Arylnaphthalene lactone analogues: synthesis and development as excellent biological candidates for future drug discovery

Zhao, Chuang; Rakesh, K.P.; Mumtaz, Saira; Balakrishna, Moku; Asiri, Abdullah M.; Marwani, Hadi M.; Manukumar, H.M.; Qin, Hua‐Li

doi:10.1039/c7ra13754k

Cited by 46 publications

(21 citation statements)

References 65 publications

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“…coumarin [ 1 ], campthotecin [ 2 ], (−)-cleistenolide [ 3 ], (+)-crassalactones [ 4 , 5 ], or styryl lactones [ 6 ], including goniothalamin [ 7 ] or 5,6-dehydrokavain [ 8 ]. Lignan lactones, known for their potent antiproliferative activity, are secondary metabolites isolated from dietary or medicinal plants containing naphtalene unit [ 9 ] or dibenzylbutyrolactone framework i.a. isohaichulactone [ 10 ], matairesinol [ 11 ], 7-hydroxymatairesinol [ 12 ], mammalian lignan enterolactone [ 13 ].…”

Section: Introductionmentioning

confidence: 99%

Preparation of Enantiomeric β-(2′,5′-Dimethylphenyl)Bromolactones, Their Antiproliferative Activity and Effect on Biological Membranes

et al. 2018

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Three novel enantiomeric pairs of bromolactones possesing a 2,5-dimethylphenyl substituent at the β-position of the lactone ring have been synthesized from corresponding enantiomeric (E)-3-(2′,5′-dimethylphenyl)hex-4-enoic acids (4) by kinetically controlled bromolactonization with N-bromosuccinimide (NBS). γ-Bromo-δ-lactones (5) were isolated as the major products. Absolute configurations of stereogenic centers of γ-bromo-δ-lactones (5) were assigned based on X-ray analysis; configurations of cis δ-bromo-γ-lactones (6) and trans δ-bromo-γ-lactones (7) were determined based on mechanism of bromolactonization. Synthesized compounds exhibited significant antiproliferative activity towards the four canine cancer cell lines (D17, CLBL-1, CLB70, and GL-1) and one human cancer line (Jurkat). Classifying the compounds in terms of activity, the most active were enantiomers of trans δ-bromo-γ-lactones (7) followed by enantiomers of cis isomer (6) and enantiomeric γ-bromo-δ-lactones (5). Higher activity was observed for all stereoisomers with S configuration at C-4 in comparison with their enantiomers with 4R configuration. Synthesized compounds did not induce hemolysis of erythrocytes. The results of the interaction of bromolactones with red blood cell membranes suggest that these compounds incorporate into biological membranes, concentrating mainly in the hydrophilic part of the bilayer but have practically no influence on fluidity in the hydrophobic region. The differences in interactions with the membrane between particular enantiomers were observed only for γ-lactones: stronger interactions were found for enantiomer 4R,5R,6S of cis γ-lactone (6) and for enantiomer 4S,5R,6S of trans γ-lactone (7).

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Section: Introductionmentioning

confidence: 99%

Preparation of Enantiomeric β-(2′,5′-Dimethylphenyl)Bromolactones, Their Antiproliferative Activity and Effect on Biological Membranes

et al. 2018

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“…Naphthalenes are attractive aromatic compounds on account of their diverseb iological activity, as well as their photophysical and fluorescencep roperties. [1,2] Consequently,s ubstantial efforts have been devoted to the development of synthetic routes to various naphthalene skeletons. [3,4] Among these methods, ap articularly powerful and efficient strategy is based on the transition-metal-catalyzed carbon-carbonb ond-forming cycloaromatization [5,6] of benzo-fused 1,3-dien-5-ynes.…”

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confidence: 99%

“…[a,b] [a] Reactionc onditions: 1 (0.4-0.5 mmol, [ Table 2. Scope of the ruthenium-catalyzed 1,2-carbon migration/cyclization with respect to 2-alkynyl-a-methylstyrene derivatives (1). [a,b] [a] Reactionc onditions: 1 (0.4-0.5 mmol, [ www.chemeurj.org low (47 %r ecovery of 1p).…”

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confidence: 99%

Ruthenium‐Catalyzed Cycloisomerization of 2‐Alkynylstyrenes via 1,2‐Carbon Migration That Leads to Substituted Naphthalenes

Watanabe

Abe

Mutoh

et al. 2018

Chemistry A European J

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“…Tandem conjugate additionaldol reaction protocol (Ogiku et al, 1990;Kamal et al, 1994), benzoin condensation-thermal cyclization (Hayat et al, 2015), and electrophilic aromatic substitution protocols (González et al, 1978;Ogiku et al, 1995) have also been reported. Recently, synthetic approaches and biological activities of arylnaphthalene lignan lactones were reviewed by Zhao et al (2018).…”

Section: Introductionmentioning

confidence: 99%

Transition Metal-Mediated Annulation Approaches for Synthesis of Arylnaphthalene Lignan Lactones

Park

Kim

et al. 2020

Front. Chem.

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Arylnaphthalene lignan lactones belong to a class of natural lignans, and more than 60 analogs have been isolated. Their pharmacological activities as well as unique structural features have attracted considerable attention from medicinal and synthetic chemists. Since the first synthesis in 1895, many synthetic methodologies with ionic or pericyclic reaction mechanisms have been reported. Transition metal catalysts sometimes provide exceptional synthetic versatility for the syntheses of natural compounds. Recently, transition metal-mediated methodologies were investigated for the construction of basic scaffolds of arylnaphthalene lignan lactones. Five kinds of transition metal catalysts containing gold, manganese, nickel, palladium, and silver have been explored. Most of the metal catalysts successfully created arylnaphthalene lactones by intermolecular or intramolecular annulative cyclization. In this review, all reports of transition metal-mediated annulative construction of arylnaphthalene lignan lactones were compiled, and synthetic approaches, mechanistic aspects, and successful applications were discussed.

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Arylnaphthalene lactone analogues: synthesis and development as excellent biological candidates for future drug discovery

Abstract: A review of recent developments in the synthesis and biological applications of arylnaphthalene lactones analogs.

Cited by 46 publications

References 65 publications

Preparation of Enantiomeric β-(2′,5′-Dimethylphenyl)Bromolactones, Their Antiproliferative Activity and Effect on Biological Membranes

Preparation of Enantiomeric β-(2′,5′-Dimethylphenyl)Bromolactones, Their Antiproliferative Activity and Effect on Biological Membranes

Ruthenium‐Catalyzed Cycloisomerization of 2‐Alkynylstyrenes via 1,2‐Carbon Migration That Leads to Substituted Naphthalenes

Transition Metal-Mediated Annulation Approaches for Synthesis of Arylnaphthalene Lignan Lactones

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