Thin-layer chromatographic mobility of diastereoisomers

Preobrazhenskaya, M. N.; Mikhailova, L. N.; Chemerisskaya, A. A.

doi:10.1016/s0021-9673(00)92419-1

Cited by 5 publications

(2 citation statements)

References 6 publications

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“…The high mobility of cis-isomer was attributed to the low absorptivity of cis-isomer on the silica gel as a result of steric inaccessibility of polar groups. 23 In 1 H NMR, proton at C1 position of the trans-isomer was showing downfield signal as compared to that of cis-isomer. 24 In an another attempt, the use of 10% TFA in water did not produce any product in this reaction, 25 whereas Et 3 N in DCM resulted in the formation of only a trace amount of the product.…”

Section: Results and Discussionmentioning

confidence: 93%

“…This investigation resulted in the isolation of desired product, and interestingly, it was found that the retention factor for the trans-isomer on thin layer chromatography (TLC) was less as compared to that of cis-isomers. The high mobility of cis-isomer was attributed to the low absorptivity of cis-isomer on the silica gel as a result of steric inaccessibility of polar groups . In 1 H NMR, proton at C1 position of the trans-isomer was showing downfield signal as compared to that of cis-isomer .…”

Section: Results and Discussionmentioning

confidence: 96%

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Synthesis and Evaluation of Antiplasmodial Efficacy of β-Carboline Derivatives against Murine Malaria

et al. 2018

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The difficulty of developing an efficient malaria vaccine along with increasing spread of multidrug resistant strain of Plasmodium falciparum to the available antimalarial drugs poses the need to discover safe and efficacious antimalarial drugs to control malaria. An alternative strategy is to synthesize compounds possessing structures similar to the active natural products or marketed drugs. Several biologically active natural products and drugs contain β-carboline moiety. In the present study, few selected β-carboline derivatives have been synthesized and tested for their in vitro and in vivo antiplasmodial activity against the rodent malaria parasite Plasmodium berghei (NK-65). The designed analogs exhibited considerable in vitro antimalarial activity. Two compounds (1R,3S)-methyl 1-(benzo[d][1,3]dioxol-5-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate (9a) and (1R,3S)-methyl 1-(pyridin-3-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate (9b) were further selected for in vivo studies. Both the lead compounds (9a and 9b) were observed to be safe for oral administration. The therapeutic effective dose (ED50) for 9a and 9b were determined and in the animal model, 9a (at 50 mg/kg dose) exhibited better activity in terms of parasite clearance and enhancement of host survival. Biochemical investigations also point toward the safety of the compound to the hepatic and renal functions of the rodent host. Further studies are underway to explore its activity alone as well as in combination therapy with artesunate against the human malaria parasite P. falciparum.

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Section: Results and Discussionmentioning

confidence: 93%

Section: Results and Discussionmentioning

confidence: 96%

Synthesis and Evaluation of Antiplasmodial Efficacy of β-Carboline Derivatives against Murine Malaria

et al. 2018

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Discovery of a Novel Series of Tetrahydro‐β‐carbolines Inducing Autophagic Cell Death in Human Metastatic Melanoma

Ahmed

Elgendy

Laufer

et al. 2014

Archiv der Pharmazie

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Herein, we report the synthesis of novel tetrahydro-β-carbolines that induce cell death via the autophagic pathway. Five of the new compounds induced cell death in a panel of patient-derived human metastatic melanoma cells. The autophagic pathway was confirmed using LC3 autophagosome markers; the involvement of ATG7 and Beclin 1 autophagy regulating genes was confirmed using infection with short hairpin RNA (shRNA) to silence Beclin 1 and ATG7. Compound VIII (IC50 = 2.34-5.15 μM) displayed activities greater than cisplatin against a panel of patient-derived human metastatic melanoma cell lines. The structure-activity relationship (SAR) of this class and the role of the absolute stereochemistry and geometrical isomerism are evaluated.

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Chromatographic behaviour of diastereomers

Palamareva

Kurtev

1979

Journal of Chromatography A

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Thin-layer chromatographic mobility of diastereoisomers

Cited by 5 publications

References 6 publications

Synthesis and Evaluation of Antiplasmodial Efficacy of β-Carboline Derivatives against Murine Malaria

Synthesis and Evaluation of Antiplasmodial Efficacy of β-Carboline Derivatives against Murine Malaria

Discovery of a Novel Series of Tetrahydro‐β‐carbolines Inducing Autophagic Cell Death in Human Metastatic Melanoma

Chromatographic behaviour of diastereomers

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