116664-93-8Relevant articles and documents
Synthesis of the azaoxoaporphine alkaloid sampangine and ascididemin-type pyridoacridines through TMPMgCl·LiCl-mediated ring closure
Plodek, Alois,K?nig, Mathias,Bracher, Franz
, p. 1302 - 1308 (2015)
We report the synthesis of the azaoxoaporphine alkaloid sampangine (4) and a series of ring A analogues and isomers of the marine pyridoacridine alkaloid ascididemin (2). This approach starts from readily available 1-bromo[2,7]naphthyridine (12) or 4-bromobenzo[c][2,7]naphthyridine (5), and the ring A scaffold bearing an ester moiety is introduced by a Suzuki or Negishi cross-coupling reaction. The final cyclization step was achieved through a directed remote ring metallation with the Knochel-Hauser base (TMPMgCl·LiCl; TMP = 2,2,6,6-tetramethylpiperidinyl), followed by intramolecular trapping of the ester group.
4- Substituted sampangine derivatives: Novel acetylcholinesterase and β-myloid aggregation inhibitors
Chen, Ke-Lin,Gan, Ling,Wu, Zhen-Hua,Qin, Jin-Fang,Liao, Wen-Xia,Tang, Huang
, p. 2725 - 2729 (2018)
A series of 4- substituted sampangine derivatives (4-aminoalkylaminosampangine Ar–NH(CH2)nNR1R2) has been designed, synthesized, and tested for their ability to inhibit acetylcholinesterase (AChE), butyrylcholinesterase (BChE) and β-myloid (Aβ) aggregation. The synthetic compounds exhibited high AChE inhibitory activity and a significant in vitro inhibitory potency toward the self-induced Aβ aggregation. While, treatment of SH-SY5Y cells overexpressing the Swedish mutant form of human β-amyloid precursor protein (APPsw) with derivatives was associated with significant reduction of Aβ42 secretion levels. Moreover, most of the synthetic compounds were predicted to be able to cross the blood-brain barrier (BBB) to reach their targets in the central nervous system (CNS) according to a parallel artificial membrane permeation assay for BBB. The result encourages us to study this class of compounds thoroughly and systematically.
4-substituted Sampangine alkaloid derivative as well as synthesis method and application thereof
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, (2017/07/19)
The invention discloses a 4-substituted Sampangine alkaloid derivative as well as a synthesis method and application thereof. The 4-substituted Sampangine alkaloid derivative is of a structure as shown in the following formula (I). The synthesis method comprises the following steps: putting Sampangine alkaloid which is of a structure as shown in the formula (II) and perbrominated pyridine bromide into a first organic solvent for reaction, thus obtaining 4-bromo-substituted Sampangine alkaloid which is of a structure as shown in the formula (III), then carrying out a reaction between the 4-bromo-substituted Sampangine alkaloid and sodium methylate in a second organic solvent, thus obtaining 4-methoxy substituted Sampangine alkaloid which is of a structure as shown in the formula (IV), and then carrying out reaction on the 4-methoxy substituted Sampangine alkaloid and diamine which is of a structure as shown in the formula (V) in a third organic solvent, thus obtaining a corresponding target compound coarse product. The compounds which are of the structures as shown in the formulas from (I) to (V) are as follows: as shown in the specification, wherein in the formula (I) and the formula (V), n is equal to a value ranging from 2 to 3, R2 is -N(CH3)3, -NEt2, -OH, a compound shown in the specification or a compound shown in the specification.