Antitumor agents. Synthesis and biological evaluation of new compounds related to podophyllotoxin, containing the 2,3-dihydro-1,4-benzodioxin system

Capilla, A. S.

doi:10.1016/s0223-5234(01)01231-4

Cited by 28 publications

(5 citation statements)

References 12 publications

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“…Based on the significant biological effect of justicidine (61) and the ring C-aromatized aza analogue (74), Capilla et al [117] prepared some ring C aromatized and ring D modified analogues (Fig. 9).…”

Section: Ring D Modificationsmentioning

confidence: 99%

Podophyllotoxin Derivatives: Current Synthetic Approaches for New Anticancer Agents

You¹

2005

CPD

186

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Podophyllotoxin is an antimitotic natural product. Its inhibitory activity on cell growth led to the development of the clinically valuable anticancer agents, etoposide, teniposide and the water-soluble prodrug, etoposide phosphate. The cytotoxic mechanism of these drugs is the inhibition of topoisomerase II, unlike the lead compound which inhibits mitosis. Through extensive structure-activity relationship studies, several potential drug candidates were synthesized such as GL-331, TOP 53, NK611, and azatoxin. Recently, more complex and diverse analogues have been synthesized either to get more potent compounds or to overcome drug resistance. At the same time, a number of prodrug approaches have been tried to enhance the tumor selectivity or to increase the aqueous solubility. The prodrugs can release cytotoxic etoposide through the actions of hydrolysis, enzymes or catalytic antibodies. More sophisticated prodrug strategies have been applied in etoposide and these produced some interesting results. In this review, the current research trends in the design of new derivatives will be covered with a brief introduction of podophyllotoxin and related analogues.

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Section: Ring D Modificationsmentioning

confidence: 99%

Podophyllotoxin Derivatives: Current Synthetic Approaches for New Anticancer Agents

You¹

2005

CPD

186

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“…On the other hand, the methylenedioxy unit, present in many natural products such as safrole [14], Leucettamine B [15], and Steganacin [16], exhibits a wide variety of biological activities [17–20]. The methylenedioxy unit can be identified in the clinical antitumor agents etoposide, teniposide [21] and lignan lactone podophyllotoxin [22], and structure–activity relationships have shown that the methylenedioxy moiety is fundamental for cytotoxic activity since it can be metabolized by CYP to form metallo–carbene intermediates which may be responsible for the observed antitumor activity of lignans [23–24]. The presence of the methylenedioxy moiety in some other bioactive molecules drastically alters their pharmacological properties.…”

Section: Introductionmentioning

confidence: 99%

First synthesis of 2-(benzofuran-2-yl)-6,7-methylene dioxyquinoline-3-carboxylic acid derivatives

Gao¹,

Liu²,

Jiang³

et al. 2011

Beilstein J. Org. Chem.

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SummaryA facile and inexpensive synthesis of a series of novel methylenedioxy-bearing 2-(benzofuran-2-yl)-quinoline-3-carboxylic acid derivatives 3a–h via the one-pot reaction of ethyl 2-chloromethyl-6,7-methylenedioxyquinoline-3-carboxylate (5) with various substituted salicylaldehydes 6a–g as well as 2-hydroxy-1-naphthaldehyde (6h) is described. Substrate 5 was synthesized by the Friedländer condensation reaction of 2-amino-4,5-methylenedioxybenzaldehyde (4) with ethyl 4-chloro-3-oxobutanoate using KHSO4 as catalyst under ultrasound irradiation conditions. The targeted compounds 3a–h were obtained in good yields of 52–82% and their structures were established based on spectral data and elemental analyses.

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“…Most of the lignans in plants are in a free state, while some of them can combine with glycon and form glycosides and other derivatives. With such structural diversity of lignans being discovered, it is not surprising that many attractive pharmacological activities of the lignan family, such as antitumor [7], antioxidant [5], antibacterial [8], immunosuppressive [9], and antiasthmatic properties [10] were reported. Pertinent to this review, many lignans have been identified with antiviral activities [11].…”

Section: Introductionmentioning

confidence: 99%

Lignans and Their Derivatives from Plants as Antivirals

et al. 2020

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Lignans are widely produced by various plant species; they are a class of natural products that share structural similarity. They usually contain a core scaffold that is formed by two or more phenylpropanoid units. Lignans possess diverse pharmacological properties, including their antiviral activities that have been reported in recent years. This review discusses the distribution of lignans in nature according to their structural classification, and it provides a comprehensive summary of their antiviral activities. Among them, two types of antiviral lignans-podophyllotoxin and bicyclol, which are used to treat venereal warts and chronic hepatitis B (CHB) in clinical, serve as examples of using lignans for antivirals-are discussed in some detail. Prospects of lignans in antiviral drug discovery are also discussed.

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Antitumor agents. Synthesis and biological evaluation of new compounds related to podophyllotoxin, containing the 2,3-dihydro-1,4-benzodioxin system

Cited by 28 publications

References 12 publications

Podophyllotoxin Derivatives: Current Synthetic Approaches for New Anticancer Agents

Podophyllotoxin Derivatives: Current Synthetic Approaches for New Anticancer Agents

First synthesis of 2-(benzofuran-2-yl)-6,7-methylene dioxyquinoline-3-carboxylic acid derivatives

Lignans and Their Derivatives from Plants as Antivirals

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