72000-18-1Relevant articles and documents
Synthesis, in vitro evaluation and molecular docking studies of novel coumarin-isatin derivatives as α-glucosidase inhibitors
Wang, Guangcheng,Wang, Jing,He, Dianxiong,Li, Xin,Li, Juan,Peng, Zhiyun
, p. 456 - 463 (2017)
This study synthesized a series of novel coumarin-isatin derivatives and evaluated them for α-glucosidase inhibitory activity. The majority of the screened compounds exhibited excellent inhibition activities with IC50 values of 2.56?±?0.08–268.79?±?3.04?μm, when compared to acarbose. Among the newly derivatives, compound 5p was found to be the most active compound in the library of coumarin-isatin derivatives. Furthermore, enzyme kinetic studies showed that compound 5p is a non-competitive inhibitor with a Ki of 2.14?μm. Molecular docking analysis revealed the existence of hydrophobic and hydrogen interactions between compound 5p and the active site of α-glucosidase. Our results indicate that coumarin-isatin derivatives as a new class of α-glucosidase inhibitors.
Dual P-glycoprotein and CA XII inhibitors: A new strategy to reverse the P-gp Mediated Multidrug Resistance (MDR) in cancer cells y
Bartolucci, Gianluca,Braconi, Laura,Bua, Silvia,Coronnello, Marcella,Dei, Silvia,Lapucci, Andrea,Manetti, Dina,Romanelli, Maria Novella,Supuran, Claudiu T.,Teodori, Elisabetta
, (2020/04/17)
A new series of N,N-bis(alkanol)amine aryl diesters was synthesized and studied as dual P-glycoprotein (P-gp) and carbonic anhydrase XII inhibitors (CA XII). These hybrids should be able to synergistically overcome P-gp mediated multidrug resistance (MDR) in cancer cells. It was reported that the effux activity of P-gp could be modulated by CA XII, as the pH reduction caused by CA XII inhibition produces a significant decrease in P-gp ATPase activity. The new compounds reported here feature both P-gp and CA XII binding moieties. These hybrids contain a N,N-bis(alkanol)amine diester scaffold found in P-glycoprotein ligands and a coumarin or benzene sulfonamide moiety to target CA XII. Many compounds displayed a dual activity against P-gp and CA XII being active in the Rhd 123 uptake test on K562/DOX cells and in the hCA XII inhibition test. On LoVo/DOX cells, that overexpress both P-gp and CA XII, some coumarin derivatives showed a high MDR reversal effect in Rhd 123 uptake and doxorubicin cytotoxicity enhancement tests. In particular, compounds 7 and 8 showed higher activity than verapamil and were more potent on LoVo/DOX than on K562/DOX cells overexpressing only P-gp. They can be considered as valuable candidates for selective P-gp/CA XII inhibition in MDR cancer cells.
Synthesis and Biological Evaluation of Substituted Indole and Its Analogs as Influenza A Virus Inhibitors
Zhang, Xuandi,Zhang, Guo-Ning,Wang, Yujia,Zhu, Mei,Wang, Juxian,Li, Ziqiang,Li, Donghui,Cen, Shan,Wang, Yucheng
, (2019/02/07)
Influenza A virus (IAV), a highly pathogenic virus to human beings, is most susceptible to mutation and thus causes rapid, severe global pandemics resulting in millions of fatalities worldwide. Since resistance to the existing anti-influenza drugs is developing, innovative inhibitors with a different mode of action are urgently needed. The lead compound 6092B-E5 has proven to be an effective antiviral reagent in our previous work. Using the principles of substitution and bioisosterism of the indole ring, six series of novel anti-IAV target products were designed, synthesized and evaluated for their antiviral effect in this work. Compounds D1, D3, D9, G1, G3, G12 and G23 were identified as promising anti-IAV candidates with excellent anti-IAV efficacy (IC50 values of 3.06–5.77 μm) and low cytotoxicity (CC50 values up to and beyond 100 μm). This work represents a successful application of the substitution and bioisosteric replacement strategy for the discovery of novel antiviral molecules that can be used for further structural optimization.
Novel 6- and 7-substituted coumarins with inhibitory action against lipoxygenase and tumor-associated carbonic anhydrase IX
Peperidou, Aikaterini,Bua, Silvia,Bozdag, Murat,Hadjipavlou-Litina, Dimitra,Supuran, Claudiu T.
, (2018/01/18)
A series of carboxamide derivatives of 6- and 7-substituted coumarins have been prepared by an original procedure starting from the corresponding 6- or 7-hydroxycoumarins which were alkylated with ethyl iodoacetate, and the obtained ester was converted to the corresponding carboxylic acids which were thereafter reacted with a series of aromatic/aliphatic/heterocyclic amines leading to the desired amides. The new derivatives were investigated as inhibitors of two enzymes, human carbonic anhydrases (hCAs) and soy bean lipoxygenase (LOX). Compounds 4a and 4b were potent LOX inhibitors, whereas many effective hCA IX inhibitors (KIs in the range of 30.2–30.5 nM) were detected in this study. Two compounds, 4b and 5b, showed the phenomenon of dual inhibition. Furthermore, these coumarins did not significantly inhibit the widespread cytosolic isoforms hCA I and II, whereas they were weak hCA IV inhibitors, making them hCA IX-selective inhibitors. As hCA IX and LOX are validated antitumor targets, these results are promising for the investigation of novel drug targets involved in tumorigenesis.
Synthesis and anti-acetylcholinesterase activity of N-[(indolyl)ethyl)- coumarin-yloxy)]alkanamides
Ghanei-Nasab, Sarah,Nadri, Hamid,Moradi, Alireza,Marjani, Azam,Shabani, Shabnam,Firoozpour, Loghman,Moghimi, Setareh,Khoobi, Mehdi,Hadizadeh, Farzin,Foroumadi, Alireza
, p. 120 - 123 (2017/03/15)
Novel coumarin-tryptamine systems attached through a linker were synthesised and evaluated in vitro against acetylcholinesterase by the classical Ellman's test.
Coumarin-isatin type compounds, and preparation method and purpose thereof
-
Paragraph 0010; 0011, (2016/10/08)
The invention discloses a kind of coumarin-isatin type compounds, and a preparation method and a purpose thereof. The compounds possess a structure shown as a formula (I). The preparation method comprises taking 7-hydroxycoumarin and ethyl bromoacetate as raw materials to obtain [(2-oxo-2H-chromen-7-yl)oxy]acetic acid, and then performing hydrazinolysis reaction to obtain [(2-oxo-2H-chromen-7-yl)oxy]acetohydrazide, and finally reacting with various substituted isatins to obtain the corresponding target compounds. The compounds can be used as a raw material of an anti-diabetes medicament, and the preparation method is simple and easily-available in raw material and convenient to operate.
Writing and erasing hidden optical information on covalently modified cellulose paper
D'Halluin,Rull-Barrull,Le Grognec,Jacquemin,Felpin
supporting information, p. 7672 - 7675 (2016/07/06)
An unprecedented strategy for preparing photoresponsive cellulose paper enabling the storage of short-lived optical data by covalent photopatterning is disclosed. An ab initio design hinting that the covalent grafting of coumarins on the paper could yield valuable photoresponsive units was first performed. Second, light sensitive paper that can be reversibly altered upon irradiation at a specific wavelength was prepared by covalent surface functionalization with coumarins. Third, the validity of this strategy is demonstrated using the photolithography of several gripping patterns such as a dynamic QR code.
Semisynthesis, ex vivo evaluation, and SAR studies of coumarin derivatives as potential antiasthmatic drugs
Sánchez-Recillas, Amanda,Navarrete-Vázquez, Gabriel,Hidalgo-Figueroa, Sergio,Rios, María Yolanda,Ibarra-Barajas, Maximiliano,Estrada-Soto, Samuel
, p. 400 - 408 (2014/04/17)
Asthma is a chronic inflammatory disorder that causes contraction in the smooth muscle of the airway and blocking of airflow. Reversal the contractile process is a strategy for the search of new drugs that could be used for the treatment of asthma. This work reports the semisynthesis, ex vivo relaxing evaluation and SAR studies of a series of 18 coumarins. The results pointed that the ether derivatives 1-3, 7-9 and 13-15 showed the best activity (E max = 100%), where compound 2 (42 μM) was the most potent, being 4-times more active than theophylline (positive control). The ether homologation (methyl, ethyl and propyl) in position 7 or positions 6 and 7 of coumarins lead to relaxing effect, meanwhile formation of esters generated less active compounds than ethers. The SAR analysis showed that it is necessary the presence of two small ether groups and the methyl group at position 4 (site 3) encourage biological activity through soft hydrophobic changes in the molecule, without drastically affecting the cLogP.
Synthesis and anti-cholinesterase activity of new 7-hydroxycoumarin derivatives
Alipour, Masoumeh,Khoobi, Mehdi,Moradi, Alireza,Nadri, Hamid,Homayouni Moghadam, Farshad,Emami, Saeed,Hasanpour, Zeinab,Foroumadi, Alireza,Shafiee, Abbas
, p. 536 - 544 (2014/07/07)
A series of 7-hydroxycoumarin derivatives connected by an amidic linker to the different amines were designed and synthesized as cholinesterase inhibitors. Most compounds showed remarkable inhibitory activity against acetylcholinesterase (AChE) and butyry
Synthesis, antimicrobial and antioxidant activities of 5-((2-oxo-2H- chromen-7-yloxy)methyl)-1,3,4-thiadiazol-2(3H)-one derived from umbelliferone
Al-Amiery, Ahmed A.,Al-Temimi, Ali A.,Sulaiman, Ghassan M.,Aday, Hamdan A.,Kadhum, Abdul Amir Hassan,Mohamad, Abu Bakar
, p. 950 - 954 (2013/04/23)
5-((2-Oxo-2H-chromen-7-yloxy)methyl)-1,3,4-thiadiazol-2(3H)-one was synthesized and characterized by FT-IR and NMR spectra in addition to elemental analysis. The prepared compound shows considerable antibacterial and antifungal activity. The free radical scavenging activity of the synthesized compound was screened for in vitro antioxidant activity.
