Synthesis and biological evaluation of novel steroidal[17,16-d][1,2,4]triazolo[1,5-a]pyrimidines

Huang, Le Hui; Zheng, Yong‐Fei; Lu, Yongzheng; Song, Chuanjun; Wang, Yanguang; Yu, Bin

doi:10.1016/j.steroids.2012.03.002

Cited by 94 publications

(31 citation statements)

References 30 publications

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“…During the last decades, fused heterocycles bearing 1,2,4-triazolo [1,5-a]pyrimidine scaffold proved to be of pharmaceutical interest due to the diverse biological activities of these derivatives [1][2][3][4][5]. For example, a derivative functionalized with N-substituted piperidine proved a very good antiviral activity against the wild-type HIV-1 strain, being more potent than the currently used drugs [3].…”

Section: Introductionmentioning

confidence: 99%

“…For example, a derivative functionalized with N-substituted piperidine proved a very good antiviral activity against the wild-type HIV-1 strain, being more potent than the currently used drugs [3]. Polycondensed species with steroid nucleus showed potent inhibitory activity against PC-3 (human prostatic carcinoma), MCF-7 (human breast carcinoma) and EC9706 (human oesophageal carcinoma) cell lines [4].…”

Section: Introductionmentioning

confidence: 99%

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Thermal behaviour of some biologically active species based on complexes with a triazolopyrimidine pharmacophore

Olar

Calu

Badea

et al. 2016

J Therm Anal Calorim

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A series of complexes of type M(pmtp)(CH 3 COO) 2 ÁnH 2 O ((1) M: Co, n = 4.5; (2) M: Ni, n = 3.5; (3) M: Cu, n = 0.5; (4) M: Zn, n = 0; pmtp: 5-phenyl-7-methyl-1,2,4-triazolo[1,5-a]pyrimidine) were synthesised by one-pot condensation. The complexes were characterized by elemental analysis, ESI-MS, IR, UV-Vis-NIR, EPR spectra, magnetic susceptibility at room temperature as well as thermogravimetric analysis. The modifications in the IR spectra of complexes are in accordance with the condensation process and indicate the triazolopyrimidine coordination as unidentate. The electronic and EPR spectra together with magnetic moments indicate an octahedral stereochemistry for paramagnetic ions, except for Cu(II) with a square pyramidal geometry. Processes such as water elimination, acetate into carbonate transformation, as well as oxidative degradation of the triazolopyrimidine derivative were evidenced during thermal decomposition. The complexes exhibited an improved antimicrobial activity in comparison with the ligand, on both planktonic and biofilm-embedded microbial cells. The best antimicrobial activity in both susceptible and resistant strains was obtained for complex (3) followed by complex (1), which can be related to both oxidation state and stereochemical versatility. At high concentrations, the Cu(II) complex exhibits both cytotoxicity on HT 29 tumour cell line and anti-inflammatory activity.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Thermal behaviour of some biologically active species based on complexes with a triazolopyrimidine pharmacophore

Olar

Calu

Badea

et al. 2016

J Therm Anal Calorim

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“…In continuation of our previous work in developing new biologically active modified steroids [11,12,[23][24][25][26][27][28], we herein report a base-promoted three-component one-pot method for the synthesis of steroidal polysubstituted anilines from steroidal α, α-dicyanoalkene, aromatic aldehydes and malononitrile. To the best of our knowledge, this is the first report about the synthesis of steroidal polysubstituted anilines.…”

Section: Introductionmentioning

confidence: 93%

Efficient three-component one-pot synthesis of steroidal polysubstituted anilines

Zhang

Shi

et al. 2015

Steroids

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“…However, their detailed mechanisms of action are less studied. In continuation with our previous interest in identifying potent anticancer agents, we screened our in-house steroid-based molecular library using the MTT assay [14][15][16][17][18][19][20][21][22][23][24], leading to the identification of a structurally symmetric [1,2,4] triazolo [1,5-a] pyrimidine-based steroidal dimer (named by001) having potent antiproliferative activity against several human cancer cell lines, remarkably more potent than its analogs previously synthesized in our group (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Steroidal Dimer by001 Inhibits Proliferation and Migration of Esophageal Cancer Cells via Multiple Mechanisms

Wang¹,

Zhou²,

Shi³

et al. 2017

Preprint

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Following our previous success in identifying new steroid-based anticancer agents, we herein disclosed the structural requirements for retaining high potency against cancer cells and associated modes of action. The structurally novel steroidal dimer by001 inhibited growth of different esophageal cancer cells and colony formation at low micromolar levels, elevated cellular ROS levels and caused mitochondrial dysfunction. Mechanistic studies showed that by001 induced cell death through the mitochondria and death receptor-mediated apoptotic pathways and autophagy induction, as well as inhibited migration.

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Synthesis and biological evaluation of novel steroidal[17,16-d][1,2,4]triazolo[1,5-a]pyrimidines

Cited by 94 publications

References 30 publications

Thermal behaviour of some biologically active species based on complexes with a triazolopyrimidine pharmacophore

Thermal behaviour of some biologically active species based on complexes with a triazolopyrimidine pharmacophore

Efficient three-component one-pot synthesis of steroidal polysubstituted anilines

Steroidal Dimer by001 Inhibits Proliferation and Migration of Esophageal Cancer Cells via Multiple Mechanisms

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