153718-64-0Relevant academic research and scientific papers
6-Methoxy-7-benzofuranoxy and 6-methoxy-7-indolyloxy analogues of 2-[2-(2,6-Dimethoxyphenoxy)ethyl]aminomethyl-1,4-benzodioxane (WB4101):1 Discovery of a potent and selective α1D-adrenoceptor antagonist
Fumagalli, Laura,Pallavicini, Marco,Budriesi, Roberta,Bolchi, Cristiano,Canovi, Mara,Chiarini, Alberto,Chiodini, Giuseppe,Gobbi, Marco,Laurino, Paola,Micucci, Matteo,Straniero, Valentina,Valoti, Ermanno
, p. 6402 - 6412 (2013/09/23)
Previous results have shown that replacement of one of the two o-methoxy groups at the phenoxy residue of the potent, but not subtype-selective, α1-AR antagonist (S)-WB4101 [(S)-1] by phenyl, or by ortho,meta-fused cyclohexane, or especially by ortho,meta-fused benzene preferentially elicits α1D-AR antagonist affinity. Such observations inspired the design of four new analogues of 1 bearing, in lieu of the 2,6-dimethoxyphenoxy residue, a 6-methoxy-substituted 7-benzofuranoxy or 7-indolyloxy group or, alternatively, their corresponding 2,3-dihydro form. Of these new compounds, which maintain, rigidified, the characteristic ortho heterodisubstituted phenoxy substructure of 1, the S enantiomer of the dihydrobenzofuranoxy derivative exhibited the highest α1D-AR antagonist affinity (pA2 9.58) with significant α1D/ α1A and α1D/α1B selectivity. In addition, compared both to α1D-AR antagonists structurally related to 1 and to the well-known α1D-AR antagonist BMY7378, this derivative had modest 5-HT1A affinity and neutral α1-AR antagonist behavior.
A formal total synthesis of the marine alkaloid aaptamine
Larghi, Enrique L.,Obrist, Blaise V.,Kaufman, Teodoro S.
, p. 5236 - 5245 (2008/09/21)
A new strategy for the synthesis of benzo[de][1,6]naphthyridine derivative 2,3,3a,4,5,6-hexahydroaaptamine, which involves the construction of the isoquinoline ring after elaboration of the quinoline moiety, is described. Since 2,3,3a,4,5,6-hexahydroaaptamine has been previously synthesized as a key intermediate en route to the marine alkaloid aaptamine, access to this compound represents a formal total synthesis of the natural product.
Development of 3,4-dihydro-2H-benzo[1,4]oxazine derivatives as dual thromboxane A2 receptor antagonists and prostacyclin receptor agonists
Ohno, Michihiro,Tanaka, Yoichiro,Miyamoto, Mitsuko,Takeda, Takahiro,Hoshi, Kazuhiro,Yamada, Naohiro,Ohtake, Atsushi
, p. 2005 - 2021 (2007/10/03)
We discovered a novel series of 3,4-dihydro-2H-benzo[1,4]oxazin-8- yloxyacetic acid derivatives as potent dual-acting agents to block the TXA 2 receptor and to activate the PGI2 receptor. We report the synthesis, structure-activity r
An efficient synthesis of the new benzo[c]pyrido[2,3,4-kl]acridine skeleton
Chackal, Sarah,Houssin, Raymond,Henichart, Jean-Pierre
, p. 3502 - 3505 (2007/10/03)
A series of molecules of therapeutic interest, possessing the new skeleton of 1H-benzo[c]pyrido[2,3,4-kl]-acridine with acyl or aminoacyl and methoxy or aminoalkoxy substituents on the aromatic homocycles were synthesized by means of a Friedlaender-type r
Synthetic studies of the pyrroloquinoline nucleus of the makaluvamine alkaloids. Synthesis of the topoisomerase II inhibitor makaluvamine D
White, James D.,Yager, Kraig M.,Yakura, Takayuki
, p. 1831 - 1838 (2007/10/02)
A new synthesis of the pyrrolo[4,3,2-de]quinoline system characteristic of a class of marine alkaloids which includes the prianosins, discorhabdins, and other antineoplastic agents has been developed. The approach is exemplified in a total synthesis of ma
