81017-24-5Relevant academic research and scientific papers
Synthesis of xanthene and coumarin derivatives in water by using β-Cyclodextrin
Kamat, Siddharth R.,Mane, Ananda H.,Patil, Audumbar D.,Lohar, Trushant R.,Salunkhe, Rajashri S.
, p. 911 - 924 (2020/11/09)
Simple and green procedure was developed for the synthesis of various xanthene and coumarin derivatives using beta-cyclodextrin (β-CD) as reusable catalyst at 70?°C in water. Condensation of salicylaldehyde (1?mmol) and dimedone (2?mmol) or 1,3 cyclohexadione (2?mmol) gave corresponding xanthene derivatives, while condensation of salicylaldehyde (1?mmol) with Meldrum’s acid (1?mmol) or 4-Hydroxy-6-methyl-2H-pyran-2-one (1?mmol) gave respective coumarin derivatives in impressive yields. Involvement of β-CD as catalyst was ascertained by inclusion complex evaluation of β-CD-salicylaldehyde with 1H NMR analysis at 70?°C. Graphic abstract: [Figure not available: see fulltext.].
Evaluation of novel N′-(3-hydroxybenzoyl)-2-oxo-2H-chromene-3-carbohydrazide derivatives as potential HIV-1 integrase inhibitors
Jesumoroti, Omobolanle J.,Faridoon,Mnkandhla, Dumisani,Isaacs, Michelle,Hoppe, Heinrich C.,Klein, Rosalyn
, p. 80 - 88 (2019/01/30)
In an attempt to identify potential new agents that are active against HIV-1 IN, a series of novel coumarin-3-carbohydrazide derivatives were designed and synthesised. The toxicity profiles of these compounds showed that they were non-toxic to human cells and they exhibited promising anti-HIV-1 IN activities with IC50 values in nM range. Also, an accompanying molecular modeling study showed that the compounds bind to the active pocket of the enzyme.
Peptides N-connected to hydroxycoumarin and cinnamic acid derivatives: Synthesis and fluorescence spectroscopic, antioxidant and antimicrobial properties
Ghalehshahi, Hajar G.,Balalaie, Saeed,Aliahmadi, Atousa
, p. 8831 - 8842 (2018/06/11)
The tripeptide Tyr-Gly-Ser and a series of conjugations to coumarin, cinnamic and gallic acid were synthesized in salt form and their antioxidant and antimicrobial activities were investigated. The N-connecting hydroxycoumarin, cinnamic and gallic acid derivatives to peptides and the use of BBr3 as a demethylating agent for peptides was reported. Their activities were investigated based on the conjugated moiety structures. Studies of their activities showed that conjugated tripeptides 7,8-dihydroxycoumarin-peptide (17), caffeic acid-peptide (22) and gallic acid-peptide (28) were found to be superior to ascorbic acid with respect to their antioxidant activity, and 12, 14, 24, and 25 exhibited the most antimicrobial activity in the series compared to amoxicillin. Additionally, the incredible florescence intensity and brightness of 17 in water and DMSO, compared to other synthesized compounds, qualified this peptide as a suitable probe in the human body.
Design, synthesis and biological evaluation of novel coumarin-based benzamides as potent histone deacetylase inhibitors and anticancer agents
Abdizadeh, Tooba,Kalani, Mohammad Reza,Abnous, Khalil,Tayarani-Najaran, Zahra,Khashyarmanesh, Bibi Zahra,Abdizadeh, Rahman,Ghodsi, Razieh,Hadizadeh, Farzin
, p. 42 - 62 (2017/03/24)
Histone deacetylases (HDACs) are attractive therapeutic targets for the treatment of cancer and other diseases. It has four classes (I-IV), among them especially class I isozyme are involved in promoting tumor cells proliferation, angiogenesis, differentiation, invasion and metastasis and also viable targets for cancer therapeutics. A novel series of coumarin-based benzamides was designed and synthesized as HDAC inhibitors. The cytotoxic activity of the synthesized compounds (8a-u) was evaluated against six human cancer cell lines including HCT116, A2780, MCF7, PC3, HL60 and A549 and a single normal cell line (Huvec). We evaluated their inhibitory activities against pan HDAC and HDAC1 isoform. Four compounds (8f, 8q, 8r and 8u) showed significant cytotoxicity with IC50 in the range of 0.53–57.59?μM on cancer cells and potent pan-HDAC inhibitory activity (consists of HDAC isoenzymes) (IC50?=?0.80–14.81?μM) and HDAC1 inhibitory activity (IC50?=?0.47–0.87?μM and also, had no effect on Huvec (human normal cell line) viability (IC50?>?100?μM). Among them, 8u displayed a higher potency for HDAC1 inhibition with IC50 value of 0.47?±?0.02?μM near equal to the reference drug Entinostat (IC50?=?0.41?±?0.06?μM). Molecular docking studies and Molecular dynamics simulation of compound 8a displayed possible mode of interaction between this compound and HDAC1enzyme.
Silver-Mediated Oxidative Decarboxylative Trifluoromethylthiolation of Coumarin-3-carboxylic Acids
Li, Minghao,Petersen, Jeffrey L.,Hoover, Jessica M.
supporting information, p. 638 - 641 (2017/02/10)
The introduction of trifluoromethylthio groups into organic compounds, in particular heterocycles, is important because of the prevalence of these structures in medicinally and agriculturally relevant molecules. Herein, the silver-mediated oxidative decarboxylative trifluoromethylthiolation of coumarin-3-carboxylic acids is reported. This methodology utilizes existing carboxylic acid functionalities for the direct conversion to CF3S groups and results in a broad scope of 3-trifluoromethylthiolated coumarins, including analogues of natural products, in moderate to excellent yields.
3-substituted coumarin derivatives and their use
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Paragraph 0094; 0095; 0096, (2016/10/08)
The invention provides a 3-substituted coumarin derivative, and pharmaceutically acceptable salts, solvates, hydrates or crystal forms thereof. The above compound has a high calcium flow activity and a very good selectivity on a human derived cannabinoid receptor CB2, and is a specific agonist or inverse agonist of the cannabinoid receptor CB2. The compound is an active ligand of a novel cannabinoid II receptor CB2, and compounds of the above kind and pharmaceutically acceptable salts, solvates, hydrates or crystal forms thereof have high calcium flow activities and a very good selectivity on the human derived cannabinoid receptor CB2. The compound is the specific agonist or inverse agonist of the cannabinoid receptor CB2, and can be applied to the preparation of medicines for treating, preventing and inhibiting CB2 receptor mediated diseases. The structure of the derivative is represented by a general formula A shown in the specification.
Design, syntheses, structure - Activity relationships and docking studies of coumarin derivatives as novel selective ligands for the CB2 receptor
Han, Shuang,Zhang, Fei-Fei,Qian, Hai-Yan,Chen, Li-Li,Pu, Jian-Bin,Xie, Xin,Chen, Jian-Zhong
, p. 16 - 32 (2015/03/05)
The CB2 receptor has been considered as an inspiring drug target for the treatment of pain and immune-related diseases. In the current manuscript, a novel series of coumarin derivatives is reported to be designed and synthesized by combining the structural features of some known ligands for the cannabinoid receptors based on the CoMFA model of the lead compounds. The compounds were evaluated to be highly selective ligands for the CB2 receptor over the CB1 receptor by calcium mobilization assays. Furthermore, SAR results Therefore, molecular docking simulations were performed to calculate the receptor-ligand interactions of our synthesized compounds binding to the CB2 receptor. The understanding of the binding modes could be advantageous for further development of selective ligands for the CB2 receptor.
Novel penicillin derivatives containing a coumarin nucleus and medicines containing the same
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, (2008/06/13)
This invention provides novel penicillin derivatives of formula [I]; STR1 wherein A is hydrogen or hydroxyl, and B represents the cumarin nucleus of formula [III-a]; STR2 in which B1, B2, B3, B4 and B5/sub
