639458-46-1Relevant articles and documents
Novel multi-target azinesulfonamides of cyclic amine derivatives as potential antipsychotics with pro-social and pro-cognitive effects
Zajdel, Pawe?,Kos, Tomasz,Marciniec, Krzysztof,Sata?a, Grzegorz,Canale, Vittorio,Kamiński, Krzysztof,Ho?uj, Ma?gorzata,Lenda, Tomasz,Koralewski, Robert,Bednarski, Marek,Nowiński, Leszek,Wójcikowski, Jacek,Daniel, W?adys?awa A.,Nikiforuk, Agnieszka,Nalepa, Irena,Chmielarz, Piotr,Ku?mierczyk, Justyna,Bojarski, Andrzej J.,Popik, Piotr
supporting information, p. 790 - 804 (2018/02/10)
Currently used antipsychotics are characterized by multireceptor mode of action. While antagonism of dopamine D2 receptors is responsible for the alleviation of “positive” symptoms of schizophrenia and the effects at other, particularly serotonergic receptors are necessary for their additional therapeutic effects, there is no consensus regarding an “ideal” target engagement. Here, a detailed SAR analysis in a series of 45 novel azinesulfonamides of cyclic amine derivatives, involving the aryl-piperazine/piperidine pharmacophore, central alicyclic amine and azinesulfonamide groups has led to the selection of (S)-4-((2-(2-(4-(benzo[b]thiophen-4-yl)piperazin-1-yl)ethyl)pyrrolidin-1-yl)sulfonyl)isoquinoline (62). The polypharmacology profile of 62, characterized by partial 5-HT1AR agonism, 5-HT2A/5-HT7/D2/D3R antagonism, and blockade of SERT, reduced the “positive”-like, and “negative”-like symptoms of psychoses. Compound 62 produced no catalepsy, demonstrated a low hyperprolactinemia liability and displayed pro-cognitive effects in the novel object recognition task and attentional set-shifting test. While association of in vitro features with the promising in vivo profile of 62 is still not fully established, its clinical efficacy should be verified in further stages of development.
USE OF AMINOINDANE COMPOUNDS IN TREATING OVERACTIVE BLADDER AND INTERSTITIAL CYSTITIS
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Page/Page column 142-143, (2014/03/22)
The present application provides methods of using the aminoindane compounds of formula (I) or (II) in treating an overactive bladder or interstitial cystitis by administering one or more of the compounds to a patient.
Asymmetric synthesis of (+)-vertine and (+)-lythrine
Chausset-Boissarie, La?titia,àrvai, Roman,Cumming, Graham R.,Guénée, Laure,Kündig, E. Peter
supporting information; experimental part, p. 6473 - 6479 (2012/09/08)
The total syntheses of the Lythracea alkaloids (+)-vertine and (+)-lythrine are described. Enantioenriched pelletierine is used as a chiral building block and engaged into a two step pelletierine condensation leading to two quinolizidin-2-one diastereomers in a 8:1 ratio. The major product is used in the synthesis of (+)-vertine via aryl-aryl coupling and ring closing metathesis to provide a Z-alkene α to the lactone carbonyl function. The same procedure was used for (+)-lythrine after base induced epimerization of the main quinolizidin-2-one diastereomer. Alternative classical ring closure strategies like macrolactonisation or aryl-aryl coupling failed.
Organocatalytic enantioselective synthesis of quinolizidine alkaloids (+)-myrtine, (-)-lupinine, and (+)-epiepiquinamide
Fustero, Santos,Moscardó, Javier,Sánchez-Roselló, María,Flores, Sonia,Guerola, Marta,Pozo, Carlos Del
experimental part, p. 7412 - 7417 (2011/10/09)
The organocatalytic synthesis of quinolizidine alkaloids (+)-myrtine, (-)-lupinine, and (+)-epiepiquinamide is described. It involved, as the key step, an enantioselective intramolecular aza-Michael reaction (IMAMR) catalyzed by J?rgensen catalyst I, affording the common precursor with high enantioselectivity. This compound was subsequently transformed into the three alkaloids in a highly diastereoselective manner.
Stereoselective total synthesis of the piperidine alkaloids, (+)-coniine, (+)-pseudoconhydrine, and (+)-sedamine through a common intermediate
Satyalakshmi, Gandham,Suneel, Kanaparthy,Shinde, Digambar Balaji,Das, Biswanath
experimental part, p. 1000 - 1005 (2011/09/20)
The stereoselective total synthesis of the piperidine alkaloids, (+)-coniine, (+)-pseudoconhydrine and (+)-sedamine has been achieved through a common intermediate generated from butane-1,4-diol. The synthetic sequence involves a Maruoka asymmetric allylation and ring-closing metathesis as the key steps.
Enzyme assisted enantioselective synthesis of the alkaloid (+)-aloperine
Barilli, Alessio,Belinghieri, Francesca,Passarella, Daniele,Lesma, Giordano,Riva, Sergio,Silvani, Alessandra,Danieli, Bruno
, p. 2921 - 2925 (2007/10/03)
The enantioselective synthesis of the lupinine alkaloid (+)-aloperine is described. The synthetic scheme presents three steps that are mediated by enzymes: kinetic resolution, oxidation of a primary alcohol to an aldehyde and oxidation of a secondary alco
Remote Stereocenter Discrimination in the Enzymatic Resolution of Piperidine-2-ethanol. Short Enantioselective Synthesis of Sedamine and Allosedamine
Angoli, Marco,Barilli, Alessio,Lesma, Giordano,Passarella, Daniele,Riva, Sergio,Silvani, Alessandra,Danieli, Bruno
, p. 9525 - 9527 (2007/10/03)
Kinetic resolution of N-Boc-piperidine-2-ethanol (2), a case of remote stereocenter discrimination, was accomplished by sequential transesterification mediated by two enzymes, Lipase PS and porcine pancreatic lipase, showing opposite enantioselectivity. The gram-scale availability of the two enantiomeric N-Boc alcohols 2a (R) and 2c (S) enlarges their synthetic exploitation for the enantioselective preparation of piperidine alkaloids. As an example, the convenient three-step synthesis of both the enantiomers of sedamine and allosedamine is described.
