- The effect of exchanging various substituents at the 2-position of 2-methoxyestradiol on cytotoxicity in human cancer cell cultures and inhibition of tubulin polymerization
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A new set of estradiol derivatives bearing various substituents at the 2-position were synthesized in order to further elucidate the structural parameters associated with the antitubulin activity and cytotoxicity of 2-substituted estradiols. The potencies
- Cushman, Mark,Mohanakrishnan, Arasambattu K.,Hollingshead, Melinda,Hamel, Ernest
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Read Online
- A Novel 1,3 O -> Silyl Shift and Deacylation Reaction Mediated by Tetra-n-butylammonium Fluoride in an Aromatic System
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A novel 1,3 O -> C migration of a silyl group accompanied by a deacylation reaction was discovered during the conversion of 2-acetyl-3,17-bis(tert-butyldimethylsilyl)-β-estradiol (4) and 3,17-bis(tert-butyldimethylsilyl)-2-propionyl-β-estradiol (5) to 2,17-bis(tert-butyldimethylsilyl)-β-estradiol (6) in the presence of tetra-n-butylammonium fluoride.A crossover experiment indicated that the transformation is intramolecular.
- He, Hu-Ming,Fanwick, Phillip E.,Wood, Karl,Cushman, Mark
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Read Online
- Olefination estradiol compound as well as preparation method and application thereof (by machine translation)
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The invention relates to an enestradiol compound as well as preparation and application, and provides an optimal alkylenated modification site. The structural formulas (1)~(6). The prostate cancer cell line PC - 3 and the breast cancer cell MCF F F have e
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Paragraph 0030-0033
(2019/08/12)
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- Oxalic Acid Monothioester for Palladium-Catalyzed Decarboxylative Thiocarbonylation and Hydrothiocarbonylation
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Oxalic acid monothioester (OAM), an easily accessible and storable reagent, was reported herein as a thioester synthetic equivalent for palladium-catalyzed decarboxylative thiocarbonylation of organohalides and hydrothiocarbonylation of unsaturated carbon-carbon bonds at room temperature with high chemo- and regioselectivity. The reaction is applicable to the synthesis of cysteine-derived thioesters, thus allowing chemical modification of cysteine-containing peptides. Decarboxylation of OAM proceeds through oxidative addition of Pd(0) to the acyl-S bond, which accounts for the very mild reaction conditions.
- Zhao, Bin,Fu, Yao,Shang, Rui
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supporting information
p. 9521 - 9526
(2019/11/28)
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- Palladium-catalyzed intramolecular reductive cross-coupling of Csp 2-Csp3 bond formation
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A Pd-catalyzed efficient reductive cross-coupling reaction without metallic reductant to construct a Csp2-Csp3 bond has been reported. A PdIV complex was proposed to be a key intermediate, which subsequently went through d
- Liu, Hui,Wei, Jianpeng,Qiao, Zongjun,Fu, Yana,Jiang, Xuefeng
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supporting information
p. 8308 - 8313
(2014/07/08)
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- Mild arming and derivatization of natural products via an In(OTf) 3-catalyzed arene iodination
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Figure presented Iodination of arene-containing natural products employing N-iodosuccinimide catalyzed by In(OTf)3 at ambient temperature is reported as a versatile and mild method for natural product derivatization amenable to small scale. This process facilitates natural product derivatization of arene moieties for SAR studies, homo- and heterodimerization of natural products, and also conjugation with reporters such as biotin via subsequent metal-mediated coupling reactions.
- Zhou, Cong-Ying,Li, Jing,Peddibhotla, Satyamaheshwar,Romo, Daniel
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supporting information; experimental part
p. 2104 - 2107
(2010/09/15)
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- Mild and efficient iodination of aromatic and heterocyclic compounds with the NaClO2/NaI/HCl system
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NaClO2/NaI in the presence of HCl is a mild, cheap, and non-toxic reagent for the iodination of phenols, including estradiol and naphthol, aromatic amines, and heterocyclic substrates, e.g., indoles, 8-hydroxyquinoline, imidazole, in fair to excellent yields by a very simple isolation protocol. The scope of the procedure is exemplified by the first iodination of 5-nitroindole to 3-iodo-5-nitroindole in 75% yield.
- Lista, Liliana,Pezzella, Alessandro,Napolitano, Alessandra,d'Ischia, Marco
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p. 234 - 239
(2008/09/16)
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- Intravenous injection of human sex steroid hormone-binding globulin in mouse decreases blood clearance rate and testicular accumulation of orally administered [2-125I]iodobisphenol A
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Bisphenol A, an environmental compound with estrogenic activity, has been shown to bind human sex steroid hormone-binding globulin (hSHBG), the main plasma transport protein which regulates the metabolism of androgens and estrogens and limits their access
- Bendridi, Nadia,Mappus, Elisabeth,Grenot, Catherine,Lejeune, Herve,Yves Cuilleron, Claude,Pugeat, Michel
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p. 637 - 645
(2007/10/03)
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- Synthesis, antitubulin and antimitotic activity, and cytotoxicity of analogs of 2-methoxyestradiol, an endogenous mammalian metabolite of estradiol that inhibits tubulin polymerization by binding to the colchicine binding site
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In order to define the structural parameters associated with the antitubulin activity and cytotoxicity of 2-methoxyestradiol, a mammalian metabolite of estradiol, an array of analogs was synthesized and evaluated. The potencies of the new congeners as inh
- Cushman,He,Katzenellenbogen,Lin,Hamel
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p. 2041 - 2049
(2007/10/02)
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- Reaction of Benzeneselenyl Halides with Estrogens
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The reaction of estradiol and estrone with benzeneselenyl chloride affords mainly 2-phenylselenyl adducts which are readily converted into the corresponding 2-halogenated estrogens upon treatment with a variety of reagents.
- Ali, Hasrat,Lier, Johan E. van
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p. 269 - 271
(2007/10/02)
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- Efficient regioselective a-ring functionalization of oestrogens
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Complete series of 2-halo- and 2-cyano-oestrogens have been prepared in good to high yields: 2-chloro, 2-bromo, 2-iodo, and 2-cyano derivatives via oestrogen-thallium (III) bis(trifluoroacetate) intermediates, and 2- and 4- fluorooestrogens by direct functionalization using N-fluoropyridinium triflate.
- Bulman Page, Philip C.,Hussain, Fazal,Maggs Paul Morgan, James L.,Kevin Park
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p. 2059 - 2068
(2007/10/02)
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- An Alternative Route to 2-Bromo- and 2-Iodo-estradiols from Estradiol
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Through careful choice of reaction conditions, alkylation of estradiol with chloromethyl methyl ether may yield either the 3,17β-bis(methoxymethyl) ether or the 3-methoxymethyl ether derivative.Treatment of either of these protected estradiols with s-butyllithium, then with trimethylsilyl chloride affords, regioselectively, the 2-trimethylsilyl derivatives which can conveniently be converted into 2-bromo- or 2-iodo-estradiol.
- Pert, Derek J.,Ridley, Damon D.
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p. 303 - 309
(2007/10/02)
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- IODINATION OF PHENOLS USING CHLORAMINE T AND SODIUM IODIDE
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A convenient procedure for the iodination of many substituted phenols uses chloramine T and sodium iodide in DMF, DMSO, or acetonitrile.
- Kometani, Tadashi,Watt, David S.,Ji, Tae
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p. 2043 - 2046
(2007/10/02)
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- Regioselective Synthesis of 2-Chloromercurio-estradiol and -estrone Derivatives: A Novel Approach to A-Ring Substituted Estrogens
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The following derivatives of estradiol and estrone, 3-methoxyestra-1,3,5(10)-trien-17β-yl acetate (3a), 3-methoxyestra-1,3,5(10)-trien-17-one (3b), estra-1,3,5(10)-triene-3,17β-diyl diacetate (1f), and 3-acetoxyestra-1,3,5(10)-trien-17-one (1g), can be regioselectively mercuriated at the less hindered position 2.The 2-mercurio derivative (4a), prepared from (3a), can be used as the starting material for the synthesis of some 2-substituted estrogens, such as 2-halogeno- and 2-hydroxy-estrogens.Additionally, the 2-chloromercurio-4-bromo derivative (5c) can be obtained from 4-bromo-3-methoxyestra-1,3,5(10)-trien-17β-yl acetate (2f), whereas from 3-methoxyestra-1,3,5(10)-triene-2,17β-diyl diacetate (3g) the 4-chloromercurio derivative (5d) can also be obtained.An explanation of the regioselectivity shown by some electrophiles towards the aromatic A-ring of estrogens is presented.
- Santaniello, Enzo,Fiecchi, Alberto,Ferraboschi, Patrizia,Ravasi, Manuela
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p. 2765 - 2770
(2007/10/02)
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