Benzanilides with spasmolytic activity: chemistry, pharmacology, and SAR.

Abstract:

:The following study describes the synthesis of new benzanilide derivatives and their pharmacological investigation on smooth muscle preparations of guinea pigs. All compounds were synthesized in good yields and showed a spasmolytic activity without significant effect on vascular smooth muscles and heart muscle preparations. Moreover, further pharmacological investigations as well as in silico studies were performed to elucidate the mechanism of action. Compound 3 showed the most potent spasmolytic activity with an IC(50) of 3.25microM.

journal_name

Bioorg Med Chem

authors

Brunhofer G,Handler N,Leisser K,Studenik CR,Erker T

doi

10.1016/j.bmc.2008.04.057

subject

Has Abstract

pub_date

2008-06-01 00:00:00

pages

5974-81

issue

11

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(08)00385-4

journal_volume

16

pub_type

杂志文章
  • Synthesis and DNA binding studies of a new asymmetric cyanine dye binding in the minor groove of [poly(dA-dT)]2.

    abstract::A new asymmetric cyanine dye has been synthesised and its interaction with different DNA has been investigated. In this dye, BEBO, the structure of the known intercalating cyanine dye BO has been extended with a benzothiazole substituent. The resulting crescent-shape of the molecule is similar to that of the well-know...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(02)00463-7

    authors: Karlsson HJ,Lincoln P,Westman G

    更新日期:2003-03-20 00:00:00

  • Study on dual-site inhibitors of acetylcholinesterase: Highly potent derivatives of bis- and bifunctional huperzine B.

    abstract::Natural (-)-huperzine B (HupB), isolated from Chinese medicinal herb, displayed moderate inhibitory activity of acetylcholinesterase (AChE). Based on the active dual-site of AChE, a series of novel derivatives of bis- and bifunctional HupB were designed and synthesized. The AChE inhibition potency of most derivatives ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2006.11.009

    authors: He XC,Feng S,Wang ZF,Shi Y,Zheng S,Xia Y,Jiang H,Tang XC,Bai D

    更新日期:2007-02-01 00:00:00

  • Comparison of the dark and light-induced toxicity of thio and seleno analogues of the thiopyrylium dye AA1.

    abstract::2,6-Bis(4-anilino)-4-(4-N,N-dimethylanilino)thiopyrylium chloride (AA1) and -selenopyrylium chloride (AA1-Se) and 2,6-bis(4-anilino)-4-(4-N-morpholinophenyl)thiopyrylium chloride (1) and -selenopyrylium chloride (2) were prepared via the addition of 4-N,N-dimethylanilino magnesium bromide and 4-N-morpholinophenyl magn...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2004.03.025

    authors: Detty MR,Gibson SL,Hilf R

    更新日期:2004-05-15 00:00:00

  • Design and synthesis of novel androgen receptor antagonists with sterically bulky icosahedral carboranes.

    abstract::Carboranes (dicarba-closo-dodecaboranes) are a class of carbon-containing polyhedral boron-cluster compounds having remarkable chemical and thermal stability, and hydrophobic character. These features may allow application of carboranes as a new hydrophobic core structure in biologically active molecules that interact...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2005.06.061

    authors: Goto T,Ohta K,Suzuki T,Ohta S,Endo Y

    更新日期:2005-12-01 00:00:00

  • Synthesis and hydrolytic behavior of two novel tripartate codrugs of naltrexone and 6beta-naltrexol with hydroxybupropion as potential alcohol abuse and smoking cessation agents.

    abstract::A codrug approach for simultaneous treatment of alcohol abuse and tobacco dependence is considered as very desirable because of substantial evidence that smoking is increased significantly during drinking, and that smoking is regarded as a behavioral 'cue' for the urge to consume alcohol. The purpose of this study was...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2006.06.018

    authors: Hamad MO,Kiptoo PK,Stinchcomb AL,Crooks PA

    更新日期:2006-10-15 00:00:00

  • The novel GABA adamantane derivative (AdGABA): design, synthesis, and activity relationship with gabapentin.

    abstract::A facile preparation of 2-aminomethyl-2-tricyclo[3.3.1.1(1,7)]decaneacetic acid hydrochloride 5 (AdGABA) is described. The synthesis of AdGABA involves the hydrogenation of 2-cyano-2-tricyclo[3.3.1.1(1,7)]decaneacetic acid 11, which was synthesized by two different synthetic routes. AdGABA was found to antagonize the ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2005.02.030

    authors: Zoidis G,Papanastasiou I,Dotsikas I,Sandoval A,Dos Santos RG,Papadopoulou-Daifoti Z,Vamvakides A,Kolocouris N,Felix R

    更新日期:2005-04-15 00:00:00

  • Transition state analogue inhibitors of protozoan nucleoside hydrolases.

    abstract::Protozoan parasites are unable to synthesize purines de novo and must rely on purine salvage pathways for their requirements. Nucleoside hydrolases, which are not found in mammals, function as key enzymes in purine salvage in protozoa. Inhibition of these enzymes may disrupt purine supply and specific inhibitors are p...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(99)00210-2

    authors: Furneaux RH,Schramm VL,Tyler PC

    更新日期:1999-11-01 00:00:00

  • Induction of potent cell growth inhibition by schizophyllan/K-ras antisense complex in combination with gemcitabine.

    abstract::Antisense oligonucleotides (AS-ODNs) specifically hybridize with target mRNAs, resulting in interference with the splicing mechanism or the regulation of protein translation. In our previous reports, we demonstrated that β-glucan schizophyllan (SPG) can form a complex with AS-ODNs attached with oligo deoxyadenosine dA...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2020.115668

    authors: Sasaki S,Izumi H,Morimoto Y,Sakurai K,Mochizuki S

    更新日期:2020-09-15 00:00:00

  • QSAR of the testosterone binding globulin affinity by means of correlation weighting of local invariants of the graph of atomic orbitals.

    abstract::Numerical values of the testosterone binding globulin affinity have been modeled as a mathematical function of molecular structure in two versions of molecular structure elucidation: first, by hydrogen-filled molecular graphs (HFG); second, by the so-called graphs of atomic orbitals (GAO). Increased orders of Morgan e...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2005.07.059

    authors: Raska I Jr,Toropov A

    更新日期:2005-12-15 00:00:00

  • Novel azalides derived from 16-membered macrolides. Part II: Isolation of the linear 9-formylcarboxylic acid and its sequential macrocyclization with an amino alcohol or an azidoamine.

    abstract::The design and synthesis of novel 14- to 16-membered 11-azalides starting from 16-membered macrolides are reported. A linear 9-formylcarboxylic acid was isolated via a mobile dialdehyde previously reported. Sequential macrocyclization of the formylcarboxylic acid with amino alcohol followed by deprotection afforded co...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.09.054

    authors: Miura T,Kanemoto K,Natsume S,Atsumi K,Fushimi H,Yoshida T,Ajito K

    更新日期:2008-12-01 00:00:00

  • A genetically selected cyclic peptide inhibitor of BCL6 homodimerization.

    abstract::We report an inhibitor of the homodimeric protein-protein interaction of the BCL6 oncoprotein, identified from a genetically encoded SICLOPPS library of 3.2 million cyclic hexapeptides in combination with a bacterial reverse two-hybrid system. This cyclic peptide is shown to bind the BTB domain of BCL6, disrupts its h...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2018.03.012

    authors: Osher EL,Castillo F,Elumalai N,Waring MJ,Pairaudeau G,Tavassoli A

    更新日期:2018-07-15 00:00:00

  • A combination of in silico and SAR studies to identify binding hot spots of Bcl-xL inhibitors.

    abstract::Inhibition of Bcl-2 family protein-protein interactions (PPI) is a very promising direction in cancer chemotherapy. Hence over the last decade, many medicinal chemistry studies endeavoured to discover drug candidates, and a wealth of chemical scaffolds with striking chemical diversity was reported as Bcl-xL inhibitors...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2015.02.060

    authors: Levoin N,Vo DD,Gautier F,Barillé-Nion S,Juin P,Tasseau O,Grée R

    更新日期:2015-04-15 00:00:00

  • Dolichylpyrophosphate oligosaccharides: large-scale isolation and evaluation as oligosaccharyltransferase substrates.

    abstract::Oligosaccharyltransferase (OST) catalyzes the transfer of a branched oligosaccharide from a dolichylpyrophosphate oligosaccharide (Dol-PP-OS) to the asparagine of a nascent polypeptide chain in vivo and peptide substrates in vitro. Here we report the isolation and purification of Dol-PP-OS from bovine pancreas and thy...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(98)00268-5

    authors: Gibbs BS,Coward JK

    更新日期:1999-03-01 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

    doi:10.1016/j.bmc.2007.09.032

    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

  • Synthesis, structural analysis and antitumor activity of novel 17α-picolyl and 17(E)-picolinylidene A-modified androstane derivatives.

    abstract::The heterocyclic ring at C-17 position of the androstane compounds plays an important role in biological activity. The aim of the present study was to synthesize and evaluate potential antitumor activity of different A-modified 17α-picolyl and 17(E)-picolinylidene androstane derivatives. In several synthetic steps, no...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2015.02.001

    authors: Ajduković JJ,Penov Gaši KM,Jakimov DS,Klisurić OR,Jovanović-Šanta SS,Sakač MN,Aleksić LD,Djurendić EA

    更新日期:2015-04-01 00:00:00

  • No carrier added synthesis of O-(2'-[18F]fluoroethyl)-L-tyrosine via a novel type of chiral enantiomerically pure precursor, NiII complex of a (S)-tyrosine Schiff base.

    abstract::O-(2'-[(18)F]fluoroethyl)-l-tyrosine ([(18)F]FET) has gained much attention as a promising amino acid radiotracer for tumor imaging with positron emission tomography (PET) due to favorable imaging characteristics and relatively long half-life of (18)F (110min) allowing remote-site application. Here we present a novel ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.03.040

    authors: Krasikova RN,Kuznetsova OF,Fedorova OS,Maleev VI,Saveleva TF,Belokon YN

    更新日期:2008-05-01 00:00:00

  • Synthesis and biological evaluation of BMS-986120 and its deuterated derivatives as PAR4 antagonists.

    abstract::BMS-986120 is a PAR4 antagonist that is being investigated as an antiplatelet agent in phase I clinical trial. An improved synthesis of BMS-986120 has been developed. Based on the novel synthetic approach to BMS-986120, a series of deuterated derivatives of BMS-986120 have been synthesized and biologically evaluated t...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2018.11.024

    authors: Chen P,Ren S,Song H,Chen C,Chen F,Xu Q,Kong Y,Sun H

    更新日期:2019-01-01 00:00:00

  • Syntheses, activity and modeling studies of 3- and 4-(sulfo- and sulfonamidoalkyl)pyridine and piperidine-2-carboxylic acid derivatives as analogs of NMDA receptor antagonists.

    abstract::A series of 3- and 4-(sulfo- and sulfonamidoalkyl)pyridine and piperidine-2-carboxylic acid derivatives as analogs of NMDA receptor antagonists was prepared. Affinity for the NMDA receptor was determined by binding assays using the specific radioligand [3H] (2SR,4RS)-4-(phosphonomethyl)piperidine-2-carboxylic acid (CG...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/0968-0896(95)00087-w

    authors: el Hadri A,Maldivi P,Leclerc G,Rocher JP

    更新日期:1995-09-01 00:00:00

  • Factors that influence T box riboswitch efficacy and tRNA affinity.

    abstract::The T box riboswitch is an intriguing potential target for antibacterial drug discovery. Found primarily in Gram-positive bacteria, the riboswitch regulates gene expression by selectively responding to uncharged tRNA to control transcription readthrough. Polyamines and molecular crowding are known to specifically affe...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2015.07.018

    authors: Zeng C,Zhou S,Bergmeier SC,Hines JV

    更新日期:2015-09-01 00:00:00

  • Rickettsia prowazekii methionine aminopeptidase as a promising target for the development of antibacterial agents.

    abstract::Methionine aminopeptidase (MetAP) is a class of ubiquitous enzymes essential for the survival of numerous bacterial species. These enzymes are responsible for the cleavage of N-terminal formyl-methionine initiators from nascent proteins to initiate post-translational modifications that are often essential to proper pr...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2016.11.013

    authors: Helgren TR,Chen C,Wangtrakuldee P,Edwards TE,Staker BL,Abendroth J,Sankaran B,Housley NA,Myler PJ,Audia JP,Horn JR,Hagen TJ

    更新日期:2017-02-01 00:00:00

  • Exploring a synthetic organoselenium compound for antioxidant pharmacotherapy--toxicity and effects on ROS-production.

    abstract::The organoselenium antioxidant 1 was previously found to act as a catalytic antioxidant in a two-phase lipid peroxidation system. In aqueous environment, selenide 1 quenched ABTS-radicals more efficiently than Trolox and ascorbic acid. The selenide dose-dependently scavenged reactive oxygen and nitrogen species more e...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2010.01.057

    authors: Johansson H,Svartström O,Phadnis P,Engman L,Ott MK

    更新日期:2010-03-01 00:00:00

  • Dihydrofolate reductase and cell growth activity inhibition by the beta-carboline-benzoquinolizidine plant alkaloid deoxytubulosine from Alangium lamarckii: its potential as an antimicrobial and anticancer agent.

    abstract::Beta-carboline-benzoquinolizidine plant alkaloid deoxytubulosine (DTB) was evaluated and assessed for the first time for its biochemical and biological activity employing the biomarker dihydrofolate reductase (DHFR) (5,6,7,8-tetrahydrofolate: NADP+ oxidoreductase, EC 1.5.1.3) as the probe enzyme, a key target in cance...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0968-0896(98)00262-4

    authors: Rao KN,Venkatachalam SR

    更新日期:1999-06-01 00:00:00

  • Analogues of DNA minor groove cross-linking agents incorporating aminoCBI, an amino derivative of the duocarmycins: Synthesis, cytotoxicity, and potential as payloads for antibody-drug conjugates.

    abstract::A Pd-catalysed amination method is used to convert seco-CBI, a synthetic analogue of the alkylating subunit of the duocarmycin natural products, from the phenol to amino form. This allows efficient enantioselective access to the more potent S enantiomer of aminoCBI and its incorporation into analogues of DNA minor gro...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2016.09.068

    authors: Giddens AC,Lee HH,Lu GL,Miller CK,Guo J,Lewis Phillips GD,Pillow TH,Tercel M

    更新日期:2016-11-15 00:00:00

  • Covalent inhibition of SUMO and ubiquitin-specific cysteine proteases by an in situ thiol-alkyne addition.

    abstract::Posttranslational modification of proteins with ubiquitin and ubiquitin-like modifiers such as SUMO can be reverted by specific proteases, also referred to as deubiquitinases and isopeptidases, most of which are cysteine-dependent. We have found that the replacement of the conserved C-terminal glycine with propargylam...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2013.02.039

    authors: Sommer S,Weikart ND,Linne U,Mootz HD

    更新日期:2013-05-01 00:00:00

  • Synthesis, binding, nuclease resistance and cellular uptake properties of 2'-O-acetalester-modified oligonucleotides containing cationic groups.

    abstract::We report on the synthesis and properties of oligonucleotides (ONs) with 2'-O-acetalester modifications containing cationic side chains in a prodrug-like approach. In the aim to improve cell penetration and nuclease resistance, various different amino- or guanidino-acetalester were grafted to 2'-OH of uridine and the ...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2015.07.054

    authors: Biscans A,Rouanet S,Bertrand JR,Vasseur JJ,Dupouy C,Debart F

    更新日期:2015-09-01 00:00:00

  • Search for new pharmacophores for antimalarial activity. Part II: synthesis and antimalarial activity of new 6-ureido-4-anilinoquinazolines.

    abstract::Synthesis of new 6-ureido-4-anilinoquinazolines have been accomplished and their in vitro antimalarial activity against chloroquine-sensitive P. falciparum have been examined. Out of 64 compounds evaluated, the IC(50) of 16 compounds which have displayed MIC of 0.25 microg/mL were also recorded. One of the compounds (...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2008.11.005

    authors: Madapa S,Tusi Z,Mishra A,Srivastava K,Pandey SK,Tripathi R,Puri SK,Batra S

    更新日期:2009-01-01 00:00:00

  • Facile preparation of deuterium-labeled N-acylhomoserine lactones as internal standards for isotope dilution mass spectrometry.

    abstract::N-Acylhomoserine lactones (AHLs) are widely conserved signal molecules that mediate quorum sensing in Gram-negative bacteria. In this study, deuterium-labeled AHLs were prepared for use as internal standards for isotope dilution mass spectrometry. Their utility in the sensitive and precise quantification of AHLs in cu...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2010.04.055

    authors: Kai K,Tani A,Hayashi H

    更新日期:2010-06-01 00:00:00

  • Design, synthesis and biological evaluation of N,N-3-phenyl-3-benzylaminopropanamide derivatives as novel cholesteryl ester transfer protein inhibitor.

    abstract::A series of N,N-3-phenyl-3-benzylaminopropanamide derivatives were identified as novel CETP (cholesteryl ester transfer protein) inhibitors. In our previous study, lead compound L10 was discovered by pharmacophore-based virtual screening (Dong-Mei Zhao et al., 2014). Based on L10 (IC50 8.06 μM), compound HL6 (IC50 10....

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2015.12.010

    authors: Zhao D,Xie H,Bai C,Liu C,Hao C,Zhao S,Yuan H,Luo C,Wang J,Lin B,Zheng J,Cheng M

    更新日期:2016-04-15 00:00:00

  • Synthesis and biological evaluation of pyrido[2,3-d]pyrimidine-2,4-dione derivatives as eEF-2K inhibitors.

    abstract::A small molecule library of pyrido[2,3-d]pyrimidine-2,4-dione derivatives 6-16 was synthesized from 6-amino-1,3-disubstituted uracils 18, characterized, and screened for inhibitory activity against eukaryotic elongation factor-2 kinase (eEF-2K). To understand the binding pocket of eEF-2K, structural modifications of t...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2014.06.050

    authors: Edupuganti R,Wang Q,Tavares CD,Chitjian CA,Bachman JL,Ren P,Anslyn EV,Dalby KN

    更新日期:2014-09-01 00:00:00

  • Efficient synthesis of Hsp90 inhibitor dimers as potential antitumor agents.

    abstract::The PU-H58-dimers 13a-15b were efficiently synthesized and their biological properties were evaluated. The copper-catalyzed alkyne azide coupling was effective in simultaneously linking three components via a triazole formation to afford the target dimers. These synthesized dimers exhibited binding affinity to the N-t...

    journal_title:Bioorganic & medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.bmc.2010.05.075

    authors: Sekiguchi H,Muranaka K,Osada A,Ichikawa S,Matsuda A

    更新日期:2010-08-01 00:00:00