53389-98-3Relevant academic research and scientific papers
Pharmacological analysis and structure determination of 7-methylcyanopindolol-bound β1-adrenergic receptor
Sato, Tomomi,Baker, Jillian,Warne, Tony,Brown, Giles A.,Leslie, Andrew G.W.,Congreve, Miles,Tate, Christopher G.
, p. 1024 - 1034 (2015)
Comparisons between structures of the β1-adrenergic receptor (AR) bound to either agonists, partial agonists, or weak partial agonists led to the proposal that rotamer changes of Ser5.46, coupled to a contraction of the binding pocke
Rh-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to 3-Arylpropenoates: Enantioselective Synthesis of (R)-Tolterodine
Zullo, Valerio,Iuliano, Anna
, p. 1377 - 1384 (2019/01/04)
A highly enantioselective conjugate addition of arylboronic acids to 3-arylpropenoates is presented. The rhodium complexes obtained from deoxycholic acid derived binaphthyl phosphites showed good activity as well as very high enantioselectivity (ee up to 99 %) in the conjugate addition to different ethyl-3-arylpropenoates, allowing to obtain useful chiral building blocks for the synthesis of active pharmaceutical ingredients. The method was applied to the enantioselective synthesis of the antimuscarinic drug (R)-tolterodine.
Potassium tert-Butoxide-Mediated Condensation Cascade Reaction: Transition Metal-Free Synthesis of Multisubstituted Aryl Indoles and Benzofurans
Yang, Pengfei,Xu, Weiyan,Wang, Rongchao,Zhang, Min,Xie, Chunsong,Zeng, Xiaofei,Wang, Min
supporting information, p. 3658 - 3662 (2019/05/17)
An efficient and facile method to synthesize valuable disubstituted 2-aryl indoles and benzofurans in good yields has been demonstrated, based on a tert-butoxide-mediated condensation reaction involving a vinyl sulfoxide intermediate. Products are obtained from N- or O-benzyl benzaldehydes using dimethyl sulfoxide as a carbon source. The methodology features a wide functional group tolerance and transition metal-free environment. Preliminary mechanistic studies suggest that the reaction involves a tandem aldol reaction/Michael addition/dehydrosulfenylation/isomerization sequence through an ionic protocol.
Synthesis of 2,3-Disubstituted Indoles and Benzofurans by the Tandem Reaction of Rhodium(II)-Catalyzed Intramolecular C-H Insertion and Oxygen-Mediated Oxidation
Shen, Hongjuan,Fu, Junkai,Yuan, Hao,Gong, Jianxian,Yang, Zhen
, p. 10180 - 10192 (2016/11/17)
A highly effective and straightforward method to construct a wide range of functionalized 2,3-disubstituted indoles has been developed. The method involves the tandem reaction of rhodium(II)-catalyzed denitrogenative annulation of triazole-based benzyl an
A direct and mild formylation method for substituted benzenes utilizing dichloromethyl methyl ether-silver trifluoromethanesulfonate
Ohsawa, Kosuke,Yoshida, Masahito,Doi, Takayuki
, p. 3438 - 3444 (2013/06/26)
A silver trifluoromethanesulfonate (AgOTf)-promoted direct and mild formylation of benzenes has been developed. The reaction utilizing dichloromethyl methyl ether (Cl2CHOMe) and AgOTf powerfully formylated various substituted benzenes under temperature conditions as low as -78 C without losing the protecting groups on the phenolic hydroxyl group.
Multidimensional optimization of promising antitumor xanthone derivatives
Azevedo, Carlos M.G.,Afonso, Carlos M.M.,Sousa, Diana,Lima, Raquel T.,Helena Vasconcelos,Pedro, Madalena,Barbosa, Jo?o,Corrêa, Arlene G.,Reis, Salette,Pinto, Madalena M.M.
, p. 2941 - 2959 (2013/07/05)
A promising antitumor xanthone derivative was optimized following a multidimensional approach that involved the synthesis of 17 analogues, the study of their lipophilicity and solubility, and the evaluation of their growth inhibitory activity on four human tumor cell lines. A new synthetic route for the hit xanthone derivative was also developed and applied for the synthesis of its analogues. Among the used cell lines, the HL-60 showed to be in general more sensitive to the compounds tested, with the most potent compound having a GI50 of 5.1 μM, lower than the hit compound. Lipophilicity was evaluated by the partition coefficient (Kp) of a solute between buffer and two membrane models, namely liposomes and micelles. The compounds showed a log Kp between 3 and 5 and the two membrane models showed a good correlation (r2 = 0.916) between each other. Studies concerning relationship between solubility and structure were developed for the hit compound and 5 of its analogues.
Practical asymmetric catalytic synthesis of spiroketals and chiral diphosphine ligands
Wang, Xiaoming,Wang, Xubin,Guo, Peihua,Wang, Zheng,Ding, Kuiling
supporting information, p. 2900 - 2907 (2014/03/21)
A practical procedure has been developed for efficient synthesis of chiral aromatic spiroketals and the relevant diphosphine ligands. The procedure includes first asymmetric hydrogenation of readily available α, α'-bis(2-benzyloxyarylidene) ketones cat-al
Expeditious synthesis of benzopyrans via lewis acid-catalyzed C-H functionalization: Remarkable enhancement of reactivity by an ortho substituent
Mori, Keiji,Kawasaki, Taro,Sueoka, Shosaku,Akiyama, Takahiko
supporting information; experimental part, p. 1732 - 1735 (2010/09/05)
An expeditious construction of a benzopyran skeleton via Lewis acid-catalyzed C-H functionalization was achieved. In this process, a [1,5] hydride shift and 6-endo cyclization successively occurred to give benzopyrans. The presence of substituents ortho to the alkoxy group significantly enhanced the reactivity, affording the desired compounds in excellent chemical yields with short reaction times.
Stepwise palladium-catalyzed 1,4-addition of arylboronic acids to enones and regioselective Baeyer-Villiger oxidation for enantioselective synthesis of β-diaryl esters and (+)-(R)-tolterodine
Kobayashi, Kenya,Nishikata, Takashi,Yamamoto, Yasunori,Miyaura, Norio
experimental part, p. 1019 - 1025 (2009/04/13)
Baeyer-Villiger oxidation of chiral β-diaryl ketones synthesized by 1,4-addition of arylboronic acids to β-arylα,β-unsaturated ketones catalyzed by a palladium(2+)-chiraphos complex provided optically active β-diaryl esters up to 98% ee. The protocol was
Rhodium/chiral diene-catalyzed asymmetric 1,4-addition of arylboronic acids to arylmethylene cyanoacetates
Soegel, Sebastian,Tokunaga, Norihito,Sasaki, Keigo,Okamoto, Kazuhiro,Hayashi, Tamio
, p. 589 - 592 (2008/04/12)
Asymmetric 1,4-addition of arylboronic acids to (￡)-methyl 2-cyano-3-arylpropenoates proceeded in the presence of a rhodium catalyst (3 mol %) coordinated with a chiral diene ligand, (R,R)-Ph-bod*, to give high yields of the corresponding methyl 3,3-diaryl-2-cyanopropanoates with high enantioselectivity (up to 99% ee). This catalytic asymmetric transformation was applied to the asymmetric synthesis of (R)-tolterodine. American Chemical Society.
