Cytotoxic Effects, Alkylating Properties and Molecular Modeling of Coumarin Derivatives (I) and Their Phosphonic Analogues (II) and (III).

Budzisz, Elsbieta; Brzezińska, Elżbieta; Krajewska, Urszula; Różalski, Marcin

doi:10.1002/chin.200343119

Cited by 37 publications

(42 citation statements)

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“…Chemically, bicyclic and tricyclic COUMATES (23)(24)(25)(26)(27)(28)(29)(30)(31)(32)(33)(34)(35)(36)(37) and their close relatives the 676 OXEPINs (e.g. 38) are aryl sulfamates (Ar-SO 2 NH 2 ), which are irreversible inhibitors of STS.…”

Section: Sulfatase Inhibitormentioning

confidence: 99%

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A Review of Coumarin Derivatives in Pharmacotherapy of Breast Cancer

Musa

Cooperwood²,

Khan³

2008

CMC

490

190

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The coumarin (benzopyran-2-one, or chromen-2-one) ring system, present in natural products (such as the anticoagulant warfarin) that display interesting pharmacological properties, has intrigued chemists and medicinal chemists for decades to explore the natural coumarins or synthetic analogs for their applicability as drugs. Many molecules based on the coumarin ring system have been synthesized utilizing innovative synthetic techniques. The diversity oriented synthetic routes have led to interesting derivatives including the furanocoumarins, pyranocoumarins, and coumarin sulfamates (COUMATES), which have been found to be useful in photochemotherapy, antitumor and anti-HIV therapy, and as stimulants for central nervous system, antibacterials, anti-inflammatory, anti-coagulants, and dyes. Of particular interest in breast cancer chemotherapy, some coumarins and their active metabolite 7-hydroxycoumarin analogs have shown sulfatase and aromatase inhibitory activities. Coumarin based selective estrogen receptor modulators (SERMs) and coumarin-estrogen conjugates have also been described as potential antibreast cancer agents. Since breast cancer is the second leading cause of death in American women behind lung cancer, there is a strong impetus to identify potential new drug treatments for breast cancer. Therefore, the objective of this review is to focus on important coumarin analogs with antibreast cancer activities, highlight their mechanisms of action and structure-activity relationships on selected receptors in breast tissues, and the different methods that have been applied in the construction of these pharmacologically important coumarin analogs.

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Section: Sulfatase Inhibitormentioning

confidence: 99%

“…Studies have shown that compound 3 as well as 4-hydroxycoumarin inhibited cell proliferation in a gastric carcinoma cell line [37]. An in vitro proliferation assay of the mechanism of action of coumarins on the growth and metabolism of human tumor cells e.g.…”

Section: Introductionmentioning

confidence: 99%

A Review of Coumarin Derivatives in Pharmacotherapy of Breast Cancer

Musa

Cooperwood²,

Khan³

2008

CMC

490

190

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“…Single crystals suitable for charge-density analysis were obtained by recrystallization of the samples obtained after synthesis [11]. The crystals were obtained by evaporation from toluene.…”

Section: Recrystallization and Data Collectionmentioning

confidence: 99%

Electron-density studies on hydrogen bonding in chromone derivatives. Part II: comparative study

2011

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The experimental electron density of a chromone derivative was determined from a multipole refinement of 100 K X-ray synchrotron data and complemented by theoretical calculations with experimental and optimized geometry. Atomic and topological properties were obtained using the Quantum Theory of Atoms in Molecules approach. The examination of topological parameters unambiguously showed p-delocalization within the H-bonded ring. The application of source function analysis confirmed the intramolecular N-HÁÁÁO hydrogen bond to be a resonance-assisted hydrogen bond. The topological study confirmed the covalent nature of N-HÁÁÁO interaction and the electrostatic nature of weak C-HÁÁÁO interactions.

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“…The number of viable cells was counted in a Bürker haemocytometer using trypan-blue exclusion assay. [67] The values of IC 50 (the concentration of test compounds required to reduce the cell survival fraction to 50 % of the control) were calculated from concentration-response curves (as illustrated in Figure 2) and used as a measure of cellular sensitivity to a given treatment. All data were expressed as means Ϯ SD.…”

Section: Biological Measurementsmentioning

confidence: 99%