The preparation of estradiol-17β sulfates with triethylamine-sulfur trioxide

Dusza, John P.; Joseph, Joseph P.; Bernstein, Seymour

doi:10.1016/0039-128x(85)90079-0

Cited by 19 publications

(10 citation statements)

References 9 publications

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“…SO 3 adducts are resulting from the combination of SO 3 , an acceptor of electrons or a Lewis acid, with a donor of electrons or Lewis bases. Adducts of SO 3 with organic bases including Py, trimethylamine (TMA), and triethylamine (TEA), or amides such as DMF, have in general found extensive use and have in the last decades been replacing the sulfuric acid derivatives . The stability of the adduct directly varies with the force of the base used and inversely with its reactivity .…”

Section: Sulfation Methodsmentioning

confidence: 99%

Emerging Sulfated Flavonoids and other Polyphenols as Drugs: Nature as an Inspiration

2013

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Nature uses sulfation of endogenous and exogenous molecules mainly to avoid potential toxicity. The growing importance of natural sulfated molecules, as modulators of a number of physiological and pathological processes, has inspired the synthesis of non-natural sulfated scaffolds. Until the 1990s, the synthesis of sulfated small molecules was almost restricted to derivatives of flavonoids and aimed mainly at structure elucidation and plant biosynthesis studies. Currently, the synthesis of this type of compounds concerns structurally diverse scaffolds and is aimed at the development of potential drugs and/or exploitation of the biological effects of sulfated metabolites. Some important hit compounds are emerging from sulfated flavonoids and other polyphenols mainly as anticoagulant and antiviral agents. When compared with polymeric macromolecules such as heparins, sulfated small molecules could be of value in therapeutics due to their hydrophobic nature that can contribute to improve the bioavailability. This review highlights the synthetic approaches that were applied to obtain monosulfated or polysulfated phenolic small molecules and compiles the diverse biological activities already reported for this type of derivatives. Toxicity and pharmacokinetic parameters of this emerging class of derivatives will also be considered, emphasizing their value for therapeutic applications.

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Section: Sulfation Methodsmentioning

confidence: 99%

Emerging Sulfated Flavonoids and other Polyphenols as Drugs: Nature as an Inspiration

2013

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“…These complexes have been used for sulfating a variety of scaffolds containing alcoholic, phenolic, amine, thiol and other functional groups. Complexes of SO 3 with organic bases including pyridine (Py), trimethylamine (NMe 3 ), and triethylamine (NEt 3 ), or amides such as DMF have typically found extensive usage 51–55…”

Section: Chemical Sulfation Approachesmentioning

confidence: 99%

Chemical sulfation of small molecules—advances and challenges

2010

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“…[3‐ 14 C]‐E1‐3S ammonium salt ( 9 ), [3‐ 14 C]‐17β‐E2‐17S ammonium salt ( 10 ), and [3‐ 14 C]‐17β‐E2‐3,17diS diammonium salt ( 11 ) were synthesized from [3‐ 14 C]‐E1 ( 1 ) or [3‐ 14 C]‐17β‐E2 ( 2 ) in three steps (Figure ), according to the literature with modifications. Firstly, 1 and 2 reacted with SO 3 ‐triethylamine complex [(Et) 3 N•SO 3 ] in dry pyridine to form sulfate ester‐triethylamine complexes ( 6 , 7 , and 8 ), which were then treated with 1 M KOH‐methanol to form 3 , 4 , and 5 potassium salt, which were converted to corresponding ammonium salts 9 , 10 , and 11 after purification by preparative TLC on silica gel using an ammonia‐containing eluent, in yield of 48%, 25%, and 54%, respectively, and with radiochemical purity of 99%, 99%, and 98%, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…14 C]-E1-3S ammonium salt(9),[3][4][5][6][7][8][9][10][11][12][13][14] C]-17β-E2-17S ammonium salt (10), and [3-14 C]-17β-E2-3,17diS diammonium salt (11) were synthesized from [3-14 C]-E1 (1) or [3-14 C]-17β-E2(2)in three steps(Figure 1), according to the literature[26][27][28] with modifications. Firstly, 1 and 2 reacted with SO 3 -triethylamine complex [(Et) 3 N•SO 3 ] in dry pyridine to form sulfate ester-triethylamine complexes(6, …”

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confidence: 99%

Synthesis and characterization of ¹⁴C‐labelled sulfate conjugates of steroid oestrogens

Wang

et al. 2014

Labelled Comp Radiopharmac

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Steroid oestrogens are typical endocrine-disrupting compounds in the environment and are excreted from the human and animals mainly as conjugates, including sulfate and glucuronide salts. The oestrogen conjugates are largely biologically inactive, but they can be de-conjugated and release free oestrogens, which usually exhibit strong oestrogenicity. Therefore, it is important to study the fate of oestrogen conjugates in the environment. However, because of the complexity of environmental matrixes, time-consuming pre-treatments of samples are usually required to reduce the interference of the matrixes. (14)C radioisotope can trace target substances and their degradation products at low concentrations in complex environmental samples and is therefore essential in such studies. We synthesized three oestrogen sulfates with (14)C-labelling at the ring, i.e. [3-(14)C]-estrone-3-sulfate ammonium salt, [3-(14)C]-17β-estradiol-17-sulfate ammonium salt, and [3-(14)C]-17β-estradiol-3,17-disulfate diammonium salt with radiochemical purities of >98% by sulfation of [3-(14)C]-labelled estrone and 17β-estradiol in dry pyridine with SO3 -triethylamine at room temperature or 90-95 °C, followed by hydrolysis with KOH-methanol solution and purification by preparative thin-layer chromatography on silica gel using an ammonia-containing eluent. The products were characterized by mass spectrometry and (13)C and (1)H nuclear magnetic resonance spectroscopy, using their corresponding non-labelled compounds. The (14)C-labelled oestrogen conjugates provide possibilities for studying their fate in soil and sediment environments as well as in the animal manure.

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The preparation of estradiol-17β sulfates with triethylamine-sulfur trioxide

Cited by 19 publications

References 9 publications

Emerging Sulfated Flavonoids and other Polyphenols as Drugs: Nature as an Inspiration

Emerging Sulfated Flavonoids and other Polyphenols as Drugs: Nature as an Inspiration

Chemical sulfation of small molecules—advances and challenges

Synthesis and characterization of ¹⁴C‐labelled sulfate conjugates of steroid oestrogens

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The preparation of estradiol-17β sulfates with triethylamine-sulfur trioxide

Cited by 19 publications

References 9 publications

Emerging Sulfated Flavonoids and other Polyphenols as Drugs: Nature as an Inspiration

Emerging Sulfated Flavonoids and other Polyphenols as Drugs: Nature as an Inspiration

Chemical sulfation of small molecules—advances and challenges

Synthesis and characterization of 14C‐labelled sulfate conjugates of steroid oestrogens

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Synthesis and characterization of ¹⁴C‐labelled sulfate conjugates of steroid oestrogens