Synthesis and biological screening of 2'-aryl/benzyl-2-aryl-4-methyl-4',5-bithiazolyls as possible anti-tubercular and antimicrobial agents.

Abstract:

:A series of 2'-aryl/benzyl-2-aryl-4-methyl-4',5-bithiazolyl derivatives, 25-64 were synthesized and evaluated for inhibitory activity against Mycobacterium smegmatis MC(2) 155 strain and antimicrobial activities against four pathogenic bacteria Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Proteus vulgaris. Among them, compounds 40, 49, 50, and 54 exhibited moderate to good inhibition on the growth of the bacteria Mycobacterium smegmatis at the concentration of 30 μM. Compounds 26, 40, 44, 54 and 56 exhibited moderate to good antibacterial activity. Compound 5-(2'-(4-fluorobenzyl)thiazol-4'-yl)-2-(4-fluorophenyl)-4-methyl-thiazole (54) exhibited both antitubercular as well as antimicrobial activity against all tested strains.

journal_name

Eur J Med Chem

authors

Abhale YK,Sasane AV,Chavan AP,Deshmukh KK,Kotapalli SS,Ummanni R,Sayyad SF,Mhaske PC

doi

10.1016/j.ejmech.2015.03.016

subject

Has Abstract

pub_date

2015-04-13 00:00:00

pages

340-7

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(15)00183-X

journal_volume

94

pub_type

杂志文章
  • Synthesis, brain antihypoxic activity and cell neuroprotection of 1-substituted-3,7-dimethylxanthines.

    abstract::Five newly synthesised original compounds were investigated for acute toxicity, influence on hexobarbital sleeping time, effect on the locomotor activity, and brain antihypoxic activity. Two of the compounds were tested in a model of glutamate induced neurotoxicity in the brain cell culture using a cell viability test...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0223-5234(00)01172-7

    authors: Zlatkov A,Peikov P,Rodriguez-Alvarez J,Danchev N,Nikolova I,Mitkov J

    更新日期:2000-10-01 00:00:00

  • Design and synthesis of a C7-aryl piperlongumine derivative with potent antimicrotubule and mutant p53-reactivating properties.

    abstract::Small molecules that can restore biological function to the p53 mutants found in human cancers have been highly sought to increase the anticancer efficacy. In efforts to generate hybrid anticancer drugs that can impact two or more targets simultaneously, we designed and developed piperlongumine (PL) derivatives with a...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.10.052

    authors: Punganuru SR,Madala HR,Venugopal SN,Samala R,Mikelis C,Srivenugopal KS

    更新日期:2016-01-01 00:00:00

  • Design, synthesis and screening of 1, 2, 4-triazinone derivatives as potential antitumor agents with apoptosis inducing activity on MCF-7 breast cancer cell line.

    abstract::Some triazinone derivatives are designed and synthesized as potential antitumor agents. Triazinone derivatives 4c, 5e and 7c show potent anticancer activity over MCF-7 breast cancer cells higher than podophyllotoxin (podo) by approximate 6-fold. DNA flow cytometry analysis for the compounds 3c, 4c, 5e, 6c and 7c show ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.07.003

    authors: Zaki I,Abdelhameid MK,El-Deen IM,Abdel Wahab AHA,Ashmawy AM,Mohamed KO

    更新日期:2018-08-05 00:00:00

  • Novel imidazole derivatives as heme oxygenase-1 (HO-1) and heme oxygenase-2 (HO-2) inhibitors and their cytotoxic activity in human-derived cancer cell lines.

    abstract::Heme oxygenase (HO) is a cytoprotective enzyme that can be overexpressed in some pathological conditions, including certain cancers. In this work, novel imidazole derivatives were designed and synthesized as inhibitors of heme oxygenase-1 (HO-1) and heme oxygenase-2 (HO-2). In these compounds the imidazole ring, cruci...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.04.003

    authors: Salerno L,Pittalà V,Romeo G,Modica MN,Marrazzo A,Siracusa MA,Sorrenti V,Di Giacomo C,Vanella L,Parayath NN,Greish K

    更新日期:2015-01-01 00:00:00

  • Heterocyclic analogs of benzanilide derivatives as potassium channel activators. IX.

    abstract::On the basis of our previous works, addressed to synthesise new activators of BK potassium channels, and of many suggestions from the international literature, a simple pharmacophoric model, consisting of two suitably substituted phenyl rings bound to various kinds of linkers, was hypothesised. In particular, the effe...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2006.03.009

    authors: Calderone V,Fiamingo FL,Giorgi I,Leonardi M,Livi O,Martelli A,Martinotti E

    更新日期:2006-06-01 00:00:00

  • Design, synthesis and anti-mycobacterial activity of 1,2,3,5-tetrasubstituted pyrrolyl-N-acetic acid derivatives.

    abstract::A novel synthesis of highly substituted pyrrole-N-acetic derivatives is described through the coupling of 1,4-diketones with amino acids following Paal-Knorr's approach. These pyrrole-N-acetic acid derivatives are found to exhibit potent anti-mycobacterial activity against Mycobacterium smegmatis and Mycobacterium tub...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.06.075

    authors: Pagadala LR,Mukkara LD,Singireddi S,Singh A,Thummaluru VR,Jagarlamudi PS,Guttala RS,Perumal Y,Dharmarajan S,Upadhyayula SM,Ummanni R,Basireddy VS,Ravirala N

    更新日期:2014-09-12 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

  • Structure-activity analysis of CJ-15,801 analogues that interact with Plasmodium falciparum pantothenate kinase and inhibit parasite proliferation.

    abstract::Survival of the human malaria parasite Plasmodium falciparum is dependent on pantothenate (vitamin B5), a precursor of the fundamental enzyme cofactor coenzyme A. CJ-15,801, an enamide analogue of pantothenate isolated from the fungus Seimatosporium sp. CL28611, was previously shown to inhibit P. falciparum proliferat...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2017.08.050

    authors: Spry C,Sewell AL,Hering Y,Villa MVJ,Weber J,Hobson SJ,Harnor SJ,Gul S,Marquez R,Saliba KJ

    更新日期:2018-01-01 00:00:00

  • Synthesis and in vitro stability of nucleoside 5'-phosphonate derivatives.

    abstract::Nucleoside derivatives are largely synthesized and tested to investigate their influence on platelet aggregation. It's well known that P2Y receptors play an important role in the regulation of platelet function and, as consequence, in controlling atherothrombotic events. The research of compounds that antagonize P2Y(1...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2012.04.045

    authors: Vertuani S,Baldisserotto A,Varani K,Borea PA,De Marcos Maria Cruz B,Ferraro L,Manfredini S,Dalpiaz A

    更新日期:2012-08-01 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

  • 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

  • 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

  • An overview on crystal structures of InhA protein: Apo-form, in complex with its natural ligands and inhibitors.

    abstract::The enoyl-ACP reductase InhA from the mycobacterial fatty acid biosynthesis pathway has become a target of interest for the development of new anti-tubercular drugs. This protein has been identified as essential for the survival of Mycobacterium tuberculosis, the causative agent of tuberculosis, and as the main target...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2018.01.047

    authors: Chollet A,Maveyraud L,Lherbet C,Bernardes-Génisson V

    更新日期:2018-02-25 00:00:00

  • Continued exploration of 1,2,4-oxadiazole periphery for carbonic anhydrase-targeting primary arene sulfonamides: Discovery of subnanomolar inhibitors of membrane-bound hCA IX isoform that selectively kill cancer cells in hypoxic environment.

    abstract::An expanded set of diversely substituted 1,2,4-oxadiazole-containing primary aromatic sulfonamides was synthesized and tested for inhibition of human carbonic anhydrase I, II, IX and XII isoforms. The initial biochemical profiling revealed a significantly more potent inhibition of cancer-related, membrane-bound isofor...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.12.049

    authors: Krasavin M,Shetnev A,Sharonova T,Baykov S,Kalinin S,Nocentini A,Sharoyko V,Poli G,Tuccinardi T,Presnukhina S,Tennikova TB,Supuran CT

    更新日期:2019-02-15 00:00:00

  • Recent developments of quinolone-based derivatives and their activities against Escherichia coli.

    abstract::Escherichia coli (E. coli) is the most common pathogen in both hospital and community settings, and is capable of causing infections that can lead to serious consequences. Quinolones, one of the most common antibiotics in clinical use, are effective weapons to treat E. coli infections. However, the resistance of E. co...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2018.08.095

    authors: Gao F,Wang P,Yang H,Miao Q,Ma L,Lu G

    更新日期:2018-09-05 00:00:00

  • Synthesis of novel monocarbonyl curcuminoids, evaluation of their efficacy against MRSA, including ex vivo infection model and their mechanistic studies.

    abstract::In continuation of our effort to improve the physiological stability and the antibacterial activity of curcuminoids against drug-resistant bacteria, a series of novel monocarbonyl curcuminoids were synthesized and screened for antibacterial activity against S. aureus and E. coli strains. These curcuminoids showed pote...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2020.112276

    authors: Gagandeep,Kumar P,Kandi SK,Mukhopadhyay K,Rawat DS

    更新日期:2020-06-01 00:00:00

  • Molecular design and anticancer activities of small-molecule monopolar spindle 1 inhibitors: A Medicinal chemistry perspective.

    abstract::As a dual-specificity protein kinase, monopolar spindle 1 (Mps1) is one of the main kinases involved in kinetochore localization and the spindle assembly checkpoint (SAC). Cancer cells often display chromosomal instability, which is a consequence of disfunction of cell cycle checkpoints partially. Mps1 is overexpresse...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2019.04.047

    authors: Wang S,Zhang M,Liang D,Sun W,Zhang C,Jiang M,Liu J,Li J,Li C,Yang X,Zhou X

    更新日期:2019-08-01 00:00:00

  • Design, synthesis and docking studies of benzimidazole derivatives as potential EGFR inhibitors.

    abstract::In this study, a series of benzimidazoles bearing thiosemicarbazide chain or triazole and thiadiazole rings were designed and synthesized. Crystal and molecular structure of the compound 5c has been characterized by single crystal X-ray crystallographic analysis. EGFR kinase inhibitory potencies of synthesized compoun...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2019.04.012

    authors: Celik İ,Ayhan-Kılcıgil G,Guven B,Kara Z,Gurkan-Alp AS,Karayel A,Onay-Besikci A

    更新日期:2019-07-01 00:00:00

  • Recent advances in HER2 positive breast cancer epigenetics: Susceptibility and therapeutic strategies.

    abstract::HER2 amplification/overexpression accounts for aggressive clinical features of HER2 positive breast cancer. Epigenetic changes including DNA methylation, histone modifications and ncRNAs/miRNAs are associated with regulation of DNA chromatin and specifically, gene transcription. Hence, these produce eminent effects up...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2017.07.075

    authors: Singla H,Ludhiadch A,Kaur RP,Chander H,Kumar V,Munshi A

    更新日期:2017-12-15 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

  • Synthesis and pharmacological evaluation of 2(3H)-furanones and 2(3H)-pyrrolones, combining analgesic and anti-inflammatory properties with reduced gastrointestinal toxicity and lipid peroxidation.

    abstract::A series of 3-arylidene-5-(4-chloro-phenyl)-2(3H)-furanones (2-13) and their nitrogen analogues 1-benzylpyrrolones (14-18) were synthesized. The compounds were evaluated for their anti-inflammatory, analgesic, ulcerogenic and lipid peroxidation actions. Some of the newly synthesized compounds showed good anti-inflamma...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2008.10.030

    authors: Alam MM,Husain A,Hasan SM,Suruchi,Anwer T

    更新日期:2009-06-01 00:00:00

  • An exhaustive perspective on structural insights of SGLT2 inhibitors: A novel class of antidiabetic agent.

    abstract::Diabetes mellitus is the global health issue and become an alarming threat in the modern era where human lifestyle gets compromised with modernization. According to the latest statistical report 2020, USA has 9.47% (31 million among 32.72 cr), China has 8.3% (116.4 million among 139.27 cr) and India has 5.6% (77 milli...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2020.112523

    authors: Bhattacharya S,Rathore A,Parwani D,Mallick C,Asati V,Agarwal S,Rajoriya V,Das R,Kashaw SK

    更新日期:2020-10-15 00:00:00

  • Dual inhibition of the α-glucosidase and butyrylcholinesterase studied by molecular field topology analysis.

    abstract::A striking dual inhibition of enzymes α-glucosidase and butyrylcholinesterase by small drug-like molecules, including 1,4-disubstituted-1,2,3-triazoles, chalcones, and benzothiazepines, was rationalized with the help of Molecular Field Topology Analysis, a 3D QSAR technique similar to CoMFA. A common pharmacophore sup...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.04.018

    authors: Jabeen F,Oliferenko PV,Oliferenko AA,Pillai GG,Ansari FL,Hall CD,Katritzky AR

    更新日期:2014-06-10 00:00:00

  • Synthesis of indazole motifs and their medicinal importance: an overview.

    abstract::Indazoles is an important class of heterocyclic compounds having a wide range of biological and pharmaceutical applications. There is enormous potential in the synthesis of novel heterocyclic systems to be used as building blocks for the next generation of pharmaceuticals as anti-bacterial, anti-depressant and anti-in...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2014.11.029

    authors: Gaikwad DD,Chapolikar AD,Devkate CG,Warad KD,Tayade AP,Pawar RP,Domb AJ

    更新日期:2015-01-27 00:00:00

  • Bicyclic polyprenylated acylphloroglucinols and their derivatives: structural modification, structure-activity relationship, biological activity and mechanism of action.

    abstract::Bicyclic polyprenylated acylphloroglucinols (BPAPs), the principal bioactive benzophenone products isolated from plants of genera Garcinia and Hypericum, have attracted noticeable attention from the synthetic and biological communities due to their fascinating chemical structures and promising biological activities. H...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2020.112646

    authors: Phang Y,Wang X,Lu Y,Fu W,Zheng C,Xu H

    更新日期:2020-11-01 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

  • Synthesis and antibacterial study of unsaturated Mannich ketones.

    abstract::Several Mannich ketones of 2-arylmethylenecycloalkanones were synthesised using the classical acid-catalysed Mannich reaction. Antibacterial activity of these new water-soluble compounds was reported against Pseudomonas aeruginosa, Escherichia coli, Staphylococcus aureus, Staphylococcus saprophyticus, Micrococcus lute...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0223-5234(01)01264-8

    authors: Lóránd T,Kocsis B,Sohár P,Nagy G,Kispál G,Krane HG,Schmitt H,Weckert E

    更新日期:2001-09-01 00:00:00

  • Inhibitors of phosphopantetheine adenylyltransferase.

    abstract::Phosphopantetheine adenylyltransferase (PPAT) is an essential enzyme in Coenzyme A biosynthesis. Because bacterial PPAT and mammalian PPAT are dissimilar, this enzyme is an attractive antibacterial target. Based on the structure of the substrate, 4-phosphopantetheine, a dipeptide library was designed, synthesised and ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0223-5234(03)00047-3

    authors: Zhao L,Allanson NM,Thomson SP,Maclean JK,Barker JJ,Primrose WU,Tyler PD,Lewendon A

    更新日期:2003-04-01 00:00:00

  • Linked pyridinyl-thiadiazoles: Design and synthesis as potential candidate for treatment of XDR and MDR tuberculosis.

    abstract::Multi-drug resistant (MDR) and extremely drug resistant (XDR) Mycobacterium tuberculosis strains have turned tuberculosis (TB) as "on the verge of eradication" to "most life threatening" disease. Furthermore, synergy with HIV and other immunosuppressive disease have strengthened its prevalence. This research reports s...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.07.039

    authors: Mahajan NS,Dhawale SC

    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