66267-82-1Relevant academic research and scientific papers
Synthesis and evaluation of two coumarin-type derivatization reagents for fluorescence detection of chiral amines and chiral carboxylic acids
Mertens, Matthias D.,Guetschow, Michael
, p. 957 - 964 (2013)
The synthesis of two fluorescent coumarin-type chiral derivatization agents (4 and 11) is reported. A chiral side chain was introduced at position 7 of the coumarin via Mitsunobu reaction. The two coumarins bear in this side chain either a free amino group or a carboxyl group, making them useful for further transformations. Conjugates of chiral prototype drugs with 4 or 11 were prepared by amide coupling of the analyte's carboxyl group to the reagent's amine group, or vice versa. The separation of seven diastereomeric conjugates through achiral high-performance liquid chromatography (HPLC) on a common C18 column is demonstrated. Chirality 25:957-964, 2013. 2013 Wiley Periodicals, Inc.
3-aryl coumarin derivative as well as preparation method and application thereof
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Paragraph 0193-0198, (2021/07/17)
The invention discloses a 3-aryl coumarin derivative as well as a preparation method and application thereof. The preparation method comprises the following steps of: carrying out tandem condensation-lactonization reaction on substituted phenylacetic acid
7-Hydroxycoumarins Are Affinity-Based Fluorescent Probes for Competitive Binding Studies of Macrophage Migration Inhibitory Factor
Xiao, Zhangping,Chen, Deng,Song, Shanshan,Van Der Vlag, Ramon,Van Der Wouden, Petra E.,Van Merkerk, Ronald,Cool, Robbert H.,Hirsch, Anna K. H.,Melgert, Barbro N.,Quax, Wim J.,Poelarends, Gerrit J.,Dekker, Frank J.
, p. 11920 - 11933 (2020/11/26)
Macrophage migration inhibitory factor (MIF) is a cytokine with key roles in inflammation and cancer, which qualifies it as a potential drug target. Apart from its cytokine activity, MIF also harbors enzyme activity for keto-enol tautomerization. MIF enzymatic activity has been used for identification of MIF binding molecules that also interfere with its biological activity. However, MIF tautomerase activity assays are troubled by irregularities, thus creating a need for alternative methods. In this study, we identified a 7-hydroxycoumarin fluorophore with high affinity for the MIF tautomerase active site (Ki = 18 ± 1 nM) that binds with concomitant quenching of its fluorescence. This property enabled development of a novel competition-based assay format to quantify MIF binding. We also demonstrated that the 7-hydroxycoumarin fluorophore interfered with the MIF-CD74 interaction and inhibited proliferation of A549 cells. Thus, we provide a high-affinity MIF binder as a novel tool to advance MIF-oriented research.
Synthesis and biological evaluation of 3-arylcoumarin derivatives as potential anti-diabetic agents
Hu, Yuheng,Wang, Bing,Yang, Jie,Liu, Teng,Sun, Jie,Wang, Xiaojing
, p. 15 - 30 (2018/10/31)
A variety of substituted 3-arylcoumarin derivatives were synthesised through microwave radiation heating. The method has characteristics of environmental friendliness, economy, simple separation, and purification process, less by-products and high reaction yield. Those 3-arylcoumarin derivatives were screened for antioxidant, α-glucosidase inhibitory and advanced glycation end-products (AGEs) formation inhibitory. Most compounds exhibited significant antioxidant and AGEs formation inhibitory activities. Anti-diabetic activity studies showed that compounds 11 and 17 were equipotent to the standard drug glibenclamide in vivo. According to the experimental results, the target compound 35 can be used as a lead compound for the development of new anti-diabetic drugs. The whole experiment showed that anti-diabetic activity is prevalent in 3-arylcoumarins, which added a new natural skeleton to the development of anti-diabetic active drugs.
Synthesis and biological evaluation of 3-arylcoumarins as potential anti-Alzheimer's disease agents
Yang, Jie,Zhang, Pingping,Hu, Yuheng,Liu, Teng,Sun, Jie,Wang, Xiaojing
, p. 651 - 656 (2019/02/19)
Alzheimer's disease, a neurodegenerative illness, has the extremely complex pathogenesis. Accumulating evidence indicates there is a close relationship between several enzymes and Alzheimer's disease. Various substituted 3-arylcoumarin derivatives were synthesised, and their in vitro activity, including cholinesterase inhibitory activity, monoamine oxidase inhibitory activity, and antioxidant activity were investigated. Most of the compounds exhibited high activity; therefore 3-arylcoumarin compounds have the potential as drug candidates for the treatment of Alzheimer's disease.
3-Aryl Coumarin Derivatives Bearing Aminoalkoxy Moiety as Multi-Target-Directed Ligands against Alzheimer's Disease
Abdshahzadeh, Helia,Golshani, Mostafa,Nadri, Hamid,Saberi Kia, Iraj,Abdolahi, Zahra,Forootanfar, Hamid,Ameri, Alieh,Tüylü Kü?ükk?l?n?, Tuba,Ayazgok, Beyza,Jalili-Baleh, Leili,Sadat Ebrahimi, Seyed Esmaeil,Moghimi, Setareh,Haririan, Ismaeil,Khoobi, Mehdi,Foroumadi, Alireza
, (2019/04/17)
Two series of novel coumarin derivatives, substituted at 3 and 7 positions with aminoalkoxy groups, are synthesized, characterized, and screened. The effect of amine substituents and the length of cross-linker are investigated in acetyl- and butyrylcholin
Decarboxylation of α,β-unsaturated aromatic lactones: Synthesis of: E-ortho -hydroxystilbenes from 3-arylcoumarins or isoaurones
Huang, Xihua,Liu, Jie,Sheng, Jianfei,Song, Xianheng,Du, Zhibo,Li, Mingkang,Zhang, Xuejing,Zou, Yong
supporting information, p. 804 - 808 (2018/03/06)
A simple and environmentally friendly strategy for the synthesis of E-ortho-hydroxystilbenes has been established. Two kinds of α,β-unsaturated aromatic lactones, i.e. the 3-arylcoumarins and the isoaurones, could both readily undergo a cascade hydrolyzation/decarboxylation reaction in the presence of KOH in ethylene glycol to afford the desired E-ortho-hydroxystilbenes in moderate to high yields.
Molecular Docking-Based Design and Development of a Highly Selective Probe Substrate for UDP-glucuronosyltransferase 1A10
Juvonen, Risto O.,Rauham?ki, Sanna,Kortet, Sami,Niinivehmas, Sanna,Troberg, Johanna,Petsalo, Aleksanteri,Huuskonen, Juhani,Raunio, Hannu,Finel, Moshe,Pentik?inen, Olli T.
, p. 923 - 933 (2018/03/13)
Intestinal and hepatic glucuronidation by the UDP-glucuronosyltransferases (UGTs) greatly affect the bioavailability of phenolic compounds. UGT1A10 catalyzes glucuronidation reactions in the intestine, but not in the liver. Here, our aim was to develop se
Design, synthesis and evaluation of novel multi-target-directed ligands for treatment of Alzheimer's disease based on coumarin and lipoic acid scaffolds
Jalili-Baleh, Leili,Forootanfar, Hamid,Kü?ükk?l?n?, Tuba Tüylü,Nadri, Hamid,Abdolahi, Zahra,Ameri, Alieh,Jafari, Mandana,Ayazgok, Beyza,Baeeri, Maryam,Rahimifard, Mahban,Abbas Bukhari, Syed Nasir,Abdollahi, Mohammad,Ganjali, Mohammad Reza,Emami, Saeed,Khoobi, Mehdi,Foroumadi, Alireza
, p. 600 - 614 (2018/06/26)
A novel series of coumarin-lipoic acid conjugates were synthesized via cycloaddition click reaction to find out new multi-target-directed ligands (MTDLs) for treatment of Alzheimer's disease (AD). All of synthesized compounds were screened for neuroprotec
Fatty Acid Amide Hydrolase (FAAH), Acetylcholinesterase (AChE), and Butyrylcholinesterase (BuChE): Networked Targets for the Development of Carbamates as Potential Anti-Alzheimer's Disease Agents
Montanari, Serena,Scalvini, Laura,Bartolini, Manuela,Belluti, Federica,Gobbi, Silvia,Andrisano, Vincenza,Ligresti, Alessia,Di Marzo, Vincenzo,Rivara, Silvia,Mor, Marco,Bisi, Alessandra,Rampa, Angela
supporting information, p. 6387 - 6406 (2016/07/26)
The modulation of the endocannabinoid system is emerging as a viable avenue for the treatment of neurodegeneration, being involved in neuroprotective and anti-inflammatory processes. In particular, indirectly enhancing endocannabinoid signaling to therapeutic levels through FAAH inhibition might be beneficial for neurodegenerative disorders such as Alzheimer's disease, effectively preventing or slowing the progression of the disease. Hence, in the search for a more effective treatment for Alzheimer's disease, in this paper, the multitarget-directed ligand paradigm was applied to the design of carbamates able to simultaneously target the recently proposed endocannabinoid system and the classic cholinesterase system, and achieve effective dual FAAH/cholinesterase inhibitors. Among the two series of synthesized compounds, while some derivatives proved to be extremely potent on a single target, compounds 9 and 19 were identified as effective dual FAAH/ChE inhibitors, with well-balanced nanomolar activities. Thus, 9 and 19 might be considered as new promising candidates for Alzheimer's disease treatment.
