Regiodefined synthesis of brominated hydroxyanthraquinones related to proisocrinins

Roy, Joyeeta; Mal, Tanushree; Jana, Supriti; Mal, Dipakranjan

doi:10.3762/bjoc.12.52

Cited by 6 publications

(3 citation statements)

References 50 publications

(35 reference statements)

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“…In 2016, Mal and co-workers demonstrated a regiodefined synthesis of the brominated hydroxyanthraquinones 47 and 48 , related to proisocrinins (Scheme 3 ). 22 Proisocrinins were the first water-soluble anthraquinone pigments, and two routes have been reported for their synthesis. The first route proceeds through a Darzens condensation, in which the first step is an H–K annulation.…”

Section: Hauser–kraus Annulation In Total Synthesesmentioning

confidence: 99%

Synthesis of Natural Products, Carbocycles, and Heterocycles by Hauser–Kraus Annulation

Sankara¹,

Gaikwad²,

Namboothiri³

2023

Synlett

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In this account, we have summarized the recent developments in Hauser-Kraus (H-K) annulation with respect to the synthesis of natural products, other functionalized and fused carbocycles and spiro-heterocycles. Although classical H-K annulation is between a 1,4-dipolar synthon (a 3-nucleophilic phthalide), and a 1,2-dipolar synthon (a Michael acceptor), alternative modes of annulation such as [4+4] and [4+1] as well as other reactivity of 3-nucleophilic phthalide which were reported in recent years are also covered in this account.

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Section: Hauser–kraus Annulation In Total Synthesesmentioning

confidence: 99%

Synthesis of Natural Products, Carbocycles, and Heterocycles by Hauser–Kraus Annulation

Sankara¹,

Gaikwad²,

Namboothiri³

2023

Synlett

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“…(c) A mixture of 2,4-dibromo-1-hydroxyanthraquinone 3 (1 mmol) and subsequent aryl boronic acid (4,(6)(7)(8)(9)(10)(11)(12) (2.2 mmol), Pd(PPh 3 ) 4 (10 mol %), Bu 4 NBr (1 mmol) and K 2 CO 3 (4 mmol) was stirred in toluene-water mixture (100 and 20 mL) at 100 • C for 4-6 h (TLC) in an argon flow. After cooling to 25 • C, the mixture was diluted with benzene (200 mL) and washed with water.…”

Section: Procedures For Suzuki-miyaura Reactionsmentioning

confidence: 99%

“…A brief literature survey revealed that the routes for the construction of anthraquinone core are primarily based upon five categories, such as Friedel-Crafts condensations of benzene derivatives with functionalized phthalic anhydrides or phthaloyl dichlorides [8], Hauser annulations of cyanophthalides with cyclohexenones [9], Diels-Alder reactions [10,11], cross-coupling reaction and transition metal-mediated reactions [5,12] and biomimetic aldol condensations [13]. However, some annulation processes suffer from serious limitations which include the poorly efficient, and require several synthetic steps, harsh reaction conditions or using of substrates that are synthetically demanding.…”

Section: Introductionmentioning

confidence: 99%

1-Hydroxyanthraquinones Containing Aryl Substituents as Potent and Selective Anticancer Agents

et al. 2020

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A series of 1,2-, 1,4-disubstituted or 1,2,4-trisubstituted anthraquinone-based compounds was designed, synthesized, characterized and biologically evaluated for anticancer efficacy. 2- or 4-arylated 1-hydroxy-9,10-antraquinones (anthracene-9,10-diones) were prepared by Suzuki–Miyaura cross-coupling reaction of 1-hydroxy-2-bromoanthraquinone, 1-hydroxy-4-iodoanthraquinone or 1-hydroxy-2,4-dibromoanthraquinone with arylboronic acids. The cross-coupling reaction of 2,4-dibromo-9,10-anthraquinone with arylboronic acids provide a convenient approach to 2,4-bis arylated 1-hydroxyanthraquinones with a variety of aryl substituent in the 2 and 4 position. The cytotoxicity of new anthraquinone derivatives was evaluated using the conventional MTT assays. The data revealed that six of the aryl substituted compounds among the entire series 3, 15, 16, 25, 27, 28 were comparable potent with the commercially available reference drug doxorubicin on the human glioblastoma cells SNB-19, prostate cancer DU-145 or breast cancer cells MDA-MB-231 and were relatively safe towards human telomerase (h-TERT)immortalized lung fibroblasts cells. The results suggested that the in vitro antitumor activity of synthesized 2-aryl, 4-aryl- and 2,4-diaryl substituted 1-hydroxyanthraquinones depends on the nature of the substituent within the cyclic backbone. Docking interaction of 2-, 4-substituted and 2,4-disubstituted 1-hydroxyanthraquinones indicates intercalative mode of binding of compounds with DNA topoisomerase. The interaction with the DNA of 4-aryl-13, 15, 16 and 4-(furan-3-yl)-23 1-hydroxyanthraquinones was experimentally confirmed through a change in electroforetic mobility. Further experiments with 1-hydroxy-4-phenyl-anthraquinone 13 demonstrated that the compound induced cell cycle arrest at sub-G1 phase in DU-145 cells in the concentration 1.1 μM, which is probably achieved by inducing apoptosis. 4-Arylsubstituted 1-hydroxyanthraquinones 13 and 16 induced the enhancement of DNA synthesis on SNB19 cell lines.

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Hauser–Kraus, Sammes, Staunton–Weinreb, and Tamura Annulations

Koning¹,

Georgiou²,

Michael³

et al. 2021

Organic Reactions

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This chapter provides a detailed survey of the Hauser–Kraus, Sammes, Staunton–Weinreb, and Tamura annulation reactions, as reported in the literature through March 2021. These reactions provide an efficient means for the synthesis of polycyclic aromatic compounds and related systems. The mechanism, scope, and limitations of each annulation reaction are covered, and typical methods for the preparation of the requisite starting materials (phthalides, homophthalic anhydrides, and related precursors) are provided. Applications of these annulation reactions as key steps in the synthesis of selected aromatic natural products are included, as are representative experimental procedures for accomplishing the annulation reactions.

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Regiodefined synthesis of brominated hydroxyanthraquinones related to proisocrinins

Cited by 6 publications

References 50 publications

Synthesis of Natural Products, Carbocycles, and Heterocycles by Hauser–Kraus Annulation

Synthesis of Natural Products, Carbocycles, and Heterocycles by Hauser–Kraus Annulation

1-Hydroxyanthraquinones Containing Aryl Substituents as Potent and Selective Anticancer Agents

Hauser–Kraus, Sammes, Staunton–Weinreb, and Tamura Annulations

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