Synthesis, molecular docking and anti-mycobacterial evaluation of new imidazo[1,2-a]pyridine-2-carboxamide derivatives.

Abstract:

:New anti-tubercular agents, imidazo[1,2-a]pyridine-2-carboxamide derivatives (5a-q) have been designed and synthesized. The structural considerations of the designed molecules were further supported by the docking study with a long-chain enoyl-acyl carrier protein reductase (InhA). The chemical structures of the new compounds were characterized by IR, (1)H NMR, (13)C NMR, HRMS and elemental analysis. In addition, single crystal X-ray diffraction has also been recorded for compound 5f. Compounds were evaluated in vitro against Mycobacterium tuberculosis H37Rv, and cytotoxicity against HEK-293T cell line. Amongst the tested compounds 5j, 5l and 5q were emerged as good anti-tubercular agents with low cytotoxicity. The structure-anti TB activity relationship of these derivatives was explained by molecular docking.

journal_name

Eur J Med Chem

authors

Jose G,Suresha Kumara TH,Nagendrappa G,Sowmya HB,Sriram D,Yogeeswari P,Sridevi JP,Guru Row TN,Hosamani AA,Sujan Ganapathy PS,Chandrika N,Narendra LV

doi

10.1016/j.ejmech.2014.10.079

subject

Has Abstract

pub_date

2015-01-07 00:00:00

pages

616-27

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(14)01015-0

journal_volume

89

pub_type

杂志文章
  • Angiotensin II--AT1 receptor antagonists: design, synthesis and evaluation of substituted carboxamido benzimidazole derivatives.

    abstract::A series of 5-(alkyl and aryl)carboxamido benzimidazole derivatives had been designed, synthesized and evaluated for in vitro angiotensin II--AT1 receptor antagonism and in vivo antihypertensive activities. The pharmacological activities were inversely related to the size of alkyl and aryl substituents. It can be sugg...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2007.11.008

    authors: Shah DI,Sharma M,Bansal Y,Bansal G,Singh M

    更新日期:2008-09-01 00:00:00

  • Evaluation of potential Myt1 kinase inhibitors by TR-FRET based binding assay.

    abstract::In the human cell cycle, the Myt1 kinase is a crucial regulator of the G2/M transition. Because this membrane-associated kinase is hard to obtain and assay, there is a distinct lack of data so far. Here we report the derivatization of a glycoglycerolipid which was shown previously to be active in a Myt1 activity assay...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2012.06.007

    authors: Rohe A,Göllner C,Wichapong K,Erdmann F,Al-Mazaideh GM,Sippl W,Schmidt M

    更新日期:2013-03-01 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

  • Synthesis, biological evaluation and 3D QSAR study of 2,4-disubstituted quinolines as anti-tuberculosis agents.

    abstract::The synthesis and anti-tuberculosis activity for three series of 2,4-disubstituted quinolines is reported. The synthesized compounds were evaluated for activity against M. tuberculosis H37Rv strain; most promising compounds from the series exhibited MIC99 values ranged between 3.125 and 6.25 μg/mL. None of the compoun...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.02.034

    authors: Patel SR,Gangwal R,Sangamwar AT,Jain R

    更新日期:2015-03-26 00:00:00

  • Fluorinated polymer emulsion systems: Construction and application in delivering genes and proteins.

    abstract::Emulsions have shown great potential in the delivery of various types of cargoes such as nucleic acids and proteins. In this study, fluorinated polymer emulsions (PFx@PFD-n) were prepared using fluorinated polymers with different structures as surfactant in PFD emulsions under ultrasound. These polymer emulsions gave ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2020.112799

    authors: Xiao YP,Zhang J,Liu YH,Huang Z,Yu XQ

    更新日期:2020-12-01 00:00:00

  • Synthesis and comparative photodynamic properties of two isosteric alkyl substituted zinc(II) phthalocyanines.

    abstract::The synthesis and photophysical parameters of two novel isosteric cationic zinc(II) phthalocyanines: 2,9(10),16(17),23(24)-tetrakis[(N-butyl-N-methylammoniumethylsulfanyl]phthalocyaninatozinc(II) tetraiodide (6) and 2,9(10),16(17),23(24)-tetrakis[(N-dibutyl-N-methylammonium)ethoxy]phthalocyaninatozinc(II) tetraiodide ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.09.014

    authors: Gauna GA,Marino J,García Vior MC,Roguin LP,Awruch J

    更新日期:2011-11-01 00:00:00

  • Synthesis and biological evaluation of a novel series of 1,5-benzothiazepine derivatives as potential antimicrobial agents.

    abstract::Two series of novel 1,5-benzothiazepine derivatives (23 compounds) were efficiently synthesized and evaluated for antibacterial and antifungal activities. The results indicated that the compounds possessed a broad spectrum of activity against the tested microorganisms and showed higher activity against fungi than bact...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2008.12.021

    authors: Wang L,Zhang P,Zhang X,Zhang Y,Li Y,Wang Y

    更新日期:2009-07-01 00:00:00

  • Stereoselective synthesis and biological evaluation of (R)-rugulactone, (6R)-((4R)-hydroxy-6-phenyl-hex-2-enyl)-5,6-dihydro-pyran-2-one and its 4S epimer.

    abstract::A simple and highly efficient synthetic route has been developed for synthesis of (R)-rugulactone (1a), (6R)-((4R)-hydroxy-6-phenyl-hex-2-enyl)-5,6-dihydro-pyran-2-one (1b) and its 4S epimer 1c by employing proline-catalyzed alpha-aminooxylation, Sharpless epoxidation, Mitsunobu reaction as chirality introuducing step...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2010.07.036

    authors: Reddy DK,Shekhar V,Prabhakar P,Chinna Babu B,Siddhardha B,Murthy US,Venkateswarlu Y

    更新日期:2010-10-01 00:00:00

  • Comparative chemometric modeling of cytochrome 3A4 inhibitory activity of structurally diverse compounds using stepwise MLR, FA-MLR, PLS, GFA, G/PLS and ANN techniques.

    abstract::Twenty-eight structurally diverse cytochrome 3A4 (CYP3A4) inhibitors have been subjected to quantitative structure-activity relationship (QSAR) studies. The analyses were performed with electronic, spatial, topological, and thermodynamic descriptors calculated using Cerius 2 version 10 software. The statistical tools ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2008.12.004

    authors: Roy K,Pratim Roy P

    更新日期:2009-07-01 00:00:00

  • Synthesis and antitrypanosomal evaluation of E-isomers of 5-nitro-2-furaldehyde and 5-nitrothiophene-2-carboxaldehyde semicarbazone derivatives. structure-activity relationships.

    abstract::Several novel semicarbazone derivatives were prepared from 5-nitro-2-furaldehyde or 5-nitrothiophene-2-carboxaldehyde and semicarbazides bearing a spermidine-mimetic moiety. All derivatives presented the E-configuration, as determined by NMR-NOE experiments. These compounds were tested in vitro as potential antitrypan...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0223-5234(00)00131-8

    authors: Cerecetto H,Di Maio R,González M,Risso M,Sagrera G,Seoane G,Denicola A,Peluffo G,Quijano C,Stoppani AO,Paulino M,Olea-Azar C,Basombrío MA

    更新日期:2000-03-01 00:00:00

  • Synthesis, biological evaluation, and molecular docking study of 3-(3'-heteroatom substituted-2'-hydroxy-1'-propyloxy) xanthone analogues as novel topoisomerase IIα catalytic inhibitor.

    abstract::Epoxide ring-opened xanthone derivatives were synthesized and tested for their topoisomerase inhibitory activity and cytotoxicity. Most of the compounds showed topo IIα specific inhibitory activity. To clarify the mechanism of action of these compounds, the most potent compound (compound 14) of the synthesized analogu...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.01.011

    authors: Jun KY,Lee EY,Jung MJ,Lee OH,Lee ES,Park Choo HY,Na Y,Kwon Y

    更新日期:2011-06-01 00:00:00

  • Alkoxyphenylthiazoles with broad-spectrum activity against multidrug-resistant gram-positive bacterial pathogens.

    abstract::With the continued rise of antibiotic resistance and reduced susceptibility to almost all front-line antibiotics, multidrug-resistant Gram-positive bacterial infections represent an incessant threat to healthcare providers. This study presents a new series of phenylthiazole compounds where two active moieties were com...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.04.049

    authors: ElAwamy M,Mohammad H,Hussien A,Abutaleb NS,Hagras M,Serya RAT,Taher AT,Abouzid KA,Seleem MN,Mayhoub AS

    更新日期:2018-05-25 00:00:00

  • 3-Pyrazolone analogues of the 3-isoxazolol metabotropic excitatory amino acid receptor agonist homo-AMPA. Synthesis and pharmacological testing.

    abstract::We have previously shown that the higher homologue of (S)-glutamic acid [(S)-Glu], (S)-alpha-aminoadipic acid [(S)-alpha-AA] is selectively recognized by the mGlu(2) and mGlu(6) subtypes of the family of metabotropic glutamic acid (mGlu) receptors. Furthermore, a number of analogues of (S)-alpha-AA, in which the termi...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0223-5234(99)00122-1

    authors: Zimmermann D,Janin YL,Brehm L,Bräuner-Osborne H,Ebert B,Johansen TN,Madsen U,Krogsgaard-Larsen P

    更新日期:1999-11-01 00:00:00

  • Design, synthesis and hypolipidemic activity of novel 2-(m-tolyloxy) isobutyric acid derivatives.

    abstract::Novel 2-substituted isobutyric acid derivatives were synthesized and their hypolipidemic activity was evaluated in high cholesterol diet fed rat model. The amide 5a was found to decrease the levels of serum total cholesterol, LDL cholesterol and triglycerides in hyperlipidemic rats to a greater degree than the referen...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2008.12.009

    authors: Idrees GA,Abuo-Rahma Gel-D,Aly OM,Radwan MF

    更新日期:2009-06-01 00:00:00

  • Synthesis and blood glucose lowering effect of novel pyridazinone substituted benzenesulfonylurea derivatives.

    abstract::Fifteen novel pyridazinone substituted benzenesulfonylurea derivatives (3a-o) were synthesized from corresponding sulfonamides derivatives via novel carbamates (2a-e). These were characterized by elemental analysis and various spectroscopic methods viz. IR, (1)H NMR, (13)C NMR and MS. Blood sugar lowering effect of th...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2008.12.013

    authors: Rathish IG,Javed K,Bano S,Ahmad S,Alam MS,Pillai KK

    更新日期:2009-06-01 00:00:00

  • Synthesis and biological evaluation of novel 2-arylamino-3-(arylsulfonyl)quinoxalines as PI3Kα inhibitors.

    abstract::A series of novel 2-arylamino-3-(arylsulfonyl)quinoxalines was synthesized through a newly developed approach. All synthesized target compounds were screened for their cytotoxicities against cancer cell lines including PC3, A549, HCT116, HL60 and KB. Representative compounds with favorable cytotoxicities were tested f...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.09.015

    authors: Wu P,Su Y,Liu X,Zhang L,Ye Y,Xu J,Weng S,Li Y,Liu T,Huang S,Yang B,He Q,Hu Y

    更新日期:2011-11-01 00:00:00

  • pH and reduction dual-responsive dipeptide cationic lipids with α-tocopherol hydrophobic tail for efficient gene delivery.

    abstract::A series of tocopherol-based cationic lipid 3a-3f bearing a pH-sensitive imidazole moiety in the dipeptide headgroup and a reduction-responsive disulfide linkage were designed and synthesized. Acid-base titration of these lipids showed good buffering capacities. The liposomes formed from 3 and co-lipid 1, 2-dioleoyl-s...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.02.010

    authors: Liu Q,Su RC,Yi WJ,Zheng LT,Lu SS,Zhao ZG

    更新日期:2017-03-31 00:00:00

  • Structure-activity relationship study of peptidomimetic aldehydes as enterovirus 71 3C protease inhibitors.

    abstract::A series of peptidomimetic aldehydes were designed, synthesized, and evaluated for their biochemical activity against 3C protease (3Cpro) and anti-enterovirus 71 (EV71) activity in vitro. Molecular docking revealed that 5s (IC50 = 0.22 ± 0.07 μM, EC50 = 0.18 ± 0.05 μM) could bind well to the active site of EV71 3Cpro,...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2016.08.064

    authors: Zhai Y,Ma Y,Ma F,Nie Q,Ren X,Wang Y,Shang L,Yin Z

    更新日期:2016-11-29 00:00:00

  • Imidazo[2,1-b]thiazole guanylhydrazones as RSK2 inhibitors.

    abstract::The activity of a series of imidazo[2,1-b]thiazole guanylhydrazones as inhibitors of p90 ribosomal S6 kinase 2 (RSK2) is described. It was found that a small subset of compounds show both potent inhibition of RSK2 kinase activity and tumor cell growth in vitro. Detailed study of one of the most active compounds indica...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.07.001

    authors: Andreani A,Granaiola M,Leoni A,Locatelli A,Morigi R,Rambaldi M,Varoli L,Lannigan D,Smith J,Scudiero D,Kondapaka S,Shoemaker RH

    更新日期:2011-09-01 00:00:00

  • Synthesis and in vitro anticancer activity evaluation of novel bioreversible phosphate inositol derivatives.

    abstract::The chemistry and biology of phosphorylated inositols have become intense areas of research during the last two decades due to their involvement in various cellular signaling processes. However, the metabolic instability by phosphatases or kinases and poor penetration make it difficult to become a drug used in the cli...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.01.064

    authors: Chen W,Deng Z,Chen K,Dou D,Song F,Li L,Xi Z

    更新日期:2015-03-26 00:00:00

  • Design and synthesis of novel SCM-198 analogs as cardioprotective agents: Structure-activity relationship studies and biological evaluations.

    abstract::SCM-198 (Leonurine) has attracted great attention due to its cardioprotective effects in myocardial infarction (MI). However, no systematic modifications and structure-activity relationship (SAR) studies could be traced so far. In this study, 35 analogs of SCM-198 were designed, synthesized and their cardioprotective ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2020.112469

    authors: Luo S,Xu S,Liu J,Ma F,Zhu YZ

    更新日期:2020-08-15 00:00:00

  • A novel series of 6-substituted 3-(pyrrolidin-1-ylmethyl)chromen-2-ones as selective monoamine oxidase (MAO) A inhibitors.

    abstract::A series of 6-substituted 3-(pyrrolidin-1-ylmethyl)chromen-2-ones (coumarins) have been synthesized and their inhibitory activity to human monoamine oxidase A (MAO A) and B (MAO B) determined. Incorporation of a basic amino function in the C3 position together with substitution at the C6 position produced novel coumar...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.11.035

    authors: Mattsson C,Svensson P,Sonesson C

    更新日期:2014-02-12 00:00:00

  • Synthesis, anticancer activity and effects on cell cycle profile and apoptosis of novel thieno[2,3-d]pyrimidine and thieno[3,2-e] triazolo[4,3-c]pyrimidine derivatives.

    abstract::Motivated by the widely reported anticancer activity of thieno[2,3-d]pyrimidines a series of 24 new 2-substitutedhexahydrocycloocta[4,5] thieno[2,3-d]pyrimidines with different substituents at C-4 position and hexahydrocycloocta[4,5]thieno[3,2-e]-1,2,4-triazolo[4,3-c]pyrimidines were synthesized. The anticancer activi...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.12.009

    authors: Kandeel MM,Refaat HM,Kassab AE,Shahin IG,Abdelghany TM

    更新日期:2015-01-27 00:00:00

  • Second-generation sulfonamide inhibitors of D-glutamic acid-adding enzyme: activity optimisation with conformationally rigid analogues of D-glutamic acid.

    abstract::D-Glutamic acid-adding enzyme (MurD) catalyses the essential addition of d-glutamic acid to the cytoplasmic peptidoglycan precursor UDP-N-acetylmuramoyl-l-alanine, and as such it represents an important antibacterial drug-discovery target enzyme. Based on a series of naphthalene-N-sulfonyl-d-Glu derivatives synthesise...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.04.011

    authors: Sosič I,Barreteau H,Simčič M,Sink R,Cesar J,Zega A,Grdadolnik SG,Contreras-Martel C,Dessen A,Amoroso A,Joris B,Blanot D,Gobec S

    更新日期:2011-07-01 00:00:00

  • A comparative study of the hydrolysis pathways of substituted aryl phosphoramidate versus aryl thiophosphoramidate derivatives of stavudine.

    abstract::A comparative study of aryl phosphoramidate and aryl thiophosphoramidate derivatives of 2',3'-didehydro-2',3'-dideoxythymidine (d4T) was performed. The study focused on the nature of the substituents and the influence of a thiophosphoramidate in the structure of these derivatives. The rate of alkaline hydrolysis of th...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2004.04.002

    authors: Venkatachalam TK,Yu G,Samuel P,Qazi S,Pendergrass S,Uckun FM

    更新日期:2004-08-01 00:00:00

  • Anticonvulsant activity, crystal structures, and preliminary safety evaluation of N-trans-cinnamoyl derivatives of selected (un)modified aminoalkanols.

    abstract::Adequate control of seizures remains an unmet need in epilepsy. In order to identify new anticonvulsant agents, a series of N-trans-cinnamoyl derivatives of selected aminoalkanols was synthetized. The compounds were obtained in the reaction of N-acylation carried out in a two-phase system. The substances were tested i...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.10.051

    authors: Gunia-Krzyżak A,Żesławska E,Słoczyńska K,Koczurkiewicz P,Nitek W,Żelaszczyk D,Szkaradek N,Waszkielewicz AM,Pękala E,Marona H

    更新日期:2016-01-01 00:00:00

  • Organoiodine (III)-mediated synthesis of 3-aryl/heteroaryl-5,7-dimethyl-1,2,4-triazolo[4,3-c]pyrimidines as antibacterial agents.

    abstract::Synthesis of 12 new 3-aryl/heteroaryl-5,7-dimethyl-1,2,4-triazolo[4,3-c]pyrimidines (3a-l) has been accomplished by the oxidation of pyrimidinylhydrazones (2a-l) of various aryl/heteroaryl aldehydes using 1.1equiv. of iodobenzene diacetate (IBD) in dichloromethane. All the compounds 3a-l tested in vitro for their anti...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2008.06.004

    authors: Kumar R,Nair RR,Dhiman SS,Sharma J,Prakash O

    更新日期:2009-05-01 00:00:00

  • Sesquiterpene lactones from Inula falconeri, a plant endemic to the Himalayas, as potential anti-inflammatory agents.

    abstract::A phytochemical investigation of Inula falconeri, a plant endemic to the Himalayas, afforded 10 new sesquiterpenoids and 26 known sesquiterpene lactones, including those bearing guaiane, pseudoguaiane, xanthane, eudesmane, germacrane, rare secocaryophyllane, chromolaevane, and carabrane frameworks. The structures were...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.08.047

    authors: Cheng X,Zeng Q,Ren J,Qin J,Zhang S,Shen Y,Zhu J,Zhang F,Chang R,Zhu Y,Zhang W,Jin H

    更新日期:2011-11-01 00:00:00

  • Discovery of a benzenesulfonamide-based dual inhibitor of microsomal prostaglandin E2 synthase-1 and 5-lipoxygenase that favorably modulates lipid mediator biosynthesis in inflammation.

    abstract::Leukotrienes (LTs) and prostaglandin (PG)E2, produced by 5-lipoxygenase (5-LO) and microsomal prostaglandin E2 synthase-1 (mPGES-1), respectively, are key players in inflammation, and pharmacological suppression of these lipid mediators (LM) represents a strategy to intervene with inflammatory disorders. Previous stud...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.07.031

    authors: Cheung SY,Werner M,Esposito L,Troisi F,Cantone V,Liening S,König S,Gerstmeier J,Koeberle A,Bilancia R,Rizza R,Rossi A,Roviezzo F,Temml V,Schuster D,Stuppner H,Schubert-Zsilavecz M,Werz O,Hanke T,Pace S

    更新日期:2018-08-05 00:00:00

  • Synthesis and antiprotozoal activities of simplified analogs of naphthylisoquinoline alkaloids.

    abstract::The naphthylisoquinoline alkaloids (NIQs) represent a class of natural products with manifold activities against various tropical diseases. They are isolated from rare and difficult-to-cultivate tropical plants. In order to find novel, more easily accessible analogs and to study structure-activity relationships, a var...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2007.03.003

    authors: Bringmann G,Brun R,Kaiser M,Neumann S

    更新日期:2008-01-01 00:00:00