Synthesis and biological properties of 4-(3H)-quinazolone derivatives.

Abstract:

:A new quinazolone series has been designed, and synthesized by the anthranilic acid and different acid derivatives. Their structures have been elucidated on the basis of elemental analyses and spectral studies (IR, (1)H NMR, FT-IR and FAB-MS). A preliminary radiolabelling study with technetium has shown a very good future prospect for further evaluation in vivo. The biological activities (antifungal, antibacterial as well as anticancerous) of the evaluated compounds are discussed in this article.

journal_name

Eur J Med Chem

authors

Tiwari AK,Singh VK,Bajpai A,Shukla G,Singh S,Mishra AK

doi

10.1016/j.ejmech.2007.01.002

subject

Has Abstract

pub_date

2007-09-01 00:00:00

pages

1234-8

issue

9

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(07)00035-9

journal_volume

42

pub_type

杂志文章
  • Development of potent dipeptide-type SARS-CoV 3CL protease inhibitors with novel P3 scaffolds: design, synthesis, biological evaluation, and docking studies.

    abstract::We report the design and synthesis of a series of dipeptide-type inhibitors with novel P3 scaffolds that display potent inhibitory activity against SARS-CoV 3CLpro. A docking study involving binding between the dipeptidic lead compound 4 and 3CLpro suggested the modification of a structurally flexible P3 N-(3-methoxyp...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.07.037

    authors: Thanigaimalai P,Konno S,Yamamoto T,Koiwai Y,Taguchi A,Takayama K,Yakushiji F,Akaji K,Chen SE,Naser-Tavakolian A,Schön A,Freire E,Hayashi Y

    更新日期:2013-10-01 00:00:00

  • Development and biological evaluation of[18F]FMN3PA & [18F]FMN3PU for leucine-rich repeat kinase 2 (LRRK2) in vivo PET imaging.

    abstract:PURPOSE:Among all genetic mutations of LRRK2, the G2019S mutation is the most commonly associated with the late-onset of Parkinson's disease (PD). Hence, one potential therapeutic approach is to block the hyperactivity of mutated LRRK2 induced by kinase inhibition. To date, only a few LRRK2 kinase inhibitors have been ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2020.113005

    authors: Malik N,Kornelsen R,McCormick S,Colpo N,Merkens H,Bendre S,Benard F,Sossi V,Schirrmacher R,Schaffer P

    更新日期:2021-02-05 00:00:00

  • Diverse chemical space of indoleamine-2,3-dioxygenase 1 (Ido1) inhibitors.

    abstract::Indoleamine-2,3-dioxygenase 1 (IDO1) catalyses the first and rate limiting step of kynurenine pathway accounting for the major contributor of L-Tryptophan degradation. The Kynurenine metabolites are identified as essential cofactors, antagonists, neurotoxins, immunomodulators, antioxidants as well as carcinogens. The ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2020.113071

    authors: Singh R,Salunke DB

    更新日期:2021-02-05 00:00:00

  • Synthesis and pharmacological properties of a new hydrophilic and orally bioavailable 5-HT4 antagonist.

    abstract::5-HT4 receptor antagonists have been suggested to have clinical potential in treatment of atrial fibrillation, diarrhea-prone irritable bowel syndrome and urinary incontinence. Recently, the use of 5-HT4 antagonists has been suggested to have a therapeutic benefit in heart failure. Affinity for the hERG potassium ion ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.03.060

    authors: Brudeli B,Moltzau LR,Nguyen CH,Andressen KW,Nilsen NO,Levy FO,Klaveness J

    更新日期:2013-06-01 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

  • Pentacyclic triterpene derivatives possessing polyhydroxyl ring A inhibit gram-positive bacteria growth by regulating metabolism and virulence genes expression.

    abstract::The hydroxyl group in ring A of pentacyclic triterpene is essential for antibacterial activity. Pentacyclic triterpenes bearing three hydroxyl groups in ring A were mainly found in plants and displayed significant antibacterial activity. However, no study reported how to obtain this type of compounds by chemical modif...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.01.015

    authors: Huang L,Luo H,Li Q,Wang D,Zhang J,Hao X,Yang X

    更新日期:2015-05-05 00:00:00

  • Synthesis and cytostatic activity of purine nucleosides derivatives of allofuranose.

    abstract::Several new purine nucleosides derivatives of allofuranose were prepared according to Vorbrüggen method, starting from 1,2,5,6-di-O-isopropylidene-α-D-allofuranose and using 1,2,3,5,6-pentaacetoxy-β-D-allofuranose as key intermediate. The synthesized allofuranosyl nucleosides, as well as some acetyl derivatives, were ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2010.09.046

    authors: Besada P,Costas T,Teijeira M,Terán C

    更新日期:2010-12-01 00:00:00

  • Design, synthesis and anticholinesterase activity of novel benzylidenechroman-4-ones bearing cyclic amine side chain.

    abstract::A series of 3-(4-(aminoalkoxy)benzylidene)-chroman-4-ones 7a-r were designed and synthesized as analogs of homoisoflavonoids which are well known natural products with diverse pharmacological properties related to Alzheimer's disease. The in vitro anti-cholinesterase activity of designed compounds 7a-r against AChE an...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.04.055

    authors: Pourshojaei Y,Gouranourimi A,Hekmat S,Asadipour A,Rahmani-Nezhad S,Moradi A,Nadri H,Moghadam FH,Emami S,Foroumadi A,Shafiee A

    更新日期:2015-06-05 00:00:00

  • Structural-activity relationship study on C-4 carbon atom of the CB1 antagonist SR141716: synthesis and pharmacological evaluation of 1,2,4-triazole-3-carboxamides.

    abstract::A series of 1,2,4-triazole-3-carboxamides has been prepared from alkyl-1,2,4-triazole-3-carboxylates under mild conditions. The ability of these triazoles to displace [3H]-CP55940 from CB1 cannabinoid receptor was measured. However, they showed only poor to moderate binding affinities, indicating that substitution of ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2005.06.012

    authors: Jagerovic N,Hernandez-Folgado L,Alkorta I,Goya P,Martín MI,Dannert MT,Alsasua A,Frigola J,Cuberes MR,Dordal A,Holenz J

    更新日期:2006-01-01 00:00:00

  • Heterocyclic pharmacochemistry of new rhinovirus antiviral agents: A combined computational and experimental study.

    abstract::Rhinovirus (RV), member of the Enterovirus genus, is known to be involved in more than half of the common colds. Through advances in molecular biology, rhinoviruses have also been associated with exacerbations of chronic pulmonary diseases (e.g. asthma, chronic obstructive pulmonary disease (COPD) and cystic fibrosis)...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.09.036

    authors: Da Costa L,Scheers E,Coluccia A,Rosetti A,Roche M,Neyts J,Terme T,Cirilli R,Mirabelli C,Silvestri R,Vanelle P

    更新日期:2017-11-10 00:00:00

  • (Arene)Ru(II) complexes of epidermal growth factor receptor inhibiting tyrphostins with enhanced selectivity and cytotoxicity in cancer cells.

    abstract::Ru(eta6-arene) complexes of epidermal growth factor receptor (EGFR) inhibiting tyrphostins 1a and 1b were prepared, characterized and tested for DNA interaction and bioactivity in four human tumor cell lines. The intrinsic cytotoxicity and cell line selectivity of o-hydroxyanisol 1a was greatly enhanced in its Ru(eta6...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2010.01.040

    authors: Biersack B,Zoldakova M,Effenberger K,Schobert R

    更新日期:2010-05-01 00:00:00

  • Synthesis, molecular docking and biological evaluation of novel phthaloyl derivatives of 3-amino-3-aryl propionic acids as inhibitors of Trypanosoma cruzi trans-sialidase.

    abstract::In the last two decades, trans-sialidase of Trypanosoma cruzi (TcTS) has been an important pharmacological target for developing new anti-Chagas agents. In a continuous effort to discover new potential TcTS inhibitors, 3-amino-3-arylpropionic acid derivatives (series A) and novel phthaloyl derivatives (series B, C and...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.07.005

    authors: Kashif M,Chacón-Vargas KF,López-Cedillo JC,Nogueda-Torres B,Paz-González AD,Ramírez-Moreno E,Agusti R,Uhrig ML,Reyes-Arellano A,Peralta-Cruz J,Ashfaq M,Rivera G

    更新日期:2018-08-05 00:00:00

  • Xanthine oxidase inhibitors beyond allopurinol and febuxostat; an overview and selection of potential leads based on in silico calculated physico-chemical properties, predicted pharmacokinetics and toxicity.

    abstract::Xanthine oxidase (XO), a versatile metalloflavoprotein enzyme, catalyzes the oxidative hydroxylation of hypoxanthine and xanthine to uric acid in purine catabolism while simultaneously producing reactive oxygen species. Both lead to the gout-causing hyperuricemia and oxidative damage of the tissues where overactivity ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2017.04.031

    authors: Šmelcerović A,Tomović K,Šmelcerović Ž,Petronijević Ž,Kocić G,Tomašič T,Jakopin Ž,Anderluh M

    更新日期:2017-07-28 00:00:00

  • Spirostanols obtained by cyclization of pseudosaponin derivatives and comparison of anti-platelet agglutination activities of spirostanol glycosides.

    abstract::Naturally occurring saponins 3 and 4 have a normal type F ring and alpha-arranged CH(3)-21 group. Treatments of pseudosaponin peracetates 18 and 19 derived from 3 and 4, respectively, with alcoholic KOH, followed by acidification with acetic acid, gave spirostanols 20 and 22 having iso type F rings as major products. ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0223-5234(00)00151-3

    authors: Tobari A,Teshima M,Koyanagi J,Kawase M,Miyamae H,Yoza K,Takasaki A,Nagamura Y,Saito S

    更新日期:2000-05-01 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

  • Synthesis and structure-activity relationships of guaiane-type sesquiterpene lactone derivatives with respect to inhibiting NO production in lipopolysaccharide-induced RAW 264.7 macrophages.

    abstract::A guaiane framework was scaffolded by photochemical rearrangement reactions using α-santonin 1 as a starting material. Then, using a series of reactions, we synthesized the guaiane-type sesquiterpene lactone 5 in high yield. The inhibitory activities of compound 5 and of a series of derivatives on nitric oxide (NO) re...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.06.043

    authors: Chen H,Chen BY,Liu CT,Zhao Z,Shao WH,Yuan H,Bi KJ,Liu JY,Sun QY,Zhang WD

    更新日期:2014-08-18 00:00:00

  • Molecular diversity of trimethoxyphenyl-1,2,3-triazole hybrids as novel colchicine site tubulin polymerization inhibitors.

    abstract::Structurally diverse trimethoxyphenyl-1,2,3-triazole hybrids were designed, synthesized and evaluated for their antiproliferative activity against three cancer cell lines (PC3, MGC803 and HepG2). Among them, trimethoxyphenyl-1,2,3-triazole containing the coumarin fragement 19c displayed better antiproliferative activi...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2019.01.033

    authors: Fu DJ,Li P,Wu BW,Cui XX,Zhao CB,Zhang SY

    更新日期:2019-03-01 00:00:00

  • Structure-activity studies on N-Substituted tranylcypromine derivatives lead to selective inhibitors of lysine specific demethylase 1 (LSD1) and potent inducers of leukemic cell differentiation.

    abstract::FAD-dependent lysine-specific demethylase 1 (LSD1) is overexpressed or deregulated in many cancers such as AML and prostate cancer and hence is a promising anticancer target with first inhibitors in clinical trials. Clinical candidates are N-substituted derivatives of the dual LSD1-/monoamine oxidase-inhibitor tranylc...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.12.001

    authors: Schulz-Fincke J,Hau M,Barth J,Robaa D,Willmann D,Kürner A,Haas J,Greve G,Haydn T,Fulda S,Lübbert M,Lüdeke S,Berg T,Sippl W,Schüle R,Jung M

    更新日期:2018-01-20 00:00:00

  • Design, synthesis and biological activities of novel oxazolo[4,5-g]quinazolin-2(1H)-one derivatives as EGFR inhibitors.

    abstract::A series of oxazolo[4,5-g]quinazolin-2(1H)-one derivatives employing Erlotinib as lead compound were synthesized and evaluated for their EGFR inhibition activity. These compounds having variation at the 1 and 8-position, included ether and esters hydrophilic side-chain and aromatic head fragment, respectively. All the...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.07.008

    authors: Yin S,Zhou L,Lin J,Xue L,Zhang C

    更新日期:2015-08-28 00:00:00

  • Repurposed drug candidates for antituberculosis therapy.

    abstract::Antibiotics have been a key part of clinical treatments for more than 70 years. Long-term use of antimicrobial treatments has led to the development of severe bacterial resistance, which has become increasingly serious due to antibiotic abuse, resulting in the treatment of bacterial infections becoming challenging. Th...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2020.112175

    authors: An Q,Li C,Chen Y,Deng Y,Yang T,Luo Y

    更新日期:2020-04-15 00:00:00

  • Synthesis and antitumor activities of naturally occurring oleanolic acid triterpenoid saponins and their derivatives.

    abstract::Twenty-six naturally occurring oleanolic acid saponins and their derivatives, 16 of which were synthesized in this study, were preliminarily evaluated against human cancer cells. From SAR studies, the presence of α-l-rhamnosyl residue at the terminal of both C-3 and C-28 position for oleanolic acid bidesmosides was im...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.04.016

    authors: Liu Q,Liu H,Zhang L,Guo T,Wang P,Geng M,Li Y

    更新日期:2013-06-01 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

  • Structure-based discovery of selective BRPF1 bromodomain inhibitors.

    abstract::Bromodomain and plant homeodomain (PHD) finger containing protein 1 (BRPF1) is a member of subfamily IV of the human bromodomains. Experimental evidence suggests that BRPF1 is involved in leukemia. In a previous high-throughput docking campaign we identified several chemotypes targeting the BRPF1 bromodomain. Here, ph...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.05.037

    authors: Zhu J,Zhou C,Caflisch A

    更新日期:2018-07-15 00:00:00

  • Asymmetric 1,5-diarylpenta-1,4-dien-3-ones: Antiproliferative activity in prostate epithelial cell models and pharmacokinetic studies.

    abstract::To further engineer dienones with optimal combinations of potency and bioavailability, thirty-four asymmetric 1,5-diarylpenta-1,4-dien-3-ones (25-58) have been designed and synthesized for the evaluation of their in vitro anti-proliferative activity in three human prostate cancer cell lines and one non-neoplastic pros...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.05.062

    authors: Zhang X,Guo S,Chen C,Perez GR,Zhang C,Patanapongpibul M,Subrahmanyam N,Wang R,Keith J,Chen G,Dong Y,Zhang Q,Zhong Q,Zheng S,Wang G,Chen QH

    更新日期:2017-09-08 00:00:00

  • Synthesis of N-substituted acyclic β-amino acids and their investigation as GABA uptake inhibitors.

    abstract::In this publication, we describe the synthesis of new inhibitors for the GABA transporter subtypes GAT1 and especially GAT3. We started with 3-aminopropanoic acid possessing a distinct preference for GAT3 in comparison to GAT1 and furthermore its homolog 3-aminobutanoic acid. A series of respective N-substituted amino...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.04.063

    authors: Sitka I,Allmendinger L,Fülep G,Höfner G,Wanner KT

    更新日期:2013-07-01 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

  • Synthesis and biological activity of polyalthenol and pentacyclindole analogues.

    abstract::A series of indole sesquiterpenes analogues of polyalthenol and pentacyclindole have been synthesized starting from ent-halimic acid in order to test their biological activity. These analogues include diverse oxidation levels at the sesquiterpenyl moiety and different functionalization on the indole ring. All syntheti...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.12.012

    authors: Marcos IS,Moro RF,Costales I,Basabe P,Díez D,Gil A,Mollinedo F,Pérez-de la Rosa F,Pérez-Roth E,Padrón JM

    更新日期:2014-02-12 00:00:00

  • Reversal of P-gp and BCRP-mediated MDR by tariquidar derivatives.

    abstract::With an aim to generate non-toxic, specific and highly potent multidrug resistance (MDR) modulators, a novel series of anthranilic acid amide-substituted tariquidar derivatives were synthesized. The new compounds were evaluated for their cytotoxicity toward normal human colon fibroblasts (CCD18-Co), human gastric epit...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.06.049

    authors: Li XQ,Wang L,Lei Y,Hu T,Zhang FL,Cho CH,To KK

    更新日期:2015-08-28 00:00:00

  • Optimization of a pharmacophore model for 5-HT4 agonists using CoMFA and receptor based alignment.

    abstract::Twenty two 5-HT4 agonists obtained from our laboratory and the recent literature were used to develop a CoMFA model to predict 5-HT4 agonist activity. Two models were produced and compared for predictivity, the first by alignments based on atom overlapping (model A) and the second by adding agonist binding site intera...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2005.07.017

    authors: Iskander MN,Leung LM,Buley T,Ayad F,Di Iulio J,Tan YY,Coupar IM

    更新日期:2006-01-01 00:00:00

  • The optimization of xanthine derivatives leading to HBK001 hydrochloride as a potent dual ligand targeting DPP-IV and GPR119.

    abstract::A series of xanthine compounds derived from the previous hit 20i with modification on the terminal side chain was discovered through ring formation strategy. Systematic optimization of the compounds with rigid heterocycles in the hydrophobic side chain led to the new lead compound HBK001 (21h) with the improved DPP-IV...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2019.112017

    authors: Li G,Meng B,Yuan B,Huan Y,Zhou T,Jiang Q,Lei L,Sheng L,Wang W,Gong N,Lu Y,Ma C,Li Y,Shen Z,Huang H

    更新日期:2020-02-15 00:00:00