21260-41-3Relevant articles and documents
Photobiological studies of new cyclopentene-psoralens
Dalla Via, Lisa,Gia, Ornella,Viola, Giampietro,Bertoloni, Giulio,Santana, Lourdes,Uriarte, Eugenio
, p. 638 - 644 (1998)
Psoralen analogues bearing a cyclopentane ring fused to either the 4',5' double bond (compound 4) or the 3,4 double bond (compound 7) of the tricyclic furocoumarin structure were prepared. AM1 theoretical calculations performed for these compounds indicated that the electronic properties of their reactive double bonds were very similar to those of psoralen and its derivative 8-methoxypsoralen (8-MOP), though the overall molecular geometries were clearly different, particularly as regards the change in molecular curvature produced by the introduction of the cyclopentane ring. Compound 4 showed a capacity similar to that of 8-MOP to inhibit the growth of human cervix adenocarcinoma cells (HeLa) and to induce mutagenic effects, but it was definitely less phototoxic to skin than 8-MOP. Its ability to photoadd to DNA and to cross-link DNA strands was also demonstrated. Instead, compound 7 was practically devoid of biological activity and no interaction with the macromolecule could be detected. These differences in behaviour between 4 and 7 are probably due to the molecular curvature resulting from the introduction of the cyclopentane ring.
Anti-influenza activity of monoterpene-containing substituted coumarins
Khomenko, Tatyana M.,Zarubaev, Vladimir V.,Orshanskaya, Iana R.,Kadyrova, Renata A.,Sannikova, Victoria A.,Korchagina, Dina V.,Volcho, Konstantin P.,Salakhutdinov, Nariman F.
, p. 2920 - 2925 (2017)
Compounds simultaneously carrying the monoterpene and coumarin moieties have been tested for cytotoxicity and inhibition of activity against influenza virus A/California/07/09 (H1N1)pdm09. The structure of substituents in the coumarin framework, as well as the structure and the absolute configuration of the monoterpenoid moiety, are shown to significantly influence the anti-influenza activity and cytotoxicity of the compounds under study. The compounds with a bicyclic pinane framework exhibit the highest selectivity indices (the ratios between the cytotoxicity and the active dose). The derivative of (?)-myrtenol 15c, which is characterized by promising activity, low cytotoxicity, and synthetic accessibility, has the greatest potential among this group of compounds. It exhibited the highest activity when added to the infected cell culture at early stages of viral reproduction.
Nano-BFn/cellulose: a bio-based nano-catalyst for synthesis of bio-active 7-hydroxycoumarins
Mirjalili, Bi Bi Fatemeh,Bamoniri, Abdolhamid,Fazeli-Attar, Seyede Azita
, p. 839 - 851 (2022/01/20)
Nano-BFn/cellulose as a modified bio-based nano-catalyst has been synthesized from nanocellulose and boron triflouride via very simple steps. This novel nano-catalyst exhibited many advantages in the synthesis of 7-hydroxycoumarins such as good
Monoterpene-containing substituted coumarins as inhibitors of respiratory syncytial virus (Rsv) replication
Borisevich, Sophia S.,Galochkina, Anastasia V.,Khomenko, Tatyana M.,Korchagina, Dina V.,Nikolaeva, Yulia V.,Petukhova, Galina D.,Salakhutdinov, Nariman F.,Shtro, Anna A.,Volcho, Konstantin P.
, (2021/12/24)
Respiratory syncytial virus (RSV) is a critical cause of infant mortality. However, there are no vaccines and adequate drugs for its treatment. We showed, for the first time, that O-linked coumarin–monoterpene conjugates are effective RSV inhibitors. The most potent compounds are active against both RSV serotypes, A and B. According to the results of the time-of-addition experiment, the conjugates act at the early stages of virus cycle. Based on molecular modelling data, RSV F protein may be considered as a possible target.
Coumarin-dithiocarbamate hybrids as novel multitarget AChE and MAO-B inhibitors against Alzheimer's disease: Design, synthesis and biological evaluation
He, Qi,Liu, Jing,Lan, Jin-Shuai,Ding, Jiaoli,Sun, Yongbing,Fang, Yuanying,Jiang, Neng,Yang, Zunhua,Sun, Liyuan,Jin, Yi,Xie, Sai-Sai
supporting information, p. 512 - 528 (2018/09/29)
A series of new coumarin-dithiocarbamate hybrids were designed and synthesized as multitarget agents for the treatment of Alzheimer's disease. Most of them showed potent and clearly selective inhibition towards AChE and MAO-B. Among these compounds, compound 8f demonstrated the most potent inhibition to AChE with IC50 values of 0.0068 μM and 0.0089 μM for eeAChE and hAChE, respectively. Compound 8g was identified as the most potent inhibitor to hMAO-B, and it is also a good and balanced inhibitor to both hAChE and hMAO-B (0.114 μM for hAChE; 0.101 μM for hMAO-B). Kinetic and molecular modeling studies revealed that 8g was a dual binding site inhibitor for AChE and a competitive inhibitor for MAO-B. Further studies indicated that 8g could penetrate the BBB and exhibit no toxicity on SH-SY5Y neuroblastoma cells. More importantly, 8g did not display any acute toxicity in mice at doses up to 2500 mg/kg and could reverse the cognitive dysfunction of scopolamine-induced AD mice. Overall, these results highlighted 8g as a potential multitarget agent for AD treatment and offered a starting point for design of new multitarget AChE/MAO-B inhibitors based on dithiocarbamate scaffold.
Preparation of a novel, efficient, and recyclable magnetic catalyst, γ-Fe2O3@HAp-Ag nanoparticles, and a solvent- and halogen-free protocol for the synthesis of coumarin derivatives
Abbasi, Zahra,Rezayati, Sobhan,Bagheri, Maryam,Hajinasiri, Rahimeh
, p. 75 - 82 (2017/01/13)
In this protocol, Ag supported on the hydroxyapatite-core–shell magnetic γ-Fe2O3nanoparticles (γ-Fe2O3@HAp-Ag NPs) as a novel, efficient, and magnetically recyclable catalyst is synthesized, and characterized by transmission electron microscopy (TEM), scanning electron microscopy (SEM), Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), and vibrating sample magnetometry (VSM). The use of the catalyst is described in the synthesis of coumarin derivatives by the Pechmann condensation of various phenols with β-ketoesters under solvent- and halogen-free conditions at 80?°C. This novel and inexpensive method offers advantages, such as recyclability simple experimental protocol, short reaction time, minimal work-up procedure, and excellent yields of products, together with desirable, eco-friendly, green aspects by avoiding toxic elements and solvents, and ease of recovery from the reaction mixture using an external magnet.
New inhibitors of tyrosyl-DNA phosphodiesterase I (Tdp 1) combining 7-hydroxycoumarin and monoterpenoid moieties
Khomenko, Tatyana,Zakharenko, Alexandra,Odarchenko, Tatyana,Arabshahi, Homayon John,Sannikova, Victoriya,Zakharova, Olga,Korchagina, Dina,Reynisson, Jóhannes,Volcho, Konstantin,Salakhutdinov, Nariman,Lavrik, Olga
, p. 5573 - 5581 (2016/10/24)
A number of derivatives of 7-hydroxycoumarins containing aromatic or monoterpene substituents at hydroxy-group were synthesized based on a hit compound from a virtual screen. The ability of these compounds to inhibit tyrosyl-DNA phosphodiesterase I (Tdp 1), important target for anti-cancer therapy, was studied for the first time. It was found that the 7-hydroxycoumarin derivatives with monoterpene pinene moiety are effective inhibitors of Tdp 1 with the most active derivative (+)-25c with IC50value of 0.675?μM. This compound has low cytotoxicity (CC50?>100?μM) when tested against human cancer cells which is crucial for presupposed application in combination with clinically established anticancer drugs. The ability of the new compounds to enhance the cytotoxicity of camptothecin, an established topoisomerase 1 poison, was demonstrated.
ALICYCLIC[C] BENZOPYRONE DERIVATIVES AND USES THEREOF
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Paragraph 0076, (2014/06/25)
Disclosed are alicyclic[c]benzopyrone derivatives and use thereof. The alicyclic[c]benzopyrone derivatives are compounds represented by formula I or their salts. The present compounds not only significantly improve high activity induced by MK-801, but also effectively improve clambering symptom induced by Apomorphine and do not cause EPS within effective dose. These in vitro targets and in vivo pharmacological models are closely related to diseases of the nervous system caused by dopamine dysfunction, especially schizophrenia. Therefore the present compounds can be used for the treatment of central nervous system diseases, especially schizophrenia. ED50 is lower and effect is stronger in two animal models i.e. high activity induced by MK-801 and clambering symptom induced by Apomorphine, while ED50 is higher and therapeutic index is greater in animal models of catalepsy.
ALICYCLIC[C]BENZOPYRONE DERIVATIVES AND USES THEREOF
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Paragraph 0037, (2014/07/08)
Disclosed are alicyclic[c]benzopyrone derivatives and use thereof. The alicyclic[c]benzopyrone derivatives are compounds represented by formula I or their salts. The present compounds not only significantly improve high activity induced by MK-801, but also effectively improve clambering symptom induced by Apomorphine and do not cause EPS within effective dose. These in vitro targets and in vivo pharmacological models are closely related to diseases of the nervous system caused by dopamine dysfunction, especially schizophrenia. Therefore the present compounds can be used for the treatment of central nervous system diseases, especially schizophrenia. ED50 is lower and effect is stronger in two animal models i.e. high activity induced by MK-801 and clambering symptom induced by Apomorphine, while ED50 is higher and therapeutic index is greater in animal models of catalepsy.
Synthesis and evaluation of new coumarin derivatives as potential atypical antipsychotics
Chen, Yin,Lan, Yu,Wang, Songlin,Zhang, Heng,Xu, Xiangqing,Liu, Xin,Yu, Minquan,Liu, Bi-Feng,Zhang, Guisen
, p. 427 - 439 (2014/02/14)
In this paper, we report the synthesis of novel, potential antipsychotic coumarin derivatives combining potent dopamine D2, D3 and serotonin 5-HT1A, 5-HT2A receptors properties. We describe the structure activity relationship that leads us to the promising derivative: 7-(4-(4-(6-fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)butoxy)-6-methyl-2, 3-dihydrocyclopenta[c]chromen-4(1H)-one 27. The unique pharmacological features of compound 27 are a high affinity for dopamine D2, D3 and serotonin 5-HT1A, 5-HT2A receptors, together with a low affinity for H1 receptor (to reduce the risk of obesity under chronic treatment). In animal models, compound 27 inhibited apomorphine-induced climbing and MK-801-induced hyperactivity without observable catalepsy at the highest dose tested. In particular, compound 27 was more potent than clozapine.
