4705-33-3Relevant academic research and scientific papers
Anti-proliferative activities of flavone-estradiol Stille-coupling adducts and of indanone-based compounds obtained by SnCl4/Zn-catalysed McMurry cross-coupling reactions
Pathe, Gulab Khushalrao,Konduru, Naveen K.,Parveen, Iram,Ahmed, Naseem
, p. 83512 - 83521 (2015/10/19)
We described the synthesis of flavone-estradiol adducts and indanophen based tamoxifen analogs using a novel SnCl4-Zn reagent via a McMurry cross-coupling reaction and their anti-proliferative evaluation against human cervical cancer cell lines (HeLa) and human breast cancer cell lines (MCF-7 and MDA-MB-231). A library of 32 tamoxifen analogs was synthesized using indanone and propiophenone derivatives and evaluated for anti-proliferative activities. Among them, compounds 3ac, 3ad, 3ae and 3ao exhibited better anti-proliferative potencies (IC50 2.13-3.81 μM) than the drug doxorubicin (IC50 50 2.85 ± 0.17 μM and 2.42 ± 0.23 μM; 3.64 ± 0.28 μM and 2.93 ± 0.14 μM) against breast cancer cells (MCF-7 and MDA-MB-231) respectively and IC50 2.17 ± 0.18 μM and 2.56 ± 0.32 μM against cervical cancer cells (HeLa) respectively than the standard drug. However, compounds 6ac, 6ae, 6af and 6ag showed moderate activity (IC50 10 μM). The structure-activity relationship analysis revealed that the optimal combination of side chains at the para-position of propiophenone and fluoro substituent on the indanone moiety enhanced the anti-proliferative activities of tamoxifen analogs.
SnCl4-Zn: A novel reductive system for deoxygenative coupling of aliphatic, aromatic, chalcone epoxide, and indanone carbonyl compounds to olefins
Pathe, Gulab Khushalrao,Ahmed, Naseem
supporting information, p. 1555 - 1561 (2015/03/14)
SnCl4-Zn complex provided a novel reductive system in the deoxygenative cross-coupling of aliphatic, aromatic, chalcone epoxide and indanone carbonyl compounds to olefins in high yield (55-86%) at reflux temperature in THF. The advantage of this reagent is inexpensive, short reaction time, and high yield compared to the reagents used in the McMurry cross-coupling reaction.
Activation of Low-Valent Titanium Reagents with Iodine: Facile Low-Temperature McMurry Reaction and N/O-Debenzylation/Deallylation
Talukdar, Sanjay,Nayak, Sandip K.,Banerji, Asoke
, p. 4925 - 4929 (2007/10/03)
A highly reactive, low-valent titanium (LVT) reagent has been prepared by the addition of substoichiometric amounts of iodine to the LVT species generated by Rieke's method (TiCl3-Li-THF). While the conventional McMurry reaction requires high temperatures and prolonged reaction times for the generation of olefins, the present activated LVT reagent is able to effect the reductive coupling of aliphatic as well as aromatic carbonyls to the corresponding olefins at lower temperatures and much reduced reaction times. The protocol is also useful for the intramolecular coupling reactions leading to the one-step synthesis of heterocycles. The temperature-controlled McMurry reaction provides enhanced diastereoselectivity and features an excellent chemoselectivity. In addition to the McMurry reaction, other SET-induced carbon-heteroatom (O, N) bond cleavages can also be carried out with the activated reagent at a fast rate and at a low temperature in high yields.
Formation and Reactivity of ?-Radical Cation Intermediates in the C-C Coupling Reaction of Phenyldiazomethanes by One-Electron Oxidation
Ishiguro, Katsuya,Ikeda, Masatoshi,Sawaki, Yasuhiko
, p. 3057 - 3066 (2007/10/02)
One-electron oxidation of phenyldiazomethanes afforded cis-stilbene predominantly.The reaction was independent of the oxidation methods, e.g., electrolysis, copper(II), triarylaminium salts, or photosensitized one-electron oxidtions.The C-C coupling reaction was retarded by introducing α-substituents on phenyldiazomethanes.The ESR spectra of diazoalkane radical cations could be obtained during the electrolysis at low temperature and the resulting spectra revealed their unique electronic structure as ?-radicals for most cases.When a bulky tert-butyl group was substituted, the corresponding ?-radical cation was observed, but the C-C coupling reaction did not occur.The novel HOMO-LUMO switching by one-electron removal from the HOMO ?-orbital of diazomethane is explained by the interaction of phenyl group with the C-N-N ?-radical moiety.The C-C coupling reaction proceeds via facile cycloaddition between the diazomethane and ?-radical cation, and the preferential formation of cis-olefins is based on the secondary orbital interaction between the two phenyl groups.The structure and the stability of radical cation intermediates are rationalized on the basis of ab initio calculations.
Diazomethane Radical Cations as a Dipolarophile in the Dimeric Olefin Formation from Diazo-compounds
Ishiguro, Katsuya,Sawaki, Yasuhiko,Iwamura, Hiizu
, p. 1853 - 1856 (2007/10/02)
A novel cycloaddition mechanism involving diazomethane radical cations is proposed for the dimeric olefin formation by the one-electron oxidation of the diazo-compounds.The preference of cis-stilbene formation from phenyldiazomethane is understood by a secondary orbital interaction of phenyl groups on the cycloaddition step.
HYDROGENATION AND OTHER SIDE-REACTIONS DURING THE REDUCTIVE COUPLING OF KETONES WITH LOW-VALENT TITANIUM (McMurry Synthesis).
Dams, R.,Malinowski, M.,Geise, H. J.
, p. 311 - 320 (2007/10/02)
Active titanium slurries, effective in the McMurry coupling reaction of ketones to olefins, are also hydrogenation agents.Sometimes they also promote isomerisation of the originally formed olefin as well as aldol type and pinacol type condensations under special reaction conditions. The most prominent factors promoting hydrogenation are the use of high ratios LiAlH4 : TiCl3 and low temperatures in the formation of the low-valent titanium species.
