14982-15-1Relevant academic research and scientific papers
An efficient, practical synthesis of 2-methoxyestradiol
Xin, Minhang,You, Qidong,Xiang, Hua
, p. 53 - 56 (2010)
An efficient and practical scheme to synthesize 2-methoxyestradiol has been developed. The key step was the copper-mediated methoxylation using ethyl acetate as a co-catalyst to introduce a methoxyl group. These synthetic procedures of four steps from 17β-estradiol as starting material gave 2-methoxyestradiol with a 61% overall yield.
COMPOUNDS AND METHODS FOR TRANS-MEMBRANE DELIVERY OF MOLECULES
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Paragraph 0036, (2018/07/31)
A system for delivery of drugs, and especially genetic drugs such as siRNA or antisense oligonucleotides (ASO) across biological membranes is provided. It comprises a trans- membrane delivery moiety, energized by the membrane internal electrical field, an
PRO-DRUGS AND RELATED METHODS
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Paragraph 0048, (2017/02/24)
The invention relates to Pro-drugs, comprising red-ox-sensitive cleavage sites. The compounds may be utilized in medical practice for targeting of si RNA, antisense oligonucleotides or protein-based therapeutics to the cytoplasmatic compartment of cells both in vitro or in vivo, in a subject in need.
Design, synthesis and biological evaluation of novel 2-methoxyestradiol analogs as dual selective estrogen receptor modulators (SERMs) and antiangiogenic agents
Lao, Kejing,Wang, Yejun,Chen, Mingqi,Zhang, Jingjing,You, Qidong,Xiang, Hua
, p. 390 - 400 (2017/08/22)
2-methoxyestradiol is a novel agent showing both anti-angiogenic and vascular disrupting properties. In this study, a series of 11α-substituted 2-methoxyestradiol analogs have been designed and synthesized targeting dual ERα and microtubulin. Biological e
Copper-catalyzed N- and O-alkylation of amines and phenols using alkylborane reagents
Sueki, Shunsuke,Kuninobu, Yoichiro
supporting information, p. 1544 - 1547 (2013/06/26)
By the reaction of amines with alkylborane reagents in the presence of a catalytic amount of copper(II) acetate Cu(OAc)2 and di-tert-butyl peroxide, a cross-coupling reaction proceeded and alkylated amines were obtained in good to excellent yields. Phenols are also applicable for this reaction, and the corresponding alkyl aryl ethers were produced.
17β-Arylsulfonamides of 17β-aminoestra-1,3,5(10)-trien-3-ol as highly potent inhibitors of steroid sulfatase
Mostafa, Yaser A.,Taylor, Scott D.
experimental part, p. 1535 - 1544 (2012/04/23)
Steroid sulfatase (STS) catalyzes the desulfation of biologically inactive sulfated steroids to yield biologically active desulfated steroids and is currently being examined as a target for therapeutic intervention for the treatment of breast and other steroid-dependent cancers. Here we report the synthesis of a series of 17β-arylsulfonamides of 17β-aminoestra-1,3, 5(10)-trien-3-ol and their evaluation as inhibitors of STS. Some of these compounds are among the most potent reversible STS inhibitors reported to date. Introducing n-alkyl groups into the 4′-position of the 17β-benzenesulfonamide derivative resulted in an increase in potency with the n-butyl derivative exhibiting the best potency with an IC50 of 26 nM. A further increase in carbon units (to n-pentyl) resulted in a decrease in potency. Branching of the 4′-n-propyl group resulted in a decrease in potency while branching of the 4′-n-butyl group (to a tert-butyl group) resulted in a slight increase in potency (IC50= 18 nM). Studies with 3′- and 4′-substituted substituted 17β-benzenesulfonamides with small electron donating and electron withdrawing groups revealed the 3′-bromo and 3′-trifluoromethyl derivatives to be excellent inhibitors with IC50's of 30 and 23 nM, respectively. The 17β-2′-naphthalenesulfonamide was also an excellent inhibitor (IC50= 20 nM) while the 17β-4′-phenylbenzenesulfonamide derivative was the most potent inhibitor of all the compounds studied with an IC50 of 9 nM.
Synthesis of novel steroidal 17α-triazolyl derivatives via Cu(I)-catalyzed azide-alkyne cycloaddition, and an evaluation of their cytotoxic activity in vitro
Frank, éva,Molnár, Judit,Zupkó, István,Kádár, Zalán,W?lfling, János
scheme or table, p. 1141 - 1148 (2011/09/15)
Regioselective Cu(I)-catalyzed 1,3-dipolar cycloaddition of steroidal 17α-azides with different terminal alkynes afforded novel 1,4-disubstituted triazolyl derivatives in good yields in both the estrone and the androstane series. The antiproliferative activities of the structurally related triazoles were determined in vitro on three malignant human cell lines (HeLa, MCF7 and A431), with the microculture tetrazolium assay.
Improved and scalable synthetic route to the synthon 17-β-(2- Carboxyethyl)-1,3,5(10)-estratriene: An important intermediate in the synthesis of bone-targeting estrogens
Nasim, Shama,Vartak, Ashish P.,Pierce, William M.,Grant Taylor,Crooks, Peter A.
scheme or table, p. 772 - 781 (2011/03/20)
An improved, highly scalable methodology for the multigram-scale preparation of an important synthon, 17-β-(2-carboxyethyl)-1,3,5(10)- estratriene, is described. Previous approaches have failed to provide useful quantities of the analytically pure product because of facile retro-Michael breakdown of the-alkoxy carbonyl precursors during workup and isolation operations. The synthetic approach described herein has been designed specifically to sidestep this problematic breakdown process. This new scalable method of preparation overcomes a major hurdle in the exploration of structure-activity relationships centered around novel estradiol derivatives with bone-targeting properties and also provides a scalable process for subsequent developmental work.
Rearrangement and fragmentation of estrogen ether ions: New aspects found with Fourier transform ion cyclotron resonance mass spectrometry
Freudenhammer, Christoph,Grotemeyer, Juergen
experimental part, p. 489 - 501 (2011/10/31)
Electrospray ionization mass spectra of several di- and tri-hydroxy-estratriene-ethers, as well as estradiol and estriol, have been investigated by high-resolution mass spectrometry. The fragmentation mechanisms leading to the loss of water molecules from the protonated molecular ion have been rationalized by using protecting groups as well as mass spectrometric means such as collision-induced dissociation and infrared multi-photon dissociation. The unexpected observation of a simultaneous loss of two water molecules from the protonated estradiol ethers and of three water molecules from the protonated estriol ethers has been discussed with respect to varying reaction mechanisms and rearrangements. Results and conclusions derived from them were obtained by adequate deuterated ethers.
Facile cleavage of ethers in ionic liquid
Cheng, Lili,Aw, Carlin,Ong, Siew Siang,Lu, Yixin
supporting information; experimental part, p. 2008 - 2010 (2009/08/14)
Various alkyl ethers were efficiently cleaved by treating them with pyridinium halides in ionic liquid, and the desired products were obtained in excellent yields.
