vitamin D receptor by 22-alkyl chain length of ligands: 22S-Hexyl compound unexpectedly restored agonistic activity.

    abstract::1α,25-Dihydroxyvitamin D3 exerts its actions by binding to vitamin D receptor (VDR). We are continuing the study related to the alteration of pocket structure of VDR by 22-alkyl substituent of ligands and the relationships between the alteration and agonistic/antagonistic activity. Previously we reported that compound...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Anami Y,Sakamaki Y,Itoh T,Inaba Y,Nakabayashi M,Ikura T,Ito N,Yamamoto K

    更新日期:2015-11-15 00:00:00

  • SAR of a series of anti-HSV-1 acridone derivatives, and a rational acridone-based design of a new anti-HSV-1 3H-benzo[b]pyrazolo[3,4-h]-1,6-naphthyridine series.

    abstract::Herpes Simplex Virus (HSV) infections are among the most common human diseases. In this work, we assess the structural features and electronic properties of a series of ten 1-hydroxyacridone derivatives (1a-j) recently described as a new class of non-nucleoside inhibitors of Herpes Simplex Virus-1 (HSV-1). Based on th...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Bernardino AM,Castro HC,Frugulhetti IC,Loureiro NI,Azevedo AR,Pinheiro LC,Souza TM,Giongo V,Passamani F,Magalhães UO,Albuquerque MG,Cabral LM,Rodrigues CR

    更新日期:2008-01-01 00:00:00

  • Effect of prime-site sequence of retro-inverso-modified HTLV-1 protease inhibitor.

    abstract::The effects of additional substituents covering the prime-site of retro-inverso (RI)-modified HTLV-1 protease inhibitors containing a hydroxyethylamine isoster were clarified. Stereo-selective construction of the most potent isoster backbone was achieved by the Evans-aldol reaction. Addition of N-acetylated d-amino ac...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Awahara C,Tatsumi T,Furuta S,Shinjoh G,Konno H,Nosaka K,Kobayashi K,Hattori Y,Akaji K

    更新日期:2014-04-15 00:00:00

  • 000Synthesis of new α-aminophosphonates: Evaluation as anti-inflammatory agents and QSAR studies.

    abstract::In this paper, we report the synthesis of a new series of α-aminophosphonates derivatives based in an efficient three-component reaction. All compounds prepared showed significant anti-inflammatory activity, being the compounds 1a, 1c, 1d, 1f, 2b and 2c the most promising ones, in terms of maximal efficacy (over 95%),...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Romero-Estudillo I,Viveros-Ceballos JL,Cazares-Carreño O,González-Morales A,de Jesús BF,López-Castillo M,Razo-Hernández RS,Castañeda-Corral G,Ordóñez M

    更新日期:2019-06-15 00:00:00

  • Hantzsch 1,4-dihydropyridines containing a diazen-1-ium-1,2-diolate nitric oxide donor moiety to study calcium channel antagonist structure-activity relationships and nitric oxide release.

    abstract::A group of racemic 3-isopropyl 5-[(2-piperazin-1-yl)ethyl] 1,4-dihydro-2,6-dimethyl-4-(pyridyl)-3,5-pyridinedicarboxylates (12a-c), 3-isopropyl 5-{2-[4-nitrosopiperazinyl]ethyl} 1,4-dihydro-2,6-dimethyl-4-(pyridyl)-3,5-pyridinedicarboxylates (14a-c) and 3-isopropyl 5-{2-[(O(2)-acetoxymethyldiazen-1-ium-1,2-diolate)(N,...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Nguyen JT,Velázquez CA,Knaus EE

    更新日期:2005-03-01 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

  • Comparison of the anti-influenza virus activity of cyclopentane derivatives with oseltamivir and zanamivir in vivo.

    abstract::Cyclopentane derivatives, designated as BCX-1812, BCX-1827, BCX-1898, and BCX-1923, were tested in parallel with oseltamivir carboxylate and zanamivir for the in vivo activity in mice infected with A/Turkey/Mas/76 X A/Beijing/32/92 (H6N2) influenza virus. The compounds were tested orally and intranasally at different ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Chand P,Bantia S,Kotian PL,El-Kattan Y,Lin TH,Babu YS

    更新日期:2005-06-02 00:00:00

  • In silico directed chemical probing of the adenosine receptor family.

    abstract::One of the grand challenges in chemical biology is identifying a small-molecule modulator for each individual function of all human proteins. Instead of targeting one protein at a time, an efficient approach to address this challenge is to target entire protein families by taking advantage of the relatively high level...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Areias FM,Brea J,Gregori-Puigjané E,Zaki ME,Carvalho MA,Domínguez E,Gutiérrez-de-Terán H,Proença MF,Loza MI,Mestres J

    更新日期:2010-05-01 00:00:00

  • Development of a purine-scaffold novel class of Hsp90 binders that inhibit the proliferation of cancer cells and induce the degradation of Her2 tyrosine kinase.

    abstract::The first published synthesis and characterization of a purine-scaffold library of hsp90 inhibitors is presented. The purine-scaffold represents a platform for the creation of easily synthesizable and derivatizable soluble molecules that are amenable for oral administration. The most active compound of the series (71)...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Chiosis G,Lucas B,Shtil A,Huezo H,Rosen N

    更新日期:2002-11-01 00:00:00

  • Discovery of 1H-benzo[d][1,2,3]triazol-1-yl 3,4,5-trimethoxybenzoate as a potential antiproliferative agent by inhibiting histone deacetylase.

    abstract::Twenty-one benzotriazoles (3-16 and 18-24) were synthesized and half of them (5, 8-16, 20, and 21) were reported for the first time. Their antiproliferative activities against three human cancer cells were assayed. It revealed that 1H-benzo[d][1,2,3]triazol-1-yl 3,4,5-trimethoxybenzoate (9) showed considerable activit...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Fu J,Yang Y,Zhang XW,Mao WJ,Zhang ZM,Zhu HL

    更新日期:2010-12-15 00:00:00

  • The 2'-caged-tethered-siRNA shows light-dependent temporal controlled RNAi activity for GFP gene into HEK293T cells.

    abstract::Small interfering RNA (siRNA) exhibits gene-specific RNAi activity by the formation of RISC complex with mRNA of gene. The structural modification of siRNA at appropriate positions affects the structure of RISC complex and then RNAi activity. The modified siRNA are mostly prepared from the incorporation of sugar ring ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Bollu A,Hassan MK,Dixit M,Sharma NK

    更新日期:2021-01-15 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

  • Trypanocidal activity of new 1,6-diphenyl-1H-pyrazolo[3,4-b]pyridine derivatives: Synthesis, in vitro and in vivo studies.

    abstract::Despite the serious public health problems caused by Chagas disease in several countries, the available therapy remains with only two drugs that are poorly active during the chronic phase of the disease in addition to having severe side effects. In search of new trypanocidal agents, herein we describe the synthesis an...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Ribeiro JLS,Soares JCAV,Portapilla GB,Providello MV,Lima CHS,Muri EMF,de Albuquerque S,Dias LRS

    更新日期:2021-01-01 00:00:00

  • Studies on anti-HIV quinolones: new insights on the C-6 position.

    abstract::The 6-desfluoroquinolones which have been developed by our group represent a promising class of compounds for the treatment of HIV infection since they act on transcriptional regulation, a crucial step in the replication cycle that has not been clinically exploited, yet. Focussing attention on the N-1 and C-6 position...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Massari S,Daelemans D,Manfroni G,Sabatini S,Tabarrini O,Pannecouque C,Cecchetti V

    更新日期:2009-01-15 00:00:00

  • Synthesis and preliminary in vivo evaluation of new [18F]fluoro-inositols as Positron Emission Tomography radiotracers.

    abstract::This study describes the synthesis and radiosynthesis of eight new [18F]fluoro-inositol-based radiotracers in myo- and scyllo-inositol configuration. These radiotracers are equipped with a propyl linker bearing fluorine-18. This fluorinated arm is either on a hydroxyl group, i.e. O-alkylated inositols, or on the cyclo...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Collet C,Schmitt S,Maskali F,Clément A,Chrétien F,Karcher G,Marie PY,Poussier S,Lamandé-Langle S

    更新日期:2017-10-15 00:00:00

  • Synthesis, antitumor activity and structure-activity studies of novel pyridoxine-based bioisosteric analogs of estradiol.

    abstract::A new efficient approach to the synthesis of 6-alkenyl substituted pyridoxine derivatives has been developed. A series of 31 novel alkenyl pyridoxine derivatives, stilbene-based bioisosteric analogs of estradiol, were synthesized. In vitro cytotoxicity of the obtained compounds against MCF-7 (ER+) breast cancer tumor ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Pugachev MV,Pavelyev RS,Nguyen TNT,Gabbasova RR,Bulatov TM,Iksanova AG,Aljondi B,Bondar OV,Grishaev DY,Yamaleeva ZR,Kataeva ON,Nikishova TV,Balakin KV,Shtyrlin YG

    更新日期:2021-01-15 00:00:00

  • 3- and 6-Substituted 2-amino-4,5,6,7-tetrahydrothieno[2,3-c]pyridines as A1 adenosine receptor allosteric modulators and antagonists.

    abstract::A series of 2-amino-4,5,6,7-tetrahydrothieno[2,3-c]pyridines were prepared and evaluated as potential allosteric modulators at the A(1) adenosine receptor. The structure-activity relationships of the 3- and 6-positions of a series of 2-amino-4,5,6,7-tetrahydrothieno[2,3-c]pyridines were explored. Despite finding that ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Aurelio L,Valant C,Figler H,Flynn BL,Linden J,Sexton PM,Christopoulos A,Scammells PJ

    更新日期:2009-10-15 00:00:00

  • The square conformation of phenylglycine-incorporated ascidiacyclamide is stabilized by CH/π interactions between amino acid side chains.

    abstract::We designed a phenylglycine (Phg)-incorporated ascidiacyclamide (ASC) analogue, cyclo(-Phg-oxazoline-d-Val-thiazole-Ile-oxazoline-d-Val-thiazole- ([Phg]ASC), with the aim of stabilizing the square conformation of ASC through interactions between amino acid side chains. X-ray diffraction analysis showed that [Phg]ASC h...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Asano A,Yamada T,Doi M

    更新日期:2011-06-01 00:00:00

  • 2-Amino diphenylsulfides as inhibitors of trypanothione reductase: modification of the side chain.

    abstract::A molecular modeling study meant to detect pharmacophore-like patterns in the active site of trypanothione reductase (TR) offered hints about the opportunity of synthesizing and testing diphenylsulfide derivatives with prolonged or branched polyamino side chains as putative TR inhibitors. The inhibition results within...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Baillet S,Buisine E,Horvath D,Maes L,Bonnet B,Sergheraert C

    更新日期:1996-06-01 00:00:00

  • Synthesis of a tetracyclic, conformationally constrained analogue of delta8-THC.

    abstract::A tetracyclic, conformationally constrained analogue of delta8-THC (2) has been synthesized in which a two carbon bridge exists between C2 and C2'. Two conceptually related syntheses of 2 are described, both of which employ 5,7-dimethoxy-4-oxo-1,2,3,4-tetrahydronaphthoic acid (11) as starting material. This substrate ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Huffman JW,Yu S

    更新日期:1998-12-01 00:00:00

  • Borrelidins F-I, cytotoxic and cell migration inhibiting agents from mangrove-derived Streptomyces rochei SCSIO ZJ89.

    abstract::Borrelidin A (1) is produced by several species of Streptomyces and within its bioactive scaffold, the vinylic nitrile moiety is essential for activity. We report herein newly discovered members of the borrelidin family, borrelidin F (2), borrelidin G (3), borrelidin H (4) and borrelidin I (5); all were isolated from ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Sun J,Shao J,Sun C,Song Y,Li Q,Lu L,Hu Y,Gui C,Zhang H,Ju J

    更新日期:2018-05-01 00:00:00

  • An altered zinc-binding site confers resistance to a covalent inactivator of New Delhi metallo-beta-lactamase-1 (NDM-1) discovered by high-throughput screening.

    abstract::Due to the global threat of antibiotic resistance mediated by New Delhi metallo-beta-lactamase-1 (NDM-1) and the lack of structurally diverse inhibitors reported for this enzyme, we developed screening and counter-screening assays for manual and automated formats. The manual assay is a trans-well absorbance-based endp...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Thomas PW,Spicer T,Cammarata M,Brodbelt JS,Hodder P,Fast W

    更新日期:2013-06-01 00:00:00

  • Synthesis and biological evaluation of 1-substituted-3(5)-(6-methylpyridin-2-yl)-4-(quinolin-6-yl)pyrazoles as transforming growth factor-β type 1 receptor kinase inhibitors.

    abstract::A series of 1-substituted-3(5)-(6-methylpyridin-2-yl)-4-(quinolin-6-yl)pyrazoles 14a-e, 15a-e, 17a-c, and 18a-d have been synthesized and evaluated for their ALK5 inhibitory activity in an enzyme assay and in a cell-based luciferase reporter assay. The 6-quinolinyl pyrazole analogue 14b inhibited ALK5 phosphorylation ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Jin CH,Krishnaiah M,Sreenu D,Rao KS,Subrahmanyam VB,Park CY,Son JY,Sheen YY,Kim DK

    更新日期:2011-04-15 00:00:00

  • Melanogenesis inhibitors from the rhizomes of Alpinia officinarum in B16 melanoma cells.

    abstract::The 80% aqueous acetone extract from the rhizomes of Alpinia officinarum, a Chinese medicinal herb, were found to inhibit melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells. Among the constituents isolated, four diarylheptanoids [5-hydroxy-1,7-diphenyl-3-heptanone, 7-(4('')-hydroxy-3('')-methoxyphe...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Matsuda H,Nakashima S,Oda Y,Nakamura S,Yoshikawa M

    更新日期:2009-08-15 00:00:00

  • Synthesis and anti-HIV-1 evaluation of phosphonates which mimic the 5'-monophosphate of 4'-branched 2',3'-didehydro-2',3'-dideoxy nucleosides.

    abstract::Synthesis of the 4'-ethynyl and 4'-cyano phosphonates 8-11, which mimic the 5'-monophosphate of 4'-branched 2',3'-didehydro-2',3'-dideoxy nucleosides, was investigated by employing the 3',4'-unsaturated nucleosides (13 and 28) as the starting material. The synthesis was initiated by the electrophilic addition of NIS/(...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Kubota Y,Ishizaki N,Haraguchi K,Hamasaki T,Baba M,Tanaka H

    更新日期:2010-10-15 00:00:00

  • Theoretical research in structure characteristics of different inhibitors and differences of binding modes with CBP bromodomain.

    abstract::The CBP (CREB (cAMP responsive element binding protein) binding protein) bromodomain (BRD) could recognize and bind with acetyl K382 of human tumor suppressor protein p53 which the mutation of encoding gene might cause human cancers. CBP-BRD serves as a promising drug target for several disease pathways and a series o...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Wang XS,Zheng QC

    更新日期:2018-02-01 00:00:00

  • Endoperoxide polyketides from a Chinese Plakortis simplex: further evidence of the impact of stereochemistry on antimalarial activity of simple 1,2-dioxanes.

    abstract::Chemical investigation of the organic extract obtained from the sponge Plakortis simplex collected in the South China Sea afforded five new polyketide endoperoxides (2 and 4-7), along with two known analogues (1 and 3). The stereostructures of these metabolites have been deduced on the basis of spectroscopic analysis ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Chianese G,Persico M,Yang F,Lin HW,Guo YW,Basilico N,Parapini S,Taramelli D,Taglialatela-Scafati O,Fattorusso C

    更新日期:2014-09-01 00:00:00

  • Bicyclic [b]-heteroannulated pyridazine derivatives--II. Structure-activity relationships in the 6-aryltriazolo-[4,3-b]pyridazine ligands of the benzodiazepine receptor.

    abstract::Electronic parameters (molecular electrostatic potential MEP, charge distribution on the nitrogen atoms, dipole moment mu and ionization potential IP) were calculated by semiempirical quantum chemistry methods for 2 sets (X = H and m-CF3, the syn- and anti-rotamers of the latter being considered separately) of the 6-a...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Karolak-Wojciechowska J,Lange J,Kwiatkowski W,Gniewosz M,Plenkiewicz J

    更新日期:1994-08-01 00:00:00

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

    abstract::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-co...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


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

    更新日期:2014-04-01 00:00:00

  • Synthesis and structure-activity relationship studies on tryprostatin A, an inhibitor of breast cancer resistance protein.

    abstract::Tryprostatin A is an inhibitor of breast cancer resistance protein, consequently a series of structure-activity studies on the cell cycle inhibitory effects of tryprostatin A analogues as potential antitumor antimitotic agents have been carried out. These analogues were assayed for their growth inhibition properties a...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章


    authors: Jain HD,Zhang C,Zhou S,Zhou H,Ma J,Liu X,Liao X,Deveau AM,Dieckhaus CM,Johnson MA,Smith KS,Macdonald TL,Kakeya H,Osada H,Cook JM

    更新日期:2008-04-15 00:00:00