Nmr investigation of the spatial structure of quinolizidine alkaloids IV. Conformation of sophoridine in solution

Камаев, Ф. Г.; Leont'ev, V. B.; Aslanov, Kh. A.; Ustynyuk, Yu. A.; Sadykov, A. S.

doi:10.1007/bf00563993

Cited by 2 publications

(3 citation statements)

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“…As shown in Figure 4 (left), the conformation analysis of matrinic core [18], [19] could be a reasonable explanation for the N -alkylation at the 12-position. However, in the 12- N -alkylation of sopharidinic core in 9 series, the N -alkylation of 9 with RX took place just on the 1- N -nitrogen atom (Figure 4), owing to the steric hindrance at the 12-position in sophoridinic series.…”

Section: Resultsmentioning

confidence: 76%

“…We retained the butyric acid chain, and focused the SAR study on the influence of the substituents on the phenyl ring including electron-withdrawing and electron-donating, and the effect of ( S )- or ( R )-configuration of the chiral carbon at the 5-position, respectively. On the basis of this strategy, a series of new N -substituted benzyl matrinic acid ( 2 , 5 S -configuration, Figure 1) and sophoridinic acid ( 3 , 5 R -configuration, Figure 1) derivatives [18], [19] was designed and synthesized. Herein, we describe the synthesis, in vitro anti-HCV evaluation, SAR analysis, in vivo toxicity, as well as pharmacokinetics of this kind of compounds.…”

Section: Introductionmentioning

confidence: 99%

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N-Substituted Benzyl Matrinic Acid Derivatives Inhibit Hepatitis C Virus (HCV) Replication through Down-Regulating Host Heat-Stress Cognate 70 (Hsc70) Expression

Peng

et al. 2013

PLoS ONE

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Heat-stress cognate 70 (Hsc70) is a host factor that helps hepatitis C virus (HCV) to complete its life cycle in infected hepatocytes. Using Hsc70 as a target for HCV inhibition, a series of novel N-substituted benzyl matrinic/sophoridinic acid derivatives was synthesized and evaluated for their anti-HCV activity in vitro. Among these analogues, compound 7c possessing N-p-methylbenzyl afforded an appealing ability to inhibit HCV replication with SI value over 53. Furthermore, it showed a good oral pharmacokinetic profile with area-under-curve (AUC) of 13.4 µM·h, and a considerably good safety in oral administration in mice (LD50>1000 mg/kg). As 7c suppresses HCV replication via an action mode distinctly different from that of the marketed anti-HCV drugs, it has been selected as a new mechanism anti-HCV candidate for further investigation, with an advantage of no or decreased chance to induce drug-resistant mutations.

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Section: Resultsmentioning

confidence: 76%

Section: Introductionmentioning

confidence: 99%

N-Substituted Benzyl Matrinic Acid Derivatives Inhibit Hepatitis C Virus (HCV) Replication through Down-Regulating Host Heat-Stress Cognate 70 (Hsc70) Expression

Peng

et al. 2013

PLoS ONE

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“…Aerial parts of S. alopecuroides were collected from the Baluchistan province of Pakistan and extracted with 80% ethanol. The extract was subjected to solvent−solvent extraction and repeated column chromatography on Si gel to obtain the new alkaloid, 7α-hydroxysophoramine ( 1 ) together with seven known alkaloids: 12β-hydroxysophocarpine ( 2 ), sophoramine 16,17 ( 3 ), 14β-hydroxymatrine, adenocarpine, matrine, sophoridine, , sophocarpine 4,23 and baptifoline. The structures of the compounds were determined unambiguously using either X-ray diffraction technique or 1D and 2D 1 H and 13 C NMR experiments in conjunction with the analysis of mass spectral and other spectroscopic data.…”

Section: Resultsmentioning

confidence: 99%