当前位置： SCI文献检索 > EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY期刊下所有文献 > Application of (quantitative) structure-activity relationships to progestagens: from serendipity to structure-based design.

Application of (quantitative) structure-activity relationships to progestagens: from serendipity to structure-based design.

Abstract：

:Progestagens are drugs, which are widely used in hormonal contraception and in hormone-replacement therapy. Since the natural hormone, progesterone, lacks oral activity, much effort has been devoted to finding analogues with improved oral activity and, preferably, higher potency and selectivity. A crystal structure of the hormone binding domain (HBD) region of the progesterone receptor (PR) could only be obtained recently. For more than forty years the process of designing new progestagens could therefore only be guided by the knowledge of the structure of the ligand and its corresponding in vitro/in vivo activities. While in early days chemical intuition and simple statistics (structure-activity relationship - SAR) were leading the drug design process, in later days more complex statistics and visualization tools have become routinely part of quantitative structure-activity relationship (QSAR) studies. The present review aims to provide a general overview of the strategies, efforts and achievements of synthetic and computational chemists in more than forty years of development of progestagens.

journal_name

Eur J Med Chem

journal_title

European journal of medicinal chemistry

authors

Bursi R,Groen MB

doi

10.1016/s0223-5234(00)00168-9

subject

Has Abstract

pub_date

2000-09-01 00:00:00

pages

787-96

issue

9

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(00)00168-9

journal_volume

35

pub_type

杂志文章,评审

相关文献

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY文献大全
  • Discovery and optimization of benzenesulfonamides-based hepatitis B virus capsid modulators via contemporary medicinal chemistry strategies.

    abstract：:Hepatitis B is a vaccine-preventable, but potentially life-threatening liver infection caused by the Hepatitis B virus (HBV). It represents an important health burden, with 257 million active cases globally. Current HBV treatments using nucleos(t)ide analogs and pegylated interferons cannot alleviate the situation com...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章,评审

    doi：10.1016/j.ejmech.2020.112714

    authors： Ren Y,Ma Y,Cherukupalli S,Tavis JE,Menéndez-Arias L,Liu X,Zhan P

    更新日期：2020-11-15 00:00:00

  • Potential cytotoxic and anti-metastatic effects of berberine on gynaecological cancers with drug-associated resistance.

    abstract：:Gynaecological disorders, such as cervical, ovarian, and endometrial cancers are the second most prevalent cancer types in women worldwide. Therapeutic approaches for gynaecological cancers involve chemotherapy, radiation, and surgery. However, lifespan is not improved, and novel medications are required. Among variou...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章,评审

    doi：10.1016/j.ejmech.2019.111951

    authors： Mortazavi H,Nikfar B,Esmaeili SA,Rafieenia F,Saburi E,Chaichian S,Heidari Gorji MA,Momtazi-Borojeni AA

    更新日期：2020-02-01 00:00:00

  • Synthesis and primary cytotoxicity evaluation of new 5-nitroindole-2,3-dione derivatives.

    abstract：:A new series of 5-nitro-1H-indole-2,3-dione-3-thiosemicarbazones (3a-k) obtained by condensation of 5-nitro-1H-indole-2,3-dione (1) with N-substituted-thiosemicarbazides (2a-k) were treated with morpholine or piperidine and formaldehyde to yield 1-morpholino/piperidinomethyl-5-nitroindole-2,3-dione-3-thiosemicarbazone...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0223-5234(02)01416-2

    authors： Karali N

    更新日期：2002-11-01 00:00:00

  • Design and one-pot synthesis of alpha-aminophosphonates and bis(alpha-aminophosphonates) by iron(III) chloride and cytotoxic activity.

    abstract：:In this study, we used a solution of FeCl(3) in THF to facilitate the Mannich-type reaction of aldehyde, amine and phosphite compounds to form corresponding alpha-aminophosphonates in a one-pot, three-component reaction. Selected alpha-aminophosphonates were entered into a biological assay test and were studied by doc...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2009.07.009

    authors： Rezaei Z,Firouzabadi H,Iranpoor N,Ghaderi A,Jafari MR,Jafari AA,Zare HR

    更新日期：2009-11-01 00:00:00

  • Synthesis and anticancer activity of new dihydropyrimidinone derivatives.

    abstract：:A series of dihydropyrimidinone derivatives bearing various N-heterocyclic moieties was designed and synthesized. Twelve new compounds were screened for their cytotoxic activity using 60 cancer cell lines according to NCI (USA) protocol. Compound 19 showed a significant activity against NCI-H460, SK-MEL-5, and HL-60 (...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2018.07.004

    authors： Mostafa AS,Selim KB

    更新日期：2018-08-05 00:00:00

  • Design, synthesis and antifungal activities of novel pyrrole alkaloid analogs.

    abstract：:A series of novel analogs of pyrrole alkaloid were designed and synthesized by a facile method and their structures were characterized by 1H NMR, 13C NMR and high-resolution mass spectrometry (HRMS). The structure of compound 2a was identified by 2D NMR including heteronuclear multiple-quantum coherence (HMQC), hetero...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2011.01.031

    authors： Wang MZ,Xu H,Liu TW,Feng Q,Yu SJ,Wang SH,Li ZM

    更新日期：2011-05-01 00:00:00

  • (5aR)-5a-C-Pentyl-4-epi-isofagomine: A powerful inhibitor of lysosomal β-galactosidase and a remarkable chaperone for mutations associated with GM1-gangliosidosis and Morquio disease type B.

    abstract：:This report is about the identification, synthesis and initial biological characterization of derivatives of 4-epi-isofagomine as pharmacological chaperones (PC) for human lysosomal β-galactosidase. The two epimers of 4-epi-isofagomine carrying a pentyl group at C-5a, namely (5aR)- and (5aS)-5a-C-pentyl-4-epi-isofagom...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2016.09.095

    authors： Front S,Biela-Banaś A,Burda P,Ballhausen D,Higaki K,Caciotti A,Morrone A,Charollais-Thoenig J,Gallienne E,Demotz S,Martin OR

    更新日期：2017-01-27 00:00:00

  • Novel ciprofloxacin hybrids using biology oriented drug synthesis (BIODS) approach: Anticancer activity, effects on cell cycle profile, caspase-3 mediated apoptosis, topoisomerase II inhibition, and antibacterial activity.

    abstract：:As we are interested in synthetizing biologically active leads with dual anticancer and antibacterial activity, we adopted biology oriented drug synthesis (BIODS) strategy to synthesize a series of novel ciprofloxacin (CP) hybrids. The National Cancer Institute (USA) selected seventeen newly synthesized compounds for ...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2018.03.026

    authors： Kassab AE,Gedawy EM

    更新日期：2018-04-25 00:00:00

  • Ferrocene-based guanidine derivatives: in vitro antimicrobial, DNA binding and docking supported urease inhibition studies.

    abstract：:Some novel ferrocenyl guanidines 1-8 were synthesized and characterized by different spectroscopic methods, elemental analysis and single crystal X-rays diffraction techniques. The crystallographic studies revealed that the existence of the strong non-bonding interactions facilitate these molecules to interact with bi...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2014.07.109

    authors： Gul R,Rauf MK,Badshah A,Azam SS,Tahir MN,Khan A

    更新日期：2014-10-06 00:00:00

  • Novel benzylidenephenylpyrrolizinones with pleiotropic activities potentially useful in Alzheimer's disease treatment.

    abstract：:This work describes the synthesis and the biological evaluation of novel benzylidenephenylpyrrolizinones as potential antioxidant, metal chelating or amyloid β (βA) aggregation inhibitors. Some derivatives exhibited interesting results in regard to several of the performed evaluations and appear as valuable Multi-Targ...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2016.03.023

    authors： Jourdan JP,Since M,El Kihel L,Lecoutey C,Corvaisier S,Legay R,Sopkova-de Oliveira Santos J,Cresteil T,Malzert-Fréon A,Rochais C,Dallemagne P

    更新日期：2016-05-23 00:00:00

  • Synthesis and antimicrobial activities of hexahydroimidazo[1,5-a]pyridinium bromides with varying benzyl substituents.

    abstract：:Variously substituted benzyl bromides were employed to quaternize hexahydrobenzylimidazo[1,5-a]pyridine (A) and the resulting bromides (1-11) were evaluated for their in vitro antimicrobial activity against 10 pathogenic microorganisms: Staphylococcus aureus, Staphylococcus epidermidis, Bacillus cereus, Micrococcus lu...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2011.04.012

    authors： Türkmen H,Ceyhan N,Ulkü Karabay Yavaşoğlu N,Ozdemir G,Cetinkaya B

    更新日期：2011-07-01 00:00:00

  • Synthesis and SAR studies of mono O-prenylated coumarins as potent 15-lipoxygenase inhibitors.

    abstract：:All of the mono isopentenyloxy, -geranyloxy and -farnesyloxy derivatives of coumarin were synthesized and their inhibitory potency against soybean 15-lipoxygenase (SLO) and human 15-lipoxygenase-1 (HLO-1) were determined. Amongst the synthetic analogs, 5-farnesyloxycoumarin showed the most potent inhibitory activity a...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2012.09.006

    authors： Iranshahi M,Jabbari A,Orafaie A,Mehri R,Zeraatkar S,Ahmadi T,Alimardani M,Sadeghian H

    更新日期：2012-11-01 00:00:00

  • Synthesis and anti-tuberculosis activity of new hetero(Mn, Co, Ni)trinuclear iron(III) furoates.

    abstract：:New hetero(micro(3)-oxo)trinuclear iron(III) furoates with the general formulas [Fe(2)MO(alpha-Fur)(6)(L)(H(2)O)(2)], where L = THF (1-3), DMF (4-5), M = Mn(2+) (1, 4), Co(2+) (2, 5), Ni(2+) (3, 6) and [Fe(2)MO(alpha-Fur)(6)(3Cl-Py)(3)], where M = Mn(2+) (7), Co(2+) (8), Ni(2+) (9); have been synthesised and investiga...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2009.12.053

    authors： Melnic S,Prodius D,Stoeckli-Evans H,Shova S,Turta C

    更新日期：2010-04-01 00:00:00

  • Nitrogen-containing ecdysteroid derivatives vs. multi-drug resistance in cancer: Preparation and antitumor activity of oximes, oxime ethers and a lactam.

    abstract：:Multidrug resistance is a widespread problem among various diseases and cancer is no exception. We had previously described the chemo-sensitizing activity of ecdysteroid derivatives with low polarity on drug susceptible and multi-drug resistant (MDR) cancer cells. We have also shown that these molecules have a marked ...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2017.12.032

    authors： Vágvölgyi M,Martins A,Kulmány Á,Zupkó I,Gáti T,Simon A,Tóth G,Hunyadi A

    更新日期：2018-01-20 00:00:00

  • Stereoselective synthesis and antimicrobial activity of steroidal C-20 tertiary alcohols with thiazole/pyridine side chain.

    abstract：:Stereoselective synthesis of novel steroidal C-20 tertiary alcohols with thiazole and pyridine side chain using Grignard reaction of steroidal ketones and thiazole/pyridine magnesium bromide have been realized. These molecules were evaluated in vitro for their antifungal and antibacterial activities. Most of the compo...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2011.05.032

    authors： Shingate BB,Hazra BG,Salunke DB,Pore VS,Shirazi F,Deshpande MV

    更新日期：2011-09-01 00:00:00

  • Potential of aryl-urea-benzofuranylthiazoles hybrids as multitasking agents in Alzheimer's disease.

    abstract：:New benzofuranylthiazole derivatives containing the aryl-urea moiety were synthesized and evaluated in vitro as dual acetylcholinesterase (AChE)-butyrylcholinesterase (BuChE) inhibitors. In addition, the cupric reducing antioxidant capacities (CUPRAC) and ABTS cation radical scavenging abilities of the synthesized com...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2015.07.005

    authors： Kurt BZ,Gazioglu I,Basile L,Sonmez F,Ginex T,Kucukislamoglu M,Guccione S

    更新日期：2015-09-18 00:00:00

  • Structural modifications in the distal, regulatory region of histamine H3 receptor antagonists leading to the identification of a potent anti-obesity agent.

    abstract：:A series of 4-pyridylpiperazine derivatives with varying regulatory region substituents proved to be potent histamine H3 receptor (H3R) ligands in the nanomolar concentration range. The most influential modification that affected the affinity toward the H3R appeared by introducing electron-withdrawing moieties into th...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2020.113041

    authors： Szczepańska K,Pockes S,Podlewska S,Höring C,Mika K,Latacz G,Bednarski M,Siwek A,Karcz T,Nagl M,Bresinsky M,Mönnich D,Seibel U,Kuder KJ,Kotańska M,Stark H,Elz S,Kieć-Kononowicz K

    更新日期：2020-11-24 00:00:00

  • Imidazo-thiazine, -diazinone and -diazepinone derivatives. Synthesis, structure and benzodiazepine receptor binding.

    abstract：:In our search for new compounds acting on benzodiazepine receptors among the fused 2-thiohydantoin derivatives, a series of arylidene imidazo[2,1-b]thiazines was synthesized. The 1,2- and 2,3- cyclized derivatives of mono- and di-substituted Z-5-arylidene-2-thiohydantoins were examined (the X-ray crystal structure of ...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/s0223-5234(01)01239-9

    authors： Kieć-Kononowicz K,Karolak-Wojciechowska J,Müller CE,Schumacher B,Pekala E,Szymańska E

    更新日期：2001-05-01 00:00:00

  • Clubbed triazoles: a novel approach to antitubercular drugs.

    abstract：:In last few decades, though significant progress has been made in the treatment and control strategies of tubercular infections by introducing new diagnostic and monitoring tools and combination therapy, it still continues to be a severe problem. Thus with the aim of developing novel molecules with improved potency fo...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2006.12.001

    authors： Shiradkar M,Suresh Kumar GV,Dasari V,Tatikonda S,Akula KC,Shah R

    更新日期：2007-06-01 00:00:00

  • Structure-activity relationships of new Organotin(IV) anticancer agents and their cytotoxicity profile on HL-60, MCF-7 and HeLa human cancer cell lines.

    abstract：:There is a growing interest in the cancer cell growth inhibitory effects of organotin (IV) compounds and, accordingly, a new series of dimethyl-, di-(n-butyl)-, diphenyl- and chloro-phenyl tin(IV) complexes with a Schiff base core were prepared. Their binding to DNA was assessed by UV thermal denaturation showing no i...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2019.07.047

    authors： Ullah H,Previtali V,Mihigo HB,Twamley B,Rauf MK,Javed F,Waseem A,Baker RJ,Rozas I

    更新日期：2019-11-01 00:00:00

  • Structure-guided design of pyridoclax derivatives based on Noxa / Mcl-1 interaction mode.

    abstract：:Protein-protein interactions are attractive targets because they control numerous cellular processes. In oncology, apoptosis regulating Bcl-2 family proteins are of particular interest. Apoptotic cell death is controlled via PPIs between the anti-apoptotic proteins hydrophobic groove and the pro-apoptotic proteins BH3...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2018.10.003

    authors： Hedir S,De Giorgi M,Fogha J,De Pascale M,Weiswald LB,Brotin E,Marekha B,Denoyelle C,Denis C,Suzanne P,Gautier F,Juin P,Ligat L,Lopez F,Carlier L,Legay R,Bureau R,Rault S,Poulain L,Oliveira Santos JS,Voisin-Chiret

    更新日期：2018-11-05 00:00:00

  • Synthesis, characterization and biological evaluation of some thiourea derivatives bearing benzothiazole moiety as potential antimicrobial and anticancer agents.

    abstract：:Five series of thiourea derivatives bearing benzothiazole moiety (20 compounds) were efficiently synthesized and evaluated for antimicrobial and anticancer activities. The results indicated that the compounds possessed a broad spectrum of activity against the tested microorganisms and showed higher activity against fu...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2009.12.016

    authors： Saeed S,Rashid N,Jones PG,Ali M,Hussain R

    更新日期：2010-04-01 00:00:00

  • Synthesis, properties, and perspectives of gem-diphosphono substituted-thiazoles.

    abstract：:A series of substituted arylidene thiazoles were allowed to react with Wittig-Horner (WH) reagent, tetraethyl methyl-1,1-bisphosphonate, to produce via Michael addition reaction the corresponding heteroarylmethylenebisphosphonates (BPs) in different yields according to the experimental conditions. Acid hydrolysis of t...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2007.07.005

    authors： Abdou WM,Ganoub NA,Geronikaki A,Sabry E

    更新日期：2008-05-01 00:00:00

  • C-cinnamoyl glycosides as a new class of anti-filarial agents.

    abstract：:A series of C-cinnamoyl glycosides has been synthesized in good yield by the BF3·OEt2 catalyzed aldol condensation of C-glycosylated acetone derivative with a variety of aromatic aldehydes. The synthesized compounds were evaluated for their potential as anti-filarial agents against bovine filarial parasite Setaria cer...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2016.03.001

    authors： Roy P,Dhara D,Parida PK,Kar RK,Bhunia A,Jana K,Sinha Babu SP,Misra AK

    更新日期：2016-05-23 00:00:00

  • Heterodimeric Rifampicin-Tobramycin conjugates break intrinsic resistance of Pseudomonas aeruginosa to doxycycline and chloramphenicol in vitro and in a Galleria mellonella in vivo model.

    abstract：:Intrinsic resistance in Pseudomonas aeruginosa, defined by chromosomally encoded low outer membrane permeability and constitutively over-expressed efflux pumps, is a major reason why the pathogen is refractory to many antibiotics. Herein, we report that heterodimeric rifampicin-tobramycin conjugates break this intrins...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2019.04.034

    authors： Idowu T,Arthur G,Zhanel GG,Schweizer F

    更新日期：2019-07-15 00:00:00

  • Bioactive fused heterocycles: Nucleoside analogs with an additional ring.

    abstract：:The following mini-review summarizes the basic literature data regarding synthesis, biological activity, structure-activity relationship, and discussion of the mechanisms of action of two major classes of nucleoside analogs with fused heterocyclic rings: (i) the ethenonucleosides and their related derivatives of the 5...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章,评审

    doi：10.1016/j.ejmech.2014.12.026

    authors： Jahnz-Wechmann Z,Framski G,Januszczyk P,Boryski J

    更新日期：2015-06-05 00:00:00

  • Topological sub-structural molecular design approach: radical scavenging activity.

    abstract：:In the last decades phenolic compounds have gained enormous interest because of their beneficial health effects such as anti-inflammatory, anticancer, or antiviral activities. The pharmacological effects of phenolic compounds are mainly due to their antioxidant activity and their inhibition of certain enzymes. This an...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2011.12.030

    authors： Pérez-Garrido A,Helguera AM,Ruiz JM,Rentero PZ

    更新日期：2012-03-01 00:00:00

  • Design, synthesis and evaluation of diarylpiperazine derivatives as potent anti-tubercular agents.

    abstract：:Molecular hybridization is an emerging approach to design novel ligands by combination of two or more pharmacophoric subunits of known bioactive compounds. In the present study, we have designed a novel series of diarylpiperazine analogues, synthesized, characterized using FTIR, (1)H NMR, Mass, Elemental analysis and ...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2015.10.024

    authors： Penta A,Franzblau S,Wan B,Murugesan S

    更新日期：2015-11-13 00:00:00

  • Discovery of 3-phenylquinolinylchalcone derivatives as potent and selective anticancer agents against breast cancers.

    abstract：:A number of 3-phenylquinolinylchalcone derivatives were synthesized and evaluated in vitro for their antiproliferative activities against three breast cancer cell lines (MCF-7, MDA-MB-231, and SKBR-3), and a non-cancer normal epithelial cell line (H184B5F5/M10). Among them, (E)-3-[3-(4-methoxyphenyl)quinolin-2-yl]-1-(...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2015.04.054

    authors： Tseng CH,Tzeng CC,Hsu CY,Cheng CM,Yang CN,Chen YL

    更新日期：2015-06-05 00:00:00

  • Synthesis and pharmacological evaluation of novel 5-substituted-1-(phenylsulfonyl)-2-methylbenzimidazole derivatives as anti-inflammatory and analgesic agents.

    abstract：:A series of novel 5-substituted-1-(phenylsulfonyl)-2-methylbenzimidazole derivatives have been synthesized. The structures of these compounds were established by IR, 1H NMR, 13C NMR, Mass spectral data and elemental analyses. Compounds were evaluated for their anti-inflammatory and analgesic activity as well as gastri...

    journal_title：European journal of medicinal chemistry

    pub_type： 杂志文章

    doi：10.1016/j.ejmech.2010.01.067

    authors： Gaba M,Singh D,Singh S,Sharma V,Gaba P

    更新日期：2010-06-01 00:00:00