1,3,4-Thiadiazoles: a potent multi targeted pharmacological scaffold.

Abstract:

:Despite a significant work on thiadiazoles, continuous efforts are still being made to identify novel heterocyclic compounds with potent biological activities. This review may help the medicinal chemists to develop new leads possessing 1,3,4-thiadiazole nucleus with higher efficacy and reduced side effects. This review throws light on the detailed synthetic approaches which have been used for the synthesis of thiadiazoles. This has been followed by the in depth analysis of the thiadiazoles with respect to their medicinal significance.

journal_name

Eur J Med Chem

authors

Haider S,Alam MS,Hamid H

doi

10.1016/j.ejmech.2014.12.035

subject

Has Abstract

pub_date

2015-03-06 00:00:00

pages

156-77

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(14)01144-1

journal_volume

92

pub_type

杂志文章,评审
  • Synthesis, characterization and antimicrobial activity of some disubstituted 1,3,4-oxadiazoles carrying 2-(aryloxymethyl)phenyl moiety.

    abstract::Disubstituted 1,3,4-oxadaiazoles (4a-z, 4a'-f'), Mannich bases (6a-p) and S-alkylated derivatives (7a-t) have been synthesized from 2-(aryloxymethyl)benzoic acids (1a-d) through a multi-step reaction sequence. The structures of new compounds were established on the basis of their elemental analyses, IR, (1)H NMR, (13)...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2010.06.027

    authors: Naveena CS,Boja P,Kumari NS

    更新日期:2010-11-01 00:00:00

  • Caffeoylglycolic and caffeoylamino acid derivatives, halfmers of L-chicoric acid, as new HIV-1 integrase inhibitors.

    abstract::Human immunodeficiency virus (HIV) integrase (IN) catalyzes the integration of HIV DNA copy into the host cell DNA. L-Chicoric acid (1) has been found to be one of the most potent HIV-1 integrase inhibitor. Caffeoylglycolic and caffeoylamino acid derivatives' halfmeric structures of L-chicoric acid 2 were synthesized ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2007.02.016

    authors: Lee SU,Shin CG,Lee CK,Lee YS

    更新日期:2007-10-01 00:00:00

  • Synthesis and biological activity of novel mycophenolic acid conjugates containing nitro-acridine/acridone derivatives.

    abstract::Hybrid pharmacophore anti-proliferative compounds, comprised of mycophenolic acid (MPA) and 1-nitroacridine/4-nitroacridone derivative have been synthesized and evaluated as inhibitors of five different leukemia cell lines (Jurkat, Molt-4, HL-60, CCRF-CEM, L1210) and human peripheral blood mononuclear cells from healt...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2012.04.040

    authors: Malachowska-Ugarte M,Cholewinski G,Dzierzbicka K,Trzonkowski P

    更新日期:2012-08-01 00:00:00

  • Promising applications of steroid сonjugates for cancer research and treatment.

    abstract::The conjugation of biologically active molecules is a powerful tool for drug discovery used to target a variety of multifunctional diseases including cancer. Conjugated drugs can provide combination therapies in a single multi-functional agent and, by doing so, be more specific and powerful than conventional classic t...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章,评审

    doi:10.1016/j.ejmech.2020.113089

    authors: А Zolottsev V,Latysheva АS,Pokrovsky VS,Khan II,Misharin AY

    更新日期:2021-01-15 00:00:00

  • Structure-based modification of carbonyl-diphenylpyrimidines (Car-DPPYs) as a novel focal adhesion kinase (FAK) inhibitor against various stubborn cancer cells.

    abstract::A family of carbonyl-substituted diphenylpyrimidine derivatives (Car-DPPYs) with strong activity against focal adhesion kinase (FAK), were described in this manuscript. Among them, compounds 7a (IC50 = 5.17 nM) and 7f (IC50 = 2.58 nM) displayed equal anti-FAK enzymatic activity to the lead compound TAE226 (6.79 nM). I...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2019.04.004

    authors: Wang L,Ai M,Yu J,Jin L,Wang C,Liu Z,Shu X,Tang Z,Liu K,Luo H,Guan W,Sun X,Ma X

    更新日期:2019-06-15 00:00:00

  • Peptidyl 3-substituted 1-hydroxyureas as isosteric analogues of succinylhydroxamate MMP inhibitors.

    abstract::To evaluate N-hydroxyurea as zinc binding group in the design of MMP inhibitors, two peptidyl 1-hydroxyureas were prepared by N-hydroxycarbamoylation of the diastereomeric dipeptides H-Leu-Phe-NHMe and H-D-Leu-Phe-NHMe. Peptidyl 1-hydroxyureas were more potent than the parent peptides, but dramatically weaker (4-5 ord...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2007.07.002

    authors: Campestre C,Tortorella P,Agamennone M,Preziuso S,Biasone A,Nuti E,Rossello A,Gallina C

    更新日期:2008-05-01 00:00:00

  • New naphthopyran analogues of LY290181 as potential tumor vascular-disrupting agents.

    abstract::A series of 19 analogues of the antiproliferative naphthopyran LY290181 were prepared for structure-activity relationship studies. We found the best activities for test compounds bearing small substituents at the meta position of the phenyl ring. The mode of action of LY290181 and eight new analogues was studied in de...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.11.055

    authors: Schmitt F,Gold M,Rothemund M,Andronache I,Biersack B,Schobert R,Mueller T

    更新日期:2019-02-01 00:00:00

  • Conformation and recognition of DNA damaged by antitumor cis-dichlorido platinum(II) complex of CDK inhibitor bohemine.

    abstract::A substitution of the ammine ligands of cisplatin, cis-[Pt(NH3)2Cl2], for cyclin dependent kinase (CDK) inhibitor bohemine (boh), [2-(3-hydroxypropylamino)-6-benzylamino-9-isopropylpurine], results in a compound, cis-[Pt(boh)2Cl2] (C1), with the unique anticancer profile which may be associated with some features of t...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.03.041

    authors: Novakova O,Liskova B,Vystrcilova J,Suchankova T,Vrana O,Starha P,Travnicek Z,Brabec V

    更新日期:2014-05-06 00:00:00

  • Design, synthesis and high antitumor potential of new unsymmetrical bisacridine derivatives towards human solid tumors, specifically pancreatic cancers and their unique ability to stabilize DNA G-quadruplexes.

    abstract::New promising unsymmetrical bisacridine derivatives (UAs), have been developed. Three groups including 36 compounds were synthesized by the condensation of 4-nitro or 4-methylacridinone, imidazoacridinone and triazoloacridinone derivatives with 1-nitroacridine compounds linked with an aminoalkyl chain. Cytotoxicity sc...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2020.112599

    authors: Paluszkiewicz E,Horowska B,Borowa-Mazgaj B,Peszyńska-Sularz G,Paradziej-Łukowicz J,Augustin E,Konopa J,Mazerska Z

    更新日期:2020-10-15 00:00:00

  • Alpha (α-) and beta (β-carboranyl-C-deoxyribosides: syntheses, structures and biological evaluation.

    abstract::The syntheses of the unprotected neutral closo-carboranyl-C-deoxyriboses, starting from anomeric mixture of 1-ethynyldeoxyriboses, and their corresponding open-cage nido-derivatives have been described. The structures of both the α- and β-anomers were confirmed by single-crystal X-ray diffraction. While limited water ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.06.005

    authors: Šnajdr I,Janoušek Z,Takagaki M,Císařová I,Hosmane NS,Kotora M

    更新日期:2014-08-18 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

  • Antihyperglycemic and antihyperlipidemic activities of 2-(4-[(2-hydroxybenzyl) amino]-phenyl amino-methyl)-phenol in STZ induced diabetic rats.

    abstract::Oral administration of 2-(4-[(2-hydroxybenzyl) amino]-phenyl amino-methyl)-phenol (HBPMP) (30 mg/kg) to Streptozotocin (STZ) rats produced significant antidiabetic activity after 6 h of HBPMP administration. Treatment of the STZ rats with HBPMP (30 mg/kg/day) for 30 days resulted in a significant decrease in their Fas...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.05.014

    authors: Sirasanagandla S,Kasetti RB,Shaik AN,Natava R,Surtineni VP,Cirradur SR,Chippada A

    更新日期:2013-08-01 00:00:00

  • New 1,2,4-triazole-Chalcone hybrids induce Caspase-3 dependent apoptosis in A549 human lung adenocarcinoma cells.

    abstract::A series of novel 1, 2, 4-triazole/chalcone hybrids was prepared and identified with different spectroscopic techniques. The prepared compounds showed remarkable cytotoxic activity against different cancer cell lines. Compounds 24, 25, 27, 41 and 47 had shown the highest cytotoxicity among the tested compounds against...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.03.073

    authors: Ahmed FF,Abd El-Hafeez AA,Abbas SH,Abdelhamid D,Abdel-Aziz M

    更新日期:2018-05-10 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

  • Synthesis, biological investigation and molecular docking study of N-malonyl-1,2-dihydroisoquinoline derivatives as brain specific and shelf-stable MAO inhibitors.

    abstract::A group of N-malonyl-1,2-dihydroisoquinoline derivatives were synthesized and investigated as brain specific and shelf-stable MAO inhibitors. N-malonyl-1,2-dihydroisoquinoline redox carrier system was linked through amidic bond to 4-chloro and 4-nitrobenzylidenehydrazines (9a-b), as monoamine oxidase inhibitors (MAOIs...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.02.039

    authors: Abd El-Gaber MK,Hassan HY,Mahfouz NM,Farag HH,Bekhit AA

    更新日期:2015-03-26 00:00:00

  • Synthesis and evaluation of antimicrobial activity of 4H-pyrimido[2,1-b]benzothiazole, pyrazole and benzylidene derivatives of curcumin.

    abstract::A novel, one-pot, simple, efficient procedure for 4H-pyrimido[2,1-b]benzothiazole (4a-h), pyrazole (6a-d) and benzylidene (7a-d) derivatives of curcumin under solvent and solvent free conditions in microwave with good yield is have been synthesized. The synthesized compounds were evaluated for their antibacterial acti...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2012.05.020

    authors: Sahu PK,Sahu PK,Gupta SK,Thavaselvam D,Agarwal DD

    更新日期:2012-08-01 00:00:00

  • Design and synthesis of fluorescent ligands for the detection of cannabinoid type 2 receptor (CB2R).

    abstract::The Cannabinoid 2 receptor, CB2R, belonging to the endocannabinoid system, ECS, is involved in the first steps of neurodegeneration and cancer evolution and progression and thus its modulation may be exploited in the therapeutic and diagnostic fields. However, CB2Rs distribution and signaling pathways in physiological...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2020.112037

    authors: Spinelli F,Giampietro R,Stefanachi A,Riganti C,Kopecka J,Abatematteo FS,Leonetti F,Colabufo NA,Mangiatordi GF,Nicolotti O,Perrone MG,Brea J,Loza MI,Infantino V,Abate C,Contino M

    更新日期:2020-02-15 00:00:00

  • In silico design of novel 2H-chromen-2-one derivatives as potent and selective MAO-B inhibitors.

    abstract::Inhibition data on rat monoamine oxidase B isoform of a large number of 7-metahalobenzyloxy-2H-chromen-2-one derivatives (67 compounds) carrying at position 4 a variety of substituents differing in steric, electrostatic, lipophilic and H-bonding properties, were modeled by Gaussian field-based 3D-QSAR and docking simu...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2014.10.029

    authors: Pisani L,Farina R,Nicolotti O,Gadaleta D,Soto-Otero R,Catto M,Di Braccio M,Mendez-Alvarez E,Carotti A

    更新日期:2015-01-07 00:00:00

  • Synthesis and antiviral evaluation of α-L-2'-deoxythreofuranosyl nucleosides.

    abstract::The synthesis of a series of α-L-2'-deoxythreofuranosyl nucleosides featuring the nucleobases A, T, C and U is described in seven steps from 1,2-O-isopropyledene-α-L-threose, involving a Vorbrüggen coupling and a Barton-McCombie deoxygenation protocol as the key steps. All analogues, including a phosphoramidate nucleo...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2011.05.036

    authors: Toti KS,Derudas M,McGuigan C,Balzarini J,Van Calenbergh S

    更新日期:2011-09-01 00:00:00

  • Design, synthesis and identification of silicon-containing HCV NS5A inhibitors with pan-genotype activity.

    abstract::Modification of a HCV NS5A inhibitor, ombitasvir, led to the identification of 10d with improved pan-genotype NS5A inhibition and better pharmacokinetic properties. The key structural changes to ombitasvir include bioisosteric replacement of carbon with silicon atom. Compared with ombitasvir, the activity of anti-HCV ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2018.02.025

    authors: Liu B,Gai K,Qin H,Liu X,Cao Y,Lu Q,Lu D,Chen D,Shen H,Song W,Zhang Y,Wang X,Xu H,Zhang Y

    更新日期:2018-03-25 00:00:00

  • New groups of antimycobacterial agents: 6-chloro-3-phenyl-4-thioxo-2H-1,3-benzoxazine-2(3H)-ones and 6-chloro-3-phenyl-2H-1,3-benzoxazine-2,4(3H)-dithiones.

    abstract::A series of 6-chloro-3-phenyl-4-thioxo-2H-1,3-benzoxazine-2(3H)-ones 3 and a series of 6-chloro-3-phenyl-2H-1,3-benzoxazine-2, 4(3H)-dithiones 4 were synthesized by melting 6-chloro-3-phenyl-2H-1, 3-benzoxazine-2,4(3H)-dione and its derivatives substituted on the phenyl ring 2 with tetraphosphorus decasulfide. Compoun...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0223-5234(00)00174-4

    authors: Waisser K,Gregor J,Kubicová L,Klimesová V,Kunes J,Machácek M,Kaustová J

    更新日期:2000-07-01 00:00:00

  • Synthesis and biological evaluation of novel pyranochalcone derivatives as a new class of microtubule stabilizing agents.

    abstract::Twenty-five novel pyranochalcone derivatives were synthesized and evaluated for their in vitro and in vivo antiproliferative activities. Among them, compound 10i exhibited superior potent activity against 21 tumor cell lines including multidrug resistant phenotype with the IC50 values ranged from 0.09 to 1.30 μM. In a...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2013.01.007

    authors: Cao D,Han X,Wang G,Yang Z,Peng F,Ma L,Zhang R,Ye H,Tang M,Wu W,Lei K,Wen J,Chen J,Qiu J,Liang X,Ran Y,Sang Y,Xiang M,Peng A,Chen L

    更新日期:2013-04-01 00:00:00

  • Salicylanilides as inhibitors of the protein tyrosine kinase epidermal growth factor receptor.

    abstract::A pharmacophore model for ATP-competitive inhibitors interacting with the active site of the EGFR protein tyrosine kinase and a putative binding mode of 4-anilinoquinazoline suggest that a salicylic acid function could serve as the pharmacophore replacement of a pyrimidine ring. Superpositions by CAMM of salicylanilid...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2003.09.010

    authors: Liechti C,Séquin U,Bold G,Furet P,Meyer T,Traxler P

    更新日期:2004-01-01 00:00:00

  • 2-Methyl-4/5-nitroimidazole derivatives potentiated against sexually transmitted Trichomonas: Design, synthesis, biology and 3D-QSAR study.

    abstract::Trichomoniasis is the most prevalent, non-viral sexually transmitted diseases (STD) caused by amitochondriate protozoan Trichomonas vaginalis. Increased resistance of T. vaginalis to the marketed drug Metronidazole necessitates the development of newer chemical entities. A library of sixty 2-methyl-4/5-nitroimidazole ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2016.09.006

    authors: Mandalapu D,Kushwaha B,Gupta S,Singh N,Shukla M,Kumar J,Tanpula DK,Sankhwar SN,Maikhuri JP,Siddiqi MI,Lal J,Gupta G,Sharma VL

    更新日期:2016-11-29 00:00:00

  • 2-Azetidinone derivatives: design, synthesis and evaluation of cholesterol absorption inhibitors.

    abstract::Fourteen new derivatives of the 2-azetidinone cholesterol absorption inhibitors have been synthesized, and three of them were enantiomerically pure. All the new compounds were evaluated for their activity to inhibit cholesterol absorption in rats, and most of them showed comparable effects in lowering the levels of to...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2008.09.033

    authors: Wang Y,Zhang H,Huang W,Kong J,Zhou J,Zhang B

    更新日期:2009-04-01 00:00:00

  • Discovery of potent epidermal growth factor receptor (EGFR) degraders by proteolysis targeting chimera (PROTAC).

    abstract::Epidermal growth factor receptor (EGFR), a member of the HER family, is closely related to the development of multiple cancers. Herein, we report the discovery of small molecule EGFR degraders based on the proteolysis targeting chimera (PROTAC) strategy. In the present study, 13 EGFR degraders containing pyrido[3,4-d]...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2020.112061

    authors: Zhang H,Zhao HY,Xi XX,Liu YJ,Xin M,Mao S,Zhang JJ,Lu AX,Zhang SQ

    更新日期:2020-03-01 00:00:00

  • Novel hydrazone moiety-bearing aminopyrimidines as selective inhibitors of epidermal growth factor receptor T790M mutant.

    abstract::The epidermal growth factor receptor (EGFR) T790M mutant is found in approximately 50% of clinically acquired resistance to gefitinib among patients with non-small cell lung cancer (NSCLC). Here, a series of novel aminopyrimidines bearing a hydrazone moiety were identified as potent and selective EGFR inhibitors. Comp...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2015.09.031

    authors: Qin M,Wang T,Xu B,Ma Z,Jiang N,Xie H,Gong P,Zhao Y

    更新日期:2015-11-02 00:00:00

  • Vocational training for medicinal chemists: views from industry.

    abstract::The Medicinal Chemistry Section of IUPAC sent a questionnaire regarding academic training for medicinal chemists to major research pharmaceutical companies in various countries in July 1992 and again in July 1993. A total of 102 replies were received from 65 companies, mainly from Germany, Italy, Japan, the UK and the...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/0223-5234(96)83968-7

    authors: Busse W,Ganellin C,Mitscher L

    更新日期:1996-01-01 00:00:00

  • Modification of the length and structure of the linker of N(6)-benzyladenosine modulates its selective antiviral activity against enterovirus 71.

    abstract::Very recently, we demonstrated that N(6)-isopentenyladenosine, a cytokinin nucleoside, exerts a potent and selective antiviral effect on the replication of human enterovirus 71. The present study is devoted to the structure optimization of another natural compound: N(6)-benzyladenosine. We mainly focused on the explor...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/j.ejmech.2016.01.036

    authors: Drenichev MS,Oslovsky VE,Sun L,Tijsma A,Kurochkin NN,Tararov VI,Chizhov AO,Neyts J,Pannecouque C,Leyssen P,Mikhailov SN

    更新日期:2016-03-23 00:00:00

  • New styryl sulfones as anticancer agents.

    abstract::New styryl sulfone compounds have been synthesized and evaluated for their anti-proliferative activity. Among the compounds synthesized, one compound (7k) has shown 51% tumor growth inhibition in mice implanted with HT-29 human carcinoma at 400 mg kg(-1) orally. ...

    journal_title:European journal of medicinal chemistry

    pub_type: 杂志文章

    doi:10.1016/s0223-5234(03)00144-2

    authors: Vedula MS,Pulipaka AB,Venna C,Chintakunta VK,Jinnapally S,Kattuboina VA,Vallakati RK,Basetti V,Akella V,Rajgopal S,Reka AK,Teepireddy SK,Mamnoor PK,Rajagopalan R,Bulusu G,Khandelwal A,Upreti VV,Mamidi SR

    更新日期:2003-09-01 00:00:00