- CARBAZOLE ALKALOIDS FROM CLAUSENA LANSIUM
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Three new carbazole alkaloids, 3-formyl-6-methoxycarbazole, methyl 6-methoxycarbazole-3-carboxylate and 3-formyl-1,6-dimethoxycarbazole and two carbazole derivatives, 3-formyl carbazole and methyl carbazole-3-carboxylate, reported for the first time from Nature, have been isolated from the root of Clausena lansium along with three previously reported carbazole alkaloids, murrayanine, glycozoline and indizoline.All isolated compounds except glycozoline have a carbonyl group at C-3 with different substitution patterns at C-1, C-2 and C-6.
- Li, Wen-Shyong,McChesney, James D.,El-Feraly, Farouk S.
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- One-electron photooxidation of carbazole in the presence of carbon tetrachloride. Part I. Carbon tetrachloride and ethanol used as reaction media
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The photochemical reaction products of carbazole with carbon tetrachloride in ethanol have been isolated and identified along with photoproducts in the irradiated solution of carbazole in pure CCl4 using water and ethanol added after the irradiation.This allowed us to discuss the complex mechanism of secondary photochemical changes in the carbazole-CCl4 system.We propose that the electron transfer from carbazole to CCl4 molecule in the excited CT complex, , is the primary photochemical reaction followed by a heterolytic dissociation of C-Cl bond which gives rise to the primary photoproducts in the solvent cage .Secondary photochemical reactions initiate transformation of the radical cation of carbazole in the solvent cage giving rise to the following intermediate species: .The probability of formation and further transformations of these transient products: α, β, and γi, depends strongly on the nature of the reaction media.Thermodinamically stable products are formed depending on the reaction media; (carboethoxy)carbazoles, (carbo-N-carbazyl)carbazoles, and carbazole - carboxylic acids can serve as a proof for the formation of the above listed intermediates.All the results reported on the secondary photochemical reactions strongly support the electron-transfer primary mechanism used to explain the fluorescence quenching of carbazole by CCl4.The results also explain the changes observed in the fluorescence spectrum of carbazole when the ethanol solution of carbazole in the presence of CCl4 is irradiated.
- Zelent, Bogumil,Durocher, Gilles
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- Copper(II) catalyzed aromatization of tetrahydrocarbazole: An unprecedented protocol and its utility towards the synthesis of carbazole alkaloids
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An efficient protocol for the aromatization of tetrahydrocarbazole is described by using catalytic copper(II) chloride dihydrate in DMSO. This newly established methodology has utilized towards the synthesis of naturally occurring carbazole alkaloids, namely 3-methylcarbazole, 3-formyl carbazole, glycozoline, glycozolicine and clauszoline-K. In addition, the protocol is generalized for the aromatization of N-substituted tetrahydrocarbazole, 1,2,3,4-tetrahydroquinoline, 1,2,3,4-tetrahydroisoquinoline and 1,2,3,4-tetrahydro β-carboline to give the corresponding heteroaromatic compounds from very good to excellent yield. Moreover, this method has been proven to be tolerant to a broad range of functional groups with excellent yields.
- Dalvi, Bhakti A.,Lokhande, Pradeep D.
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supporting information
p. 2145 - 2149
(2018/05/08)
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- Discovery of carbazole carboxamides as novel RORγt inverse agonists
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A novel series of carbazole carboxamides was discovered as potent RORγt inverse agonists using a scaffold hybridization strategy. Structure-activity relationship exploration on the amide linker, carbazole ring and arylsulfone moiety of the hybrid amide 3a led to identification of potent RORγt inverse agonists. Compound 6c was found to have a good RORγt activity with an IC50 of 58.5 nM in FRET assay, and reasonable inhibitory activity in mouse Th17 cell differentiation assay (58.8% inhibition at 0.3 μM). The binding mode of carbazole carboxamides in RORγt ligand binding domain was discussed.
- Huang, Yafei,Yu, Mingcheng,Sun, Nannan,Tang, Ting,Yu, Fazhi,Song, Xiaoxia,Xie, Qiong,Fu, Wei,Shao, Liming,Wang, Yonghui
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p. 465 - 476
(2018/02/28)
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- FUNCTIONALISED AND SUBSTITUTED CARBAZOLES AS ANTI-CANCER AGENTS
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The present invention relates to anti-tropomyosin compounds, processes for their preparation, and methods for treating or preventing a disease or disorder, such as a proliferative disease (preferably cancer), using compounds of the invention.
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(2016/02/26)
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- Iodine-catalyzed aromatization of tetrahydrocarbazoles and its utility in the synthesis of glycozoline and murrayafoline A: A combined experimental and computational investigation
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A new protocol for the aromatization of tetrahydrocarbazoles has been achieved using a catalytic amount of iodine, giving high yields. The role of iodine in the aromatization has been explained by DFT, and its wide scope is extended to the total synthesis of glycozoline and murrayafoline A. This method has proven to be tolerant of a broad range of functional groups. This journal is the Partner Organisations 2014.
- Humne, Vivek,Dangat, Yuvraj,Vanka, Kumar,Lokhande, Pradeep
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supporting information
p. 4832 - 4836
(2014/07/07)
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- Mastering tricyclic ring systems for desirable functional cannabinoid activity
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There is growing interest in using cannabinoid receptor 2 (CB2) agonists for the treatment of neuropathic pain and other indications. In continuation of our ongoing program aiming for the development of new small molecule cannabinoid ligands, we have synthesized a novel series of carbazole and γ-carboline derivatives. The affinities of the newly synthesized compounds were determined by a competitive radioligand displacement assay for human CB2 cannabinoid receptor and rat CB1 cannabinoid receptor. Functional activity and selectivity at human CB1 and CB2 receptors were characterized using receptor internalization and [35S]GTP-γ-S assays. The structure-activity relationship and optimization studies of the carbazole series have led to the discovery of a non-selective CB1 and CB2 agonist, compound 4. Our subsequent research efforts to increase CB2 selectivity of this lead compound have led to the discovery of CB2 selective compound 64, which robustly internalized CB2 receptors. Compound 64 had potent inhibitory effects on pain hypersensitivity in a rat model of neuropathic pain. Other potent and CB2 receptor-selective compounds, including compounds 63 and 68, and a selective CB1 agonist, compound 74 were also discovered. In addition, we identified the CB2 ligand 35 which failed to promote CB2 receptor internalization and inhibited compound CP55,940-induced CB2 internalization despite a high CB2 receptor affinity. The present study provides novel tricyclic series as a starting point for further investigations of CB2 pharmacology and pain treatment.
- Petrov, Ravil R.,Knight, Lindsay,Chen, Shao-Rui,Wager-Miller, Jim,McDaniel, Steven W.,Diaz, Fanny,Barth, Francis,Pan, Hui-Lin,Mackie, Ken,Cavasotto, Claudio N.,Diaz, Philippe
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p. 881 - 907
(2013/11/19)
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- Novel Tricyclic Modulators of Cannabinoid Receptors
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The compounds of the invention are modulators of cannabinoid receptors CB1 or CB2. The compounds can be used for the prevention or treatment of, e.g., pain, cancer, skin diseases, weight-associated disorders, chemical addictions, psychiatric disorders, neurodegenerative disorders, bone diseases, and inflammatory diseases. The compounds of the invention can further be used to study these diseases and disorders, as well as cannabinoid receptor biology, by coupling the compounds to, e.g., imaging agents.
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- NOVEL PIPERAZINE DERIVATIVES AS INHIBITORS OF STEAROYL-COA DESATURASE
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The present invention relates to piperazine derivatives that act as inhibitors of stearoyl-CoA desaturase. The invention also relates to methods of preparing the compounds, compositions containing the compounds, and to methods of treatment using the compounds.
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(2010/07/04)
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- NOVEL PIPERAZINE DERIVATIVES AS INHIBITORS OF STEAROYL-CoA DESATURASE
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The present invention relates to piperidine derivatives that act as inhibitors of stearoyl-CoA desaturase. The invention also relates to methods of preparing the compounds, compositions containing the compounds, and to methods of treatment using the compounds.
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(2009/10/01)
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- TRICYCLIC COMPOUNDS
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A compound represented by the formula (I) [A represents a 5- to 7-membered hydrocarbon ring group; L represents -NR3-CO-, -CO-NR3- and the like (R3 represents a hydrogen atom, a lower alkyl group, a lower acyl group and the like); M represents an alkylene linking group (a carbon atom constituting the carbon chain may be replaced with a nitrogen atom, an oxygen atom and the like); X represents -S-, -O-, -NR4-, -NR5-CO- and the like (R4 and R5 represent a hydrogen atom, a lower alkyl group and the like) or a single bond; Y represents an alkyl group, an aryl group, an amino group, an aromatic heterocyclic group and the like; R1 represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group or a lower acyl group; and R21, R22 and R23 represent a hydrogen atom, a hydroxyl group, a lower alkyl group and the like] or a salt thereof. The compound is useful as an active ingredient of medicaments for diseases in which neuropeptide Y is involved, ingestion control for hyperphagia and the like.
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- Fused indolecarboxamides: dopamine receptor subtype specific ligands
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Disclosed are compounds of the formula: or the pharmaceutically acceptable acid addition salts thereof wherein: R1and R2are the same or different and represent hydrogen, C1-C6alkyl, halogen, hydroxy, amino, cyano, nitro, trifluoromethyl, trifluoromethoxy, C1-C6alkoxy, —O2CR′, —NHCOR′, —COR′, —SOmR′, where R′ is C1-C6alkyl and wherein m is 0, 1 or2; or R1and R2independently represent —CONR′R″, or —NR′R″ where R′ and R″ independently represent hydrogen or C1-C6alkyl; R3is hydrogen, C1-C6alkyl, or —COR′″ where R′″ is C1-C6alkyl; R4is hydrogen or C1-C6alkyl; and R represents an azacycloalkylalkyl group, which compounds are useful in the treatment of affective disorders such as schizophrenia, depression, Alzheimer's disease, movement disorders such as Parkinsonism and dysronia, and other disorders which respond to dopaminergic blockade such as substance abuse and obsessive compulsive disorders. Further, compounds of this invention are useful in treating the extrapyramidal side effects associated with the use of conventional neuroleptic agents.
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- Fused indolecarboxamides: dopamine receptor subtype specific ligands
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Disclosed are compounds of the formula: STR1 or the pharmaceutically acceptable acid addition salts thereof wherein: STR2 represents an aromatic or alicyclic ring; R 1 and R 2 are the same or different and represent hydrogen, C 1 -C 6 alkyl, halogen, hydroxy, amino, cyano, nitro, trifluoromethyl, trifluoromethoxy, C 1 -C 6 alkoxy, --O 2 CR'', --NHCOR'', --COR'', --SO m R'', where R'' is C 1 -C 6 alkyl and wherein m is 0, 1 or 2; orR 1 and R 2 independently represent --CONR''R"", or --NR''R"" where R'' and R"" independently represent hydrogen or C 1 -C 6 alkyl;R 3 is hydrogen, C 1 -C 6 alkyl, or --COR''"" where R''"" is C 1 -C 6 alkyl;R 4 is hydrogen or C 1 -C 6 alkyl; andR represents an aminoalkyl group,which compounds are useful in the treatment of affective disorders such as schizophrenia, depression, Alzheimer''s disease, movement disorders such as Parkinsonism and dystonia, and other disorders which respond to dopaminergic blockade such as substance abuse and obsessive compulsive disorders. Further, compounds of this invention are useful in treating the extrapyramidal side effects associated with the use of conventional neuroleptic agents.
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- Microbial transformation of selected carbazole derivatives
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A strain of Pseudomonas aeruginosa and another of Aspergillus fumigatus are found to have the ability to degrade carbazole derivatives. These strains show different specificities for growth on 1- and 3-methylcarbazoles and accumulate forraylcarbazoles as end products in low yields. Pseudomonas species degrade 1- and 3-formylcarbazoles to the corresponding carboxylic acid derivatives which in turn are decarboxylated to carbazole in high yields. This strain also biotransforms the N-acetylcarbazoles (8, 9 and 10) and the respective deacetyl-derivatives (7,2 and 11) are obtained in good yields. This study provides an evidence in favour of the suggested biotransfonnation of 3-methylcarbazole to carbazole via 3-formylcarbazole and carbazole-3-carboxylic acid in the plants.
- Chakraborty,Chowdhury
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p. 617 - 620
(2007/10/03)
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