Progress of the synthesis of condensed pyrazole derivatives (from 2010 to mid-2013).

Abstract:

:Condensed pyrazole derivatives are important heterocyclic compounds due to their excellent biological activities and have been widely applied in pharmaceutical and agromedical fields. In recent years, numerous condensed pyrazole derivatives have been synthesized and advanced to clinic studies with various biological activities. In this review, we summarized the reported synthesis methods of condensed pyrazole derivatives from 2010 until now. All compounds are divided into three parts according to the rings connected to pyrazole-ring, i.e. [5, 5], [5,F 6], and [5, 7]-condensed pyrazole derivatives. The biological activities and applications in pharmaceutical fields are briefly introduced to offer an orientation for the design and synthesis of condensed pyrazole derivatives with good biological activities.

journal_name

Eur J Med Chem

authors

Li M,Zhao BX

doi

10.1016/j.ejmech.2014.07.102

subject

Has Abstract

pub_date

2014-10-06 00:00:00

pages

311-40

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(14)00717-X

journal_volume

85

pub_type

杂志文章,评审
  • Donepezil-butylated hydroxytoluene (BHT) hybrids as Anti-Alzheimer's disease agents with cholinergic, antioxidant, and neuroprotective properties.

    abstract::The multifactorial nature of Alzheimer's disease (AD) calls for the development of multitarget agents addressing key pathogenic processes. A novel family of donepezil-butylated hydroxytoluene (BHT) hybrids were designed, synthesized and evaluated as multifunctional ligands against AD. The optimal compound 7d displayed...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.08.005

    authors: Cai P,Fang SQ,Yang HL,Yang XL,Liu QH,Kong LY,Wang XB

    更新日期:2018-09-05 00:00:00

  • Pharmaceutical salts and cocrystals involving amino acids: a brief structural overview of the state-of-art.

    abstract::Salification of new drug substances in order to improve physico-chemical or solid-state properties (e.g. dissolution rate or solubility, appropriate workup process, storage for further industrial and marketing development) is a well-accepted procedure. Amino acids, like aspartic acid, lysine or arginine take a great p...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2013.11.045

    authors: Tilborg A,Norberg B,Wouters J

    更新日期:2014-03-03 00:00:00

  • Discovery of a sulfamate-based steroid sulfatase inhibitor with intrinsic selective estrogen receptor modulator properties.

    abstract::Steroid sulfatase (STS), the enzyme which converts inactive sulfated steroid precursors into active hormones, is a promising therapeutic target for the treatment of estrogen-sensitive breast cancer. We report herein the synthesis and in vitro study of dual-action STS inhibitors with selective estrogen-receptor modulat...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2016.04.044

    authors: Ouellet C,Maltais R,Ouellet É,Barbeau X,Lagüe P,Poirier D

    更新日期:2016-08-25 00:00:00

  • Development of imidazole alkanoic acids as mGAT3 selective GABA uptake inhibitors.

    abstract::A new series of potential GABA uptake inhibitors starting from of 1H-imidazol-4-ylacetic acid with the carboxylic acid side chain originating from different positions and varying in length have been synthesized and tested for the inhibitory potency at the four GABA uptake transporters mGAT1-4 stably expressed in HEK c...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.01.042

    authors: Hack S,Wörlein B,Höfner G,Pabel J,Wanner KT

    更新日期:2011-05-01 00:00:00

  • Design, synthesis and biological evaluation of quinazoline-phosphoramidate mustard conjugates as anticancer drugs.

    abstract::A series of novel compounds with phosphoramide mustard functionality incorporated into the quinazoline scaffold of EGFR/HER2 inhibitors were designed and synthesized as multi-target-directed ligands against tumor cells. In vitro assays showed that tumor cell lines with high HER2 level were more sensitive to the compou...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2016.12.055

    authors: Lin S,Li Y,Zheng Y,Luo L,Sun Q,Ge Z,Cheng T,Li R

    更新日期:2017-02-15 00:00:00

  • α- and β-hydrazino acid-based pseudopeptides inhibit the chymotrypsin-like activity of the eukaryotic 20S proteasome.

    abstract::We describe the synthesis of a library of new pseudopeptides and their inhibitory activity of the rabbit 20S proteasome chymotrypsin-like (ChT-L) activity. We replaced a natural α-amino acid by an α- or a β-hydrazino acid and obtained inhibitors of proteasome up to a submicromolar range (0.7 μM for molecule 24b). Stru...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.09.059

    authors: Bordessa A,Keita M,Maréchal X,Formicola L,Lagarde N,Rodrigo J,Bernadat G,Bauvais C,Soulier JL,Dufau L,Milcent T,Crousse B,Reboud-Ravaux M,Ongeri S

    更新日期:2013-01-01 00:00:00

  • New alpha-(N)-heterocyclichydrazones: evaluation of anticancer, anti-HIV and antimicrobial activity.

    abstract::A series of 3- and 5-methylthiophene-2-carboxaldehyde alpha-(N)-heterocyclichydrazones were synthesized and submitted to an in vitro investigation of their anticancer, anti-HIV and antimicrobial activities. Some of the newly synthesized compounds were found to possess antiproliferative properties, whereas no anti-HIV ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2003.09.012

    authors: Savini L,Chiasserini L,Travagli V,Pellerano C,Novellino E,Cosentino S,Pisano MB

    更新日期:2004-02-01 00:00:00

  • Synthesis and biological screening of some novel amidocarbamate derivatives of ketoprofen.

    abstract::A series of novel ketoprofen derivatives 4a-j bearing both amide and carbamate functionalities were prepared using benzotriazole. Selective reduction of ketoprofen produced hydroxy derivative 2, which reacts with one or 2 mol of 1-benzotriazole carboxylic acid chloride (1) gave benzotriazole derivatives 3a and 3b resp...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,收录出版

    doi:10.1016/j.ejmech.2010.04.008

    authors: Sahoo PK,Behera P

    更新日期:2010-07-01 00:00:00

  • Design, synthesis and antiproliferative activities of biarylolefins based on polyhydroxylated and carbohydrate scaffolds.

    abstract::A series of diversely substituted biarylolefins based on carbohydrate and dihydroxyethylene scaffolds were synthesized and evaluated for antiproliferative activity against a panel of human tumor cell lines. Among the thirty-five yet unknown biarylolefins prepared, six displayed potent antiproliferative activities with...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.05.021

    authors: Novoa A,Pellegrini-Moïse N,Bourg S,Thoret S,Dubois J,Aubert G,Cresteil T,Chapleur Y

    更新日期:2011-09-01 00:00:00

  • Mastering tricyclic ring systems for desirable functional cannabinoid activity.

    abstract::There is growing interest in using cannabinoid receptor 2 (CB2) agonists for the treatment of neuropathic pain and other indications. In continuation of our ongoing program aiming for the development of new small molecule cannabinoid ligands, we have synthesized a novel series of carbazole and γ-carboline derivatives....

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.09.038

    authors: Petrov RR,Knight L,Chen SR,Wager-Miller J,McDaniel SW,Diaz F,Barth F,Pan HL,Mackie K,Cavasotto CN,Diaz P

    更新日期:2013-11-01 00:00:00

  • The synthesis and biological evaluation of new DNA-directed alkylating agents, phenyl N-mustard-4-anilinoquinoline conjugates containing a urea linker.

    abstract::We synthesized a series of phenyl N-mustard-4-anilinoquinoline conjugates to study their antitumorigenic effects. These agents were prepared by the condensation of 4-[N,N-bis(2-chloroethyl)amino]phenyl isocyanate with 6-amino-4-methylamino or 4-anilinoquinolines. The structure-activity relationship (SAR) studies revea...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.06.066

    authors: Marvania B,Kakadiya R,Christian W,Chen TL,Wu MH,Suman S,Tala K,Lee TC,Shah A,Su TL

    更新日期:2014-08-18 00:00:00

  • Synthesis and biological activity of 4-thiazolidinones, thiosemicarbazides derived from diflunisal hydrazide.

    abstract::Two novel series of 4-thiazolidinone derivatives, namely 2',4'-difluoro-4-hydroxybiphenyl-3-carboxylic acid [2-(5-nitro-2-furyl/substituted phenyl)-4-thiazolidinone-3-yl]amides (5a-g) and 2-(2',4'-difluoro-4-hydroxybiphenyl-3-carbonylhydrazono)-3-alkyl/aryl-4-thiazolidinones (6a-e) together with 5-(2',4'-difluoro-4-hy...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2005.11.005

    authors: Küçükgüzel G,Kocatepe A,De Clercq E,Sahin F,Güllüce M

    更新日期:2006-03-01 00:00:00

  • New dimeric cyclodiphosph(V)azane complexes of Cr(III), Co(II), Ni(II), Cu(II), and Zn(II): preparation, characterization and biological activity studies.

    abstract::The complexes of type [CrLCl](2).3.5H(2)O and [ML(H(2)O)](2).nH(2)O in which M = Co(II); n = 1, Ni(II); n = 4, Cu(II); n = 0.5 and Zn(II); n = 2 ions and L is 1,3-dimethyl-2,4-dioxo-2',4'-bis(2iminothiophene)cyclodiphosph(V)azane, were prepared and their structures characterized by elemental analysis, IR, (1)H NMR, (3...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2009.12.008

    authors: Alaghaz AN,Ammar RA

    更新日期:2010-04-01 00:00:00

  • Microwave assisted synthesis of unsaturated jasmone heterocyclic analogues as new fragrant substances.

    abstract::Taking the rising interest in jasmone structure based fragrant compounds into account it has been decided to take up an attempt to synthesize the new heterocyclic derivatives of this 2,3-disubstituted cyclopentenone, which could be characterized by the ability of interaction with the same receptors with which jasmone ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2008.07.028

    authors: Pawełczyk A,Zaprutko L

    更新日期:2009-07-01 00:00:00

  • Synthesis, antiproliferative activity and inhibition of tubulin polymerization by anthracenone-based oxime derivatives.

    abstract::A series of anthracenone-based oxime ethers and -esters were synthesized in order to evaluate their antiproliferative activity. Several investigated compounds displayed strong antiproliferative activity against K562 leukemia cells and proved to be strong inhibitors of tubulin polymerization. In this context, anthracen...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2010.04.019

    authors: Surkau G,Böhm KJ,Müller K,Prinz H

    更新日期:2010-08-01 00:00:00

  • Design, synthesis and biological evaluation of novel 7H-pyrrolo[2,3-d]pyrimidine derivatives as potential FAK inhibitors and anticancer agents.

    abstract::A series of 7H-pyrrolo[2,3-d]pyrimidine derivatives possessing a dimethylphosphine oxide moiety were designed, synthesized and evaluated as novel Focal adhesion kinase (FAK) inhibitors. Most compounds potently suppressed the enzymatic activities of FAK, with IC50 values in the 10-8-10-9 M range, and potently inhibited...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2019.111716

    authors: Wang R,Chen Y,Zhao X,Yu S,Yang B,Wu T,Guo J,Hao C,Zhao D,Cheng M

    更新日期:2019-12-01 00:00:00

  • 6-Amino-2,4,5-trimethylpyridin-3-ols: a new general synthetic route and antiangiogenic activity.

    abstract::A new synthetic strategy for preparation of a wide range of 6-amino-2,4,5-trimethylpyridin-3-ols from pyridoxine·HCl via a six-step sequence has been developed. This approach features an introduction of various amino groups to C(6)-position of 3-benzyloxy-6-bromo-2,4,5-trimethylpyridine (13), a key intermediate, by a ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.03.045

    authors: Kim DG,Kang Y,Lee H,Lee EK,Nam TG,Kim JA,Jeong BS

    更新日期:2014-05-06 00:00:00

  • A macrolactone from benzo[a]phenazine with potent activity against Mycobacterium tuberculosis.

    abstract::We report here an alternative to the MCPBA or ozonolysis-based oxidation methods of quinoxaline-featuring compounds prepared from beta-lapachones. The use of peracetic acid allowed a simple preparation of the corresponding macrolactones by cleavage of the ring system. These lactones were evaluated for their antimycoba...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2008.06.014

    authors: Silva RS,Pinto Mdo C,Goulart MO,de Souza Filho JD,Neves I Jr,Lourenço MC,Pinto AV

    更新日期:2009-05-01 00:00:00

  • Synthesis and biological evaluation of novel alkylated polyamine analogues as potential anticancer agents.

    abstract::A new class of polyamine analogues modified by alkylation at the terminal of the polyamine chain has been synthesized and their structures were determined by 1H NMR, 13C NMR, ESI-MS and elemental analysis. As the representative compound, 3f displayed a broad spectrum of anti-cancer effects by MTT assays. Tumor xenogra...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.10.069

    authors: Li M,Wang Y,Ge C,Chang L,Wang C,Tian Z,Wang S,Dai F,Zhao L,Xie S

    更新日期:2018-01-01 00:00:00

  • Synthesis and antifungal activities of some aryl [3-(imidazol-1-yl/triazol-1-ylmethyl) benzofuran-2-yl] ketoximes.

    abstract::In this study, some aryl [3-(imidazol-1-yl/triazol-1-ylmethyl)benzofuran-2-yl] ketones, aryl (3-methyl-benzofuran-2-yl) ketoximes and aryl [3-(imidazol-1-yl/triazol-1-ylmethyl)benzofuran-2-yl] ketoximes were synthesised starting from 2-aryloyl-3-methyl-benzofuranes. The structure elucidation of the compounds was perfo...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2005.12.013

    authors: Gündoğdu-Karaburun N,Benkli K,Tunali Y,Uçucu U,Demirayak S

    更新日期:2006-05-01 00:00:00

  • Microwave assisted synthesis of fragrant jasmone heterocyclic analogues.

    abstract::cis-Jasmone, from jasmonoid group, is an important jasmine odor fragrance compound. The syntheses of new heterocyclic analogues of jasmone were described. Five analogues of this compound were prepared under microwave irradiation and the results of the microwave assisted syntheses were compared with classical, thermall...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2005.09.012

    authors: Pawełczyk A,Zaprutko L

    更新日期:2006-05-01 00:00:00

  • Platanic acid: A new scaffold for the synthesis of cytotoxic agents.

    abstract::Thirty-seven different derivatives (2-38) have been prepared from platanic acid, a natural occurring triterpenoid. Main emphasis was the introduction of several N-containing functional groups such as amines, amides and oximes and their screening for cytotoxic activity employing several human tumor cell lines using SRB...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.11.046

    authors: Kahnt M,Heller L,Grabandt P,Al-Harrasi A,Csuk R

    更新日期:2018-01-01 00:00:00

  • Structure-activity relationship studies and pharmacological characterization of N5-heteroarylalkyl-substituted-2-(2-furanyl)thiazolo[5,4-d]pyrimidine-5,7-diamine-based derivatives as inverse agonists at human A2A adenosine receptor.

    abstract::This paper describes the synthesis and characterization of N5-(hetero)arylalkyl-substituted-thiazolo [5,4-d]pyrimidine-5,7-diamine derivatives (4-19) as novel human (h) A2A adenosine receptor (AR) inverse agonists. Competition binding and cyclic AMP assays indicate that the examined compounds behave as hA2A AR inverse...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.06.020

    authors: Varano F,Catarzi D,Vincenzi F,Falsini M,Pasquini S,Borea PA,Colotta V,Varani K

    更新日期:2018-07-15 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

  • Inhibition of vertebrate aldehyde oxidase as a therapeutic treatment for cancer, obesity, aging and amyotrophic lateral sclerosis.

    abstract::The aldehyde oxidases (AOXs) are a small sub-family of cytosolic molybdo-flavoenzymes, which are structurally conserved proteins and broadly distributed from plants to animals. AOXs play multiple roles in both physiological and pathological processes and AOX inhibition is of increasing significance in the development ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2019.111948

    authors: Qiao Y,Maiti K,Sultana Z,Fu L,Smith R

    更新日期:2020-02-01 00:00:00

  • New Atglistatin closely related analogues: Synthesis and structure-activity relationship towards adipose triglyceride lipase inhibition.

    abstract::Adipose Triglyceride Lipase (ATGL) performs the first and rate-limiting step in lipolysis by hydrolyzing triacylglycerols stored in lipid droplets to diacylglycerols. By mediating lipolysis in adipose and non-adipose tissues, ATGL is a major regulator of overall energy metabolism and plasma lipid levels. Since chronic...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2016.04.021

    authors: Roy PP,D'Souza K,Cuperlovic-Culf M,Kienesberger PC,Touaibia M

    更新日期:2016-08-08 00:00:00

  • Design, synthesis and characterization of peptidomimetic conjugate of BODIPY targeting HER2 protein extracellular domain.

    abstract::Among the EGFRs, HER2 is a major heterodimer partner and also has important implications in the formation of particular tumors. Interaction of HER2 protein with other EGFR proteins can be modulated by small molecule ligands and, hence, these protein-protein interactions play a key role in biochemical reactions related...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.04.038

    authors: Banappagari S,McCall A,Fontenot K,Vicente MG,Gujar A,Satyanarayanajois S

    更新日期:2013-07-01 00:00:00

  • Discovery of novel series of 2-substituted benzo[d]oxazol-5-amine derivatives as multi-target directed ligands for the treatment of Alzheimer's disease.

    abstract::Alzheimer's disease (AD) is associated with multifactorial neuropathological conditions, which include cholinergic deficit, amyloid-beta plaques formation, loss of neuronal plasticity and neuronal death. Treating such multifactorial conditions with a single target directed approach is considered to be inadequate. Acco...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2019.111613

    authors: Gutti G,Kakarla R,Kumar D,Beohar M,Ganeshpurkar A,Kumar A,Krishnamurthy S,Singh SK

    更新日期:2019-11-15 00:00:00

  • Design, synthesis and structure-activity relationships of 4-phenyl-1H-1,2,3-triazole phenylalanine derivatives as novel HIV-1 capsid inhibitors with promising antiviral activities.

    abstract::HIV-1 CA is involved in different stages of the viral replication cycle, performing essential roles in both early (uncoating, reverse transcription, nuclear import, integration) and late events (assembly). Recent efforts have demonstrated HIV-1 CA protein as a prospective therapeutic target for the development of new ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2020.112085

    authors: Sun L,Huang T,Dick A,Meuser ME,Zalloum WA,Chen CH,Ding X,Gao P,Cocklin S,Lee KH,Zhan P,Liu X

    更新日期:2020-03-15 00:00:00

  • Symmetry-based inhibitors of HIV-1 protease. Design, synthesis and preliminary structure-activity studies of acylated 2,3-diamino-1-hydroxypropanes and 2,4 diamino-1-hydroxybutanes.

    abstract::Two series of peptidomimetics containing a novel C(2) pseudosymmetrical hydroxyalkyldiamino core structure were prepared from amino acid starting materials and tested for inhibitory activity against the HIV-1 protease (HIV-1 Pr) and the virus in cell culture. In the 2,3-diamino-1-hydroxypropane series, compound 6a, co...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0223-5234(00)80034-3

    authors: Marastoni M,Bazzaro M,Bortolotti F,Salvadori S,Tomatis R

    更新日期:1999-07-01 00:00:00