Design, synthesis and biological evaluation of 1,4-dihydrothieno[3′,2′:5,6]thiopyrano[4,3-c]pyrazole-3-carboxylic amide derivatives as potential estrogen receptor antagonists

Sun, Rui; Song, Jing; Liu, Si Jie; Zhao, Hui; Chun, Yung; Zhang, Ai Jun; Koirala, Diwa; Li, Da Wei; Hu, Chun

doi:10.1016/j.cclet.2010.10.029

Cited by 7 publications

(5 citation statements)

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“…Sun et al [28], synthesized a new class of 1,4-dihydrothieno[3′,2′:5,6]thiopyrano[4,3- c ]pyrazole-3-carboxylic amides and assessed their anticancer potential against MCF-7 tumor cell line by MTT method and compared to positive control (tamoxifen). Among the target compounds, compounds 25 ( a and b ) were found to be more active against selected cell line (Table 8, Fig.…”

Section: Introductionmentioning

confidence: 99%

Estrogen alpha receptor antagonists for the treatment of breast cancer: a review

Sharma

Kumar

2018

Chemistry Central Journal

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BackgroundCancer is at present one of the leading causes of death in the world. It accounts for 13% of deaths occurred worldwide and is continuously rising, with an estimated million of deaths up to 2030. Due to poor availability of prevention, diagnosis and treatment of breast cancer, the rate of mortality is at alarming level globally. In women, hormone-dependent estrogen receptor positive (ER+) breast cancer making up approximately 75% of all breast cancers. Hence, it has drawn the extensive attention of researchers towards the development of effective drugs for the treatment of hormone-dependent breast cancer. Estrogen, a female sex hormone has a vital role in the initiation and progression of breast malignancy. Therefore, estrogen receptor is the central target for the treatment of breast cancer.ConclusionIn this review, we have studied various classes of antiestrogens that have been designed and synthesized with selective binding for estrogen alpha receptor (ER). Since estrogen receptor α is mainly responsible for the breast cancer initiation and progression, therefore there is need of promising strategies for the design and synthesis of new therapeutic ligands which selectively bind to estrogen alpha receptor and inhibit estrogen dependent proliferative activity.

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Section: Introductionmentioning

confidence: 99%

Estrogen alpha receptor antagonists for the treatment of breast cancer: a review

Sharma

Kumar

2018

Chemistry Central Journal

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“…3‐(Thiophen‐2‐ylthio)propanoic acid (1) was synthesized from 2‐mercapto thiophene and acrylic acid . Treatment of 1 with oxalyl chloride and tin chloride under a nitrogen atmosphere resulted in ketone intermediate 2 , which was treated with dimethyl oxalate at room temperature in the presence of sodium hydride for 24 h to provide 3 . A mixture of 3 and hydrazine hydrate in acetic acid was then refluxed for 12 h to afford 4 .…”

Section: Resultsmentioning

confidence: 99%

“…The mixture was filtered and dried to give 1.5 g (59.0%) of 3 , which is a yellow solid. MP: 93–95 °C ; 1 H‐NMR (600 MHz, DMSO‐ d 6 ): δ 3.76 (s, 3H), 4.15 (s, 2H), 7.35 (d, 1H, J = 4.8 Hz), 7.41 (d, 1H, J = 4.8 Hz).…”

Section: Methodsmentioning

confidence: 99%

“…A mixture of 3 (0.51 g, 2.0 mmol), 80% hydrazine hydrate (2 mL, 0.032 mol) and 10 mL of HOAc was heated at reflux for 12 h. Then, the solution was poured into 50 mL water and filtered to give 0.32 g (63.2%) of 4 , which is a white solid. MP: 94–96 °C ; 1 H‐NMR (300 MHz, CDCl 3 ): δ3.97 (s, 3H), 4.33 (s, 2H), 7.18 (d, 1H, J = 5.3 Hz), 7.40 (d, 1H, J = 5.3 Hz).…”

Section: Methodsmentioning

confidence: 99%

“…We report herein a series of 1, 4‐dihydrothieno [3′, 2′:5, 6]thiopyrano‐[4, 3‐c]pyrazole‐3‐carboxamide derivatives as potential inhibitors to 5‐LOX. Previously, derivatives of the basic scaffold of these carboxamide derivatives have been reported as estrogen receptor antagonists .…”

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Identification of 1, 4‐Dihydrothieno[3′, 2′:5, 6]thiopyrano[4, 3‐c]pyrazole Derivatives as Human 5‐Lipo‐oxygenase Inhibitors

Zhu

Meng

et al. 2014

Chem Biol Drug Des

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A series of novel 1,4-dihydrothieno[3',2':5,6]thiopyrano[4,3-c]-pyrazole-3-carboxamide derivatives were synthesized and evaluated for their inhibitory activity to human 5-lipo-oxygenase (5-LOX). Compound 7c was found to exhibit significant inhibition to human 5-LOX with IC50 value of 5.7 ± 0.9 μm. Compound 7c was further studied using molecular docking in order to delineate its structure-activity relationship and to gain insight into the design of effective 5-LOX inhibitors.

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Degradation Performance of Estrogen During Anaerobic Digestion of Pig Manure

Luo,

Zhao,

Yao

et al. 2023

Waste Biomass Valor

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Design, synthesis and biological evaluation of 1,4-dihydrothieno[3′,2′:5,6]thiopyrano[4,3-c]pyrazole-3-carboxylic amide derivatives as potential estrogen receptor antagonists

Cited by 7 publications

References 3 publications

Estrogen alpha receptor antagonists for the treatment of breast cancer: a review

Estrogen alpha receptor antagonists for the treatment of breast cancer: a review

Identification of 1, 4‐Dihydrothieno[3′, 2′:5, 6]thiopyrano[4, 3‐c]pyrazole Derivatives as Human 5‐Lipo‐oxygenase Inhibitors

Degradation Performance of Estrogen During Anaerobic Digestion of Pig Manure

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