82747-36-2 Usage
Description
6,7-Dihydroxy-4-(trifluoromethyl)coumarin is a synthetic derivative of coumarin, a natural compound found in various plants. It features a coumarin core structure with a trifluoromethyl group attached to it and has two hydroxyl groups at positions 6 and 7 of the coumarin ring. This chemical compound possesses potential anticoagulant and antioxidant activities, with the trifluoromethyl group enhancing its lipophilicity and potentially affecting its pharmacokinetic properties. It holds promise for applications in medicinal chemistry, particularly in the development of new pharmaceuticals with anticoagulant and antioxidant properties.
Uses
Used in Pharmaceutical Development:
6,7-Dihydroxy-4-(trifluoromethyl)coumarin is used as a key compound in the development of new pharmaceuticals, specifically for its potential anticoagulant and antioxidant properties. Its unique structure and functional groups contribute to its therapeutic potential, making it a valuable candidate for further research and formulation in the medical field.
Used in Medicinal Chemistry Research:
In the realm of medicinal chemistry, 6,7-dihydroxy-4-(trifluoromethyl)coumarin serves as a subject of study for understanding its interactions with biological targets and its effects on various physiological processes. 6,7-DIHYDROXY-4-(TRIFLUOROMETHYL)COUMARIN's properties can be further optimized and modified to enhance its efficacy and safety in treating specific conditions.
Used in Antioxidant Applications:
6,7-Dihydroxy-4-(trifluoromethyl)coumarin is used as an antioxidant agent, leveraging its potential to combat oxidative stress and related conditions. Its presence in pharmaceutical formulations can help protect cells from damage caused by reactive oxygen species, contributing to overall health and wellness.
Used in Antithrombotic Therapy:
As a compound with potential anticoagulant properties, 6,7-dihydroxy-4-(trifluoromethyl)coumarin is used in antithrombotic therapy to prevent blood clot formation. This can be particularly beneficial in treating and managing conditions such as deep vein thrombosis, pulmonary embolism, and stroke, as well as in the context of cardiovascular surgeries and procedures.
Check Digit Verification of cas no
The CAS Registry Mumber 82747-36-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,2,7,4 and 7 respectively; the second part has 2 digits, 3 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 82747-36:
(7*8)+(6*2)+(5*7)+(4*4)+(3*7)+(2*3)+(1*6)=152
152 % 10 = 2
So 82747-36-2 is a valid CAS Registry Number.
InChI:InChI=1/C10H5F3O4/c11-10(12,13)5-2-9(16)17-8-3-7(15)6(14)1-4(5)8/h1-3,14-15H
82747-36-2Relevant articles and documents
Rational Design of Coumarin Derivatives as CK2 Inhibitors by Improving the Interaction with the Hinge Region
Zhang, Na,Chen, Wen-Juan,Zhou, Yue,Zhao, Hongtao,Zhong, Ru-Gang
, p. 15 - 18 (2016)
Design of novel coumarin derivatives as CK2 inhibitors were attempted by targeting the interaction with the hinge region. A set of substituents capable of forming a hydrogen bond or halogen bond with the hinge region were screened in silico, and trifluoromethyl emerges as a promising motif by forming favorable electrostatic interaction and a presumable halogen bond with the hinge region. As proof of concept, three trifluoromethyl derivatives of coumarin were synthesized and tested in vitro. The results indicated that replacement of methyl by trifluoromethyl leads to a modest 5-fold improvement in potency, with the most active compound being 0.4 μM. The newly designed compounds were further screened on one lung cancer cell line A549, showing low micromolar anti-proliferative activity.
Design, synthesis and biological evaluation of esculetin derivatives as anti-tumour agents
Wang,Xia,Yu, Yang,Lu, Jun-Xia,Zou, Li-Wei,Feng, Lei,Ge, Guang-Bo,Yang, Ling
, p. 53477 - 53483 (2015/06/30)
Esculetin, a naturally catecholic coumarin, possess multiple pharmacological activities including anti-tumour, anti-inflammatory and anti-oxidant. However, the extensive phase II metabolism and rapid elimination from the human body significantly hinder esculetin and its derivatives as drug leads/candidates. To improve both the metabolic stability and the anti-tumour activity of esculetin via rational modification, a series of C-4 and C-8 substituted derivatives were designed and synthesized by perchloric acid catalysed von Pechmann reaction and Mannich reaction, respectively. The in vitro metabolic half-life in human liver S9 and anti-tumour activities in A549 and B16 cell lines of the newly synthesized compounds were assayed. Of these compounds, 8-(pyrrolidin-1-ylmethyl)-4-trifluoromethyl esculetin 15 was the most potent candidate compound, with almost a 20-fold increase in antiproliferative activity and a 3-fold prolonged half-life in human liver S9 compared with the parent compound 1. In addition, the potential structure-activity relationship and structure-metabolic stability relationship were discussed. Notably, the introduction of a nitrogen containing group as a hydrogen bond acceptor at the C-8 position of esculetin can improve both the metabolic stability and anti-tumour activity. All of these findings are very helpful for the structural modification of esculetin and other bioactive phenolic compounds to improve their phase II metabolic stability and bioactivity synchronously.
