Design, synthesis and anticancer evaluation of tetrahydro-β-carboline-hydantoin hybrids

Shankaraiah, Nagula; Nekkanti, Shalini; Chudasama, Karmarajsinh J.; Senwar, Kishna Ram; Sharma, Pankaj; Jeengar, Manish Kumar; Naidu, V.G.M.; Srinivasulu, Vunnam; Srinivasulu, Gannoju; Kamal, Ähmed

doi:10.1016/j.bmcl.2014.10.038

Cited by 46 publications

(23 citation statements)

References 25 publications

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“…Antinociceptive activity has been described for racemic harmicine [5] and the optically active form has been isolated from an extract of the leaves of Kopsia griffithii [6]. Some cis and trans isomers of hydantoin hybrids have been prepared and their in vitro cytotoxicity has been evaluated against lung, cervical, prostate and breast carcinoma [7]. A large number of stereoselective syntheses have been developed for such pharmacologically important alkaloids and some of these were reviewed by Czarnocki et al [8].…”

Section: Introductionmentioning

confidence: 99%

Enantioseparation of ß-carboline derivatives on polysaccharide- and strong cation exchanger-based chiral stationary phases. A comparative study

Lajkó

Grecsó

Megyesi

et al. 2016

Journal of Chromatography A

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In this study we attempted to describe in a comparative manner the enantioselectivity performance of six different polysaccharide- and two strong cation exchanger-type chiral stationary phases (CSPs) for the resolution of free and N-protected β-carboline derivatives. On commercially available cellulose- or amylose-based CSPs, the enantioseparations were carried out in normal-phase mode by variation of the nature and the concentration of the alcohol modifier in n-hexane as mobile phase. With the application of strong cation exchanger-type CSPs, the enantioseparations were optimized by the variation of methanol-acetonitrile bulk solvent compositions in the presence of various amounts of acid and base additives acting as counter-ions. Detailed thermodynamic investigations revealed that in all cases the enantioseparations observed were enthalpically driven, i.e. the retention and selectivity decreased with increasing temperature. Elution sequences were determined routinely; no general rule was found on polysaccharide-based CSPs, while on the two enantiomeric strong cation exchanger-type CSPs the predicted reversal of the elution sequence could be confirmed on switching from one enantiomeric CSP to the other form.

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Section: Introductionmentioning

confidence: 99%

Enantioseparation of ß-carboline derivatives on polysaccharide- and strong cation exchanger-based chiral stationary phases. A comparative study

Lajkó

Grecsó

Megyesi

et al. 2016

Journal of Chromatography A

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“…Formation of coumarin THBC hybrids 3 was confirmed by NMR. In a typical example, compound 3 a (C 6 ‐CH 3 ) exhibited a singlet at 5.54 ppm, characteristic of C 1 ′ ‐H of tetrahydro‐ β ‐carbolines . Two multiplets at 2.98 ppm and 2.7 ppm have been assigned to N‐CH 2 and benzylic CH 2 protons respectively.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Human Anticancer Cell Line Studies on Coumarin‐β‐carboline Hybrids as Possible Antimitotic Agents

Samundeeswari

Kulkarni

Joshi³

et al. 2016

ChemistrySelect

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A series of coumarin tetrahydro‐β‐carboline hybrids 3 have been synthesized by the Pictet‐Spengler reaction. Stoichiometrically controlled DDQ oxidation has led to dihydro 4 and β‐carboline 5. In vitro anticancer activity against 60 cell lines has revealed the potency of 3 f, 4 a and 5 c. In silico studies indicate the binding properties of 5 c with Kinesin spindle protein (KSP) and tubulin protein. Gel electrophoresis studies revealed that compound 3 f partially cleaved the CT‐DNA, whereas the ring C aromatized compound 5 c completely cleaved the CT‐DNA. Structures of the newly synthesized compounds are confirmed by spectroscopic and X‐ray studies.

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“…Trujillo and co‐workers investigated tetrahydro‐ β ‐carboline‐1‐carboxylic acids and their analogs, such as (±)‐5, as inhibitors of mitogen‐activated protein kinaseactivated protein kinase 2 . Syntheses of β ‐carboline alkaloids, such as henrycinol A and B or Eg5, an inhibitor of hydantoin hybrids, have also been reported . Several routes for the synthesis of pharmacologically important natural products have been reviewed ,…”

Section: Introductionmentioning

confidence: 99%

Enzymatic Strategy for the Resolution of New 1‐Hydroxymethyl Tetrahydro‐β‐carboline Derivatives in Batch and Continuous‐Flow Systems

2016

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Many alkaloids containing a tetrahydro‐β‐carboline skeleton have well‐known therapeutic effects, leading to increased interest in the synthesis of these natural products. Enantiomers of N‐Boc‐protected 1‐hydroxymethyl‐1,2,3,4‐tetrahydro‐β‐carboline [(±)‐7], 1‐hydroxymethyl‐6‐methoxy‐1,2,3,4‐tetrahydro‐β‐carboline [(±)‐8], and 1‐hydroxymethyl‐6‐fluoro‐1,2,3,4‐tetrahydro‐β‐carboline [(±)‐9] were prepared through enzymecatalyzed asymmetric acylation of their primary hydroxyl group. The preliminary experiments were performed in a continuous‐flow system, while the preparative‐scale resolutions were done as batch reactions. Excellent enantioselectivities (E>200) were obtained with Candida antarctica lipase B (CAL‐B) and acetic anhydride in toluene at 60 °C. The recovered alcohols and the produced esters were obtained with high enantiomeric excess values (ee≥96 %). The O‐acylated enantiomers [(S)‐10–(S)‐12)] were transformed into the corresponding amino alcohols [(S)‐7–(S)‐9)] with methanolysis. Microwave‐assisted Boc removals were also performed and resulted in the corresponding compounds (R)‐4–(R)‐6 and (S)‐4–(S)‐6 without a drop in the enantiomeric excess values (ee≥96 %).

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Design, synthesis and anticancer evaluation of tetrahydro-β-carboline-hydantoin hybrids

Cited by 46 publications

References 25 publications

Enantioseparation of ß-carboline derivatives on polysaccharide- and strong cation exchanger-based chiral stationary phases. A comparative study

Enantioseparation of ß-carboline derivatives on polysaccharide- and strong cation exchanger-based chiral stationary phases. A comparative study

Synthesis and Human Anticancer Cell Line Studies on Coumarin‐β‐carboline Hybrids as Possible Antimitotic Agents

Enzymatic Strategy for the Resolution of New 1‐Hydroxymethyl Tetrahydro‐β‐carboline Derivatives in Batch and Continuous‐Flow Systems

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