- Design, synthesis and preliminary bioactivity evaluation of bitopic benzopyranomorpholine analogues as selective dopamine D3 receptor ligands as anti-drug addiction therapeutic agents
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Three series of bitopic benzopyranomorpholine analogues were designed, synthesized, and evaluated as a novel class of selective ligands for the dopamine D3 receptor. Binding affinities of target compounds were determined using the method of radioligand binding assay. Most compounds demonstrated considerable binding affinities and selectivity for D3 receptor. Besides, the compounds were screened for their ability to alleviate withdrawal symptoms of opioid addiction in animal behavioral models. The results showed that compound 20h displayed nanomolar affinity for the D3R, and exhibited anti-drug addiction efficacy in the animal model of of naloxone-induced withdrawal symptoms in morphine-dependent mice.
- Cai, Jin,Chen, Xixi,Huang, Mingqi,Ji, Min,Wang, Yuhong
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- Acid activated montmorillonite K-10 mediated intramolecular acylation: Simple and convenient synthesis of 4-chromanones
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3-Aryloxyproionic acids undergo intramolecular cyclization in the presence of AA.Mont.K-10 in toluene under reflux for 30–45 min in good to excellent yields. Phenyl ring bearing various substituents at the ortho, meta, para positions undergo this cyclization reaction. This method involves simple work up and amenable for large scale preparations. The heterogeneous acid treated catalyst can be regenerated and used for up to three cycles with minimum loss of activity.
- Begum, Ayisha F.,Balasubramanian, Kalpattu K.,Shanmugasundaram, Bhagavathy
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- Facile access to chiral 4-substituted chromanes through Rh-catalyzed asymmetric hydrogenation
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Rh/ZhaoPhos-catalyzed asymmetric hydrogenation of a series of (E)-2-(chroman-4-ylidene)acetates was successfully developed to prepare various chiral 4-substituted chromanes with high yields and excellent enantioselectivities (up to 99percent yield, 98percent ee). Moreover, the gram-scale hydrogenation could be performed well in the presence of 0.02 molpercent catalyst loading (TON = 5000), the hydrogenation product was easily converted to access other important compounds, which demonstrated the synthetic utility of this asymmetric catalytic methodology.
- Tao, Lin,Zhao, Qingyang,Zhang, Xumu,Dong, Xiu-Qin
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p. 1859 - 1862
(2020/01/21)
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- CHROMENE DERIVATIVES AS INHIBITORS OF TCR-NCK INTERACTION
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The present invention provides compounds that modulate the interaction of TCR with Nck, compositions thereof, and methods of treatment using the same.
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Paragraph 0468; 0470
(2019/09/06)
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- Synthesis of Flavanones via Palladium(II)-Catalyzed One-Pot β-Arylation of Chromanones with Arylboronic Acids
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A total of 47 flavanones were expediently synthesized via one-pot β-arylation of chromanones, a class of simple ketones possessing chemically unactivated β sites, with arylboronic acids via tandem palladium(II) catalysis. This reaction provides a novel route to various flavanones, including natural products such as naringenin trimethyl ether, in yields up to 92percent.
- Cho, Yang Yil,Jang, Hyu Jeong,Kim, Dong Hwan,Kim, Nam Yong,Kim, Nam-Jung,Kim, Young Min,Lee, Soo Jin,Lee, Yong Sup,Park, Boyoung Y.,Son, Seung Hwan,Yoo, Hyung-Seok
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supporting information
p. 10012 - 10023
(2019/08/30)
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- Hydrated ferric sulfate-catalyzed reactions of indole with aldehydes, ketones, cyclic ketones, and chromanones: Synthesis of bisindoles and trisindoles
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Hydrated ferric sulfate [Fe2(SO4)3·xH2O] has been found to be an efficient catalyst for condensation of bisindoles or trisindoles with aliphatic or aryl aldehydes and ketones including methyl and ethyl-alkyl ketones, methyl aryl ketones, cyclic ketones, and 4-chromanones in 19–96% yields. Trisindoles and 2,2'-alkylidenebisindoles were obtained from indole-3-carbaldehydes or 3-methylindole in 72–84% yields. A total of 43 substrates was employed, giving 33 bisindoles, 3 trisindoles, and one 2:2 product; seventeen of these are new. The best results were obtained from heating ethanolic suspensions, with Fe2(SO4)3·xH2O loaded at 60 mg per mmol of electrophiles. The reaction times were typically 1–4 h, while hindered electrophiles required 8–24 h. These conditions were strong enough to promote 2:1 condensation of indole with substrates without forming higher-order byproducts, with few exceptions. This strategy features tolerance by the catalyst of a wide range of functional groups, readily available starting materials, simple operation, mild reaction conditions, and is environmentally friendly.
- Noland, Wayland E.,Kumar, Honnaiah Vijay,Flick, Grant C.,Aspros, Cole L.,Yoon, Jong Hyeon,Wilt, Andre C.,Dehkordi, Nasim,Thao, Sheng,Schneerer, Andrew K.,Gao, Siming,Tritch, Kenneth J.
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p. 3913 - 3922
(2017/06/13)
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- Synthesis, characterization, and antimicrobial activity of novel substituted 2H-chromenyl acrylates
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The present study deals with conventional Witting olefination of 2H-chromene-3-carbaldehydes with stabilized ylide in the presence of dichloromethane to afford (2E)-ethyl-3-(4-chloro-2H-chromen-3-yl) acrylate derivatives. All the products were found to have E-geometry at C=C bond. The synthesized compounds were characterized by spectral data such as IR, 1H NMR and MS. Compounds were screened for antimicrobial activity against strains of gram positive, gram negative bacterial and fungal strains. All compounds showed good antibacterial and antifungal activity.
- Subhashini,Ravi,Cherupally,China Raju,Reddy,Bee
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p. 2900 - 2905
(2017/03/22)
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- The enantiospecific synthesis of chromanes and isochromanes using a variant of an intramolecular Nicholas reaction
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The enantiospecific synthesis of chromanes and isochromanes obtained from an intramolecular Nicholas cyclisation reaction is discussed. During the course of this study we observed the formation of chroman-4-ones from a CAN deprotection step of a dioxolane and this is also discussed.
- Tyrrell, Elizabeth,Mazloumi, Khatebeh,Banti, Donatella,Sajdak, Paulina,Sinclair, Alex,Le Gresley, Adam
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experimental part
p. 4280 - 4282
(2012/09/22)
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- Chroman Compound, Processes for Its Preparation, and Its Pharmaceutical Use
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The present invention provided a chroman compound, the method of its preparation and pharmaceutical applications. The compound are represented by formula (I) and its pharmaceutical salt, where in :x is for O or S; n is for 2, 3 or 4; R1 is 6-situ or 7-situ halogen, C1-4alkyl, C1-4alkyoxyl, benzyloxy, acylamino; R2 is nitrogen-containing pentatomic or hexahydric substituted heterocyclic ring. The compound is useful to prepare anti-arrhythmic drugs, the reaction conditions of the method are mild, the raw material are plenty and easy to be obtained, and the operation and post-treatment are simple.
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Page/Page column 5; 17
(2008/06/13)
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- Synthesis, stereochemical assignments, and biological activities of homoisoflavonoids
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A series of four naturally occurring homoisoflavonoids and eight analogs have been synthesized starting from an appropriately substituted phenol through chroman-4-one, in four steps. The products were assigned as E-isomers based on NMR spectroscopic data.
- Siddaiah, Vidavalur,Rao, Chunduri Venkata,Venkateswarlu, Somepalli,Krishnaraju, Alluri V.,Subbaraju, Gottumukkala V.
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p. 2545 - 2551
(2007/10/03)
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- N-heterocyclic carbene catalyzed nucleophilic substitution reaction for construction of benzopyrones and benzofuranones
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N-Heterocyclic carbene as an efficient organic catalyst was employed to catalyze an intramolecular nucleophilic substitution reaction. When R 2 was a phenyl group, the cyclization process underwent isomerization, leading to generation of benzofuranone.
- He, Jinmei,Zheng, Jiyue,Liu, Jian,She, Xuegong,Pan, Xinfu
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p. 4637 - 4640
(2007/10/03)
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- Substituted heterocyclic compounds, method for preparing and compositions containing same
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The invention relates to compounds of formula (I): wherein: R1, R2and R3are as defined in the description, X is as defined in the description, Y represents an oxygen atom, a sulphur atom, a C(H)qgroup, SO or SO2, n is equal to from 0 to 5, A represents a NR5R6group, and medicinal products containing the same which are useful in treating or in preventing melatoninergic disorders.
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- Substituted tetralins, chromans and related compounds in the treatment of asthma
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PCT No. PCT/US87/02734 Sec. 371 Date Apr. 11, 1990 Sec. 102(e) Date Apr. 11, 1990 PCT Filed Oct. 19, 1987Substituted tetralins, chromans and related compounds which, by inhibiting 5-lipoxygenase enzyme and/or blocking leukotriene receptors, are useful in the prevention or treatment of asthma, arthritis, psoriasis, ulcers, myocardial infarction and related disease states in mammals; pharmaceutical compositions comprising said compounds; a method of treatment with said compounds; and intermediates useful in the synthesis of said compounds.
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- Synthesis of Novel HMG-CoA Reductase Inhibitors, II. Heterocyclic Analogs of Mevinolin
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The indole (1) and chroman analogs (2) of mevinolin and their 6S diastereomers 15c and 25d were synthesized in several steps starting with methyl (R)-3--4-formylbutyrate (12) and 2-(indol-3-yl)ethanol (3) or 6-methoxychroman-4-one (16), respectively.Compounds 1 and 2 inhibited moderately the HMG-CoA reductase.The diastereomers 15c and 25d were shown to be inactive. - Keywords: HMG-CoA reductase inhibitors / 3-Indolylheptanoates and -acetates / 4-Chromanylheptanoates and -acetates
- Novak, Lajos,Hornyanszky, Gabor,Rohaly, Janos,Kolonits, Pal,Szantay, Csaba
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p. 1877 - 1884
(2007/10/03)
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- SUBSTITUTED CHROMANS AND THEIR USE IN THE TREATMENT OF ASTHMA, ARTHRITIS AND RELATED DISEASES
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Substituted chromans which by inhibiting 5-lipoxygenase enzyme are useful in the prevention or treatment of asthma, arthritis, psoriasis, ulcers, myocardial infarction, stroke and related disease states in mammals, pharmaceutical compositions thereof, a m
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- Substituted tetralins, chromans and related compounds in the treatment of asthma, arthritis and related diseases
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Substituted tetralins, chromans and related compounds which, by inhibiting 5-lipoxygenase enzyme and/or blocking leukotriene receptors, are useful in the prevention or treatment of asthma, arthritis, psoriasis, ulcers, myocardial infarction and related disease states in mammals, pharmaceutical compositions thereof, a method of treatment therewith, and to intermediates useful in the synthesis thereof.
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- Synthesis and Dopamine Agonist Properties of (+/-)-trans-3,4,4a,10b-Tetrahydro-4-propyl-2H,5H-benzopyrano-1,4-oxazin-9-ol and Its Enantiomers
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The dopamine agonist profile of (+/-)-trans-3,4,4a,10b-tetrahydro-4-propyl-2H,5H-benzopyrano-1,4-oxazin-9-ol (16a) and its enantiomers (16b-c) was examined.Racemic 16a exhibited moderate affinity for the dopamine (DA) D2 receptor labe
- DeWald, Horace A.,Heffner, Thomas G.,Jaen, Juan C.,Lustgarten, David M.,McPhail, Andrew T.,et al.
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p. 445 - 450
(2007/10/02)
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- THERMAL BEHAVIOUR OF ARYL γ-HALOPROPARGYL ETHERS
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A systematic study of the behaviour of aryl γ-halopropargyl ethers under thermal condition was undertaken.Aryl γ-bromopropargyl ethers 2 underwent unique transformation in N,N-diethylaniline (215 deg C, 6 h) giving rise to a mixture of products 3,4 and 5,whereas, under similar conditions aryl γ-chloropropargyl ethers 8, afforded 4-chlorochromenes, 9.A remarkable substituent and solvent effect has been observed in the thermolysis of these aryl γ-bromo and γ-chloropropargyl ethers, rendering this transformation as a method for the synthesis of a number of substituted 4-bromochromenes 3, 4-chlorochromenes 9 and chroman-4-ones 7.In contrast, solution thermolysis of aryl γ-iodopropargyl ether 11 afforded aryl propargyl ether 1 as the major product.
- Ariamala, G.,Balasubramanian, K. K.
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p. 309 - 318
(2007/10/02)
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- A SIMPLE ROUTE FOR THE SYNTHESIS OF 4-CHLOROCHROMENES AND CHROMAN-4-ONES
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A one pot synthesis of a number of 4-chlorochromenes and chroman-4-ones was achived from γ-chloropropargyl aryl ethers proceeding through Claisen rearrangement, depending upon the solvent of choice.
- Ariamala, G.,Balasubramanian, K.K.
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p. 3487 - 3488
(2007/10/02)
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- A Novel and Convenient Mercury(II) Mediated Synthesis of Chroman-4-ones
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A simple route to chroman-4-ones from γ-bromopropynyl aryl ethers (1) using mercury(II) trifluoroacetate as a catalyst is described.
- Gopalsamy, Ariamala,Balasubramanian, K. K.
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- UNEXPECTED FORMATION OF CHROMAN-4-ONES DURING THE SYNTHESIS OF 4-HYDROXYMETHYL-2H-CHROMENES FROM 4-ARYLOXYBUT-2-YN-1-OLS
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The unexpected formation of chroman-4-ones by refluxing 4-aryloxybut-2-yn-1-ols in diethylaniline has been studied, 4-hydroxymethyl-2H-chromene and chroman-4-carboxaldehyde derivatives being estbalished as intermediates.
- Camps, P.,Lluch, M.A.,Climent, M.J.,Miranda, M.A.
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p. 2041 - 2042
(2007/10/02)
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- Serotonin Receptor Affinity of Cathinone and Related Analogues
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A series of cathinone (α-aminopropiophenone) analogues was examined using the isolated rat fundus preparation. (S)-(-)-Cathinone possesses twice the serotonin receptor affinity of (+/-)-cathinone and four times the affinity of racemic amphetamine.Several derivatives of cathinone were found to either possess a lower affinity than the parent compound or did not interact with the receptors in a competitive manner.Several novel analogues, 1-(aminomethyl)-3,4-dihydronaphthalene hydrochloride (3), 4-(aminomethyl)-3-chromene hydrochloride (4b), as well as its 6-methoxy derivative, 4a, interact with serotonin receptors but in a fashion which is, most likely, dissimilar to the interaction of the substituted cathinone analogues.
- Glennon, Richard A.,Liebowitz, Stephen M.
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p. 393 - 397
(2007/10/02)
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