- N-(2,7-dimethyl-2-alkyl-2H-chromen-6-yl)sulfonamide derivatives as selective serotonin 5-HT6 receptor antagonists: Design, synthesis, and biological evaluation
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Serotonin 5-HT6 receptor, which is predominantly expressed in the central nervous system, is a valuable therapeutic target. Serotonin 5-HT6 receptor antagonists have potential for the treatment of various diseases that include psychotic disorders, dementia, depression, and obesity. In this study, we designed and synthesized the N-(2,7-dimethyl-2-alkyl-2H-chromen-6-yl)sulfonamide-based library as a potential serotonin 5-HT6 receptor antagonist. The library was subjected to a series of binding affinity tests to identify the lead compound, and check the selectivity of test compounds towards the 5-HT6 receptor. Accordingly, compound 6m was identified as the most active compound, with IC50 = 87 nM. The binding affinity of 95.3% of 6m (10 μM) with the 5-HT6 receptor among other serotonin 5-HT1a, 5-HT2a, 5-HT2c, and 5-HT7, and dopamine receptors D1, D2, D3, and D4, demonstrated the high selectivity of 6m towards the 5-HT6 receptor.
- Abdildinova, Aizhan,Kim, Young Chang,Lee, Gee-Hyung,Park, Woo-Kyu,Cho, Heeyeong,Gong, Young-Dae
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- A benzopyran with antiarrhythmic activity is an inhibitor of Kir3.1-containing potassium channels
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Atrial fibrillation (AF) is the most commonly diagnosed cardiac arrhythmia and is associated with increased morbidity and mortality. Currently approved AF antiarrhythmic drugs have limited efficacy and/or carry the risk of ventricular proarrhythmia. The c
- Cui, Meng,Alhamshari, Yaser,Cantwell, Lucas,EI-Haou, Said,Eptaminitaki, Giasemi C.,Chang, Mengmeng,Abou-Assali, Obada,Tan, Haozhou,Xu, Keman,Masotti, Meghan,Plant, Leigh D.,Thakur, Ganesh A.,Noujaim, Sami F.,Milnes, James,Logothetis, Diomedes E.
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- Total Synthesis of Fontanesine B and Its Isomer: Their Antiproliferative Activity against Human Colorectal Cancer Cells
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A concise synthesis of pyrano[3,2-e]indole alkaloid fontanesine B by a Fischer indolization is described. This key Fischer indolization starts with the pyran-ring and alkene intact, facilitating potential synthetic applications. Furthermore, fontanesine B and its isomer were evaluated for in vitro antiproliferative activity against human colorectal cancer cells. The isomer of fontanesine B showed higher antiproliferative activity than the natural product, fontanesine B (2).
- Abe, Takumi,Itoh, Tomoki,Terasaki, Masaru
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- Synthesis and biological evaluation of 2,2-dimethylbenzopyran derivatives as potent neuroprotection agents
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The development of novel neuroprotection agents is of great significance for the treatment of ischemic stroke. In this study, a series of compounds comprising 2,2-dimethylbenzopyran groups and cinnamic acid groups have been synthesized. Preferential combination principles and bioisostere that improved the neuroprotective effect of the compounds were identified for this series via biological activity assay in vitro. Meanwhile, a functional reversal group of the acrylamide amide resulted in the most active compounds. Among them, BN-07 significantly improved the morphology of neurons and obviously increased cell survival rate of primary neurons induced by oxygen glucose deprivation (OGD), superior to clinically used anti-ischemic stroke drug edaravone (Eda). Overall, our findings may provide an alternative strategy for the design of novel anti-ischemic stroke agents with more potency than Eda.
- Du, Fangyu,Zhou, Qifan,Fu, Xiaoxiao,Shi, Yajie,Chen, Yuanguang,Fang, Wuhong,Yang, Jingyu,Chen, Guoliang
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p. 2498 - 2508
(2019/02/01)
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- 2,2-dimethylbenzopyran derivative and preparation method and use thereof
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The invention belongs to the technical field of medicines, and discloses a 2,2-dimethylbenzopyran derivative and a preparation method and use of the 2,2-dimethylbenzopyran derivative. The derivative and pharmaceutically acceptable salt of the derivative have the structural formulae shown in the description, wherein Ar, Ar, X, Y and R1 are as described in the claims and the description. The preparation methods of the derivative and the pharmaceutically acceptable salt of the derivative comprise the following steps: the formula (I) is obtained by mainly taking acetaminophen as a raw material, and subjected to the reactions of Williamson ether formation, cyclization, hydrolysis, amide formation and the like; the formula II is obtained by mainly taking p-hydroxybenzaldehyde as a raw material, and subjected to the reactions of the Williamson ether formation, cyclization, Knoevenagel condensation, amide formation and the like. The derivative and the pharmaceutically acceptable salt ofthe derivative disclosed by the invention can be used for preparing neuroprotective agents and have better neuroprotective effects on ischemic stroke.
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- METHOD FOR PRODUCING HETEROCYCLIC COMPOUND
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There is provided a method for producing with a high efficiency a heterocyclic compound that is useful as a raw material for pharamaceuticals. A novel production method for producing 2,2,7,9-tetramethyl-2H-pyrano[2,3-g]quinoline (compound (6)) that has a quinoline ring and a chromene ring using N-(3-acetyl-4-hydroxyphenyl)butylamide (compound (1′)) that is commercially available as a raw material for pharamaceuticals or the like as a starting raw material; and a method for purifying compound (6), characterized by purifying by subjecting it to conversion into a salt form.
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Paragraph 0150; 0151; 0152
(2016/07/05)
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- Identification of 3-hydroxy-4[3,4-dihydro-3-oxo-2H-1,4-benzoxazin-4-yl]-2,2-dimethyldihydro-2H-benzopyran derivatives as potassium channel activators and anti-inflammatory agents
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The present study described the design, synthesis and identification of 3-hydroxy-4[3,4-dihydro-3-oxo-2H-1,4-benzoxazin-4-yl]-2,2-dimethyldihydro-2H-benzopyran derivatives. Their biological activity was tested for KATP channel opener as antihypertensives, COX-1 and COX-2 activity. The results were compared with the activity of cromakalim, ibuprofen and celecoxib. The study aimed at exploring the influence of introduction of a benzoxazine substituent at position 6 of various derivatives of benzopyrans in order to improve biological activity. Several compounds were found to be equipotent or even more potent than cromakalim. Out of these nitro-substituted benzopyrans, nitro substitution at benzoxazino group possessed potent antihypertensive activity in the R/S isomers. With amino derivatives, activity remains constant when compared with standard cromakalim. Similarly, compounds 17b, 17c, 17e and 17h have exhibited around 40 % inhibition of COX-1 as compared to the inhibition of COX-2. Only two compounds 17g and 17i exhibited effective inhibition more than 50 % of COX-2 compared with the inhibition of COX-1 at a concentration of 0.3 mg/ml.
- Bano, Mohsina,Barot, Kuldipsinh P.,Jain, Shailesh V.,Ghate, Manjunath D.
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p. 3008 - 3020
(2015/03/18)
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- METHOD FOR PRODUCING NITROGEN-CONTAINING HETEROCYCLIC N-OXIDE COMPOUND
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The problem of the present invention is to provide a production method for safely synthesizing a nitrogen-containing heterocyclic N-oxide compound in high yield. Another problem of the present invention is to provide a novel N-oxide compound. There is provided a method for producing a nitrogen-containing heterocyclic N-oxide compound of Formula (2), such as 2,2,7,9-tetramethyl-2H-pyrano[2,3-g]quinoline N-oxide, by oxidizing a nitrogen-containing heterocyclic compound of Formula (1), such as 2,2,7,9-tetramethyl-2H-pyrano[2,3-g]quinoline with a persulfate.
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Paragraph 0088
(2015/10/28)
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- 6-alkylamino-2,2'-disubstituted-7,8-disubstituted-2H-1-benzopyran derivatives as 5-lipoxygenase inhibitor
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When a multi-step process reaction is carried out in a solution, it generally requires several treatments and purification procedures to go through with after the reaction, however, the inventive method for preparing 2,2′-disubstituted-3,4-dihydro-7,8-dis
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Page/Page column 4-5
(2010/02/13)
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- PROCESS FOR PRODUCING AMINOBENZOPYRAN COMPOUND
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There is provided a method for producing aminobenzopyran compound, which results in little wastes, has no influence on reactors and necessitates a simple work-up procedure. Concretely, it is a method for producing aminobenzopyran compound of formula (2)characterized by reducing a nitro group on 2,2-dimethyl 2H-1-benzopyran compound of formula (1) with hydrazine in the presence of a metal catalyst.
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Page/Page column 5-7
(2008/06/13)
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- Benzodiazolo analogs
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Novel potassium channel activators of the formula STR1 where Y, X, X 1, X 2 (N or O), and R 1 -R 4 are as defined herein, are disclosed.
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