Therapeutic applications of sulfamates

Winum, Jean‐Yves; Scozzafava, Andrea; Montéro, Jean-Louis; Supuran, Claudiu T.

doi:10.1517/13543776.14.9.1273

Cited by 33 publications

(14 citation statements)

References 113 publications

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“…estrone sulfate, to the active hormones by STS represents the first step in the local production of estrogen and androgens. Therefore, the inhibition of this enzyme (STS), which should decrease the biosynthesis of active hormones, has been a new therapeutic option in the treatment for hormone-dependent diseases [55][56][57][58] such as breast, endometrial and prostate cancers, acne and androgenic alopecia [53,[59][60][61]. Since STS catalyzes the hydrolysis of sulfate monoester bonds in a range of physiological substrates, the incorporation of a sulfamate ester group linked to an aryl ring was considered to be key strategy in the development of potent STS inhibitors [42,[62][63][64][65].…”

Section: Sulfatase Inhibitormentioning

confidence: 99%

A Review of Coumarin Derivatives in Pharmacotherapy of Breast Cancer

Musa

Cooperwood²,

Khan³

2008

CMC

482

190

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The coumarin (benzopyran-2-one, or chromen-2-one) ring system, present in natural products (such as the anticoagulant warfarin) that display interesting pharmacological properties, has intrigued chemists and medicinal chemists for decades to explore the natural coumarins or synthetic analogs for their applicability as drugs. Many molecules based on the coumarin ring system have been synthesized utilizing innovative synthetic techniques. The diversity oriented synthetic routes have led to interesting derivatives including the furanocoumarins, pyranocoumarins, and coumarin sulfamates (COUMATES), which have been found to be useful in photochemotherapy, antitumor and anti-HIV therapy, and as stimulants for central nervous system, antibacterials, anti-inflammatory, anti-coagulants, and dyes. Of particular interest in breast cancer chemotherapy, some coumarins and their active metabolite 7-hydroxycoumarin analogs have shown sulfatase and aromatase inhibitory activities. Coumarin based selective estrogen receptor modulators (SERMs) and coumarin-estrogen conjugates have also been described as potential antibreast cancer agents. Since breast cancer is the second leading cause of death in American women behind lung cancer, there is a strong impetus to identify potential new drug treatments for breast cancer. Therefore, the objective of this review is to focus on important coumarin analogs with antibreast cancer activities, highlight their mechanisms of action and structure-activity relationships on selected receptors in breast tissues, and the different methods that have been applied in the construction of these pharmacologically important coumarin analogs.

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Section: Sulfatase Inhibitormentioning

confidence: 99%

A Review of Coumarin Derivatives in Pharmacotherapy of Breast Cancer

Musa

Cooperwood²,

Khan³

2008

CMC

482

190

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“…Table 2 Representation of all library members (arylsulfamate derivatives 31-55). 3 ( t -B u t y l a c e t i c Acid) c CH 2 -Phenyl ( P h e n y l a c e t i c Acid) d …”

Section: Cleavage Strategy (Recovering the Fi Nal Compounds)mentioning

confidence: 99%

“…Sulfamate derivatives have been known for several years as artifi cial sweeteners (cyclamates) [1], but therapeutic applications are numerous and have signifi cantly broadened in recent years [2,3]. They were fi rst known as anticonvulsants and the drug topimarate, discovered in 1980, is still used in clinical settings for the treatment of refractory epilepsy [4].…”

Section: Introductionmentioning

confidence: 99%

A Sequential Dual Cleavage of the Arylsulfamate Linker to Provide Both Sulfamate and Phenol Derivatives

Fournier¹,

Ciobanu²,

Poirier³

2015

ChemJMold

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Abstract. Tyramine sulfamate was linked to the trityl chloride resin and this polymeric solid support used to introduce two levels of molecular diversity by formation of peptide bonds. A dual cleavage strategy next generated in a sequential way (without resin split) two different types of compounds (phenol and arylsulfamate derivatives), which are therapeutically attractive types of compounds. Here, we used tyramine as a general scaffold, but other arylsulfamate derivatives could be judiciously used to extend the nature of synthesized compounds.

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“…In addition to reporting on the broad series of new STS inhibitors, some of these review articles deal with other topics such as the enzyme structure, mechanisms, biological function, and molecular biology, among others. It is also of interest to mention two additional reviews that, although not focused on STS, summarize all the therapeutic applications of sulfamates including STS inhibition [Winum et al, 2004;. Aryl sulfamate derivatives are well known to inactivate STS and to release the corresponding phenolic group.…”

Section: Inhibitors Of Stsmentioning

confidence: 99%

New cancer drugs targeting the biosynthesis of estrogens and androgens

Poirier

2008

Drug Development Research

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The enzymes involved in the synthesis of steroids are very interesting therapeutic targets. By reducing the levels of androgens and estrogens that stimulate the proliferation of cancer cells, a potent and selective inhibitor of a key-steroidogenic enzyme may become an alternative or a complementary strategy to the use of an antiandrogen or an antiestrogen for the treatment of prostate cancer or breast and endometrial cancers, respectively. Five enzymes, namely 17a-hydroxylase 17a-lyase, aromatase, 17b-hydroxysteroid dehydrogenases, 5a-reductases, and steroid sulfatase were especially studied and found to be interesting targets for the development of inhibitors as potential cancer drugs. The present review will summarize the role of these five enzymes and their inhibitors with a special highlight about the molecules more recently reported in the literature and exhibiting dual therapeutic action. Drug Dev Res 69: 304-318, 2008.

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Therapeutic applications of sulfamates

Cited by 33 publications

References 113 publications

A Review of Coumarin Derivatives in Pharmacotherapy of Breast Cancer

A Review of Coumarin Derivatives in Pharmacotherapy of Breast Cancer

A Sequential Dual Cleavage of the Arylsulfamate Linker to Provide Both Sulfamate and Phenol Derivatives

New cancer drugs targeting the biosynthesis of estrogens and androgens

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