Synthesis and biological evaluation of novel m-carborane-containing estrogen receptor partial agonists as SERM candidates

Ohta, Kiminori; Ogawa, Tokuo; Kaise, Asako; Endo, Yasuyuki

doi:10.1016/j.bmcl.2015.05.083

Cited by 12 publications

(8 citation statements)

References 29 publications

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“…Among them, compound 44 with a 9,10-dimethyl-m-carborane cage showed a greater ER-binding affinity than compound 39 with two methyl groups into the m-carborane cage. Compound 39 had an increase of Hansch hydrophobic value (π value) [ 87 , 88 ].…”

Section: Carborane Analoguesmentioning

confidence: 99%

Estrogen Receptor Ligands: A Review (2013–2015)

Farzaneh

Zarghi

2016

Sci. Pharm.

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Estrogen receptors (ERs) are a group of compounds named for their importance in both menstrual and estrous reproductive cycles. They are involved in the regulation of various processes ranging from tissue growth maintenance to reproduction. Their action is mediated through ER nuclear receptors. Two subtypes of the estrogen receptor, ERα and ERβ, exist and exhibit distinct cellular and tissue distribution patterns. In humans, both receptor subtypes are expressed in many cells and tissues, and they control key physiological functions in various organ systems. Estrogens attract great attention due to their wide applications in female reproductive functions and treatment of some estrogen-dependent cancers and osteoporosis. This paper provides a general review of ER ligands published in international journals patented between 2013 and 2015. The broad physiological profile of estrogens has attracted the attention of many researchers to develop new estrogen ligands as therapeutic molecules for various clinical purposes. After the discovery of the ERβ receptor, subtype-selective ligands could be used to elicit beneficial estrogen-like activities and reduce adverse side effects, based on the different distributions and relative levels of the two ER subtypes in different estrogen target tissues. Therefore, recent literature has focused on selective estrogen ligands as highly promising agents for the treatment of some types of cancer, as well as for cardiovascular, inflammatory, and neurodegenerative diseases. Estrogen receptors are nuclear transcription factors that are involved in the regulation of many complex physiological functions in humans. Selective estrogen ligands are highly promising targets for treatment of some types of cancer, as well as for cardiovascular, inflammatory and neurodegenerative diseases. Extensive structure-activity relationship studies of ER ligands based on small molecules indicate that many different structural scaffolds may provide high-affinity compounds, provided that some basic structural requirements are present.

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Section: Carborane Analoguesmentioning

confidence: 99%

Estrogen Receptor Ligands: A Review (2013–2015)

Farzaneh

Zarghi

2016

Sci. Pharm.

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“…A large library of carborane derivatives, with different functional groups at the carbon atoms, have already been synthesized ,. Unsubstituted carboranes are known to have an extremely low water solubility, which allows for their exploitation as novel hydrophobic pharmacophores . To increase their solubility in water, carborane derivatives with hydrophilic groups have been synthesized .…”

Section: Introductionmentioning

confidence: 99%

Host–Guest Chemistry of Carboranes: Synthesis of Carboxylate Derivatives and Their Binding to Cyclodextrins

Nekvinda

Grüner

Gabel

et al. 2018

Chemistry A European J

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Polyhedral carboxymethyl carborane (C B H ) derivatives, including mono- and disubstituted o-, m-, and p-isomers, have been synthesized. Supramolecular host-guest complexation of these derivatives with cyclodextrins (CDs; namely, α-, β-, and γ-CD) has been investigated in water. The globular structure of the carborane binding moiety and its hydrophobic character qualify it as an ideal recognition site to form stable inclusion complexes with macrocyclic host molecules in aqueous solution. The measured binding affinities for the carborane derivatives were in the millimolar range (K =10 -10 m ) with differently sized CDs, and preferential binding to β-CD.

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“…inflammatory diseases [48][49][50] Antifungal drug [51] Antipneumococcal agent (lung) [52] Antibacterial activity [53,54 ] β-lactamase inhibitors [55] Antidepressant activity [56] Estrogen receptor partial agonist candidates [57] Brain antitumor agents [58] Nonsecosteroidal vitamin D receptor [59] Antifolate analog [60] Anesthetics [61] NH O N H [53,54] β-lactamase inhibitors inflammatory diseases [48][49][50] Antifungal drug [51] Antipneumococcal agent (lung) [52] Antibacterial activity [53,54 ] β-lactamase inhibitors [55] Antidepressant activity [56] Estrogen receptor partial agonist candidates [57] Brain antitumor agents [58] Nonsecosteroidal vitamin D receptor [59] Antifolate analog [60] Anesthetics [61] NH O N H [55] Antidepressant activity…”

Section: Antifungal Drugmentioning

confidence: 99%

Boron Chemicals in Drug Discovery and Development: Synthesis and Medicinal Perspective

et al. 2022

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A standard goal of medicinal chemists has been to discover efficient and potent drug candidates with specific enzyme-inhibitor abilities. In this regard, boron-based bioactive compounds have provided amphiphilic properties to facilitate interaction with protein targets. Indeed, the spectrum of boron-based entities as drug candidates against many diseases has grown tremendously since the first clinically tested boron-based drug, Velcade. In this review, we collectively represent the current boron-containing drug candidates, boron-containing retinoids, benzoxaboroles, aminoboronic acid, carboranes, and BODIPY, for the treatment of different human diseases.In addition, we also describe the synthesis, key structure–activity relationship, and associated biological activities, such as antimicrobial, antituberculosis, antitumor, antiparasitic, antiprotozoal, anti-inflammatory, antifolate, antidepressant, antiallergic, anesthetic, and anti-Alzheimer’s agents, as well as proteasome and lipogenic inhibitors. This compilation could be very useful in the exploration of novel boron-derived compounds against different diseases, with promising efficacy and lesser side effects.

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Synthesis and biological evaluation of novel m-carborane-containing estrogen receptor partial agonists as SERM candidates

Cited by 12 publications

References 29 publications

Estrogen Receptor Ligands: A Review (2013–2015)

Estrogen Receptor Ligands: A Review (2013–2015)

Host–Guest Chemistry of Carboranes: Synthesis of Carboxylate Derivatives and Their Binding to Cyclodextrins

Boron Chemicals in Drug Discovery and Development: Synthesis and Medicinal Perspective

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