Biological Evidences of Dicoumarol: A Review

Abstract

Dicoumarol, a natural anticoagulant drug chemically designated as is metabolized from coumarin in the sweet clover (Melilotus alba and Melilotus officinalis) by molds, such as Penicillium nigricans and Penicillium jensi. Coumarin (1,2-benzopyrone), the parent molecule of dicoumarol, is the simplest compound of a large class of naturally occurring phenolic substances made of fused benzene and pyrone rings . In addition, the coumarin anticoagulants, dicoumarol (Dicumarol) and its synthetic derivative warfarin sodium (Coumadin), have been shown to decrease metastases in experimental animals. Warfarin sodium, largely replacing dicoumarol therapeutically as an anticoagulant, has been used for the treatment of a variety of cancers and shown to improve tumor response rates and survival in patients with several types of cancer. However, despite numerous studies, little information has been acquired on the cellular mechanism of action of coumarin compounds in the treatment of malignancies. Possibly for this reason, the coumarin compounds have not received much attention for the treatment of cancer.

l-Proline-catalysed synthesis of chromeno[2,3-b]chromene from 4-hydroxy-2H-chromene-2-thione and an anti-proliferative study

“…1 H and 13 C were recorded using a 400 (100) or 500 (125) MHz spectrometer and were calibrated using residual undeuterated solvent for 1 H NMR and deuterated chloroform for 13 C NMR as an internal reference: CHCl 3 : 7.26 ppm for 1 H NMR and 77.06 ppm for 13 C. The chemical shifts are quoted in δ units, parts per million ( ppm). 1 H NMR data is represented as follows: chemical shift, multiplicity (s = singlet, d = doublet, t = triplet, q = quartet, dd = doublet of doublets, and m = multiplet), integration and coupling constant(s) J in hertz (Hz). The crystal data were collected using a Bruker SMART APEX-II CCD diffractometer.…”

“…After synthesizing all the substrates, a general observation from the results is that the electron-withdrawing group (NO 2 , X) on the benzaldehyde ring facilitates the reaction, giving better results than the electrondonating group (OMe, Me). All the products were characterized by 1 H NMR and 13 C NMR spectroscopy and HRMS spectrometry. Later, we confirmed the linear compound from the X-ray crystallography and it was observed that the sulphur is replaced with an oxygen atom.…”

“…The naturally occurring compounds dicumarol (I) and coumestan (II), derived from 4-hydroxycoumarin, are potent molecules, which exhibit interesting pharmacological activities. [1][2][3] Similarly, the non-natural product warfarin (III), containing a 4-hydroxycoumarin backbone, is used as a medicine for its anticoagulant activity. 4 Moreover, various coumarin compounds display a wide range of biological activities.…”

Dicoumarol: from chemistry to antitumor benefits

“…Dicoumarol is well recognized for its anticoagulant and anti-inflammatory effects, and these properties have been reviewed by other authors [ 21 , 24 ]. For the last years, this has also been highlighted to exert other important bioactive effects [ 21 , 24 ].…”

“…Dicoumarol is well recognized for its anticoagulant and anti-inflammatory effects, and these properties have been reviewed by other authors [ 21 , 24 ]. For the last years, this has also been highlighted to exert other important bioactive effects [ 21 , 24 ]. To further understand these, it is crucial to discuss the chemistry of the compound in relation to its biological properties.…”