Interaction of Methimazole with I<sub>2</sub>: X-ray Crystal Structure of the Charge Transfer Complex Methimazole−I<sub>2</sub>. Implications for the Mechanism of Action of Methimazole-Based Antithyroid Drugs

Isaia, Francesco; Aragoni, M. Carla; Arca, Massimiliano; Demartin, Francesco; Devillanova, Francesco A.; Floris, Giovanni; Garau, Alessandra; Hursthouse, Michael B.; Lippolis, Vito; Medda, Rosaria; Oppo, Fabio; Pira, Marilena; Verani, Gaetano

doi:10.1021/jm8001857

Cited by 46 publications

(25 citation statements)

References 10 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…MMI passes through the placenta barrier to the fetus during gestation. The fetus is aff ected independent of thyroid condition of the mother [ 25 ] .…”

Section: Antithyroid Substance Administration Modelmentioning

confidence: 99%

Experimental Models of Developmental Hypothyroidism

2011

View full text Add to dashboard Cite

Hypothyroidism is a systemic disease resulting from either thyroid gland's anatomical and functional absence or lack of hypophyseal stimulation, both of which can lead to deficiency in thyroid hormone (TH) production. TH is essential for human and animal development, growth, and function of multiple organs. Children with deficient TH can develop alterations in central nervous system (CNS), striated muscle, bone tissue, liver, bone marrow, and cardiorespiratory system. Among the clinical outlook are signs like breathing difficulty, cardiac insufficiency, dysphagia, and repeated bronchial aspiration, constipation, muscle weakness, cognitive alterations, cochlear dysfunction, reduced height, defects in temperature regulation, anaemia, jaundice, susceptibility to infection, and others. Experimental and clinical studies have shown that TH is very essential for normal brain development. Other research work based on mice pointed out that a reduced level of TH in pregnant mother leads to congenital hypothyroidism in animal models and it is associated with mental retardation, deep neurologic deficiency that impacts on cognitive, learning, and memory functions. The principal experimental model studies that have focused on hypothyroidism are reviewed in this study. This is important on considering the fact that almost all animal species require thyroid hormones for their metabolism.

show abstract

“…MMI passes through the placenta barrier to the fetus during gestation. The fetus is aff ected independent of thyroid condition of the mother [ 25 ] .…”

Section: Antithyroid Substance Administration Modelmentioning

confidence: 99%

Experimental Models of Developmental Hypothyroidism

2011

View full text Add to dashboard Cite

show abstract

“…Thus, the goal of this study is to investigate effects of hypothyroxinaemia induced by mild ID and hypothyroidism induced by severe ID on PCs dendritic growth in filial cerebella and the underlying mechanisms. In addition, different from ID, methimazole (MMZ), as a TH inhibitor, is believed to block TH biosynthesis by inhibiting thyroperoxidase and is often used to induce hypothyroidism in rats . Therefore, MMZ treatment rats are also observed as positive control group.…”

Section: Introductionmentioning

confidence: 99%

Developmental hypothyroxinaemia and hypothyroidism limit dendritic growth of cerebellar Purkinje cells in rat offspring: involvement of microtubule‐associated protein 2 (MAP2) and stathmin

Wang

Dong

et al. 2014

Neuropathology Appl Neurobio

View full text Add to dashboard Cite

show abstract

“…Among imidazole derivatives, imidazole-2-thiones have been associated to a special class of biologically relevant thiourea derivatives [6] endowed with antithyroid [7], antiproliferative [8], MPP (Matrix MetalloProteinases) inhibitory [9] property and can be used as building blocks for the synthesis of N-aminoimidazole with antiretroviral activity [10].…”

Section: Introductionmentioning

confidence: 99%

Sequential MCR via Staudinger/aza-Wittig versus Cycloaddition Reaction to Access Diversely Functionalized 1-amino-1H-imidazole-2(3H)-thiones

Ciccolini¹,

Mari²,

Favi³

et al. 2019

Preprint

View full text Add to dashboard Cite

A Multicomponent Reaction (MCR) strategy, alternative to the known cycloaddition reaction, towards variously substituted 1-amino-1H-imidazole-2(3H)-thione derivatives has been successfully developed. The novel approach involves α-halohydrazones whose azidation process followed by tandem Staudinger/aza-Wittig reaction with CS2 in a sequential MCR regioselectively leads to the target compounds avoiding the formation of the regioisomer iminothiazoline heterocycle. The approach can be applied to a range of differently substituted α-halohydrazones bearing also electron-withdrawing groups confirming the wide scope and the substituent tolerance of the process for the synthesis of the target compounds. Interestingly, the concurrent presence of reactive functionalities in the scaffolds so obtained, ensures postmodifications in view of N-bridgedheaded heterobicyclic structures.

show abstract

Interaction of Methimazole with I₂: X-ray Crystal Structure of the Charge Transfer Complex Methimazole−I₂. Implications for the Mechanism of Action of Methimazole-Based Antithyroid Drugs

Cited by 46 publications

References 10 publications

Experimental Models of Developmental Hypothyroidism

Experimental Models of Developmental Hypothyroidism

Developmental hypothyroxinaemia and hypothyroidism limit dendritic growth of cerebellar Purkinje cells in rat offspring: involvement of microtubule‐associated protein 2 (MAP2) and stathmin

Sequential MCR via Staudinger/aza-Wittig versus Cycloaddition Reaction to Access Diversely Functionalized 1-amino-1H-imidazole-2(3H)-thiones

Contact Info

Product

Resources

About

Interaction of Methimazole with I2: X-ray Crystal Structure of the Charge Transfer Complex Methimazole−I2. Implications for the Mechanism of Action of Methimazole-Based Antithyroid Drugs

Cited by 46 publications

References 10 publications

Experimental Models of Developmental Hypothyroidism

Experimental Models of Developmental Hypothyroidism

Developmental hypothyroxinaemia and hypothyroidism limit dendritic growth of cerebellar Purkinje cells in rat offspring: involvement of microtubule‐associated protein 2 (MAP2) and stathmin

Sequential MCR via Staudinger/aza-Wittig versus Cycloaddition Reaction to Access Diversely Functionalized 1-amino-1H-imidazole-2(3H)-thiones

Contact Info

Product

Resources

About

Interaction of Methimazole with I₂: X-ray Crystal Structure of the Charge Transfer Complex Methimazole−I₂. Implications for the Mechanism of Action of Methimazole-Based Antithyroid Drugs