2349-70-4Relevant academic research and scientific papers
Experimental and semiemprical studies of chemical reactivity of dialkylcadmium reagents addition to α,β-enones
Ghandi, Mehdi,Shahidzadeh, Mansour
, p. 4918 - 4925 (2006)
Experimental and semiempirical calculations were carried out to study the reactivity of dialkylcadmium reagents addition to α,β-enones. It was demonstrated that α,β-enone such as benzoquinone with low lying LUMO energy reacts via single electron transfer (SET) mechanism with the formation of the 1,2 or 1,4-type alkyl addition product depending on the reaction temperature and substrate structure. Site and chemoselectivity in unsymmetrical benzoquinone derivatives are determined by the stability of the cadmium coordinated semienone complex intermediates and the carbon spin densities of these reactive species respectively. On the other hand, by increasing the LUMO energy of α,β-enone system, the reaction mechanism changes from SET to polar addition affording the 1,4-type alkyl addition product. The establishment of a correlation scale between substrate LUMO energies and reaction mechanism presented in this article will be discussed.
Phenolic compounds from the insect Blaps japanensis with inhibitory activities towards cancer cells, COX-2, ROCK1 and JAK3
Yan, Yong-Ming,Zhu, Hong-Jie,Zhou, Feng-Jiao,Tu, Zheng-Chao,Cheng, Yong-Xian
, p. 1029 - 1033 (2019)
The insect Blaps japanensis have been used as an ethnomedicine in China for the treatment of several disorders such as cancer and inflammation. Our investigation with this insect led to the isolation of eight new and two known phenolic compounds. The structures of the new compounds, blapsins C?J (1–8), were identified by spectroscopic data. The inhibitory activities of all the compounds except of 9 against human cancer cells (A549, K562 and Huh-7), COX-2, ROCK1, and JAK3 were evaluated. Several compounds were found to be biologically active in these assays.
Palladium aminopyridine complexes catalyzed selective benzylic C-H oxidations with peracetic acid
Bryliakov, Konstantin P.,Lubov, Dmitry P.,Lyakin, Oleg Yu.,Rybalova, Tatyana V.,Samsonenko, Denis G.,Talsi, Evgenii P.
supporting information, p. 11150 - 11156 (2020/09/02)
Four palladium(ii) complexes with tripodal ligands of the tpa family (tpa = tris(2-pyridylmethyl)amine) have been synthesized and X-ray characterized. These complexes efficiently catalyze benzylic C-H oxidation of various substrates with peracetic acid, affording the corresponding ketones in high yields (up to 100%), at 1 mol% catalyst loadings. Complex [(tpa)Pd(OAc)](PF6) with the least sterically demanding ligand tpa demonstrates the highest substrate conversions and ketone selectivities. Preliminary mechanistic data provide evidence in favor of metal complex-mediated rate-limiting benzylic C-H bond cleavage by an electron-deficient oxidant.
Candida antarctica lipase B-catalyzed regioselective deacylation of dihydroxybenzenes acylated at both phenolic hydroxy groups
Miyazawa, Toshifumi,Hamada, Manabu,Morimoto, Ryohei
, p. 44 - 49 (2016/01/16)
Candida antarctica lipase B proved to be highly active in the deacylation of substituted hydroquinones and resorcinols acylated at both phenolic hydroxy groups. The deacylation reactions were much faster than the corresponding direct acylations of these dihydroxybenzenes catalyzed by the same lipase. More importantly, they took place generally in a markedly regioselective manner: the acyloxy group remote from the substituent was preferentially cleaved. The main or exclusive products obtained were the regioisomers of those produced through the direct acylation of the dihydroxybenzenes. In the case of alkyl-substituted hydroquinone derivatives, the regioselectivity increased with an increase in the bulk of the substituent. In the case of 4-substituted diacylated resorcinols, the 3-O-monoacyl derivatives were obtained generally as the sole products. Quite interestingly, some secondary alcohols proved to act as better acyl acceptors than the corresponding primary alcohols in these enzymatic deacylations.
Re2O7 catalyzed dienone-phenol rearrangement
Xia, Zilei,Hu, Jiadong,Shen, Zhigao,Yao, Qizheng,Xie, Weiqing
, p. 38499 - 38502 (2015/06/24)
The dienone-phenol rearrangement of 4,4-disubstituted cyclohexadienones catalyzed by Re2O7 has been described. Multi-substituted phenols can be efficiently obtained in good to excellent yields by employing this catalytic protocol.
Candida antarctica lipase B-mediated regioselective acylation of dihydroxybenzenes in organic solvents
Miyazawa, Toshifumi,Hamada, Manabu,Morimoto, Ryohei,Maeda, Yuki
, p. 3915 - 3923 (2015/06/02)
Candida antarctica lipase B proved to be a highly active biocatalyst for the direct acylation of phenolic hydroxy groups of substituted hydroquinones and resorcinols, which have rarely been reported so far. More importantly, the acylation reactions took place generally in a markedly regioselective manner: the hydroxy group remote from the substituent was preferentially acylated. In the case of substituted hydroquinones, the selectivity increased with the increase in the bulk of the substituent. Interestingly, the 1-O-monoacylated derivatives were obtained as the sole products in the case of 4-substituted resorcinols.
THIAZOLE COMPOUNDS USEFUL AS ACETYL-COA CARBOXYLASE (ACC) INHIBITORS
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Page/Page column 83, (2013/03/15)
The present invention provides thiazole compounds of Formula I or its pharmaceutically acceptable salts, prodrugs, solvates, N-oxide thereof; solvates of pharmaceutically acceptable salts and N-oxides; pharmaceutically acceptable salts of N-oxides, or prodrugs; or combination or mixtures thereof; (I) The present invention further provides a method for preventing or treating a condition that responds to an Acetyl-CoA Carboxylase (ACC) inhibitor by using compounds of formula (I) or ), its pharmaceutically acceptable salts, prodrugs, solvates, N-oxide thereof; solvates of pharmaceutically acceptable salts and N-oxides; pharmaceutically acceptable salts of N-oxides, or prodrugs; or combination or mixtures thereof.
Synthesis of the fully glycosylated cyclohexenone core of lomaiviticin A
Gholap, Shivajirao L.,Woo, Christina M.,Ravikumar,Herzon, Seth B.
body text, p. 4322 - 4325 (2009/12/26)
We describe two four-step sequences for conversion of the inexpensive reagent ethyl sorbate to either O-allyl-N,N-dimethyl-D-pyrrolosamine or O-allyl-L-oleandrose, protected forms of the 2,6-dldeoxy sugar residues found in the complex bacterial metabolite
Spinazarin and ethylspinazarin, pigments of the sea urchin Scaphechinus mirabilis
Yakubovskaya,Pokhilo,Mishchenko,Anufriev
, p. 819 - 822 (2008/04/05)
2,3,5,8-Tetrahydroxy-1,4-naphthoquinone (spinazarin) and 6-ethyl-2,3,5,8-tetrahydroxy-1,4-naphthoquinone (ethylspinazarin) were first isolated from the sea urchin Scaphechinus mirabilis. The structures of spinazarins were established based on analysis of spectroscopic data. A preparative synthetic route to ethylspinazarin was proposed.
Secondary alcohols act as better nucleophiles than primary alcohols in the lipase-catalyzed regioselective deacylation of dihydroxybenzenes acylated at both phenolic hydroxyls
Miyazawa, Toshifumi,Hamada, Manabu,Morimoto, Ryohei,Murashima, Takashi,Yamada, Takashi
, p. 8334 - 8337 (2008/03/14)
Candida antarctica lipase B (CAL-B) was found to be highly regioselective as well as active in the deacylation of resorcinols and hydroquinones acylated at both phenolic hydroxyls. Contrary to expectation, secondary alcohols acted as better nucleophiles than primary alcohols in these enzymatic deacylations.
