- 3-Hydroxy-7,8,9,10-tetrahydro-6H-benzo[c]chromen-6-one and 3-hydroxy-6H-benzo[c] chromen-6-one act as on-off selective fluorescent sensors for Iron (III) under in vitro and ex vivo conditions
-
Regarding the abundant use of metals for different purposes, it becomes more critical from various scientific and technological perspectives to discover novel agents as selective probes for the detection of specific metals. In our previous studies, we have shown that aqueous solutions of natural urolithins (i.e., hydroxyl-substituted benzo[c]chromen-6-one derivatives) are selective Iron (III) sensors in fluorescence assays. In this study, we have extrapolated these findings to another coumarine compound (i.e., 3-Hydroxy-7,8,9,10- tetrahydro-6H-benzo[c]chromen-6-one) and compared the selective metal binding properties with Urolithin B (i.e., 3-Hydroxy-6H-benzo[c]chromen-6-one). Following the synthesis and structure identification studies, the fluorometric studies pointed out that the lactam group in the structure still persists to be the important scaffold for maintaining selective on-off sensor capacity that renders the compound a selective Iron (III) binding probe. Moreover, for the first time, fluorescence cellular imaging studies concomitant to cytotoxicity assays with the title compounds were also performed and the results displayed the cell-penetrative, safe, and fluorescent detectable characteristics of the compounds in neuroblastoma and glioblastoma cells through servings as intracellular Iron (III) on-off sensors.
- FALLAH, Amirhossein,GüLCAN, Hayrettin Ozan,GAZI, Mustafa,KALKAN, Rasime,SHUKUR, Karar,TERALI, Kerem
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p. 858 - 867
(2021/07/26)
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- Synthesis of Fluorescent Probes Targeting Tumor-Suppressor Protein FHIT and Identification of Apoptosis-Inducing FHIT Inhibitors
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For the early diagnosis of cancer, leading to a better chance of full recovery, marker genes whose expression is already altered in precancerous lesions are desirable, and the tumor-suppressor gene FHIT is one candidate. The gene product, FHIT protein, has a unique dinucleoside triphosphate hydrolase (AP3Aase) activity, and in this study, we designed and synthesized a series of FHIT fluorescent probes utilizing this activity. We optimized the probe structure for high and specific reactivity with FHIT and applied the optimized probe in a screening assay for FHIT inhibitors. Screening of a compound library with this assay identified several hits. Structural development of a hit compound afforded potent FHIT inhibitors. These inhibitors induce apoptosis in FHIT-expressing cancers via caspase activation. Our results support the idea that FHIT binders, no matter whether inhibitors or agonists of AP3Aase activity, might be promising anticancer agents.
- Kawaguchi, Mitsuyasu,Sekimoto, Eriko,Ohta, Yuhei,Ieda, Naoya,Murakami, Takashi,Nakagawa, Hidehiko
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supporting information
p. 9567 - 9576
(2021/07/19)
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- Design, synthesis, and biological evaluation of new urolithin amides as multitarget agents against Alzheimer's disease
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A series of urolithin amide (i.e., URO-4–URO-10 and THU-4–THU-10) derivatives was designed and synthesized, and their chemical structures were confirmed with spectroscopic techniques and elemental analysis. The title compounds and synthesis intermediates
- Shukur, Karar T.,Ercetin, Tugba,Luise, Chiara,Sippl, Wolfgang,Sirkecioglu, Okan,Ulgen, Mert,Coskun, Goknil P.,Yarim, Mine,Gazi, Mustafa,Gulcan, Hayrettin O.
-
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- Monoterpene-containing substituted coumarins as inhibitors of respiratory syncytial virus (Rsv) replication
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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.
- 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.
-
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- Umbelliferyloxymethyl phosphonate compounds-weakly binding zinc ionophores with neuroprotective properties
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Umbelliferone is a member of the coumarin family of compounds which are known for diverse pharmacological activity including in targets relevant to Alzheimers disease, AD. The toxicity associated with some forms of the amyloid protein, Aβ, and the role of Zn2+ (and other biometals) dyshomeostasis in this, are of great interest in AD and make metal ionophore capability desirable in so called multi target drug ligands MTDLs. A new series of umbelliferyloxymethyl phosphonic acid diethylester compounds (umbelliferyloxymethyl phosphonates) bearing a phosphonate at the 7-position (compounds 1, 3-6), hydrolysis products 2, 2a and 2b from 1 and analogues 7 and 8 of 1 with 7-O to 7-S and 1-O to 1-NH substitutions, are reported. Single crystal X-ray structures of compounds 1, 2 and 2a were determined. In terms of neuroprotective properties, the compounds 1, 2, 3, 4, 5 and 6 at 1 μM concentration, inhibited the toxicity of Aβ1-42 (Aβ42) in both toxic Amyloid Derived Diffusible Ligand (ADDL) and fibrillar (fibril) forms towards rat hippocampal cells. Compound 7 displayed cytotoxicity and 8 failed to inhibit Aβ42 toxicity. Concerning compound-metal ionophore activity (assessed using chemical experiments), despite weak binding to Zn2+ determined from 31P NMR titration of 1 and 2 by ZnCl2, compounds 1, 3, 4, 5 and 6 demonstrated ionophore assisted partition of Zn2+ from water to octanol at micromolar concentrations with efficacy on a par with or better than the chelator MTDL clioquinol (5-chloro-7-iodo-8-hydroxyquinoline). Partition was assessed using furnace Atomic Absorption Spectroscopy (AAS). In further experiments interaction of compound 1 with Zn2+ or it's pathways was inferred by (i) delayed fluorescence response with added Zn2+ in cells treated with FluoZin-3 and (ii) by suppression of Zn2+ promoted aggregation of Aβ42.
- Connole, Laura,Guesne, Sebastien,Kim, Stephanie,Michael-Titus, Adina T.,Motevalli, Majid,Robson, Lesley,Sullivan, Alice
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supporting information
p. 17041 - 17051
(2021/12/10)
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- Coumarin-dithiocarbamate hybrids as novel multitarget AChE and MAO-B inhibitors against Alzheimer's disease: Design, synthesis and biological evaluation
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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.
- He, Qi,Liu, Jing,Lan, Jin-Shuai,Ding, Jiaoli,Sun, Yongbing,Fang, Yuanying,Jiang, Neng,Yang, Zunhua,Sun, Liyuan,Jin, Yi,Xie, Sai-Sai
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p. 512 - 528
(2018/09/29)
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- Design, synthesis and characterization of novel urolithin derivatives as cholinesterase inhibitor agents
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Background: Considering the limitations of current cholinesterase inhibitor drugs for the treatment of Alzheimer’s disease, there is ongoing research activities to find out alternative drug candidates. The aryl-spacer-N-benzyl pharmacophore model has been effectively utilized to design various types of cholinesterase inhibitor molecules, including donepezil. Within this research study, we have questioned the significance of the benzyl group within this pharmacophore employing the urolithin derivatives. Urolithins are benzo[c]chromene analogue metabolites of ellagitannins, abundantly found in pomegranate and berry fruits. Methods: Employing the previous experience that urolithin-spacer-N-benzyl yielded out potent cholinesterase inhibitors, we have designed novel benzo[c]chromene derivatives either lacking the benzyl group or possessing benzyl group in isoquinoline moiety lacking free N-C bond rotation. Following the synthesis and structure identification studies the compounds were screened for their potential to inhibit cholinesterase enzymes. Furthermore, the title compounds were also evaluated for their potential to prevent cholinesterase-accelerated amyloid beta aggregation. In the final, the most active compound was examined to find out its interactions with the cholinesterase enzyme employing a molecular docking study. Results: The title compounds displayed varying cholinesterase inhibitory potential. Some of the compounds were found more / comparable activity to the activity of the current drugs employed in clinic. The potential of the title molecules to inhibit amyloid beta aggregation was found poor. Conclusion: The title compounds displayed varying cholinesterase inhibitory potential, implying that the benzyl group is not a must in each design. This was also shown with the molecular docking studies. On the other hand, the beta amyloid aggregation studies have pointed out that cholinesterase inhibition does not guarantee the prevention of cholinesterase-accelerated amyloid beta aggregation.
- Norouzbahari, Maryam,Burgaz, Emine V.,Ercetin, Tugba,Fallah, Amirhossein,Foroumadi, Alireza,Firoozpour, Loghman,Sahin, Mustafa F.,Gazi, Mustafa,Gulcan, Hayrettin O.
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p. 1131 - 1140
(2018/11/01)
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- Anti-influenza activity of monoterpene-containing substituted coumarins
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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.
- Khomenko, Tatyana M.,Zarubaev, Vladimir V.,Orshanskaya, Iana R.,Kadyrova, Renata A.,Sannikova, Victoria A.,Korchagina, Dina V.,Volcho, Konstantin P.,Salakhutdinov, Nariman F.
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supporting information
p. 2920 - 2925
(2017/06/01)
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- New inhibitors of tyrosyl-DNA phosphodiesterase I (Tdp 1) combining 7-hydroxycoumarin and monoterpenoid moieties
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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.
- Khomenko, Tatyana,Zakharenko, Alexandra,Odarchenko, Tatyana,Arabshahi, Homayon John,Sannikova, Victoriya,Zakharova, Olga,Korchagina, Dina,Reynisson, Jóhannes,Volcho, Konstantin,Salakhutdinov, Nariman,Lavrik, Olga
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p. 5573 - 5581
(2016/10/24)
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- Multi-target tacrine-coumarin hybrids: Cholinesterase and monoamine oxidase B inhibition properties against Alzheimer's disease
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A series of novel tacrine-coumarin hybrids were designed, synthesized and evaluated as multi-target agents against Alzheimer's disease. The biological assays indicated that most of compounds displayed potent inhibitory activity toward AChE and BuChE, and clearly selective inhibition for MAO-B. Among these compounds, 14c exhibited strong inhibitory activity for AChE (IC50 values of 33.63 nM for eeAChE and 16.11 nM for hAChE) and BuChE (IC50 values of 80.72 nM for eqBuChE and 112.72 nM for hBuChE), and the highest inhibitory activity against hMAO-B (IC50 value of 0.24 11/4M). Kinetic and molecular modeling studies revealed that 14c was a mixed-type inhibitor, binding simultaneously to catalytic, peripheral and mid-gorge sites of AChE. It was also a competitive inhibitor, which covered the substrate and entrance cavities of MAO-B. Moreover, 14c could penetrate the CNS and show low cell toxicity. Overall, these results suggested that 14c might be an excellent multi-target agent for AD treatment.
- Xie, Sai-Sai,Wang, Xiaobing,Jiang, Neng,Yu, Wenying,Wang, Kelvin D.G.,Lan, Jin-Shuai,Li, Zhong-Rui,Kong, Ling-Yi
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supporting information
p. 153 - 165
(2015/03/31)
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- Phosphate tricyclic coumarin analogs as steroid sulfatase inhibitors: Synthesis and biological activity
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In the present work, we report convenient methods for the synthesis and biological evaluation of phosphate tricyclic coumarin derivatives as potential steroid sulfatase inhibitors. The described synthesis includes the straightforward preparation of 7-hydroxy-2,3-dihydro-1H-cyclopenta[c]chromen-4-one, 3-hydroxy-7,8,9,10-tetrahydro-6H-benzo[c]chromen-6-one and 3-hydroxy-8,9,10,11-tetrahydro-7H-cyclohepta[c]chromen-6-one modified with various phosphate moieties. The inhibitory effects of the synthesized compounds were tested on STS isolated from human placenta as well as the MCF-7, MDA-MB-231 and MDA-MB-435S cancer cell lines. Most of the new STS inhibitors possessed IC50 values between 21 to 159 μM. In the course of our investigation, the largest inhibitory effects in the STS enzyme assays were observed for the three compounds 9p, 9r and 9s, with IC50 values of 36.4, 37.8 and 21.5 μM, respectively (IC50 value of 1.0 μM for the 665-COUMATE used as a reference). The compound 9r, exhibited the highest potency against MCF-7, an estrogen receptor positive (ER+) cell line, with a GI50 value of 24.7 μM. The structure-activity relationships of the synthesized coumarin derivatives with the STS enzyme are discussed.
- Kozak, Witold,Dasko, Mateusz,Maslyk, Maciej,Pieczykolan, Jerzy S.,Gielniewski, Bartlomiej,Rachon, Janusz,Demkowicz, Sebastian
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p. 44350 - 44358
(2014/12/10)
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- Synthesis and evaluation of new coumarin derivatives as potential atypical antipsychotics
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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.
- Chen, Yin,Lan, Yu,Wang, Songlin,Zhang, Heng,Xu, Xiangqing,Liu, Xin,Yu, Minquan,Liu, Bi-Feng,Zhang, Guisen
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p. 427 - 439
(2014/02/14)
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- 3-SUBSTITUTED-6H-BENZO[C]CHROMEN-6-ONES AND 3-SUBSTITUTED-7,8,9,10-TETRAHYDRO-6H-BENZO[C]CHROMEN-6-ONES AGAINST SENILE DEMENTIA
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This invention is related with the conversion of xenobiotics to potent ACHE and BCHE inhibitors that have activity comparable to the current ACHE and BCHE inhibitor drugs (i.e., donepezil, rivastigmine, and galantamine).
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Page/Page column 12-13
(2014/09/03)
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- Design, synthesis and biological evaluation of novel 6H-benzo[c]chromen-6-one, and 7,8,9,10-tetrahydro-benzo[c]chromen-6-one derivatives as potential cholinesterase inhibitors
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Hydroxylated 6H-benzo[c]chromen-6-one derivatives (i.e., urolithins) are the main bioavailable metabolites, and biomarkers of ellagitannins present in various nutrition. Although these dietaries, the sources of urolithins, are employed in folk medicine as cognitive enhancer in the treatment of Alzheimer's Disease, urolithins have negligible potential to inhibit acetylcholinesterase and butyrylcholinesterase enzymes, the validated targets of Alzheimer's Disease. Therefore, within this research, a series of 6H-benzo[c]chromen-6-one, and 7,8,9,10-tetrahydro-benzo[c]chromen-6-one derivatives has been designed, synthesized, and their biological activities were evaluated as potential acetylcholinesterase and butyrylcholinesterase inhibitors. The compounds synthesized exerted comparable activity in comparison to rivastigmine, galantamine, and donepezil both in in vitro and in vivo studies.
- Gulcan, Hayrettin Ozan,Unlu, Serdar,Esiringu, Ilker,Ercetin, Tugba,Sahin, Yasemin,Oz, Demet,Sahin, Mustafa Fethi
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p. 5141 - 5154
(2015/02/19)
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- Design, synthesis, and biological evaluation of coumarin derivatives tethered to an edrophonium-like fragment as highly potent and selective dual binding site acetylcholinesterase inhibitors
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A large series of substituted coumarins linked through an appropriate spacer to 3-hydroxy-N,N-dimethylanilino or 3-hydroxy-N,N,N-trialkylbenzaminium moieties were synthesized and evaluated as acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitors. The highest AChE inhibitory potency in the 3-hydroxy-N,N-dimethylanilino series was observed with a 6,7-dimethoxy-3-substituted coumarin derivative, which, along with an outstanding affinity (IC50=0.236 nm) exhibits excellent AChE/BChE selectivity (SI>300 000). Most of the synthesized 3-hydroxy-N,N,N- trialkylbenzaminium salts display an AChE affinity in the sub-nanomolar to picomolar range along with excellent AChE/BChE selectivities (SI values up to 138 333). The combined use of docking and molecular dynamics simulations permitted us to shed light on the observed structure-affinity and structure-selectivity relationships, to detect two possible alternative binding modes, and to assess the critical role of π-π stacking interactions in the AChE peripheral binding site.
- Pisani, Leonardo,Catto, Marco,Giangreco, Ilenia,Leonetti, Francesco,Nicolotti, Orazio,Stefanachi, Angela,Cellamare, Saverio,Carotti, Angelo
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experimental part
p. 1616 - 1630
(2011/11/29)
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- Dihydroxylation of functionalized coumarin derivatives
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7-Acetoxy- and 7-tosyloxycoumarins were successfully dihydroxylated in RuCl3/NalO4/CeCl3 system to give the corresponding glycol derivatives in excellent yields. Tricyclic coumarin with tetrasubstituted olefin function als
- Fusegi, Keiko,Kumamoto, Takuya,Nakanishi, Waka,Ishikawa, Tsutomu
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experimental part
p. 603 - 610
(2009/09/28)
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- Al2O3/MeSO3H (AMA) as a novel heterogeneous system for synthesis of coumarins under mild conditions
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Al2O3/MeSO3H (AMA) is found to be an efficient reagent for the Pechman condensation reaction of phenols and β- ketoesters under solvent free conditions. The reaction protocol is simple, cost- effective, solvent free and gives good isolated yield with high purity and good regioselectivity.
- Sharghi, Hashem,Jokar, Mahboubeh
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p. 2721 - 2733
(2008/09/19)
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- Microwave-promoted automated synthesis of a coumarin library
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A 30-membered library of coumarins has been synthesized in a microwave-assisted Pechmann reaction using neat trifluoroacetic acid both as an acidic reagent and a reaction medium. Alternatively, polymer-supported sulfonic acid Amberlyst-15 could also be employed to facilitate the formation of coumarins. The use of a specially-built microwave synthesizer with liquid handling tools rendered the automated synthesis of a coumarin library feasible.
- Katkevi?s,Kontijevskis,Mutule,Sūna
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p. 151 - 159
(2008/12/20)
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- CHROMENONES AND THEIR USE AS MODULATORS OF METABOTROPIC GLUTAMATE RECEPTORS
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The invention relates to chromenone derivatives as well as their pharmaceutically acceptable salts. The invention further relates to a process for the preparation of such compounds. The compounds of the invention are Group I mGluR modulators and are therefore useful for the control and prevention of acute and/or chronic neurological disorders.
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Page/Page column 41-42
(2008/06/13)
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- Skeletal diversity construction via a branching synthetic strategy
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A branching synthetic strategy was used to efficiently generate structurally diverse scaffolds, which span a broad area of chemical descriptor space, and their biological activity against MRSA was demonstrated. The Royal Society of Chemistry 2006.
- Wyatt, Emma E.,Fergus, Suzanne,Galloway, Warren R. J. D.,Bender, Andreas,Fox, David J.,Plowright, Alleyn T.,Jessiman, Alan S.,Welch, Martin,Spring, David R.
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p. 3296 - 3298
(2008/09/19)
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- Vanadium(III) chloride as an effective catalyst for the Pechmann reaction
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Good yields of substituted coumarins were obtained by a synthetic method involving the Pechmann reaction using vanadium(III)chloride (VCl3) reagent to effect this condensation under solvent-free conditions. 2006 Springer Science+Business Media, Inc.
- Sunil Kumar,Kumar,Srinivasulu,Rajitha,Thirupathi Reddy,Narsimha Reddy,Udupi
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p. 172 - 175
(2007/10/03)
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- Selectfluor: A simple and efficient catalyst for the synthesis of substituted coumarins under solvent-free conditions
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Selectfluor is used as an alternative catalyst to conventional catalysts for the synthesis of substituted coumarins via Pechmann condensation of phenols with β-ketoesters under solvent-free conditions at 120 °C. This method of synthesis is simple, cost-effective, requires short reaction time, solvent-free and gives good yields.
- Kumar, B. Sunil,Reddy, Y. Thirupathi,Reddy, P. Narsimha,Kumar,Rajitha
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p. 477 - 479
(2007/10/03)
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- Compound
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A compound is described. In particular, a non-steroidal sulphamate compound is described. The compound is suitable for use as an inhibitor of oestrone sulphatase. The compound is of general Formula (A), wherein R1-R6 are independentl
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- Compound
-
A compound is described. In particular, a non-steroidal sulphamate compound is described. The compound is suitable for use as an inhibitor of oestrone sulphatase. The compound is of general Formula (A), wherein R1-R6 are independentl
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- ZrCl4-catalyzed Pechmann reaction: Synthesis of coumarins under solvent-free conditions
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Zirconium (IV) chloride is used as an efficient catalyst in the Pechmann condensation reaction of phenols with β-keto esters leading to the formation of coumarin derivatives in good yields under solvent-free conditions.
- Smitha,Reddy, Ch. Sanjeeva
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p. 3997 - 4003
(2007/10/03)
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- Sulphamic acid - An efficient and cost-effective solid acid catalyst for the pechmann reaction
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Sulphamic acid (H2NSO3H, SA) is used as an alternative to conventional acid catalysts in the Pechmann condensation of phenols with β-ketoester leading to the formation of substituted coumarin. The method is simple, cost-effective, solvent-free and gives good yields in a short reaction time.
- Singh, Pankajkumar R.,Singh, Devendrapratap U.,Samant, Shriniwas D.
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p. 1909 - 1912
(2007/10/03)
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- Modified coumarins. 7. Synthesis and biological activity of mannich bases of substituted 7,8,9,10-tetrahydrobenzo[c]chromen-6-ones
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Condensation of 1- and 3-hydroxy-7,8,9,10-tetrahydrobenzo[c]chromen-6-ones with substituted 1,1-diaminomethanes produced Mannich bases containing a dialkylaminomethyl group in the 2- and 4-positions of 7, 8,9,10-tetrahydrobenzo[c]chromen-6-one. Pharmacological screening of 2-chloro-3-hydroxy-4-(1-pyrrolidinylmethyl)-7,8,9,10-tetrahydro-6H-benzo[c] chromen-6-one in Wistar rats showed that it possesses low toxicity and acts as a stimulant of the central and peripheral nervous systems with indications of neuroleptic and tranquilizing activities.
- Garazd,Panteleimonova,Garazd,Khilya
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p. 532 - 538
(2007/10/03)
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- Anti-AIDS agents. 42. Synthesis and anti-HIV activity of disubstituted (3′R,4′R)-3′,4′-di-O-(S)-camphanoyl-(+)-cis- khellactone analogues
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A series of disubstituted 3′,4′-di-O-(S)-camphanoyl-(+)-cis-khellactone (DCK) analogues (1-10) were synthesized and evaluated for inhibition of HIV-1 replication in H9 lymphocytes. 5-Methoxy-4-methyl DCK (8) was the most promising compound with an EC50 value of 7.21 × 10-6 μM and a therapeutic index of >2.08 × 10,7 which were much better than those of lead compound DCK in the same assay. Another six disubstituted DCK analogues (1-5 and 7) were more potent than AZT but less active than DCK. Conformational analysis suggested that resonance of the coumarin system is an essential structural feature for potent anti-HIV activity. Steric compression of C(4) and C(5) substituents of the coumarin moiety can reduce the overall planarity and thus resonance of the coumarin nucleus, resulting in a decrease or lack of anti-HIV activity.
- Xie,Takeuchi,Cosentino,McPhail,Lee
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p. 664 - 671
(2007/10/03)
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- Stereochemistry of the dihydro compound from lithium/ammonia reduction of 3-methoxy-7,8,9,10-tetrahydro-6H-dibenzo[b, d]pyran-6-one
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X-Ray crystallography has established that the lithium/ammonia reduction of 3-methoxy-7,8,9,10-tetrahydro-6H-dibenzo[b, d]pyran-6-one gives the cis-dihydro compound (6aRS, 10aSr)-3-methoxy-6a,7,8,9,10,10a-hexahydro-6H-dibenzo[b, d]pyran-6-one (7).
- Collins, David J.,Fallon, Gary D.,Staffa, Alfred,Tope, Helen
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p. 719 - 721
(2007/10/03)
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- Environmentally friendly synthesis of coumarin derivatives employing heterogeneous catalysis
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Zeolite H-BEA and other solid acids have been shown to be effective catalysts for the production of coumarin derivatives from activated phenols and acids or esters possessing an additional alkylation function, or β-keto esters (Pechmann reaction). These heterogeneous catalysts eliminate the production of acidic waste streams associated with conventional (Lewis) acid catalysts. Zeolite H-BEA proved to be the preferred catalyst.
- Gunnewegh,Hoefnagel,Downing,Van Bekkum
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p. 226 - 230
(2007/10/03)
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